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What To Do When You Experience Burnout

February 10, 2019

Don’t Need Video? Listen Now

Episode Summary

We’ve had the DISpleasure of dealing with creative burnout on more occasions than we’d like to admit. It simply seems like experiencing burnout is a right of passage when you work for yourself.

But… We have a few tips on how to avoid burning out. How to (hopefully) not hit your own wall and feel like your health and life are suffering because of your work.

Burnout is something soooo many of us deal with but we can feel ashamed to admit it. Well, we’re here to pull back the curtain on burnout shame and to talk openly and honestly about it. We hope this episode helps you learn from our mistakes and avoid burning out with whatever you’re spending time on.

QUESTION FOR YOU: Have you experienced burnout? How have you dealt with it? (Feel free to comment with your answer on YouTube).


Episode “Sponsor”

Wandering Aimfully Memberships

Our show will remain sponsor/ad-free and you can support us by becoming a Wandering Aimfully Member. Our monthly membership program offers our brand new program Build Without Burnout as well as “The Vault” (all the courses, workshops, and software you’ll need to run your online business) and you get access to an amazing community of creative small business owners to help inspire, motivate and support you. Learn more about our membership here.

Time Management Tips for Client-Based Business Owners

January 17, 2019

Do you feel like you’re ALWAYS working? Is time management your nemesis?

If your client projects often seem to take longer than you think and time feels like it just slips away every day, we have some tried-and-true time management tips for you.

Do you wish you could carve out time to work on projects related to growing your business like creating content and perhaps a digital product to offset your client income? But do you feel like every second goes to client work?

You need a better system to feel in control of your schedule and we’ve got you covered!

(Ps. You can watch this post in video form here:)

Time Blocking 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 article and this worksheet helpful, sign up for our newsletter where we share worksheets like this every Monday.


Time Management Tip #1:

Your first time management tip is to set micro-deadlines

What the heck are micro-deadlines and how do they differ from normal deadlines?

Chances are if you work with clients you’re no stranger to deadlines. Your clients know when to expect the final deliverables to complete the project. But the problem with setting ONE fixed deadline at the end of a project is a little thing called Parkinson’s law.

Parkinson’s Law says that: “work will expand to fill the time available for its completion.”

This means if you only set one deadline at the end of four weeks, for example, you’ll fill that entire four weeks with the work for that project, probably not very efficiently.

It’s like defining one big bucket for the project and your time will expand to fill the bucket. Instead, try setting a final deadline AS WELL AS micro-deadlines throughout various stages of the process.

By defining these smaller “buckets” based on the specific tasks in each phase of your project, you can better keep your work contained to those individual buckets, making you more efficient overall and only spending the time necessary to complete each task.


Time Management Tip #2:

It’s time you utilized time-blocking on your calendar

This was by far the biggest game-changer for both of us, and it’s incredibly simple.

What exactly is time-blocking?

Think of every hour on your calendar as one “block.”

Realistically define how many “blocks” you have available for deep client work each week (by deep client work we just mean the actually doing of the creative thing, not answering emails or hanging on social media).

Then, schedule your clients by blocking off these hours on your calendar each week.

How to use time blocking to track your time better

Not only will time-blocking help you with your client flow, but you’ll have a clear sense of what you should be working on each hour and that will help you avoid that feeling of time slipping through the cracks.

Time-blocking is also a great way to block off the things you want to make more time for aside from work like family, new creative projects, fitness or say building a new digital product.


Time Management Tip #3:

Make sure you estimate your client projects accurately

Sounds like a no-brainer, right?

With every client proposal you send out, make sure you’re estimating exactly how many hours you’ll spend on it and doing what tasks.

Then… and this is the key… as you complete the actual project, make sure you’re using a time-tracking tool like Toggl to track your time and match each part of the process up to your estimate.

Remember that you’re being paid based on this time estimate, and every hour you go over, the value of your time plummets.

The closer you stick to your estimate, the more efficient your projects will be.


If you’re looking for a step-by-step program to help you launch digital products, you might want to check out our program, Build Without Burnout Academy.

This is a six-month guided program teaching client-based business owners how to transition to digital products, without losing your sanity in the process. Get weekly course videos, monthly calls for accountability and support, plus get access to the rest of our courses and Slack community inside our Wandering Aimfully Membership.


How To Manage Your Time Better

Let’s recap the time management tips for client-based business owners

#1 Set micro-deadlines for every stage of a client project

One big deadline for a client project is good in theory but not great in practice. Sure, you can still use a project completion deadline, but you should also create micro-deadlines along the way (we recommend weekly milestones for micro-deadlines).

#2 Utilize time-blocking on your calendar

Look at your calendar as a group of available blocks. Instead of just saying you’re going to get XYZ part of a client project accomplished in a day, break bigger tasks into 30-60 minute blocks and put them directly on your calendar.

#3 Correctly estimate the time allocated for every project

Incorrectly estimating the time it takes to complete a client project is the fastest way to run a business that isn’t profitable. Your time IS money and you need to estimate it and track it properly. Use a time-tracking product like Toggl and you’ll start to figure out exactly how long your work ACTUALLY takes and you’ll get better at estimating client projects.

Time management may seem boring and rigid, but coming up with a system that works and sticking to it is WAY better than being exhausted all the time.

Working nights and weekends, and not getting paid what you’re worth is not a healthy way to live or run your business. When you have a client-based business, your TIME is your money-making asset so it’s important to use it wisely.

Just implementing a few of these changes could drastically improve your well-being AND your bottom line.

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!

How To Pick The Right Digital Product Idea

January 9, 2019

If you want to diversify your client income but don’t know which digital product idea to choose from, we’ve got your back!

You want to create a digital product so all your business revenue isn’t tied to trading hours for money, but you have multiple product ideas you’ve been thinking about.

If you have no idea how to pick the best digital product idea to pursue, we have three simple and tips to help you narrow it down. Ready to choose ONE idea to focus on so you can start building and making additional money? Let’s do it!

(Ps. You can watch this post in video form here:)

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 article and this worksheet helpful, sign up for our newsletter where we share worksheets like this every Monday.


Picking A Digital Product Idea Tip #1:

Choose the product with the most natural fit for your existing audience

One big mistake we often see business owners make is that they build a small audience related to their service, but then want to create a product on a completely different topic out of left field.

Is this you right now? Maybe it’s motivated by boredom because you spend all your time on your main service offering, or maybe it’s just because you’re multi-passionate. Either way, you’re likely making it harder on yourself by trying to reinvent the wheel.

Digital products sell best when you have a captive audience who needs what you’ve created.

Even if you have an email list of 500 people or a small social media following, that group of people is already paying attention to what you’re doing and that’s a valuable asset.

If you’re short on time and you want your first product to offset some of your client income, help yourself out by choosing the idea that’s the most natural fit with the small audience you already have.

What does your existing audience need? What are they interested in? Start where you are, get some momentum and THEN you can always create that other “left field” product later on down the road.


Picking A Digital Product Idea Tip #2:

Try validating one or two of your product ideas by launching pre-orders

Want to know which of your product ideas is most viable? Quit guessing and instead put your ideas to the real test by asking people to pre-pay for them!

Pre-selling is our favorite way to ensure we don’t waste time building something that nobody wants.

Refine one or two of your ideas enough to put up a simple sales page, and promote the page or pages to your audience. Of course, be sure to let them know it’s a pre-sale, and they may have to wait a while to receive the final product.

Set a benchmark for yourself for how many presale orders you need in order to justify investing the time building the product.

This has two benefits. #1: It will show you if there’s enough interest in your idea to make it financially viable BEFORE you carve out time to build it. And #2: It will make you set a deadline to deliver your product and an audience to be accountable to, which might just motivate you to finally create what you’ve been meaning to create.


Picking A Digital Product Idea Tip #3:

Go with your gut on what you’re most excited about!

Okay, the last two tips are pretty strategic and are based on the assumption that your digital product HAS to make you money right away.

But the truth is, building a product isn’t easy, and it certainly isn’t easy when you’re already working on servicing clients with your business.

Enthusiasm, excitement, and passion go a long way in fueling you through the difficulties of bringing your idea to life.

You can over-analyze all you want or strategize which idea will have the greatest impact on your business, but sometimes you just have to go with your gut and make that thing that keeps nagging at your brain.

Maybe it will take your business to the next level, maybe it won’t, but we guarantee you you’ll end up learning a lot and you’ll experience the satisfaction of finally getting that exciting idea out of your brain and into the world.


If you’re looking for a step-by-step program to help you launch digital products, you might want to check out our program, Build Without Burnout Academy.

This is a six-month guided program teaching client-based business owners how to transition to digital products, without losing your sanity in the process. Get weekly course videos, monthly calls for accountability and support, plus get access to the rest of our courses and Slack community inside our Wandering Aimfully Membership.


How To Pick The Right Product Idea

Let’s recap how to pick the right digital product idea

1. Think about which product best serves the needs of your existing audience

It’s easy to get distracted with all the ideas of unrelated products to what you currently talk to your audience about, but staying focused on what your audience already expects from you will point you in the right direction. Save your “left field” product idea for later on once you get a digital product created and generating revenue.

2. Launch a pre-order to see which idea people are actually willing to pay for

Collecting email addresses and positive sentiments on social media can feel validating for your product idea but the BEST validation tactic is to get people to put their money where their mouths are (you know, without actually doing that because of germs). Don’t be afraid to launch a pre-order before your digital product exists. If you can get your audience to buy into the idea of the product you’ll know you’re onto something!

3. Consider which idea you’re most excited to work on and can’t stop thinking about

When all else fails, listen to your gut. Your intuition exists for a reason and often times guides you in the right direction. If you simply can’t make a decision on which product idea to choose, lay them out in front of you and let your gut decide.

If you want to build a product…

The most important thing is that you stop over-thinking things and start taking action. Use one of these three tips to finally narrow in on a product idea and go all in on making that a reality.

Business is about experimentation and you won’t truly know which idea is right for you until you make a decision, build the thing and learn from the experience.

10 Entrepreneurial Lessons From 10 Years of Experience

September 24, 2018

On September 24, 2008 an idea hit me that completely changed my trajectory in life and business. I was going to ask the world to pay me (a nobody living in Florida at the time) to wear a sponsored t-shirt and create content on social media. At the time there were barely any people on Twitter, Facebook was still a closed platform (you had to have a college email address), and being a “vlogger” wasn’t a thing on YouTube. But it wasn’t just my IWearYourShirt idea that kicked off on that day, it was the decision to work for myself and run my own business.

Since that day day in September of 2008, I’ve learned an immense number of valuable lessons. I’ve written two books (#1 and #2) that go into greater detail of my entire entrepreneurial adventures, but I thought it would be fun to give you an abridged version with 10 entrepreneurial lessons that may help you if you’re currently working for yourself or thinking about working for yourself.


Lesson #1: It takes work and effort (there are no shortcuts to success)

Many times during these past 10 years I’ve tried to skip the hard work I knew it would take to launch a project, build a website, manage customers, etc. I wanted to believe the shortcuts, cheatsheets, and blueprints that other people were offering could help me skip the hard work and patience it actually requires to succeed when working for yourself. I was wrong. Every time. If you aren’t willing to do the work, in whatever shape or form “the work” takes, you will not succeed. But if you are willing to put in the hours, the effort, and push through tough/ambiguous times, you will be successful (however you define that success).

Additional reading: What It Takes To Be An Entrepreneur


Lesson #2: I wish I would’ve defined what my “enough” was earlier on

It’s unbelievably easy to let our brains get caught up in the trappings of more. To crave more money, more attention, more likes, more everything. It would’ve saved me a lot of mental battles and money had I been willing to sit down and clearly define what “enough” meant to me. These days Caroline and I always define what our enough is for anything that can be measured (the amount of money we can make, the amount of subscribers we can get, etc). By drawing a clear, realistic, line in the sand of where we’ll be happy, we’re able to enjoy every part of the process and never get stuck dreaming for bigger and better.

Additional reading: Why You Should Focus on Enough Instead of More


Lesson #3: Test all of the assumptions all of the time

Have you ever had these thoughts: “I don’t know why someone would buy from me” or “too many other people are already doing XYZ thing I want to do.” Those and many other assumptions will stop you dead in your tracks before you even have a chance to see if they’re correct or not. I feel very fortunate that I’m wired to question every thing in life, at every turn. Now, my family and wife may have some thoughts about how that way of thinking can be a bit of a pain in the ass, but it has served me well in business to never get stuck worrying or letting self-doubt stop me before I got going.

Any assumption you have, especially about business, should be tested with actual data and proven right or wrong. Also, if you’re sharing your ideas with friends and family, they will absolutely share their assumptions with you. Don’t let THEIR fears stop YOU.

Additional reading: Challenge All of the Assumptions, Especially Your Self-Limiting Ones


Lesson #4: It’s helpful to learn the basics of code, SEO, marketing, sales, and accounting

I’m a big advocate of outsourcing your weaknesses and not spending time doing things you aren’t good at or don’t want to do. However, learning the basics of HTML/CSS, SEO, marketing, sales, and accounting, can help you speak the language of the people you are outsourcing to. There are multiple times in the past decade when I blindly accepted someone’s advice thinking I could trust them on their word, only to find they did crappy work that had to be redone. Had I known the basics of what they were working on, I could have asked the right questions along the way and avoided the headaches.

You don’t need to become an expert in anything you aren’t going to use on a daily basis, but you should arm yourself with a basic knowledge so you’re not completely in the dark and having to rely on trusting strangers with your business.

Additional reading: Outsource Your Weaknesses To Run A Happier and Healthier Business


Lesson #5: Don’t do it alone

The first couple years of my entrepreneurial journey I would’ve benefited from having a mentor or a coach. Someone with experience who could’ve guided me through situations that most business owners encounter. Instead, I was too proud to ask for help (the next lesson will address this). I believed I could do everything myself and that I didn’t need any help. Wrong. When you’re working for yourself, having someone you can confide in, brainstorm with, give you time-worn advice, and set you straight when you’re veering off your path is immensely valuable. Having Caroline come into my life hasn’t just been amazing for me personally, but she’s someone I can talk to at a moment’s notice who’s smart, creative, experienced, and extremely supportive. I 100% realize you may not have a Caroline in your life (sorry!) but you should absolutely try to find a person or a community that can support you on your journey.

