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How To Transition From Clients to Digital Products, An In-Depth Step-By-Step Guide

January 16, 2019

Whether you’re thinking about transitioning away from clients completely or you simply want to start offsetting your revenue with a digital product (like an online course or an e-book) this guide will help you.

We, Caroline and Jason Zook, the people behind Wandering Aimfully, both come from a client-business background. I, Jason, started my first business in 2007 called Thought & Theory which was a small web design company. Caroline started a design business focused on branding in 2014 called Made Vibrant.

(Ps. Feel free to watch the abridged video version of this guide here:)

Transition from Client to Digital Product Worksheet

We know it’s unconventional, but we’re happy to give away some of our resources without making you give us your email address first. That said, if you DO find this guide and this worksheet helpful, sign up for our newsletter where we share worksheets like this every Monday.


We’ve worked with thousands of clients and know how helpful it can be to create a revenue stream that isn’t directly tied to trading time (one-on-one) for money.

But, transitioning your business from clients to digital products can be daunting. Where do you start? What digital product is best? How the heck do you find the time to create a digital product while barely having enough hours in the day to run your client business?

We’ve got you covered! In the next few sections of this guide, we’ll break down the transition from clients to digital products in manageable and practical steps.



Make The Transition From Clients to Digital Products by Making Your Client Business More Efficient

Wait, what? We aren’t diving head-first into the digital-product-creation waters? No friend, we are not.

You see, part of making any transition in life (or business) is to do so gradually so that you don’t overwhelm yourself and sabotage your chances of actually completing the process.

Raise your hand if you’ve tried to make a big shift in your life only to fall back into old habits a few weeks later? Yeah, we’ve been there too.

This is why we start this guide with an important foundational task…

To create the time and space needed to move from clients to digital products, your client business needs to be as efficient as possible

Everyone put on your Practical Pants (patent pending), it’s time to get a few key pieces of your client business humming along as smoothly as possible.

Efficiency Step 1: Get a grip on your daily schedule using time blocking.

We can’t stress the value and importance of time blocking enough. The basic principle is to look at every hour of your day (or 30-minute chunk) as a block of time that you can spend on work, life, etc. Let’s say you want to only spend five hours working every day. Your time blocking might look like this:

  • 8am-9am: Wake up, breakfast, morning meditation, take care of kids, etc
  • 9am-10am: Catch up on emails
  • 10am-12pm: Work for two consecutive hours on Client ABC
  • 12pm-1pm: Break for lunch and emails/social media
  • 1pm-4pm: Work for three consecutive hours on Client XYZ
  • 4pm-5pm: Gym, snack, etc
  • 5pm-Bed: Family time, relaxation, being an adult

That’s just one example of how you can structure your day using time blocking. One important thing you might notice is that time blocking isn’t reserved just for working hours.

You want to use time blocks for your life/adulting schedule as well because if that’s not in order it will impact the time you have available to work on client projects each day.


How to use time blocking to track your time better

This example image of time blocking shows the hours you block off for client work. It’s also a great way to see how many billable hours you spend each week to ensure you’re getting paid for your time spent work. In this visual, you’d ideally be working 25 hours per week!


Efficiency Step 2: Track your time blocking and see if it matches your client estimations.

When you run a client-based business your time IS money. Each hour you work you need to be getting paid for otherwise, you’ll run a business that isn’t profitable. Use a time-tracking app like to actually “clock in” when you start working.

As example, you could start tracking your time using the schedule above at 10am. Did you, in fact, get two hours of work done for Client ABC as you planned? Did the tasks and milestones you had for that client get accomplished?

By actually tracking your time and comparing it to your client proposals/estimates you can find out how efficient your business is currently running.

Efficiency Step 3: Once you start managing your time better, the more you’ll have of it!

Time is a funny thing. When we give ourselves as much time to accomplish a task it can feel like that task goes on forever. This is proven in science by Parkinson’s Law:

Parkinson’s law is the adage that “work expands so as to fill the time available for its completion”. If you give yourself three hours to complete a task your brain will think it has three hours even if the task could be completed in one.

By constricting the amount of time you can spend on any given to-do item, you’ll get better at working quickly and efficiently. Both Caroline and I saw this happen firsthand with our design businesses. What used to take us multiple hours could get accomplished in a fraction of the time when we only allowed ourselves a certain amount of time to complete what we were working on (yes, that included getting into “design flow”).

When your working hours are efficient you’ll get faster at accomplishing your work, thereby freeing up hours for… you guessed it… digital product creation!

But hold on, we’re not quite ready to jump into digital product creation. Let’s tackle one other big foundational topic…



To Go From Clients To Digital Products You Need To Set Your Lifestyle Vision

You know those people that say, “describe for me your perfect day – what does that look like for you?” and you just want to slap them? We get it. We want to slap those people too at times. However… they bring up a really valid exercise.

What does your ideal life look like when you factor in your work?

It can be easy to dismiss the perfect day question as impossible. No one has a perfect day, right? Well, just because no one actually HAS a perfect day, doesn’t mean we can’t set ourselves up for the best day possible.

Part of transitioning from client work to digital products is understanding what your life looks like during the transition and after (depending on what your specific goals are).

Let’s use an example scenario: You make a full-time living as a web designer, but in 6 months you want to offset half your income with digital products and in 12 months be full-time with digital products only.

Your Lifestyle Vision for the 6-month part of the transition could look something like:

  1. Half of your monthly income is from digital products (let’s say you were making $4,000/month so that’s $2,000 in digital product income)
  2. Half of your workweek would be spent on your digital product side of your business (you work 40 hours per week, so 20 hours are spent on the digital product side)
  3. With half the amount of clients, you feel freer, more relaxed, and don’t feel the stress to constantly be under the pressure of someone else’s deadlines
  4. With half of your income coming from digital products, you can be pickier with what clients you take on

Now, obviously, those 6-months milestones aren’t going to happen just because you envision them happening. That’s what the rest of this guide is for! But before we jump ahead, let’s also outline examples for 12 months.

Your Lifestyle Vision for your business in 12 months:

  1. Your entire monthly income is coming from your digital products (yay, you!)
  2. Every hour you spend working each day/week/month is for your digital product customers
  3. You have a growing audience of fellow web designers who are happy to learn from you
  4. You are thinking about your next digital product and are excited by all the possibilities
  5. You may take on the additional client if it’s an absolutely perfect fit (but you don’t need it!)
  6. You are happier, you feel like you control your time more, and you look forward to Mondays for the first time!

Now that you have your Lifestyle Vision, are you ready to put in the effort to make it a reality?

It’s great to imagine your perfect life. It’s wonderful to think about your work days filled only with work you love doing. But these things don’t happen because you simply think about them.

Your ideal life happens when you prioritize making it happen.

What are the steps you need to take to get yourself from where you are right now in your transition to digital products?

  • Do you need to carve out 1 hour per day to build your audience? (coming up in Step #3)
  • Do you need to carve out 2 hours per week to create content? (coming up in Step #4)
  • Do you want to offer a pre-sale for a digital product idea to your existing audience? (coming up in Step #5)
  • Or are all of those things getting ahead of the fact that you need to go back through Step #1 and make your existing client business more efficient?

Use your Lifestyle Vision to write out a plan of action to get you where you want to go in the next 6 or 12 months. Break it down month by month or week by week to give yourself an action plan.

Write your own Lifestyle Vision



A Digital Product Business Needs An Audience

Odds are if you run a client business right now you may not have an email list of any kind. You might have social media accounts but they’re used more for photos of your dog and your food adventures than anything business-related. Unlike digital products, having an audience isn’t a necessity when it comes to landing clients and working with a handful of people each month.

If you want to transition to selling digital products, building an engaged audience around your product topic is an absolute must.

Fear not! Building an audience doesn’t have to be scary and intimidating. You also DON’T need to build a big audience. What you need to focus on is building the right audience of people, people who will become customers of your digital products.

I’m going to highlight some high-level audience building tactics in the next few paragraphs but we also have an accompanying guide devoted to Audience Building if you want to bookmark that for future reading: The Ethical Guide To Building An Email List Without Sleazy Tactics

Who is your ideal customer?

For the rest of this guide let’s pretend you’re a web designer (haven’t you always dreamed of pushing pixels around??) You currently offer your web design services to clients and that’s as far as you’ve gotten. This is you and this is the example we’ll focus on going forward. Cool? Cool.

As a web designer who works with clients you know what it takes to run a web design company, or just work as a freelancer, or however you want to describe it. The person you KNOW you can help is a previous version of you!

Helping a previous version of yourself means you already have the knowledge you need to be valuable!

So often people want to embark on a completely new journey with digital products, forgetting that they’ve spent years honing a skill they can teach other people (read: previous versions of themselves).

One example customer: Someone who is just getting started as a web designer.

Okay, great. We have a customer in mind, but let’s define a few more things about them to make them your ideal customer. Some questions to think about (and answer):

  1. What values does that person have? Do they value their time? Flexibility?
  2. Do they have strong morals of who they want to work with?
  3. Do they use humor or some other personality trait to stand out from others?
  4. Do they work with certain programs or using certain web design skills?

By answering those questions and adding more texture to your example customer you create your ideal customer. Now you might talk about your ideal customer like this:

I help web designers who want to work a flexible schedule, who won’t work with companies that harm the environment, who aren’t afraid to make jokes about The Office, and who predominately build Squarespace websites.

Holy moly, that’s specific, right? Do you immediately think that feels limiting? Well, guess what? It’s not.

It’s unlikely that you will always be talking to your ideal customer but your goal should be to try to so you can attract the RIGHT people and push away the wrong people.

By getting specific with who your ideal customer is you can speak more clearly to the things that resonate with them. Trust me on this one, the more you can create a connection with customers, the easier it is to help them AND get them to purchase from you.

Idea Customer Exercise

You are not going to build your digital product (ideal customer) audience overnight (#realtalk)

Remember that Lifestyle Vision exercise where we said 6 months and 12 months were the milestones? Well, that’s on purpose because it takes time to build a digital product business while running your existing client business.

The things you’re going to need extra time for while you make the transition from clients to digital products are:

  • Picking the right digital product idea
  • Validating your product idea
  • Building an audience around your product topic
  • Creating and sharing content around your product topic
  • Turning your product idea into an actual product!

Right now we’re just talking about the third bullet in that list, so you can see how thinking you’ll build an audience overnight might not be a practical idea.

How to build an audience of ideal customers using a slow and steady approach

We do have another in-depth guide that goes into audience building, but we won’t leave you high-and-dry here. The quick hits of what you need to think about when it comes to building an audience of your idea customers are:

  1. Be laser-focused in what you write about, share, etc
  2. Be helpful and/or entertaining as it relates to your ideal customer
  3. Be consistent and show up for them often
  4. Be authentic and don’t hide what makes you, you! Be weird!
  5. Make it easy for someone to join your audience (sign up for your email list, etc)

Now, granted these five items all have their own bit of nuance and tactics, but they are the most important things should focus on.

Two items of additional reading if you want to dig deeper on building an audience:

The Ethical Guide To Building An Email List Without Sleazy Tactics – Our in-depth guide I mentioned on building an audience. This is the way we’ve built email lists over 25,000+ people who support us and have been the main source of our income since 2013.

Define Road Runner Rules To Create A Foundation For Your Business – To go a bit deeper into identifying your ideal customer you can use this Road Runner Rules article to create a set of rules for your business.

The most important thing you can do when it comes to building an audience is to show up for them in a helpful way consistently.

We’ve watched it happen time and time again: Someone puts up a website, has defined their ideal customer, starts creating content, has an email list, and then two months later completely stops showing up. Why does this happen so often? Because people’s expectations about how many audience members they’re going to attract in a short amount of time are never clearly defined (and if they are, are unrealistic).

What size audience do you need to meet your digital product business transition goals?

It’s time to work your way backward from your 6-month Lifestyle Vision and see what needs to be done in the audience building part of this transition process.

Let’s bring our example back of having $2,000/month in digital product income (6 months from now)

When it comes to digital product sales, a really good email list will convert at 3-5%. To be honest, if you’re starting your audience from scratch right now, you’ll probably see a much higher conversion percentage because you’re going to build an audience around a specific topic and digital product offering.

For our example, let’s assume you’re selling a $100 online course. Quick math would tell us that you’d need 20 customers per month to reach your 6-month goal of $2,000 per month in revenue.

(Feel free to adjust these example numbers with your own estimates to get the most realistic idea for your situation!)

With 20 customers being your estimated number, if we go back to that 3-5% conversion metric and pick 5%, you would need to grow an email list of 400 subscribers in 6 months (400 * .05 = 20). That doesn’t sound too bad, right? It shouldn’t! But remember, you’re trying to make $2,000 per month, so you may need to set your sights a bit higher by the end of 6 months if you want to get 20 customers per month.

So, let’s recap:

  • You want to make $2,000 per month in 6 months
  • You have a $100 digital product
  • With an estimated conversion of 5%, you need 400 email subscribers to get 20 customers
  • That’s 66 subscribers per month or 2 subscribers per day

These numbers are ABSOLUTELY doable! The key is going to be establishing realistic numbers for yourself and then making sure you’ve built a content funnel to attract and help the right customers.

Speaking of content, ready to talk about that?



Why (Focused) Content Creation is a Foolproof Way To Build a Digital Product Business

There’s one simple thing I want to ask you to kick off this section on content:

Where do you go when you need to find the answer to a question?

You answered Bing, right? It’s totally Bing! Okay no, you probably said Google (or maybe even YouTube).

The way you think of searching for answers to questions is the way you should think about creating content to grow your digital product audience!

While social media can be important, we believe digital product businesses need searchable content FIRST. Sure, an Instagram and Twitter strategy can be helpful, but those platforms don’t readily offer up answers to people’s questions (unless, you know, that question is how many cute puppies can I scroll through in the next 4 hours??)

Creating searchable content is a critical step in building a digital product business

If you guessed that we had a separate guide dedicated to content creation and search engine optimization (SEO), then you would be correct! I’m not going to leave you high-and-dry in this guide, but you may want to bookmark our SEO Guide as well.

Bookmark this sucker for future reading: Everything You Need To Know From My Experience With SEO

When I say “searchable content” I’m explicitly referring to written posts/articles or videos. Seeing as Google and YouTube are the #1 and #2 places people go to search for answers to their questions, it makes sense to focus your content creation efforts on one of those platforms first.

Wandering Aimfully Google Search Results

That image shows you two articles that are the #1 result in Google and drive significant traffic to this website. But, and this is important, those articles were never written to be the #1 result in Google, they were written to be helpful and to answer a specific question we knew people were searching for (because we searched for it ourselves!)

You don’t have to be a great writer to create helpful content

One of the biggest myths when it comes to creating content is that you have be a “writer” in the sense that most of us think about that word.

Raise your hand again if you have imposter syndrome when it comes to writing. It’s okay if your hand is up, we’ve been there too!

I was most certainly NOT a writer when I started my previous website JasonDoesStuff that shared a helpful entrepreneurial article every week from 2014 – 2018. Each week I set out with the intention of writing a helpful article about taking more action in your life and business (a topic that, admittedly, was a bit too vague). From 0 website visitors and 0 email subscribers in 2014 my articles started to gain some traction in Google search results and through my own promotion efforts. At the end of the first 6 months, I’d written 26 articles, my website was consistently getting over 10,000 visitors per month, and my email list had grown to 2,500+ people. This was without having a guide like this to help me speed up that process (or have any concrete plan of action!)

One hugely helpful tactic I used to go from what the heck do I write about to cranking out thousands of words every week, was to start every article with: “I want to help you…”

Those five little words were an amazing jolt to my writing muscles. All I had to do was fill in the rest of that sentence with something I wanted to help people with and I had a topic to expand upon.

Now, for you, we’re going to take that tactic up a notch and go back to the focus on searchable content. I’m using a web designer for the examples below, feel free to replace with your current focus and come up with a few “I want to help yous…” for your ideal customer/audience member:

  • I want to help you learn how to get web design clients that don’t suck
  • I want to help you build a great web design portfolio that stands out
  • I want to help you learn Adobe Photoshop without feeling overwhelmed
  • I want to help you decide if you should use Squarespace, WordPress or Webflow to design websites

On and on and on. My guess is you can probably rattle off 10-20 “I want to help yous…” in the next 5-10 minutes. And the beauty of that is you just came up with your first 10-20 articles!

Consistency is almost as important as quality at the beginning of your content creation journey

When you’re just dipping your toes in the content creation waters it can be easy to think an article isn’t good enough. Yet, unless someone emails you and tells you that, there is no reason you should think it.

Now, I’m going to be 100% honest with you: Your early content is probably going to suck. This is OKAY!

Every couple years I go back and read through my old articles and I’m embarrassed by them. How the heck did people not cringe at what I wrote? But then I remember that most people are just looking for answers to their questions, they don’t really care about how well something is written.

The important thing to focus on is showing up consistently so your growing audience builds trust with you.

Consistency will prove to your readers that you’re going to deliver helpful information to them and on a schedule you’ve promised. You are delivering value directly to them and they will thank you for it by continuing to give you their attention (and hopefully eventually some of their money for your digital product).

We, humans, love consistency. Our brains enjoy repetitive patterns. Rather than letting perfectionism or thoughts of self-doubt keep you from hitting publish on your writing, remember that consistency is more important than quality early on.

Further reading: Afraid to start writing? Give yourself permission to start ugly.

Create content for places where people are already hanging out

If you’re new to the content creation and audience building world, it can feel like you’re talking to absolutely no one. We should know, Caroline sent her first weekly email newsletter to just FOUR subscribers (yes, 4, and two of them were her email and my email).

One way to avoid feeling like you’re talking to no one is to go where people are already spending their time. This is known as “guest posting” in the content creation space.

Important Note: We want it to be clear you should be creating content for your website and audience FIRST before doing guest posting. It’s important to have your own content and audience building stuff in place for when you direct people from other sites to you!


Guest posting secret to success: Pitching, pitching, and more pitching.

You aren’t going to be awarded a guest post on someone else’s website just because you want it to happen. You’re going to need to pitch yourself and your content so it makes sense for someone to let you get access to their audience.

There are a couple important things to think about when it comes to pitching an article to someone:

  1. First things first, make sure they accept guest posts (we get emails all the time from people and we’ve never had a guest post, it’s frustrating and we immediately mark those emails as spam)
  2. Find a unique topic that hasn’t been written about on their site yet (yes, you will need to do some research so you don’t pitch an article idea that’s already on their site)
  3. This should go without saying, but, make sure you’re guest posting on a site with an audience relevant to the audience you want to be building (you don’t want to guest post on a food blog if you’re trying to attract web designers)
  4. Be prepared to follow up with people if you don’t hear back and be okay with people telling you “no thanks”
  5. Make sure you can have some sort of call to action to your email list in your guest posted article (it doesn’t do you any good if you aren’t allowed to promote yourself a little bit to their audience)

Think of guest posting as one segment of your Totem Pole of Content (also patent pending). You don’t need your entire totem pole to be devoted or reliant on other people’s websites, but it is helpful to tap into existing audiences now and again.

Wherever you’re creating content, make sure it leads to an email list so you can grow your audience

This may seem like a no-brainer, but even on your own website, it should be extremely clear that someone should join your email list after reading an article. Heck, you may even think about having an email signup form in the middle of an article if that feels right.

Remember, you want to help people, but you also want to reach your goal of transitioning away from a client-focused business. Having an audience gives you people you can help and promote your digital products to. Whether that’s on someone else’s website or your own, be sure to have an easy way for people to get on your email list for more helpful content and updates around your specific topic of focus.



Ready To Validate Your Digital Product Idea? Offer a Pre-Sale!

We looooooooove pre-selling around these parts. In fact, I believe we’ve pre-sold every single digital product we’ve ever created (and we have around 30+ products under our digital belts!)

Pre-selling your digital product does two things really well:

  1. It validates your idea with more than someone giving you their email address
  2. It shows you that you’re building a highly qualified audience of customers

Idea validation is wonderful, especially when there is money associated with it.

Someone giving you money just for your idea is all the proof you need to know you’re on the right track to running a digital product business!

How do you create a pre-sale page for your digital product?

You may be thinking this is going to be a long section, but truthfully, pre-selling does not have to be very complicated. In fact, all of our pre-sales pages have been simple and straight to the point.

Use the P.O.P.P. method for the content on your pre-sale page (Problem, Outcome, Product, Purchase)

In these few paragraphs, we’re going to keep up the web designer example and pretend you’re selling a course that helps web designers get more clients.

Problem: The first thing you want on your simple pre-sale page is a headline that grabs your potential customer’s attention and addresses the clear problem you’re solving for them.

Example: Is finding your next web design client stressing you the heck out? Do you wish you had a system you could follow to land clients consistently?

Outcome: Next, after you’ve stated the problem, you’ll share your solution to that problem and the outcome your customer wants for themselves.

Example: Years ago when I was doing web design the bane of my existence was wondering where I’d get my next client from. Every week it would weigh on me and it effected my ability to work without stressing out about where the next client would come from. That all changed when I created a simple process that carved out actual time with practical tasks to help get more clients. In just a few short weeks of work, I was able to go from stressed out about where my next client would come from to being booked 3-6 months in advance! I can help you have the exact same results!

Product: You addressed the problem, you shared your own outcome, now it’s time to show how the product you want someone to purchase is the answer to the problem.

Example: I’d like to introduce you to Web Designers Who Get Booked, my step-by-step online course that walks you through the exact processes I created to go from stressing about clients to booking my web design services months in advance. In Web Designers Who Get Booked, I’ll share the client outreach tactics that actually work, my non-complicated system for staying ahead of my client schedule, and a few pointers on how to feel more confident when it comes to selling your web design skills.

Example Part Two: You may also want to share a bulleted list of the lessons included in the course (doesn’t matter if you’ve created them yet) and if you can get some social proof (testimonial) from someone who’s used your processes, include that as well.

Purchase: Finally, you stated the problem, your own outcome, you described your digital product offering, and now it’s time to let someone pay you in advance!

Example: You’ll obviously have a buy button and connect that to a payment processor of your choosing (Gumroad is really easy to use for this, or if you’re building an online course my software company Teachery can help you pre-sell your course). Alongside the buy button, you want to make it 100% clear that the online course/digital product isn’t quite ready yet but will be delivered in X amount of days (or on a specific date). Let your customer know they are getting early access and maybe even offer them a discounted price on the course since it’s a pre-sale. It’s also a good idea to only offer a pre-sale for a short amount of time so you can get out of sales/marketing and actually make your digital product!

Click here to view the example pre-sale page 👍

Example Pre-Sale Page using P.O.P.P. Method

How long should your pre-sale last and should you offer a discount?

These are two great questions to ask yourself, but as you can imagine we have some advice and personal experience with both.

How long should a pre-sale last? We think 48 hours minimum and 1-week maximum.

If you have a larger audience and you’re not trying to hit some huge financial goal (remember your Lifestyle Vision from Step #2!), you may want to constrict your pre-sale to a shorter amount of time (48 hours). Why? Having fewer customers, in the beginning, is actually better because you’ll have fewer people to get feedback from and manage.

If you have a smaller audience you might need one full week along with multiple emails to convince your customers to jump on your pre-sale.

Whichever audience-size category you fit into, we recommend at least sending this many emails and on this schedule for your pre-sale:

  • First email: At least 1 week out, saying the pre-sale is launching on X date
  • Day before: Pre-sale is coming tomorrow, get excited! (Re-use your Problem, Outcome, and Product here)
  • Pre-sale launch day: It’s up, go purchase, pre-sales close down X date
  • (If pre-selling for a week) 3 days after launch: Share more about your outcome and the digital product details
  • (If pre-selling for a week) Day before closes: Pre-sale is ending, what questions do you have?
  • 6 hours before pre-sale closes: Pre-sale is going away and never going to be offered again!

This may seem like a lot of communication with your email list but remind yourself how often you launch and create digital products. Especially if this is your first product, you’ll need more touch-points to get your audience warmed up to buy.

Should you offer a discount with your pre-sale? Our vote is YES.

A customer purchasing your product from you before it actually exists is a really awesome thing. If you can afford to offer a discount and can make it reasonable (a 5% discount is dumb, don’t do that), then we firmly believe in offering a pre-sale discount.

You can position this in your emails and on your pre-sale page by saying something to the effect of: Web Designers Who Get Booked will be $100 when it goes live, but for this pre-sale, you get 25% OFF and only pay $75!

Offering someone a discount during a pre-sale doesn’t devalue your product. If anything, it rewards a customer for taking action and proving to you that your idea is worth paying for.

Don’t forget to clearly communicate with your pre-sale buyers

Remember, these folks are taking a chance on you. They’re buying something from you that doesn’t even exist yet and you owe it to them to communicate effectively and honestly.

During my previous pre-sales, I’ve sold a product that would take two months to create. During the two months after the pre-sale was over and leading up to the release of the product, I communicated with my pre-sale customers every two weeks. Not only did this make them feel at ease and that they knew I wasn’t going to move to a tropical island and never deliver the course I promised, but it gave me a chance to get some feedback on content within my product and to get customers excited by showing behind the scenes photos and screenshots.

If you want to avoid angry or complacent customers, plan to reach out to your pre-sale buyers and they will thank you for it by sharing your digital product for you once it exists for other people to buy it!

Bonus pre-sale tip: Can you plan a little surprise and delight for your pre-sale customers?

Yes, your pre-sale customers probably got a discount on your digital product, but you should think about planning to surprise them with something else along the way.

When I pre-sold my Get Sponsorships For Podcasts course back in 2015 I had a digital book called One Week To Profit (priced at $99) that had seven helpful tips for online business owners. To me, it felt like a nice surprise to give them this digital book for free and it felt like a good fit since most podcasters own their own businesses. When I surprised my pre-sale customers with this added bonus people were shocked and excited. Many of them went to Twitter and Facebook to talk about how happy they were and how other people should look into buying stuff from me.

What is something you can surprise and delight your pre-sale customers with? It doesn’t have to be a full-blown digital book, it could be as simple as a few extra worksheets, templates, or even a group call once the course is live to answer Q&As.

Keep something in your back pocket and your customers will thank you for it by using word of mouth to promote you and your products!



It’s Time To Create Your Digital Product, Where The Heck Do You Start??

Now, there’s a lot to unpack here and we aren’t going to pretend we can walk you through the digital product creation process in just a few paragraphs.

Shameless plug, if you’ve read the majority of this guide and have found it helpful but you’re looking for some step-by-step processes, accountability, and want to transition from clients to digital products without burning out in the process our Build Without Burnout Academy is perfect for you!


Let’s chat about three different digital products you can choose from and the pros and cons of each

Online courses are our favorite digital product

Pros to online courses: Online learning is a humungous industry and people don’t want to go to physical buildings or crack open long boring books to learn anymore. People want to learn from people who’ve been where they want to go and online courses are the perfect medium for that. One of our favorite parts about online courses is the blend of teaching content, written word, and a contained space for knowledge that’s easy to access.

Cons to online courses: It can be difficult to limit yourself on how much you want to teach in an online course. It can also be hard to price your online course, especially if you’re creating your first one. There are some technical abilities needed, but that’s really dependent on the complexity of your course (does it have videos, timed components, worksheets, etc?) And, you typically need to pay for an online course software, you can’t easily host a great online course on your own website with a few clicks.

E-books are wonderful… when they don’t suck

Pros to e-books: E-books are a great way to give someone an in-depth look at something. Heck, we could’ve turned this guide into an e-book and it would probably sell on its own. Unlike paper books, you can update the info in an e-book easily and it doesn’t have to “go to print.” Plus, e-books can be sold easily through other marketplaces (think: Amazon, iBooks, etc).

Cons to e-books: Designing and laying out an e-book that doesn’t suck isn’t something all of us have the ability to do (I know I don’t!) Prepare to invest money and pay an e-book designer to help you make your e-book easy to read and fun to page through. E-books can get a bad rap but that’s mostly because people phone-in the production quality and try to charge a lot more than the knowledge in the book is actually worth.

Membership communities

Pros to membership communities: Creating monthly recurring revenue with a membership community is a great way to have a consistent income. For us, having a paid membership community (shameless plug!) is also personally fulfilling because we’ve surrounded ourselves with people who are on a journey we know we can help with (and are on ourselves). Membership communities are great because they’re flexible and can evolve over time.

Cons to membership communities: The technical logistics of a membership community can be challenging depending on what you’re trying to do/build. Also, churn. Churn is the term for people canceling their membership and this is something that’s bound to happen. Fighting the good fight against member churn takes effort and can give you some mental hurdles in the beginning.

There are many other types of digital products you could create. We simply wanted to highlight the three we have the most experience with that most folk (like you!) can create on your own.

No matter what digital product you choose, start with a basic content outline

Cool with you if we bring back our Web Designers Who Get Booked online course example? Great. Let’s do that!

Creating an outline as the first step in your digital product creation process is mandatory. You may want to dive into the more fun aspects like design, video recording, etc, but your product outline is your foundation and you NEED a solid foundation.

Keep it simple with your first outline and use a bulleted list

  • Bulleted lists are wonderful for outlining your digital product
  • You can put broader strokes down as main bullets
    • Then have smaller thoughts or ideas nested in
    • Maybe you have lots of smaller thoughts around a big idea?
    • That’s great!
  • Your first bulleted list for your outline should be a brain dump
    • Don’t overthink it
    • Don’t over format it
    • Just get your thoughts put down in a list you can move around

Okay, I think you see what I did there, yeah? But that’s exactly how you want to think about the outline for your digital product. Let’s look at an outline example for Web Designers Who Get Booked:

  • Lesson 1: Understanding the need for prioritizing client outreach time
    • 1.1: Clients pay your bills
    • 1.2: It takes time to land a client
    • 1.3: Not all clients are created equal
  • Lesson 2: Treat your client outreach like your actual work time
    • 2.1: Carve out ONE day per week for client outreach
    • 2.2: Carve out 30 minutes per day to update your outreach spreadsheet
    • 2.3: Use the “secret art of following up”
  • Lesson 3: Managing your client schedule better
    • 3.1: What do you currently use? If you’re booked well in advance, skip this lesson
    • 3.2: Recommended client schedule process (with templates)
    • 3.3: Create good communication channels you can keep up with
  • Lesson 4: Let’s talk about money
    • 4.1: Getting booked in advance means you need to pay attention to your future money
    • 4.2: Deposits, should you take them? YES.

Hopefully, that outline example gives you food for thought on how you might structure the content of your digital product. The great thing about putting together a simple outline is that you can move different parts around easily and it sets you up for…

Make your digital product creation process less daunting by re-utilizing time blocking

If you put on your to-do list, “make an online course” you will never get it done. Ever. That’s a really big task. Instead, you want to use your digital product outline as your guide and then pepper in all the ancillary things it takes to bring your digital product to life.

Remember the Time Blocking exercise we brought up wayyyy back in Step #1 of this guide? Use it again and block time off on your calendar each day for your digital product creation process.

Here’s an example for you:

  • 8am-9am: Wake up, breakfast, morning meditation, take care of kids, etc
  • 9am-10am: Catch up on emails
  • 10am-12pm: Work for two consecutive hours on Client ABC
  • 12pm-1pm: Break for lunch and emails/social media
  • 1pm – 2pm: Write Lessons 1.1, 1.2, and 1.3 for Web Designers Who Get Booked
  • 2pm – 3pm: Work on the branding in Teachery for Web Designers Who Get Booked course
  • 3pm – 4pm: Record Keynote for Web Designers Who Get Booked introduction video
  • 4pm-5pm: Gym, snack, etc
  • 5pm-Bed: Family time, relaxation, being an adult

To make the time blocking process even easier you may want to do a separate bulleted list of every single task you can think of related to creating your digital product. This may seem like a waste of your time, but it’s actually really helpful when you want to start time blocking!

We know it’s unconventional, but we’re happy to give away some of our resources without making you give us your email address first. That said, if you DO find this guide and worksheet helpful, sign up for our newsletter where we share worksheets like this every Monday.


It’s time to build your digital product!

If you’re a go-getter, read the previous section, and started writing your outline, you’re on your way to building your digital product! YAY YOU!

We like to think about building digital products in these phases:

  1. Do all the writing for our product (outline, lessons, etc)
  2. Turn the writing into actionable teachings (Keynote, Powerpoint, Adobe inDesign, etc)
  3. Do all the recording for our product (videos, audio, whatever production is needed)
  4. Put together the home for our product (where does it live, how do people access it, etc)
  5. Sales page and sales emails (write this stuff, test it thoroughly)
  6. Customer communication (welcome email, file delivery, expectations, etc)
  7. Some sort of surprise and delight

After we’ve completed building our digital product we do our own simple testing:

  1. Sign up for our digital product in a different browser so we get the real experience
  2. Send our product to a few friends or pre-sale customers for them to test
  3. Fix whatever went wrong (something always goes wrong, that’s why you test!)

This list of things may seem daunting. Remember, you want to break all of this stuff down into smaller pieces that you can tackle in different time blocks.

Is your digital product going to be an online course? We can help with that!

Out of all the digital products we’ve created we have the most experience with online courses. We actually have TWO How To courses about making online courses.

If you’re looking for a step-by-step guide to creating an online course (or e-course) as your digital product, please read this article: How To Build And Sell Your First E-Course

Say it with us: Iteration is OKAY!

Before we wrap up this section on creating your digital product we want to remind you of one important thing: Digital products are digital. Yep, mind-blowing info, right?

It’s so easy to get stuck in the weeds trying to create a perfect digital product out of the gates. There’s no doubt you’re going to obsess over some part of the creation process (we know, we’ve been there). However, it’s incredibly important you remember how easy it is to update a digital product!

Your digital product is not etched into a slab of stone, so be okay with an imperfect product that you iterate on and improve over time.

Customer feedback should help guide and improve your digital product

You’ll most likely have a list 20 bullet points long with new things you can add to your digital product but odds are you may only need to add 3-4 of those things.

Pro-tip: Build the smallest, best version of your digital product and then survey your paying customers with questions about what could be added to it.

Don’t ask strangers on the street. Don’t ask your friends. Ask the people who paid you money for your digital product and then add the stuff that gets asked about the most.

This mindset of starting with an imperfect digital product and being willing to iterate on it over time is the BEST way to keep your sanity in the process. Plus, when you do add new stuff to your digital product and you give that new stuff to your existing customers, they’ll love and appreciate you for it!



Launching and Continuing to Sell Your Digital Product

If you recall, this guide is about making the transition from clients to selling digital products. The last part of that transition is going to be the part where you launch your product and continue to sell it.

There’s a lot that goes into launching and selling but we’re going to break down the bigger parts in five separate topics.

Launching and selling mindset (it’s time to get realistic)

Okay, let’s rip the band-aid off a few important things:

Defining your own success is important

It’s impossible to avoid the trappings of a “big launch” or a “six-figure launch” or any of the other headlines and success stories you read about in the digital product space. But… there is so much context to those stories that we don’t have. Instead, you need to define a realistic measure of success that matches your Lifestyle Vision.

Your first launch is not your last launch

Time and time again we’ve watched fellow entrepreneurs gear up for a big first launch, have less than amazing results (mostly because they didn’t define their own success), and then never launch again. Ugh. You should think of your first launch as your next starting line. It’s not a finish line in your digital product journey, it’s an entire new marathon you opt in to run.

Selling feels uncomfortable for all of us

It’s just a weird thing to do! You’re asking strangers on the Internet to buy a thing from you that you created out of thin air. That’s bizarre! Accept this. Understand it. Embrace the fact that you’ll feel uncomfortable but don’t count yourself out and NOT sell your digital product.

Creating a great sales page happens over time, not overnight

You’re seeing a recurring theme in this guide, aren’t you? Iteration. Tweaking. Testing. Using an experimenter’s mindset is part of the game, especially when it comes to crafting a sales page for your digital product.

Remember the P.O.P.P. method (Problem, Outcome, Product, Purchase) we told you about back in Step #5? It’s time to bring it back around, but expand it to: P. O. P. S. E. P.

  • Problem
  • Outcome
  • Product
  • Social Proof
  • Examples
  • Purchase

You already know the Problem, Outcome, Product, Purchase part, you can almost copy and paste from your pre-sale page for your main digital product sales page (maybe expand slightly if you have more to share in those topics). The two new things are:

(S) Social Proof, and why it matters on your sales page

Take a minute and remember the last thing you purchased that was recommended by a friend. It could be anything. The purchase was a no-brainer for you due to one important factor: You trust your friend!

Social proof on a sales page is how you show strangers on the Internet that other strangers on the Internet trust you. It’s as simple as that.

Do you have customer’s who have experience with your digital product? Send them an email and ask for 2-3 sentences about what they liked (make sure to get their approval to share their response). Boom, easy peasy.

If you don’t have customers yet? Get a few! Even if they get your digital product at a steep discount, or for free, spend the time to have someone actually use your product and give you a testimonial about it.

Add at least 2-3 pieces of social proof to your sales page and use photos of the actual people if you can (again, trust!)

(E) Examples: It’s time to play show and tell

When your digital product is ready to be sold you shouldn’t be afraid to play a little show and tell. One of the most frustrating things for me when I’m looking at sales pages is when I can’t see the actual digital product in any shape or form.

Are you selling an e-book? Give away the first chapter or two. Don’t be afraid to share what’s inside, if someone loves it, they’ll purchase the rest.

Are you selling an online course? Show people a screen recorded video that walks through the lessons, the content, and gives people an exact look at what they’re getting into.

You get the idea. Share visual examples of what you’re selling to instill trust in your prospective customers (and remove any guesswork on their part of what they’ll get).

No matter what digital product you sell, keep the P. O. P. S. E. P. method handy (Problem, Outcome, Product, Social Proof, Examples, Purchase)

Once your sales page is ready, it’s time for an email sales sequence

Whether you’re selling your digital product on an ongoing basis (“evergreen product”) or your doing a couple launches per year (“open and closed cart”) you are going to need a series of sales emails that convince someone your digital product is worth spending money on.

Our tried-and-true 7-email sequence for selling digital products

We really like doing open and closed carts for our digital products. We choose this method because it puts us in control of when we have to be in sales and marketing mode. Selling things as evergreen is fine, but we don’t like having the thoughts of sales and marketing in the back of our minds at all time. Plus, experience has shown us that an open and closed launch provides the urgency many people need to make an actual purchase.

That being said, here’s what our 7-email sequence looks like:

  1. Opening the doors next week, get ready! (Monday before launch)
  2. Launch day, go to the sales page (Monday of launch)
  3. Social proof and case studies (Tuesday, day after launch)
  4. Future outcomes you can expect (Thursday)
  5. Reply with any questions (Saturday)
  6. Share common objections people have (Monday)
  7. Last call, doors are closing (Same Monday, a few hours before close)

Wandering Aimfully 7-Email Sales Sequence

If you’re interested in getting a thorough walk-through of our 7-email sequence, we recorded an entire workshop about selling and our Wandering Aimfully Members get it included in their membership. If there’s one thing we have down to a science, it’s the process of selling and launching!

Selling your digital product is never completely set it and forget it

As much as some online marketers and entrepreneurs want you to believe, it’s pretty damn difficult to create a hands-off passive income digital product.

Myth: Creating passive income isn’t as passive as you think.

We’ve created over 30 digital products since 2013 and none of them have been 100% hands-off. Even the digital products that have sold consistently we’ve spent time:

  • Marketing and promoting them
  • Helping customers with any issues or problems
  • Improving the product over time
  • Tweaking the sales page or content funnel

Remember the example 12-month Lifestyle Vision from Step #2? It’s okay if you don’t we’ll remind you of what those things were:

  1. Your entire monthly income is coming from your digital products (yay, you!)
  2. Every hour you spend working each day/week/month is for your digital product customers
  3. You have a growing audience of fellow web designers who are happy to learn from you
  4. You are thinking about your next digital product and are excited by all the possibilities
  5. You may take on the additional client if it’s an absolutely perfect fit (but you don’t need it!)
  6. You are happier, you feel like you control your time more, and you look forward to Mondays for the first time!

As “passive” as you hope your digital product business to be, it will require time and effort. Just remember, you chose to transition away from client work for a reason!



We Want To Help You Avoid Overwhelm Transitioning From Clients to Digital Products

If you’ve read this far into this in-depth guide we have to imagine you are willing to do the work it takes to transition from clients to digital products. We also realize you might be a tad bit overwhelmed as there’s a LOT to unpack and implement here.

We’ve got your back with a 6-month guided program called Build Without Burnout Academy.

Within our Wandering Aimfully Membership is our cornerstone program Build Without Burnout Academy. It’s a six-month program to help client-based business owners transition into selling digital products —without burning out in the process.

This isn’t some secondhand knowledge we Googled, this is our exact experience as we transitioned from designers doing client work to creative entrepreneurs selling digital products.

Build Without Burnout Academy

How is Build Without Burnout Academy different from other programs?

The first and most important thing is it’s a 6-month long program. It’s not 6-weeks. It’s not a 6-month program you can cram into 1 month. It’s a program that forces you to stick to the timelines we’ve set to ensure that you don’t get overwhelmed and give up on transitioning from clients to digital products.

If you nod your head in agreement to any of these statements Build Without Burnout is for you:

You currently have clients but you know you want to create a digital product (like an online course, membership community, e-book, etc) and feel like you’ll never have the time.

You’re tired of trading time for money and feel like you’re always scrambling to find your next client to pay yo’ bills.

You’ve experienced burnout before due to overworking and you want to avoid it at all costs while still having a plan of action moving forward.

You’ve been sold the “you’ll make 6-figs with an online course!” dream and you aren’t having any of that (you’re okay with making fewer figs and enjoying your life in the process).

You’ve read nearly every word of this massive in-depth guide and thought, “I wish Jason just had this stuff as a guided program that I could follow because it seems kind of overwhelming just reading all of this.”

Build Without Burnout Academy is going to give you the step-by-step process as outlined in this guide, but in a format that you can stick with and be accountable to.

You’ll have weekly action items and to-dos, but the entire goal is to make it manageable with your current client business.

If you’re excited and ready to learn more, check out our Wandering Aimfully Membership page (remember: Build Without Burnout Academy is our cornerstone program within our membership).

We hope this guide was helpful for you!

We put a ton of time and effort into these guides. This one could have been twice as long and three times as thorough but we had to draw the line somewhere.

If you took our advice in this guide, don’t hesitate to reach out and let us know what was most helpful.

And if joining our Wandering Aimfully Membership feels right so you have a group of folks who are on a similar transition from clients to digital products, we’d be delighted to have you!