Additional reading: Bad Friends Are Toxic, Here’s Why You Should Reevaluate Friendships


Lesson #6: Pride can be helpful to push through tough times, but it can also keep you trapped

Pride is probably one of the biggest double-edged swords for me in the past 10 years. While it’s been part of my success to put my crazy ideas out into the world, it’s also been my downfall on many occasions. My pride got me into $100,000+ in business debt. My pride burned a bunch of relationships over the years. My pride kept a project going longer than it should have. My pride has kept me trapped a few more times than I’d like to admit, and I don’t wish that for you. The best advice I can give when it comes to dealing with your pride is in Lesson #2: define your enough. By establishing clear boundaries of enough, you can keep your pride at bay.

Additional reading: It’s Okay If You’re Feeling Lost


Lesson #7: Empathy goes a long way (in sales, in customer service, in being a relatable human)

There are lots of little moments throughout the past 10 years where I’ve put money aside and opted for being a good human over being a ruthless business owner. Whether it was as simple as giving someone a refund or spending thousands of hours replying to emails from people asking for advice, empathy can go a long way. You can’t see empathy on a Profit & Loss statement, but being an entrepreneur isn’t just about profits for me. It’s about being helpful and about passing on all the lessons I’ve learned in every aspect I can. It’s about treating people with respect and trying to give more than you get. The long-term side effect of operating with empathy is attracting a group of customers who are loyal and who feel appreciated by you.


Lesson #8: Putting up a website without promoting it is like building a hotel in the desert

Every idea I’ve had since 2008 has had a website. I’ve spent so much time, energy, money, and effort to make my websites welcoming, fun, and informative. But all that effort would’ve been worthless if I didn’t spend the time to promote my website and use my creativity to help people find it. Much like building the most beautiful hotel in the middle of the desert, if you don’t tell people it exists and build roads to it, no one will ever find it. I believe there is a clear path to running your own online business and helping people find whatever you’re building:

  1. Create consistent and authentic (to you!) content (articles, videos, etc.)
  2. Build an email list that shares your content on a recurring basis
  3. Come up with ways to get your website in front of people so they can find your content
  4. Deliver value as often as possible to your email list (that doesn’t mean discount codes)
  5. Focus on being helpful or entertaining in everything you do

Exciting and shiny social media channels will come and go throughout your time building your own business. Being helpful and actually showing up for your customers never goes out of style. There’s no algorithm that can stop you if you’re willing to do consistent creative work.

Additional reading: The Ethical Guide To Building An Email List Without Sleazy Tactics


Lesson #9: It’s a 5-10 year process to get true clarity and stability in your business. Be okay with this.

I bought in early on entrepreneurship. The day I stood in my closet 10 years ago and committed to starting IWearYourShirt was the day I also said, “I’d rather work for myself for the next 30-40 years than show up at a job that takes 1/3 of my life from me.” So many aspiring business owners are dreaming of a magical payday that will never come. If you simply accept the fact that working for yourself is a gift and something you can enjoy, you’ll be okay with building your next thing for 5-10 years and planning to continue to do it well after that.

I’m at year 10, and yet I feel like we just hit the reset button on the video game of our entrepreneurial lives. We have a brand new business, website, podcast, content strategy, customer base, etc, and while it can seem daunting, I also understand that I have 10 years of experience and lessons learned I get to apply to this recent reset. It’s not going to be easy, but I know we’ll avoid the missteps and traps I’ve fallen into in the past.

Find a way to enjoy the process and your impatient desire to have it all fall into place overnight will start to disappear.


Lesson #10: Is where you are today where you dreamt you’d be a few years ago?

In other words, be intentional about appreciating how far you’ve come. This is probably one of the most helpful thoughts you can have when working for yourself (or just being grateful for where you are in life). Is where you are at this very moment a place you could only dream of a few years ago? It’s easy to get stuck and think things aren’t perfect in your life/business, but if you look back to where you were a few years ago and realize where you are today is some semblance of a dream come true (no matter how small the dream is), take that moment to be grateful. If you aren’t where you wanted to be, what are YOU going to do to make your dream come true in the next few years?


I’m so incredibly grateful that 10 years ago I took a risk on myself and a crazy idea I couldn’t let go of.

It led me down a path that brought me to this moment and this life, and that’s pretty darn cool. Whether you’re at the beginning of your entrepreneurial journey, or like me you’ve been at it for a decade… here’s to the next 10 years!

Back To Business Basics: Set The Foundation For Your Future

September 3, 2018

Who’s ready to get Back to Business Basics!!

Since starting the Wandering Aimfully community (even back in the days when it was still called BuyMyFuture/BuyOurFuture), we’ve had so many people reach out asking for advice about how to reach their business and life goals. While we’ve offered individualized advice to many over the years, we have noticed some overall themes that pop up time and time again.

Questions like:

  • How do I know what to focus on to grow my business?…
  • I know what I need to do but I struggle to find the time to improve my business…
  • I make a bit of income here and there but I never seem to reach that point of financial security and freedom…

Our remedies for these common challenges most often boil down to the most foundational parts of running a business. Namely…

  • Knowing and tracking your income by revenue stream (we know some of you out there right now are just guessing!)
  • Tracking your living and business expenses (and streamlining them regularly!)
  • Understanding where you’re spending your time, both in a macro sense (what aspects of your business in general do you devote the most time to) and in the micro sense (where do you spend each minute of your day?)
  • Scheduling your week so you prioritize what you keep saying you want to accomplish
  • Having a clear system of evaluating your revenue streams so you know what the most effective use of your time and energy is based on your goals
  • Coming up with a clear plan and timeline for executing your growth strategies

So many of these things are things you already know—they’re things you feel should be in place for your life and business already—yet sometimes the simplest things are the hardest to pay attention to.

Sometimes the simplest things are the hardest to pay attention to.

Let’s face it: Finances are scary, productivity isn’t sexy, and choosing one focus is uncomfortable, especially for multi-passionate and creative people like those in the Wandering Aimfully community.

But believe us, getting clear on these things is the only way to make sure your business is built on a solid, sustainable foundation going forward.

That’s why we’ve created a four-phase roadmap to help you strengthen the foundation of your business.

We want you to use this as motivation to finally get these foundational pieces in the right place to gain more clarity and focus.

So, it’s back to basics we go!


Here’s an outline of what we’ll work through together:

  • Phase 1: Know Your Numbers (Tracking your revenue and expenses)
  • Phase 2: Where Does Your Time Go? (Tracking your time, productivity and scheduling)
  • Phase 3: Evaluating Revenue Streams (Understanding input vs. output for each project or revenue stream)
  • Phase 4: Choosing Your Focus (Deciding which aspect of your business to make your primary focus and writing an action plan for the next three months)

If you’re an existing WAIM Member reading this, be sure to login and then refresh this page to see additional walkthrough videos and helpful content for members only! If you aren’t a WAIM member and want the (awesome) additional content, you’ll need to join here.

*Proud Moment Alert:* These Wandering Aimfully Members have been through Back To Business Basics! Prepare to scroll… 😉

Wandering Aimfully Members partaking in Back To Business Basics!

Alright, with the WAIM community awesomeness out of the way, let’s get these business basics ducks in a row! To get this party started, it’s onto Phase 1: Know Your Numbers!


Phase 1:

Know Your Numbers

We believe there’s a lot more to personal success and happiness than just money. However, as with everything, there has to be a balance.

More money in your business can bring you freedom and flexibility in your life, which are things that can dramatically increase your happiness. Yet, it’s staggering to us how many people we give advice to that don’t have a system for tracking their finances—personally or professionally.

If you’re reading this right now with this face on 😬 because you know you’re one of those people, that’s okay! This program is your chance to change that!

We’re going to break down your numbers into two categories: Revenue and Expenses.

**It’s important to note, none of the methods we’re taking you through are meant to be 100% accurate to the penny. This is not an accounting class. (Thank goodness.) Instead, this is about common sense math and getting ballpark figures so you can make better decisions in your life and business. So try not to obsess over the small stuff and get caught in the weeds with the following exercises. Instead, keep your eye on the big picture and the general aim, which is to get an idea of how money is coming in, how much is going out, and how you can maximize the difference between those two.**

If you’re looking for even more in-depth tutorials on how to use these resources, we offer exclusive walkthrough videos for our Wandering Aimfully Members on how to use Google Sheets and Airtable to track project revenue and expenses. Our memberships open just once a month, so be sure you’re on our email list to get notified when they open back up! For more info on the Wandering Aimfully Membership, click here.


Part 1: Revenue

Here’s the first rule of business basics: You need to know how much money is coming into your business by revenue stream.

It’s not enough to see total numbers in your Stripe or Gumroad or PayPal or Shopify accounts, etc. Knowing what percentage of your overall business revenue is attributed to which projects/products/offerings is crucial for making shrewd decisions on what to put your focus and energy toward at any given time.

For example, if you’re spending 80% of your time on a revenue stream that’s only making you 20% of your income and you’re not seeing results, that’s helpful information so you can shift your focus to a product or project that’s going to get you a bigger bang for your buck.

Which brings us to your first action step:

Action Step:

Determine the monthly revenue for each of your revenue streams throughout the current year.

To do this, you can use a spreadsheet tool like Excel or Google Sheets, you can use our favorite database tool Airtable, or heck you can just write it down with pen and paper! Figure out the right process for you, but be sure to keep in mind your chosen process should be something you can continue to update going forward.

If you’re having trouble knowing where/how to start, fear not! We have some example spreadsheet templates you can use based on systems we’ve created for ourselves over the years (along with step-by-step details on how to use each below):

Jump to steps

Jump to steps

Jump to steps



Step 1: Click on the link to the template and hit File > Make a copy… (this will allow you to edit the template.)

Sales Dashboard Track Revenue 1

Step 2: Download your sales data (in CSV format) from your payment processors one month at a time. Here’s an example using data from Stripe. Under the Payments area, set your filter parameters and Export your data.

Download Sales Data Track Revenue

Step 3: Import your CSV into your Sales Dashboard spreadsheet as a new tab/sheet by going to File > Import… You can import as a new tab or you can replace the “January 2018” tab in the template.

Sales Dashboard Track Revenue Import Data 2

Step 4: Sort your transactions so you can group by product or revenue stream. For example, in my case I sort by the “description” column because that would group transactions for the same course together. (To do this, go to Data > Sort Range…, make sure “Data has header row” is selected and choose the column to sort by.)

Sales Dashboard Track Revenue Sort Range 1

Sales Dashboard Track Revenue Sort Range 2

Step 5: Now that all your transactions for the same product are grouped together, I find that it’s helpful to color code each product. For example, in this image I highlighted Acrylic Explorations online course in green, Better Lettering Course in light coral, and Your First E-Course in medium coral. Then, insert a row at the bottom of each product section and sum up the revenue total for that product. (I find it helpful to highlight all these subtotals in a bright color like yellow.).

Sales Dashboard Track Revenue Subtotal 1

Once you’ve summed the subtotal for each product, you will likely also want to add up those subtotals to get your overall sales for the month

Sales Dashboard Track Revenue Total

Step 6: Add your subtotals to the main yearly dashboard tab. (Tip: If you click into a cell and type “=” you can click over to your monthly sales data tab to select the cell with the subtotal for your product for that month OR you can just type the value in, you choose!)

Sales Dashboard Spreadsheet Tracking Revenue

Repeat this for every month. This should allow you to see on the Sales Dashboard tab about how much each of your products brought in each month of the year thus far. Here’s a look at my former business, Made Vibrant, and my own sales dashboard from 2016!


Step 1: Click on the link to the template and hit File > Make a copy… (this will allow you to edit the template.)

Step 2: Begin updating the spreadsheet with your client projects. List each client project in the top “Client” section. For each client row, you can color in the corresponding cells for the amount of weeks you spent working on the project. This method is especially helpful on an ongoing basis so you can see how many projects you’re working on at one time and your cashflow of when to expect each invoice coming in.

Step 3: Input each of your client invoices, entering the totals in the row of the corresponding client and the column of the corresponding week.

Step 4: The sheet should use formulas to automatically add up the invoice totals for each month from each client so you can see how much you made in total client/project income for each month.

Step 5: If you also have digital products or other income in addition to your client work, you can use the “Product” section in the bottom section of the spreadsheet to input those monthly totals.

Once you have all your various income and projects inputted, you should be able to see how much you’ve made by month, by project/product, and what percentage of your income has come from client work vs. products.



Step 1: Click this link to view the template Airtable base.

Step 2: Click “Copy base” in the top right corner. If you’re already an Airtable user, sign in to see your copied base. If you’re not, sign up! (You can also use our Airtable referral code if you want, we get a $10 kickback if you decide you like it and sign up!) This will now allow you to take our template and make your own edits.

Airtable Revenue Tracker Example base

Step 3: We believe Airtable is so versatile and flexible that you can use it for both client revenue and product revenue. But first let’s start by adding your client revenue. You’ll want to do that under the “All Payments” tab. Create a new row or “record” (as Airtable calls them) for each invoice or payment you’ve collected this year. Fill out the date of the invoice, description, amount, along with the name of the client underneath the “Revenue Stream” column. (You can just type the client name and hit enter which will create a new client from the dropdown meaning you will be able to attribute any additional invoices/rows to the same client.)

Airtable Tracking Income

Now here’s the cool part. The way we have the Airtable setup, there’s also a “Monthly Summary” tab which aggregates all the revenue for a given month. However, we need to tell that summary tab which records (rows) to add up under each month. The next step is how we do that!

Step 4: For each client invoice record, copy the client name under the “Revenue Stream” column and paste it in the “Log” column that corresponds to the month it was paid.


These log columns are linked to the Monthly Summary tab, so by doing this step, you’re effectively telling Airtable to attribute that amount for that particular client under that particular month. Once you paste the client name under the appropriate log, the amount pops up in the Monthly Summary tab. Watch it in action:


Notice that because my third invoice was paid in February, I pasted the name of that client under the “February Log” column so it would show up in the February column over on the Monthly Summary.

Do this for every client invoice record, and then under the Monthly Summary tab, you can find your monthly totals in these summations at the bottom of your view.


The base also has a Total column that adds up the invoices for one client across every month. This allows you to see how much money total each client brought in for the whole year, and then the summation is how you know how much you made in TOTAL across the year.


Now what about if you have products too? We can track that revenue right here in the same sheet!

Step 5: Download your sales data from your payment processor one month at a time. In this example, I’m filtering my payments in Stripe to export payments made in January that were successful.

Download Sales Data Track Revenue

Step 6: Import the raw data from your CSV into a new tab on your Airtable. Click the + button and select “Import a spreadsheet.”

How to Use Airtable To Track Revenue

Step 7: Now, format your raw data! The import shows us the messy raw data of our product sales, with each row showing one transaction, but we need this data formatted to match perfectly with our “All Payments” tab setup.

To do this, we’ll need the first three columns to be Date, Description, and Amount…in that order.

*One important thing to note about Airtable: the first column is your Primary Field and is locked, meaning you can’t just drag and drop to rearrange like you can the other columns.

If your primary column is not your transaction date (mine is actually my Description in the example below), you’ll first want to copy that column, add a new column, and then paste that data like I did here. Then you’ll copy your date data and paste that over the primary column. Finally, just drag and drop the amount column so you’re left with the correct order Date, Description, Amount. If that was confusing, see it in action here:


Now you’ll also want to select the correct Field Types for the Date and Currency columns. To do that, double-click on the column header and select each corresponding field type: Date and Currency.

How to Use Airtable To Track Revenue

Yay! Our data is now correctly formatted.

Step 8: Now, copy/paste your first three columns of correctly formatted sales data into the All Payments tab.

How to Use Airtable To Track Revenue

As a reminder, each record or row represents a payment made to your business. So where in the context of clients each row was a paid invoice, now in the context of products, each row is a sales transactions.

Now we need to assign a revenue stream, but to make that easy, let’s group our transactions so that transactions from the same product are grouped together.

Step 9: Sort all your payments by “Description.” Choose Sort at the top of your tab, then from the dropdown select sort by “Description” and hit Apply.

How to Use Airtable To Track Revenue

This basically alphabetizes your transactions by description, which allows us to easy fill in the Revenue Stream column with the product name.

Step 10: Fill in the Revenue Stream column for each transaction with the product name. (You should be able to tell based on the Description text.) You only need to type it once, then you can drag the bottom right corner down to auto fill the rest of the rows for that product.

How to Use Airtable To Track Revenue

Step 11: Now we need to “log” each sale in the correct month so it will rollup in our Monthly Summary tab. As you remember from the steps above, just copy the Revenue Stream column and paste in the correct “Log” column. If you exported your sales data one month at a time, this will make things especially easy because you can just select every cell in the Revenue Stream column that corresponds to a January transaction and paste it in the January Log column.

How to Use Airtable To Track Revenue

Reminder: If you’re looking for even more in-depth tutorials on how to use these resources, we offer exclusive walkthrough videos for our Wandering Aimfully Members on how to use Google Sheets and Airtable to track project revenue and expenses. Our memberships open just once a month, so be sure you’re on our email list to get notified when they open back up! For more info on the Wandering Aimfully Membership, click here.


Part 2: Expenses

Hopefully, by now you have an idea of how much money your business efforts are bringing in and exactly how much each of your clients/revenue streams/products are contributing to your bottom line. But money coming in is only one part of the equation. We also need to understand how much money is going OUT.

That doesn’t just go for your business, that goes for your life as well.

Do you know exactly how much it costs you to live? Do you know how much you spend on shopping or eating out or entertainment each month?

This is where tracking your expenses and categorizing them comes in handy.

In our experience, so many people avoid looking at their spending habits because of the shame they feel about how much money they spend. Whether it’s because you’re in debt, or you’re making less than you want to be making, you might be avoiding your bank accounts to avoid these kinds of feelings.

But, the important thing to realize is that ignoring your finances doesn’t make them go away. The only way to stop that cycle of shame is to confront your habits and make changes to start spending smarter.

This was one of the very first things we did when we were trying to claw ourselves out of debt, and it was a crucial step for us in taking back control of our finances.

Not to mention, for every dollar less you spend in your life and business, that’s one more dollar of profit you get to keep and save or pay off debt with.

Action Step:

Track and categorize your expenses for the past three months using our ETAC exercise.

What’s ETAC you ask? ETAC stands for Expense Tracking And Categorization, an exercise we developed after being dissatisfied with the budgeting software we experimented with out there. We wanted a completely custom way to track our expenses and group them into categories, so we created our own method. (Jason also loves that the acronym sounds like the word attack, which is appropriate since we used this method to attack our mountain of debt.)

Just like in the revenue section, we’ll walk you through how to categorize your expenses using both Google Sheets and Airtable.



Step 0: Make a copy of the Expense Tracking and Categorization (ETAC) Google Sheets for yourself (File > Make a copy).

Step 1: Download the data from all your accounts and credit cards for the past three FULL months as CSVs. (CSVs might also be titled “comma delimited tabs” in your account download options.)

Step 2: Import your CSVs as individual tabs into the ETAC spreadsheet. (To do this, go to File > Import > Upload your CSV and select “Insert new sheet” under the import options)

Step 3: Format your data so it’s all uniform. Make sure you have three columns in this order: Date, description, and then amount. Be sure to format the date column as a date and format the amount column as a currency.

NOTE: I like to keep all expenses as negative numbers. Make sure it’s consistently negative OR positive across every debit or credit account you have because if not, your transactions may cancel each other out giving you an inaccurate total. Whether it was paid for on a credit card or with a debit card, if it was an expense (money going out) I make sure it’s formatted as a negative number.

Also, delete any transfers or credit card payments. We’re just looking for how much money went out the door, not how much was moved around between accounts. It’s REALLY important you remove these across every tab or else, again, your totals will cancel out and be substantially off.

Step 4: Once the data in all of your tabs is formatted uniformly, copy/paste each list of transactions into one sheet, the sheet in this spreadsheet labeled “All Transactions.”

Step 5: When every transaction has been pasted over to the All Transactions tab, sort by date and then fill out the appropriate “Month” column.

(This will make it easier to filter your data and see transactions by month.)

Step 6: Once months have been applied, go through every transaction line by line and assign a category in the category column.

You can use the category names already listed out on the Monthly Comparison sheet OR you can create your own.

Step 7: Now it’s time to add up your monthly totals by category and add to the Monthly Comparison tab. To get all the transactions in a certain month in a certain category, first Filter by one month, and then sort by category.

To do this, go to Data > Create a filter… and select the down arrow on the month column to check off which month you want to view at a given time. We recommend only viewing one month at a time when you’re adding up your category totals. Once you have just one month’s transactions in your view, then select the down arrow on the category column and hit Sort.

This will show you transactions in the same month AND group transactions in the same category together. This will make it easier to sum your totals over on the monthly comparison sheet.

Step 8: Now that you have transactions for one month only, grouped by category, you can head over to the Monthly Comparison sheet, and use the SUM formula to add up the total for each category within that month.

Also notice this will start to adjust your monthly expense totals, your three-month average, and your category average.

You can add more categories or more months to your Monthly Comparison tab, just be sure that you update the total formulas so they include those.

Step 9: Repeat these steps until you have the total amount spent for every category and every month.



Step 0: Make sure you’re viewing the Expense Tracking and Categorization (ETAC) using Airtable.

Step 1: Download the data from all your accounts and credit cards for the past three FULL months as CSVs. (CSVs might also be titled “comma delimited tabs” in your account download options)

Step 2: Import your CSVs as individual tabs into the ETAC Airtable Base. (To do this, click on the + icon by the tabs and select “Import a spreadsheet”).

Step 3: Now we need to format your transaction data so it’s all uniform. You want to have three columns in this order: Date, description, then amount.

Be sure to double click on the date column and make the field type “Date” and double-click the amount column to make the field type “Currency.”

NOTE: I like to keep all expenses as negative numbers. Make sure it’s consistently negative OR positive across every debit or credit account you have because if not, your transactions may cancel each other out giving you an inaccurate total. Whether it was paid for on a credit card or with a debit card, if it was an expense (money going out) I make sure it’s formatted as a negative number.

Also, delete any transfers or credit card payments. We’re just looking for how much money went out the door, not how much was moved around between accounts. It’s REALLY important you remove these across every tab or else, again, your totals will cancel out and be substantially off.

Step 4: Once your data is all formatted uniformly, copy/paste each list of transactions into the Expense Tracking tab under the All Expenses view.

Step 5: When every transaction has been pasted over to the Expense Tracking tab, sort by date and then fill out the appropriate “Month” column. (This will make it easier to filter your data and see transactions by month.)

Step 6: Once months have been applied, go through every transaction line by line and assign a category in the category column.

You can use the category names already listed out on the Expense Summary tab OR you can create your own.

Step 7: Here’s where the magic happens! In order to pull in the total spent on a given category in a given month, we need to “log” our expenses in the corresponding monthly log column. To make this easy, go ahead and filter all your transactions by one single month.

Then, copy the category column for that month, and paste it in the corresponding monthly log column. In this case, we’ve filtered only July transactions, so we copy the category names and paste them in the July Transactions column.

The “July Transactions” field is linked to the Expense Summary tab, so if you go to the Expense Summary, you’ll now see the total spent on each category in the July column.

Step 8: Repeat this for each month of data. Filter by month, then copy/paste the categories into the log column matching that month.

Finally, you’ll be able to see your total spent each month by category. You can also use the summation bar at the bottom to see how much total you spent on a given month.

There are a few more fields on the Expense Summary tab you might find interesting.

  • Budget: Fill out this field with your budget for each category.
  • Monthly Average: This formula will average however many months you’d like to find out your average expenditure for that category. **Be sure to edit this formula and only include the months which have data or else the $0 months will drag down the average.
  • Over/Under: This tells you whether your average is over or under the budget you’ve set.
  • Alert: This simply updates with a 😎 or a 😬 depending on whether you’re over or under budget.
  • Total per category: Shows you how much you’ve spent in total for that category. might be especially helpful for more yearly categories like Travel.
  • Current Month Difference: You can update this formula with the current month and it will tell you how much you have left in your budget for that month.
  • Current Over/Under: Tells you if your over or under budget based on the Current Month Difference formula.


Summary: Questions & Action Steps

As a recap, here’s what you should have used the steps above to do for this lesson:

  • Track your revenue for the current year using one of the three methods outlined above
  • Track your expenses for at least the past three full months using the methods outlined above

Now here are some critical questions to ask yourself as you take a look at the data:


  • What revenue stream or product brought you the most revenue this year for the least amount of effort?
  • What revenue stream or product brought you the least amount of revenue this year for the most amount of effort?


  • Did you spend more or less every month than you expected in your head?
  • List three categories that you know you could cut back in to spend less every month. (Bonus: Go through every category of expenses and look for ways that you could streamline your expenses.)
  • What will be your budget for each category going forward?

Once you get your numbers in order, come back next week for Phase 2, all about where you’re spending your time and how you’re maximizing your productivity!


Phase 2:

Where Does Your Time Go?

It’s time for phase two of Back To Business Basics, let’s not waste a single second! Alright fine, we’ll stop with the silly time puns. We won’t, however, sugar coat how important it is that you start to manage your time like we showed you how to manage your money: By actually looking at where your time goes!

Similar to phase one (Know Your Numbers) we want to show you how we’ve been able to find more hours in our days by examining where we’re actually spending our minutes and hours (just like where you’re spending your dollars). There are two exercises in this section: The first is a more hands-on Time Tracking Journal that will help show you where every hour of your day is actually going. The second includes two apps you’ll install on your computer and phone which will track your daily habits and show you where your time goes.

There is not a doubt in our minds that you can make some drastic changes in how you manage your time in just a few short days. They key is that you need to understand where you’re currently spending your time and not try to fix everything overnight.

If we can help you gain one hour back each day, you’ll have an extra 30 hours in the next month that you didn’t have before!


Time Tracking Exercise #1: Time Tracking Journal

We have two time tracking exercises for you to do and while each is important on its own, we would HIGHLY recommend doing both (you can do Exercise #2 alongside #1 with almost no extra work!)

What is a Time Tracking Journal? Quite simply, it’s a log you keep of what you’re doing during every hour of the day.

The point of keeping a Time Tracking Journal is to see if your mental time accounting matches your reality. We know what it’s like to think: “Where did the day go? What the heck did I do all day?” By keeping a written log of what you’re doing each hour of the day you can see exactly where your time is going and you can be honest about changes that need to be made in your daily life.

Action Step:

Understand how you’re spending every hour of your day and find ways to improve your habits and become more productive.

There are three ways we recommend setting up a Time Tracking Journal and we’re going to let you play a bit of Choose Your Own Adventure here. Because we know you’re an action-taking person and already did Phase One (Know Your Numbers) we’re going to assume you can create your own Time Tracking Journal in one of three ways:

  1. Google Sheets: Very straightforward, just enter in what you did for every 30-minute block of time.
  2. Airtable: Same as Google Sheets, just using Airtable instead.
  3. Pen and Paper: Same 30-minute blocks, except you physically write them down in an actual journal (ooooh, ahhhhh!)

IMPORTANT: We recommend keeping a Time Tracking Journal for at least three days straight. We promise it will not derail your entire life and if you want to track your time for more than three days, feel free to do that.

Time Tracking Journal

Because our Time Tracking Journal is exactly the same whether you use Google Sheets, Airtable, or pen and paper, we’re not going to walk-through each one. This should be a very simple exercise to keep up with and we’ll share the step-by-step process using Google Sheets as our example…



Step 1: Commit. Commit to yourself and to this simple exercise. YOU GOT THIS!