An In-Depth Guide on How To Sell More Products and Services Using Bumpsale

November 1, 2018

Do you want to sell more products or services, but felt like you’ve exhausted all previous sales efforts?

Maybe you have a brand new thing to sell, but you aren’t sure how much your audience will pay for it? Or, you simply want to make a few extra bucks and give your audience an exciting way to purchase what you already make?

Enter Bumpsale.


This in-depth guide will walk you through these topics:

(Feel free to click any of them to jump to that section or simply keep scrolling.)


First Up, What The Heck Is Bumpsale?

Bumpsale is a unique way to sell something using a bump in price after every purchase is made. The idea was originally conceived by me (the person writing to you), Jason Zook, when I created the project IWearYourShirt in 2008. I used the Bumpsale concept back then to sell spots on a daily t-shirt wearing calendar, where each day would increase in price (Jan 1 was $1, Jan 2 was $2, etc). Truthfully, I wanted to create some marketing and momentum with my pricing, little did I know that idea would turn into the Bumpsale app you see today.

Bumpsale does NOT help you sell spots on a daily t-shirt wearing calendar. That’s a very niche business model and we’d have gone defunct many years ago had that been our customer focus. Instead, we took the concept of bumping the price after each purchase and made a much more flexible product.

Bumpsale DOES let you quickly create a buy button that will increase in price after a purchase is made. The increase happens right on the page as your customers look at the buy button.

Bumpsale pop up window

These are the things you set when creating a Bumpsale (more on the specific steps in the How To Bumpsale section):

  • Starting price (start as low as $1 or as high as your heart desires)
  • Bump price (how much the price increases after each purchase)
  • Currency (over 135+ currencies supported!)
  • Set the amount of time someone can lock in their price
  • Style your button (button color and text)
  • Post-purchase URL (where customers go after the purchase is made)

As people purchase via your Bumpsale button, the price will bump live on your site. There’s a small snippet of code you add to your sales page that takes care of all the wizardry and selling-magic behind the scenes.

Quite simply, Bumpsale is an incredibly fast and nimble way to sell your product with some fun added urgency.


Why Should You Use Bumpsale To Sell Your Stuff?

We know how it goes: You create an online course, a digital book, a photo-pack, a membership site, a consulting call, a package for your freelancing services, or maybe even a Zebra Training Certification program. Whatever it is, you go through the normal sales cycles and while those can work, you want to shake things up a bit.

That’s where Bumpsale comes in! We created Bumpsale to spice up your sales and to give your customers an exciting way to purchase whatever it is you create (especially if it’s Zebra Certifications!)

⚡️ Bumpsale is lightning quick to set up: It’s about 4 clicks of your mouse and your Bumpsale button can be ready to start collecting sales. There’s a step-by-step video walkthrough below if you want to jump to that.

👍 Bumpsale is super versatile: We give you some basic styling options, but if you know some CSS, you can make your Bumpsale button look like anything your heart desires.

👌🏻 Bumpsale will cost you almost nothing: There’s no monthly fee for Bumpsale. There’s no per button setup cost. We simply collect a small 3% fee on every sale made with Bumpsale. Example: If you sell $1,000 worth of online courses, you’d only pay us $30. Not. Too. Shabby!

💃🏻 Bumpsale is fun for your audience: As you’ll see in the Proof of Concept section below, customers actually LOVE buying through Bumpsale. Usually, they’re getting some kind of discount, so that tends to help, but the excitement and uniqueness of a Bumpsale stands out from other standard sales tactics.

Bumpsale Customers


When Should (And Shouldn’t) You Use Bumpsale?

Using Bumpsale isn’t reserved just for Black Friday, Cyber Monday, or other holiday discounts. We DO recommend using Bumpsale around those times, but it’s also a very successful way to drum up sales whenever you need a little revenue bump!

You should use Bumpsale if you already have an audience of some kind.

Bumpsale does not bring an audience to your product (you handle that). We simply have a mechanism that helps make the sales process more fun. The most successful uses of Bumpsale occur when you give your audience a heads-up that you’re going to use Bumpsale, and have them waiting and ready for it (more on this in the How To Warm Up Your Audience section).

You should use Bumpsale for a short period of time.

It’s not that you can’t use Bumpsale for longer periods of time, we’ve simply seen the best results when a Bumpsale is run through a shortened time period. There’s no perfect amount of time, but 24 hours, 48 hours, 2-3 days, or a week tend to do really well.

NOTE: As a heads-up, there isn’t an expire feature within Bumpsale, you’ll just remove the button when your Bumpsale time period has ended – easy peasy!

You should use Bumpsale for pre-orders.

Pre-orders tend to work really well with Bumpsale because your audience is getting a discount and more people can get in at a lower price than they’d normally. Plus, the math can add up very quickly with Bumpsale over a standard discount. Here’s an example scenario:

  • Let’s say you have a $200 online course
  • If you start your Bumpsale at $20 and bump by $1
  • If you get 100 sales, you’ll make $6,950!
  • (The final bump price would end up at $119, which is still a 59% discount!)

Feel free to use the Bumpsale Calculator to get an idea of how much revenue you can generate with Bumpsale. Here’s a video of the calculator in action:

Bumpsale Calculator


You should NOT do tiny discounts with Bumpsale.

Looking at the example above, if you were to try to sell your $200 course, starting at $180 and bumping by $1, you probably wouldn’t see any traction at all. There’s simply no motivation for your customers. Plus, the urgency to purchase before the price increases doesn’t really matter. We aren’t advocating that every product has to have an enormous discount with Bumpsale, but the bigger the discount, the more traction and sales we’ve seen happen time and time again. If we look at the example scenario used a minute ago with a tiny discount, here’s how the math works out:

  • You have a $200 online course
  • You start your Bumpsale at $180 and bump by $1
  • If you get 20 sales (because people won’t pay OVER full price), you only make $3,790
  • (The final bump price would obviously end up at $200)

You should NOT drop a Bumpsale on your audience last minute:

Most likely, your audience has never heard of Bumpsale or seen it in action before. If you don’t clearly explain how it works, it can lead customers to be confused (never a good thing!). Give your audience at least a week’s notice, along with explaining how the Bumpsale will work and what they can expect. (Again, more on this in the How To Warm Up Your Audience section).

You should NOT run a Bumpsale without doing a real purchase of your own Bumpsale:

We hope this goes without saying, but some folks miss this critical step. Purchasing your own Bumpsale will give you the best experience to see what your customer will see. Did you notice anything weird? Did the redirect URL after a purchase go to the correct place? Did anything else happen that you expected/didn’t expect? Do a test purchase and refund yourself after!

Hopefully, that rest of this guide fills the gaps on the shoulds and shouldn’ts with Bumpsale. There’s an FAQ section at the bottom as well.


What Products Or Services Work Best With Bumpsale?

ALL OF THEM! Okay, if you’re selling sustainably raised goldfish, you probably won’t use Bumpsale to sell those. But, these things can be sold via Bumpsale and work really well:

  • Online courses
  • Digital books
  • Consulting spots
  • Freelance client spots
  • Coaching calls
  • Physical goods (you know, fidget spinners)
  • Music albums
  • Bundles*
  • Etc etc

*Bundles work especially well with Bumpsale because they are a grouping of products sold at a discounted price. The price is usually completely arbitrary, and potential customers of the bundle just want to snag a great deal on the total value of the bundle.

Anything you sell, that you are willing to make incremental revenue on, will work with Bumpsale.

An example of using Bumpsale to sell a bundle of products and services.

My wife and I put together a bundle of online courses, digital books, and a few downloadable goodies called The Vibrant Stuff Bundle (her site at the time was Made Vibrant and mine was JasonDoesStuff).

Vibrant Stuff Bundle

The total value of the resources inside The Vibrant Stuff Bundle was well over $2,500 if we sold every item in it at full price. But instead of offering a flat discount on the bundle, we used Bumpsale and generated over $20,000 in sales by starting the bundle at $1 and bumping the price by $1 after every purchase. These are the steps we took to create and sell our bundle:

  1. We whipped together a website on Squarespace just for the Vibrant Stuff Bundle
  2. We figured out how to do the redemption of all the resources inside the bundle (which ended up being a password protected page on Squarespace with links to redeem each product or service)
  3. We created the Bumpsale button, styled it with simple CSS, and added it to our sales page on Squarespace
  4. We used the automation service Zapier to create a “Zap” that would send an email upon every successful purchase of our Bumpsale to the customer (the email had a link to the password protected page and the secret password)
  5. We warmed up our audience and sold the bundle for 5 days (more on this a minute!)
  6. At the end of 5 days, the price had increased from just $1 to just over $200, netting us over $20,000!

The great thing about doing a bundle is that you usually don’t need to create any new products at all! Sure, you need to create the sales page that explains and sells the bundle, but that’s way easier than building yet another product from start to finish. Plus, who doesn’t love finding ways to repackage existing products you’ve created (while also giving folks a fun opportunity to buy a suite of products from you).


How To Set Up Your First Bumpsale Button

As I’ve mentioned a few times, setting up a Bumpsale is a mere few clicks of your mouse. I’m going to walk through the setup step-by-step, but there’s one important thing to keep in mind:

Bumpsale is just the button people click to purchase your product.

You need to put a Bumpsale button on your existing website (whether your site is on WordPress, Squarespace, Leadpages, Wix, Weebly, Dreamweaver, Geocities, etc).

As long as you can inject our small piece of Bumpsale code into an area of your website, you can use Bumpsale! And if you aren’t code-friendly, we’re happy to help you figure things out.

Watch the step-by-step Bumpsale video walkthrough:


Step 1 to create a Bumpsale: Connect your Stripe account Bumpsale

This is how you create your Bumpsale account. There’s no need for you to make an actual login, password, etc with Bumpsale. We let your existing Stripe account handle that info. If you don’t currently have a Stripe account, it’s completely free to set up and Stripe is the way to process credit cards (your customers won’t know Stripe exists).

NOTE: Stripe will send a receipt after a successful purchase. If you want to customize the way your receipt looks, you’ll do this in your Stripe account settings.

We do NOT support PayPal with Bumpsale (yet).

Connecting your Stripe account to Bumpsale

Step 2: Create your first Bumpsale!

You’re rockin’ and rollin’! We told you this was easy. With one click of your mouse, you’re on your way to building your first Bumpsale.

Create a new Bumpsale

Step 3: Set your Bumpsale settings

Next up, you’re going to fill out a couple simple fields. You can ALWAYS edit this stuff later, even while a Bumpsale is active (so don’t worry about getting it perfect). These are the fields you’ll fill out:

  1. Bumpsale Name (this shows on the purchase box that pops up for your customer)
  2. Bumpsale URL (this is so we can help you later on in case you have any trouble)
  3. Currency (135+ to choose from, the default is USD $)
  4. Starting Price (whatever you want your Bumpsale to begin at)
  5. Bump Price (how much your Bumpsale price should increase after each purchase)
  6. Highlight Color (this is the button color and the purchase box accent color)
  7. Checkout Timer (how long you want someone to lock in their price when they click the button to buy)
  8. Redirect URL* (where should someone go after they complete their purchase)

Bumpsale button Settings

*Setting your post-purchase redirect URL: Where do you want your customer to go after they finish their purchase? You don’t want them to just land back on the sales page, that’s confusing. We recommend creating a Thank You page of some sort on your website and redirecting to that page. This gives your customer a great experience AND give you a chance to lead them to the next step in the process (if there is one).

Add URL Redirect to Bumpsale

Bonus Tip: Add a way for people to share after purchasing (aka: “social intent”)

Adding social intent on your thank you page is a great way to get someone to share your Bumpsale on Facebook or Twitter. You can use Share Link Generator to make the links, then just add those to friendly share icons on your thank you page.

Use Social Intent on Thank You Page

Step 4: Add the Bumpsale javascript and Bumpsale button code to your website

You’re almost done! Grab the little snippet of javascript code and add it wherever you add other custom scripts to your website (in WordPress this is probably in your header.php or footer.php, in Squarespace this is in your “Code Injection” area within Settings). Here’s a little example of adding it to WordPress.

Note on WordPress: You DO have to publish the WordPress page/post to see the Bumpsale code in action – it will NOT work in preview mode.

Add Bumpsale code to your website!

Step 5: Create any automations that need to happen post-purchase

Bumpsale is going to handle the purchase itself, but it’s on you to give your customer whatever they just bought from you. This could simply be having your redirection URL go to a page on your website with a promo code to use or a secret link to access your product/service.

We highly recommend using Zapier for digital products (redeeming courses, ebooks, etc): You will use your Stripe account as the first step in any Zapier Zaps.

There’s a section below with Bumpsale + Zapier Tips

Step 6: Do a test purchase of your Bumpsale!

We cannot recommend this step enough. Use an Incognito Window in Google Chrome, or simply use an entirely new browser. This will give you the complete experience of viewing your sales page and your Bumpsale as a potential customer. Go through the entire buying process yourself and make sure everything works properly.

  • When you click the Bumpsale button, did it open the buying modal window?
  • When you filled out the buying form did it work?
  • When you finished your purchase, did you get redirected to the right URL?
  • On the page you were redirected to, does everything look correct? Did you add social intent? (You should!)
  • Check your email inbox, did you get a payment receipt for the purchase? (Reminder: You customize this receipt in your Stripe account settings)
  • Was any advanced stuff with Zapier supposed to happen? Did that work?
  • Go back to the sales page, did the price of the button bump up by the Bump Amount you set?

Example purchase with Bumpsale

Step 7: Promote your sales page! You’re off to the races!

Huzzzzah! It’s time to get your Bumpsale out into the world and bringing money into your bank account. Feel free to check out our tips below on setting up a sales page and things that help land the sale.

Happy after Bumpsale

(How you should feel after people buy your Bumpsale.)

Step 8: How to get your customer email addresses after your Bumpsale is done?

This one is easy! All you need to do is log in to your Stripe account, navigate to the Payments area, and click the Export button. You’ll want to select the “Default” option and you’ll find all your customer emails in the resulting CSV.

Another option is to use Zapier to automatically send your customer emails from Stripe and add them wherever you want (more on this in the Zapier section below).

Example Stripe Export for Bumpsale customers


How To Warm Up Your Audience For Your Bumpsale

Warming up your audience for a Bumpsale is incredibly important. Did we mention that enough yet? It’s likely your audience has no clue what Bumpsale is, how it works, or why you’re even talking to them about it. That’s why you need to warm them up!

Feel free to copy, paste, and customize this text which helps explain how Bumpsale works (use this in emails and on your website near the Bumpsale button so it’s very clear how it works):

Hey there! On [INSERT DATE] I’m doing something fun that I’ve never done before. I’m going to be offering [INSERT BUMPSALE PRODUCT OFFER] at a super discounted price, but with a twist!

Starting on [INSERT DATE AGAIN] at [INSERT TIME] I’ll be using something called “Bumpsale” to sell [OFFER NAME] starting at just [INSERT BUMPSALE START PRICE] and with every purchase, the price will bump [INSERT BUMP PRICE]. The earlier you purchase, the lower the price you’ll pay.

The total value of [OFFER NAME] is [TOTAL VALUE] so you’ll have the chance at snagging a crazy discount. This “Bumpsale” will only be available for [TIME AVAILABLE] so make sure to get ready as I won’t be doing this again for quite some time.

Keep your eye on your inbox for my next email that will have the link to purchase the [OFFER NAME]!


Here’s an example of how we explained a Bumpsale right on the sales page:

Vibrant Stuff Bundle How It Works

One thing to think about as well is your Bumpsale promotion schedule.

From personal experience running multiple Bumpsales, I’ve found that this schedule works really well:

Email #1: Announce the Bumpsale is coming (using the text above) a few days ahead of time

Email #2: Share the link to buy, with a clear explanation of what’s being offered, how great the discount is, and a reminder of how Bumpsale works

Email #3 (24 hours left): Remind people that the time to purchase is running out and remind them how great of a deal the Bumpsale still is*

Social media promo? If you’re promoting your Bumpsale on social media, feel free to give updates on a similar schedule!

*Recommendation: Take the current price of the Bumpsale and divide by the total value of what you’re selling. For example, if your Bumpsale is at $75 and the total value is $400 your customers are getting an 82% discount on the total price!


Bumpsale + Zapier Tips

This section is for you if you want to have some sort of automated event happen AFTER someone purchases your Bumpsale.

Example Zapier automation events:

  1. You send a nice thank you email (or an email with a password to access resources)
  2. You add their email address to your email provider (Mailchimp, etc)
  3. You get a notification in Slack that someone purchased your Bumpsale
  4. You automatically add their email into an online course and they get access
  5. And so many other things!


If you’ve never used Zapier before, it’s incredibly powerful and really easy to use. There is a free account level, but I would recommend opting for the Professional ($49/month) level DURING a Bumpsale (you can downgrade immediately after your Bumpsale finishes). Using the Zapier Professional Plan, you take advantage of the 5 minute Zap runtime, which will give your customers a good experience. You absolutely do not have to use the $49/month plan, we just find it’s best experience for a customer.

Setting up a Zapier Zap with Bumpsale (Stripe)

Bumpsale is NOT the first step in a Zapier Zap, that will be your Stripe account. After you follow the steps in the Zap creation process to connect your Stripe account to Zapier, you can choose from one of two triggers to use from Stripe:

  • New Charge (recommended!)
  • New Event
  • New Customer

NOTE: If you’re connecting a Stripe account to Bumpsale that has other purchases happening with it, you’ll need to use a Filter step in your Zapier Zap to look for the name of your Bumpsale in the purchase data. More on this in Zapier Tip #3.

Setup Stripe in Zapier for Bumpsale

Zapier Tip #1: Set your customer’s expectations (if using Zapier to trigger an action)

On the Thank You page, or wherever you redirect someone after a successful purchase of your Bumpsale, make sure you mention that it can take 5-15 minutes to receive whatever you’re triggering via Zapier (an email, etc).

Zapier Tip #2: Send a thank you email via Zapier (using Email By Zapier)

One of the simple triggers after a successful purchase of your Bumpsale is to send an email using the Email By Zapier action. In this email you can add your product redemption itself (maybe a link to a page or a password), or you can simply say thank you and let the customer know what to expect next now that they’ve purchased.

Reminder: Stripe will send a receipt after purchase, so you do NOT need Zapier to send a receipt of any kind via email.

Heads-up: The “Email by Zapier” can only send 10 emails per hour (yep, 10). If you know you’ll have more than 10 sales per hour, you’ll want to use a different way to send an email. Maybe it’s a 1-email sequence people get added to in your Zap?

Email By Zapier for Bumpsale

Zapier Tip #3: Use a filter if your Stripe account has other purchase activity going on

If you currently use your Stripe account to sell any other products at the same time you’ll be running your Bumpsale, you’ll need to use a Zapier Filter to make sure your Zaps only run when the Bumpsale is purchased (and not all products associated with your Stripe account).

After your Stripe account is connected, the Zapier Filter step will give you an option of Only continue if…

Only Continue If in Zapier for Bumpsale

In the first input field, look for the entry that has the name of your Bumpsale.

In the second input field, select (Text) Exactly Matches.

In the final input field, type your Bumpsale name exactly as it’s named in Bumpsale.

This will ensure that every Stripe purchase Zapier sees associated with your Stripe account, the Zap will ONLY run if it meets the Filter requirement.

Important: If you’re only using your Stripe account for your Bumpsale you DO NOT need a Zapier Filter.

Zapier Tip #4: Add whatever steps you like to make your automated tasks happen!

The additional steps in your Zapier Zap will be up to your choosing. Again, you could add your Bumpsale customer to your email list, or immediately add them to your online course, etc.

You do NOT need to make multiple Zaps if you want multiple actions to happen after a Bumpsale purchase. In one single Zap, you can:

  1. Send the Email by Zapier
  2. Add your customer’s email address to your email list (ex: Mailchimp)
  3. Add your customer to your online course
  4. Send yourself a Slack notification of a new purchase (this is just fun!)

All of those would be Actions within the one Zap you create. Yay, you!

Final Zapier Tip: Make sure your Zaps are turned ON!

You’ll want to double-check that your completed Zaps are turned on and ready to go. You can triple-check this by completing a real purchase of your Bumpsale and seeing if the Zap fires in your Zap History. Remember, it can take 5-15 minutes depending on whatever Zapier pricing plan you chose.


Last But Not Least, Frequently Asked Bumpsale Questions (FABQ)

👉 How come multiple people can pay the same price if it’s increasing after each purchase?

If you have a large audience, odds are you will get a handful of people who pay the exact same price for your Bumpsale. I’ve had this happen multiple times and it’s simply a byproduct of having a larger, engaged audience (that’s a great problem to have!)

Your Bumpsale button will automatically bump the price as insanely fast as possible after a purchase happens. But… if someone clicked the Bumpsale button and they’re looking at the purchase pop up window, that customer’s price is locked in until the Bumpsale timer expires.

Bumpsale Price

Even if you have multiple customers pay the same price, Bumpsale will keep track and update the button with EACH purchase (regardless if the same price was paid or not). Example: If your Bumpsale button is at $20 and 5 people click it at the exact same time before another purchase happens, each time one of those 5 customers completes their purchase the Bumpsale button on your sales page will increase based on your bump price setting.

We do NOT recommend setting the Bumpsale timer to anything less than 180 seconds. It can take a minute or two for people to fill out their payment information. You’d rather have happy paying customers, than angry customers who had a buying window close on them and they missed out on the price they were looking at.

👉 Does Bumpsale create my sales page for me?

Nope. Bumpsale is just the button and the purchasing mechanism. You’ll need to create your own sales page and add the Bumpsale javascript and Bumpsale button code to your own website.

👉 I’m not a CSS expert, do I have to use the CSS provided in the Bumpsale installation instructions?

We would highly recommend at the very least copying + pasting our Bumpsale CSS and adding it to your website. Otherwise, your Bumpsale button is going to look pretty crappy. Odds are you know someone who knows CSS and they’d be willing to help you for the price of a beer or cup of coffee.

👉 Does Bumpsale bring customers to my sales page?

We wish! You bring the customers to your Bumpsale. I’ve personally seen amazing results using the social intent on a thank you page after a Bumpsale purchase. Don’t be shy in asking someone who just bought from you to share that they purchased (because hey, how the heck often do you run a Bumpsale??)

👉 Can a Bumpsale button expire after a certain number of purchases or certain amount of time?

It cannot. While Bumpsale is smart, you’ll have to be the one to turn it off. And by turn it off, we simply recommend removing the button itself from your sales page. There is nothing that needs to be done in Bumpsale itself to “end” a Bumpsale.

👉 Why only Stripe? Why not PayPal?

Guh, PayPal just sucks. It’s an awful experience. For years we’ve tried to get PayPal added and it’s a huge thorn in our side. Eventually, we’ll support PayPal, but Stripe makes everything sooooo smooth and simple.

👉 How long should I run my Bumpsale for?

Again, we recommend a shorter time period for your Bumpsale. Anything over one week is pretty long and the urgency built into using Bumpsale kind of wears off. We recommend running a Bumpsale for a minimum of 24 hours and a maximum of 5 days. But hey, if you want to use it for longer than that, it’s completely up to you!

👉 If I have trouble with Bumpsale who should I contact?

Ghostbusters! No? Send an email to conrad (at) and jason (at) We’ll happily answer any questions you have!


8-Step Guide to Becoming Debt Free (How We Paid Off $124,094)

June 21, 2018


Our Debt Journey And How We Can Help You Become Debt Free

A few years ago my wife and I found ourselves overwhelmed with debt. How much debt? $124,000 spread across six credit cards, a car loan, and student loans. We could never have imagined being debt free at that time.

This article shares our debt story, but more importantly shares our debt payoff plan: the exact steps we used (and that you can use) to become 100% debt free in just 15 months!

Before we dive in, I want to be absolutely clear that we didn’t get into overwhelming debt overnight and we didn’t get out of our debt overnight.

Our debt didn’t come from buying extravagant things. The majority of our debt came from a business I ran from 2009-2013. I got behind on the monthly operational costs, things like employee salaries, design and development expenses, advertising and marketing, and countless products and services that kept my business running. Then we had my wife’s business debt, her student loans, and our car loan.

These were our specific debts and where they came from:

  • Jason business debt: $72,328
  • Caroline business debt: $6,764
  • Caroline student loans: $20,208
  • Volkswagen Tiguan lease payoff: $24,794
  • Total debt: $124,094

I want to point something out before I move a step further, and my guess is you can relate to what I’m about to say.

I was ashamed of our debt. I was embarrassed by the financial mistakes I’d made. Becoming debt free felt like an insurmountable mountain to climb. If you’re currently battling with debt and having similar feelings, those feelings are completely normal.

Get out of debt

Debt is something almost all of us deal with

Did you know the average credit card debt per U.S. adult, excluding zero-balance cards and store cards is $4,878*?

How about the fact that 26% of small business owners carry a balance of nearly $10,000 on their business credit cards*?

Or did you know that more than 35% of Americans are seriously concerned about being able to meet essential financial obligations such as their mortgage, loans, credit card, or bill payments*?

Some of us are riddled with debt, stuck in its invisible grasp with no sight of escape. Some of us just have school loans, which seem harmless because of low fees and payments, so we ignore the soul-sucking and bank-account-syphoning elephant in the room. Some of us are able to use debt to our advantage to escape a bad month of business or get through hard times. But debt is dangerous and it needs to be dealt with head-on.

Let us help you attack your debt, just as we attacked and vanquished ours!


Step #1: Your debt payoff starts here

Draw Your Line In The Sand Right Now

Around 2013 I realized our total debt was over $120,000. That was the moment when I knew something had to change.

Unfortunately, that change came with the tough decision of closing my business’s doors. That meant letting people go, cutting as many expenses as possible, and accepting the fact that my business was no longer profitable and was failing.

I hope, for your sake, that $120,000 is not your number. I hope it’s a drastically lower number. But if you do have more debt than we did, don’t be ashamed of it any longer. It’s just a number.

Make today the day you announce you aren’t getting any further into debt. Draw your line in the sand right now.

Changing how we viewed our debt was a crucial first step to becoming debt free

It would have been easy to let the feelings of shame and embarrassment continue to control how we felt about our debt. We could’ve given in to those feelings as we’d been doing and as a lot of people do, but instead we decided to do something different.

Bear with me, as I know this is going to sound weird, but we started to think of becoming debt free like playing the original Donkey Kong video game:

  • We were Mario, with a difficult path ahead of us
  • The barrels, oil, and fire were our current debt hurdles (credit cards, loans, etc)
  • Donkey Kong was consumerism trying to keep us in debt
  • Saving the princess was financial freedom!

This Donkey Kong metaphor may sound completely bizarre to you, but it really helped us shift how we thought about our debt. It went from a dark cloud that loomed over our heads, to a silly game we could try to beat. With each ladder we climbed and every barrel we jumped over, we’d be getting that much closer to rescuing the princess (AKA gaining financial freedom).

Whether you want to buy into our Donkey Kong metaphor or not, maybe there’s a way you can reframe how you think about your debt? The most important thing at this point is to draw your line in the sand and to tell yourself: I WILL GET OUT OF MY DEBT!

TIP: A great thing to help draw your line in the sand is to have someone hide your credit cards so you can’t have access to them. Or just cut them up. Start using a debit card or cash only.


Step #2: Consumerism is your enemy

Change Your Mindset About Credit, Credit Cards, and Buying Things

We’re a society driven by consumerism.

Turn on any TV. Open any magazine. Browse any website. Scroll through any feed on your phone. There’s a new gadget or clothing company begging you to spend money you don’t have. Today is the day you tell yourself you don’t need to buy any more stuff.

“I don’t need to buy XYZ thing. I want it, but I don’t need it.”

How many things have you purchased with your credit card(s) in the past year that you can actually name off the top of your head?

If you can’t remember what you spent your last couple thousand dollars on, it wasn’t that important and you didn’t actually need to buy it.

What’s more important in your life: Owning a couple new material goods, or NOT being stressed out over your current financial situation?

Credit cards points and consumerism are not your friends when you’re deep in debt

Commercial after commercial tells us that the credit card companies just want to help us! They want to give us nice low rates (which most of us can’t actually qualify for) and they want to reward our spending by giving us awesome perks (redeem those double points!).

Except, when you’re in debt, the last thing you should be thinking about is credit card points. One of the important mindset shifts in becoming debt free is greatly reducing your spending. I’ll talk more about reducing spending in a moment, but credit card companies are great at convincing us that “cash back” feels like we’re somehow saving money. Or that “airlines miles” will help you travel for free. If you’re in debt, getting minuscule amounts of cash back or accruing airline miles are thoughts you need to put on hold.

At one point my wife and I had 12 active credit cards and the majority of them were opened because of the so-called “rewards” they offered. Here are a couple of examples, along with the rewards we never actually enjoyed:

Best Buy Rewards Card – A simple VISA card that helped us purchase electronic goodies. Except, when we bought them with Best Buy’s friendly payment plans, we didn’t take into account we’d up spending 20-30% more on the items we purchased because we could only ever afford to make the minimum monthly payments.

Southwest Airlines Card – I remember the day I signed up for this card and thought I’d grab the reward offer of a free companion pass for Southwest flights. Within a month I’d met the qualifying spend of $3,500 on the card, except, I didn’t have the money to pay it off. You don’t get the free companion pass if you don’t pay off required spend. Not only did I not get a stupid free companion pass, I now had $3,500 of debt that probably didn’t need to exist. (Also, FWIW, I can count on one hand the number of Southwest flights I’ve taken in the past decade, we never fly with them.)

CitiBank Diamond Preferred Card – This was a card I signed up for because it would 2x or 3x your points depending on what you purchased. It took me six months to realize I could only ever use those points for stuff I didn’t need (like a blender, or headphones, or other consumer goods that I already owned or absolutely didn’t need).

I hope these examples help you take a look at the cards you currently have in your wallet/purse. You may think these credit card companies are trying to help you, but they’re not. These companies have very well crafted systems in place to keep us all in debt.

TIP: Stop using credit card points cards until you’re completely debt free. When you’re debt free, start to identify one or two credit cards that offer rewards you might actually use.


Step #3: Spend less and/or earn more

The Are Two Ways To Get Out Of Debt: Spend Less or Earn More

The un-sexy secret to getting out of debt is exactly the headline you just read: Spend less money or earn more money.

Sure, there’s a lot more to becoming debt free (hence the length of this article), but along with acknowledging your debt and avoiding consumerism, this is the next mindset shift that will help you get rid of debt.

Spending less money

Getting rid of a mortgage and renting a home

I could write an entire article on why buying a home is a terrible financial investment for the majority of us. Instead, I’ll let the economic crash of 2008 do the talking for me. I would, however, like to explain how renting a home (AKA “throwing money away”) was incredibly helpful in our journey to financial freedom.

When you have a home with a mortgage, as we did for 8 years, you do NOT have stable expenses. In fact, most homes are a ticking financial time bomb.

What do I mean by that? Oh, how about when your air conditioner breaks and you have to spend $8,000 to get it replaced? Or how about when you wake up one morning to an inch of water in your living room, only to find out you had a “slab leak” which still cost you $2,000 (after insurance!)? Or how about the $20,000 “invested” in redoing the kitchen and bathroom which was never actually recouped. Not to mention every stupid little thing that pops up and needs to be fixed (and paid for) when you own your own home.

Deep breath Jason, deep breath.

When my wife and I moved from Florida to California and chose to become renters, we knew one very important thing: Renting gave us the piece of mind that we’d incur $0 in surprise costs when it came to our home.

As renters, we’d never have to worry about an $8,000 air conditioning system. We’d never have to worry about little costly odds and ends. We would pay our rent every month and that was it. If something went wrong, it was on our landlord’s dime. Every dollar we used to have to spend to cover unexpecting home costs could now go toward aggressively paying off our debt.

Renting can be the best thing for people who are in debt. It’s a completely predictable expense every month, and you are guaranteed NOT to lose money in the long run.

A home you buy? Not an investment to be made when you’re trying to get out of debt. Heck, we’re years removed from being in debt and we still (proudly) rent our home.

Sacrificing a 15-year passion: Cars

I want to share a more personal example of spending less money: For me, that was a 15-year passion of owning nice cars.

I love cars. LOVE them. They’re easily the biggest money-pit I’ve had besides my business. Except, unlike my business, there is no potential ROI (return on investment) for a car. Sure, a 1950 Ferrari Dino is a great investment, but let’s be realistic here, you and I are not collecting Ferraris.

Aside from our mortgage and food, my monthly car payment was always our highest household expense. Over the years I had car payments ranging from $500 per month to as high as $1,200 per month—the latter being the time when I needed to own a Porsche Cayenne Turbo as a 25-year-old (dumb, dumb, dumb). Not to mention all the extra hidden costs of cars like gas, insurance, maintenance, etc.

When we decided to attack our debt, I knew my “fun car” hobby had to take a back seat (get it? It’s a car pun folks!). My wife and I talked about this decision together and I made the commitment to our get-out-of-debt plan that we’d purchase an affordable car and be more responsible when it came to spending money on depreciating assets (cars). We ended up leasing an extremely practical Volkswagen SUV, a car that would be very low in maintenance costs, yet not feel like we were driving a 1982 Ford Taurus.

I’d be lying to you if I said I loved driving that VW. Truthfully, I loathed it. It wasn’t a bad car by any means, but it was quite the departure from the BMW M5, BMW M3, Porsche Cayenne, Infiniti G35, etc, I was used to driving. But I just had to keep asking myself: “Do I want to feel cool driving around in a nice car, or do I want to save the financial princess and stop having a looming cloud of debt over my head?”

What you own right now is ENOUGH

Think of spending less as short term pain, for long term gain.

I really hope this point settles in with you. Your current TV, couch, bed, car, etc, are all enough right now. They are good enough and will do the job you need them to do until you become debt free. If you can commit to making short-term sacrifices and not focus on upgrading anything in your life, you can make huge dents in paying off your debt right away.

You are spending less now so you regain control of your finances. It will be uncomfortable to change your lifestyle and remove lavish things from your life, but I can tell you from firsthand experience: the feeling you get from paying off all your debt is a lasting positive feeling that greatly outweighs the short-term blips in happiness you get from buying stuff.

Earning more money

Now that I’ve gone over the spending less part, let’s talk about earning more money with two specific examples.

Let me start off by saying that I realize earning more money is not easy. If you don’t own your own business and you work at a conventional 9-5 job (for someone else), it can be difficult to think about earning more money. I do want to tackle both scenarios though, as I believe it’s possible to earn more money whether you work for yourself or you work for someone else.

Earning more money when you charge by the hour (hello freelancers!)

I’d like you to meet my wife Caroline, she’ll be taking over the keyboard here for a moment to share her story of earning more with her business:

Hi y’all! Caroline here, Jason’s better half (obviously!)

When I was running my own branding design company in 2014 I had a stunning realization: Quite simply, I wasn’t making enough money.

I think this problem can take different forms for different businesses – not enough clients/customers, prices too low, terrible margins, etc. In my case, I was taking on far too many small projects for far too little money. $100 here for a hand-lettering project, $200 here for a small graphic design job, giving deals to friends and not being more vocal about the real amount of time a job would take. Then, when I had bigger branding design projects, I was working way more hours than I was charging my clients. Something had to change.

Jason and I sat down and starting talking about how I was running my business and where we might be able to make improvements (you know, make more money!) As we started talking it became clear that with any service-based business (AKA freelance), time truly is money. If it took me two hours to finish a job that could have taken me one hour, I just lost an opportunity for additional revenue. And if I had a bigger job that I only charged the client for 40 hours of work, but it took me 80 hours, I just missed out on a ton of revenue.

To give you an idea of just how much money I was losing out on, after implementing a simple time-blocking exercise (which I’ll explain in a moment) I was able to TRIPLE my revenue! Not only was I able to earn more money, I gained more time back because I became extremely diligent with how I was spending it on a day-to-day basis.

What is time-blocking and how did it help me triple my revenue?

Jason and I looked at a normal work-week for my branding design business and figured out a few simple things:

1. I did my best work between 11 am – 4 pm each day (5 hours of work per day)
2. Working Monday – Friday, I had 25 billable hours
3. Over the course of 4 weeks, working at $75/hour, I should be making $7,500 per month (25 hours a week x 4 weeks = 100 hours x $75 = $7500)

Seeing that $7,500 was defeating and empowering at the same time. I certainly wasn’t making $7,500 a month (I was lucky to be making $2,000 per month), but seeing how just 5 hours of focused work per day could generate so much more revenue for my business was incredibly motivating.

From that meeting with Jason, I started to block off time on my Google Calendar with client work. Whether it was a tiny 1-hour project, or a bigger 80-hour project, all of the working hours I committed to would go on my calendar and I would do my darndest to ruthlessly stick to the time I’d estimated. This time-blocking system gave me clarity in my work days and was a great way to understand how much my time was worth.

As I mentioned earlier, getting a grip on my hours, estimating my time better, and working during specific time blocks helped me triple my revenue in just a few short months. If you’re a freelancer (or you work for yourself), time is money and you should definitely keep track of it.


Working part-time on a side project can also help you earn more

You thought that Caroline might be passing the writing-baton back to me, but she has another story to share with you about earning more money. This example specifically applies to you if you work a full-time job and don’t think you can earn more money.

It’s Caroline again, I’m back on the keyboard!

If you would have told me that I could make an additional $3,000 per month in revenue with a project I did on the side, I wouldn’t have believed you. If you read the last few paragraphs then you know I was doing branding design as my full-time job. Now, I wasn’t working for someone else in a 9-5 capacity, but the story I’m about to share happened in my “off work” hours.

Whenever I wanted a break from my client work, I would open up a sketchbook and start doodling. I didn’t consider myself an artist, but I enjoyed filling blank pages with drawings and hand-lettering. For months I filled sketchbook after sketchbook, not at all thinking I was honing a skill that would lead to earning more money, I simply enjoyed the creative outlet.

I started sharing some of my hand-lettering creations on my Instagram account and people started asking where I learned how to do hand-lettering. I responded in truth, I hadn’t really learned it anywhere, I just started doing it in my spare time. When enough people asked me about my hand-lettering, I had the spark of an idea: I should write a blog post that explains the basics (that I’d learned) of hand-lettering. Just a really simple guide if someone wanted to go on a hand-lettering adventure of their own.

That blog post started to get a little bit of traffic. Then it started to get shared on Instagram and Pinterest. Before I knew it, hundreds of people were reading my introduction to hand-lettering post and I saw an opportunity. I added an email capture to the blog post that asked people to enter their email if they’d be interested in an online course about hand-lettering (I’d never made an online course, but Jason had, and it seemed like something I could create if there was interest).

After a month I had over 500 email subscribers waiting for me to create a beginner’s hand-lettering online course! I hunkered down one weekend and created my first online course, without grand expectations about how it would sell. I worked on the sales page for the course and some other odds and ends in my non-working hours, and a few weeks later I launched the course. I was happy to make a few hundred bucks from the small email list and decided to change the callout on my blog post from “sign up to my email list” to “purchase my beginner’s course to hand-lettering.”

All of the sudden I was waking up to course sales. Then the traffic to the post would increase and I’d see more sales. Day after day, week after week, month after month, the sales steadily increased and I’d created my first passive income source. In the first two months that hand-lettering course generated over $7,000 in additional revenue I never saw coming and over $82,000 in total revenue!

The best part about the extra money I earned was that it happened on the side of everything else I was doing. It didn’t take an extraordinary amount of effort or time, I just saw an opportunity to create something and there was a demand for a quality hand- lettering resource for beginners.

I share this with you because I want you to realize what is possible. I want you to feel the way I felt when I made my first online course in my spare time and it started making passive income.

There are so many opportunities waiting to be had out there. You just have to find the drive and the commitment to make them happen.

Hopefully, after reading those two stories from Caroline your wheels are turning on how you might be able to earn a bit more money. And maybe after reading how we starting renting our home and I gave up a passion for cars, you’re already thinking about ways you can cut back on larger expenses you don’t need (for the time being, so you can become debt free!)

TIP: Grab a notebook and jot down a couple ideas of how you might be able to make more money right now: Is it using time blocking? Or creating a small product in your spare time that you’re interested in? Also, write down larger expenses that you may be able to cut back on.


Step #4: Get control of your expenses

It’s Time To Look At Every Dollar You Spend (And Find Hidden Money)

Have you ever logged into your online banking or your credit card company, only to realize it’s kind of a pain in the ass to figure out how much money you’re actually spending? Sure, you can see your expenses in a vertical list with a total balance (usually always decreasing, ugh!), but banks and credit card companies don’t try to help you see where you can save money or cut costs.

It’s time for you to take control of all your expenses, and get a firm grip on every dollar you spend and make.

There’s a simple exercise that my wife and I did that opened up our eyes to our spending: We exported the last three months of activity on our bank accounts and credit cards, put them in ONE spreadsheet, and did our best to organize them by spending category (separated by month).

We called this exercise ETAC (or Expense Tracking and Categorization)

The silly thing about the name ETAC, if you say it out loud it kind of sounds like you’re saying attack. Which is neat, because you want to be attacking your debt!

Anyhoo, here are the simple steps for the ETAC exercise (video walk-through below):

  1. Download the past three months of spending for ALL bank accounts and credit cards (CSVs)
  2. Import your downloaded CSVs as individual sheets
  3. Format your data so it’s all uniform
  4. Once your data is all formatted, add every transactions to “All Transactions” sheet
  5. Sort “All Transactions” by month
  6. Assign a category to every transaction (use our examples or create your own)
  7. Sort “All Transactions” by month
  8. Filter transactions by month, and then sort by category
  9. Use formulas to sum the expense total for the month in each category

Expense Tracking and Categorization (ETAC) Spreadsheet

📊 Click here to use the ETAC spreadsheet.

We encourage you to save yourself time and use our example Expense Tracking and Categorization spreadsheet with the categories we use to organize our expenses. If you’re creating your own spreadsheet, here are the categories we use and recommend:

  • Auto (car loan, maintenance, gas, etc)
  • Business (any costs associated with running your biz)
  • Eating Out (coffee, romantic dinners, fast food, etc)
  • Entertainment (movies, drinks with friends, bingo night, etc)
  • Groceries (food!)
  • Health & Personal Care (therapy, Dr’s visits, etc)
  • Insurance (health, auto, dental, etc)
  • Misc (whatever is left!)
  • Pets (pet emojis!)
  • Rent/Home
  • Shopping (Target runs, IKEA, Amazon, etc)
  • Travel (weekend trips, et al)
  • Utilities (electric, water, trash, etc)

The reason these categories are so important is two-fold:

1. You want to compare the category month over month and see if there are any big spikes and what your current monthly average spend per category is (this is how you can find where to spend less).

2. Later on, we’ll show you how to create an ongoing monthly budget for these categories, so you can be a wizard at tracking exactly where your money goes and have ZERO financial surprises (you know, like barrels thrown by a digital monkey).

I cannot stress the importance of the Expense Tracking and Categorization (ETAC) exercise enough! Even if you think you have a good idea of what you spend, I 10000% guarantee listing out and organizing all your expenses will surprise you.

NOTE: If you have spouse or family member, this is a great person to do this exercise with. You’ll probably be embarrassed to show them your expenses—but you know what—that’s a huge red flag that you NEED to show someone your finances!

Here’s where we found hidden money in our expense tracking exercise

When my wife and I organized our expenses for the first time, a few items within categories of spending jumped out as potential places to save money (and put towards our debt).

Cell phone bill (I found $1,440 in annual savings!)

We were paying $260/month for our “family” cell phone plan. We’d had the same (unlimited) plan for more than two years and I had a hunch there was a better plan available. I went into an AT&T store (gasp! I know!) and asked them if they had a better option based on our actual phone usage. Come to find out, we were only using around 8GB of total data and didn’t need the costly unlimited plan. We switched to a $140/month plan and netted $1,440 in annual savings.

Cable bill (I found $600 in annual savings!)

At the time of doing our first ETAC exercise, we were paying $185/month for all bizallion cable channels (that we only watched a small handful of). Back in 2014 cutting cable wasn’t as prevalent, so I didn’t think about that as an option, but I did think maybe I could call the cable company and simply ask for a better plan since I had been a loyal customer for years. I navigated my way through the painful customer support phone tree and was able to reduce our bill to $135/month, saving us $600 per year.

Entertainment (I found $1,800 in annual savings!)

Drinks with friends, seeing movies (and getting popcorn), two Netflix subscriptions in one house, and a bunch of other stuff quickly filled this spending category without us even noticing. We decided we’d set some boundaries for our entertainment and hopefully save money. We allowed ourselves to see two movies (in the theater) per month and have two nights per month to have drinks with friends. Setting these boundaries saved us $150 per month or $1,800 per year. Remember, Short term pain for long term gain!

Food (I found $6,000 in annual savings! Whaaat?!)

We were spending $2,000 per month on food ($1,400 was eating out). For two people that is a lot of money each month! However, neither of us love to cook and because we work from home, going out to eat is one of the nice breaks from our day-to-day routine. That being said, we challenged ourselves to cut back by $500 and only spend $1,500 per month going forward (this included eating out and groceries). That $500 added up quickly, saving us $6,000 (!!) that we could put towards our debt in one year!

Just by reassessing a few categories of our spending we were able to find nearly $10,000 we could apply to our debt!

Do a little bit of cutting back in the short term and you’ll find hidden money you can apply to pay down your debt. You’ll be amazed at how living frugally for a short time can help get you out of debt exponentially quicker.

TIP: Don’t waste any time, do the ETAC exercise today and categorize all your spending for the past three months. Where can you find hidden money?


Step #5: Get your income in order

Paying Off Debt Requires Looking At Your Income Flow

The one thing that stood out to us, and that would become critical to our success in our war on debt, was building a better income flow.

If you’re anything like we were a few years ago, you deposit money into your bank account, you pay your credit cards from your bank account, and there’s not much else to it. There’s nothing inherently wrong about this, but there is a better way!

Creating an income flow will help show you a more logical and systematized process for managing the flow of your money (in and out of your accounts).

Here’s what we did to create our income flow:

#1 Established our bare minimum monthly household expenses

After doing the Expense Tracking and Categorization exercise, we had a bunch of categories of spending that we could total up to see our average monthly budget. We took every category except our business expenses, added them up, and that became our minimum monthly household expense number.

#2 Established our bare minimum monthly business expenses

Similar to the household expenses, the category from our ETAC exercise that grouped our business expenses together showed us our average monthly budget for business. Keeping this separate from household expenses is helpful if you have a bank account specifically for your business (which, if you work for yourself, you should!).

#3 Created a monthly schedule for transferring all excess income to a new account

It should go without saying that you need to be making more money than you’re spending every month. If this isn’t happening for you right now, you have a bigger problem at hand. Hopefully, after going through the ETAC exercise, you have some excess income that you can apply to your debt (especially if you found hidden money!). For us, we identified the excess money we made over our expenses every month and would transfer this to an external savings account to be applied toward our debt (more on this savings account in a moment).

#4 Scheduled a weekly budget meeting

Weekly budget meetings helped us deal with the shame and embarrassment of our debt.

This may sound crazy to you, but my wife and I decided to put a standing meeting on our calendars every week to start talking about our finances. This meeting would involve doing a couple things:

  • We’d download the previous week’s expenses and track/categorize them
  • We’d discuss the previous week’s expenses and go over any outliers
  • We’d discuss our income for the week
  • We’d look at our debt payoff schedule (more on this in a minute)
  • We’d make transfers from our business accounts into our household account
  • We’d make excess cash transfers to an external savings account
  • We’d pay down or pay off any debts we could

I could talk for hours about how vitally important these weekly budget meetings were for us (and continue to be). Not only did they help us get a firm grasp on our financial situation, but they also helped us deal with the shame and embarrassment of our debt. The more we discussed and attacked our debt every week, the less shame and embarrassment we felt about it.

If you don’t have a spouse to do weekly budget meetings with, find one! Just kidding… But ask a friend? Get a financial advisor? (More on the latter option in a bit as well).

#5 Set goal numbers of how much debt we could pay off each month (debt payoff schedule)

I’ll get into much more detail about this in Step #7 of this article. But the idea is to look at how much excess money you have above your expenses that you can immediately apply to your debt. Some weeks it may be $50, some weeks it may be $0, and some weeks it may be $500. The key is to continually know more information about your financial situation based on your income flow.

Our example income flow

Creating an income flow isn’t rocket science, and I felt like we already had some semblance of a household budget, but using this new process was incredibly helpful. Our income flow consisted of these things:

  1. Caroline’s business checking account (Caroline Biz)
  2. My business checking account (Jason Biz)
  3. Household checking account (Household Account)
  4. External savings account (Debt Crusher!)

Income Flow

The most important part of our new income flow: Debt Crusher (savings account)

When all your bank accounts can be seen on the same online banking dashboard page, it’s easy to see the money in one account as money available to any account. It wasn’t until our financial advisors introduced us to creating a completely separate external savings account (with a completely different bank) that we understood how important this was.

Our new savings account was nicknamed our “Debt Crusher” because that was its sole purpose for existing. We would transfer our excess cash from our Household Account (or sometimes Biz Accounts) and make debt payments from the Debt Crusher account.

Having a completely separate bank account that we couldn’t see next to our business and household bank accounts really helped us build momentum in paying off our debt.

No longer did excess money sit in our main bank accounts where it could easily be spent. That excess money got transferred to an account with one important job: Crushing debt!

Assign goals to each part of your income flow

Have you ever had a month where you realized you didn’t have enough money in your bank account to pay your electric bill? Maybe you’ve overdrafted a time or two and cursed yourself each time it happened? We’ve been there!

When you create your own income flow it’s extremely beneficial to add goals to each section. Our financial advisors gave us the sound advice to keep a goal amount of money in all our accounts as a buffer to never drop below (this helps avoid those crappy overdrafts!) I’m sharing our example numbers to give you an idea of how to set this for yourself…

  • Caroline Biz: Goal to have $1,500 in account at all times
  • Household: Goal to have $8,000 in account at all times
  • Jason Biz: Goal to have $3,000 in account at all times
  • Monthly transfer goal from Caroline Biz to Household: $2,500
  • Monthly transfer goal from Jason Biz to Household: $10,000
  • Monthly transfer goal from Household to Debt Crusher: $4,500

For Caroline Biz and Jason Biz, our goal number was at least one month of average expenses. The idea was to never drop below that number again if we could avoid it. For Household, our goal number was also one month of average expenses.

And if you’re wondering, YES, we had to work our way up to these goal numbers. When we first set these goal numbers we did NOT have those amounts saved in each account.

Income Flow Chart

This income flow exercise showed us that we should be able to pay down $4,500 of our debt every month (that was $54,000 in a year!). At the end of each month, we’d look at our debt payoff sheet (again, coming in Step #7 of this article) and pay down the different areas of our debt.

We didn’t always hit our exact $4,500 number, but it was extremely helpful and motivating to have a goal to hit each month.

TIP: Create an income flow of your own! Add goals for all your accounts, transfers, and get a clear picture of how much money you can apply to your debt every month.


Step #6: Your simple debt payoff plan

The 4-part Simple Debt Payoff Plan You Can Stick To

There’s a reason why this article didn’t start here. It may seem like the “plan” should’ve been first, but what my wife and I realized through our journey to debt freedom was that we needed to get all our financial ducks in a row BEFORE we started climbing ladders and dodging barrels (yep, still running with the Donkey Kong metaphor, folks!).

Truthfully, you already have a big part of your debt payoff plan if you’ve done the Spend Less/Earn More, ETAC, and Income Flow exercises. But, let us show you four additional pieces to your debt payoff puzzle based on our experience paying off our $124,000 in debt.

Debt payoff plan part #1: Short-term pain for long-term gain

Yeah, yeah, I’ve said this phrase multiple times, but it’s such an important mindset shift that you need to make when it comes to getting out of debt.

To remind you, we didn’t accrue our $124,000 in debt through lavish spending. However, do admit that our financial habits weren’t the best and there was plenty of room for improvement. A huge part of that improvement was setting budgets and sticking to them.

You cannot and will not get out of your debt if you continue to stick to the same financial habits you’ve had up until this point. You have to make changes.

The phrase that we came up with and that was a guiding principle over and over again while making sacrifices to get out of our debt was: Short term pain for long-term gain.

When we finally accepted the fact that cutting back for a few years didn’t mean cutting back FOREVER, it created a spark of momentum. Yes, we’d have to spend less money each month, travel less each year, and watch our dollars much closer every week, but those things would lead to removing the dark cloud of debt that hovered above our heads.

We want the same thing for you! So… say it with us: Short term pain for long-term gain.

Debt payoff plan part #2: It’s time to make difficult phone calls

Did you know that American Express has a hardship case that will lower your credit card interest rate (APR) to 0% for three months, 1% for the next 3 months, and then 9.99% for the 6 months that follow? All you have to do is call the number on the back of your American Express card and ask to talk to someone about a “hardship case.”

Hardship cases are made for people like you and us. We got into debt, it sucked, and we were worried about how we’d be able to afford the minimum monthly payments on our credit cards with how high the interest was on our cards. Credit card companies would rather lower your monthly interest rate (APR) then see you default on your payments (AKA: not give them your money).

I didn’t know a hardship case existed when I called American Express and was simply looking for any way to reduce my 24% APR. I hopped on the phone with a customer support person and explained my business was going through hard times and instead of defaulting on my payments, I was hoping there was some other option for me. That’s when the customer service person explained they had a program that would freeze all spending on my card, but would lower the monthly interest rate from 24% down to 0% for three months (then raise it to 1% the next three months, then raise it to 9.99% for the next six months).

These phone calls suck, but staying in debt sucks much worse.

If you apply for American Express’s hardship case, they do have to lock your cards during that time period. This sounds scary, but you shouldn’t be using your cards anymore anyway.

We also called the companies where we had other credit card balances with high APRs: CitiBank, Wells Fargo, and another American Express card. CitiBank and Wells Fargo didn’t have a hardship case like American Express they were both willing to lower our APR by over 10% on each card.

We spent just over an hour making these humbling phone calls to our credit card companies and were able to get our interest rates lowered to a point that would save us $400 in credit card fees each month.

That’s $4,800 annually, which when you add in the savings from our Expense Tracking hidden money we found, it meant we had nearly $15,000 to pay toward debt!

Ready to call your credit card company(ies) yet?

Note: We didn’t call our mortgage or student loan company to find out if they offered a hardship case of any kind. You could call and ask, it definitely wouldn’t hurt.

Debt payoff plan part #3: Move credit card debt to 0% APR cards

One of the craziest things I’ll never understand is that even when we were riddled with credit card debt, we could still get approved for additional credit cards! Insane.

Our financial advisors were happy with the hardship cases we were able to get with a few of our credit cards, but on some of them, the APR was still too high. They recommended we apply for cards with 0% APR and very low balance transfer fees. The idea is that we’d transfer the balance of an existing credit card with a high interest rate to a new card with a 0% interest rate and just pay the one-time balance transfer fee.

Here’s an example of exactly how we did this:

Step 1: I applied for the Discover It credit card (0% APR and 3% balance transfer fee)

Step 2: I got approved for the card with a line of credit of $12,000

Step 3: I transferred the balance of our Wells Fargo Platinum card to the new Discover It card ($12,000 balance x 3% transfer fee = $360 one-time balance transfer fee)

I repeated this process and signed up for the Chase Slate credit card, as they also offered a 0% APR. We moved over three separate cards that had over $9,000 on them and nearly 30% APR.

This part of the debt payoff plan is going to be dependent on your credit score and credit history. We were fortunate that we both had pretty great credit scores and credit history and could still get approved for new credit cards with reasonably high credit limits. If you can’t get approved for new cards, don’t worry, just skip this part of the debt payoff plan.

Note: We found the best 0% APR credit cards by checking out NerdWallet. They keep an up-to-date list and give you an easy way to apply. IMPORTANT: Be very careful when signing up for more credit cards, remember these are only for transferring your debt, not to use for spending!

Debt payoff plan part #4: Pay off high interest cards/loans first

You should aim to pay off the credit card or loan with the smallest balance AND highest interest rate first. As Dave Ramsey (“America’s trusted voice on money”) says, paying off one card creates a snowball effect. Once you see that first card (or loan) paid off, it motivates you to want to pay off the rest (instead of evenly reducing all debts). Think of paying off each credit card or loan like getting one level closer to that financial freedom princess!

Momentum moves money mountains (a quick story)

Around the beginning of 2015, we had stashed enough money in our Debt Crusher account to pay off a credit card that had the highest interest rate. This was a CitiBank card with a 21% APR and a balance of over $14,000.

It was during one of our weekly budget meetings when Caroline and I hunched over my laptop. We logged into my CitiBank account. We clicked “Make A Payment.” We selected the magical option of “Pay Total Balance” (an option we hadn’t be able to select for many years). And we hit the glorious Submit button.

What a wonderful feeling that was! Up until that point, we’d only felt the mundane feelings that came along with paying minimum monthly payments. Yeah, some of our monthly payments had a little extra thrown in here and there, but none of them were as satisfying or motivating as paying off an entire balance. (I’d liken this to beating that first level of Donkey Kong where he not only throws barrels, but he starts throwing them rapid fire. Beating rapid fire Donkey Kong barrels proved to us that we could finally rescue our debt-free Princess!)

The little celebration we did lead to getting even more focused on wanting to pay off our debt as quickly as possible. We wanted to select all the “Pay Total Balance” buttons on all our debts. We couldn’t make it happen at that moment, but we could feel that snowball effect was in motion.

Hopefully this 4-part debt payoff plan gives you some really solid momentum toward debt freedom. Now would be a great time to make those hardship phone calls, look for 0% APR cards you can apply for, and get ready to organize all your debt in one place.


Step #7: The debt sucks spreadsheet

It’s Time To Organize All Your Debt In One Place

Congratulations friend, you are on your way to debt freedom! But before we release you into the financial wilderness with all the debt payoff strategies you’ve learned thus far, we have a pretty important spreadsheet to share with you.

Say it with me: Spreadsheets are our friends!

Just like you created a spreadsheet for Expense Tracking and Categorization (ETAC), it’s time to make another one that shows you exactly how much debt you owe. This additional spreadsheet will help you create a monthly payoff schedule that shows you exactly which debts need to be paid off in which order. This is the Debt Sucks Spreadsheet.

Seeing our debt laid out on one sheet was incredibly powerful. Yes, the total amount of debt staring us in the face sucked, but the fact that we could see a clear monthly path to paying off all our debt was incredibly helpful.

I’m going to walk you through how to use our Debt Sucks Spreadsheet step-by-step below. There’s also a video after the written steps if you want to see me using and updating the spreadsheet.

💸 Grab your own copy of the Debt Sucks Spreadsheet here.

Debt Sucks Spreadsheet

Step #0 to using the Debt Sucks Spreadsheet: Make your own copy!

When you open up the Google Sheet, you’ll need to make your own copy that you can edit. Simply go to the top menu bar: File > Make a copy… and boom, you’ll have your own version you can edit.

Steps #1 & #2 to using the Debt Sucks Spreadsheet: Enter in your debts

Now that you have your own copy of the Debt Sucks Spreadsheet, you’ll want to fill it out. Leave Column B as the last column you fill out.

Column A: This is where you’ll list your debts (credit cards, loans, etc).

Column C: Add the total current starting balance.

Column D: Add your interest rate (APR). Don’t be surprised if this information is hard to find!

Column B: The card or loan with the highest interest and lowest balance is your #1 priority (remember, this is the snowball effect).

If you have more than three debt items, we recommend copying and pasting one of the existing debt sections and adding it to the far right of the spreadsheet. Make sure to also add a new debt item in the top left section too.

Step #3: Add your balance and enter your monthly payments

You wrote down your credit card/loan balances in the top portion of the spreadsheet, now let’s add them to the corresponding color section below (to help you pay down those debts). Here’s a quick guide to where you need to match up your balances:

  • Cell C2 should match cell C15
  • Cell C3 should match cell H15
  •  Cell C4 should match cell M15

You only need to update cells C15, H15, and M15 in this step! The spreadsheet should update the rest of the cells automatically.

Once you’d add the Balance numbers to match, you can edit the Date and Amount Paid columns to match your debt payoff schedule. You may need to add more months, and you’ll certainly want to update the Date column to match your calendar. You enter monthly payment data in the Amount Paid that is your goal payment each month. (Once a payment is made you’ll change its background color to denote you made the payment.)

You will most likely not stick to the payment schedule you first write in. That’s okay! We didn’t either. Just make sure to go in and make the biggest payment you can and the Balance totals will update for you.

Step #4: Set your interest rates

This is the only complex part of the Debt Sucks Spreadsheet, but it’s not as bad as you think! You want to update the formula that calculates the interest rate so you can see the actual amount of interest you’re paying each month.

To update the interest rate for the first debt item, click on cell D16 (or 16D). When you click that cell, you’ll see the formula in the bar at the top of the sheet. We’ve set the default interest rate at 10% (or 0.1 as written in the formula). All you have to do is take the interest rate you wrote in cell D2, convert it to a decimal, and update the formula.

Example: Let’s say you have a 5% interest rate (APR) on your credit card. You’d enter 5.00% in cell D2 and in the formula in D16 you’d change 0.1 to 0.05.

Example #2: If you have a 24% interest rate (APR) you’d enter 24.00% in D2 and in the formula in D16 change 0.1 to 0.24.

Repeat this process for all cells in the “Balance Plus Interest” column where a formula exists (when you click the cell).

Step #5 to using the Debt Sucks Spreadsheet: Make your monthly payments and update the sheet!

Now that you have the Debt Sucks Spreadsheet setup with all your debts, your total starting balances, your interest rates, your estimated amount paid, you can start making monthly payments and denoting them in this sheet.

Don’t get discouraged if you can’t meet the goal you set for your monthly payments. Stick with paying down your debt and use this sheet to your advantage!


Step #8: Get a debt accountability partner

Accountability Will Help You Pay Debt Off Faster

You know what sucks about debt? Talking about it often. But you know what helps get rid of debt? Talking about it often.

Finding a financial accountability partner is key

If you have a spouse or significant other, I highly recommend this being your financial accountability partner. Conversations about money SHOULD be had in a relationship. Money is evil. It causes so many problems when not discussed often.

Debt isn’t fun and neither is getting out of it. Don’t do it alone!

But if you don’t have a spouse or significant other, you’ll want to get some financial accountability from another source. Here are a couple of recommendations:

Online or local groups: Are you in any Facebook Groups or do you attend any local meetups? Could you ask around and see if anyone wants to team up on attacking debt together?

Financial advisors: I always thought of financial advisors as crusty old men who wore those bright green visors you see in paintings that usually involve games of poker. Maybe there would be cigars involved, but most certainly, being $124,000 in debt didn’t qualify to talk to financial advisors. Then we were proven wrong. We were introduced to our financial advisors through a friend and have been using them since 2013. I’ll also mention that you don’t have to be wealthy, rich, or even making much money to have financial advisors. We had none of those things when we started our relationship with the financial guys we use.

Ask your friends: It may sound crazy, but given the stats I shared earlier about the average debt in the US, you are very likely to have a friend who is in a similar debt position as you. Don’t be ashamed to ask. Heck, forward them this article and have that be the way you broach the subject.

No matter who you team up with, finding a financial accountability partner is hugely beneficial. It removes all the pressure from your shoulders and allows you to have someone to commiserate with. Debt isn’t fun and neither is getting out of it. Don’t do it alone!

Weekly budget meetings will make all the difference

I may sound like a broken record, but our weekly budget meetings were the turning point in our debt story.

I give my wife a lot of credit (money pun!), she was the catalyst for starting our weekly budget meetings. At first, I hated these meetings. It sucked to confront the debt we had, most of which was caused by me and my poor business decisions. But as we started to talk each week about our debt and how we were working through paying it off, it became a much easier topic to discuss. The shame and embarrassment started to melt away.

It’s not an exaggeration to say that since 2013 my wife and I have had over 250 conversations about our finances.

When you have 250+ conversations about anything, progress is bound to happen! Sure, some weeks our budget meetings are short and sweet. We download our data. We review our spending. We update our budgets. We’re on our merry way. But every few weeks it’s a much longer, and sometimes difficult conversation. Those tougher meetings are that much easier with all the boring meetings sprinkled in between.

We can clearly remember being blindsided by random bills, business expenses, or even income before these weekly budget meetings. Now, we feel completely in control of the flow of money coming in and out of our accounts. It feels really effing great.


Debt Conclusion

Be Ready To Adapt, Change, And Iterate On Your Debt Payoff Plan

When we created our first debt payoff plan I was hell-bent on paying off all $124,000 of our debt in 12 months. Well, things didn’t go according to plan. We didn’t make as much money as we’d hoped and we had a few unexpected expenses pop up. But just because we didn’t stick to our first debt payoff plan, doesn’t mean we gave up.

We were able to pay down $60,000 of our debt in the first 12 months of our debt payoff plan. And, a whopping $25,000 of that money came directly from doing our Expenses Tracking and Categorization exercise (and then setting budgets, making sacrifices, and making those tough phone calls). So, $25,000 of our first year’s debt payoff came directly out of money we already had and otherwise would have wasted!

Week after week my wife Caroline and I would sit down, go over our finances, make our monthly debt payments, and update our Debt Sucks Spreadsheet. It took just under two years, but we finally reached debt freedom.

Paying off our final credit card

On June 14, 2016, we jumped over that final debt-filled barrel and kicked Donkey Kong right in his credit-card-loving face.

I simply can’t type enough words to explain how great it feels to be debt free. That $124,094 used to make us feel ashamed and embarrassed, but now all we feel is pride.

Our very last credit card to pay off was carrying a balance of $9,639. When we paid it, we immediately grabbed a phone and took a selfie (which, obviously, needed emojis added to it).

Being 100% debt-free is a feeling like I’ve never felt before. It feels like so much more is possible in life. It feels like we’re in control of the decisions we make. It feels like we’re breathing some really sweet, sweet oxygen these days.

If you’re currently in what feels like insurmountable debt, you can get out.

There is no perfect debt payoff plan. There is only the perfect plan you can create for your situation and your life.

Money is a deep, emotional subject for a lot of people and just talking about it can bring up a lot of negative emotions: guilt, shame, scarcity. But we promise the moment you acknowledge the barrel-throwing monkey in the room and make a plan to rescue your financial princess, things will start to change. They did for us.

Remember: It’s not going to happen overnight, and it’s not going to be easy. Short-term pain for long-term gain.

The Ethical Guide To Building An Email List Without Sleazy Tactics

May 30, 2018

Is it too late to build an email list? Do you need a big audience somewhere else to get email subscribers? Why do we think you should forgo any effort spent on social media and redirect it to email marketing?

Those are the questions we’re going to answer for you in this ethical guide to building an email list. Since 2009 my wife and I have seen the power of having a great email list, and by power we specifically mean building meaningful connections with other human beings AND getting some of those folks to purchase products or services from us.

Just to give you some social proof so you don’t think we’re copying and pasting the success of other people here, since 2009 our businesses have generated over $3,000,000 in total revenue and 90% of that money has come directly from our email lists.

You may or may not be focused on generating revenue with your email list, but we believe there is no better way to create a deep and strong connection with people online right now (yes, even in a time when social media seems to dominate the virtual landscape).

Let’s not waste another minute, here’s everything we know and have learned from our experience building email lists and growing our audiences.



Why Does Building An Email List Matter?

There are two main reasons why you should care about growing a great email list, and why you should focus on doing so before spending time growing a following on social media sites.

Reason #1: The way people interact with email

Think about it for a moment, people don’t quickly scroll through their email inbox, swiping past message after message, spending less than 3 seconds reading each email. Yet, this is the exact behavior when someone uses a social media application (scroll, scroll scroll, swipe, swipe, swipe) and they spend less than 3 seconds reading a Twitter or Facebook post. People open emails, they read them, and they spend quality time in their email inboxes every day.

Reason #2: Email is a playground you can mostly control

Social media sites, on the other hand, have fancy algorithms that change every few months. The audience you grow on Instagram, FB, etc, may have seen your content one month and then a month later you’re getting almost zero viewership. This doesn’t happen with email (often). I’ll talk more about how email service providers (ESPs) do hold some power, but it’s certainly nothing to worry about when you compare it to social media companies and how they can pick up their entire playground out from underneath you and you’re left holding your kickball and standing in a pile of (lonely) dirt.

Having an email list helps you create a genuine connection and trust

In Section 1 of this guide we’ll talk all about the nuts and bolts of starting to build your email list, but before that, let’s talk specifically about WHY building an email list is important.

Building an email list gives you the opportunity to create a value exchange with your subscribers. You deliver helpful or interesting content to their inboxes and they give you some form of patronage in return.

Trust is one of the most overlooked marketing tactics because it takes time. By showing up consistently in someone’s inbox and delivering them thoughtful content you will build trust. Your subscribers will come to appreciate the messages they receive from you, and in most cases will look forward to them and often times pass them on to friends (or save for reading again later).

Trust is what gets someone to go from curious onlooker to fan/customer. If you’re building an email list to generate revenue for an idea or business, building trust is something you simply cannot ignore.

My wife and I have been sending emails to our subscribers for years. We’ve honed our writing voices and we’ve found the niche topics we want to write about. You may feel like you’re completely in the dark with your writing voice and your topic, but have no fear, later on in this article, we’re going to help you discover those things too.

My 25,000 email subscriber mistake (incentivizing for list growth)

I put my first email signup form on a website (for my IWearYourShirt business) in 2009. I had no clue what I was doing, but several people had told me I needed to “grow an email list.” I had plenty of traffic coming to my website, so I started to get subscribers quickly. Actually, I started to get a lot of subscribers.

Over the course of a year, I racked up more than 25,000 email subscribers. There was only one big problem: I had no idea what to do with them.

I would send emails haphazardly. Sometimes on a Monday, sometimes on a Thursday, sometimes two emails on the same day if I felt like it. Whenever I thought I had an interesting thing to share, I sent an email to my growing list about it. This was problem number one, but not the biggest problem, by any means.

You see, after sending emails for a few weeks, I noticed a trend. The more emails I sent with giveaways, prize opportunities, or freebies, the higher the open and click-through rates. These two statistics were digital crack. I craved seeing them climb higher and higher. And the subscriber number? That was like, well, I don’t do drugs but whatever is better than crack. Super crack!

If you’re a veteran email marketer (or just marketer in general) you probably already know where this story is going. Either way, hold on tight because it’s about to be a bumpy ride.

The more giveaways and prizes I offered to this growing email list, the more interaction the emails garnered. An iPad giveaway here, a $100 visa card there, so on and so on. There were times when I could send an email to this list asking them to like a Facebook page, and more than 1,000 people would do it within an hour. That’s pretty damn powerful in the 2009-2011 era of social media.

But then I noticed another trend with my email list. When I sent an email without a giveaway or prize, the open and click-through rates were abysmally low. Even worse than that, those emails usually came back with negative responses and high numbers of unsubscribes. I’m not sure which hurt my ego more, but it’s silly to look back and think that I let any of that dictate my decisions so much.

Nevertheless, I kept the email list going for years. I reduced the giveaways and sent fewer emails.

I hated feeling like I built a sizable email list of people who only cared about giveaways.

I tried lots of different content in the emails. I varied the sending schedule and even tried a set day and time for a while. I tried segmenting the list. I tried deleting huge chunks of subscribers (we’re talking 5,000+ at a time). I took a break from sending any emails to this list for nearly a year (never a good idea by the way). I even tried changing the name and email address of who the email came from. Unfortunately, the damage was already done and the list was essentially worthless. In fact, it was costing me a couple thousand dollars every year.

After two years of trying everything I could think of to cater to this large list of subscribers, I finally gave up. I realized I had fallen into a sunk cost trap, and just needed to let go and move on (which as we all know, is never easy).

So I sent three final emails:

One announcing the list was closing down.
One letting people know they could get on a new email list I was passionate about that wouldn’t feature any giveaways. I was very clear about the type of content the new list would receive.
And the last email simply thanked them for being subscribers and said goodbye.

Then I deleted the entire list. I didn’t back it up. I didn’t save it. I just deleted it. 25,000 subscribers gone.

After all was said and done, only about 200–300 people moved from my 25,000+ person email list. And that made me happy.

You still might be wondering why I would walk away from 25,000 subscribers. It’s simple. They were the wrong subscribers for me. They weren’t my “Rat People,” as my friend Paul Jarvis says. They weren’t my “Tribe,” as Seth Godin says. It was simply a list of people who wanted something from me that I wasn’t happy giving them.

To recap: Do not build an email list based on giveaways and incentives. Build an email list of people who want to read your emails and are interested in you and what you have to say.

My thoughts on email marketing have changed drastically over the years. You might assume I loathe email marketing and list building because of this story and my not-so-great-experience. But it’s actually the contrary. My second email list, the Action Army (for my previous JasonDoesStuff website), brought me a ton of value and dollars in my bank account from 2014-2018. I made a mistake and failed with my first email list, but I also learned a lot from the experience too.



Where Do You Start With Building An Email List?

Many people want to start by picking an email service provider (ESP). Or they want to throw some email signup forms on their site. But these two steps are way lower on the list of important decisions and steps you need to take.

If you can stick with me, follow the upcoming advice from loads of firsthand experience, you will be building a highly engaged audience in no time.

Step 1: Before building an email list you must tame your ego

Have you heard the term “vanity metrics” before? If not, that’s okay, and probably for the best. However, we’re all guilty of getting sucked into vanity metrics. Vanity metrics are the little numbers associated with website traffic, social media followers, notifications of likes, amount of email subscribers you have, and many other things. Sometimes these metrics can be helpful, but the majority of the time they’re nothing more than a distraction from what really matters.

To avoid getting sucked into the vanity metrics of email list building (read: how many email subscribers you have) you must tame your ego.

When it comes to anything that can be quantified, our egos quickly become our worst enemies. And boy-oh-boy, do we live in a time with numbers being shoved in our face at every turn. Almost every platform puts some sort of vanity metric front and center any chance it gets. The more numbers you see the more numbers your ego craves.

I wish I could tell you there was a magical way to tame your ego. Some ego-taming app you could download that would save you from the itches we get to check all our metrics. YOU simply have to be that ego-taming app.

I told you about the 25,000 email subscribers I deleted. During that time I was heavily focused on building an email list with lots of subscribers (quantity). What I should have focused on, and what I only focus on nowadays, is building a highly engaged list of subscribers who want to read my emails and who look forward to having my name show up in their inbox (quality). Don’t worry, I’m going to help you define your ideal subscribers in a moment.

Whenever you find yourself getting stuck worrying about how many email subscribers you have (or don’t have), take a step back and ask yourself if your email list is helping you build the connections and trust you seek. That could be with only 10 people or 100 people. That’s okay! And if you’re just getting started, give yourself the time and space to build a quality email list. It may take you a year or two to have enough email subscribers to help you reach whatever goals you’re setting for yourself/your business.

TIP: Instead of worrying about the amount of email subscribers you need, define a goal for your business that your email subscribers can help you reach. Then, focus on the goal of your business not the vanity metric of how many subscribers you have.

I remember that it took me an entire year to go from 400 email subscribers to 1,000 email subscribers. That was less than 2 new subscribers per day, and in the beginning, it was 0 new subscribers per day for quite a while. I constantly told myself not to check how many subscribers I had and to simply keep going on my mission of writing helpful and interesting emails no matter the amount of subscribers.

Learning to tame your ego can help you sift through the numbers and find the people who give you the most value.

Step 2: Define the type of audience you want to reach

The easiest way to attract the right people to join your email list is to be crystal clear about who the heck you want to talk to (and most likely who you can help).

Let’s look at an example and say that you’re a freelance web designer who has been doing design for years and wants to help up-and-coming designers learn the ropes of working for yourself, honing your craft, and staying up on design trends.

A fun way to always have this person in your mind is to give them a name. Let’s say your ideal subscriber’s name is Linda (everyone say, “Hi Linda!”).

Now, describe Linda. Answer these questions about your fictitious person to help you understand how to speak to her, how to be helpful to her, and how to make sure she’s the right person to join your email list:

  1. Why is Linda a designer in the first place? Was she creative growing up? Does she love art?
  2. Where does Linda spend her time online? What sites inspire her?
  3. Where does Linda shop? What things does Linda like? What things does she dislike?
  4. What is Linda struggling with that you can help her accomplish (because you’ve accomplished those things or are trying to)?

These questions may seem silly, but we’ve seen the value of them and how much easier it becomes to attract the RIGHT subscribers and detract the tire-kicker subscribers who are just going to waste your time and money (because, you pay for subscribers!).

Here are some example answers to those questions, just so you have an idea of how to build this avatar of Linda:

  1. Linda loves art and has been creative her entire life. She grew up painting on walls with crayons and then found web design and fell in love with designing websites for other people.
  2. Linda visits Site Inspire, Awwwards, and loves creating inspiration boards on Pinterest. She also enjoys sharing her work on Dribbble, but doesn’t spend too much time there.
  3. Linda stays low budget by shopping at Target, but has been known to splurge on high-quality items at Madewell. She loves supporting creative business owners and has dreams of making food truck websites full-time because she’s a foodie. Linda doesn’t like arguing about design principles and isn’t a fan of traditional furniture.
  4. Linda wants to get more clients, but also wants to get clients in the food industry. She’s been using Photoshop her entire life, but wants to transition to Adobe XD and learn some new skills.

Once you’ve defined who Linda is and answered all the questions about Linda, keep this persona in a safe place. This is your audience definition filter. Constantly remind yourself of the traits that make Linda who she is, and get ready to speak directly to Linda in every piece of your content, especially in your email signup forms on your website*.

One of the biggest mistakes most people make when it comes to building an email list is using generic copy on email signup forms. “Subscribe to get my updates” barely speaks to anyone and certainly doesn’t help qualify a good subscriber.

*Again, we’ll get into the weeds of what email service provider to use and some tips and tricks to help improve your subscriber conversion rates on your website. Just hold on tight, we’ll get to that.

So, the wrong way to entice Linda to signup to get your emails on your website is by having the text, “Subscribe to get my updates” next to the email signup form.

The right way to speak to Linda and help her understand how your emails are going to help her is to write something like:

“If you’re a freelance designer who lives in Adobe Photoshop or XD and you want to get more quality design clients, my weekly emails will help you!”

In the answers to the questions about Linda, you should have found things to add to this copy you’re putting on your website. Remember, you created this little fictitious persona to have as an audience filter.

Going forward, whenever you finish writing an email or article (or creating any piece of content) ask yourself, “Will this help or resonate with Linda?” If it doesn’t, make it helpful.

Don’t be afraid to be polarizing when it comes to defining your audience. The best audience you can build is a small, highly-focused one. It will reward you for many years.

Your audience connects with you because you share strong values. And the only way they’ll know how you think and what you value is if you’re outspoken and clear about it.

Step 3: Let’s talk technically, how can you convert people to email subscribers?

Email forms on your website

I cannot imagine you’re reading this guide and that you don’t have a website, or at least have a plan to create a website. But here’s the thing, there are some dos and don’ts when it comes to converting websites visitors into email subscribers.

DO: Clearly explain on your email signup forms why someone should subscribe and what they will get from your emails.

DONT: Use vague generic messaging on your emails forms, like: “Sign up to get my weekly newsletter.” Instead, say something like: “Sign up to get my best advice about running a graphic design company (new helpful emails every Tuesday!)”

DO: Put email signup forms on more than one page of your website. On our site you’ll see email forms on the Homepage, About page, Newsletter page, the bottom of every article/guide, and a few other places.

DONT: Just put an email signup form on your homepage and call it a day. People may need to see your email signup form a few times and learn more about you via your website to decide if they want to subscribe. Don’t shoot yourself in the email-list-growth-foot by using only one or two email forms.

Pop ups and exit intent windows on your website

DO: Treat your website visitors like YOU want to be treated. Do you like landing on a website and immediately getting a pop-up message to enter your email?

DONT: Try to convert every website visitor into a subscriber by smacking them in the face with pop-ups and exit intent windows at every turn. Sure, maybe try using an exit intent email signup form on a page or two on your website. The key word is “try,” because you want to test the results of using that tactic (don’t just blindly do it).

Picreel and OptinMonster have great tools for helping you grow an email list. Just be careful and remember to treat your website visitors how you want to be treated when you land on a site.

Free downloads or free email courses

DO: Remember what I said earlier about building an email list based on incentives. It can lead to an email list of people who only want free crap. If you’re going to offer free downloads make sure they’re in direct alignment with what you’ll be sending your subscribers emails about.

DONT: Use crappy “lead magnets” (free downloads) just because it’s a tactic you can use. Create a really helpful email course that actually solves a problem for your potential subscriber.

Constantly remind people that you have an email list

DO: Talk about your email list on social media or any other places you create and share content of any kind (yes, tweets are “content”). Just because you’re tired of asking people to join your email list doesn’t mean they’ve heard you or even know you have an email list.

DONT: Spam every other platform with asks to join your email list. Lead with value. Remind people what they can get from your emails. Get create and try to have fun infusing the ask of subscribing in with your other content.

Write REALLY great emails to your subscribers

DO: Focus on sending valuable emails that people will want to share. When you’re crafting your email content ask yourself, “is this something worth talking about?” If the answer is No, that’s okay, just realize your emails aren’t helping you grow your audience.

DONT: Take the opportunity of visiting someone’s inbox lightly. I’m not saying put pressure on yourself and psyche yourself out, I’m just saying that you should be thoughtful and spend time and effort crafting quality content for your subscribers.

This Audience Guide started out as a simple email to my subscribers about the things I’d learned building an email list. My subscribers found it quite helpful and shared it for me by forwarding it to their friends.

Step 4: Commit to Consistency

We’ll get to WHAT you should send emails about in Section 2 of this guide, but there’s an important mindset that my wife and I strongly adhere to:

Creating great content can attract your audience members but creating consistent content keeps them.

No matter what sending schedule you intend to use for your email list, staying consistent and giving your subscribers a schedule they can look forward is important.

Are you worried that you don’t have any subscribers at all right now and that thinking about sending consistency isn’t important for email list growth?

My wife sent her first newsletter to just 4 subscribers, 2 of which were her and me. She stayed consistent and two years later had a list of more than 10,000 subscribers!

Are you worried that if you commit to a weekly email sending schedule you’ll run out of things to email about after a few weeks?

I keep a running list of topics I want to email my list based on things that interest me but also regularly get inspiration from questions I get from my audience. Out of the 400 articles I’ve written over half of them (200+) have come from questions people emailed me about.

Are you not getting emailed any questions at all right now? Then you need to start creating and sharing your work! You need to make stuff. You need to be known for something. It won’t be perfect when you start and that’s 100% normal.

The beauty of building an email list and sending an email newsletter is that YOU determine the schedule at which you publish, and you can rest assured that your audience is going to actually have a chance to read that content. On Facebook, you could post every day and those that have liked your page (or you’re friends with) might never even see your posts. On Twitter or Instagram, your followers have to come across your post at the right time to see it, or it’ll likely never enter their consciousness.

An email, on the other hand? An email patiently waits in someone’s inbox to be opened. They may or may not read your newsletter that week, but just by hitting send you’re subconsciously communicating to them that you’re reliable and that you continue to care about how you can provide valuable content to them.

Consistency is an email growth tactic, whether you want to believe it or not. Think about the people you subscribe to, listen to, read stuff from, watch on YouTube, etc. You come back to those folks time and time again because they create and share things consistently. You can do the exact same thing and be in a similar position as them when it comes to having an engaged audience. Commit to consistency, right here and now.



What The Heck Should You Even Email People About?

I remember back in 2013 when I was transitioning from a failed business to not knowing what the hell I was going to do with my life, I felt like I needed something concrete to build an email list around. I needed a focus, a niche, something that people could latch onto!

But I had nothing… Hah!

Probably not what you were expecting, right? Well, it happens to all of us.

I did what any scrappy entrepreneur does and decided to start ugly. I decided to not have the perfect focus or niche and instead just get my email list going and use these next two mindsets to guide me.

Thing #1 to email people about: Something helpful

Let me give you two example scenarios, one of which was my own email strategy back in 2013 when I had no focus at all. But before I do that, here’s one important mindset shift to make: No one starts out as an expert. You don’t have to get to some arbitrary level to be “good enough” to help other people.

Example A: You’re a photographer who wants to help other photographers

You don’t have to be Ansel Adams to give advice on photography. Odds are if you’re making money by taking photos, you have a LOT you can help aspiring photographers with.

  • Write an email that explains composition in a way that people might not think about it
  • Write an email that dispels the need to own expensive gear (and what gear actually matters)
  • Write a step-by-step guide on how to get a certain type of photo
  • Write an email about why custom function buttons on DSLRs are the most underrated and under-talked about feature

I could go on for hours because I’d sign up for those emails! I don’t even want to make money from photography, I just want to read helpful content about it from someone who isn’t stuck up or boring.