Step 2: Set a recurring hourly alarm or timer on your phone or calendar. You’ve probably never tracked your time on an hourly basis, so make it easy on yourself and have some sort of reminder that pops up each hour telling you to record where you’ve been spending your time.

Step 3: Track your time via 30-minute blocks in two ways.

What Where You Working On? The first column you want to track is the bigger task or project you were working on (example shown in image: “Wrote sales page copy for my Branding Course”).

Time Tracking Journal - What were you working on?

What Else Did You Do? The second column you want to fill out is if you spent time on social media, checking email, etc (example shown in image: “Listened to Armchair Expert podcast and checked Instagram”).

Time Tracking Journal - What else were you doing?

Step 4: Track all your time spent throughout the day! Do not wait until the end of the day to go back and fill out your Time Tracking Journal. You won’t remember exactly what you worked on and you’ll continue in the cycle of not knowing where your time has gone.

Step 5: At the end of each day, review where you spent your time. Fill out the final column (Could This Be Improved?) with a YES if it could. How many hours could you improve? How many hours could you apply toward more productive things knowing how you actually spend your time?

Time Tracking Journal - Could this be imrpoved?

Step 6: At the end of the three days (minimum) identify what small changes you can make in your daily life to get more time and focus back for what matters.

  • Instead of checking email and social media sites all day long, could you instead only check them 2-4 times throughout the day at set times (8am, Noon, 4pm)?
  • Instead of trying to work on your side project at night, should you try to work on it first thing in the morning or at lunch?
  • Instead of doing “adulting” every day of the week, should you try to move all your errands/personal stuff to one or two days of the week so it doesn’t cut into work time?

Note: The idea for tracking your time is NOT to optimize your days to have as many work hours as possible. The idea is to make sure you see where your time is going and to ensure you’re not letting time slip through the cracks and that you’re allocating time where YOU want to be spending it to reach your life and business goals.


Time Tracking Exercise #2: Install the RescueTime and Moment apps (they’re free!)

As we mentioned in Exercise #1, we recommend using RescueTime and Moment alongside keeping a Time Tracking Journal. Using the RescueTime and Moment apps are a completely passive way of tracking where you’re spending your time and attention when using your computer or phone. Does it sound like the results might be scary for you? GOOD! We want you to confront your habits and how you’re currently spending your hours otherwise you’ll continue to do what you’ve always done (just like taking a look at your expenses and revenue does for your money!)

What is RescueTime? It’s a free app that you install on your computer that tracks how much time you spend surfing the web, using certain apps, browsing Facebook, etc.

What is Moment? Similar to RescueTime, except it tracks your time on your phone (iOS only, Android options below).

*We are not being paid to endorse RescueTime or Moment, we simply believe they’re awesome tools that can show you some really interesting data about how you spend your time.

Action Step:

Determine where the percentage of your time is going for your business and life, and identify your ideal time split.

The wonderful part about the Action Step for Exercise #2 is that RescueTime and Moment are going to do all the work for you (and with nice charts and graphs)!



Step 1: Sign up for a completely free RescueTime account here.

Step 2: Install the RescueTime app on your computer.

Step 3: Let RescueTime do its thing! That’s it. You’ve done all the steps to get RescueTime installed.

Step 4: View your Daily Dashboard in your RescueTime account after your first full day of having it installed. What do you notice? What stands out to you? What do you need to change about how you spend your time on your computer?

RescueTime Daily Dashboard

Step 5: Once you’ve had RescueTime installed for a week, you’ll get emailed a nice report. What can you learn from your weekly habits that you need to change?

RescueTime Weekly Report



Step 1: Download the app for iOS (for Android checkout App Usage or Quality Time).

Download the Moment app

Step 2: Say “Yes” or “Okay” to all the steps when you first launch the Moment app. Let it track your time and your location to give you the most accurate time tracking data.

Step 3: Let Moment do its thing! Yep… that’s all you need to do.

Step 4: After a full day of having Moment installed, review your screen time habits. Are you surprised by where you spent your time on your phone? Maybe a bit shocked? What do you need to change? Remember, you don’t have to go cold-turkey, but small changes to your daily usage can go a long way in giving you more time back to put towards other things.

Moment time tracking app

*One thing that’s neat about RescueTime and Moment is that the paid versions of their products have ways to help you block certain activities. Let’s say you have a particularly hard time not being on Facebook, RescueTime and Moment’s paid versions (very cheap!) can help block Facebook for you for certain periods of time.


Summary: Questions & Action Steps

Recapping Phase Two, here’s what should accomplish by following the two exercises above:

  • Create a Time Tracking Journal to track every hour of your day for at least 3 days in a row
  • Install RescueTime and Moment to passively keep track of your computer/phone usage

Here are the questions to answer as you track your time and look at the data:

Time Tracking Journal:

  • Where are you wasting the most time and how much time could you get back to apply to other things each day?
  • What habit do you need to break that you know isn’t helping your life or your business?
  • What habit do you want to put in place right now to get more time back?


  • What percentage of your time is currently going to your business?
  • Is the percentage of time going toward your business being spent on the RIGHT things?
  • What percentage of your day are you wasting that could be applied to better your life or business?

You WILL get more things done and become a more productive person if you take a look at how you’re spending your time each day. The most important part is to admit where you could be doing better and starting making small changes today.


Phase 3:

Evaluating Revenue Streams

Chances are you’ve asked yourself this age-old question as a business owner:

What area of my business should I focus on next?

Well, we’re going to try to help you answer that, but we do have to do a little bit more legwork to get there. Let’s recap what you’ve accomplished thus far.

In Phase One: Know Your Numbers, you should have ended up with a much clearer picture of the profitability of each of your projects or revenue streams.

In Phase Two: Where Does Your Time Go, you should have ended up with a few ways to make your days more intentional and productive.

Armed with deeper knowledge about the two most fundamental resources you have (money and time), it’s time to take a hard look at your revenue streams to understand the single greatest opportunity you have to move your business forward.

In this section, you’ll be evaluating the health of your revenue streams to identify the product or project with the greatest potential upside. We’ll also talk about how to know when it’s time to optimize what you already have going or create something entirely new.

Creating a revenue stream comparison chart

Before you can determine what revenue stream to focus your attention on, it helps to see everything side by side so you can make comparisons.

Action Step:

Fill out the revenue comparison chart with every product or revenue stream from your own business.

Comparing Revenue Streams Chart

Click here to download this template as a PDF

Here’s how we recommend you complete this revenue comparison chart.

Step 1: Download the PDF above or create your own table with 4 columns, listing out your various revenue streams as rows in the first column.

If you have one broad revenue stream such as client work (if you’re a designer, for example) we recommend breaking that down even further into categories. For example: web design clients, logo design clients, etc. This will allow you to make more specific conclusions about what to focus on.

If you have various product offerings, write each one out on a separate line.

Comparing Revenue Streams Chart

Step 2: For each revenue stream you’ve listed out, now write down the “input” in terms of money AND in terms of time it requires to operate that revenue stream.

Three things to note:

1. It helps to specify a timeframe for the input/output to make sure you’re comparing apples to apples. I recommend using one month. If that’s the case, you want to include how much operating cost you pour into that product or offering in a month’s time and how much time you contribute to it on a monthly basis. It may help to estimate your time by the week and then multiply by 4.

2. You may also want to assign a monetary value to your time in order to later compare it with that revenue stream’s output. For example, you could say your time is worth a flat $100/hour, so a revenue stream that takes 30 hours a month and $300 to run, would actually require $3,300 of input.

3. If you have general expenses that aren’t revenue stream specific, take that monthly total and divide it evenly among your various revenue streams so it’s a distributed cost.

4. As far as time goes, for products you want to think about ongoing input or operating input for the purposes of comparison, not necessarily the time it takes up front to create the product.

Comparing Revenue Streams Chart

Step 3: Consult your revenue tracker from the Know Your Numbers section and use the totals to fill out the output column.

If you completed Phase One, then you should know how much on average you make in a month per revenue stream. If you didn’t already complete that exercise, be sure to sum up those totals and write them down in the output column.

Comparing Revenue Streams Chart

Step 4: Now this last part is really crucial for the decision-making that will result from this comparison. Finally, use the fourth column as your “X factor”—aka one more comparison criteria that matters to you.

This X factor could be enjoyment (how much you like working on that revenue stream) or it could be alignment (how well it lines up with your personal values) or it could be something like “future vision” (how well it meshes with the vision of where you want to steer your brand.)

The point is, you get to choose. Write it down as the final column header and then write in a number between 1 and 10 for using that criteria for each one of your revenue streams.

That should complete your revenue comparison chart and it should look something like this:

Comparing Revenue Streams Chart

Using the revenue stream comparison chart to make decisions

Now that you have all this information, it’s time to use it!

We want to use the comparison chart to look for the revenue stream with the greatest opportunity for impact. This means finding the revenue stream with the most efficient output to input ratio (ie. greatest output for the least input) but also with the highest X factor score.

Use an efficiency score to help you!

One way to do that is to divide the output column by the input column to come up with an “efficiency score.” This makes it super easy to see the stream with the greatest output for least input, because the score will be the highest number.

Comparing Revenue Streams Chart

But, don’t forget, we have to also consider the X factor criteria. Your revenue stream with the highest efficiency score might actually be the one you enjoy the least, which isn’t necessarily the best thing to focus on going forward. Instead, look for revenue streams with relatively high efficiency scores AND high X factor scores.

For example, you can see “Branding only clients” and “Branding ecourse” in the example have a similar efficiency score BUT one of them has a much higher enjoyment score:

Comparing Revenue Streams Chart

Using the example, now I’m able to see that out of all my various projects, the branding e-course is probably worth investing in and focusing on. While it may not be the source of greatest revenue (YET) it’s efficient at making money (meaning time poured into it will see a notable return) AND it’s something that I enjoy doing.

This is how you can use this comparison chart to choose what to focus on.

Keep in mind, you can make up your own rules too. Maybe instead of the efficiency score method, you want to choose the revenue stream that is making you the most money with the most enjoyment, and you don’t care how many hours or how much money it takes to operate. That’s okay. The idea is just to think critically about your various projects and make decisions based on real data, rather than simply feeling stuck or overwhelmed with no idea of what to focus on.

What about creating new revenue streams?

Now, you might be asking yourself, what if none of my current revenue streams are really working? Is it time to try creating something new?

The answer is maybe. But we always try to caution people about immediately jumping to the conclusion that it’s time to create something new. Why? Because it’s all too easy to get caught up in “shiny object syndrome.” The nature of creativity is that we get excited about projects in the beginning and once time goes on they begin to lose their luster.

Part of running a successful and profitable business is learning how to use your time and energy in the most efficient, impactful way possible. Creating something new often requires you to reinvent the wheel and while it may be exciting, it can be a drain on your resources. Instead, it’s advisable to find ways to fall back in love with your existing projects or find ways to breathe new life into those.

Summary: Questions & Action Steps

Recapping this phase, here’s what you should accomplish by following the steps above:

  • Fill out the revenue comparison chart with every product or revenue stream from your own business and your own X factor criteria

Here are some questions to answer as you take a look at your revenue streams:

  • Based on the data, what revenue stream do you feel has the greatest opportunity for impact in terms of moving your business forward?
  • What are three ideas of things you could try in order to increase revenue for that particular revenue stream?
  • If you spent the next three months investing time and focus into that one revenue stream, what’s a realistic goal for boosting the revenue of that one stream?
  • Finally, did anything surprise you about the input of your various revenue streams? Using what you already learned from Phase One and Phase Two about your money and time resources, are there ways you could cut down on expenses or ways you could be more efficient with your time to improve the efficiency score of any of your revenue streams?


Phase 4:

Choosing A Focus And Making An Action Plan

Hopefully, by now, you’re starting to see a clear path forward on what to focus on next. If not, this final phase of Back To Business Basics is the time to make that decision and create a specific action plan moving forward.

It’s time to decide what revenue stream to focus on, what specific goal(s) you’re working toward, and come up with some clear tactics on how to get there.

Choosing a revenue stream to focus on

If you haven’t already, start by looking back at Phase Three and your revenue stream comparison chart to determine which revenue stream has the highest potential impact on your business. You can base this decision off the more analytical route we went over in Phase Three about checking your efficiency scores and comparing with your X factor.

If you’re still struggling after that, another thing we consider when choosing where to place our focus to move things forward is to look at everything we’re currently working on and identify what we call the Brick Walls and Cracked Doors.

“Brick Walls”

Brick Walls are what we call obstacles you repeatedly find yourself bumping up against over and over with one of your revenue streams.

Example Brick Wall: Let’s say you’re a designer and you constantly find yourself working more hours on projects than you estimated, meaning ultimately you’re getting paid less than you’re worth for the time you spend on client work. You’ve tried to optimize your process for estimating your time when you quote projects, but inevitably you find yourself logging overtime project after project.

Example Brick Wall Solution: It might be time to consider shifting your focus away from that revenue stream and trying something like digital products so you’re not trading time for money—something that consistently gives you headaches.

“Cracked Doors”

Cracked Doors, on the other hand, are what we call slivers of opportunity that present themselves or an area where you feel the momentum building in your business.

Maybe you have a particular blog post on a topic that’s really taking off an getting a lot of traction. Maybe you have a client who you’ve worked with a few times and they’ve floated the idea of paying you a monthly retainer. Maybe you have an influx of emails asking you if you offer a particular offering that’s not listed on your website. These are things to take note of and things that may not come through in the “data” of your comparison chart from Phase Three.

Note when it comes to Cracked Doors: Beware of shiny object syndrome! There’s a difference between spotting a smart opportunity for your business and just being bored of what you’re already doing so you’re craving something new. Part of being a shrewd business owner is being able to spot the difference. Creating something entirely new should actually be the last thing you prescribe your business for all the reasons outlined in the final section of Phase Three.

Now, with all these things considered, it’s time to pick your pony!

Action Step:

Using the revenue stream comparison chart to guide you, choose ONE single area of your business to make the primary focus for the next three months.

Clearly defining your three-month goal

Once you know WHAT to work on, it’s important to define what “working on it” is aiming to get you. We need to establish a goal. Yay goals!