One pro-tip on finding content for well-known niches (like photography): Head to YouTube and search “photography tips.” Find the 10 most viewed videos and write articles/emails that put your spin or take on those things. Boom. Rinse and repeat for many additional content ideas.

For this example feel free to replace photographer with whatever craft or talent you focus on. That could be videography, cooking, running, writing, etc. Just remember to be helpful and focus on giving tons of value to your subscribers!

Example B: You’re like me and you don’t really know what to write about, so you just write!

Here’s my non-example, example! So, what the heck do you create helpful email content about if you don’t know what you can help with?? Great question. This is exactly what I did, broken down into three content types:

1 – Help people avoid your mistakes. At the time in 2013 people would email me asking for marketing or business advice. Even though I felt like a fraud answering them (because my million dollar business tanked, I realized I could share all my mistakes and lessons learned and THAT was helpful). What lessons have you learned from your mistakes? How can you help someone avoid the pain you ran into?

2 – Help people by sharing your journey with them. A big part of my success building an email list in 2013 while not having a specific focus was that I brought people along with me. In my weekly email newsletters, I’d share something I tried or a book I read or anything that was helpful to me on my own journey. What journey are you on that people can relate to? What things are you trying that folks may find interesting? Don’t sell yourself short, people love watching/reading about other people doing stuff!

3 – Try latching onto something. For me, as vague as it was, I tried latching on to the idea of “taking action.” I told you it was vague! But, it helped. Even though taking action doesn’t excite everyone, there are people out there that align with it. Having something for people to resonate with is better than having nothing at all (no matter how vague). What is ONE thing you can have people latch onto? What’s something you believe that’s slightly unique to you that you can talk about?

Thing #2 to email your subscribers about: Something entertaining

My favorite email newsletter I’m currently subscribed to breaks every email marketing rule in the book. It’s insanely inconsistent in the delivery schedule. The formatting of the email is not great. The thought and effort that goes into the email itself is sad. BUT… the actual content I receive is worth dealing with all that stuff.

The Oatmeal Email Newsletter

Yep, the comics from The Oatmeal are my favorite email newsletter. The content is so fun and entertaining that I look past everything else.

Would I love and appreciate The Oatmeal even more if I received consistent emails? Absolutely! But, the cartoons are so good that when they do finally arrive I love them to death and am so glad I’m subscribed.

There’s a ton of value in being entertaining. There’s a lot to be said for bringing joy and happiness into people’s lives.

We live in a culture dominated by entertainment. Look around and you’ll see entertainment at every turn, on every billboard, it’s nearly impossible to escape. Sure, there’s good and bad entertainment, my point is that people love to be entertained, so find a way to authentically entertain them if you can!

I’m nowhere near as talented as Matthew Inman (creator of The Oatmeal), but I do my best to infuse my own humor and try to entertain my email subscribers when I can. A couple simple ideas that go a long way:

  1. Humor! You don’t have to be a standup comedian to be funny. Just be you and let your freak flag fly.
  2. Uniqueness. I looove when I get emails from people who are pushing boundaries and trying to do things in new ways.
  3. Boundary-pushing and rule-breaking. It’s fun to watch other people buck the system (whatever system that may be).

Don’t be afraid to entertain and build an audience around your personality. I wouldn’t say try to be the next Jersey Shore contestant (woof), but embrace who you are and what people say stands out about you.

Pro-Tip: Ask people a question in your welcome email

Obviously, you need a few email subscribers knocking on your door for this tip to work, but even if you have 15 new subscribers a month, this strategy can work for you.

Your Welcome Email, aka the email that a new subscriber gets right after they sign up is going to be the email with the HIGHEST open percentage… ever.

Take advantage of that opportunity and ask your new subscribers a question in that email. A couple questions I’ve asked in my Welcome Email over the years:

  • What’s the #1 thing you’re struggling with in your business right now?
  • If you could get rid of one problem in your life, what would it be?
  • What’s harder for you: Coming up with new ideas or executing them?
  • What would brighten your day today?
  • Is there something, anything, I could help you with right now?

You’d be shocked at how willing people are to answer a question after they receive your Welcome Email. You have to remember the mindset they’re in: They just signed up and they’re probably never going to be more engaged with your email content.

In 2014 I used the “…struggling with right now?” question in my Welcome Email and amassed over 600 responses in one year. About half of the replies I received led to creating an email, blog post, or product I could sell. The great thing about asking something of your subscribers is you get to learn what they want/need and then you can help them with that thing!

Don’t forget to focus on sending people emails that you’d want to receive.

It can be easy to get caught up in the monotony of writing emails, staying consistent, keeping up with your business, and letting the quality of your email content dip.

A simple way to make sure you aren’t letting your content get stale or boring is to ask yourself: Would I be excited to open and read this email?

If your honest answer is No, then you need to write a better email. If you send your subscribers mediocre content, you shouldn’t be surprised when they unsubscribe or start ignoring your emails. Send emails you’d want to read!



Email Providers, Subject Lines, and Other Email List Tips

At this point, I have to assume you already have an email list or you’re on your way to creating one. Yay you! Having been in the email marketing game for over a decade I can safely say that I’ve made my fair share of mistakes and learned plenty of lessons. I’m guessing you caught wind of that already, huh? Let’s dive into a few of those things now!

The $1,000,000 question: What email service provider is best? MailChimp? ConvertKit? InfusionSoft?

I’m going to give you an abridged version of my answer to this question because I wrote a separate article that does an in-depth breakdown of my top three email service providers (you can find that here).

Instead of answering this question by reviewing every email service provider (ESP) in existence, I’m going to instead give you my choices based on where you might be on your email marketing journey. You know, focus on your actual needs and not just focus on features or price!

If you’re an email marketing beginner, don’t need much email automation, and/or want to save money: Use MailChimp

MailChimp is probably the most well-known ESP and it’s for good reason. They’ve built an amazing email platform and it’s continually getting better.

These are the three best things about MailChimp:

  1. Free until you hit 2,000 subscribers (amazing!)
  2. Fantastic email campaign builder that anyone can use
  3. Recently added subscriber tagging and better automation!

Two not-so-great things about MailChimp:

  • If you don’t pay for an account, you can’t contact an actual customer service person
  • Their affiliate program is whack (like, awful)

I don’t think those two items are deal-breakers though. MailChimp is a FANTASTIC option and you’d probably be super stoked to use it.

If you sell digital products or want to do some behavior-based subscriber actions: Use ConvertKit

I was a happy ConvertKit customer for two years. The only reason my wife and I left was that we wanted to get into some much deeper email automation and at the time ConvertKit’s automation builder was very ho-hum (spoiler: that’s changed).

Three great things about ConvertKit:

  1. Subscriber tagging and automation rules based on various actions are really well done
  2. Their new automation builder is suuuper slick and easy to use
  3. They do a great job with email analytics (form analytics, and much more)

My only (personal) drawback for ConvertKit at this point:

  • I don’t like the company they use behind the scenes to send emails (Mailgun)

I had a really crappy experience with the company Mailgun back in 2012 and haven’t felt like letting go of that grudge (nor do I think I need to #sorrynotsorry). That being said, I also saw quite a dip in my email open rates over time with ConvertKit, even after doing email list pruning. This may not be an actual problem for you and maybe Mailgun is run by better people now?

If you do a lot with email automation: Use Drip

Drip is the current email provider we use for Wandering Aimfully and we’ve been pretty happy with it. There have been a few blips in the road, which I’ll share, but overall I’d recommend Drip over extremely complicated solutions like InfusionSoft, Ontraport, AWeber, etc.

Three things we love about Drip:

  1. The interface is really solid, especially for a complex automation-focused platform
  2. Customer support has always been top-notch (both live chat and email)
  3. They seem to be constantly improving the platform (being owned by Leadpages helps!)

Two things we wish Drip would do better:

    Have better email form analytics (of all the data Drip can show, not having form analytics easily accessible is so bizarre)

  • Come down in price to compete with MailChimp

I’m all for paying for great products, which I believe Drip is, but MailChimp is inching closer and closer when it comes to features and they charge half the price for the same amount of subscribers (for our ~15,000 subscribers we pay almost $300 on Drip and would pay $150 with MailChimp).

When it comes to picking the right email service provider the good news is that it’s not that difficult to switch.

Since 2013 we’ve moved from MailChimp to ConvertKit to ActiveCampaign and finally to Drip. The process is actually fairly painless to switch and each service has offered a hands-on migration to help make the process smooth.

Let’s talk about those pesky email subject lines and how you can write better ones!

There are a plethora of articles you can read on the topic of writing great subject lines. I’ll link to a few at the end of this section, but I do want to share a few simple principles with you.

Don’t play the clickbait game: It’s super easy to get caught up in the open rate success of “you’ll be shocked to read this!” style subject lines. The problem and I’ve witnessed this firsthand, is that the shock value wears off and so does the attention of your subscribers. Instead of playing the clickbait game, just be straightforward with your subscribers and let them decide if they want to read your content.

Your best subject lines are almost always going to be the simplest: The email with the highest open rate I’ve ever sent (outside of the Welcome Email) had the subject line “can you help me out with this?” Just a simple question that piqued people’s interest. K.I.S.S. applies to writing subject lines too!

Don’t over emoji it: Listen, I adore emojis. I use them constantly. However, you can overdo it with emojis in subject lines, especially when you understand that not all email inboxes interpret emojis the same way (Gmail, for instance, has it’s own emoji library that sometimes conflicts with Apple’s emoji library – ugh, so dumb). I’m not saying don’t use emojis, just don’t go 🦍💩.

As I mentioned, I have a few additional resources you can check out that can help with your subject line writing:

And while all these tips I’ve shared and linked to are great, the most important thing you can do to write better subject lines is just to write and share them. Let your own data educate you on what YOUR audience resonates with (and what entices them to open your emails).

Unpopular opinion alert: If you’re selling something via your emails, remove your social media links

This may seem a weird topic to have an entire section dedicated to it, but that’s how strongly I believe that people need to stop including social media links, share buttons, etc in sales emails.

Let me paint a picture for you, ready?

Jeremy is a photographer and he’s created an awesome online course that can teach other photographers how to book more clients and create a more streamlined photo editing process. His photography course is wonderfully helpful and people are going to love it!

Jeremy sends out a weekly email to his list and is about to queue up a sales email for his course. He meticulously writes his sales copy, addressing all the necessary pain-points and highlights around his new course. He’s happy with his email and he schedules it to be sent. Go fictitious Jeremy!

His loyal subscribers start opening the email and reading about his course. They’re excited! They know this course will help them. But then, they get to the bottom of the sales email, ready to learn more and potentially purchase his photography course when they see a Facebook icon. “Hmmmm…” the subscribers’ brain perks up. “We love mindlessly scrolling through baby photos on Facebook, let’s go do that, it makes us feel good!”

And boom, now Jeremy’s potential customers have scurried off to the catacombs of social media, never to be seen again.

So yeah, that story is a bit silly, but it illustrates my point. Social media sites like Facebook, Twitter, etc, have created immensely strong mental connections and if you give someone’s brain a chance to, it will run off any scrollable feed possible.

If you’re going to sell something in an email, remove any chance that someone could get distracted from making a purchase.

If you have data to back up that your subscribers use your social media sharing icons and links when you aren’t sending a sales email, then leave those links/icons in place. But if you’re trying to sell your product, you better believe that your subscribers need ONE clear focus (and it’s not baby photos!).

A couple of advanced email marketing tips and tricks

These are by no means mandatory, but I wanted to share a few of the more advanced email-related things I’ve learned over the years.

Email marketing trick #1: Use to test your emails

For quite a while I used every single week when I was queuing up my newsletters. This 100% free service is a great way to see if your emails are going to run into any trouble when you send them. Mail-tester will grade your subject line, email content, let you know if there are any issues with your from email address being on any sort of sending blacklist, and they even have some super-nerdy trickery you can do to help your email deliverability (setting up DKIM and dmarc stuff).


Email marketing trick #2: Survey your subscribers using Typeform

I was super hesitant to ever survey my subscribers because I don’t ever fill out surveys when people send them to me. But then, on a whim in 2015, I decided to send my very first survey. Out of the 2,000 people that opened my first survey email, over 500 of them filled it out! WHAAAT?? This wasn’t a simple score-based survey, I asked folks to leave long-form answers (and they did). Those email survey replies led to the creation of multiple products, a podcast, and loads of content topic ideas. Plus, some subscribers asked simple questions that I could answer, which helped increase trust, and made me feel like I was over-delivering on value.

Here are some questions that are great to include in a survey:

  • What is the thing you are struggling with most right now?
  • What email have I sent that you remembered and has stuck with you?
  • Why would you say you stay subscribed to my emails?
  • What could I do better with my emails to help improve your situation?
  • What do you do for a living?
  • How do you describe yourself?
  • What’s a small thing that could make a big impact for you right now?
  • What’s your name/email address? (This seems like a no-brainer, but it’s easy to forget!)

Typeform Surveys

Email marketing trick #3: If you send a survey, have a unique offer after completion

Once I got the taste of sending a survey and see how people actually enjoyed responding, I decided to put another task to the test. I’d heard of people sending surveys to their audience and offering a unique product after survey completion, but it seemed weird to me. Why would these people A. take a survey and then B. buy something right after!? But if you think about it, the subscribers that are willing to fill out a survey, are your BEST and most interested subscribers. Of course, they might want to buy something from you! So, in 2016 I sent out a survey to a segment of my audience (the folks who opened my emails the most) and at the end of the survey, there was an opportunity to buy a $1,000 product discounted to $500 (with only 15 purchases available). Just a few short hours after sending out the survey all 15 purchases had been made and I had $7,500 sitting in my bank account. Crazy!

I can’t guarantee you the same success, but by all means, give this a chance or two, and start sending those surveys!

Email marketing trick #4: A/B test, but keep your tests simple

I feel like A/B testing is really great when you’re first gaining some email list growth (around 1,000 subscribers). You do need enough people to have the data help you make decisions, because let’s be honest, having only 50 subscribers and knowing what 25 of them want versus the other 25 may not prove too helpful. When you do start to get some traction, A/B testing your subject lines, or the first or last paragraph with a call-to-action, or other small tweaks, are great things to test… just not all at the same time! Pick one thing to A/B test each week. Learn from the data and then test something else. The idea behind A/B testing is really to understand how you can speak directly to your audience and have them stay thoroughly interested.

Mailchimp A/B Testing

Do you have any awesome email marketing tricks you think I should include in this section? I’d love to know what’s worked for you! Shoot me an email and let me know.



5 Email List Building Mistakes To Avoid

At this point, you know why having an email list matters and you’re starting to build a plan of attack to grow that email list and send your subscribers consistent valuable content. But hold the phone, how can you avoid a bunch of common pitfalls during that process?

Let’s look at the five most common email list building mistakes I’ve seen (and even committed myself) over the years and how to avoid them:

Mistake #1: Being unclear about what a subscriber will get from your emails

Be crystal clear about what your subscribers are going to get if they sign up for your email list. Let them know the schedule, the type of content, and what kind of value you are providing them. Put this information right next to your signup form on your website and remind them of it in a Welcome Email.

Note: When/if you sign up for our Wandering Weekly emails (at the bottom of this page) it should be very clear what we’re going to send you. Once you sign up we have a very thorough “what to expect” page that leaves no stone unturned so there are zero unwanted surprises.

Mistake #2: Focusing only on the number of email subscribers

Do not worry about the numbers. I know this is a very difficult task as a human being as we’re simply wired to pay attention to the numbers. The number of subscribers you have isn’t going to grow because you refresh your subscriber analytics on a daily (or maybe hourly) basis. Instead, spend all that time and energy on creating great content for your readers. If you only have 15 subscribers, that’s totally fine. Pamper the heck out of them, engage with them, but make sure you’re doing it with the content you want to be sending.

Fun fact: I launched my BuyMyLastName idea to an email list of just 600 people. That project had $30,000+ in revenue in the first 24 hours because of that small email list. Quality, not quantity!

Mistake #3: Making it difficult for people to unsubscribe

Don’t hide the unsubscribe button or unsubscribe link in your emails. I know you don’t want people to unsubscribe, especially in the beginning. But as weird as it sounds you WANT people to unsubscribe as soon as possible. If what you are emailing isn’t in alignment with a subscriber why would you want to pay to keep them on your list (paying in time or money)? I’d advocate that you should make the unsubscribe option prominent in your emails and easy for people to find. I promise you, if someone wants to leave your list, you should let them go and wish them well on their way.

Mistake #4: Don’t build an email list with giveaways or incentives

You remember my 25,000 email subscriber story from Section 1, ya? Unless you’re Groupon, do not create an email list with giveaways, deals, and prizes. Trust me on this one—you’ll build a list of people who only want those things. It’s not worth the extra subscribers because they won’t bring you any value in the long run. They’ll actually end up costing you time and money.

Mistake #5: Overdoing the formatting of your emails

The majority of emails I love getting in my inbox barely have any formatting. Good content creators know to let the content do the talking and to avoid distracting the reader with too much extra fluff. Should you include an image or two in your emails? Absolutely! Might you want a nice header image that shows some of your personality and branding? Yep. But do you need to use all the fancy email templates, designs, background images, blah blah blah? Nope. Make your content great and easy to read. That’s your goal.

Mistake #6: Delivering mediocre content via your emails

Your main goal with your email marketing strategy should be to deliver unique value to your subscribers with every email. Don’t copy someone else’s strategies. Don’t copy subject lines. Just pour your uniqueness into every email you write. If you want to figure out what your subscribers want you to send them, ask a question in the Welcome Email they get after signing up for your email list. Something like, “what’s your biggest struggle right now?” or “what can I help you with?” Those replies will become perfect topics to send emails about going forward.

Don’t over-automate too early and focus on consistency

This mistake is so egregious I had to give it its own section. I’ve watched too many creative business owners waste countless hours of time by trying to build slick email automations too early on. The thinking goes something like this:

“I need someone to get my free email course, then after they finish my course get bridged into an automated sales pitch, and then that sales pitch needs a countdown timer and all of that needs to update stuff on my website too.”

No. No. No. No. You may think you need this type of “email sales funnel” so you can make passive income, but you absolutely want to skip this in the beginning.

Getting caught in the weeds of automation too early can cause way more headaches than it can generate revenue for you. Instead, just send simple email broadcasts to your subscribers. Deliver value to their inboxes and establish trust with them. Then, by okay with selling via emails that don’t have any automation and don’t have any bells and whistles.

If what you are creating is unique and helpful, you don’t need slick automations, you just need consistency.

Consistency is sooooooo underrated when it comes to online business and email marketing strategies. You’d be shocked at how few people can stick with a consistent content schedule, even if that schedule is just one email a week (a tactic I’ve used since 2014 and I’ve generated plenty of revenue with it).

When you feel yourself starting to go down the automation path ask yourself a simple question: Am I selling enough stuff with manual effort right now that I need to automate?

That’s the only time to start thinking about automation. Not in the beginning. Not when you’re just getting started and figured everything out and trying to build good consistent creation habits. Automation too early on will rob you of your creativity and derail you.



A Few Final Tips To Keep Your Newsletter High-Quality And Authentic

Tip #1: Come up with a format that feels suited to you

Work with your strengths! My wife and I loooove to write and tell stories about our lives so our emails tend to be longer and that’s perfectly okay with us. If you don’t love writing but you love talking, try filming a short video and sending that out to your subscribers instead. Remember, going with something that feels natural to you will make it easier to keep up with consistently because you’ll enjoy the process.

Tip # 2: Tailor your content to your email list specifically

You can include links to posts on your blog, but save some content that feels tailored and specific to just your email subscribers. In other words, give them a reason to subscribe and not just to visit your blog. My wife and I tend to always write for our email list first, then we decide if that content should go on this website or not. This is something you can highlight on your email signup forms and when you talk about your email list. Something like: “Every Monday I send out my best writing exclusively to my email list on what it takes to run a creative online business.” Sounds enticing, right? Don’t you want to get exclusive writing? I know I do.

Tip #3: Don’t write in anyone else’s voice but your own

Finding your unique creative voice is hard. It’s tempting to simply go with what you see works for other people, or sometimes it’s just hard to get other people’s voices out of your head if you often consume more content than you create. But, similar to the point above about finding a structure that works for you, you’re only going to want to stick to your newsletter consistently if you write in a way that is natural and unique to you. When I started writing my email newsletter I had all kinds of self-doubt that my writing wasn’t very “good” and that I didn’t know all the proper writing “rules.” But who cares!? You and I aren’t trying to win a Pulitzer Prize with our words, we’re simply trying to build a passionate audience and run a profitable business. People will be able to tell when your personality comes through so do yourself a favor and let it shine!

The best email strategy is the one you can stick with and the one you enjoy pouring effort and energy into.

If you focus on delivering valuable content to your subscribers on a consistent basis you will build an audience in an authentic way. The key is to start, stick with it, avoid getting caught up in the numbers and continue to create and share things with your subscribers.

Which Email Service Providers Should You Use? (MailChimp vs ConvertKit vs Drip)

February 6, 2018

A decade ago, there weren’t that many options when it came to what email service providers (AKA email marketing companies) you should pick. These days, there are too many options, and all of them seem to have plenty of pros and cons.

I’ve done the hard work for you and believe you should pick from these three email service providers:

  • Mailchimp: You’re just getting started, you’re budget-conscious, and you don’t need lots of bells and whistles.
  • ConvertKit: You want a few bells, a couple whistles, and make your money selling digital products.
  • Drip: You’re an email marketing pro, and you want to do ALL the custom email things.

Let me help you pick the right email service provider…

I want to help you compare MailChimp vs ConvertKit vs Drip, but also give you some additional information that will help with your email marketing efforts.

Disclosure: I have NOT been compensated by any of these companies to write this article. Instead, I’ve gone through the gauntlet of using 10+ email marketing providers over the years and found that these are the three best options. I am including my affiliate links to each, which doesn’t cost you any extra and gives me a tiny kickback if you signup. 

Email Marketing

Section #1 – My $54,000 Surprise Email

The Power of Email Marketing And How I Stumbled Into Using It

In June 2009 I put my first email signup form on my website. I ended up collecting around 500 email addresses over the course of three months (I’ll talk more about growing your email list in section #5). In September of that same year, I hit send on an email with an offer to purchase advertising space on my site.

That one email resulted in $54,000 in revenue in just 24 hours. WHOA! I had never sent an email that made $540, let alone 100x that amount! 

Now, of course there are a lot of caveats when it comes to who my subscribers were, the offer I was selling, etc, but this story is just to illustrate how financially impactful email can be (without a humungous list).

One really important ah-ha moment for me over the years has been to stop focusing on growing my social media followers, and instead, focus on growing my email list (again, more in section #5). Remember, if someone opts into your email list, they want to hear from you and are interested in what you do. Most people subscribe to less than 20 email lists, while the average person follows more than 300 people on social media. Where do you think your messaging has a better chance of standing out? The email inbox!

Section #2 – MailChimp Breakdown

If You’re Just Starting Out With Email Marketing, MailChimp Is The Perfect Option

I proudly used MailChimp as my main email marketing provider for years. Heck, I still use it to this day for smaller projects. Plain and simple, if you’re just getting your feet wet with email marketing you should use MailChimp.

No email provider is perfect, but if you’re looking for the easiest to use email provider, MailChimp is the answer.

Three reasons why you should use MailChimp…

Reason #1 – It’s completely free up to 2,000 subscribers. That’s absolutely FANTASTIC. You may not have 2,000 subscribers, and even if you climb above 2,000 MailChimp is very affordable. You can send as many emails as you want to these subscribers and it costs you nothing.

MailChimp free subscribers

Reason #2 – MailChimp is amazingly friendly to use.
If you aren’t super tech-savvy, MailChimp is perfect for you. Setting up your email forms is straightforward. Their email designer is top notch, giving you some flexibility, but not enough that your emails end up looking like MySpace pages. Everything is very intuitive and well thought out.

MailChimp Campaign Builder

Reason #3 – MailChimp CAN do a ton of complex and custom stuff.
Once you’ve learned the basics, you can jump into email automations, custom HTML, and even some pretty advanced merge tagging, segmenting, and more.

Bonus tip: My good buddy Paul Jarvis teaches a very popular course called Chimp Essentials, where he’s helped thousands of people do more with their MailChimp accounts.

MailChimp advanced features

What are MailChimp’s drawbacks?

A few years ago, I could have listed off a bunch of things… but alas, that’s the beauty of a company like MailChimp: They listen to their customers and add new features (like automations and deeper email segmentation).

The only drawback that jumps out at me is that MailChimp’s customer support is fairly limited with their free account. You only get 30 days of email support and free accounts don’t get chat support. That being said, MailChimp has an incredibly robust “Self-Service Knowledge Base” that answers the majority of questions you may have. If you prefer to know you can reach out to a support person, you’re going to need to pay for MailChimp or look at ConvertKit.

Truthfully, there simply aren’t that many drawbacks to MailChimp if you aren’t doing a lot of complex things with your email marketing.

Main MailChimp takeaway: Fantastic choice if you’re just getting started, want to spend as little money as possible, and don’t care about automations and complex email marketing features.

Convinced MailChimp is right for you? Sign up for MailChimp and give it a shot.

(I am technically using an “affiliate” URL for MailChimp, but their affiliate program is almost worthless… just fyi.)


Section #3 – ConvertKit Breakdown

If You Sell Digital Products And Want Some Features, ConvertKit Is A Great Option

I switched my main (larger) email list from MailChimp to ConvertKit in 2015. When I started to focus more on selling online courses, I wanted an easier way to segment who received what emails. I wanted to make sure customers who’d already purchased a specific product didn’t get future sales emails about it. ConvertKit’s tagging made this SO simple and the switch was a no-brainer.

If you sell digital products like online courses, e-books, etc, ConvertKit was made with you in mind. Sure, you can use ConvertKit for standard email newsletters and announcements, but it thrives as a platform when you’re doing a bit more with segmenting your subscribers.

ConvertKit’s tagline is “email marketing for professional bloggers” and if that resonates with you, you’ll be incredibly happy.

Four reasons you should use ConvertKit as your email provider…

Reason #1 – Your subscriber growth is front and center. I’m honestly surprised more email providers haven’t stolen this way of displaying subscriber growth from ConvertKit. Because ConvertKit doesn’t have “Lists,” they display your signup forms as segments of the subscriber bar chart.

ConvertKit Subscribers Dashboard

Reason #2 – ConvertKit’s form analytics!
This is one of the simplest, yet most powerful features of ConvertKit. You can see how your individual email subscriber forms convert (based on how much traffic sees the form, then actually subscribes). Other email providers have similar analytics, but none of them display it as clearly and susinctly. These form analytics become really powerful when you want to make small tweaks to your forms (text, button text, color, etc) and see what gives you the best email subscriber conversion.

ConvertKit Forms

Reason #3 – Tags, tags, tags.
You simply cannot create too many tags if you’re selling products via your emails. As an example, if you’re selling an online course in an email, you can create a tag based on someone clicking a link in your email. This is super powerful, because you can create a segment of subscribers who are “interested” (because they clicked) and only send those subscribers additional sales emails. You can also allow subscribers to opt-out of future emails using tags and not having to fully unsubscribe from all emails. I’m barely scratching the surface with the power of tags here.

ConvertKit Tags

Reason #4 – A very intuitive email automation builder.
If you’re venturing into the world of email automation, you’re going to love ConvertKit’s take on it. While I do think Drip has the edge in setting up more complex automations, ConvertKit is hot on their heels and they’ve nailed the user experience.

ConvertKit Automation Builder

What are ConvertKit’s drawbacks?

Much like MailChimp, ConvertKit is an ever-expanding email platform and continues to make improvements. Their automation builder is a great example of a newer feature that brings added value to ConvertKit.

Probably the biggest drawback if you’re directly comparing MailChimp and ConvertKit, is that ConvertKit doesn’t have a free plan.

To me, that’s not a bad thing. But if you don’t make money from your email marketing, you may not be ready to use ConvertKit.

That being said, I stopped using ConvertKit as a paying customer, so why? One of the reasons was that I wanted to do a lot more email automation and they didn’t have a solid solution at that time. That’s not really a problem now. The other problem that led me to switch from ConvertKit to Drip was that ConvertKit uses a company called Mailgun to do the actual email deliverability (behind the scenes). I noticed that my email open rates were in pretty heft decline, from 25% to as low as 10%, and had a few friends using ConvertKit say the same thing. Mailgun’s email deliverability didn’t instill confidence. When I switched away from ConvertKit I immediately saw my open rates climb back up in the ~20% range. Maybe things have improved? Maybe it was just my account? Maybe it was something with Gmail blocking ESPs (Email Service Providers)? Hard to know, but I’m just giving you my experience.

Let’s assume ConvertKit (and Mailgun) have the deliverability thing back on track, since ConvertKit’s customer growth has blasted through the roof. You will be extremely happy with ConvertKit if you’re looking for a bit more oomph with your email provider. You’ll also get great customer service at any account level with ConvertKit.

Main ConvertKit takeaway: If you want a bit more control of email segmentation and are getting into email automations, you’re going to love ConvertKit.

If you want to sign up for ConvertKit, you can get 30 days free using my affiliate URL Again, you won’t pay any more money, I just get a little kickback.

Drip Email

Section #4: Drip Breakdown

If You’re Ready For Email Automation and Personalization, Drip Is Right For You

I’m not going to sugarcoat things… Drip is not an email platform for beginners. Heck, I’ve been doing email marketing for nearly a decade and even I get a bit overwhelmed using Drip.

However! Drip is the most powerful and intuitive email provider I’ve ever used. The automations (AKA workflows) are ridiculously customizable and the amount of data you can see (and add*) on an individual subscriber is impressive. While I have less reasons to list below, it mostly because their workflows/automations are reasons 1 through 100!

If you’re looking to take the next step with email, let’s see if Drip is right for you.

Three reasons you should use Drip as your email provider…

Reason #1 – The powerful, powerful workflows (automations). I could talk for hours about all the things you can do with Drip’s workflows: Automatically take a subscriber in and out of a sales pitch based on their actions (as well as bringing them back in again automatically). Updating subscriber custom fields based on emails you’ve sent them (which can help you create a better understanding of who your best subscribers actually are). Auto-pruning cold subscribers from your list, without ever having to think about it. The list goes on and on.

Drip Automation Workflows

Reason #2 – The ability to add custom data to a subscriber.
I mentioned this in reason #1, but it deserves it’s own moment in the spotlight. Being able to create custom fields for a subscriber (and update them with actions in a workflow) is helpful for things like customer lifetime value, purchase dates of products, and much more.

Drip Custom Fields

Reason #3* – Knowing way more about your subscribers and being able to send emails based on their actions.
Having Drip Pro Tools* is a game-changer if you want to promote offers to your subscribers based on what they’ve read on your site, what email courses they’ve taken, where they are in the world, and much much more. I’m showing you an image of one of my subscriber’s tags in Drip. All of the ones that start with “Read: …” are from Drip Pro Tools seeing a subscriber reading articles on my website (which I could then see they have interest in a topic and send them emails about that). Really powerful stuff that I’m only scratching the surface with.

*This is not a built-in feature of Drip and requires paying for Drip Pro Tools, a code snippet created by Brennan Dunn. It’s actually very easy to add the Drip Pro Tools code to your site, but it’s only available in Brennan’s $997 or $1997 Mastering Drip course (which may be well worth the investment for you if you’re serious about email marketing!). 

Drip Tags with Drip Pro Tools

What are Drip’s drawbacks?

If you aren’t using email automations, there’s really no reason you’ll want to use Drip. That’s not a fault of Drip’s, obviously, it’s just worth mentioning right off the bat.

Truthfully, having switched from ConvertKit to Drip, I was spoiled by the friendly display of analytics in ConvertKit. Drip can show you some of the same analytics (like, subscriber conversion by sign up form), but you have to set up some weird workarounds and it’s almost as if analytics were a complete afterthought in Drip.

Email automations are Drip’s bread and butter. No doubt about it. I’ve said it many times, but if you live in email-automation-land, you’ll love Drip.

I also want to mention that Drip’s customer service has been extremely solid, especially during a short period when this site got list-bombed (long story, for another day, but it wasn’t any fault of Drip’s). They respond quickly. Are helpful. And are almost always available via live chat.

Main Drip takeaway: If email automations are your thing and you’re looking for an advanced email platform, you’ll be very happy with Drip.

If you want to sign up for Drip, you can get a free trial of any level account using my Drip affiliate link. And just a reminder, you don’t pay more if you use my link, I simply get a small kickback.

Growing Your Email List

Section #5: Tips For Growing Your Email List

Growing Your Email List The Right Way

The most important tip I can give you when it comes to getting more subscribers and growing your email list is: Tame your ego.

Having a “big” list is absolutely meaningless if that isn’t serving your business needs and providing value to your subscribers. A few years ago I deleted an email list of 25,000. Yes, that’s twenty five thousand. Why in the world would I do that!? I built a list with the goal of having a big list, not trying to find the right subscribers who matched my business objectives.

I know tons of people who make great money (over $100,000 per year) with a list of 2,000 – 3,000 subscribers. Sure, that may sound like a lot to you if you’re just getting started, but those folks put in the work just like you need to.

If you’re a smart cookie and you know you don’t need the biggest list ever, you just need enough subscribers, then these tips will help you.

Three tips to help you get more emails subscribers…

Tip #1: Your email opt-in forms should clearly explain why someone should sign up for your email list. Don’t just slap a form on your website and have it say “Join My Newsletter.” People are discerning about who they give their email address to these days. You have to give them a reason, a problem your email solves, as to why they should sign up. This is my buddy Paul Jarvis’ signup form. Not only does he share why you should sign up, but the style of writing also will attract or detract subscribers. (The countdown timer to when Paul’s next article gets sent is a fun little recent addition I like.)

Paul Jarvis -

Tip #2: Giveaway your best content on your website (and think about holding some back).
It gets exponentially easier to get people to sign up for your email list when they can read articles or posts from you that will give them an idea of what you write about. If you write helpful content, guess what? It’s a much easier decision for someone to subscribe. I don’t use the second part of this strategy: Holding some content back for email subscribers only. But I used to, and Mark Manson has built an extremely passionate audience doing it.

(Sorry for the NSFW language below.)

Mark Manson

Tip #3: Don’t have much traffic to your site? Write an amazing piece of content for someone who has an audience like the one you want to reach.
 This is affectionately called “guest posting.” Invest the time write a really helpful article for a site that accepts guest posts. I’ll let Ramit Sethi tell you more about this as well as some great additional thoughts about growing your email list:


Please avoid these email list growth tactics…

❌ Pop-ups, slide-outs, and exit intents oh my! We get it. You want to build an email list. But guess what types of subscribers opt-in to all the flashy things you throw on your site? People with a short attention span. The same types of people who stop opening emails after the first week or two (because they’re off to the next shiny object). If you have to pick one of these, I’d say go for the exit intent, because it’s the least obtrusive.

❌ Buying an email list: Don’t do it. Just don’t do it. Even if the list is in your “industry” it’s not going to be worth it. Grow your list on your own, so that it’s completely yours (and you know folks wanted to opt-in).

❌ Doing ALL the giveaways, downloads, and cheatsheets. I’m all for the very occasional giveaway, but it needs to be focused on your business and the type of person you want subscribing. Free downloads and cheatsheets are… alright, but, everyone does some version of them. How can you think about giving a potential subscriber way more value that will surprise them?

Make money from an email list

Section #6: Tips For Making Money With Your Email List

Making Money From An Email List Requires Trust

You know how compounding interest works, right? Over time, you make more and more money when you invest money and let it grow. The same thing can be said for a healthy email list that drives solid revenue for your business.

Think about every email you send as an investment in the trust you’re creating with your subscribers. The more valuable stuff you send, the more trust you build.

Once you have that trust, it’s important to sell the right way via email.

Three tips for making money with your email list…

Tip #1: Be patient. Think of going for the sale with your email list like going on a date. You don’t go for a home run right out of the gate* do you? That doesn’t work. Instead, you slow play things a bit. You earn the right to go for a home run once you’ve put in the right amount of work. Selling with your emails uses the same principles.

*I do have one caveat tip to this advice, but you’ll want to test it (or decide if it’s right for you). That caveat is to offer some sort of awesome deal right after someone subscribers. This is the time when they are most interested in you, and you can capitalize if it feels right. I wouldn’t try to sell a high-dollar product right away, but a discount book, or bundle of digital products, can work really well. This is definitely something to test for your own site/list.

Tip #2: Learn how to write a good sales email and don’t be afraid to send sales emails. I have an entire other article that’s focused just on writing a great sales (or launch) email. You want a good mix of personality, relate-ability, and most importantly, to show that the thing you are selling solves an actual problem for your subscriber. Hopefully the problem you are solving with your products relates to why they signed up for your email list. If not, you might be building the wrong email list.

If you’re tired of feeling completely lost when it comes to writing sales emails, I’ve got you covered! Read my 7-Step Process For Crafting The Best Launch Email article and you’ll have a proven system you can use over and over again.

Tip #3: You can’t send just one sales email. Listen, no one wants to feel like they’re overselling. But you have to remember that your subscribers are busy. Their attention is pulled in a million directions. One sales email is never going to be enough to bring their attention to what you’re selling. There’s no one-size-fits-all to how many emails you should send, you should test a few sequences of sales emails and see what works/feels right for you/your audience.

Here are a few additional articles about sales and selling…


Final Thoughts

Section #7: Final Thoughts

Final Thoughts On Picking The Best Email Service Provider And Using Email For Your Business

Discovering the right way to do email marketing was a game-changer for my online business(es). I used to think about email marketing as a simple broadcast message I’d casually send whenever an idea struck me. When I discovered the power of sending consistent, helpful emails to my subscribers (and attracting the right subscribers), it was like an entire new world opened up.

Email marketing gives you an amazing opportunity to directly connect with people around the world and to deliver consistent value to their inboxes.

If you needed a quick refresher of the three email service providers I talked about earlier:

  1. MailChimp: Great if you’re a beginner and budget-conscious.
  2. ConvertKit: Perfect if you sell digital products and dabble in automation.
  3. Drip: If complex email automations are your game, you’ll love Drip.

And here’s a quick TL;DR chart I put together comparing MailChimp vs ConvertKit vs Drip:

MailChimp vs ConvertKit vs Drip Comparison Chart

One last thing: When it comes to picking the right software you can always switch from one to another without issues. Every platform allows you to export your subscribers and take them with you wherever you go. You’ll always need to redo your sign up forms and actual emails (and automations), but most services offer free migration of that stuff.

Books I’ve Read, with One-Sentence Book Reviews and an Emoji Rating System

December 2, 2017

A few years ago I was completely allergic to reading books. Not medically allergic, I just didn’t want to invest the time nor did I see the value of flipping through pages of writing.

I was young and dumb. These days, I average reading one book per week, and wanted to create a place where I could share the books I’ve read with simple one-sentence reviews of them (including a fun emoji rating system!)

Feel free to bookmark this page and revisit it often 👍🏻

Here’s the highly advanced emoji book rating system I’ve created:

  • Books with a green highlight box are MUST READS!
  • 😎😎😎 means you should DEFINITELY read it
  • 😎😎 means I really liked it
  • 😎 means I recommend it
  • 🤧 means you should skip it
  • 😶 means I couldn’t decide (deal with it)
  • 🕵️ means I’m currently reading it

Jason Zook Reading List></p>
<h4>This page is organized by year, with the most recent book I’ve read, or am in the process of reading, at the very top.</h4>
<p>I’m ALWAYS up for great book recommendations! Please make sure to search this page for a book you might want to recommend. If I haven’t read it yet, <a href=shoot me an email or a tweet at me.

Disclosure: Most of the links below are affiliate links. You don’t have to use those, but I get a tiny kickback from Amazon if you do (and it doesn’t cost you any extra!) Also, I read 99% of books on the Amazon Kindle Voyage and love it.

Let the one sentence book reviews begin…

Books I’m Currently Reading!

The Long Way to a Small, Angry Planet, by Becky Chambers (Still Reading 🕵️)

I’m currently reading this book so I haven’t written a one-sentence review of any kind yet, but when I finish the book I’ll review it and move it to the read section!

Profit First, by Mike Michalowicz (Still Reading 🕵️)

I’m currently reading this book so I haven’t written a one-sentence review of any kind yet, but when I finish the book I’ll review it and move it to the read section!

George Lucas: A Life, by Brian Jay Jones (Still Reading 🕵️)

I’m currently reading this book so I haven’t written a one-sentence review of any kind yet, but when I finish the book I’ll review it and move it to the read section!

Books “On Deck” on My Kindle

Start, Love, Repeat – Dorcas Cheng-Tozun

Dark Age (Red Rising series, Book 5) – Pierce Brown

Final Girls – Rylie Sager

The Flinch – Julien Smith

Nightingale – Kristin Hannah

The Life You Can Save – Peter Singer

The China Study – T. Colin Campbell and Thomas M. Campbell II

The Knowledge – Steven Pressfield and Shawn Coyne

Winners Never Cheat – Jon M. Huntsman

Life – Keith Richards

Memories, Dreams, Reflections – C.G. Jung


These are the 30 books I read in 2018


It Doesn’t Have To Be Crazy At Work, by Jason Fried and David Heinemeier Hansson – 😎

Let me start this short review by saying I LOOOVE Jason Fried and DHH, but, this book is pure common sense if you work for yourself and have figured out how to prioritize balance between life and work (if you haven’t figured that stuff out, definitely read this book).

Iron Gold (Red Rising Series Book 4), by Pierce Brown – 😎 😎 😎

I’m admittedly phoning in my reviews for Books 2-4 of the Red Rising series because they’re all equally amazing and you should read them!

Morning Star (Red Rising Series Book 3), by Pierce Brown – 😎 😎 😎

I’m admittedly phoning in my reviews for Books 2-4 of the Red Rising series because they’re all equally amazing and you should read them!

Golden Son (Red Rising Series Book 2), by Pierce Brown – 😎 😎 😎

I’m admittedly phoning in my reviews for Books 2-4 of the Red Rising series because they’re all equally amazing and you should read them!

Red Rising (Red Rising Series Book 1), by Pierce Brown – 😎 😎 😎

This is my RECOMMENDATION OF 2018! The Red Rising series kept me captivated cover to cover and I didn’t want to stop reading this inventive and super-unique fiction series!


Small Giants, by Bo Burlingham – 😶

I wanted this book to tell me something I didn’t already know, but having lived the “small” entrepreneurial story for over a decade, Burlingham’s book didn’t have much for me (but maybe it will for you??)

The Healing Self, by Deepak Chopra – 😎

I’ve never touched such an outwardly-focused self-help book, but was pleasantly surprised to have a bunch of my own ideas about life and taking care of your mental health reaffirmed by such a popular figure in our culture.

Me Talk Pretty One Day, by David Sedaris – 😶

I’d heard such glowing reviews for Sedaris’ writing and I simply couldn’t get into it at all – maybe you’ll fair better, but it just wasn’t for me.

Children of Blood and Bone, by Tomi Adeyemi – 😎 😎 😎

Thoroughly, thoroughly (!) enjoyed Adeyemi’s creativity and story unlike any other I’ve read in a fiction book in recent years. I can’t wait for the next book in this series!

Surprise: Embrace the Unpredictable and Engineer the Unexpected, by Tania Luna & Lee Ann Renninger PhD – 😎

I’ve believed in the idea of “surprise and delight” for as long as I’ve been running my own businesses and this book dives a bit deeper into why this strategy is a good one (and how to apply it!)

So You Want to Talk About Race, by Ijeoma Oluo – 😎

As a white male I am well-aware of all my inherent priviledges and wanted to read something specifically about our complex racial climate – lots of solid takeaways and practical mindset shifts from Ijeoma.

Genome, by A.G. Riddle – 😎 😎 😎

This is the second book in the “Extinction Files” series by Riddle and it did NOT dissappoint (much like the first book Pandemic).

Punch Escrow, by Tal M. Klein – 😎 😎 😎

Reeeeeeaaaaaaally enjoyed this book! Super unique premise and, no spoilers, an interesting twist on the idea of teleportation. Great read!

Bandwidth, by Eliot Piper – 😶

I read Cumulus from Piper earlier in 2018 and thoroughly enjoyed it. Unfortunately, this follow up book from Piper wasn’t as captivating and I shut it down after 40% completely. Bummer.

Pandemic, by A.G. Riddle – 😎 😎

After reading Riddle’s Atlantis trilogy I was excited to dive into his newest series starting with this book. I genuinely enjoyed the plot, the characters, and by the end I couldn’t wait to start the next book. Solid read.

Tiger Woods, by Jeff Benedict & Armen Keteyian – 😎 😎 😎

WOW. This deep dive into the life of Tiger Woods was incredible! I could not put this book down and have an entirely different outlook on Tiger and his entire life. Highly, highly recommend this book.

How To Stop Time, by Matt Haig – 🤧

This was one of those books recommended to you on Kindle after you finish another book. I pushed through to 51% completion and simply couldn’t continue on. There just wasn’t anything that hooked me in, even though the premise of the book was pretty unique.

And Then There Were None, by Agatha Christie – 😶

I really wanted to get into an Agatha Christie book but there was just something about it that didn’t suck me in to continue to turn the pages. Maybe I’ll give it a go again in the future?

Panic Proof: How the Right Virtual Assistant Can Save Your Sanity and Grow Your Business, by Jess Ostroff – 😎

I consider Jess a friend and when she asked me to read her book I happily obligded. I don’t need a virtual assistant, however, this book also shares Jess’ story, which I found interesting!

Abandon, by Blake Crouch 😶

You’ll find almost all of Blake Crouch’s books on this reading list because I genuinely love his writing style, yet this book felt more like a horror novel than a suspense novel and I couldn’t get into it. Just wasn’t for me, but maybe you’ll like that kind of thing?

Close To Home, by Robert Dugoni – 🤧

I’ve read every book in the Tracy Crosswhite series by Robert Dugoni and this one fell flat for me. I pushed through to 30% completed and decided to shut it down. Bummer.

Culumus, by Eliot Peper – 😎 😎

I don’t typically gravitate toward dystopian novels, but I first heard about Cumulus on the website TheVerge and I tend to trust their recommendation about anything. It did not disappoint! Really enjoyed this book and am excited to read more from Eliot Peper.

All Over The Place, by Geraldine DeRuiter – 😎 😎 😎

I laughed. I cried (kind of). I snorted while flipping the digital pages of my Kindle. Gerlandine has a magnificent writing style and tells stories like no other. I might read this book again soon, it was that good.


Creative Struggles, by Gavin Aung Than – 😎 😎 😎

You may know Gavin as “Zen Pencils” and have probably stumbled upon one of his comics – I recently found his Bill Watterson comic, which led me to his website, which then robbed me of an hour of my life (in a good way!), and then I purchased this book and read it cover to cover.

All These Worlds, by Dennis E. Taylor – 😎 😎 😎

It’s RARE that I pick up the next book in a series right after the previous one, but that’s exactly what I did with the third (and final?) book in the “We Are Bob” series. I found myself excited to go to bed so I could open my kindle and read through a few chapters each night – riveting, funny, and hard to put down.

For We Are Many, by Dennis E. Taylor – 😎 😎 😎

This is the second book in the “We Are Bob” series and I enjoyed it exponentially more than I enjoyed the first book in the series – I think it was the development of characters and storylines in this book that grabbed my attention and held it tightly from cover to cover.

The Year of Less, by Cait Flanders – 😎 😎 😎

I could not put Cait’s book down – She doesn’t hold back on detailed stories of her battles with addiction and fighting personal demons, as well as sharing her journey with minimalism and figuring out what really matters and what she really values in her life. Read this book!

Manhood: How to Be a Better Man-or Just Live with One, by Terry Crews – 😎 😎

I became a fan of Terry Crews after his role in the movie The Longest Yard where he played “Cheeseburger Eddie” – Nowadays it’s hard to miss Crews and that’s fantastic given all he’s been through in his life and how hard he’s worked to get where he is (I don’t align with his religious beliefs in the book, but they didn’t affect my enjoyment of the stories and life lessons he shared).

The Last Black Unicorn, by Tiffany Haddish – 😶

This is a tough book for me to say you should or shouldn’t read as it’s a combination of funny, sad, and a life completely different from mine (which made it hard to relate to and get into at times) – I’d pick up the sample and make sure you watch a Tiffany Haddish interview or two to get her personality.

We Are Legion (We Are Bob), by Dennis Taylor – 😎

I was at a wedding and met a stranger who was a voracious sci-fi reader so I asked her what her favorite book was and she mentioned the “Bobiverse series” – A super interesting premise for a book (trilogy) that took awhile to get into, but I thoroughly enjoyed by the end.


These are the 33 books I read in 2017


Easy Street (the Hard Way), by Ron Perlman – 😎 😎

Man, Ron Perlman is such an interesting dude! Reading about his winding path through life and celebrity was a definite page-turner (full of laugh out loud funny moments).

Artemis, by Andy Weir – 😎 😎 😎

The much anticipated follow-up novel from the author of The Martian – I gave this book three 😎 because it deserves to be read and was just as good as Weir’s first book… IMHO.

Sleep Smarter: 21 Essential Strategies… a Better Body, Better Health, and Bigger Success, by Shawn Stevenson – 😎

I struggle with getting a good night of sleep and always have – after sharing that fact with the Action Army multiple people mentioned this book and I was surprised by how non-boring it was (although, I was already doing most of the strategies, so no huge increase in sleep improvement).

Desert Places, by Blake Crouch – 😎

I am a Blake Crouch fan and decided to dive into this trilogy, however I will warn you, this series is verrrry dark and is probably best not read right before bed – haha.

Locked Doors, by Blake Crouch – 😶

Second book in the trilogy and it brought some hair-raising twists and turns that I wanted to recommend for you to read, but things get even darker in this book so choose wisely.

Break You, by Blake Crouch – 🤧

The final book in this trilogy really threw me for a loop and mostly because it felt forced, very violent for almost no reason, and didn’t leave me feeling good about life (which… may have been the point, so kudos to Crouch for that).

Masters of Doom, by David Kushner – 😎 😎

This book won’t be for everyone, but if you’re a nerd and enjoyed computer/video games, you definitely remember Doom and the height of its popularity – this behind the scenes look at the “two Johns” who created Doom was a really fun read.

Console Wars, by Blake J. Harris – 😎 😎 😎

As a child of the 90s who played copious amounts of video games on various Nintendos, Sega Genesis, and Sony Playstations, this book was such a cool inside look at how everything went down in the video game console industry (and a great book to read right after Masters of Doom).


Perennial Seller, by Ryan Holiday – 😶

I really dig the concept behind this book, but after reading 50% of it, I couldn’t find a reason to continue to flip the digital pages on my Kindle (so, I guess I’d recommend it, but you don’t need to read the entire book?)

The Atlantis Gene, by A.G. Riddle – 😎 😎

If you’re looking for a new sci-fi trilogy to dive into, this is the one for you – Riddle’s writing is action-packed, has a few twists and turns, and is very imaginative.

The Atlantis Plague, by A.G. Riddle – 😎 😎

I’m typically going in with low hopes for the second book/movie/etc of any trilogy, but this one did NOT disappoint as the plot thickened and the character development continued.

The Atlantis World, by A.G. Riddle – 😎 😎

When I finished the last page of this book I put my Kindle down, looked at my wife, and said: Damn, I wish there was another book in this series! – The third book may be the best in Riddle’s trilogy.

Cradle to Cradle, by William McDonough & Michael Braungart – 😎

I’m giving this book a positive review with a caveat: It’s not a page-turner, but it is a book that makes you think about the things you buy, how those things are made, and why you should think more consciously about your purchasing decisions.

I Can’t Make This Up: Life Lessons, by Kevin Hart – 😎 😎

If there’s one thing I really appreciate about Kevin Hart, besides his hilarious way of looking and talking about life, it’s his honesty about his shortcomings and how much hard work actually goes into success.

Disrupted: My Misadventure in the Start-Up Bubble, by Dan Lyons – 😎 😎 😎

READ. THIS. BOOK. Whether you’re in the “tech industry” or not, Dan Lyons wrote a fantastic book about his experience working at a big tech company (after being phased out of his job as a journalist).


Kid President’s Guide to Being Awesome, by Robby Novak & Brad Montague – 😎

Like most humans, I looooove me some Kid President – I did feel resistance to continue to open and read this book, and I believe it’s because I got what I needed from it in the first few pages.

Becoming Who We Need To Be, by Colin Wright – 😎

This was the second book of my friend Colin’s I (finally) picked up and any book by Colin is worth your time, money, and attention.

Snowbound, by Blake Crouch – 😎 😎 😎

It’s safe to say Blake Crouch is my favorite author – This was one of those book I not only couldn’t put down, but I also had incredibly vivid mental images of the characters from Crouch’s writing.

Run, by Blake Crouch – 😎

I read this book right after Snowbound and while it was good, I think my brain was stuck in the previous story and couldn’t fully enjoy this one – definitely recommend it though!

Surge: Your Guide to Put Any Idea Into Action, by Matt Kane, Steve Garguilo & Sergiy Skoryk – 😎

I woke up one morning to an email asking if I’d write the foreword to a book about taking more action, along with a copy of the book itself – I was skeptical, but as a turned the digital pages I realized this was the book I’d write about action-taking, so I happily wrote a foreword and fully endorse this book!

How to Be Ultra Spiritual, by JP Sears – 🤧

Following JP Sears on Twitter is fantastic, so when I saw he wrote a book I was truly excited and pre-ordered it immediately – Unfortunately, the book couldn’t keep my attention and kind of fell flat for me.

Born a Crime: Stories from a South African Childhood, by Trevor Noah – 😎 😎 😎

Trevor Noah had humungous shoes to fill at the Daily Show and he’s done a fantastic job, which is why I was happy to dive into his book which was just a delight (and amazing to learn where Trevor came from).

Dust, by Hugh Howey – 😎 😎

Dust is the third book in Howey’s Wool trilogy and it was a great wrap-up to a solid (but admittedly long) series of fiction books.

The Things We Wish Were True, by Marybeth Mayhew Whalen – 😶

A book I really wanted to get into, but every time I opened my Kindle and read the words, it just couldn’t seem to keep my attention (maybe it’s worth a shot for you?)

Will It Fly?, by Pat Flynn – 😎

100% truth: I skim-read my friend Pat’s book, but mostly because I have my own personal experience to test my ideas and find out of they’re worth pursuing/launching/etc – I definitely recommend this if you’re just getting started in biz.

Wayward, by Blake Crouch – 😎 😎 😎

Oh hello again Blake Crouch! I read the first book (Pines) in 2016, and for some stupid reason I didn’t just continue with the second book of the trilogy – this series is soooo good!

The Last Town, by Blake Crouch – 😎 😎 😎

I wisen-ed up and dove right in to the third book in the Warward trilogy right after the second one and giddily flipped the pages wondering what would happen next.

Save the Cat, by Blake Snyder – 😎

While reading all these fiction books and finding out so many of them were optioned for big screen adaption, I got really curious to learn more about writing and selling a movie script, which is why I picked up Snyder’s book – It may not be for you, but I found it interesting.

What If?: Serious Scientific Answers to Absurd Hypothetical Questions, by Randall Munroe – 😶

Soooo…. I know I read this book because it says 100% completed on my Kindle, but I couldn’t remember a damn thing about it – I guess that says something? No clue. Sorry. #honesty

The Trapped Girl, by Robert Dugoni – 😎 😎

The fourth book in Dugoni’s Tracy Crosswhite series picked up right where the previous three books left off, filled with small twists, turns, and mysterious events.

Departure, by A.G. Riddle – 😶

This was the first book of Riddle’s I picked up, and I struggled to find interest in continuing to read it – Maybe I’ll give it a go again in the future?

Essentialism, by Greg McKeown – 😎 😎 😎

I cannot recommend Essentialism enough as it’s a wonderful way to think about life and business, no matter where you are on your journey (this was my second time reading it).


Eating Animals, by Jonathan Safran Foer – 😎 😎 😎

LIFE CHANGING BOOK ALERT! I’m not joking, Foer’s book put my wife and I on a path to plant-based eating, and I’m so glad I pushed through a book that was hard to read at times (but VERY important) – please read this book!



These are the 45 books I read in 2016


To Pixar and Beyond, by Lawrence Levy – 😎

I’d read Creativity Inc but was intrigued by this book to learn more about Pixar’s business, the crazy Disney contracts, and unique stories about Steve Jobs.

Ego is the Enemy, by Ryan Holiday – 🤧

I loved loved loooooooved Holiday’s book The Obstacle is the Way, but didn’t love love loooove this one (military history doesn’t inspire me).

Total Recall, by Arnold Schwarzenegger – 😎😎

Like him or hate him, Arnie has had a pretty crazy life and I appreciated learning more of it from the Austrian horse’s (honest) mouth.

Bird by Bird, by Anne Lamott – 😶

I could never write a book as eloquently written as this book and that intimidated me and made it hard to finish (just telling the truth!)

My Sister’s Grave, by Robert Dugoni – 😎😎

I found this book on Kindle Unlimited for free and decided to see if a book with 12,500+ positive reviews could live up to the hype — and not only did it live up to the hype, it sparked my interest in fiction books.

Her Final Breath, by Robert Dugoni – 😎😎

This is the follow-up to My Sister’s Grave and it did not disappoint, if anything, it appointed and appointed really well!

The Clearing, by Robert Dugoni – 😶

I’m not sure if I got burnt out on fiction by reading too many fiction books back-to-back, or maybe just the character in these books, but it took me way longer than it should have to finish the third book in this series.

Lucky Bastard, by Joe Buck – 😎😎

As a fairly big NFL fan, I’ve heard Joe Buck’s voice and seen his face on TV quite a bit, when I saw he wrote a book and was going to talk about all the things he couldn’t talk about on TV, my interest was piqued and rewarded (great job Joe!)

Thanks For The Money, by Joel McHale – 🤧

The subtitle (How to Use My Life Story to Become the Best Joel McHale You Can Be) is the absolute best part of the book and I find Joel McHale funny in movies and TV.

The Fold, by Peter Clines – 😎

This was another Kindle Unlimited find and I was pleasantly surprised by the creativity of the story and the ease in which I tore through this book.

The 13 1/2 Lives of Captain Blue Bear, by Walter Moers – 😶

I heard about this book on a podcast and I was really excited to give it a go, but alas, as much as I loved the visuals in the book I simply couldn’t get into the story for some reason.

Dark Matter, by Blake Crouch – 😎😎😎

I found this book in an article on The Verge about upcoming sci-fi books and really REALLY enjoyed this book (more from Crouch in a minute).

Unsubscribe, by Jocelyn K. Glei – 😎

I’ve been able to get a solid grip on my use of email before reading this book, but it’s a GREAT refresher and an important read if you feel like your email inbox controls your life.

Rework, by Jason Fried and DHH – 😎😎😎

This was my FOURTH time reading Rework and the treasure trove of information is always a delight, this book is a MUST READ in my humble short-book-review opinion.


Scrappy Little Nobody, by Anna Kendrick – 🤧

I really wanted to enjoy this book, but I just never felt a strong connection to the words on the pages — sorry Anna (since I know you read my site – haha).

Originals, by Adam Grant – 🤧

Since these are my book reviews, I’m just being honest, but I get bored quickly with books that have 1,000 examples from other people and nothing from the author’s experience.

Act Accordingly, by Colin Wright – 😎 😎

I consider Colin a friend and for some odd reason had never picked up one of his books — I’m proud to say this was a very insightful read and I’ll be consuming many more books from that well-coiffed Colin guy.

Shoe Dog, by Phil Knight – 😎 😎 😎

I’ve been a Nike fan my entire life, but I, like many people, took what the media was saying about Nike at face value and was happy to read the perspective and stories straight from the shoe-wearing horse’s mouth.

The Subtle Art of Not Giving a F*ck, by Mark Manson – 😎 😎

I thoroughly enjoy Mark Manson’s writing (especially this piece) and was happy to purchase his book and enjoy a much longer-form read from him. Even though I do a pretty good job of not giving a f*ck, if you don’t do a good job of that you should read this book.

The Girl With The Lower Back Tattoo, by Amy Schumer – 😎

You either enjoy Amy Schumer’s humor or your don’t, and I laugh out loud at all her vagina jokes so it’s a win for me!

Shift, by Hugh Howey – 😶

The second book in the Wool series, and while there were some good parts, I found myself thinking it didn’t quite hit the mark that Wool did.

Pines, by Blake Crouch – 😎 😎 😎

Blake Crouch is back and I was pleasantly surprised by how much I enjoyed the first book in the Wayward Pines series (probably not shocking to those of you who read this series years ago).


Talking as Fast as I Can, by Lauren Graham – 😎 😎

My wife read this book next to me in bed and laughed out loud almost every single time she read it so I knew I had to give it a read even though I’ve never watched Gilmore Girls — Lauren’s writing was LOL-worthy, but I could see how this book wouldn’t be for everyone.

“Surely You’re Joking, Mr. Feynman!”, by Richard P. Feynman – 😶

I really wanted to enjoy Mr. Feynman’s book and I certainly did enjoy parts of it, but it felt like it took me forever to finish and I was never super excited to pick it back up and keep reading.

Creativity For Sale, by ME – 😎 #noshame

Yes, I read my own book again in 2016, but it was for good reason because I was working on my second book — truthfully, my first book was a first attempt at writing and it’s not stellar, but I’m still damn proud of it.

No One Wants To Read Your Sh*t, by Steven Pressfield – 😎

Apropos to have this listed right after my own book, probably, but this one was a quick read and had some solid nuggets of wisdom in it.

Wait But Why Year One, by Tim Urban – 😎 😎

This was the first year I’d read anything from Wait But Why and I’m angry with myself that it took me this long to do so — If you haven’t read ALL of Tim’s articles, this is a great place to start.

The Elon Musk Blog Series, by Tim Urban – 😎 😎 😎

Listen, the entire world has a boner for Elon Musk, and I’m no different, but I really loved buying the Kindle version of this blog series and supporting Tim’s efforts again.

Deep Work, by Cal Newport – 😎 😎

This book has a terrific message that anyone running their own business or working on creative ideas should read and focus on (heh).

The Life-Changing Magic of Tidying Up, by Marie Kondo – 😶

Marie’s book has an astounding 12,000+ positive reviews and I decided to give it a go — it wasn’t a page-turner, but it made me feel better about my pre-existing tidying OCD.

American Gods, by Neil Gaiman – 😎 😎

This book came out 10 years ago and I had only heard about it because it was becoming a TV show that looked interesting, the book did not disappoint and was a super unique story and fun read.

Tokyo Vice, by Jake Adelstein – 🤧

I just could not get into this book and I have no idea why, I tried and tried and tried and finally had to quit.

West Coast Modern, by Zahid Sardar – 😶

Saying I “read” this book is a bit of a stretch because it’s more of a picture book, but I still enjoyed it and you might too if modern architecture tickles your fancy.

Born Standing Up, by Steve Martin – 😎 😎

I was never a fan of Steve Martin’s style of comedy, it just doesn’t make me laugh, but I thoroughly loved every page of his story and learning more about his journey and how hard he worked in his career — a really well done autobiography.

Sick in the Head, by Judd Apatow – 😎

I’m going to give this book my recommendation, but with the caveat that I did skip a bunch of the interviews because they were uninteresting interviewees (to me), that being said, the style of this book was really cool and it was awesome to learn how dedicated Judd was to soaking up the experience of successful comedians as a teenager!

Party of One, by Dave Holmes – 😎 😎 😎

True story, Dave Holmes and I met for coffee/breakfast in 2010 — He was such a nice guy and I ordered his book the minute he said it was available (and enjoyed every single page, especially the real story of Dave’s MTV “life”).

Think Like A Freak, by Steven D. Levitt and Stephen J. Dubner – 😎 😎

I 100% consider myself a freak and after reading Freakonomics last year, was happy to pick this book up and turn the pages.

A Supposedly Fun Thing I’ll Never Do Again, by David Foster Wallace – 😎 😎 😎

Another author that was well-acclaimed that I had never read anything by, David Foster Wallace’s writing style really resonated with me (and makes me laugh out loud) and the story of his experience on a random cruise ship was hilarious.

Kanye West Owes Me $300, by Jensen Karp – 😎 😎 😎

My wife and I found Jensen Karp’s podcast (Get Up On This) on a road trip a few years ago and he’s been a favorite (funny) person to follow on Twitter — When Jensen started talking about his book and his story of becoming a semi-famous white rapper, my interest was piqued and I read the book in one sitting.

Jim Henson: The Biography, by Brian Jay Jones – 😎 😎

My buddy Matt is back with another recommendation and this was a really interesting book about the life of Jim Hensen (heads up, it’s a long read).

Chuck Amuck: The Life and Times of an Animated Cartoonist, by Chuck Jones – 🤧

After finishing Jim Henson’s biography I jumped into Chuck Jones’ autobiography and simply didn’t have the same enjoyment or excitement to continue to turn the pages.

One Great Shoe, by Zack Schonbrun – 😶

This was a shorter book I found on Kindle Unlimited that told the story of the shoe brand AND1 that I was a HUUUUGE fan of as a kid, very interesting read for a very niche audience.

Ghost in the Wires, by Kevin Mitnick – 😎 😎 😎

This book was ABSOLUTELY FANTASTIC, although a bit nerdy, I hadn’t heard of Kevin Mitnick or his story of being on the FBI’s Most Wanted list in the ‘90’s — a must read in my opinion.


These are the books I read before 2016


Anything You want, by Derek Sivers – 😎 😎 😎

CANNOT RECOMMEND THIS BOOK ENOUGH!!! You can read Sivers’ book in one sitting and every line in it is quotable. Read. This. Book.


Yes Please, by Amy Poehler – 😎 😎 😎

I was 25% through reading this book on my Kindle when my wife and I decided to listen to the audiobook version on a road trip, and I couldn’t be happier we did! The pudding metaphor was LOL-worthy!

Essentialism, by Greg McKeown – 😎 😎 😎

This was the first time I read this book and it was suuuuuch a great way to think about how you focus your time and energy (whether in life or business) – Read this book!

The Martian, by Andy Weir – 😎 😎 😎

Such a great book, but you probably already knew that – feel free to listen to a full podcast episode where I gush about Andy Weir’s book with my BFF Paul Jarvis (who is also featured here twice as an author).

Freaks Shall Inherit The Earth, by Chris Brogan – 😎

As a proud “freak” I was honored to be mentioned in Chris’ book and enjoyed reading stories of other featured freaks – let your freak flag fly!

Freakonomics, by Steven Levitt & Stephen Dubner – 😎 😎

Speaking of freaks… I had heard great things about Freakonomics and decided to pick it up – it did not disappoint and was a really interesting read.

My Family and Other Animals, by Gerald Durrell – 😶

Mr. Durrell’s book is highly touted, well reviewed, and was personally recommended by a friend, but it felt a bit too verbose for me and I simply found it hard to get into.

Your First 1,000 Copies, by Tim Grahl – 😶

A very tactical book about, you guessed it, selling your own book – This is a solid read if you’re thinking about writing your own book (or have and didn’t sell any copies).

Linchpin, by Seth Godin – 😎

I really don’t think you can go wrong with any book by Seth Godin, and this one does a great job of helping you understand the power of YOU and understanding the importance of your ideas/business/etc.

The Dip, by Seth Godin – 😶

We’re in the Seth Godin section of my book reviews, and truthfully I can’t remember reading this book and feeling like I had a big A-HA moment (although, re-reading the description makes me want to read the book again!)

Tribes, by Seth Godin – 😎

Still in Seth Godin-town, Tribes was the first book I read that explained the power of community and about finding the RIGHT people to surround yourself with.

Permission Marketing, by Seth Godin – 😎 😎

A must-read from Seth Godin if you’re trying to understand marketing in the digital age, especially if you’re doing an email marketing (although his principles apply to other marketing areas too!)

The Life and Times of a Remarkable Misfit, by AJ Leon – 😎 😎 😎

Even though AJ and I don’t talk all the time I consider him a great and trusted friend who is wise behind his years -This collection of essays is eye opening and FULL of wisdom.

Creativity, Inc., by Ed Catmull – 😎 😎

I am a huuuuge Pixar fan and was excited to read Ed Catmull’s recounting of the early days of the company, of working with Steve Jobs, and how to promote creativity with employees (when I used to have employees – haha).

The $100 Startup, by Chris Guillebeau – 😎

Normally I don’t enjoy a book that’s a collection of stories from other people, as I like to hear from the author and their personal experiences, but I read Chris’s book at just the right time in my life and enjoyed all the stories.

Give and Take, by Adam Grant – 😎

Someone smarter than me has a great quote that says something like: If you don’t help people when you’re just starting out, you won’t help them when you’re rich – Adam Grant’s book dives deeply into that sentiment.

I Will Teach You to be Rich, by Ramit Sethi – 😎 😎

I’d heard good things about Ramit’s book, but the title always made me feel icky – I put that aside while making big changes in my life (my values) and Ramit absolutely nails redefining what “being rich” means.

Rework, by Jason Fried & David Heinemeier Hansson – 😎 😎 😎

MANDATORY READ ALERT!!! I cannot recommend this book enough, whether you work for yourself and want to start your own business, you have a side hustle, or you already own your own biz and want some inspiration.

The Good Creative, by Paul Jarvis – 😎 😎

Paul is my Internet BFF so it’s hard not to blindly recommend his stuff, however, I really do enjoy the way Paul writes and he’s been a big inspiration for me on how I think and write.

Three Simple Steps, by Trevor Blake – 😎

Trevor Blake’s book came at the exact right time for me as I transitioned away from my IWearYourShirt business and was trying to figure out what to do next and how to control my time toward my next business venture.

The War of Art, by Steven Pressfield – 😎 😎 😎

If you’ve heard of this book, there’s a perfectly good reason: Pressfield does an amazing job of explaining resistance, how it affects us in unique ways, and how the heck to deal with it!

Steal Like an Artist, by Austin Kleon – 😎 😎 😎

Between this book and Austin Kleon’s second (up next), I enjoy the message of the content, but I thoroughly enjoy the presentation and uniqueness of the design of these two books (I’d highly recommend buying the paperback version of Kleon’s books).

Show Your Work!, by Austin Kleon – 😎 😎 😎

The follow-up to Kleon’s first book, you cannot go wrong with early of these reads, especially if you grab the actual paper version and bask in the wonderful book layout and design.

Choose Yourself, by James Altucher – 😎

I really enjoy James Altucher’s brutal honesty and vulnerability – Choose Yourself is a great read if you haven’t yet committed to the fact that you are enough and you can do all things.

The Circle, by Dave Eggers – 😎 😎 😎

Before Tom Hanks, Emma Watson, and John Boyega took the big screen to adapt this novel, it was the first fiction book that I tore through without any hesitation (this was also my first realization that a book can be better than a movie).

The Big Leap, by Gay Hendricks – 😶

One of the few times in this list I simply couldn’t remember any big takeaways from a book I read… so… take this “review” for what its worth.

The Essential Calvin and Hobbes, by Bill Watterson – 😎 😎 😎

I’ve read, and own, every Calvin and Hobbes book (including the massive collector’s edition) and I giddily re-read this collection of cartoons while creating a weird morning ritual.

Thank You Economy, by Gary Vaynerchuk – 😎 😎

Of the two GaryVee books I’ve read, this one resonated more with me and is a great read if you have customers and want to build habits to attract (and reward) more customers.

Crush It!, by Gary Vaynerchuk – 😶

In 2009 I thoroughly enjoyed the message of Gary’s first book, but these days, it’s not something I need and I don’t subscribe to the “hustle” lifestyle.

Body of Work, by Pamela Slim – 😎 😎 😎

MUST READ ALERT! Pam Slim is a dear friend and her book Body of Work hit me at the exact right time when I first picked it up in 2013 – a must read on this list!


The Obstacle Is The Way, by Ryan Holiday – 😎 😎 😎

MY MOST RECOMMENDED BOOK! Holiday’s book about reframing the way you think about obstacles helped me overcome personal hurdles in my life and business, so much so that I wrote an entire article about it titled, The Most Important Book I’ve Ever Read.


The Lean Startup, by Eric Reis – 😎

Almost everyone has heard the term “Minimum Viable Product” these days, but if you haven’t, or simply want to understand creating a business in the digital age, read this book!

Everything I Know, by Paul Jarvis – 😎 😎 😎

My introduction to my BFF Paul Jarvis was from a free email course about writing that ended with a pitch to purchase this book – I read it in one sitting, fired an email to Paul about how much I enjoyed his writing and perspective, and the rest is history!

The 22 Immutable Laws of Marketing, by Al Ries & Jack Trout – 😎

I read this book many moons ago and don’t remember much more than this: Everyone should read this book once, whether you’re a whiz at marketing or not (and don’t ask my why that’s what I remember – haha).

The Four Hour Workweek, by Tim Ferriss – 😎

By now EVERYONE has heard of this book, but when I read it in 2007 (as the second book I’d read by choice!) and was just starting my first business, it was a helpful mindset shift away from thinking I needed to work 40-hour workweeks.

The Purple Cow, by Seth Godin – 😎 😎 😎

In 2005, while working at my first 9-5 job Seth Godin’s book ended up on my desk and forever changed my life – Not only did this book give me the permission to want to pursue a career working for myself, but it also helped me understand that being unique and different was an asset, not a liability.



Some overall takeaways from my experience reading nearly a book a week…

If you’ve read this far, then you care what I think about the books I read (which is awesome!) Going from reading ZERO books a year, to almost one a week, these are the things that have stood out to me.

Much like anything else, try new things when it comes to books.

Never in my wildest dreams did I think I would be tearing through fiction trilogies left and right. I felt like reading always needed to be informative, so I naturally gravitated toward nonfiction/business books. But, as I gained more personal experience with business, I realized reading business books wasn’t very fulfilling anymore (and often distracted me from following my own intuitions). I’m really into sci-fi books these days, but in a year, maybe it’ll be romance novels!??

I would love to find more female authors.

It wasn’t for a lack of effort, I simply found books authored by men much quicker and much more recommended. If you have recommendations please share!

I would love to find more comedic books.

I’d never read anything “funny” before 2016 and I quickly realized how dumb that was when I read Amy Schumer’s book and listened to Amy Poehler’s audiobook (maybe I just need to read books by people named Amy?)

Books are a wonderful distraction from mindlessly scrolling through social media.

As someone who is trying to pull away from the majority of social media, I’m finding myself with extra time on my hands that I want to fill with something thought-provoking or entertaining. Yes, I realize I’m waaaaaay late to the book party, but I’m here now, so let’s keep having a great time and not dwell on it.

The Kindle is an amazing invention.

I might be telling you something you already know, but I resisted reading on a Kindle for a long time. Nowadays, I love having all my books on one device that I can take anywhere (and have taken around the world!)

Give books (and lesser-known authors) a chance!

Again, I may be telling you something you already know, but as a former non-reader, I’ve gotten so much value out of the reading I’ve done these past few years.

So… what’re you reading?

The Ultimate Guide to Intentional Living

August 10, 2017

Imagine waking up to a life that energizes you in every possible way. Imagine carefully crafting every aspect of your life (relationships, work, routines, health) in a way that is uniquely designed to make you feel more alive and myourore fulfilled.

That’s what it feels like to live (what we here at Wandering Aimfully call) your brightest life. Your brightest life is the one that allows your innermost, truest, most vibrant self to be expressed.

Your brightest life is the one that allows your innermost, truest, most vibrant self to be expressed.

Your brightest life is the one where you feel free and filled with a sense of joy. The one where you get to the end of each year, looking back on how you spent the majority of your days, and you are filled with a sense of deep contentment and happiness.

It’s one where you no longer dread going to a job that drains you, one where you don’t feel stuck or static any longer, one where you shed every facet of your life that dims your inner light or weighs you down.

Sound too good to be true?

I get it. It sounds like some kind of fantasyland, right? But it’s not. This kind of life DOES in fact exist. It just takes intention and work to get there.

I know because I myself got there through a LOT of trial and error (which I continue to experience and learn from because your brightest life is an ever-evolving target.)

But this is the kind of hard work that is worth doing because it leads you to a life you can wake up and be excited about.

Your brightest life doesn’t land in your lap, though; you have to go out and get it.

How do you do that? Well, you’re doing it! It starts right here, right now, through intention. We’ll be talking a lot about that word throughout this guide because intention is the secret to controlling the outcomes in your life.

Using the steps outlined in this guide, you will begin to view your life as a craft—a way of sculpting your future thoughtfully and creatively through mindfulness, introspection, experimentation and vulnerability.

You likely landed here because you’re craving more out of your life.

You know this is your ONE shot on this earth, and you’re open to a more intentional way of living.

Great! You are exactly who I wrote this (massive) in-depth guide for. I want to share with you every single lesson I’ve learned over the years in my own journey to a more vibrant, satisfying life.

I’ll offer you stories, nuggets of wisdom, and thought-provoking questions and challenges so you can start uncovering the pieces to your own brightest life—beginning today.

PS: Feel free to use the Table of Contents to the right to jump around whenever you like!

Ready to start living with more intention? Let’s hit it.

Not ready to read the whole guide right now? No worries, we can email you the PDF. Just click here to enter your email and we’ll send it your way!


What is intentional living?

Intentional living is making conscious choices everyday to bring about the outcomes and feelings you desire in your life.

Simply put, it’s living a good life on purpose.

Intentional living asks that you recognize only have this ONE precious life, and it matters how you spend each and every moment.

The notion of intention just means with thoughtfulness and purpose, so let me ask you:

Are you thoughtful about how you spend your time and your life? Do you understand the deeper WHY behind the decisions you make and the things you bring into your life?

Practically speaking, for Jason and me, intentional living means constantly checking in with ourselves to see who we are at our most essential core level, what we value most, and how we can design every facet of our lives with those things in mind.

But, before you can truly experience the benefits of living your life more intentionally, there’s one major prerequisite we have to talk about. I call it ownership.

Section one:

Taking complete ownership of your own life

1.1   Ownership is the key to the life you want

What’s the difference between someone who is able to buckle down and turn their dreams into their reality vs. someone who falls just short, never able to fully realize their potential?

That’s what we all really want to know, right? What is this elusive secret to succeeding in your quest to live the life you actually want?

Well, here’s the important point we have to agree on before we go any further:

The secret is YOU. You are the linchpin variable.

There are apps promising to help you stay focused on your work. Blog posts detailing how to start a business. Books to help you be more positive. And those things can be helpful but…

An app is useless unless you own the fact that only you can find the will power within to use it.

A blog post is useless unless you own the fact that your fear is holding you back from actually doing the work.

A book is useless unless you own the fact that you are the source of your negative self-talk.

There’s nothing I can say in this guide, no resources Jason and I can create here on Wandering Aimfully, no catchy phrase I can share on Instagram, that can lead you to the life you want without your commitment to turning those insights into action.

This is where ownership comes in.

Ownership is claiming responsibility for the choices (and outcomes) in your own life.

To me, ownership is the idea that while we are not always responsible for the circumstances that life throws at us or the cards we are dealt, we ARE responsible for how we react to those circumstance in any given moment.

Life is a series of unpredictable questions, but ownership is about accepting that we get a say in how we answer them.

The first time I made this realization, it occurred to me just how many excuses I was making in my life:

  • “I can’t be a designer because I don’t have a formal degree or training.”
  • “My creative voice isn’t as unique as xyz artist.“
  • “I’m a really sensitive person and rejection hits me particularly hard; that’s why I’m not putting myself out there more.”

Those things may or may not be true, but one thing is sure:

I was using these excuses to opt myself out of things I really wanted.

It took me a while to see my self-limiting thoughts were actually my way of choosing the easier route in my life. Yes, I said easier. I know, I know…if you’ve ever found yourself in a spiral of self-doubt, it certainly doesn’t FEEL easy, does it?

If we accept our perceived limitations, we never have to push ourselves beyond what’s comfortable.

But the truth is, if we accept our perceived limitations, we never have to push ourselves beyond what’s comfortable, and that IS the easier choice. It’s the more comfortable choice. It means we never have to rise to the challenge of overcoming those limitations. Of pushing past what we think is possible. Of OWNING the fullness of the life we’re capable of creating for ourselves.

With ownership comes responsibility, and with responsibility comes FEAR—fear of failure and carrying the burden of potentially disappointing ourselves. (We’ll get into fear in depth later on in this guide.)

So we try to share the load by convincing ourselves that other people share the responsibility for our shortcomings (or, on the other end of the spectrum, our successes.)

Maybe that our ex-boyfriend is the reason we doubt ourselves.
That the expectations of our parents make us fear changing careers.
That our kids need all our time and attention and we have no time for ourselves.
That our partner feels insecure when we succeed or shine in a big way.
That our big successes thus far are only due to one mentor or break we had.

And yes, all those things might be true.

But when we divvy up the responsibility of our choices to other people, we give away our full power to create the life we dream of.

“When we divvy up the responsibility of our choices to other people, we give away our full power to create the life we dream of.”

Every great change I’ve made in my life has come from the realization that I’m responsible for the way I live each day. I’m responsible for how hard I work, for how badly I want something.

Only YOU have the power to own your strengths and use them. Only YOU have the power to acknowledge your weaknesses and work on them.

There is nothing more powerful or hopeful than finally taking ownership of your life.

If you’re wondering why you haven’t been able to finally make your vision come to life, it’s possible that you’re placing ownership in someone else’s hands. Waiting for someone to choose you. Waiting for the right tip or trick to come along. Waiting for that switch to flip. Waiting for someone ELSE to change first.

Not anymore.

There is nothing more powerful or hopeful than finally taking ownership of your life.

Are you ready to take full responsibility for your choices so you can start living more intentionally?

If so, then keep reading. Now the real work begins.

Intentional Living Challenge

*Psssst! I have these little challenge boxes peppered throughout this guide! Look for them if you want to actually apply what you’re learning! Your ownership challenge:

  1. Make a list of five excuses you’ve made in the past for not living the way you truly want to.
  2. Next to each one, write down who you’re giving away ownership or responsibility to instead of taking it on yourself.
  3. Then, rewrite a rebuttal to your excuse by taking ownership back into your hands.


  1. Excuse = “I can’t pick up and move to Paris like I’ve always dreamed of.”
  2. Responsibility = “I’m giving away ownership to friends who say I’m crazy for having this dream. I’m giving away ownership to my family who begs me to stay in my hometown. I’m giving away ownership to my possessions and things which make me feel like I can’t pull up roots and move.”
  3. Rebuttal = “I can take ownership of my own life by recognizing that ultimately it doesn’t matter what my friends think because it’s not their life or their decision. My parents want me to stay close out of the love they have for me, but if they truly love me, they’ll support me pursuing my happiest, brightest life. I do have the power to minimize my possessions or change my lifestyle for the next x amount of time to prepare for this move to Paris. I am responsible for making this plan and making my dreams come true!”

Section Two:

Uncovering your core self

Once you begin reclaiming your power and start owning your responsibility for creating the life you want, the next natural question then becomes:

Well, what IS the life that you want?

You may already have the answer right now. Deep down you may see the future you want for yourself and you’re looking for ways to break through and go get it. OR…you may reading this right now with no idea what you want, you just know there has to be something better than this.

Whichever camp you’re in, one thing is certain: there is no one-size-fits-all recipe for a happy life.

There is no one-size-fits-all recipe for a happy life.

The answer to what brings happiness and fulfillment is different for every person, and even different for the same person at different times in their life.

That’s why the foundation to living your brightest life begins with understanding who you are at the deepest level.

This is what I call uncovering your “core self.”


2.1   What is your “core self?”

In my TEDx talk, I speak about this metaphor I have in my head that I like to picture sometimes. I envision every person arriving as a spirit to this world as a unique “color”—a completely one-of-a-kind hue that encompasses the truest mix of our human potential. It represents our unique combination of gifts, talents, personality, likes, and predispositions.

But, as we grow older, the expectations placed on us from other people—society, friends, family, media, etc.—can often dim that technicolor potential. Things like fear and stress and the endless quest for validation start muddying that bright color of ours.

It’s our job to find our way back to that pure, original state: our brightest, most vibrant state of being.

THAT is what your core self represents: the purest, brightest expression of your spirit.

It’s the deepest, truest expression of who you are, separate from what anyone else thinks of you.

Your core self is the part of you that yearns to be free. Deep down it’s begging you to make choices that will allow it to be fully expressed. It’s that feeling in your gut. Your intuition. Your truth. That deeper knowing.

If you learn to listen to it, it WILL lead you to your brightest life. 

But learning to listen to your core self is a skill—one that must be practiced.

I like to think of your core self as a super-charged magnet. There are certain things that it will pull in closer to you, and there are things it will repel away from you. Your job is to learn how to pay attention to those gravitational forces so you can better understand what your core self desires.

Let’s talk about some ways you can begin to uncover who you are on a core level.