Project out your next 3 months of revenue

Head back to your Revenue Tracker from Phase One and determine realistic revenue goals for the next three months. We like to measure our previous (actual) revenue against upcoming (projected) revenue multiple times throughout the year. Now is the perfect time to project your revenue by project or client for the next three months (feel free to add it right into your Revenue Tracker sheet or Airtable)

Write down any time-related changes you need to make going forward

You may also want to determine a time-related goal. Based on what you learned in Phase Two: What Do You Spend Your Time On, it’s not just about spending more hours working. It’s about spending the right hours doing the right work. It may make sense for you to write down how many hours a week you’re trying to keep these growth efforts constrained to, so you don’t just find yourself in a situation where you’re feeling burned out. Remember, this is also a way of keeping your input (your time cost) as low as you can, making your revenue stream as efficient as possible.

Is it time to create (or finish working on) a new revenue stream?

If you’ve gone through all phases of Back To Business Basics and believe now is the time to create a completely new revenue stream, now is a great time to schedule the production and estimate your revenue. A couple questions to answer that should help you:

  • What is a realistic timeline to launch your new revenue stream?
  • What needs to get done in the next few weeks/months (carve out time on your calendar!)
  • Can you get pre-orders for your new revenue stream to prove your hypothesis that people want it?
  • What is the smallest best version you can get launched as quickly as possible?
  • What might you have to sacrifice in order to get your new revenue stream up and running?
  • Once your revenue stream is launched, what will you do afterward to keep it selling consistently?
  • Can you surprise and delight the first customers of your new revenue stream?

Creating your action plan

You know what to focus on, you know what you’re aiming for, but now it’s time to determine what exactly you’re going to do to improve your revenue and to create a clear action plan to make that happen.

Part of the overwhelm of being an entrepreneur is that there are an endless amount of things you can try or change when it comes to your business in order to improve it. To make these options more manageable, we break them down into three core categories: 1) Process; 2) Product; or 3) Promotion.

Here are some ideas of how to beef up your revenue stream by improving these three areas:

Product: Is your product/service everything your customers need or is it missing something?

To get the answers, consider getting feedback from existing customers by emailing them simple surveys with just a few questions (we love Typeform for surveys).

  • What made them buy?
  • What problem do they feel your product or service solves for them?
  • What did they really enjoy about your product or service?
  • What did they think could be improved?

Sending a survey via email is great, but don’t hesitate to hop on Skype to chat face-to-face. Some of the best feedback we’ve ever received for our businesses has come from actual conversations with existing or potential customers. Make sure you let them know you want honest, constructive feedback and then see if there are any recurring themes in that feedback.

Similarly, you may want to get feedback from people who don’t buy. For example, with our Wandering Aimfully membership, if someone clicked on our sales page and showed interest but didn’t buy, we email them a few days after launch as ask them to fill out a short survey. This allows us to see if there’s anything we’re missing in terms of what our membership offers or how we’re communicating it.

Promotion: Is there a disconnect between your product/service and your customers?

If you know your product solves a particular problem and its top-notch, it’s possible your problem lies with the promotion. Any of the following could be to blame for this disconnect:

  • The wrong price point for the value you’re providing
  • Not enough people know about your offering
  • You’re not communicating the problem your offering solves clearly enough*

*We’re guilty of this one and we see it all the time. It’s human nature to focus on the features of what you sell in your sales copy, instead of what problem it solves for your customer (the benefits). The easiest way to figure out if you’re not communicating the problem is to refer back to survey results to the question you asked about this. You could also have someone else who has similar experience running an online business review your sales copy to see if it’s speaking to the features (wrong) or the benefits (right!)

And here are some potential solutions to your promotion problems:

  • Adjust the price or add more value to your offering
  • Find new audiences to tap into to promote your offering
  • Adjust your website/sales page (or sales email) copy or experiment with ways to showcase the transformation your offering provides

Process: Is there a way to streamline your process or reduce expenses?

Finally, if your product is great and you feel you’re getting a steady influx of customers, it’s possible the improvements could lie in your process.

Does this revenue stream take up too much of your time? Are there parts of the process that could be smoother for your customer or for you?

For example, maybe you find with your clients that a lot of time is wasted on your first call together just getting an understanding of the project specifics. Could you develop an intake survey you could send via email that would give you background info to make your meetings more productive? Then you could have a first call that’s much more streamlined. Things like this may require a time investment up front but will make you more efficient over time.

Ultimately, you should have an understanding by this point of what processes might need fixing in your business (hint: many of them will have to do with time allocation and management). What have you seen after going through the first three phases of Back To Business Basics that need attention?

Action Step:

Using the ideas above (or your own), write down THREE improvements you plan to make to your chosen revenue stream in order to reach your three-month revenue goals. Bonus points if you want to share those with us via email for some extra accountability.



Making Your Plan Real

It’s not enough to just write a few tactics and a revenue goal down on paper. You have to find a way to really integrate this plan into your schedule and your existing workflow.

Remember, business is a complicated puzzle. There are so many moving parts, and you may not find immediate success or growth with the first thing you try. If you implement your chosen three improvements and don’t see the life you’d hoped for, experiment with three more. Succeeding with your business is about taking imperfect action, testing your assumptions, and utilizing your newfound focus.

If we can help on your journey, feel free to reach out to us!

Instead Of Focusing On Growth, We Want To Focus On Enough: Our Journey To 330

September 1, 2018

Heads up: This post was first created on September 1, 2018 and will be updated monthly. Be sure to check back for updates!

We’ve decided to publicly share our journey to making “enough” money with Wandering Aimfully. The idea behind this is not to show off how much money we’re making, the idea is to show exactly HOW we’re doing it.

One of our core values here at Wandering Aimfully (or WAIM, as we like to abbreviate it and will do throughout this post) is transparency.

We believe the world is a better place when we’re sharing the FULL picture, authentically and truthfully.

Transparency becomes especially important to us when it comes to money because there are so many emotions and thoughts that often get tied to money (greed, shame, self-worth, happiness, embarrassment, etc), some of which can present challenges to the way we pursue our goals.

Before we get too deep into things, you might not know who the heck “we” are, in which case you may want to mosey on over to our About Page to learn more about us—Jason and Caroline Zook. If you just want the TL;DR version: We’re a husband and wife creative duo, with no employees, running our own businesses for over a decade, currently living and working together in Southern California. For good measure, here’s a super cute photo of us…

Jason and Caroline Zook, Journey to 330

Now that we’ve met, let’s talk about this goal of getting 330 people to join our Wandering Aimfully Membership.



Our Goal: Reach 330 Paying Members Within 12 Months (aka Journey to 330)

From years of experience, we know how it easy it is to get fixated on making more money. Yes, we know how good it can feel to see a couple extra thousand dollars in your bank account after a big launch, but we also know the mental toll it takes to constantly be in promotion, marketing, and sales mode. That’s partly why we’ve decided to give ourselves an “enough number.” When we finally reach this number, we can stop feeling the constant pull of promotion. We can focus fully on the amazing community we’ve built, rather than constantly be searching outside of the community for more members.

We also believe that defining your enough is the only way to ever feel satisfied. So often we focus on the vague word “happiness” without defining what it really is. We believe a big part of happiness is this notion of satisfaction. So, let’s explore for a second this idea of satisfaction.

One definition we found for the word satisfaction was:

The pleasure derived from the fulfillment of one’s needs.

Think of your wants and needs as an empty bucket. The pursuit of fulfillment is the quest to fill that bucket, and satisfaction is the pleasure you get from recognizing it’s indeed full.

But here is the root of why satisfaction seems to be so elusive:

So many times in our lives, we don’t actually define our individual/actual needs. We never stop to decide how big the bucket needs to be. We never stop to decide how much is ENOUGH.

How can we be fulfilled when we have no idea how big the bucket is we’re trying to fill?

Without defining what your needs are—without setting that benchmark—you will just keep trying to fill a bucket that’s endlessly expanding. That’s a recipe for a lifetime of discontent.

Instead, if you want to experience satisfaction (ie. happiness), you need to define how big your bucket needs to be…and then you need to recognize it when it’s full.

Or, in other words, you need to figure out how much is ENOUGH.

For us, our enough is 330 Wandering Aimfully members

Getting to 330 paying Wandering Aimfully members within 12 months time will net us $33,000 in monthly recurring revenue (MRR). After we hit that number, we’ll close the proverbial sales-doors and stop accepting new members. We aren’t interested in continuing to grow our membership community (and make more money) just because we can.

In a highly digital world, we want to plan for and offer a personalized touch.

Why 12 months? Each month we’ll limit new memberships to 30 per month, so technically we should be able to get to our goal before 12 months (yay, math!), but we want to leave a bit of buffer in our membership signup planning especially because we know we’ll have some customer cancellations (aka churn). Limiting our memberships to 30 new people per month allows us to deliver as much of a personalized experience as we can, including some non-digital stuff.

Additionally, limiting the amount of new monthly members ensures that the community doesn’t feel crowed or overwhelming to our existing awesome members. It’s important to us to preserve the culture of the community, which we know to be one of our major selling points and differentiators.

For context, it might also help you to know how our membership pricing works. It’s very simple:

  • $100 per month or,
  • $1,000 per year

Both membership options include the exact same thing, the annual option simply saves someone a couple hundred dollars by paying in advance. If you want to learn more about what we include in our WAIM Membership, click here.

We’d be remiss if we didn’t mention some important advantages we have in this Journey to 330:

  1. We’ve been working for ourselves since 2007 (Jason) and 2013 (Caroline), with both of us focusing on helping creative entrepreneurs since 2014.
  2. We have a (now combined) email list of 16,000 subscribers.
  3. We have a (now combined) website that averages 50,000 visitors per month.
  4. Our membership community had 400 active members grandfathered (or grandmothered) in from a previous project called BuyMy/BuyOurFuture.

There’s no denying those are helpful pieces of this puzzle that we already have at our disposal. That being said, this is a new business offering for us and for our audience.


How did we get to $33,000 MRR as our GOAL “enough” number?

We told you we value transparency, didn’t we? Well, it’s about to get really real up in here.

A fundamental part of our approach to work and life is a philosophy we call Working To Live. Part of this ethos is the belief that living a fulfilling life begins with establishing our ideal lifestyle and then reverse engineering our business decisions to support and align with this lifestyle.

Using this approach, we first identify what we WANT, and then we back out how much money we need to get there.

That equation is how we arrived at our specific number of $33,000.

“We first identify what we WANT, and then we back out how much money we need to get there.”

Our average monthly living expenses: $12,000

That number may or may not seem outrageous to you. It’s taken a lot of restraint not to write paragraphs of text defending how much we spend in living expenses every month. But therein lies the problem when it comes to money: we constantly feel like we’re being judged or we feel we have to be on the defensive about our spending.

So, how about this as justification…We spend this much money every month to live lives we absolutely love. It’s awesome to be able to do that, right? We agree! But, it wasn’t always this way. In fact, it was just back in 2013 we spent $4,000 per month and could barely make ends meet (you can read our getting out of debt guide here).

Here are how our monthly living expenses break down in broad strokes:

  • Rent: $4,000
  • Groceries: $1,500
  • Entertainment/Coffee/Eating Out: $1,000
  • Travel*: $2,000
  • Health & Insurance: $1,000
  • Tesla Payment: $1,000
  • Plaxico (our dog): $400
  • Misc (utilities, cleaners, etc): $500
  • Other (donation to causes**, Acorns, etc): $600
  • Total: $12,000 spent per month

*We don’t actually spend $2,000 on travel per month, but the past two years we’ve averaged spending about $20,000 on travel per year. We put this as a monthly “expense” to keep a watchful eye on it.

**Donating to causes we care about is a big part of our Journey to 330 goal as you’ll read in a moment.

Our average monthly business expenses: $5,000

Our business expenses have fluctuated quite a bit over the years due to how many different businesses and projects we have. That being said, one of our huge goals with starting WAIM was to streamline all of our projects into ONE membership and create a much more predictable set of business expenses. We believe this number is actually going to decrease over time, but for now we’re using a comfortable monthly average (which we’ll share more about in detail as the monthly updates continue to get added to this post).

The average monthly amount we’ll set aside for taxes: $3,000

Oh taxes, you necessary evil, you. First, we aren’t going to be those people that gripe about paying taxes. We understand and believe in taxes. This monthly average number will absolutely change over time, but we’ve decided to base it on our previous two years of business (taking what we paid in total taxes annually and dividing that by 12 to get a monthly average number). We do a /decent/ job of setting aside money for our taxes each year, but with a more predictable MRR going forward, this will get much easier!

The average monthly amount we *want* to save: $10,000

Have you heard of this mystical thing in business called “profit??” It’s a pretty crazy phenomenon we’re just hearing about! It means that you don’t just spend every dollar your business brings in, but that you can keep some of it! It escaped us for a few years, but we’ve decided to utilize its wonderful powers going forward and put a much heavier focus on it 😂. Alright, jokes aside, our goal is to have $10,000 every month we can put into our savings, investments, and not touch at all. We’ve NEVER been able to predictably save a sizable amount of money each month and we want that to change.

It’s probably worth mentioning that we *have* been saving and investing the past few years, just not in a super regimented fashion. You can read how we currently invest and save our money here.

The average monthly amount we want to give to causes: $3,000

It can be really hard to give money to charities and great causes when you can barely eek a profit out of your business. We’ve managed to donate every month this year because we’re finally prioritizing it, but we want to do much more. Part of this Journey to 330 is to bake charitable giving into our financial plan. We want to allocate 10% of our total monthly revenue to non-profit organizations, causes, and other acts of good that come onto our radar each month. The idea of having $3,000 every month that we can give away and help make a difference is something we’re really excited about!


Those five categories of money add up to $33,000. As a reminder, our goal is to hit $33,000 in monthly recurring revenue in 12 months (that would be by September 1, 2019). Will it happen? What are we doing to make it happen? Find out each month going forward by referring back to this post. We’ll add an updated section each month with how our launches are going, what we’re doing to reach this goal of 330 members, and how our feelings continue to evolve about this enough goal.

Shameless plug to ask you to join our Wandering Weekly email list if you want to have little reminders about our Journey to 330 as well as get our awesome content related to fitting business into your life, making more money with your creativity, and being more intentional with your choices.



The Starting Line and Getting 14.4% Past It (Everything Before September 1, 2018)

As of September 1, 2018:

Monthly Recurring Revenue (MRR): $4,783
Total Paying WAIM Members: 48

14.4% to goal

Monthly Profit and loss:

Total WAIM MRR: $4,783
Total WAIM Fees (Stripe/PayPal): $145
Total Expenses to Build WAIM: $16,500
Monthly Expenses in August: $7,460
TOTAL PROFIT: -$19,177 (eeeeek)

Quick hits of what we did to get this first group of paying members:

  • Shared everything it took to build Wandering Aimfully
  • Had an entirely new membership dashboard built
  • Did a pre-order launch of our memberships in May
  • Did the initial launch in August (20-27)

Ideally, we would’ve started this public journey at $0 MRR. Unfortunately, it takes a lot of time to put something like this Journey to 330 post together and we simply didn’t have the time while we were building our actual website and business. Every hour we had from March 1 – August 19 (2018) was spent bringing Wandering Aimfully to life. During that time we did a pre-order of our WAIM Membership and a first public launch.

In trying to keep this first update as succinct as possible (the irony is thick there), just know we spent five months planning, designing, building, working with developers, going through 400 of our past articles, riding a bunch of emotional roller coasters, creating our purchasing flow, and completing well over 2,000 tasks to bring this website and our membership offering to life. We also had a website dedicated to the behind the scenes of building WAIM, which was live from March 1 to August 19.

Under Construction Wandering Aimfully Website

Our first 15 paying customers: May 2018 Pre-Order

Before WAIM was finished being built, we knew we wanted to offer a pre-order for our memberships. We made this decision based on two things:

  • We teased to our email lists that we’d be offering a membership community and people said they were interested (so we wanted people to put money where their mouths were).
  • We wanted to fully test our somewhat complex purchasing flow using a new system we’d never had experience with (Restrict Content Pro [aff link]).

We opened up our pre-order for just one week, limited it to 30 buyers only, and sent three emails to a list of 400ish subscribers (this was a segment of our bigger list that had opted into daily-ish blog posts about how the build was going). Our three emails were fairly simple and explained the gist of the membership, the existing courses/workshops they’d get access to, and then a tease of what was coming in future months with WAIM.

Wandering Aimfully Pre-Order Page

There was only one hitch: We told our pre-order members they wouldn’t get full access to everything for at least a month (sell before you’re ready!)

While they’d receive access to our courses, this custom member dashboard we kept telling them about wouldn’t be fully coded for at least another month. Would people still pre-order if they couldn’t get the full experience right away? Well…

The WAIM Pre-Order brought in 15 buyers, netting us $1,483 in MRR

  • 488 people visited the pre-order sales page
  • 15 people pre-ordered (3% sales conversion – pretty epic!)
  • 14 people purchased the $100 per month option
  • 1 person purchased the $1,000 per year option (Hi Martha! 👋)
  • 11 people paid using Stripe
  • 4 people paid using PayPal

Wandering Aimfully Pre-Order Metrics

(You’ll notice the Airtable view of customers only shows 13 people and this is because two of our pre-order members canceled a few months in – sad panda. We’ll talk more about this in a moment.)

Our next 35 paying customers: August 20-27, 2018 Launch

With our website finally up and running it was time to do our first official launch! August 20 was the start date and we would leave the “cart” open for one week, again limiting the number of buyers to just 30 people. This launch was quite a bit different from our pre-order because it also coincided with the website going live and we sent sales emails to our entire email list.

Leading up to August 5, we created lots-o-content!

We decided early on that we’d write a behind the scenes journal sharing all of our processes, decisions, roadblocks, problems, and even share full unedited video meetings. From March 21 to August 5 we created and shared:

  • 49 blog posts (21,200 total website visitors)
  • 29 videos (just over 11,000 total views)
  • 61 Instagram posts (30ish stories)

Wandering Aimfully Lead Up Marketing

From August 5 to August 20 we warmed our audiences up to our first launch

Here’s what that looked like…

Caroline’s previous email list (Self-Made Society): On August 5 Caroline mentioned that WAIM was coming on August 20. This was sent to 5,502 subscribers and 1,514 of those subscribers opened the email (27.5% open rate).

My previous email list (JasonDoesStuff): On August 7 I mentioned to my email list that WAIM was launching on August 20. This was sent to 11,538 subscribers and 2,477 of those subscribers opened the email (21.5% open rate).

Our first combined newsletter (Wandering Weekly): On August 13 we sent our first combined email newsletter prepping the subscribers of our new website and membership on August 20. This was sent to 16,684 subscribers and 2,411 of those subscribers opened the email (14.5%* open rate).

*Something definitely went wrong with this email broadcast. We actually reached out to our email provider and they admitted something looked weird. Unfortunately, we had too many to-dos on our list to diagnose things and didn’t want to try to resend the email with fear of something else going wrong or happening with our email reputation.

We shared teasers and whatnot on social media: While our social media follower numbers are nothing to scoff at, it’s important to note we also don’t see social media as a huge driver of new traffic or sales. Even though I have 31,000+ followers on Twitter, the engagement of even the most exciting of tweets is VERY low. Caroline has 2,900+ followers on Twitter, but I think she’d echo my statements about engagement (and she mostly just pushes her Instagram posts through to Twitter). Speaking of, Caroline wins our household Instagram award with 16,000+ followers; I have just a touch over 3,000 followers; and Caroline runs our @wanderingaimfully account which has 900+ followers. Those numbers are just to give you an idea of the impressions we’re working with. Numbers aside, we posted a handful of tweets with teaser images, shared a few stories on Instagram, and just generally kept people tuned-in to the launch date of August 20. Caroline did work some pretty awesome grid-magic on IG (as you may have noticed in the “Lead Up Stuff” image above).

While keeping our audiences ready, we wrote our sales email sequence

This isn’t our first rodeo selling something over the course of a week. We knew we didn’t want to be writing and sending sales emails the night before (we’ve done that too many times and it’s stressssssful), so instead we whipped up a Google Doc and wrote all our sales emails in one spot.

Pro-tip: This is also a great way to get the subject line, preview line, links, etc organized ahead of time.

Wandering Aimfully Sales Email Google Doc and Drip Campaign

Then Caroline worked her wizardry in our email provider ( Drip [aff link]) to set up a “campaign,” which is just a string of emails with a simple sending schedule (shown above). Here is the timing of the sales emails along with the general topic discussed:

  1. Monday, August 20: New site is live! Memberships are OPEN! 😱
  2. Tuesday, August 21: Case studies and testimonials 👫👫
  3. Thursday, August 23: New resources to be added in September for members 🤩
  4. Saturday, August 25: How can WAIM help you? Reply! 🤔
  5. Monday, August 27: Memberships are closing tonight 😬
  6. (We didn’t end up needing to send this email, as you’ll read!) Monday, August 27 (evening): Last call!!! 😳

These emails were sent to our newly combined (as of August 13) Wandering Weekly email list minus the last email in the campaign because we hit our goal and didn’t need to send a “Last call” email. Who turns off one extra sales email during a launch knowing it would probably bring in more sales? We do. That’s who.

In the image below you can see the open rates improved greatly using this email campaign in Drip, as opposed to a normal broadcast email (very odd). And a couple email stats for you:

  • Starting # of subscribers: 16,329
  • Total unsubscribes during launch: 520*
  • Average open rate: 20.8% (3,396)
  • Sales conversation rate (email opens to WAIM buyers): 1.4%

*Truthfully, we’re happy to see people unsubscribe as we know our content and membership isn’t the right fit for them.

Wandering Aimfully August 2018 Sales Campaign Emails

Wait, 35 new customers, I thought you said 30 was the limit?? Let’s dive into the data of our first launch…

35 new customers, what happened to 30? Ahhh, you are astute! So, a couple things happened which led us to end up at 5 buyers over the 30 number we set:

  1. We had two pre-order buyers cancel during the launch, so we figured we’d just fill their spots and let two new people come in
  2. We had one new customer cancel the day after they purchased
  3. The counter that tracks our amount of member spots left is completely manual and we may have forgotten to update it when a buyer came in overnight (whoops!)

With that out of the way, let’s look at when people bought during the launch:

  • Monday (Aug 20): 8 new members
  • Tuesday (Aug 21): 2 new members (but 1 canceled)
  • Wednesday (Aug 22): 3 new members
  • Thursday (Aug 23): 5 new members
  • Friday (Aug 24): 3 new members
  • Saturday (Aug 25): 5 new members
  • Sunday (Aug 26): 0 new members (crazy, huh?)
  • Monday (Aug 27): 10 new members

We offer credit card or PayPal as a buying option, so here’s the split on that:

  • 60% bought using credit card (21 people)
  • 40% bought using PayPal* (14 people)

*PayPal actually wasn’t working for the first four days due to two technical issues we missed. We finally got them fixed but have no idea if we missed out on folks who wanted to purchase via PayPal. Oh well.

And finally, the traffic to during the launch:

  • Total new website visitors: 9,782
  • Traffic from search: 64%
  • Traffic from direct (email): 21%
  • Traffic from social: 10%
  • Membership page visitors: 992
  • Membership page sales conversion: 3%

Wandering Aimfully Launch Week Website Analytics

To recap: As of September 1, 2018, we’re at $4,783 MRR (or 14.4% of our goal)

There’s no doubt in our minds that the initial launch is the most exciting time for people. It’ll be very interesting to see if we can keep up our pace of 30 new members each month going forward.

And now, the best and worst parts of our first official launch:

The BEST part of our first launch?

We can’t stress enough how excited we were to get Wandering Aimfully launched, but more importantly, to have a new group of amazingly talented and creative people in our community.

Wandering Aimfully Slack Member

The WORST part of our first launch?

It’s hard to categorize anything as the “worst” part when things go pretty much to plan. If we had to mention something here, it would probably be how much stuff we have to do manually behind the scenes for a new customer that buys via PayPal. We won’t bore you with all the details, just know that each PayPal customer requires a bunch of manual processes that we’d love to automate in the future, but had to launch without (even though we tried to automate them months prior).

One last thing: We’ll be using Baremetrics to publicly track and share our progress

We’ll be using Baremetrics to track our member growth progress and revenue and you can actually view our public MRR dashboard here. Baremetrics is super neat because it helps you keep track of customers, revenue, churn, and lots of other powerful recurring revenue stuff.

Wandering Aimfully Baremetrics Dashboard

A big shout out to Josh and his team for getting us hooked up on Baremetrics and making it really easy to update our Airtable with actual monthly revenue.


That’ll do it for this first update! Now, it’s time to get to work on creating new stuff for our WAIM Members and executing our plans for the lead-up to our October launch.



UPDATE #2: OCTOBER 10, 2018

After Our Second Launch We’re 19.2% Toward Our “Enough” Goal (Sept 2 – Oct 10, 2018)

As of October 10, 2018:

Monthly Recurring Revenue (MRR): $6,350
Total Paying WAIM Members: 62

19.2% to goal

Monthly Profit and loss:

Total WAIM MRR: $6,350
Total WAIM Fees (Stripe/PayPal): $160
Monthly Expenses in September: -$3,496

Quick hits of what we did to get this first group of paying members:

This is our second update on our Journey to 330 and man-oh-man do I have ALLLL the thoughts to share. If you are unclear of our “growth strategy” with selling our Wandering Aimfully Memberships, the goal is to open the doors every month and only allow up to 30 new paying members. One thing that you’ll notice between the first and second update is that our assumption about our expenses was correct. We can’t live off the $2,854 in profit we made this month*, but it’s great to know that our business is not making more money than it spends (after just two months!)

*If you’re wondering how we’re keeping the lights on since we aren’t making the profit needed to cover our total living expenses, we have ongoing payments from our previous BuyOurFuture project as well as revenue from a few other online courses and software products. Truth be told, these Fall months will be tight financially and we hope we don’t have to dip into our savings!

Looking at the month of September, we had a hunch that the luster would wear off during our second launch and I’ll talk more about that in a moment. But, one really big thing happened between the first launch and our second launch and that is that life took a big steaming 💩 on our faces…

Caroline got shingles and it royally sucked!

You know that phrase everyone (including us) like to throw around: “Plan ahead because life will shit on your face.” Well, it happened to us in a big way in September. My lovely and very healthy wife mentioned she had some tightness in her neck at the beginning of September and a few days later we found ourselves in an Urgent Care doctor’s office hearing that Caroline was diagnosed with shingles. Oof.

Caroline got shingled.

I’ll save you all the intimate details of how bad shingles can suck, but here’s the painful timeline of how it went down:

  • Week One: Caroline had shooting pains in her neck and could barely get out of bed
  • Week Two: Caroline still had a lot of pain in her neck and generally felt awful
  • Week Three: The pain in her neck lessened, but the itching (deep nerve itching) started
  • Week Four: The itching continued and some pain came back in her shoulder/neck
  • Week Five: Almost out of the woods, but we saw another doctor and got additional meds

Those five weeks happened between the first launch and second launch of Wandering Aimfully and unfortunately, it left us a woman down in the work department. While I tried to carry my weight and tow the line of everything we had going on (and keeping my other business ventures afloat) I spent the majority of my time trying to give Caroline any ounce of comfort possible. It was difficult not being able to work like we normally do, but truthfully, it was an emotional few weeks for me and an insanely few painful/emotional weeks for Caroline.

I don’t want this entire update to be about our run-in with shingles, but it’s worth noting that you DO have to prepare for these life hiccups to happen. You can be mad about it, you can be frustrated about it, but you can’t just fast forward life so you hunker down and deal with it the best you can.

I’m happy to report that Caroline is feeling 1000% better than she was during week one of shingles, but she still has some lingering issues (which we’ve come to discover are normal).

We launched our podcast/YouTube show, aptly titled Wandering Aimfully: The Show!