2.2   Mining your childhood for clues to your core self

Going back to your early years can be a great way to look for clues about your core self. In many ways, our childhood selves represent the purest version of who we are. If the goal is to find your truest sense of self, one approach is to go back to a time before the world began influencing your identity.

Or, as Danielle LaPorte once said:

“Can you remember who you were before the world told you who you should be?”

“Can you remember who you were before the world told you who you should be?” – Danielle LaPorte

  • Who were you before the expectations of the world came tumbling into the mix?
  • What did you want to be before you know what was considered “successful?”
  • What did you want to do before you learned what was “realistic” or socially acceptable?

For me personally, I was always drawn to creative pursuits as a kid. I used to spend hours upon hours doing arts and crafts projects at our house. I’d take over the kitchen table, or spread newspaper out across our garage so I could paint this thing or try out new art supplies or bring an idea to life. With the freedom of exploration and play I carried as a child, I can see that creating was so clearly what I always wanted to do.

And yet, it took years for me to return to this knowing. I almost abandoned this core part of myself.

Listening to what teachers and other adults were telling me, I grew up thinking that my high performance in school is what made me special. One look at my high GPA and adults would often assure me I was no doubt going to be “successful.” That I would “make a great doctor or lawyer someday.”

Even from a young age, the message was clear: art is just a hobby, not something you should aspire to or cultivate.

Thank goodness the inner kid inside me spoke up when I felt myself headed down a road that wasn’t resonating in my heart. It was pretty early on in my journey down the “traditional career path” when I realized the big wig advertising job I had aspired to was a poor fit for me (more on that later). Thank goodness that inner kid said, “Stop chasing whatever you think being ‘successful’ is. Do what brings you joy instead.”

It took many more of these nagging-voice moments to start unlearning who I thought I should be, but remembering that little girl covered in marker and elated with experimental art projects was the first step to remembering a big part of who I was deep down.

Intentional Living Challenge

Write down your answers to these questions:

  1. How did you spend your time as a kid?
  2. What were your hobbies?
  3. When you weren’t playing with your friends or doing your homework, what did you gravitate towards that made you lose track of time?
  4. How did you spend your time as a kid?
  5. What did you want to be one day?
  6. And more importantly, WHY did you want to be that?


2.3   What makes you feel the most YOU

There’s no rocket science to this one. A great way to figure out who you truly are is simply to ask yourself. Many people struggle to take the time to quiet their minds and go inward and ask: When do I feel the most ME?

Think of the parts of yourself that heavily influence how you show up in the world, the people you surround yourself with, and what you spend your time doing.

For me, creativity is one part of the equation. I find myself drawn to activities where I can express myself, make things and experiment. I love people who are creative and doing something new and interesting. And, if given an empty block of free time, my choice is almost always to use it to create.

But that’s just one part of me. Over the years I’ve peeled back layer upon layer to understand so many facets of what’s at the heart of me. I’m deeply empathetic and sensitive. I’m goofy and light-hearted. I’m endlessly curious. I can be stubborn and defiant.

Each one of these traits is something I’ve uncovered about myself through a multitude of ways: therapy, journaling, travel experiences, readying books, having a creative practice, etc. I’m constantly looking for new opportunities to spend time with myself and get to know myself better.

Which is perhaps one of the biggest pieces of advice I can give you about intentional living and starting to craft a happier life:

Always stay curious about yourself.

In my book, Your Brightest Life Journal, I begin with a chapter on self-awareness that starts with this quote:

“The greatest thing you’ll ever endeavor to study is yourself.”

Never stop learning about yourself. Never stop asking yourself WHY you do the thing you do or WHY you feel pulled to certain things. These are breadcrumbs that will lead you to your truest core self.

2.4   You are full of contradictions and that’s beautiful

It’s important to note here that the code to our core self is usually a mixed bag, often contain seemingly contradicting elements.

For example, at my core, I feel I’m equal parts intuitive AND logical. These opposing forces play out in different ways in my life in business. I may enjoy putting on my bosslady, make-it-happen, practical business hat, but I also enjoy trading it in for my intuitive, sometimes idealistic, touchy-feely artist hat. Both elements feel like true parts of me.

One moment I’ll find myself watching a GaryVee video, lighting a fire in me to tackle my goals with gusto and approach my work with strategy and logic. Then, later that same day I’ll read a post from Liz Gilbert reminding me to return to my truth and to create wholeheartedly, without worrying about what’s necessary “practical” or what will make me money.

Both people inspire me. Both messages speak to me. I find myself benefiting from both perspectives at different moments in time.

Instead of just embracing this complex mixture within my identity, here’s what sometimes happens instead…

I find myself swinging wildly from one end of the spectrum to the other, convinced that one of these sides is the “right” side of the fence to be on. Then, inevitably I feel like I’m somehow cheating on the part of myself that’s still clinging to the other side.

“I need to embrace that I’m running a business here and not view my work so idealistically!”

“NO! I need to return to the purity of making and not put so much pressure on my work to be financially fruitful.”

“NO this is right.”

“NO that is right.”

And before long my brain and my heart feel like they’re literally engaged in some epic version of tug of war. It’s exhausting.

Then, after a couple of deep breaths, I take a step back and ask myself:

What if it’s actually just somewhere in the middle?

We are all complex humans with the capacity to hold all sorts of opposing forces within us at the same time.

“We are complex humans with the capacity to hold all sorts of opposing forces within us at the same time.”

We can be creators AND business owners. We can carry both masculine AND feminine facets. We can believe in striving forward toward goals AND taking gratitude for what we have now.

The struggle only arises in our attempt to create false dichotomies where they need not exist.

Our identities are not either/or; they are YES, AND.

I’m a little bit of Garyvee AND a little bit of Liz Gilbert. I’m deep and light-hearted. I thrive on a mix of still satisfaction and fiery forward-motion. My truth is somewhere in the middle of all that.

And I’m betting yours is too.

The distress and exhaustion of our “struggle” don’t actually come from traveling back and forth between the two ends of our polarities. The distress comes from fighting the urge to travel between the two or judging ourselves for not being more easily categorized. That uncertain feeling comes from pretending that either one is a static solution rather than a dynamic flow.

We have to learn to see this pendulum swing from one end of a spectrum to the other not as a struggle or tug of war, but instead as a dance—a waltz where the passage is fluid and purposeful and graceful.

As you begin to uncover the truth of who you are at your core, be willing to accept the multi-faceted nature of your humanity.

Recognize that your uniqueness actually lies in the combination of your opposing forces. These contradictions are what make you unexpected, singular and, yes, beautiful.

*Challenge: write down a list of 5 “opposing forces” within you that you often waffle back and forth between. Then think about (or write about) how you’re able to possess both opposing forces within you and give yourself permission to embody BOTH.

2.5   Letting go of stories that don’t serve you

Whenever you start doing the work of getting to know yourself better, you inevitably will find yourself getting acquainted with the parts of yourself that you historically are NOT comfortable with. You’ll recognize your brain playing familiar tapes of self-criticism and doubt. You’ll hear stories emerge that you’ve told yourself about your identity for years. Stories like:

“I’m not a creative person.”
“I don’t deserve to pursue a more fulfilling life.”
“I’m not disciplined enough to change my life.”

But here’s the thing. These are in fact just that: stories. They are not written in stone. They can be examined, dismantled and rebuilt into something more positive. Something TRUER.

In my pursuit to uncover my core self, one story I kept slamming up against was this notion that I am weak or fragile. I was such a sensitive, emotional kid and society’s traditional message to those personality traits is vulnerability equals weakness. I didn’t realize just how much this story was affecting different aspects of my life and how I was seeing myself.

As it turns out, sensitivity and emotion IS a part of my core self. But I get to rewrite the story of what that means. It means I’m compassionate. It means I’m open-hearted. It means I’m unguarded. It does NOT mean I am weak.

Once I was able to let go of that story, I was able to fully embody that part of myself that I was afraid to embrace as a result of that story.

What about you?

What stories are you ready to let go of so you can embrace who you actually are?

What negative stories are holding you back from fully embodying your core self? It could be a story about who you are, or who you think you are as a result of things that have happened to you in your life.

Now is the time to do the rewriting. Don’t let doubt or pain or fear define you or claim your identity.

2.6   Practical ways to get to know yourself better

This section has been all about discovering your core self. I’ve given you questions and challenges that will help lead you to who you are at the deepest level.

But, as I mentioned, self-awareness is a lifelong pursuit that takes practice. You have to seek out experiences and situations where you can learn about yourself and then you have to carve out the time, space, and mindfulness to actually listen. Here are some of the ways I recommend you do just that.


I love the app Headspace for doing guided meditations. I find that carving out 15 minutes a day to quiet your mind allows you to more clearly hear the call of your core self when it’s speaking to you.


I’m a huge proponent of therapy whether you think you “need it” or not. Having an outside party ask questions and uncover insights with you is so valuable. Even when I felt I knew myself through and through, therapy led me to new, deeper insights that helped me see ways I could thrive even more in my life. (Not to mention it has done wonders for taking control of my anxiety and living with more peace in general!)


Writing is a great way to let your subconscious speak to you. Even just committing to a few minutes each morning to get your thoughts out of your head can help you uncover desires and core parts of you that you weren’t aware of. Try asking yourself these questions about who you are and see what answers pop up.

A creative practice

This may not be the case with everyone, but when I’m painting or drawing or even doodling, I’m able to go inward and visit with myself in a way that no other activity allows for. These sessions are often the times when I check in with myself about what I’m feeling and that leads me to a better understanding about what that “core self magnet” is being drawn to or repelled by.


I find that new places and experiences also teach me a great deal about myself. Travel doesn’t have to mean expensive European vacations. It can mean camping for the weekend or renting an Airbnb in a city nearby. Anything that gets you out of your normal routines and daily commitments can help you start to ask yourself those deeper questions.

Section Three:

Defining your core values

The happiness and satisfaction we’re all searching for is attainable, but only once we’re able to design a life based on our unique core values. 

You won’t find sustained happiness through buying what society tells you to buy.
You won’t find sustained happiness through gaining admiration or notoriety.
You won’t find sustained happiness by doing what you think others want you to do.

You will only find lasting satisfaction and contentment when you craft a life that allows your core self to be fully expressed.

As you now know, your core self represents the deepest essence of who you are. Your core values, however, represent what your core self needs to fully thrive.

This doesn’t just mean the big things like family, health, and friendship that nearly all of us want in our lives. These core values also refer to the more nuanced things that vary between each of us.

For example, one of my core values is flexibility. My core self is sensitive and creative, and over time I’ve come to realize that I feel most at peace when I have the ability to mold my environment, my schedule, my daily routine to however I’m feeling and whenever inspiration hits me. My core self loves the spontaneity and novelty this brings, whereas someone else might crave more structure and predictability.

Unfortunately, I can’t just give you one definitive blueprint uncover your values. It’s a highly personal pursuit. It requires time to go inward and develop a deep self-awareness as I talked about in Section Two.

But again, I think it helps to try to think of your core self as a magnet. Notice what that magnet is drawn to and what it’s repelled by. Pay attention to what feels energizing to you and what feels draining. These are clues about what you’re underlying values are. These are indications about what you core self needs to thrive.


Intentional Living Challenge

Here are some guiding questions that might be able to point you in the right direction.
When do you feel free and at peace?
When do you feel stifled and confined?
Where do your thoughts drift?


3.1   Seeking alignment: When your actions match your values and core desires

Now that you have an idea of what core values are, you’re ready for the big key to living your brightest life.

Your brightest life is the one where you are able to live out your core values on a daily basis.

Your brightest life is the one where you are able to live out your core values on a daily basis.

If you can do that, you will find the satisfying life you’re in search of. But, this requires you to make a big shift in how you measure your own “success.”

Intentional living asks you to shift your definition of success from one based on achievement to one based on alignment.

Achievement (the way society typically measures success) is about looking outside yourself for validation.

Achievement says: If I can just do this thing, reach this goal, acquire this whatever, arrive at this arbitrary benchmark, gain this approval…THEN I will be worthy and feel happy.

It’s extrinsically motivated, meaning it relies on validation from other people.

Alignment, however, is completely intrinsically motivated.

Alignment is about matching up your actions with your values.

Alignment is about matching up your actions with your values.

Alignment says: As long as I’m living my truth and walking out my values on a daily basis, I have already won.

No permission from others, no approval, no validation from anyone other than yourself.

This is why values are so crucial for you to define. It gives you freedom from the rat race of “success.” You can stop chasing all the things that lead you farther away from yourself and instead focus on what will fill up the tank of your core self.


3.2   Defending the essential and protecting your core values

Once you define your values, it becomes much clearer to see what things you want to let into your life and which things you don’t.

There’s a book Jason and I both love called Essentialism: The Disciplined Pursuit of Less by Greg McKeown.

The guiding principle of the book can be boiled down to this one phrase: less, but better.

Less, but better is the acknowledgment that eliminating non-essential elements and focusing on a few key things will allow us to more effectively allocate our limited resources (time, money, energy, thought, etc.) to the things that matter most.

As Greg writes:

“…When we try to do it all and have it all, we find ourselves making trade-offs at the margins that we would never take on as our intentional strategy. When we don’t purposefully and deliberately choose where to focus our energies and time, other people — our bosses, our colleagues, our clients, and even our families — will choose for us, and before long we’ll have lost sight of everything that is meaningful and important. We can either make our choices deliberately or allow other people’s agendas to control our lives.”
— Greg McKeown, Essentialism

What he’s saying is that if we don’t get intentional about our values and what is essential to us, we can easily allow the whims of other people and less important pursuits dictate our time and energy. This will inevitably lead to trade-offs we would never make of our own choosing.

For example, let’s say two of your core values are creativity and impact so you set a goal of writing your very first book. You want to complete this goal in the next three months, but you neglect to take a look at your life and define what’s essential in the context of this new goal. Some non-essential time commitments (dinners with friends, favors you said yes to, the monotony of chores, catching up on the latest Netflix shows, etc.) quickly suck up your time and energy, and at the end of three months, you wonder why you’ve barely written any words.

By not defining (and defending) what is essential, your goal is never turned into a reality and your values are never turned into action.

Over time, without the needs of your core self being met, you’ll start to feel the dissatisfaction rise.

When you’re not living in alignment with your core self, you’re not able to step into your brightest life.

It’s not enough to know what your values are; you have to create boundaries in order to protect them.

Defending the essential in your life requires you to say no to many things—things you may even like—so you can say yes to something better.

*Challenge: define your essential. What are the things you’re simply not willing to sacrifice as a trade-off? Is it your health? The pursuit of your creativity? Is it that hour of silence you require in the morning to start your day right? Is it doing work that gives you that fiery stir in the pit of your stomach? Whatever it is, write it down. Once you do that, I’d also encourage you to write down some of the trade-offs you might have to make in order to protect those things. What boundaries do you need to create?*

Section four:

Building a life based on your unique values

Now it’s time to evaluate your current life through the lens of your newly-defined core values.

Think of your core values as your ingredients to living your brightest life. They’re your building blocks, but they still need to be combined to form a tasty recipe that’s delicious and satisfying.

To start shifting your life in the direction your core self desires, you will likely have to let go of the way you’re used to doing things now. You’ll need to:

  • Pick apart your choices to separate out the things you’re doing out of obligation or as a means of chasing achievement-based success from the things you’re doing out of deep alignment;
  • Learn how to constantly tap into your intuition so you can stay on course; and
  • Begin taking a closer look at how you spend your precious resources—time, money, energy.


Letting go of what you “should” do

Living a life of alignment is great in theory, but it’s a little bit messier in practice.

Embracing alignment as your new goal means letting go of what you think you should do with your life based on the opinions of other people, and that’s not always easy.

Staying mindful of this one little word—should—is one way to decipher whether your motivations are fueled by alignment or achievement.

When you recognize your mind or your words including “should,” it’s time to take a look at whether you’re reaching for external validation or actually living from a place of your core values.

Let me illustrate this for you with a story.

It was the summer of 2009 (my last summer before graduating college), and I had landed an advertising internship at one of the most prestigious and recognizable advertising agencies in the world, deep in the heart of Manhattan.

After months of preparation and dedication, I had been accepted as one of six students in the entire country to partake in a highly coveted program. When I got the news, I remember feeling like my dreams were coming true.

In my college advertising program, there was a well-defined path that was universally regarded as the launching pad to a “successful” career in the ad industry. The singular goal was to claim a spot at a big name agency in New York City, working on national and international brands. This would be a clear sign you were on the accelerated path up the corporate ladder. That was the dream, and everyone in my ad program knew it.

Being the overachiever that I was growing up, that dream is what I set my sights on. I pictured myself in my Manhattan apartment, riding the subway to work, learning from the most creative minds in advertising with the biggest budgets on Earth. It seemed like a pretty good dream to me.

June 1st rolled around—Day 1 of my big career in advertising—and I touched down in NYC, bright-eyed and bushy-tailed. I was ready to begin my ascent up the career ladder.

I sat in client meetings where we discussed budgets that blew my mind. There was an endless free supply of M&M’s and Pepsi at my fingertips whenever I pleased (two clients of the agency). I shared an elevator with the CEO of the entire worldwide operation. From the outside, my life was something to be envied.

But inside, it felt anything but glamorous.

Just a week or two into the summer, I started to experience this uncomfortable feeling in my gut (hello, core self trying to talk to me!). My days filled up with deadlines, client calls, and research assignments that were needed at the drop of a hat and in the blink of an eye. People seemed to be constantly scrambling with a sense of urgency that left me on edge.

There was a heaviness hanging in the air that I can’t quite explain—a mingling cloud of expectations, sacrifice, and stress—and it followed everyone around the office. It coated the entire experience in angst. Every day when I walked into that building, the feeling in my gut would sink deeper, and I knew that was my soul telling me this path would bring me farther away from myself, rather than closer to what I ultimately wanted.

I did manage to endure the summer, trying to soak up every ounce of knowledge I could, but I returned to school in the fall knowing the New York ad life wasn’t for me.

When class started back up, my friends asked about my internship with eager, expectant eyes. “How was it? Was it everything you hoped for?”

My first instinct was to lie. To maintain the illusion. Ultimately though, I chose to tell the truth, using a line like, “It just wasn’t for me” or “I guess it wasn’t all it was cracked up to be.”

Despite my nonchalance, I remember in those moments feeling painfully self-conscious of their judgment.

“I bet they think I can’t cut it.”
“They’re probably thinking I’ll never be successful.”
“I can’t believe they wasted such a high profile internship on me.”

The negative self-talk was never-ending. I cared so damn much what people thought about me. I didn’t realize back then just how much my self-worth was tied to the validation of other people.

As much as I knew I hated the feeling of working somewhere that didn’t align with my values, I was still clinging to that feeling of appearing at the top of my game. I mean, this was THE PATH. This was THE DREAM that everyone said I should want and it was within my grasp.

I should want to work with the biggest clients in the world. I should want to work at one of the most decorated agencies in the world. I should want to live in New York—the epicenter of the advertising industry.

But true happiness doesn’t come from following shoulds.

Happiness comes from knowing yourself and living a life that feels aligned with your values. What’s the point in living a life that looks good but doesn’t FEEL good?

The hardest part of shedding my “should life” wasn’t learning to pay attention to my gut; the hardest part was following through on what it was telling me.

The hardest part was letting go of the perception that I was “living the dream.”

Guess what, though? I’ve never regretted it for ONE SINGLE SECOND.

Listening to that voice inside and following it wherever it leads has continued to bring forth even brighter and more fulfilling seasons of life.

I don’t have a Manhattan apartment. I don’t manage million dollar budgets. I don’t play pretend Mad Men every day.

Instead, I live near the ocean where the soothing smell of salt always laces the air. I make my own hours. I set my own deadlines. I go see movies in the middle of the day sometimes because it helps me unwind. I work alongside my cute pup and my husband/best friend.

This is the difference between living a should life and living a GOOD life.

This is the difference between living according to the values of society vs. your own core values.

Intentional Living Challenge

Now the question is…are you living that life? Or are you living the life that you think you should?


4.2   Using your values as a compass guiding you back to yourself

Think of your core self as a wise journey guide that you carry within you all the time. Your core values are like the infallible compass that your journey guide holds. They are your tool for finding your way back to your brightest life in the moments that threaten to throw you off your course.

People often talk about this notion of intuition or your “gut.” We all have that deep knowing that tries to tell us when we’re making choices that are taking us farther away from ourselves, or doing things that aren’t authentic to who we are deep down.

That voice, that knowing, that intuition—THAT is your inner journey guide saying: “Excuse me, can we consult the core values compass, please, because we are getting way off course here!”

Intentional Living Guide

I encourage you to start listening to that voice. It speaks in all sorts of different ways. Sometimes it feels like an ache in your belly, a more obvious whack over hte head (thanks, Rafiki), a nagging feeling that won’t go away, a sense of unease, a tightened chest, or an unexplainable sensation that something is just “off.” In whatever way it chooses to speak to you, try to hear it. Stay mindful of those inner vibrations and get curious when you feel something is out of sync.

Then, turn back to your compass. Look at your list of values (hopefully you wrote those down by now) and ask yourself: Am I truly living out each of these in my life? Am I making decisions that align with these things?

If the answer is no, that’s okay. That’s when you know it’s time to make some changes to course-correct.

The thing about authenticity is that none of us typically knows what’s right or wrong for ourselves until we experience it. We don’t know a career path isn’t for us until we live it every day. We may not know a relationship is toxic until we have time and experience to compare it to. Authentic living is a full-contact, hands-on, roll-your-sleeves-up kind of sport, and you have to know that going into it.

If our only way of discovering the right path for us is feeling our way through it, then we’re bound to make some wrong turns every now and again.

In order to course-correct, we have to speak up and make some changes, which can lead to some hard conversations.

To get to the life that you want, you will no-doubt have to power through some very hard conversations and decisions. It’s simply the price of entry to the promised land of authentic living.

You may have to let your boss know you’re quitting, or tell your loved ones you’re moving, or get terrifyingly honest with a toxic friend, or break-up with a boyfriend/girlfriend.

In those moments you might feel like you’re letting someone down, or like everyone is looking at you like you’re crazy.

But that’s when it’s important for you to remember that any life that doesn’t illuminate your spirit through and through is too small for you.

Any life that doesn’t illuminate your spirit through and through is too small for you.

When you take a step back, do you really think the fear of a hard conversation should have the power to rob you of a life that feels bright and true and full?

Is avoiding an awkward break-up or family argument or an uncomfortable conversation with a boss or colleague worth wondering what might have been?

In my opinion, the answer is no. But how do you actually power through those hard conversations? How do you let someone else know you’re course-correcting and risk disappointing someone?

Well, try starting with telling the truth. Remind yourself WHY it’s important that you make a change, and remember that you only have one, precious life—one opportunity to make the most of your days on this earth. Ultimately, it doesn’t matter how someone else reacts to your truth; it’s yours. A hard conversation will be painful for just a tiny fraction of time compared to a lifetime of living as a shadow of yourself.


4.3 Living your values, even when it’s inconvenient

Sometimes listening to that voice and living out your values means making choices that will disappoint people or confuse them or even make people angry. This is when living out your values will feel highly…inconvenient.

It’s convenient to value truth and authenticity when you don’t have any hard truths to reveal.

It’s convenient to value collaboration and encouraging others when your business is doing well and you’re not feeling self-conscious and in a comparison tailspin.

It’s convenient to value slowness and rest when you’re not scrambling to pay off your credit card.

However, when living your values feels inconvenient, that’s when you need the guidance from those values the most.

“When living your values feels inconvenient, that’s when you need the guidance from those values the most.”

Let’s say one of your values is authenticity and transparency. This shows up most visibly in your business. You don’t like sales tactics that feel sleazy or misleading, regardless of their efficacy.

But what happens when your business isn’t growing or sales are down and you see a sales tactic working for someone else that feels less than authentic? Will you be tempted to sacrifice what you value to get what you want in the short-term? Will the inconvenience of sticking to your guns make you bury your head in the sand?

Or let’s say activism is one of your core values. When you see injustices in the world, the compassion within your core self craves taking action to right those wrongs.

But what happens when staying true to your activist heart means alienating friends or followers that might negatively impact your business? In those situations, will you have the courage to walk your own path, even if it means other people will have their opinions about it?

These are the scenarios you have to be prepared for when you’re carving out your brightest life. You WILL be tempted to ignore your own compass and stray off your path.

What you will realize though is that whatever gains you may receive from ignoring your core values, they will be short-lived.

A feeling of dissatisfaction is sure to follow when you acquire something in a way that goes against what your core self believes, because it doesn’t come from a place of deep truth.

Our core values are easy to talk about, easy to write down on paper, easy to profess…but they’re often anything but easy to live out, especially when things aren’t going your way. It’s easier to hide from yourself. It’s easier to let the tide of your circumstances (and your ego) carry you away from yourself. That is until you finally look around and suddenly you don’t recognize where you are anymore.

Don’t let yourself become lost. Get back to the life you truly want to be living, even if it means making hard choices to get there.

Everything You Need To Know From My Experience With SEO

April 16, 2017

Over 60% of our traffic comes from organic search results in Google, this is what I’ve learned about SEO in that time.

I have a caveat I’d like to start this article with: I’m not an SEO expert. I don’t do SEO for a living. Truthfully, thinking about SEO gives me a headache. But, I’ve learned a few things along the way, most of which are from Matt Giovanisci, that are paying off, and I want to share them with you. Also, just so we’re both speaking the same language, SEO stands for Search Engine Optimization.

Some things you should know about this article before we dive in:

  • The data points below refer to my previous website JasonDoesStuff
  • I used to write and share an average of 50 articles per year (until 2017 when I slowed down)
  • I spend almost no time on my SEO strategy
  • In 2014 my organic traffic (aka: Google traffic) was almost nothing (maybe 5,000 total visitors)
  • In 2015 I got more consistent with my writing and had about 60,000 visitors from Google
  • At the end of 2015 I started learning the basics of SEO (the stuff I’ll teach you below)
  • In 2016 JasonDoesStuff received over 200,000 😱visitors from organic search
  • In 2017 organic search growth continued to over 320,000 visitors!
  • In 2018 JasonDoesStuff became this site (traffic data to be added at year-end)

JasonDoesStuff Traffic Breakdown

I’m going to share every single SEO strategy I know with you in this article. Most of the things I’ll walk you through will seem super obvious and easy. This isn’t rocket science folks, it’s just setting your content up to be read correctly and efficiently by search engines.

TL;DR—How you can start winning at SEO right now:

  1. Write useful and/or entertaining content
  2. Find your focus keyword (meaning the most important term in your article), and use it in your title (H1), headings
  3. (H2/H3/H4), and throughout your post
  4. Research words or terms related to your focus keyword, and pepper them throughout your post
  5. Check back in semi-regularly to update your post (you may need to wait 6-12 months)
  6. Make sure your website looks good on mobile and loads quickly

Ready to venture into SEO-Land? But you know, not super confusing and overwhelming SEO-Land? Let’s do it!


Section one:

Let’s Get The SEO Elephant Out Of The Room

Elephant: Your SEO focus shouldn’t be about gaming some keyword or trying to grow traffic based on a hot topic. Your SEO focus should be on writing content that is useful or entertaining.

Now that we’ve gotten that outta the way, let me remind me that SEO stands for Search Engine Optimization. It does not stand for Search Engine Do-Something-Once-And-Never-Touch-It-Again-Ever.

Google, and other search engines (Bing, Yahoo – LOL, etc), want things to be kept up to date. They want your site design to improve how your content is delivered. They want to make sure your site looks good on mobile devices. They want you want to add helpful updates over time to content you’ve written. This does not mean you’ll have to spend hours every week slaving away on your articles. It simply means you’ll want to check in from time to time and ensure the content you wrote months or years ago is still relevant. Hence, optimization.

SEO glossary of common terms/acronyms

While we’re covering our bases when it comes to SEO, let me also explain a few pieces of the SEO-puzzle that you may not know about (or have heard of them, but feel completely lost):

  • The “H” in H1, H2, H3, etc simply stands for “Heading”
  • H1 – You should only have ONE H1 in your content and it should be the title
  • H2 – Think of H2s as section headings (or chapters in a book)
  • H3 – Think of H3s as sub-headings (or sub-chapters in a book)
  • H4 – Think of H4s as headings that highlight an important point
  • H5/H6 – Much less important and relevant headings
  • Keyword – The one word you’d use to explain the topic of your article
  • Key Phrase – Similar to the keyword, but usually more than one word
  • Title – The title of your article and SHOULD be your H1 tag as well
  • Description – A short paragraph that describes your article (and has the keyword/phrase in it)

Now we’re on the same page with all the fancy acronyms, words, etc, right? Cool. I’ll talk more about a few of those in later sections of this guide (specifically keywords in Section 3). Moving onto the fun stuff…

How I accidentally started ranking #1 for a search results that brought 100,000 pageviews in 2016

We’ll need to hop in our content-writing time machine and go back to 2014. It was nearing the end of that year, and I was feeling completely fed up with social media. I spent every day scrolling through my Facebook feed. I invested way more time than I’d like to admit trying to come up with witty things to share on Twitter. More than 75% of my day was spent in the dark catacombs of social media.

I decided it had to change. I imposed a 30-day social media detox and wanted to see what would happen if I didn’t log in to Facebook or Twitter for a month. You can read the results of my social media experiment here.

Google Analytics data for Social Media Detox articles

(I purposefully removed pages 2-5 for an easier viewing experience—you’re welcome!)

The article I wrote about that experiment ended up ranking #1 in Google for the phrase “social media detox,” which brought almost 100,000 pageviews to JasonDoesStuff.

The four steps I used to get 100,000 pageviews from Google

Step 1: I spent six years building a name for myself on social media.

Step 2: I did something interesting (and maybe a little drastic) in announcing my 30-day detox, and then spent at least an hour per day, for 30 days, writing about it (which would end up in one long article).

Step 3: I stuck with the 30-day detox and the daily writing, and compiled my results into one well-organized article.

Step 4: I published the article it in November 2014, shared it a few times, and then completely moved on with my life.

You may notice that none of those four steps involved SEO. I didn’t have a WordPress plugin that did the SEO work for me (although I now love Yoast and will talk more about it in a minute). I didn’t have someone optimizing my site for SEO.

I literally did NOTHING to optimize my article for search results, other than try to write a useful and entertaining article based on my life experiment.

Which brings us back to a point from the beginning of this article and the first lesson I want to impart on you about SEO…


Section Two:

The Best SEO Strategy Ever: Write Helpful Or Entertaining Content

I am sure some SEO “experts” have a much better plan than the one I’m about to lay out for you. That’s great for them. If you know an SEO expert, please tap them for their knowledge, and start implementing their tactics right away. I’ve heard great things about Moz, but I have never read a single article of theirs.

Don’t focus on the “O” in SEO until you have content to optimize

When my social media detox article started getting increased organic traffic, I decided it could be beneficial to figure out why and reproduce those steps. You know, build an “SEO strategy.”

When you start seeing a little bit of traffic, that’s when it’s time to OPTIMIZE!

The most important thing for me was making sure that my SEO efforts weren’t going to feel like a ton of extra work. Getting more traffic from Google can be a full-time job, and that’s not what I wanted to spend my time doing.

Here’s an additional thought from my friend Matt about not starting with SEO:

“It’s called SEO for a reason. You’re optimizing something that already exists, not creating something starting with optimizing. So it makes sense that you write things with no SEO plan, then if it takes off, you SEO the hell out of it for the best possible results.”

My current SEO strategy that I hope you steal with pride!

Here’s what my current SEO plan looks like, which has helped me grow my organic search traffic from 0 visitors to 200,000 visitors annually:

  1. Have an article topic that I’m very interested in writing about and that I have personal experience with
  2. Write that article, and have my editor make sure it’s not complete crap
  3. Once the article isn’t crap, identify the main keyword or phrase
  4. Search my keyword in or Ahrefs and identify related keywords
  5. Input my keyword or phrase in the article title (H1 tag), and headlines (H2, H3, and H4), and include the keyword in a bolded or italicized sentence
  6. Write a simple headline (we’ll talk about good headlines in a minute) and short description that is NOT clickbait-ey (this is usually the H1 and H2 of my article)
  7. Use the H1 and H2 in the Yoast SEO plugin in WordPress
  8. Publish, share, and update the article when necessary

Those eight steps can be a bit much to digest in a numbered list. Since I care about you, I’m going to break each one down a bit further (with graphs, charts, and supporting PNGs for all you visual learners out there—yay!)


Section Three:

Your Simple 8-Step Plan To Increase Website Traffic

Step 1 to increasing organic traffic – Find an article topic you actually care about

Notice I didn’t say “find an article topic you can rank for.” That’s a losing game. Chasing keywords based on what you could rank for may work in the short term, but you’ll very quickly get tired of writing content if you don’t care about the topic.

Have no clue what topics you should write about? Answer these questions:

  • What do you enjoy doing in life or business?
  • What experiences and stories do you have that you can share lessons from (like this article!)?
  • What do you get asked about the most often?
  • What have you written about before that you can add new perspective to?

Once you have a topic to write about, be realistic about your expectations when it comes to getting organic search traffic.

For instance, this article you’re reading now barely has a chance at ranking for the keyword “SEO” or phrase “SEO Strategy.” Even knowing that, I kept getting asked about SEO strategies I use because I’ve shared in the past that my organic traffic has grown exponentially. That reason was compelling enough for me to spend over 40 hours creating this article (not an exaggeration). Whether this article ends up getting organic traffic from Google doesn’t matter, as it’s content I wanted to share!

Next, use a simple content calendar to keep your content creation consistent

As far as a content calendar goes, I have a very simple Google Spreadsheet I’ve created. I use this on a weekly basis to schedule upcoming articles and keep track of previous articles. You can use my template by clicking here and making a copy (File > Make a copy…) or downloading that sheet as a PDF.

Bonus tip to finding article topics: If you still have no interesting topics to write about after trying to answer the four questions above, text five of your friends and ask them, “What’s something you think I could write an article about?” You may get weird answers, but you may also get fodder for content!

Step 2 — Start ugly and then invest in your writing (aka: hire an editor!)

When I started writing consistently (one article per week) in 2014, I didn’t have an editor. I did have a helpful wife who could review my writing and make sure it wasn’t littered with typos, but we were both busy, so she didn’t always look at my articles before I hit publish. I started ugly.

The first articles you write, or maybe even the articles you’re currently writing, aren’t going to be great. In fact, they might suck.

It’s okay if your content sucks in the beginning! Most of my early articles weren’t very good, and I’m ashamed of them now.

I didn’t have a single article getting organic search traffic before my social media detox article. Instead, my articles got published each week, got read by a handful of loyal readers, and that was it. You may be in the boat I was in in 2014. Again, that’s okay! Sit in your boat (at your desk). Grab your oars (your computer). And just keep rowing (writing).

Remember Step #1? If you’re writing about things you enjoy writing about, don’t worry about getting organic search traffic.

Worry about writing something useful or entertaining.

When your writing does start to get better and starts to bring you results (whether that’s organic search traffic or sales for your business), it may be time to invest in an editor.

It wasn’t until I’d been writing for 14 months, nearly 90 articles and 800,000 words later, that I decided to start paying an editor.

Now, my editor, Chantel Hamilton, is someone I gladly pay to help my writing be as good as it can be.

It may be hard to figure out when the time is right to invest in an editor, but if you’re anything like me and your writing is the driving force of your business, now might be the right time to find a good editor.

Pro-tip: If you’re looking for a great editor, reach out to people you know who write frequently and probably use an editor. You can also reach out to Chantel Hamilton to see if she’s available. If she’s not, she may have someone to refer you to.

Steps 3 & 4 — Identify the main keyword(s) or phrase(s)

Let’s take a trip to Exampletown!

I wrote an article about my experience failing the workout system P90x. If you want to read that article you can do so here, but the gist of it is that P90x isn’t made for everyone, and you need to find the workout system that works best for YOU (which is the same lesson I’ve learned about business, too).

When I originally wrote that P90x article in early 2015, I hadn’t spent a minute thinking about SEO (or the 8 steps I’m outlining here). However, I really enjoyed the message in that article, and my audience seemed to enjoy it as well. I decided it was time to revisit it in August of 2016.

In August of 2016, I remember searching “P90x” in Google and clicking through pages upon pages of results. After about the 9th page of results (who goes that far?!), I finally found my article. However, I noticed something: my headline and description result in Google sucked.

Article SEO preview for P90x

My previous title was: Learn From Failing P90x Too*

My previous description that Google pulled in was: I completely failed at trying to do P90x. But in that failure, I learned some valuable lessons.

*Because of how my blog posts were set up in a previous version of my WordPress website, the title was broken between two separate H1 tags, which is a big SEO no-no. The other H1 tag on my site said “I Want To Help You…”, and Google pulled the second half to come up with this crappy and incoherent headline.

The only saving grace for both the title and the description was that they both had the main keyword in them (by accident, obviously).

So I had this article that I was ready to optimize, what did I do first?

I started by clearly identifying the article keyword and related keyword…

The Keyword: P90x (duhhh)

The article was about my experience with P90x, so P90x, naturally, was the keyword. If you’re struggling to identify THE keyword in your own articles, here are a few questions to ask yourself that might help: When reading your article back, what’s the one idea or thought that stands out? Is there one WORD that the article is really about, like the hero of the story? What’s the hero’s name? That’s your keyword.

The Related Keyword/Phrase: P90x schedule

I found the related keyword by using (I use the free version of SEMrush, by the way). After creating a free account, you can search your original keyword and find other keywords or phrases that are similar and relate to the content you’re writing about. For my article, the phrase “P90x schedule” made sense, and the volume of searches was high enough** to be worth trying to squeeze the phrase into my article.

SEMrush keyword overview

**The volume of searches of a keyword or phrase was something my friend Matt explained to me. It’s unlikely you’re going to rank on the first page of Google with a keyword that has a very high volume (P90x has 110,000 searches), but, you also want to pick the phrases that make sense in the content you are writing about. Focus on keywords with volume of 500 – 5,000 for best chances of winning at ranking for that keyword. I ended up choosing a higher volume related keyword (P90x schedule), but it made the most sense within my article.

After I clearly defined the focus and related keywords (P90x and P90x schedule), I revisited my crappy article title. Luckily, my JasonDoesStuff website had been redesigned (twice) since writing the first article and I no longer had a weird split H1 title tag.

The new title I wrote was/is: I Failed P90x and Here’s What You Can Learn From My Experience

The new description was/is: P90x isn’t for everyone. I only made it to P33x, but I did learn a bunch of lessons along the way about life, business, and the P90x schedule***.

***You’ll notice the keyword AND related keyword/phrase are now both in the description. SEO bingo!

I didn’t use it at the time, but as I’ll talk about more in Step 6, the Headline Analyzer tool showed me the difference in score between my previous P90x headline and the new one:

CoSchedule's Headline Analyzer tool

All of this stuff is great, but what did this SEO work actually do for increasing my position in Google’s search results for “P90x”??

Keyword position in Google Search Console

Yep! I went from a search result position on Page 8 (90ish) in June of 2016 to Page 2 (result #20ish) in March 2017. The search keyword “P90x” is now the 10th organic search keyword on my site, whereas it wasn’t in the top 50 results in 2015 or 2016.

Step 5 — Use your keyword and related keyword throughout your article

My previous thoughts of SEO were: Slap a keyword in the title and, boom, I’m off to the SEO-races! You’re welcome, Google.

Doesn’t quite work that way…

Without having your article read like a repeating-parrot wrote it, you want to include your keyword or related keyword/phrase within all the headings (H1*, H2, H3, H4) and important text (bold, italics, etc).

(Important reminder: You should only use ONE H1 tag per page. If you’re currently using an H1 more than one time in an article or page, you could be getting penalized by Google.)

Note: If your website articles aren’t currently set up with the heading structure I share here, you may need to revisit the styling of your articles and how your headings are being used. Google DOES care about the use of H1, H2, and H3 tags so get your article foundation set up correctly!

If we go back to my P90x article (which you can reference here), here’s how I shoe-horned the keyword in throughout the text of the entire article:

H1 (title) — I Failed *P90x* and Here’s What You Can Learn From My Experience

H2 (first paragraph) — I completely failed doing *P90x*. But in that failure, I learned some valuable lessons about life and business.

H3 — When I popped the first DVD in, starting my *P90x workout schedule*, I expected to start at P1X; Day one.

H4 — Just because another business or person can do something the *P90x* way doesn’t mean that’s the only way it can be done.

Bolded text — So I stuck with Tony and his *P90x workout schedule*. For 33 grueling days, I shoved DVD after DVD into the black box on my TV stand, and I did my “best” and tried my hardest to “forget the rest.”

(The *asterisks* are there just to show you the keywords, they don’t actually exist in the headings or text.)

Reading these headings without the context of the article seems very repetitive and sometimes you might feel like you’re overdoing it with your keywords/phrases. I can promise you that you are not and that Google and the people that read our articles are not reading every single word, sentence, and paragraph.

Setting up keyword/phrases in your headings and throughout your article itself reaffirms the importance and relevance of the keywords and phrases as a reader consumes your content.

What about keyword research? Here’s a real-world example from my buddy Matt of what happens when you find an odd keyword:

“When you do keyword research, you might find weird phrasing. Like, one keyword I was trying to target was ‘sand in pool.’ No one says it like that, but it’s the number one searched phrase for that topic. I had to ignore it, and I went with ‘sand in your pool.’ Still ended up ranking for the keyword!

Or you can get clever, like: Sand in Pool? My 5 year old found sand in our pool, and this is what he said.”

Going through the heading tags and optimizing text with keywords and related keywords is incredibly useful for articles you may have already written.

Like my P90x article, you may have a piece of writing that isn’t ranking at all, but that you enjoy and should be getting more reads. Spend the time to go back through your article and inject your keyword and related keyword (optimize!).

Step 6 — How to write a great headline (or article title)

I want to preface this section by saying I haaaaaaaate clickbait headlines.

37 ways to use cinnamon to sell digital e-books!

This guy lost 200 pounds using only paperclips!

You’ll be shocked at what 12 mountain goats can teach you about business!

Yeah, those headlines? They suck. Even though some sites generate a lot of traffic using clickbait headlines, it’s not something I ever want to do with my content. Plus, have you ever clicked on one of those articles? It’s always a dumpster-fire of information.

Instead of writing a garbage headline, why not write one that goes along with the useful or entertaining content you’re writing?

I genuinely enjoy the challenge of writing a compelling headline for my articles. However, I know that most people don’t. Enter: CoSchedule’s Headline Analyzer tool. I love how simple this tool is: just pop in your headline, and it gives you the score based on some fancy algorithm. The color-coded scoring is really helpful when looking at a list of 10+ headlines (as you’ll see below) to see what ends up being green. (And green is good!)