Earlier on in the summer, we made the decision to create a podcast and YouTube show where we’d talk about areas of life where we’ve wandered aimfully and share our experiences, stories, and lessons learned. Originally we were going to launch the show at the time of launching the website, but Caroline had a good idea to push the launch date of the show back a month so we’d have something fun to announce after the luster of our new website announcement wore off (good idea Carol!)

I’ve had a few podcasts over the years and one of the most important things I’ve done for my sanity in running them is to get AHEAD of the publishing schedule. We still had a ton of work on our plate during the summer months, but we carved out time to record five initial episodes of Wandering Aimfully: The Show. This was a clutch move because we couldn’t record a single thing in September and it was nice to know we had five weeks of episodes already recorded and ready to be edited.

Wandering Aimfully: The Show Recording Setup

I don’t want to spend too much time on the production of our show, but just know that:

  • Setup and teardown of our recording “set” takes about 1 hour (3 DSLR cameras, 2 mics, lots of cords)
  • Recording an episode takes about 1.5 hours (not including any prep or research)
  • Organizing and importing 80 GBs of footage (per episode!) takes about 1 hour
  • Editing and color correcting each episode takes about 15-20 hours
  • Exporting, uploading, creating an episode post, writing copy, etc takes about 2 hours
  • Each episode takes on average 25 total hours to produce 😱

I could, and may, write an entire article devoted to our plan and strategy with our podcast/YouTube show, but the short of it is we want to create a show that we’d enjoy watching. Our assumption is that we’ll deepen the relationship with our existing audience through the show, having them (you!) feel a connection to us that you can’t get through the written word. Could we see some external growth with our show? Maybe. But that’s kind of out of our control, so we’re not focused on that.

Wandering Aimfully: The Show on iTunes

As of writing this second launch update, we’ve released five episodes and the total views/downloads are just around the 3,000 mark. To some people, that may be great! To others, that may not seem worth the 125+ hours we’ve put in. To us, we’re committing to the show because we enjoy it and we want to see how it goes for a few months.

EDITOR’S NOTE: After reading back through this section of the update I posted a note in the Wandering Aimfully Slack channel about how much work was going into our show and not being sure if it was actually going to pay off (just some straight-up #realtalk). I heard back from many of our members that they loved the show and it was doing exactly what we intended it to do. Plus, a few newer members said the podcast pushed them over the edge to join WAIM. So… hurray testing assumptions!

During our second launch we had 18 new paying members

As you’ve read and understood, our goal is to get 30 new paying members each time we open the WAIM Membership doors. We are not naive and we understood that there would be a natural drop-off in membership with our existing audience.

New Wandering Aimfully members in October 2018

As our October launch approached we were trying to figure out the best way to sell our memberships, but not oversell it to the folks who went through our full 7-day sales sequence just a few weeks prior. Here’s what we ended up doing for our second launch.

Launch Group #1 – New subscribers who didn’t get the 7-day sales sequence in August (408 subscribers)

This group was made up of new email subscribers who went through our 5-day welcome email sequence and did not get our first launch sales sequence.

We dropped these folks directly in the same 7-day sales sequence we used before:

  • It was the same 5 emails we sent to our full email list in August
  • We updated the copy in 2 of the emails (to remove “we’ve just launched”)
  • The 5 emails saw an average open rate of 32.4%
  • The emails had a total of 25 clicks to the WAIM sales page (yep, only 25)
  • 29 people unsubscribed ¯\_(ツ)_/¯

And the most important stat of all? 8* people purchased!

*Unfortunately, we don’t have concrete data to say that our email sales sequence was the sole reason these folks purchased, but they were all in that group of 408 subscribers, so we’ll take it! Also, we’re going to try to track conversions from the 7-day sales sequence better during our next launch (always room to improve).

Launch Group #2 – Existing subscribers (15,931 subscribers)

I’m gonna be brutally honest and just come out and say it: I’m nervous that our email provider is having email sending issues. I’ve heard from another customer of Drip that they’ve seen a huge drop in email open rates, but it’s crazy to me that we went from an average of 20-25% open rates down to 10-15% since switching to a combined newsletter with a new from email address. That’s probably a topic for an entire other discussion, but we can’t do much about it now, so… let’s move on.

We sent our existing subscriber group three emails during our second launch:

Email #1: A normal newsletter about taking risks which aligned with our podcast episode that had a callout that memberships were open at the top (14% open rate).

Email #2: A dedicated sales email three days later focusing on wins our WAIM members shared with us with a bit more of a pitch to join (13.5% open rate).

Email #3: Another normal newsletter on the last day of the launch about confidence with a reminder callout that memberships were closing (11% open rate… but this data is written one day after sending that email).

It’s safe for us to assume that 8 of our new customers came from these emails.

So, where did the other 2 customers come from? Well… They found us completely out of the blue and joined in the last few moments! No joke. I emailed with both new customers who weren’t on our list and they said they hadn’t heard of us before joining but felt a real connection to us and WAIM and decided to take the leap. Pretty cool!

New WAIM Member

How does it feel to not hit our goal of 30 new paying members (and thus miss our revenue goal)?

Honestly? And most people would probably try to hide behind fake optimism… It sucks. It sucks to put something out into the world that you truly believe can make a difference for folks, but to not see the conversions happen.

BUT… We knew it wasn’t going to be easy to get 30 new paying members each month and we also knew that September was a really tough month for us.

If we take a step back we can see that we have 18 new (awesome) members who believe in us. We can see that we didn’t do much marketing or promotion at all, with exception to launching our show (which, as stated, is more of an audience deepening decision, not a widening one). And you know what’s better than a big fat 0? 18! There is a tinge of discomfort that we missed our 30 mark, but, we’re grateful to have new members AND our existing group who continue to stay active members.

To recap: As of October 10, 2018, we’re at $6,350 MRR (or 19.2% of our goal)

We have a second launch under our belt after having a pretty damn rough month personally. We still ended up with new members and even though we didn’t hit our goal, we were able to test some assumptions about the groups on our email list we could sell to.

Let’s finish up with the BEST and WORST…

The BEST part of our second launch?

We got some new members! 18 is way better than 0. The quality of the members of the second group seems to be on par with the first group (which is rad!) We were also really stoked that brand new subscribers converted to paying members, which bodes well for the future of our email marketing plans.

Wandering Aimfully Membership Growth

The WORST parts of our second launch?

There are two things I want to share and you probably guessed the first one: Poor Caroline had to deal with shingles the entire month. It. Was. Awful. But, we made it through and she’s feeling so much better. Could’ve been worse!

The second worst part I wanted to share is that 5 customers canceled their memberships. Personally, I have some soul-searching to do on how I deal with people canceling, especially after only being a member for one month. I get it, people will cancel, it’s the name of the membership game… but that doesn’t mean it doesn’t suck and it doesn’t make me feel emotions (even though most of the time I have the emotions of a robot).

WAIM Member Cancelations

The silver lining to having people cancel is that we get to learn why they canceled. We can find ways to improve or to make our membership better. We absolutely believe WAIM is worth the $100 per month, but we also know we don’t have the best onboarding process for our new members. Hoping to spend time on this in the next few weeks!


Hope you enjoyed our second update on our Journey to 330! It’s as much a reminder to us as it is to you that reaching your goals isn’t going to happen overnight. It’s also not going to happen just because you hope and dream it will. You have to put in the work and you have to prepare for things to go wrong now and again.


UPDATE #3: NOVEMBER 15, 2018

After Our Third Launch We’re 18.5% Toward Our “Enough” Goal (Oct 11 – Nov 15, 2018)

As of November 15, 2018:

Monthly Recurring Revenue (MRR): $6,133
Total Paying WAIM Members: 62

18.5% to goal

Monthly Profit and loss:

Total WAIM MRR: $6,133
Total WAIM Fees (Stripe/PayPal): $128
Monthly Expenses in September: -$3,590

Quick hits of what we did this month:


Holy moly, where do we begin this month? Well… Let’s just go ahead and rip the band-aid off and jump right into the biggest emotional topic.

Our MRR went DOWN after our third launch, and, truthfully, that sucked.

This is a very weird sentence to type, but we’re kind of glad our MRR went down. Wait, do we hate making money? Are we gluttons for punishment? Why the heck would we be happy that our MRR went down??

Here’s the deal, and it’s my belief it’s going to make total sense after you read this:

We humans love drama. We don’t like to just watch other people succeed without challenges.

We like to see some tension. We need relatability. We need something to go wrong so we can see how the hero(es) overcome the adversity.

Now, if I’m being honest, I’d rather that drama didn’t involve how much revenue we generate, but it is what it is. The fact of the matter is that between October 10 (the end of our second launch) and November 12 (the end of our third launch) we had more people cancel than we had signup. OOF. Not great.

I’m the one who more closely watches our WAIM Memberships and it was a punch to the gut every time a cancelation email came through. All-in, we had 12 people cancel their WAIM Memberships which increased our User Churn to 16.9% (industry average is 11%).

WAIM November Churn

While it sucks that people canceled the memberships, it’s a great opportunity for us to learn what we need to improve upon.

The wise and experienced co-founder of Basecamp, Jason Fried, once said that you learn the MOST about your product right when a customer signs up or right when they cancel. When a new customer joins, ask them why and find out if there are recurring things that are attracting and converting people (and do more of that!). When a customer cancels, asks them why and try to fix that problem asap. So, that’s exactly what I’ve been doing with every WAIM Member who’s canceled.

I would have expected members who canceled to say things like: You guys aren’t as helpful as I thought or Your products aren’t what I expected or I just expected something completely different. But, we didn’t hear any of that. In fact, we’re seeing people cancel their WAIM Memberships because we have TOO MANY products. We’re hearing that folks believe in the value of WAIM, but they were overwhelmed by all the products available and not sure where to begin. And while that might seem like a good problem to have, it’s still a problem that needs fixing because it is causing people to leave.

Can I just pause for a moment and be brutally real with you… Emailing people and asking them why they canceled is humbling. It’s not fun. But, if you’re trying to build something that can last and that can make an actual impact for your customers, you have to push through the uncomfortable moments. Every time I hit send asking people why they canceled it feels crappy. But it’s necessary, and I’ll continue to do it.

Is it possible that we can fix this problem of overwhelm and hopefully reduce our member churn in the process?

I’m going to save the answer to this question until the final part of this month’s Journey to 330 update. For now, let me take a break from talking about everything that went wrong and share some stuff that went RIGHT!

We hosted three workshops in the past month and people loved them!

One of the things Caroline and I enjoy most is teaching live workshops. Caroline is amazing at coming up with frameworks and processes that we can use ourselves and pass on to others. The live video element takes me back to my IWearYourShirt days where I hosted a 1-hour live video show daily for nearly 5 years straight (yeah, you read that right!) There’s something about the energy of speaking to people live and getting immediate feedback that lights us both up.

WAIM Workshops

Workshop #1: Selling Without Feeling Sleazy

This workshop was initially supposed to happen during our second launch but with Caroline still not feeling great we had to postpone it a bit. Instead, we held the workshop on October 18 and had 232 people register. Of those 232 people, 139 showed up to the event which is a whopping 61.5% attendance rate (that’s RAD!)

Selling Without Feeling Sleazy Workshop Analytics

We didn’t have anything to sell on the workshop, so it was just 100% value-driven. That being said, we did have two people email us after the workshop who thanked us and said they would be joining WAIM because the workshop was so great (and they both stuck to their word and signed up during our November launch – wahoo!).

Workshop #2: SEO & Google Analytics (Members Only)

For a while, we’ve wanted to have WAIM Member co-hosted workshops as there are some really talented and smart people in our community. One member, in particular, has been an all-star since joining what WAIM was previously known as: BuyMyFuture.

That member is Brendan Hufford and he’s been an incredibly valuable community member. Brendan lives, eats, and breaths SEO, so whenever someone has a question in our community Slack channel, Brendan is all over it (or if I beat him to read it, I’ll tag him and then he’ll reply).

Through a few random DM convos, Brendan and I decided it was time to do a basic SEO workshop as well as share a really nice Custom Google Analytics Dashboard that’s perfect for content creators.

WAIM Members-Only SEO Workshop

This workshop was for a much smaller audience, just our paying WAIM Members, but I was still stoked we had 83 people register (20% of our total community) and a 55% show-up rate. Even better than that, the comments at the end of the live workshop and afterward were incredibly positive (it helps that Brendan was a teacher in his former life, so he’s great at hosting and keeping people engaged!)

WAIMs are happy!

Workshop #3: Our “Customer Journey Marketing Plan” Exercise

Truth be told, we didn’t plan to do this workshop when we started our third launch of WAIM Memberships. However, because we missed doing a workshop during October’s launch, we decided to squeeze this one in and do it during the final day of our 1-week launch window.

We had 193 people register for the workshop and another great show-up rate (56.5%). I believe we had people attend from 25 countries around the world for this one, which is really neat!

WAIM Marketing Workshop Attendees

The big experiment for this workshop was to have a sales pitch for WAIM Memberships at the end. The workshop itself was approximately 45 minutes of teaching and 15 minutes of selling. We unveiled a new plan in the works, which again I’ll get to in a moment. Here’s what the sales slides looked like:

WAIM Workshop Sales Pitch

We’re not new to selling on live workshops, especially me. That’s actually something I got really comfortable doing 2013-2015. You can imagine my surprise when we had… drumroll… zero sales. Not a single person bought during the workshop and only one person bought when we sent out a follow-up reminder email that the doors were closing for WAIM Memberships.

Which, leads us to two final updates this month…

We believe that WAIM Memberships are a bit too general and don’t solve a specific enough problem for prospective customers.

This is part of the discussion about members canceling due to feeling overwhelmed. While we can solve many problems with the 30+ products we provide in WAIM, it’s too much to choose from and feels like we’re not addressing a bigger problem we can solve for people.

As we’ve watched our membership join rates decline from August (first launch), October (second launch), to November (third launch), it’s apparent to us that something is missing the mark. That something is what we’re going to hunker down and focus on next.

With only 7 new members joining in November (and 12 people canceling in October), we have to make a change.