Examples of headlines using CoSchedule's Headline Analyzer tool

As you can see above, I wrote out 10 different headlines for this article. The one I ended up using (Everything You Need To Know From My Experience With SEO) was the highest ranked (score of 77). However, if I’m using a headline analyzer tool, I do so with a grain of salt. I’ve picked headlines that get scores in the high 50s or low 60s, because I liked those headlines the best.

Like all tools, CoSchedule’s Headline Analyzer isn’t perfect—it may weigh headline scores based on headlines you don’t actually want to have on your site. But it is free (just sign up for an account) and it is super helpful if you have a hard time writing headlines for articles. Use your discretion to pick headlines that score well with these tools, but that also feel like something you’d write (and that your audience would resonate with).

Step 7 — If you use WordPress*, immediately install and use the (free) Yoast SEO plugin

I’m not a huge advocate of WordPress plugins because they can very quickly make your site slow to load, which Google doesn’t love. That being said, the SEO plugin from Yoast is a true diamond in the rough.

(If you haven’t noticed, every tool I’m recommending in this article is free. The Yoast SEO plugin joins the free-and-awesome club. Yay saving money!)

Simply search for the Yoast SEO plugin in your WordPress plugin dashboard or however else the kids are adding plugins these days. Once installed, you can spend time messing with the advanced settings, but I haven’t. Nor have I spent a moment looking at the upgraded features of the paid version of the plugin. Just use the free version, k?

This is how the Yoast SEO plugin works: it hangs out at the bottom of your article and you enter your Title, Description, and Focus Keyword. As a reminder, my H1 is my Title, one of my H2 or H3s is usually my Description, and you know all about the focus keyword by now.

Yoast WordPress Plugin

The great thing about the Yoast plugin is that as you put in your title, description, keyword, and save your settings, it will give you colors telling you how you’re doing (green = good, yellow = okay, red = needs improvement).

Here’s a helpful note from Matt regarding URL slugs:

“If you change the slug (the /name of your URL), you should use a redirection plugin to forward the old slug to the new slug so you keep the SEO juice flowing and there are no 404 page errors.”

The rest is SEO magic. Truthfully, I have no idea how Yoast works or what it’s actually doing to help Google better find my articles. But, it’s working, and when I get all the green dots and lines from Yoast, I know I’m good to go.

Yoast note: I tend to not pay attention to the “Readability Score” that Yoast gives me. My social media detox post, the one that generated nearly 100,000 pageviews in 2016, has red flags, and I’ve never even read what they are. Your article should be readable, which is something you can discern on your own.

*If you don’t use WordPress… well… shame on you! No, just kidding. But I only use WordPress, so I don’t have any recommendations if you use Squarespace, Wix, Weebly, Webflow, or whatever other weird website building tools you’re using.

**If you want to read an in-depth guide to using and setting up Yoast SEO, this is a really good one!

Step 8 — Publish, share, and optimize your article when necessary

As I mentioned at the very beginning of this SEO fairy tale, I don’t like to spend a ton of time thinking about SEO. Once I do all the steps laid out here, I have a very in-depth article sharing strategy that looks like this:

  1. I share the article via my Twitter account (if I remember)
  2. I email the article to my email list (most of the time)
  3. I live my life

Yeah, that’s it.


Section Four:

What About Backlinks? Are They Important?

As you can probably tell by now, I don’t subscribe to all the standard SEO rules. Sure, I use the foundational elements, but I’m not doing ALL. THE. THINGS. That being said, there’s one big topic when it comes to SEO that has a lot of gray area.

Enter backlinks: Should you care?

Simply put, a backlink is a link that someone else puts on their site linking to your article. My social media detox post, which brought in over 150,000 total unique visitors in 2017, only has 59 total backlinks.

Social Media Detox Backlinks

To me, that’s proof that backlinks are NOT of paramount importance. Maybe a few years ago they were, as many SEO experts/gurus want to tell you, but I have the data to prove backlinks aren’t the end-all-be-all of SEO.

Backlinks, and the entire process of trying to convince other website owners to link to my content, just isn’t something I want to waste a single second on. Could it help me? Could getting backlinks take my organic search traffic to 10x of what it is right now? Maybe… but at what cost? I don’t want to use the tactics it takes to get people to post links to my articles on their sites.

Want people to link to your content? Write great content!

Do I sound like a broken record at this point?

I’ve found that people are way more receptive to linking to your content when they find it on their own or when someone (usually a friend) recommends it to them. You can’t force that. You can’t use some fancy software to trick people into having that happen.

Instead of spending any time trying to convince other people to do things, spend that time improving your writing. Spend that time writing in-depth content like this article that can actually help people.

So, you get it now, right? I don’t worry about sharing and backlinks and all that jazz. I share minimally and still get rewarded by Google for writing good content. Does it sometimes take a year or two? It sure does. But there’s no 2-Day Delivery option for the first page of Google (thanks for nothing, Amazon Prime!).


Section Five:

Why Page (or Site) Speed Matters And How To Improve Yours

Keanu cares about site speed

I wanted to write up a really witty section headline about Keanu Reeves and the (fantastic) movie Speed. Alas, I didn’t, so instead, I just grabbed a GIF of Keanu and we’re moving on with more helpful SEO advice.

I’d never ever run a speed test on my website before January 2017. My version of a speed test was loading my own website and thinking, Hmmm, that loaded slowly…oh well!

My friend Ben Rabicoff introduced me to the world of Google PageSpeed Insights, GTmetrix, and Pingdom. I want to make it SUPER CLEAR that I do not have a list of easy ways you can improve your site speed, because that’s really subjective and based on your specific website configuration. That being said, all three tools (Google PageSpeed Insights, GTmetrix, and Pingdom) will offer suggestions after they scan your website on how to improve the speed.

(Ben, you may not have actually intro’d all of these to me, but you get credit, so enjoy it!)

I would imagine you know which one of these page speed sites you should make happy first?

You said Google PageSpeed Insights, right?

Yes, you did, because you’re smart and you know you want to make the Google-Gods happy first. But I will drop yet another caveat on you: it’s good to strive for a high score, but getting a higher page speed score does not directly correlate to getting more organic traffic (as I’ll share in a moment with my friend Paul’s site).

Google Pagespeed Insights for JasonDoesStuff

This is where I show you how un-perfect my previous website’s PageSpeed score was according to Google’s tests. I could go into detail as to why these scores aren’t totally accurate, but we’ve already spent so much time together in this article. Let’s just say that my buddy Ben helped me do all the right things to optimize JasonDoesStuff for speed, but there were a few flags we couldn’t get Google to ignore.

Your site speed is important, but it’s mission critical

Even with my not-so-perfect PageSpeed score, I wanted to show you how that score doesn’t totally impact Google sending organic traffic your way.

The two delicious pie charts below show my JasonDoesStuff site (left) versus my friend Paul Jarvis’ site (right). We get fairly similar overall traffic numbers, but Paul’s site ranks 87/100 on Google PageSpeed Insights (while my site was a paltry 81/100). My lower page speed score hasn’t affected my Organic Search being a higher percentage of my traffic than Paul’s.

Paul Jarvis and Jason Zook traffic comparison

I promise I don’t bring this up to gloat, I bring it up because you don’t have to have a perfect page speed score to have your site rewarded with solid organic traffic. Google still wants to display the best content it can find, even if the site doesn’t load as quickly as a cheetah (Google’s okay with wounded hippo speeds, too).

Let’s look at a second page speed site, GTmetrix…

JasonDoesStuff score on GTmetrix

Testing your site with a second page speed tool is kind of like going to a doctor for a second opinion. Yeah, you totally trust the first doctor (Google), but jusssst in case he’s having an off day, you get that second, younger doctor’s opinion (GTmetrix).

I cursed myself for not saving one of my older JasonDoesStuff reports from GTmetrix. It wasn’t pretty. I was scoring grades of C’s and D’s. No good! But now I’m rockin’ those Honor Roll grades!

The great thing about any of these page speed tools is that they tell you the exact things you need to address and fix on your site.

While they can’t take the next step and make all the fixes for you automatically, if you have a friend like my buddy Ben, you can pay someone money to lay a great foundation (which you shouldn’t have to pay for again!).


Section Six:

Advanced SEO Tool: Google Search Console

I want to preface this section by saying I hope you’ll use Google Search Console, but don’t stress about it, because it’s kind of confusing and not super intuitive.

With my scary preface out of the way, I included Google Search Console because it’s an INCREDIBLY useful tool. However, as I mentioned, it’s not the most user-friendly or the most actionable tool, so I didn’t want to devote an entire section in the middle of this article. Hence why we’re here at the end, throwin’ it in, like a point-of-purchase cookie (or a pack of gum).

Google actually has helpful documentation on setting up your website in the Search Console, so I won’t bore you with that. I will, however, share another fancy chart with you, because fancy charts:

Google Search Console for JasonDoesStuff

This chart shows the position in Google search results for an article I wrote with the keyword pitch email. And just like the chart says, if you search Google for that keyword*, you’ll see my article in the 2nd or 3rd position:

Pitch Email Google Result

Note about searching Google for your own stuff: Make sure you use an incognito window in Google Chrome, or a separate browser where you aren’t logged in to to your Google accounts. Otherwise, your search results will show you your own stuff first, and not what other people (stranger danger!) see when they search.

This is what I use Google Search Console for 95% of the time. To see where my keywords are being positioned in Google and if they’re increasing.

As a heads-up, you are limited to 90-day history on searches, so you can’t see too far back in time (which is weird, considering most SEO tactics take 6-9 months to see results…)

I will have Matt chime in one last time with a cool trick for finding articles on your site that could use optimizing:

“When in the Search Analytics section, search by impressions and position. Sort by impressions, and find the content that gets a lot of impressions but the position is below 7. That means those article topics (keywords) get a lot of searches, but your content could be bumped up if you do some optimizing. These are content pieces on the cusp of ranking and getting big traffic boosts!”

Based on Matt’s trick, I found three articles I’ll be spending time trying to optimize and tracking the progress of over time (can you guess which one I want to rank higher for the most??)

Using Google Search Console to find posts that need improvement



Things To Avoid Doing That Will Hurt Your SEO/Organic Traffic

All right, let’s wrap things up, but let’s also talk about some important things to watch out for when it comes to SEO. These are a few things that will hurt your chances of increasing your organic visitors from Google. Which means, make sure you don’t do them!

Don’t use pop-ups on your website

For the love of all things holy, just stop using pop-ups. Pop-ups, whether they work are not, are annoying and Google is penalizing sites that use them and not showing those sites in search results as much.

Avoid bait-and-switch headlines/titles

This should be extremely obvious, but don’t write a headline for one thing, hoping to ride the coattails of some hot keyword, but then have an article about something unrelated. Google know what you’re trying to do here, and they don’t like it. Plus, if someone clicks a link to your site from Google, and immediately hits the back button, this is called pogo-sticking, and Google dislikes it.

Stop using heavy-loading plugins or bloated site builders

If you install a bloated WordPress theme (like Divi, for example), it can drastically slow down your website because it has to load all of its features. Google doesn’t like slow websites. Squarespace, unfortunately, is bloated too, even though I still recommend them to folks (something tells me Squarespace will figure out site optimization. They’re big time).

Try to avoid folks hitting your 404 page

In one of the (many) redesigns of JasonDoesStuff, I decided to remove 100+ old articles. I just deleted them. Right in the trash. What I didn’t think about is that those articles were old and had other sites linking to them that I didn’t know about. Luckily, and this is another reason to use Google Search Console, Google sent me an email about these now broken article URLs which were resulting in 404 page errors. Unluckily, I spent 8 hours redirecting all the broken URLs to the best pages on my site possible. So keep 404 errors in mind if you’re deleting old articles, and instead, maybe just leave the old articles alone (or spend time redoing them so they’re awesome).

You MUST improve your website’s mobile (responsive) experience

I could have devoted an entire section of this article to optimizing for mobile, but you should know this by now. If your site isn’t mobile friendly, Google is going to penalize you. Make your site mobile responsive. It’s worth the investment of time and money.

You have all my organic traffic growth and SEO strategies, what are you going to do with them?

Are you going to let your website continue to have great content buried in it? Or are you going to spend the time to set things up correctly?

If you want my action-taking advice:

  1. Make a spreadsheet and list out the top 20-30 articles you think are most important on your site.
  2. Do everything I’ve listed here to those articles.
  3. Track your progress and check-in every couple months to see if you’re making progress and increasing organic traffic to your site.
  4. Live your life and don’t worry about SEO.

I’ll say it one final time:

The best SEO strategy in the world is absolutely worthless if you aren’t writing useful and/or entertaining content.

Focus on that first, along with the foundation and structure of your articles.

Leave everything else to Google. K? K.

How To Build And Sell Your First E-Course

July 16, 2015

As a self-taught designer and a self-made artistpreneur, it’s probably no surprise that I’m a big fan of online learning.

I’m constantly using online courses to acquire or improve my skills with design programs, web design, marketing and web development — all valuable things that I’ve used to build and grow a profitable business.

And I’m not the only one.

With the explosion of information available to us online, I’ve noticed a huge increase in learning resources available to those that want to learn new things over the past few years — just look at the success of sites like Skillshare and

This fact is actually very good news for you and me because as the increase in demand for online learning increases, so does the opportunity for people to make a living by sharing their talents and teaching others.

And I’m not just talking about online courses that are $500+. You can make money with small and affordable classes too.

For instance, since October of 2014, I’ve made over $70,000 in revenue from just ONE $20 online course: the Better Lettering Course.

This revenue stream has been so impactful for my business that I was able to stop taking on client work altogether, something that I didn’t truly enjoy as much as I enjoy building resources for soulful creatives.

Since making this change, I’ve been able to shift my business in a way that I feel is more authentic to who I am. I get to help a lot more people on a regular basis. I get to constantly come up with new ideas and execute on them. I get to enjoy the process of thinking through how to teach a new idea to someone. Overall, I feel freer and more flexible to design my days the way that I want (as opposed to designing them around client deadlines.)

In short, online courses have changed my business and my life for the better.

And I’m hoping they might be able to do the same for you.

Now, I remember what it was like when I started building my first e-course. It was unbelievably overwhelming! I remember thinking… Where in the world do I start?

I’m hoping that this post will be the answer to that question for you.

I’m going to take you through every single step in the process to building (and selling!) your first online course.

Now, while I think this post is incredibly thorough, by no means am I saying it’s exhaustive. Meaning… YOU have to figure out what works for you. If you don’t want to do things exactly as they’re outlined below, well more power to you!

The purpose of this post is to provide you with some structure to simply get started. Ultimately, though, you have to seek out and choose the best resources and processes that feel right for your business.

Just to reiterate: this post is not a “how I got rich on the internetz and how you can too” post. E-courses are NOT a get rich quick scheme.

They take a lot of work to put together, and there are no revenue guarantees. HOWEVER, if you enjoy teaching and sharing your gifts with others on a one-to-many scale, e-courses could be an excellent way for you to create real revenue doing something you love. And that is my ultimate goal — to help you design a business and a life that is as vibrant and authentic as possible.

So, without further ado…. Let’s get into it!


Section one:

Before We Start: Should You Build An E-Course?

Online courses are, simply put, just another way to share information or your skills. They can get a bad rap because some people are sleaze-balls and make crappy things in life. But the same thing can be said about terrible websites, spammy e-books, and blogs with 47 email capture popups. The key is to focus on making something great and something you know will help other people.

My husband Jason and I believe that everyone has something to teach. There’s no doubt in our minds that you’ve cultivated some expertise in your life and you could share that with other people. An online course may be the perfect vehicle for that!

Simple steps to ensure you create a great e-course:

  • Teach a skill you have firsthand experience with.
  • Invest the time and effort it takes to create something of value.
  • Make sure you know your course can help someone (and isn’t just being made for the $$$).
  • Prepare to show up for your students after they purchase and continue to help them.
  • Be willing to constantly improve and update the course as needed

It’s only fair to play the other side of the fence here as well so what are some reasons you shouldn’t make an online course?

  • Creating a new product will distract you from the core mission and foundation of your business.
  • You don’t have much extra time or energy right now to dedicate to building an online course.
  • You’re looking for a get-rich-quick scheme.

Let’s talk about realistic expectations.

As a society, we’re so quick to jump at a new project or opportunity. We get immediately wrapped up in all the amazing potential! But, as with every new thing, the potential is not guaranteed results. Even if you’ve created an online course before, it doesn’t mean the next one you create will be a smashing success.

Wrapping up this section on if you should/shouldn’t create an online course, if you can answer YES to these six questions, then you absolutely SHOULD create your own e-course:

  1. Do I have the time it takes to make something that’s high quality and will actually help people?
  2. Do I have real demand for an online course? Are people already teaching what I want to teach?
  3. Do I really want to make this course or am I just chasing the financial dream someone is selling me?
  4. Do I have a plan for promoting the course after the initial launch?
  5. Does an online course align with my current business offerings?
  6. Am I going to survive (financially) if the course doesn’t make money after the initial launch (or at all)?

If you answered yes to every question—and you must answer yes—then congrats! You should build an online course!

Here’s a quick aside from my husband Jason when he was wrestling with self-doubt before making his first e-course (which, spoiler alert, went on to make $100,000 in just three years):

Oh hello there friend, it’s Caroline’s partner in crime/life: Jason Zook!

When I set out to create my first online course in 2013, I had absolutely no clue what I should teach. I knew I wanted to move away from trading time for money, but I didn’t know where to start. A friend of mine gave me some great advice in the form of a question. He asked, “What’s something you have experience with that you could share with other people?”

My self doubt immediately crept in and told me, Nothing! I’m not special. I’m not a teacher. Why should I create an online course? These thoughts are normal, and they continue to come to the surface every time I think about creating a new online course. The first time around, that self-doubt lasted a couple of weeks before I realized I had quite a bit of experience in landing paying sponsorships for projects. Over 1,600 paying sponsors, to be exact. There had to be something I’d learned during all that experience and some processes/tactics I could share.

And there were! I created an online course called How To Get Sponsorships For Anything. That course was my starting point, and three years later, it’s brought our household $100,000 in total revenue. Take that self-doubt!

There is something unique about you. There is something you know better than most people. You are full of interesting ideas, thoughts, opinions, and experiences.


Section two:

Picking Your Course Topic

No surprises here! Before you start building a course, you’re going to want to figure out what you want it to be about. It’s important that you feel comfortable enough with your topic that you have plenty of information to share on the subject. As a personal preference, I like choosing topics I have some extensive personal experience in so that I don’t have to go off and do a ton of research on my subject; instead, I can simply teach from a place of personal knowledge and experience.

Here are some guiding questions to ask yourself as you brainstorm your e-course topic ideas:

  • What do I have experience doing that someone would want to learn about?
  • What topic gets me excited about teaching?
  • What do I know how to do that I wish more people knew?
  • Can I envision a specific audience that would find this course valuable?
  • Does there seem to be any demand for this product?

Speaking of that last one, let’s talk a little bit about demand.

Now, like I said, building an e-course is no easy task. There is a lot of time and energy that will go into building your course, so you want to make sure that the juice is going to be worth the squeeze, right? You want to make sure that your course topic is something that people will want to learn (and something they’ll pay you for!) That’s where the idea of “product validation” comes in.

Use product validation to choose your course topic

See that dandy email sign up form at the top of this post? With every big blog post that I think could be an interesting product idea, I make sure to include one of those at the top and bottom so that 1) I can start capturing a list of interested people that might purchase a course on that topic, but also so that 2) I can gauge interest on that particular topic. If I put up the blog post and no one enters their email address (or very few do) then I know the juice is likely not worth the squeeze and I move on to the next course idea.

Here’s a post where I talk much more in-depth about how I use product validation to know which product ideas will bring me revenue:  [How To Know Which Product Ideas Will Bring You Revenue]

Sometimes you’ll find that what you think people want, they’re not willing to pay for. For instance, I had this idea for a daily Photoshop tip email and I set up an email capture on a post with other Photoshop tips. It’s been almost 5 months and only 50 people have signed up saying they want that product. To me, the effort to build it wouldn’t be worth the revenue it would likely bring so I scrapped that idea.

Here’s a look at the in-post sign up form:

Product validation is your assurance that you’re spending your precious resources (like time, creativity, money) on something that will bring your business substantial revenue.

The lesson here: Don’t choose your topic assuming that people want an e-course on your subject. Make them prove to you that they want it by requiring them to opt-in somehow.


Section three:

Creating An Outline For Your Course Content

Once you’ve settled on a topic, you want to loosely outline the lesson topics and course content.

At this point in the process, I simply start with a blank Google Doc and start cranking away, typing everything I can think of related to my course topic. In these beginning stages, I’m not worried about lesson titles, the order of content, or even whether a particular thing fits into the course or not. This step is all about getting the knowledge and information out of your head and onto digital paper.

Start with a simple, not-overwhelming, bulleted list

I usually start with a bulleted list and just type out points or questions under the umbrella of my course topic. Once I feel like I have a good amount of bullets, that’s when I take a step back to ask myself what order the information should go in. That’s when I go back through each bullet, cutting and pasting them around until the bullets are re-ordered in the most logical, step-by-step progression.

Remember, you want to think of your course content as building blocks. Ask yourself what basic information might form the foundation for more complicated information. This will help you get clear on the order the course content should go in.

This is usually a good point to walk a friend or peer through your outline to see if it makes logical sense to them. Sometimes when you’re so close to something (hello, you’re likely already an ace at whatever you’re teaching) it can be hard to see the holes in your content — the parts where a newbie might get stuck. Getting feedback could be crucial to spotting those holes early. (Even better, think about how you can get feedback from someone who is similar to the type of person you’re targeting with your course!)

Once you feel comfortable with the order of information, think about how you could organize it further into a course format. Start to pay attention to how information can be grouped together to form lessons, modules, chapters, etc.

For example, the Better Lettering Course is set up as six lessons only, each with a different topic about hand-lettering. The Better Branding Course, on the other hand, is much more in-depth and has a lot more information (27 lessons total.) That could easily be overwhelming to someone, so I’ve grouped those 27 lessons into four modules, each to represent a different step in the branding process. This organization helps make the course content more digestible.

Your lesson here: Come up with a course outline that includes all the lesson topics you want to cover, and organize them in a way that will make sense to someone learning about your topic for the first time.


Section four:

Writing Your Online Course Content

Once you have your basic lesson topics written out and organized, that’s when you want to go back through and fill in content for each section.

You can write as little or as much as you want for each section, but it’s probably a good idea to think ahead a little bit in terms of how you might want someone to experience the course.

Writing is a strength of mine and the way that I organize my thoughts best, so I like to go through and write out each section as if it was a blog post like this one. This approach not only forces me to explore each lesson topic in-depth (making me more prepared when it comes time to record my videos,) but it also allows me to easily convert the course content into an e-book if I want to sell that separately at a later date.

Here’s a screenshot from my original outline document once I went back and filled in the course content. I like to format the Google Doc so it becomes clear to me how to structure my slides once I make them for the course videos:

Now, that might not be the case for you. The idea of writing all the content out for your course might be intimidating or overwhelming, so maybe instead you just want to continue adding bullets and sub-bullet points to your outline to get more specific with your information.

If you know you want your course to be videos with slides (no written portion), then it may not be necessary to write out all of your course content line by line. You could just use your bullets as points on your slides. Do what feels most natural for you so you can set yourself up for success in terms of creating the actually content, which is the heart of your online course.

Your lesson here: Keep adding content to your outline until you feel you’ve successfully written the content of the course in whatever format makes the most sense to you.


Section five:

Create A Brand And Style For Your E-Course

After I have an idea of what the course will be about but before I begin work on actually building the lessons, that’s about the time that I start figuring out an overall look and feel for the course.

I typically go with something that feels somewhat consistent with my umbrella brand (now Wandering Aimfully, previously Made Vibrant), but with a twist so the course has a bit of brand identity on its own. I also always create some sort of identifying logo, along with loose brand style rules so the design of the course remains professional and consistent throughout.

Funny enough, the logo for the Better Branding Course actually came from of a rejected logo concept for a design client. I loved the idea of the diamond being made up of connected points. In the course I talk a lot about how the seemingly different elements of your business and personal story can be connected by a single conceptual thread that forms your brand. The diamond visual was great at reinforcing the content in the course, so I decided to use it in the Better Branding Course logo.

I created a quick little style guide using the MV brand colors (plus that fun pop of purple) and I used this guide when designing my sales page and Keynote slides for each lesson.

In a course with multiple modules, I also think it’s helpful to “assign” a color to each module as a way for students to quickly recall what module a particular video was in or to easily match certain resources with certain modules.

Speaking of Keynote slides, that brings me to the next step…


Section six:

Choose Your Teaching Medium

Woohoo! If you make it to this point and successfully create the course content, you will have made it over the hump!

Then it simply becomes a matter of packaging up that content in a way that is easily accessible for your students. That’s what these next two steps are about — figuring out what medium you want to use to teach your course and deciding how to deliver the course content to your students.

Picking Your Medium

When it comes to online course content, I think there are three main ways to teach: video, audio and written content. In both my courses, I use a combination of video and written content, but let’s go over each one to help you decide what you want to use.


Video is my preferred method of teaching because it combines the visual component of images/written content with the ability to add personality and context in your voice.

I’ve seen video used in primarily two different ways: with the teacher on-screen or the teacher off-screen.

If you decided to teach on-screen, the benefit is that your student gets to experience your full personality and engage with you in a meaningful way. They can see the expressiveness in your face as you talk and that goes a long way in getting them excited. If done right, in a professional studio (similar to how Treehouse does their videos or how Marie Forleo teaches in her weekly MarieTV videos) then the result feels professional, high-quality and personal.

As a drawback though, going this route can be expensive and time-consuming because not only do you need the quality equipment to do it well, you also have to nail your lesson scripts.

If you don’t have the cash or access to a professional studio, but you want to utilize the personal feel of on-screen video, you could have a friend with a nice camera shoot you on a colorful, interesting background and think about doing maybe a quick video introducing yourself and welcoming people to your course.

Teaching off-screen, however, can still be effective and can be more affordable if you don’t have access to a professional camera. You can record your voice as you teach with the help of Keynote/PowerPoint slides. This will allow you to edit the audio, meaning that even if you don’t record a lesson perfectly all the way through, you have the ability to edit out your mistakes.

I’ll be honest, either video option is ultimately pretty time-consuming, but in my opinion, it provides the most comprehensive and immersive learning experience.


Think of this option as delivering your course content like podcast episodes. Similar to video, audio allows you to inject your personality into your teaching and gives you the flexibility to edit out your mistakes. However, if you’re trying to teach on a topic that is very visual and relies on things like images for understanding, this wouldn’t be a great route for you.

Whether you decide to go with video or audio, making a small investment in sound equipment like a simple lavalier microphone (lav mic) will go a long way in the perceived quality of your final product.

Written only

If you’re not comfortable in front of a camera or recording your voice, you can always try a written-only course. You could put your course content in daily emails, slide presentations or a series of PDFs. While you may lose a little of that personal connection with your students, the time and money investment are certainly much lower than going the audio/video route, so if you’re on a tight budget, written-only is a good place to start.

Creating Your Lessons In Your Medium

Since both of my courses are primarily video-based, I’ll share with you my process for building and recording my video lessons.

Creating lesson slides

First, I started by taking my written content from Step 3 and using it to build a Keynote presentation.

I love using Keynote because I can easily create Master Slides with branding/typography settings and it makes it really easy to add new slides in the style I want. I also love the image editing tools, and the fact that I can really easily export to PDF, which allows me to offer my students the ability to download each lesson’s slides as a PDF.

I created an “appear” action for each bullet point just because as I talk over the slides, I don’t want students to tune me out in an effort to read the bullets. Instead, the bullets are used as a reference point and the real meat of the teaching comes through in my audio (you can see that in the video lesson below.)

Recording lesson videos

Once I created all the slides for every lesson, then it was time to record my videos. First, I plugged in my lav mic to my laptop to make sure my audio would be better than my Macbook built-in microphone.

Then, I opened QuickTime Player on my Mac, hit File > New Screen Recording, clicked the red record button in the pop-up window, and I clicked anywhere to record the whole screen.  (If you’re using a lav mic, click the drop down arrow next to the record button to make sure your audio input is set to your mic.)

Then, I hit Play on my Keynote presentation to make it full screen from the point at which I wanted to record. At that point, I started talking over my slides and teaching my lesson. As I clicked the right arrow, it cued my bullet points to transition, just like you would do if you were giving a presentation in front of an audience.

Now, I don’t always say things perfectly. Some people might choose to read a script so they know exactly what they want to say minus the ummms and ahhhhs. For me and the style of teaching that I want in my courses, scripts simply don’t work. I want my courses to feel natural and friendly, like talking to a friend over coffee, and so I’m okay to sacrifice a few moments of my silly, unscripted interjections in order to maintain that authenticity.

Luckily, I also have a video editor on hand (my life partner, Jason) who edited all my videos for the Better Branding Course. Jason taught me the basics of iMovie so that I could edit my own videos for the Better Lettering Course, but since there was a lot more content this time around a higher price point, I knew I wanted the videos to be edited by a professional (luckily a professional happens to live under my roof.)

f you decide not to do video, you want to apply the same basic concept of this step to whatever your medium is at this stage. This part of the process is all about formatting your course content in the medium you choose.

If it’s audio, record those lessons as audio files on your computer (and edit, if needed.) If it’s emails, start writing each email in a Google Doc or laying out each PDF in your design program of choice. This step is all about presenting your lessons as they’ll be consumed by your students.

Your lesson here: there are multiple different mediums that you can use to teach your course. Ultimately, you want to choose the medium that you feel most confident with and the one that best communicates what you’re trying to teach.


Section seven:

Deliver Your Course Content To Your Students

Decide how you’re going to deliver your course content and get your course ready for students.

Now that you have all your fancy lessons in whatever medium you want, you have to ask yourself: where is my course content going to live and how are my students going to get their hands on it?

Both excellent questions! Let’s first dive into where your content will live online…

Hosting Video/Audio Content

Video and audio files must be hosted somewhere online before you can make them accessible for consumption. There are a few different ways to make this happen.


My first time around for the Better Lettering Course, I decided to upload my finished video lessons to YouTube and set them as “Unlisted.” This means that only people with the video link (my students) can view the videos, and the video won’t show up in Google’s search results. The course platform I use (which I’ll go into more below) allows you to embed videos, so by using this feature on YouTube, I was able to essentially host my private video content for free.

To upload my videos, I first setup a YouTube account (which you technically should already have if you have a Gmail/Google+ account.) Then I hit Upload and dropped in my mp4 file (making sure to set my video as “Unlisted” like I mentioned above.)

Once all my videos are uploaded, I can use the embed feature to drop the embed links for each lesson into my course platform of choice (more on that below!)


For my second course, the Better Branding Course, I wanted the video player to look more custom and a bit more professional, so I opted to go with a service called Wistia. Wistia basically creates a white label media player for you which allows you to host your videos, customize your player overlay and upload custom thumbnail images to your videos. The result is something that appears a bit more modern and high-quality than the YouTube player.

Wistia vs YouTube

Wistia is a paid service, however, so if you’re planning to keep your e-course at a lower price point or if you’re trying to keep costs low, the free YouTube hosting route is certainly a viable option.


For hosting audio files, I really like SoundCloud. I love the way their embeddable player looks and functions, and the fact that you can customize things like the button color. Jason has a course about securing sponsorships for podcasts, and he uses SoundCloud to host audio interviews inside his course dashboard. Here’s what that looks like:

Speaking of course dashboards, once you have your content uploaded and hosted, you’re going to need a place for people to access your e-course!

Choosing A Course Platform


Full disclosure: my husband, Jason, co-founded a course platform called Teachery when he realized there weren’t any easy, turn-key but customizable course platforms out there. Teachery is what I use to host both of my e-courses.

Now, I know I’m biased, but I really do believe this platform is the best option for creative entrepreneurs that want a robust way to host a custom course without any WordPress or technical know-how. You can literally start building a course in minutes and it has some awesome built-in integrations with Stripe and Mailchimp.

The Teachery platform allows you to build your course and then connect it to a custom URL (like… “”, for example) with a customizable “dashboard” interface for your students that looks like this:

Teachery e-courses

And here’s what it looks like inside a lesson with my course videos from Wistia embedded:

Teachery lesson with Wisita

My favorite part about Teachery is that they handle all the complicated stuff like setting up user accounts (for your students to login), processing payments (securely!) and capturing email addresses of those students.

I especially love how easy it is to manage multiple courses at once and keep up with new students as they purchase.

Here’s what my Admin dashboard looks like on the back-end of Teachery:

Teachery dashboard admin

And then here’s what it looks like when I’m editing my course:

Teachery online course editor

For me, it takes the effort out of setting up my course so I can focus all my time and energy on the content and experience that my students get.

Here are just a few reasons why I feel Teachery is the best option for me:

  • The course design is customizable enough to match my brand colors, but not so complicated that I get lost down the rabbit hole of styling my course.
  • The Stripe integration makes it easy to set the price of my course and then my daily revenue automatically gets deposited in my Stripe account (and then my bank account.) I don’t even have to think about getting paid, which is awesome.
  • They have a promo code feature that allows me to set up special purchasing links with discounts or free access (great for gift certificates!)

If you’re a technology newbie but still want to create a video/audio course, I can’t recommend Teachery highly enough.


If you want a written-only course and want it delivered to people in a series of emails, I’d recommend using Mailchimp and setting up an automation sequence to drip content. While I’ve used Mailchimp’s automation before, I’ve never used it as a course delivery method. Here’s an awesome post by Paul Jarvis that details how to set up a self-paced email course using Mailchimp automation, better than I’m sure I could explain it. If you’re interested in this option, I’d give it a read: [How To Create A Self-Paced Email Course]

There are certainly A LOT more options than just Teachery or Mailchimp, and I know there are some WordPress plugins that offer the ability to build courses within your existing WordPress site. My advice is to do a little bit of research to find out which course delivery option works best with your technical skill level and the course experience you want to create.

OR… don’t do any research and just use Teachery because it’s awesome. It’s totally up to you.  🙂

If you DO decide to go with Teachery, they’ve created a FREE course walking through exactly how to set up your online course on the platform (yep – it’s a course about a course. SO META.) [ How To Build A Course In Teachery ]

Your lesson here: Choose the hosting method and course platform that fits your budget and technical skill level. If you don’t want to spend time and frustration setting up a password protected area of your website, use a third-party platform like Teachery.


Section eight:

Create Bonuses And Resources

Once I have my course built and ready for students, I also think about any additional resources or features that would be a nice draw for the course.

For example, the usefulness of the information in the Better Branding Course relies on the students’ willingness to apply the principles to their own business. That’s why as a part of the course, I created over 15 worksheets and templates for them to complete and use throughout the course.

For the more complicated worksheets, I created them using InDesign, and then for the simpler resources (like the Brand Elements Checklist), I used Keynote and exported to PDF.

I uploaded each worksheet PDF to Google Drive, and created automatic download links at the bottom of the lessons they pertain to. When a student clicks the link, the PDF downloads right to their computer. They can edit the PDFs digitally, or they can print out the resources and fill them out that way.

This is also the point where I start to think about things like on-boarding. On-boarding simply refers to the process of getting new users (students) integrated into your existing system (course.) I want to make it as easy as possible for students to go from the moment of purchase to diving head first into the course. That’s why I created a “Getting Started Guide” which is automatically emailed to new students upon purchase (this Welcome Email feature is another reason I love Teachery.)

The guide walks them through how the course works, the layout of content, and how to interact with other students using our community chat app, Slack. (For an in-depth post on how I set up the Better Branding Course Slack community and why I LOOOVE it, click here: [ How To Set Up A Slack Community ]

Your lesson here: As an option, this is a good time to think about how you can enhance the experience of your students beyond just the course content with bonus features like worksheets, on-boarding, and a course community.


Section nine:

How To Market And Promote Your Online Course

This is the home stretch, friends! Once you have your course built, it’s time to market it and launch that sucker! Here are a few things you’ll want to consider as you figure out how to make your course appeal to potential buyers.


Hopefully by this point you already have a great idea about who you’re building this course for. Even better, maybe you already have an actively engaged audience that’s excited to buy just as soon as you launch. The reason you want to get super specific and clear about your course audience is so that when it comes time to write your sales page or promote your course, you know exactly how to position your course so that it appeals to the people it will benefit.

Here are some questions to ask yourself as you nail down your course audience:

  • What type of person can benefit from this course?
  • hat pain point or problem does this course solve for them?
  • What might that person’s hesitations be as they consider purchasing the course? Where does that type of person hang out online?

Use the answers to these questions to position your course and to think of places you can promote it where your ideal audience hangs out.


Pricing can be a sticking point for a lot of people (I know it can be for me) because it’s hard to know what someone will pay for what you create, or the value that they’ll feel your course is worth. That’s why I think you have to ask yourself a couple key questions to get a general pricing range that is logical, and then you just have to go with your gut.

Think about your target audience. Now, ask yourself these questions to determine your pricing:

  • What’s their financial situation? How much money feels like too much money to them?
  • How valuable is this course content to them? Will the skill you’re teaching actually help them make money in the future?
  • What other courses/products will they be comparing your price to?

I will say, a lot of pricing/marketing information online will remind you that pricing your products high means you need to sell less to hit your overall revenue goals. And that’s certainly true. BUT I will say that there’s also a time and place for low-priced products, and if you create the right info-packed course at a low price point for the right audience, you can still make real money (my $20 lettering course being an example of that.)

Something else to keep in mind: you can always add content to your course and raise the price, but you probably don’t want to have to drop the price to get more sales (your early customers likely won’t take very kindly to this.) That’s why I always start with my lowest, best possible price and then if I add modules/content in the future (which I have done with both courses), then I feel I can ethically raise the price to reflect the new value of the course.


Before your course is ever launched, you want to start warming up the audience you do have and letting them know what you’re working on. You also will likely want to start collecting emails of people who are explicitly interested in buying your course once you launch. I usually set up a simple landing page on my website explaining what the course will be about along with an email capture to start building a pre-launch list.

Whenever I’m building a product, I also like to share the experience on social media so that people can actually get a behind the scenes look at the process of creating something (and this, of course, provides double duty by reminding people that the course will be coming out!)

I’d recommend starting to tease the launch of your course AT LEAST a month in advance of launch, if not two months before. This will give people time to understand why you’re creating the course and it will allow you to build up a healthy list to launch the course to.

Your lesson here: Figure out who your online course is most valuable to and then come up with a price for your course that feels appropriate to that audience and the content you’re offering. Then, start prepping your audience and gathering a list of people that would be interested in purchasing the course before it launches.


Section nine:

Launching Your Course

Hooray! You made it! Your course is a living, breathing thing and now it’s time to put it out into the world. Before you officially launch, though, you’re going to want a place to send everyone. This is where your sales/landing page comes in!

Designing your online course sales page

Sales page design can be another sticky point because there are just SO many ways and strategies to grab someone’s attention and tell them about the course. I recommend starting with something that VERY clearly speaks to your ideal audience and the pain point that your course will solve for them. Here’s the top of the Better Branding Course sales page which speaks clearly to my ideal audience: creative entrepreneurs who are NOT designers.

After that, you want to give people an idea of what they’ll get when they purchase your course and what the end result will be when they complete it. It can also help to include any credibility-building points like why you’re qualified to teach someone your course topic. Lastly, of course, you want to include multiple opportunities for someone to select the buy button and go straight to your order page.

As you design your sales page, ask yourself: Does this web page clearly explain:

  • What someone gets when they sign up for the course (type of content, what’s covered, etc.)
  • Why they should care and how this course will make their lives easier or better
  • How the course content is delivered
  • Why you’re a credible teacher
  • How much the course costs

Once your sales page is designed, it might be a good idea to ask someone that has little to no idea of what your course will be about to scroll through and see if they understand clearly what you’re trying to communicate.

BONUS TIP: Make sure you test the checkout process! The last thing you want on launch day is for people who want to buy your course to somehow have an error or issue when they’re trying ot pay you!

How do you want to sell your course?

You also will need to decide how long you want your course to be open for enrollment. Do you want the course to always be for sale (like my $20 lettering course) or do you want it to be for sale just once a year (like Marie Forleo’s B-school)?

OR… do you want it to be for sale for limited periods of time throughout the year, like the Better Branding Course which is open for 48 hours once a month?

There are benefits and drawbacks to each one of these options that you’ll want to consider. The downside to having a course always for sale is that someone who lands on your sales page doesn’t feel a sense of urgency to actually purchase. It’s easy for them to say, “Oh I’ll come back and buy that later.” The upside to that though is that if someone does land on your sales page, they can buy right when they have the impulse and you get paid consistently throughout the year. (I especially like this for the Better Lettering Course because I now can count on that product to bring me a fairly steady amount of money each month, something that was certainly a nice change of pace from the ever-erratic design client world!)

The benefit to limiting the duration of your launch window is that the sense of urgency could put some potential buyers over the edge to purchase for fear that the course won’t be open in the future. This is especially true if you do a big launch just once a year. If someone knows they’ll have to wait an entire year to get into the course, that’s a pretty compelling reason to buy during the small launch window. The drawback is that you might be losing some sales because if they find your course when enrollment is closed, it’s possible that they’ll lose interest by the time it’s open again. Also, if you launch just a few times a year, your revenue comes in all at once rather than in increments throughout the year. It’s a bit harder to predict your cash flow for your business if that’s the case.

Remember, you can always test one of these options, learn, and then change down the road. Right now, the monthly launches for the Better Branding Course are working well because I like focusing on a small number of students and helping them through the course, without worrying about new people starting all the time. However, I haven’t ruled out the option of opening the course up completely in the future. Only time will tell!

Once you know how long you want your course to be open, pick a launch date and mark it on your calendar!

5 ways to promote your course

Sales page, designed! Launch window, decided! Launch date, picked! Now it’s time to tell people and get some new students!

Now, this by no means is an exhaustive list of all the various ways you can promote your course, but these are the main ways I promote mine.

Email Marketing

Remember that pre-launch list? Now it’s time to put it to use! Those people have already raised their hands to say they’re interested in what you’re selling. A week before your launch, send them an email letting them know the launch date and how they can purchase. Then, the morning of launch, send an email letting them know it’s the big day! In that email, don’t just send them a link to your sales page (remember, they already said they want your product!). Be sure to include a direct link to your order page so they can purchase on the spot, as well as a link to learn more on your website.

If you have a main email list, you’ll also want to prep them and send them an email on launch day as well. Don’t overload your list with too many sales emails, but remember, this is likely your most engaged promotion vehicle because they’ve opted in. Don’t sell yourself short by sending only one email and then wondering why you didn’t get more sales.

Your Website

You likely already have some people visiting your website. Make sure it’s clear to them no matter what page they land on that there’s a product launch going on and direct them to your sales page. I do this through Squarespace’s Announcement Bar which sits at the top of my website during my launch period.

Video/Webinar Opt-Ins

I’ve never used the live webinar/free video series strategy to sell products, but I’ve seen it work for other entrepreneurs. The idea is to lead with free content (like instructional videos or a free webinar) that people have to give their email addresses to see, and then you can try to convert those people to sales of your course. Hilary Rushford uses this strategy for her Instagram course. She teaches a free class with something like 15% of the content from her paid course and then converts the webinar attendees to purchasers.

In all honesty, I don’t love the feeling of this method. It feels a bit bait-and-switch to me, BUT that doesn’t mean it can’t work and that certainly doesn’t mean it can’t be authentic. I’m still brainstorming on ways to test this promotion method in a way that feels good to me. Let me know in the comments if you’ve seen anyone that does it really well!

Content Marketing

My original Hand-lettering For Beginners blog post is still the #1 sales referrer for my lettering course. Don’t be afraid to edit blog posts that get a lot of traffic by adding buy buttons or at the least by adding links to your sale pages.

You can also think about where your ideal audience hangs out online and think about offering to write a guest post for those websites. Adding a quick link to your course in your author byline could get you some pre-qualified traffic. (This method probably works best for a course that has completely open enrollment because you never know when those posts will go live or when they might pick of steam.)

Social Media

Lastly, of course, you want to use your social media accounts to spread the word about your course. Do yourself a favor and create your promotion images or graphics ahead of time so you’re not scrambling for images when you want to post. And remember, social media is incredibly ephemeral these days, so even if you feel like you’re inundating people on all fronts, only a fraction of your audience will actually see all three of those Instagram posts you shared, and even LESS people will see those multiple tweets. If you share in a sincere and non-spammy way, you shouldn’t worry about oversharing.

There’s also the opportunity to pay for social media promotion like with Facebook ads or promoted pins on Pinterest. This is not something I’ve tested to-date as all my promotion is unpaid, but if you have a smaller email audience and really believe in your course, it might be worth testing!

Your lesson here: Leading up to your launch, come up with a promotion strategy that feels good to you. Remember, you’ve created a kick-ass e-course that will help people, so your job is to get it in front of them. Promote your course with pride, learn from what works and what doesn’t, and keep moving forward.


Section ten:

How E-Courses Have Changed My Life

PHEW! Holy cow, we made it!

I know I shared with you A TON of information in this post, and it might even seem a bit overwhelming right now. However, I invested the time to share just about everything I’ve learned with you because e-courses have quite literally changed my business and transformed my life.

Now I’m able to make money doing something that I absolutely love — teaching — and I get to do it in the way that I want. With the money I made on both my e-courses, I was able to pay off my credit card debt and I’ve taken my business from barely breaking even last year to being on pace to triple my revenue this year.

Here are the revenue stats for my first two courses, which I want to share with you NOT as a way to say, Look how much money I’ve made but as a way to say: With hard work and confidence in yourself, you too can make real money teaching what you already know:

I truly believe that everyone has something to teach.

We can all benefit from the knowledge that we collectively share, and there’s nothing wrong with getting paid to enrich the lives of other people with your natural talents.

If you’re a creative entrepreneur and you’re struggling to get some steady, recurring revenue, maybe it’s time to really consider building an e-course.

If I can do it, you can do it!

Start A Podcast Today Without Feeling Overwhelmed

May 24, 2015

Whether your main goal for starting a podcast is to make money, have conversations with interesting people, or share your opinions on a given topic, this guide will walk you through proven examples to take your podcast from an idea to something worth listening to. I’m also going to answer these common questions:

  • Is it too late to start a podcast?
  • Should I get a co-host for my podcast?
  • How can I make money with a podcast?
  • What gear do I need to sound professional?
  • How do I get my podcast featured in the New & Noteworthy section of iTunes?

Without further ado, let’s dive in!



Introduction: Is podcasting for you?

First And Foremost, Should You Start A Podcast?

Is there a topic or opinion that you’re dying to share? Have you spent years cultivating a skill and are looking for a place to share everything you’ve learned? Have you built a business or want to build a business and think a podcast could help you on that journey?

Podcasting is a fantastic way to get your unique message out in the world and (hopefully) in front of your target audience.

A podcast is not a place to complain about your issues with your cable provider and their lack of customer service (that’s Twitter). A podcast is not a place where you can put photos of your cute little niece Samantha (that’s Facebook). A podcast is not a place to teach people how to put IKEA furniture together, although, with some wit, that could be a highly ironic and funny podcast to listen to (you’d probably keep your IKEA videos on YouTube).

Jason and Caroline Zook

(Oh hey, this is me (Jason) and my wife Caroline just being 100% natural for this podcasting photo!)


Starting a podcast gives you a virtual megaphone

You are most likely very familiar with trying to grow an audience using Facebook, Twitter, Instagram, etc. However, unlike social media, the experience of choosing to subscribe to a podcast is more like an email newsletter subscription (or YouTube channel subscription). If your listeners choose to subscribe to your podcast, they get notifications and downloads specifically about your show.

When you have a message worth sharing, using a podcast to broadcast your message can be very powerful. People can hear your tone. They can feel your emotions. They may not be able to see the expressions on your face, but we’ve all listened to at least one podcast episode that inspired us.

A podcast can attract a new audience for you

One of the first podcasts I created was a co-hosted show with my friend Paul Jarvis. We would have fairly regular Skype calls where we riffed about entrepreneurship, creativity, business, and at times zombies and vampires. We decided to see if other people might find our conversations interesting and created a podcast called Invisible Office Hours where we explored the intersection of creativity and commerce (and zombies). Invisible Office Hours kicked off in 2014 with no audience and has grown to 3,000 downloads per week many years later. We continue to see new email subscribers and new customers who’ve found us and our businesses through our co-hosted podcast. (I’ll talk more about co-hosting versus going solo in the next section.)

Paul Jarvis and Jason Zook

(It helps attract even more listeners if you use a “blanket fort” when recording your podcast with your co-host!)

A podcast can deepen the relationships with an audience you already have

Jason Zook Action Army Podcast

For my own podcasts over the years, I’ve thought of them as a way to deepen relationships with an audience I already have. My previous website was called JasonDoesStuff and I had an email newsletter called The Action Army. After two years of writing consistent weekly emails, I felt the urge to turn some of my thoughts into a weekly podcast. Week after week I would publish a podcast episode similar to the email topic I’d shared, but with a bit more background and silly tangents (which are much easier to accomplish in an audio format). I loved receiving emails from Action Army subscribers who listened to a podcast episode and felt a whole other level of connection to me and my writing. Those emails always made me think: Podcast Mission Accomplished!

A podcast may only be a creative outlet for you

Caroline and Jason Zook circa 2014

Here’s what a lot of people writing articles just like this one won’t tell you: A podcast may not get a lot of organic listenership and may just be a fun side project for you. My wife and I ran a podcast from 2014 to 2015 called Sleeping With The Boss (silly, I know). The idea of the show was to share stories of how we lived together, but also how my wife worked for and with me on my various entrepreneurial endeavors. At the “peak” of our podcast downloads, we had 200 downloads per week. Let’s just say we couldn’t attract many mattress sponsorships with those numbers. But making money with Sleeping With The Boss was never our goal, we simply wanted to share our thoughts and have a collaborative project together.

Your podcast and mine will never be as popular as Serial.

Whatever reason you have for creating a podcast, just be honest with yourself about why it exists. Your podcast and mine will never be as popular as Serial, This American Life, Revisionist History, etc. That’s okay! We don’t need Serial-type numbers to measure the success of our podcasts. We need the numbers (or lack thereof) that actually matter for our specific podcast-creation reasons.

It’s hard to say whether podcasting has hit a “bubble” yet and is too over-crowded. I believe it hasn’t and that creating a podcast is a wide-open playing field that’s gaining a lot of great attention, momentum, and is becoming more accessible than ever.



Section #1: Co-host or go it alone?

When You Start A Podcast, Should You Have A Podcast Co-Host?

The majority of us aren’t working for NPR and won’t have a whole slew of people and audio resources at our disposal for our podcasts. Instead, we have to decide if the show we want to create can be done solo or needs a podcast co-host.

Solo podcast: If you can say everything you want on your own and feel confident in speaking situations (or just in general), then you probably do not need a podcast co-host.

Co-hosted podcast: If you find it awkward talking alone, in a closet, to only a microphone and your hanging clothes, then having a podcast co-host might be the right fit for you. I know, I know, you might not record your podcast in your closet, but if the idea of trying to talk by yourself on a podcast is overwhelming, you’ll probably want a co-host.

Pros and cons of starting a solo podcast

Pro: You call all the shots. Every single part of the podcasting process is controlled by you and no one can push back on any of your decisions (show name, episode content, format, etc). You’re the King of the podcasting castle!

Pro: Way less tech and editing involved. Having a solo podcast means you only need one microphone and editing your episodes should be a breeze.

Con: You do all the work. Sure, you can outsource podcast production (audio engineering) and other things, but the weight will most likely fall on your shoulders to record/edit/upload episodes, share and promote them, keep a recording schedule, come up with future episode topics, engage with your audience, etc. It can be done, I’m proof of that!

Con: It can feel a bit lonely in your closet. Even if you’re comfortable talking to your button-down shirts and blouses in your closet, it can get a little lonesome on the mic by yourself. But hey, maybe that’s what you’re looking for?

Pros and cons of a co-hosted podcast

Pro: Someone to riff off of. From my own experience, having a podcast co-host creates a ton of extra thoughts and ideas. Plus, I’ve learned that sometimes I have way less to say then I thought on a certain topic and a co-host can swoop in and save the conversational-day.

Pro: Someone to generate ideas with. My solo podcast had 100 episodes and at certain points, it was tough to come up with new topics to discuss. On the flip side, my co-hosted podcast has had 100+ episodes and it’s never felt difficult to come up with episode topics. Oh, and it’s not just episode topics, having a co-host is great to brainstorm promoting your podcast or ways to make money with your show (if you’re into that).

Con: You’ll argue at some point, sorry. It’s just bound to happen. It may not be a big blowout brawl, but it’s natural for people to disagree when working together. Tough conversations will have to be had at some point during a co-hosted podcast journey.

Con: Quick decisions are much harder to make. When you have a podcast co-host there’s a second decision-maker who has just as much say in what you do with your show.

Con: There’s a bit more tech involved. I’ve done an in-person co-hosted show and a co-hosted show via Skype. Both have their own technical challenges and add a lot more complexity to the mix. Especially if you’re going to edit your own podcast episodes, multiple audio tracks (or voices on a single microphone) can get tricky.

How to find a great podcast co-host

Who do you effortlessly converse with? Who shares similar values to you? Who could you spend hours working with? Those are the most important questions to answer when searching for a podcast co-host.

You know when you listen to a co-hosted podcast and you just feel the chemistry the two hosts have with each other? That’s exactly what you want to strive for.

Similar values are the best way to create great podcast chemistry

Your podcast co-host should share your same values for the best chance of long-term podcast success. You absolutely do not need to agree on everything in life, that would be a boring show, but the bigger picture items that you both believe should be in alignment. Example: Let’s say you’re a vegan, you probably don’t want to co-host a podcast with BBQ Pitmaster. That’s a recipe for disaster (heyo, food pun!).

TIP: I’d highly recommend recording and editing a few test episodes with your potential podcast co-host. How did the recording go? How was the chemistry between you? How was the division of labor to get an episode fully edited and produced? Reflect on this trial run before going all-in.



Section #2: Are interviews the only way?

Do You Have To Have An Interview Podcast To Succeed?

It can seem like the only way to have a successful podcast is to have an interview show. You know, like the Tim Ferriss podcast, Joe Rogan Experience, Magic Lessons, How I Built This, etc. But here’s the really important question you should ask yourself:

What does a successful podcast look like to ME?

It’s easy to answer, “Be #1 on iTunes!” or “Get a bajillion downloads and have all the mattress companies sponsor my show!”

I’ve started nearly 10 podcasts since 2014 and every podcast has had its own unique goal (neither of which were goals defined by things I couldn’t control, like being #1 on iTunes or a bajillion downloads).

Jason Zook previous podcasts

Are you podcasting to sell more of your products or services? This is a great reason to start a podcast, especially if you already have an existing audience and are simply trying to deepen a relationship with your people. You can measure the success of your podcast by putting a survey in the post-purchase email you send to anyone who buys things from you. Just ask them if they heard about your product or service on your podcast. If they say yes, then your podcast is successful at the thing you need it to be doing!

Are you podcasting to meet interesting and influential people? Then creating an interview-style podcast and landing guests that you admire will lead you down a clear path to podcast success. Most great interview podcasts didn’t start with the goal of climbing the iTunes charts, they started because the host wanted to have meaningful conversations with fascinating people.

Are you podcasting to scratch a creative itch? I’ve done this a few times and these podcasts have all been deemed successful if I could continuously publish new episodes and see some amount of listenership growth. When I scratched my creative itch or when I felt the urge to move onto something else, I knew this type of podcast had done its job.

Your podcast ranking on iTunes and podcast download numbers are just vanity metrics. You need to define what actual success means for your podcast.


The trials and tribulations of running a great interview podcast

I ran a podcasting workshop with friends who have a popular interview podcast. During that workshop, we talked about these being the common problems of running an interview-based show:

  • Interviewees having a terrible internet connection
  • Interviewees having really awful audio equipment (read: no audio equipment)
  • Interviewees not showing up on time for recording
  • Interviewees being great at what they do, but being awful conversationalists for a podcast
  • Editing show episodes takes at least double the work
  • Getting interviewees to help share their episode is like pulling teeth

While an interview show can be an amazing way to meet and have conversations with people, there’s no doubt it’s a ton of extra work. It’s important to understand what you’ll be getting yourself into and how you can curb some of these common problems by being as prepared as possible for them.

How to ensure your podcast interviews don’t suck

Let’s be honest, as much as we want to blame other people for not bringing their A-game, it’s on us as the creator of our podcasts to take the initiative and do everything possible to have great interviews.

Step #1: Create a “get ready to be on the podcast” checklist. This may seem trivial, but you may encounter podcast guests who don’t have a ton of podcasting experience. Recommend a few simple things to them:

  • Close windows or turn off AC to avoid background noise
  • At the minimum, use Apple headphones for the interview
  • Test their internet connection or make sure to be in a quiet location with good Internet
  • Close all unnecessary applications at the time of recording

Step #2: Give your podcast guests questions ahead of time. Most people don’t like to be surprised with questions, it can make for a very uncomfortable conversation. Send an email a few weeks ahead of time with a list of questions and make sure your guest feels good about the topics you’re thinking of discussing.

Step #3: Introduce your guest separate from the interview. One of my biggest pet peeves as a frequent podcast guest is when a podcast host asks me to introduce myself at the start of the show. The first 2-3 minutes of the episode are me giving myself an awkward introduction (or worse, the guest giving me an awkward introduction and I’m forced to be there listening to it). There’s a reason why most successful interview shows do an introduction separate from the interview and it’s because it avoids any immediate awkwardness when recording starts. If you have an interview podcast, record your guest introduction AFTER the interview as it will give you a lot more context to share with your listeners.

A couple of tips from a frequent podcast interviewee

Do your research and don’t be afraid to go off-script with your podcast guest.

I’ve been fortunate to do well over 100 podcast interviews over the years. In that time, I can count on one or two hands the interviews that were really great for me (and where I probably brought my best energy to the show!).

Tip #1 for a great interview: Do your research on your guest. As an interviewee, it’s easy to know when a podcast host just wrote down a list of topics and didn’t do much research on them. It forces the guest to feel like they have to overexplain things which leads to less-than-stellar experience. Podcast hosts like Tim Ferriss do a great amount of research on their guests and it shows in the quality of questions being asked.

Tip #2: Avoid phone interviews. This doesn’t seem to be the norm anymore, but I rarely spend time talking on my phone and it’s not going to give great audio quality. Use Skype, Zoom, Zencastr, or some other service (more on these services in Section #4: Podcasting Gear).

Tip #3: Be willing to go off-script. My least favorite interviews I’ve ever done are the ones where I feel like I’m answering a list of questions, none of which relate the answers I give. Here’s an example:

  • The host asks: Tell me about your crazy IWearYourShirt business
  • I answer for 2-3 minutes about my IWearYourShirt business
  • Then the host asks: Now tell me about your morning routine
  • I have to shift mental gears quickly and it can lead to an awkward answer

My absolute favorite interviews are the ones where a podcast host may have 5-6 topics to discuss ahead of time, but we may go really deep on one topic and never get to the other ones because our conversation ended up being so great and natural.

(As an aside, I actually like “lightning round” questions at the end of an interview. Those are where you can ask about unrelated topics because it feels like the answers can be quick and my brain is ready for it.)

Tip #4: Don’t badger your guest to share their episode. One of my least favorite podcast host moves is when I get an email asking me to share the episode with my email list or social media followers. I’m a big proponent of asking people to share work, but it’s all in HOW you make that pitch. The ask needs to be courteous and there needs to be zero pressure at all. Bonus points if you make well-designed shareable graphics, short audio/video clips, and have all the links easy to copy and paste.

Podcasting setup


How to get guests on your podcast

When you’re getting started, it will be an uphill battle to land notable guests for your podcast. Just understand this and be okay with it.

Many podcasters want to have high-profile guests on their podcast before they get their bearings and get comfortable hosting their show. Would you rather have Elon Musk on your podcast when you’re just getting started and don’t have all the kinks ironed out? Or would you rather wait until you’ve hit your groove, have the technical side of things down, and feel much more confident? (Feel free to replace Elon with your podcast guest of choice!)

Find podcast guests via your existing network

You’d be shocked who your friends know. You may not think your 180 friends on Facebook know anyone worth having on your podcast, but I bet you’d be surprised. In fact, I know you’d be surprised! Your existing connections, whether it’s friends on Facebook, contacts in your phone, email contacts, etc, are folks who trust you and would be willing to introduce you to their friends. Start with who you already know (and how they might know) and don’t be afraid to have a lesser-known guest on your show early on.

Look for people who are making the podcast rounds

It’s wayyyyy easier to book someone for your podcast if you can see them showing up on lots of other podcasts. That person is probably in some sort of promotion/marketing-mode and will be way more willing to say yes to your interview request (especially if you have a newer podcast). Reach out to the perspective guest via email or social media and do a little extra work to listen to their other interviews and offer up an angle for your show that will be different and may excite them.

Don’t shy away from in-person events

One of the best ways to land a podcast guest is to attend meetups or conferences. For me, when I used to do a lot of public speaking and would come off the stage and get asked face-to-face to be on someone’s podcast, I was almost always said yes. There’s a much stronger connection when you talk in-person and can create a bond right away. Don’t just seek out the speakers at events either, see if you can find interesting people attending the events who might be great interviewees.

Send a good cold email

I’ve been sent a small handful of good cold emails to be on someone’s podcast who I didn’t know. Here are the exact things that always stood out to me with these email requests:

  1. They did their research and it wasn’t a copy + pasted email they sent to tons of people
  2. They had a flexible schedule and offered a calendar booking link
  3. They had a list of topics that they wanted to discuss that were unique or things I was currently talking about on my website or social media
  4. They used funny GIFs or other humorous tactics (this works for people like me!)
  5. They shared other guests that had been on their show already that I might know

If you’re sending cold emails to prospective guests, don’t forget to send follow-up emails! I’ve written an entire article on the secret art of follow-up emails and would highly recommend reading that.

Show up in your guest’s social media feed, inbox, etc, without an immediate ask

Especially for higher profile guests, if you can put in the time and effort to support them and show up often (on Twitter, FB, YouTube, replying to emails they send, etc) without making an immediate ask, you’ll have way more luck down the road. This is a tactic reserved for podcast hosts that want to build a genuine relationship with someone and not just have them as a notch in their podcast guest belt.

And I’d be remiss if I didn’t mention some ways NOT to ask guests to be on your show

Do not: Badger people on social media. It’s one thing to show up in conversations, like tweets, comment on posts, etc. It’s another thing to constantly be pitching your show to someone.

Do not: Send copy + pasted emails. I’ve received so many emails from podcast hosts and I can tell it’s a boilerplate email with my name swapped out. People’s bullshit radar is high for generic outreach these days. Don’t just copy + paste.

Do not: Put a podcast guest on the spot. This is one of my least favorite tactics podcast hosts use. You’ll finish an interview, and then the host asks, “hey, do you have one awesome person you’d introduce me to have on the show?” It’s just not comfortable to be asked that question on the spot and feels weird. This is okay to do in a follow-up email after the show episode has aired, but don’t do it right after the interview.

Do not: Get angry if someone says “no” to be on your show: I’ve only had this happen a few times, but I’ve been in a “no-mode” while working on a big project. I’ll say “no” to being a guest on someone’s show and they’ll get angry. Respect other people’s time and ask them when a better time circle back around and ask might be.

Heads-up: In Section #4 I have recommendations of gear and software to use if you’re running an interview podcast. So, if you were looking for that, it’s coming up in a minute!



Section #3: Make money with your podcast

Podcasting Can Generate Revenue!

If you’ve listened to any podcast ever you’ve probably heard the mention of sponsors or advertisers. On some podcasts, you’ll hear the hosts call out their own products (merchandise, books, software, courses, etc). There are many ways a podcast can help you generate revenue, which may be how you’re measuring the success of your show.

Let me be clear that it’s 100% okay if you do not want to make money with your podcast. Your show may just be a creative exploration, which is wonderful and you don’t have to force your podcast to make money.

That being said, if you are trying to use your podcast to generate revenue, here a few ways to do that:

Make money with a podcast using sponsorships

I know I hear the company names MailChimp, Squarespace, Audible, Casper, and others all the time while listening to my favorite podcasts. As someone who has had quite a bit of experience with sponsorships over the years (2,000+ sponsors under my belt!), I can attest to the value of a great sponsorship relationship.

If you’re sharing a message that brings people value and you can make money promoting a company that aligns with your message, it can be incredibly beneficial to all both parties.

The best sponsorship and advertising relationships require alignment. The more you can talk openly and honestly about a product or service as a sponsor of your show, the better chance you have that your listeners will check it out (and the less they’ll feel like you’re “selling out”).

What do I mean by alignment? If you had a podcast about entrepreneurship, you probably wouldn’t want to talk about sponsors like Victoria’s Secret or Yankee Candle, those companies are not aligned with your show. Instead, you’d want to try to get sponsored by Squarespace or FreshBooks. These companies offer services that could benefit your entrepreneurial-interested listeners.

How much can you make with podcast sponsorships?

You should know ahead of time that there is no standard for podcast sponsorship amounts.

I have friends who make $100 per episode on their daily podcasts. That’s $36,500 in revenue per year! Not too shabby. I know other folks who make $1,000–$2,000 per sponsorship mention in their shows. I’ve personally made $500 per episode and as high as $3,000 per episode.

The amount of money you can make with podcast sponsorships is mostly based on how many downloads your show gets AND how aligned the sponsor is with your show’s content.

Many sponsors/advertisers will want to pay on a CPM-based pricing (Ex: Every 1,000 downloads = $100). I’ve never worked with a CPM-based advertiser because I’ve only ever wanted sponsors that were in direct alignment with my show’s content. That alignment allows me to charge a higher sponsorship price because the company paying me is getting a much more qualified listener. You can absolutely charge more for podcast sponsorships if you know your audience is in perfect alignment with a sponsor.

As a heads-up: I have an entire online course that teaches you how to get paying sponsors for your podcast. It’s exclusively available in our Wandering Aimfully membership.


Use a podcast to grow your customer base

My good friend Omar Zenhom had two failed podcasts before starting the Best of iTunes 2014 winner: The $100 MBA. Omar has been a teacher most of his life and realized his passion and teaching style would transfer well in a podcast. The $100 MBA podcast became the perfect promotional tool for a product Omar cleverly named The $100 MBA.

The podcast pre-roll, mid-roll, and post-roll can be used for your own products

Omar did this with his $100 MBA podcast, pitching his own product where he also had sponsors. He also went one step further when he created an entirely new podcast called WebinarNinja. His new WebinarNinja podcast was sponsor-free because he wanted to promote a software product that would help people host webinars and master the art of webinaring (yes, I just made that word up). In the episodes of his WebinarNinja podcast, Omar would use the pre-roll, mid-roll, and post-roll spots normally reserved for a sponsor to pitch his software product.

This strategy helped Omar build an email list of folks who listened to the podcast and were interested in learning more about his webinar software (when he started the podcast the software was still being built). I love this type of marketing tactic because it lets your customers feel like they’re getting in early before anyone else.

Justin Jackson made $12,049 selling digital books and courses on his podcast

Justin Jackson is a developer, writer, and product-creating-machine. Justin has created multiple podcasts, but his Build and Launch show was an intriguing listen because he was recording episodes as he created products he wanted to sell on the podcast. Justin would share late-night sound bytes of being tired or stressed out but pushed himself to finish his work so he could sell his creations to his listeners the next episode.

Justin generated $12,049 in revenue in just two months from his Build and Launch podcast audience! Each week Justin launched a new mini-product (books, plugins, and software) to the show’s ever-growing listener base. And the great part? As his podcast grew in popularity, his new listeners could go back into previous episodes, learn about the products, and purchase them!

Think about the small time slots in your own podcast as a place to not just promote sponsors, but promote your own products and services. Maybe your entire podcast is a marketing vehicle to sell whatever it is you create?


A podcast can help you find more clients

Grant Baldwin is a writer, speaker, and self-proclaimed lover of ice cream. In 2014 and 2015 while Grant wasn’t enjoying a bowl of Rocky Road, he hosted the How Did You Get Into That podcast. Grant would interview interesting people and ask questions about the start of their journeys. But, that wasn’t the only goal of Grant’s show.

Grant used his podcast as a megaphone to share when he had coaching slots available. He also constantly told his audience to get more information, downloads, etc, by joining his email list (which he could then market and promote other products to them as a subscriber).

The approach Grant used to monetize his podcast led to a spike in paid clients but also had the non-measurable benefits of networking and relationship building with the guests he had on his show.

Do you offer a specific skill that can help your listeners?

Grant is another podcast creator with multiple podcasts under his belt. When he stopped producing the How Did You Get Into that podcast, he transitioned his efforts to a new show called The Speaker Lab. The Speaker Lab shared Grant’s experience as a public speaker and each episode helped educate a listener who might be interested in getting paid to do public speaking of their own.

Grant used the podcast as a way to sell a course and community where aspiring public speakers could learn everything they wanted to know about public speaking. Pretty smart, huh?

Having a very focused podcast topic, especially related to a skill you’ve cultivated and can teach, is a great natural fit to sell a product or service via your show.

Sell something unique that’s only available to your podcast audience

I can personally attest to making money from a podcast in multiple ways (sponsorships, selling software, etc). One of those ways was something I hadn’t seen before: A bundle of products that was sold exclusively through a podcast season.

During the second season of my co-hosted podcast, The Invisible Office Hours, my partner Paul Jarvis and I decided to bundle up 20 of our products (online courses, books, guides, WP themes, photo packs, etc) and offer them only to our podcast listeners for a limited time of 12 weeks. We called our grouping of products “The Bundle of Awesome” and sold the bundle using a pricing strategy I created called bumpsale. The price of the bundle started at $1 for the first buyer and would bump $1 after each purchase (the second person paid $2, third person $3, etc).

Over the course of 12 weeks, our Bundle of Awesome generated over $40,000 in revenue!

Our audience was stoked to purchase a bundle that wouldn’t be offered again and could help them achieve their own goals. Plus, the bumpsale sales tactic helped keep the cost affordable and interesting!

Important note: Podcasting is a passive listen (it may not convert for you)

People listen to podcasts while doing other things.

I hope you’ve realized by now I’m trying to shoot you straight when it comes to podcasting. That’s why I wanted to add a section here that acknowledges that even if you promote your own products or try to get people to join your mailing list, your listeners may not convert. Why? People listen to podcasts while doing other things.

Edison Research found that 51% of podcast listens were happening outside of someone’s home. Over 40% of people listening outside of their home were in their car, at the gym, or somehow on the move.

Do you know what’s really hard to do? Take out your credit card and make a purchase while you’re on a treadmill or sitting in traffic on the highway.

It’s important to understand that your podcast listener is probably on the move somehow. They are very likely doing another activity which will prohibit them from purchasing whatever it is you’re trying to sell via your podcast. Don’t let this dissuade you from trying to sell on your podcast, just know that you may have to keep promoting episode after episode to catch your listener at the right purchasing moment ( you know, not covered in sweat).


What podcasting gear is best?


Section #4: Podcasting setup stuff

What Podcasting Gear Do You Really Need? (Microphones, Hosting, Etc)

I’m going to skip the absolute basics of podcasting because Pat Flynn already did a great job of this. If you want to know how to title your show, what an MP3/WAV file is, or any other Podcasting 101 things, I highly recommend Pat’s article.

With that being said, here are my firsthand recommendations when it comes to podcasting gear (disclosure: many of the links are affiliate links and I make a tiny commission if you purchase using these links):

The best podcasting microphones

I’m going to give you the best options for no budget (free), small budget ($100), decent budget ($300), and my current recording setup ($500+). No matter which microphone you decide to use it’s almost as important to have a recording environment that will help you produce great sounding audio.

Try to avoid recording in big open areas: No matter what microphone you use, a large open area will most likely have lots of echo which won’t sound great. If you do have to record in a large area, try to get as close to your microphone as possible.

Record in your closet (podcloset!): Don’t be afraid to snuggle up with your hanging clothing. You can get some really solid audio quality from your closet. (This may be harder if you host an interview show, in which case, a closet may not be an option for you.)

Hang a large blanket or canvas on the wall in front of you: You want the sound behind the microphone to get absorbed as much as possible. Hang up a blanket on your wall while you record or get a piece of canvas artwork that will soak up some echo.

No budget at all: Apple Earbuds (or similar)

If you cannot spend a dollar on your podcast and you have a set of earbuds or headphones with a built-in microphone, then start here! Anything will be better than recording with your computer’s built-in microphone.

Best free podcasting microphone: Apple earbuds


Under $100: RODE SmartLav+ or Blue Snowball iCE

For solo podcasting: I absolutely adore the RODE SmartLav+ (lavalier) microphone. For $80ish you can capture some really solid quality audio and have a lapel microphone that can be used for various other audio recording needs. NOTE: A lav mic is best used for solo podcasting because you’ll be using the headphone jack on your computer and won’t have a place to plug in headphones/earbuds. 


For co-hosted or interview shows: The Blue Snowball iCE is a verrrrry affordable option ($50ish). If you’re on a tight budget and want a great bang for your audio buck, this is definitely the option for you. Plug and play with USB, has its own small stand, and the Blue Snowball iCE is super portable.

Best microphone under $100: Blue Snowball iCE


Under $300: RODE NT-USB with swing arm

This was the audio recording setup I used for years! You can find the RODE NT-USB with swing arm for $240ish on Amazon. The swing arm can be mounted on a desk or on a shelf in your closet and the microphone can be easily moved out of the way when not in use. The RODE NT-USB is one of the best sounding USB microphones, making it incredibly easy to plug in, hit record, and be on your way. Plus, the microphone stand and built-in pop filter are nice additional pieces of equipment that come with the microphone.

Best microphone under $300: RODE NT-USB


My preferred recording setup ($500ish): RODE Broadcaster or Shure SM7B

This is where you step your sound game up and get that sexy voice of yours in the ears of your listeners. I’m giving you two microphone options, but both are in the $400 range. My current recording setup is as follows:

You could swap out the RODE Broadcaster and use the Shure SM7B microphone ($399) instead (saving you $20 and giving you a sleek looking black microphone).

Best podcasting setup for interviews: RODE Broadcaster


Podcast audio recording tech

I have to preface this section by admitting that I’m an Apple user and have been since 2004. That being said, almost everything Iim sharing in this recording section is available for Windows unless otherwise noted.

Solo podcast: Quicktime Player (free!)

I recorded over 100+ episodes of my solo podcast using just Quicktime Player. There are a handful of things you should pay attention to every time you record with Quicktime:

  1. Triple check you’re selecting the correct audio input in Quicktime
  2. Ensure you’re recording at the Maximum quality
  3. Speak loudly into the mic and make sure your audio levels aren’t clipping
  4. Close all other applications if you can, it’ll help avoid any complications
  5. Don’t forget to hit record!

Record podcast audio with Quicktime


Co-hosted or interview podcast (NOT in-person): Skype or Zoom + Quicktime Player (free!)

After much trial and error, I finally found a solid system to record a co-hosted podcast via Skype or Zoom. The premise is simple: Start your call on Skype or Zoom so that you can see yourself and your co-host (or your interviewee!). Then, both you and your co-host/interviewee will open Quicktime Player and record audio locally (as outlined in the Solo podcast instructions). Recording local audio is important and helpful because it has no bearing on your Internet connection and you get separate audio tracks which will vastly improve sound quality and editing.

I like using Skype or Zoom with video for my co-hosted podcast for a few reasons:

  • You can see each other which provides a stronger emotional connection (leading to better conversation)
  • You can see each other so you know not to talk over one other
  • Note: You don’t need to use the video, but it’s a great bonus if you want to share it with your audience

Using Skype or Zoom you can also record the audio of your call in case you want to have a backup. For Skype you’ll need an add-on called Call Recorder, but for Zoom there is built-in recording so you don’t have to download anything else.

The gist here: Use Skype or Zoom (which are free!) as a way to see your co-host/interviewee, but record audio separately using Quicktime (also free!) to get the best sound quality.

Bonus option: I’ve used Zencastr on multiple occasions as an interviewee of a podcast. I’ve heard great reviews, so it may be worth trying out.

Record podcast audio with Skype or Zoom


In-person co-hosted or interview podcast: Tascam DR-100MKII or MKIII ($399ish)

My wife and I record a podcast together in our house. We used to record standing next to each other in our closet on one microphone, but have since stepped up our audio recording game.

We use two RODE Broadcaster setups (my preferred recording setup above) and plug those two microphones into a Tascam DR-100MKII audio recorder (we use the slightly older model, the Tascam DR-100MKIII is newer and fancier). This setup takes audio recording to the proverbial next level, while also keeping the recording gear itself fairly minimal. One of my favorite things about this setup is that it doesn’t require having a laptop near us, so we can focus just on the topic at hand.

Once you record a podcast episode, you’ll pull the SD card out of the Tascam, plug it into your computer, and start the audio editing adventure with clear, crisp audio.

Note: Ain’t no shame if you want to pick up a used Tascam audio recorder! I did and saved about $150.

Record podcast audio with Tascam-DR100


Editing your podcast audio without losing your mind

There is an infinite number of ways you can edit your podcast audio. I am NOT a professional audio engineer, but I feel like you can produce a pretty damn good podcast on your own.

DIY: GarageBand

GarageBand was built for this sort of thing! You can easily setup your audio track(s), separate them by music or voice, make the edits you need, and export quickly and easily. Another humungous bonus to editing audio with GarageBand is that there is a never-ending supply of free tutorial videos on YouTube to help guide you through the process!

If you’re a Windows user, Audacity is a great (free!) option with similar features and helpful tutorials on YouTube.

Paid Service:

I used the folks at for over a year. The process was incredibly efficient and saved me a ton of time. I’d simply record my audio, send it to the PodcastMotor folks, give them simple instructions, and a few days later I had a fully produced podcast episode for just a few bucks. How many bucks? That depends on the length of your episodes and complexity of the production (the range could be $30 per episode up to $300 per episode).

There are many podcast production companies out there these days, but I have first-hand experience with PodcastMotor which is why I’m recommending them. Also, I don’t get any commission if you use them, so there’s no incentive for me here.

Paid Service: Find a freelancer!

Want to support a fellow creative doing work they love? There are tons of freelance audio engineers floating around out there. You can find folks on UpWork and Fiverr, but I don’t have experience with anyone specific on those sites so I can’t make a solid recommendation.

Let’s talk podcast hosting and publishing

This is another area of podcasting where you have almost too many options at your disposal. But, I’m going to give you the ONE service you should use based on my personal experience over the years.

Simplecast ($12/month)

I love Simplecast for a few simple reasons (get it?!):

  1. The initial podcasting setup is a breeze!
  2. The embeddable Simplecast podcast player is beautiful and works really well
  3. Simplecast can help you migrate an existing show from another podcast host
  4. They offer user-friendly podcast analytics (which most hosts don’t)
  5. Their customer support is fantastic

I used a handful of other podcast hosts over the years and cannot say enough good things about Simplecast. There’s a reason why well-known shows like Off Camera and Armchair Expert trust Simplecast, and if it’s good enough for the big dogs, it’s good enough for the rest of us.

I feel like it’s worth noting that I do not get compensated in any way by promoting Simplecast. That’s just how great of a product they have, I want to share it with you!



Section #5: New & Noteworthy

Getting in the New & Noteworthy Section of iTunes

I’m not going to lie to you and say these next few paragraphs are guaranteed to work. What I am going to tell you is that they worked well for me and anyone I’ve helped start and publish a new podcast in iTunes.

Why should you care about the New & Noteworthy section?

It’s a guaranteed window of additional promotion to the front page of whatever category your podcast fits into. This is hugely beneficial in growing your listenership early on and creating some awesome credibility for you and your podcast (especially if you’re trying to court sponsors or get your audience to tune in to your new podcast).

How to get a podcast in New and Noteworthy on iTunes


Step 1: Build an email list or spreadsheet of contacts first

Before your podcast gets published and your episodes are live on iTunes (aka Apple Podcasts), you should be building a list of people you can reach out to on the first day your podcast goes live. If you already have an active email list you can tap, awesome. If you don’t, start building one. You can (and should) use your existing contacts and let them know you’re about to launch a new podcast and would their help with it when it launches.

Step 2: Record at least three podcast episodes before launch

This isn’t mandatory at all, but it certainly seems to help. Why? iTunes seems to value the time spent listening to your podcast episodes. What’s going to increase that time on your launch day? Having more than one episode to listen to!

Step 3: Know that iTunes can take 2–4 days to show your podcast

Once you submit your podcast RSS link to iTunes (via iTunes Podcast Connect), it can take 2–4 days to have your podcast show up. Upload those episodes early and don’t worry if people find your show before your actual launch date. Be prepared for this! Especially as it relates to this next step…

Step 4: Get people ready and pick a launch date

Whether it’s on social media, your email list, or the secret society for pancake lovers that you belong to, let people know when your podcast is going live. You’ll want to pick a launch date and ensure it’s after the 2–4 day time window from iTunes. If you set a date and get people ready for it, your chances of getting them to help you with reviews (which I’ll get to in a second) and listens drastically increases. Here’s an example email/promotion schedule I’ve used to get people ready for a new podcast launch:

  • 1 month before launch (tease people with the show and when it’s coming)
  • 1 week before launch (share the name of the show, a few episodes, make an audio clip or two – remind them of the launch date)
  • Launch day (don’t be afraid to share a bit more on social media or on email, you only launch your podcast once!)

*Bonus: Having a podcast launch party is also a great idea! You can do it virtually through live video or in-person on your launch day.

Step 5: Launch day!

Your podcast (with multiple episodes) is up on iTunes, it’s time to tell the world … but what do you tell them? iTunes values two things above all else: Subscriptions and Reviews.

Show people exactly how to leave a review

Lots of people have never left a review on a podcast before, give them detailed instructions on how easy it can be done. You may even want to go so far as to create a “How to leave a podcast review” page on your website that includes helpful screenshots. Check out Louis Grenier’s example page and create something similar.

Remember that people are busy and they may need a few reminders to leave a review on your show. Those early reviews are important, so don’t be afraid to ask a few times on your launch day.

Don’t just tell people to subscribe, tell them WHY they should subscribe

Does your podcast help people build lasting habits? Does your show debunk societal myths? Do you and your podcast host obsess over Harry Potter and break down every scene in your episodes? Tell your audience that subscribing to your podcast will help them get new episodes about habits, debunking myths, Harry Potter, etc. Just saying “go subscribe” doesn’t convince anyone or give them a compelling reason to take action.

Personalized emails go a long way

Don’t be afraid to hunker down and send 50–100 personalized emails on your podcast launch day (pro-tip: have these written ahead of time). These personalized emails can really move the needle in getting early reviews and subscriptions for your new podcast.

Step 6: Create and share future episodes consistently

Get 2-4 weeks ahead of your podcast publishing schedule.

All platforms enjoy consistent content creators. iTunes is no different. Whether you’re doing a daily, two days per week, or weekly show, make sure to stay consistent early on. Hopefully, you’ve planned ahead and are recording episodes multiple weeks in advance. This is a great habit to get into and keeps your consistent podcast publishing schedule intact.

After those six steps, it’s really out of your hands if your podcast will show up in the New & Noteworthy section in iTunes. Yes, you’ll want to share your new show on social media, but those platforms aren’t great at getting people to take action and do something (especially two things: subscribe and leave a review).

Don’t be afraid to continue to talk about your new podcast! You should definitely send another email to your audience the day after launch to remind them to keep helping you out. If you have reviews to share, those tend to encourage people who are weary about reviewing something.



Some Final Thoughts About Podcasting

If you walk away from this podcasting guide with nothing else at all, walk away with this:

Create something worth listening to. Don’t just start a podcast to start one.

Do some research into the topic you want to discuss and see who’s already discussing it. It’s not a problem if there are people already in the space—competition simply means people are already interested in that topic. What’s your unique way of talking about a certain topic? Pour as much of your own personality into your show as you can.

Quality over quantity!

Yes it’s cliché, but it rings extremely true with podcasting. Your show needs to sound good, and making that happen isn’t hard or expensive. Invest in a good microphone and either learn how to do simple audio engineering or pay a professional to do it. Invest in your show and it will pay dividends.

Good podcasts don’t stop at pushing their audio content out into the world. Good podcasts keep the experience going somewhere else and build a loyal base of fans/friends/followers.

Your podcast should be a conduit to something else. Whether that’s an email list, your website, your business, etc. Who knows how long iTunes is going to be the king of the podcasting space. If you rely heavily on iTunes and they make an algorithm change (or just get rid of podcasting), you don’t be want to be up the up the creek without a paddle.