Sometimes you don’t have a crystal clear change to make in your business when things aren’t going exactly as you want them to go. It would be an entirely different story if people were canceling our membership and saying, The courses are crap, The other members aren’t around, and You guys aren’t who I thought you were. Thankfully, NO ONE is saying those things (at least not to our faces or email inboxes – haha). But if people were saying those things, we’d have an idea of exactly what to fix. Instead, we’re making a best guess based on what our gut is telling us.

We’re going to create a new 6-month program that’s laser-focused on solving a big problem for a specific type of person and focus the entire membership around that core program.

You may have caught a glimpse of this in the sales slides I included a GIF of a few paragraphs ago, but this is where we’re taking a big leap of faith. We’ve known from the beginning that what you get with WAIM is a bit too generic. We’ve always loved that our resources can help people at different parts of their business journey (not started, beginning, intermediate) and that what we teach can apply to different types of businesses (products and service-based business) BUT just because your product can do something doesn’t mean that’s how you should market it. Trying to solve everyone’s problems at once makes for some pretty diluted marketing. Our selling proposition doesn’t speak enough to a specific problem that people have or can clearly articulate. That’s a recipe for disaster when it comes to selling anything. I believe we got as far as we did with this generic approach only because we’ve worked so hard at building trust over the past few years.

WAIM 6-Month Program Preview

Going forward, we want to focus on this singular pain-point:

Wandering Aimfully is the membership community that teaches you how to turn your creative skills into a profitable digital product business, without sacrificing your lifestyle in the process.

To accomplish that, we’re creating a 6-month program that’s the MAIN focus when people join WAIM. They can get everything else (all 30+ previous products) but we’ll position that stuff as “in the vault.” While we’d love to rest on our laurels and believe all our previously created content is good enough to solve problems for people, we know we can do better. We know we’ve learned a ton and that we want to give a more concise and updated plan of action for our members to follow.

Soooooo, what the heck are the next steps to accomplish building this 6-month program?

  1. We’re going to plan out the curriculum for this 6-month program
  2. We’re going to create the content for this program (with assistance from our existing members) and build it into our membership dashboard
  3. We’re going to rewrite parts of our website copy and reposition WAIM on our sales page
  4. We’re going to try to do all of that by January… eek.

One of the core tenants of this 6-month program is giving you a framework to follow that helps you avoid burnout. Unfortunately, we don’t have the luxury (read: cash flow) to take the next 6 months to build this program. Instead, we’re going to have to reduce any other tasks or commitments and hunker down to build something great, free from other distractions.

Should be run, right? Well, we’re nothing if not up for putting in the work it takes to succeed. We will absolutely do our best to stay balanced and not overwork ourselves. (Definitely no intention of going shingles Round 2 in this house!)

To recap: As of November 15, 2018, we’re at $6,133 MRR (or 18.5% of our goal)

It would be easy to sum up the past month as a “bad” month due to a smaller launch and higher rate of member cancelations, but it wasn’t bad. Caroline’s health improved. Our existing members are happy, excited, and getting value from what we’re doing. We are making a difference for people, providing value to them, and enjoying most of the process.

The BEST part of our third launch?

We realized that we need even more clarity and focus around what WAIM can provide its members, what specific problem it can solve, and who it would be a great fit for.

And of course, the fact that we did get some new paying members was great!

New WAIM Customers in November 2018

The WORST part of our third launch?

Watching 12 people cancel their memberships between the second and third launch. As helpful as learning from the cancelations is (and it may end up being the catalyst that helped propel us toward our Journey to 330 goal faster), it was a punch to the nether-regions this month.


Phew, what an update! We really hope you enjoy these. It’s the exact type of content we love, especially when things aren’t going perfectly so you can see how people overcome adversity (it just kind of sucks to be the ones having the adversity!)


UPDATE #4: JANUARY 30, 2019

After Our Fourth Launch We’re 21% Toward Our “Enough” Goal (Nov 15 – January 30, 2019)

As of January 30, 2019:

Monthly Recurring Revenue (MRR): $6,917
Total Paying WAIM Members: 73

21% to goal

Monthly Profit and loss:

Total WAIM MRR: $6,917
Total WAIM Fees (Stripe/PayPal): $342
Monthly Expenses in September: -$2,963

Quick hits of what we did this month:

  • Went through the busy holiday season!
  • Planned and created our new program Build Without Burnout Academy
  • Hosted a Members-Only Quarterly video call
  • Created and shared “Pretend People Problem” videos/articles (3 of ‘em)
  • Continued recording and promoting our weekly podcast/show episodes (11 eps)
  • Edited and released our first travel video (Tahiti!)
  • Put together an in-depth guide on transitioning from Clients to Products
  • Hosted a video workshop to help folks transition from Clients to Products
  • 20 posts on WAIM Instagram
  • Completely redesigned and rewrote our sales page 😱
  • Flew back to Florida for Christmas with our families
  • Gained 22 new WAIM members with our last monthly launch (for now)
  • Jason had jury duty for a day (WOOF)
  • And poor Caroline has been dealing with terrible anxiety


There is a tonnnnn to get caught up on but we’ll start with the unfortunate part of this update…

Caroline has been struggling with some really bad anxiety the past few weeks.

The holiday season was a blur and the new year started off on a great foot for her, but then it all came to a screeching halt in early January.

Instead of hiding her anxiety, we shared what Caroline was going through with our WAIM Members and on social media and the response was amazing. We can’t thank you enough if you sent kind words and thoughts our way.

View this post on Instagram

Let's get real.⁣ ⁣ This morning we made the tough decision to push back the start date of a new program we've been working on for months. ⁣ ⁣ The truth of the matter is Caroline is dealing with some rough anxiety and it's not worth pushing each day and risking her long-term health.‏⁣ ⁣ _ We sent an email to our 400+ existing WAIM members making the announcement that we'd be pushing back the start date. Writing and sending that email sucked. Even worse? We are finishing up another launch of our membership right now and feel like we're letting new members down.⁣ ⁣ But… The replies to our announcement email have left us floored.⁣ ⁣ Caroline's current bout with anxiety has made us realize how many people deal with anxiety on a day-to-day basis. So many people are replying that they or a loved one are affected by it.⁣ ⁣ A big part of me didn't want to make this public. We thought about keeping it quiet & working with our members behind the scenes. However, this shit is real. Running your own business can lead to some rough patches & it's important to share that almost ALL of us go through it.⁣ ⁣ There's no way for me to understand how awful Caroline feels, I only know how helpless I feel watching her be in pain. All I want to do is take the pain away. All I want to do is absorb what she's dealing with, even for a few hours so she can feel better.⁣ ⁣ Our health should be our #1 priority. ⁣ ⁣ We can't run a business if we can't get out of bed. ⁣ We can't create things if we can't function.⁣ We can't show up for other people if we don't take care of ourselves.⁣ ⁣ It's easy to pretend like nothing is wrong and try to push through it.⁣ ⁣ I know that admitting this publicly will dissuade people from joining our membership. I know it will hurt our sales goals. It's just the nature of how things work. I'd rather people also know how honest and transparent we are. Our lives are not a beautiful highlight reel.⁣ ⁣ While we believe in working hard we also know that there's a negative side to spending all these hours plugged in, scrolling, typing, and being constantly connected. ⁣ ⁣ Continued in the comments…

A post shared by Jason Zook (@jasondoesstuff) on

While we were still able to do our January WAIM membership launch, we decided that we would push back the start date of our new program Build Without Burnout Academy and remove every work item from Caroline’s plate. We’re hoping a month of rest and easing back into just a little bit of work each day is what Caroline needs. She’s also trying everything under the sun to fight her anxiety (meditation, CBD, relaxing teas, extra sleep, therapy, and anything else folks have sent us or she’s read about).

With shingles hitting Caroline just a few months ago we are certainly trying to listen to the universe telling her that something isn’t quite right.

We’re doing our best to create space and avoid any stressors at the moment.

Let’s gracefully transition to discussing our 6-month program Build Without Burnout Academy – the newest addition to our WAIM Membership.

We teased this in the previous update, a 6-month program around a more specific problem and target audience.

We’ve had many conversations about WHO our membership is for and WHAT problem we’re specifically solving based on our experience. We knew the initial positioning of our membership was vague but we simply had to start somewhere (and hey, it did work and attracted over 60 paying customers!)

That being said, one of the things we always talk about when people ask us for advice is to niche down and get as focused as you can. We took our own advice and had multiple conversations about what that meant for us and WAIM.

What we came up with was honing in on the exact transition we made in our businesses: Going from working with clients to selling digital products.

We have A LOT to say on this topic. We also have tons of tangible and practical advice we can give because we have firsthand experience and lessons learned (always a good sign!)

One of the first things we did was to rewrite the mission statement for our WAIM Membership…

Previous version: The essential membership community for independent creatives who want to earn more so they can live more.

New version: The membership community that helps client-based business owners transition into selling digital products—without burning out in the process.

I mean, yeah, pretty damn clear that we were talking to an extremely broad group of people with our previous version.

With this renewed focus of WHO our membership was for, we knew we hadn’t created a product within the membership that spoke directly to that audience and could help them (the WHAT). This is where our Build Without Burnout Academy product comes in!

Build Without Burnout Academy

We had many conversations and planning sessions about Build Without Burnout Academy. There were a few key components it had to have:

  1. It would be a guided weekly program that took 6 months
  2. We wouldn’t focus on some 6-figure dream outcome
  3. The content had to be bite-sized and actionable
  4. We wanted to pull in our best advice from other workshops/courses
  5. There would be monthly calls to bring program participants together
  6. There had to be an element of fun!

But the main component was that we’d have a brand new program to add to the WAIM Membership that would hopefully speak more directly to our target customer (and add value to the membership!)

👍 The GOOD news about Build Without Burnout Academy

We looooved how it all came together. Caroline did a wonderful job branding the experience, from the program curriculum, slide design, the experience within Teachery our members will go through, and the amazingly fun game board game element that accompanies the educational content.

👎 The BAD news…

We wanted to kick things off January 29 and have all our existing WAIM Members and new members from our January launch start together on their 6-month journey. With Caroline getting hit with anxiety we had to make the tough call to push the start date back to March 4. It wasn’t that we needed one more week to finish things, it’s that we care more about Caroline feeling normal so she can give her whole self to our members (and you know, feel normal!)

If we need to push the start date back again, we’ll cross that bridge when we get there. We’re taking it day by day and our members have been amazing about it.

Our 4th WAIM Membership launch brought in 22 new WAIM Members (from January 21-28)

Originally, our plan was to do a launch in December, but we decided to nix it due to the workload we had for Build Without Burnout Academy creation and our holiday travel schedule.

The January launch was the first one to our full email list since October. We felt comfortable it was enough time removed, plus, with the new mission statement and focus on Build Without Burnout Academy there was reason to share it with our full group of email subscribers.

WAIM January growth and churn

As you can see we’re still dealing with churn and had 15 members cancel between our last launch (November 15) and the end of our January launch.

We’re not assuming churn is going to disappear but we’re hopeful that our new 6-month guided program helps our members see this is a commitment for longer than they may have previously. That’s the hypothesis we’re going to test.

Interesting tidbit #1: We’ve had 102 total people join our membership (73 are active and 29 have canceled)

It’s awesome that we’ve had 100+ people sign up! It’s not so awesome that nearly 30% of them have canceled. Then again, even with industry standard churn being 7-15%, maybe 30% isn’t so bad given that our membership doors have been open for nine months (including our pre-sale in May 2018)?

Interesting tidbit #2: I (Jason) came to the realization that I’ve directly communicated with every single one of our 40 most recent members before they joined

This is incredibly interesting to us because it shows that the personal touch and direct communication goes a long way in making the sale.

This was also a very interesting realization as it showed us that we may have been using the wrong sales tactics the past few months. We’ve been applying our sales knowledge from digital product launches and we’re not selling a digital product anymore, we’re selling a monthly membership.

It’s clear to us that there’s a lot more trust needed for someone to make the purchase with a membership.

I shared a few tweets when this thought occurred to me (copying + pasting our online course sales to our membership sales process) and Amy Hoy jumped in to back me up:

Tweets with Amy Hoy

So…. How do we move forward with our sales process?

We’re going to create a “Test Drive the WAIM Membership” experience and move away from the monthly launch model.

Realizing that I’ve had some sort of direct interaction with our last 40 customers, and I didn’t hate doing it (important!), is a clear indicator that we should try a more hands-on sales approach. If I’m already emailing with folks during our monthly launches, why not just remove the work that goes into the monthly launch model and put it into something that’s more personalized and possibly takes the same amount of effort on my part (but makes the customer feel better)?

Step 1 in creating our WAIM Test Drive: Build a simple experience that walks potential customers through the highlight reel of our membership

Quite simply I’m going to create an online course that uses the lessons to preview different aspects of the WAIM Membership. Each lesson will have a short video and we’re going to highlight these items as “lessons”:

  • Who we are and how we’re different
  • Build Without Burnout Academy
  • The Slack community (along with some quotes/examples)
  • The Vault (our 30+ additional courses and workshops)
  • Included Teachery membership
  • Ongoing direct access to us

Wandering Aimfully Membership Test Drive

The final “lesson” in the test drive experience will be a sales pitch to join. Essentially, our membership doors will be open ongoing, but you won’t know that unless you take the test drive AND you make it through a few lessons (read: you show interest and go through the content!)

One note about the sales pitch lesson: There’s no sense of urgency or countdown timer since the test drive is simply just open all the time. My thought is to be 100% honest about that and point it out. Hopefully that directness will be a replacement for the missing timer or BUY NOW OR ELSE copy. We’ll see.

Step 2 in creating the WAIM Test Drive: Replace the section on our homepage with a preview of the test drive

Seems pretty simple, yeah? My goal is to keep the test drive process as frictionless as possible but make sure someone has to enter their email in some way to get access to the test drive content (hence the entire point of this, having direct communication).

Step 3 of the test drive: I will email each person who signs up personally. Yep. Every single one. Not through an email automation sequence.

This doesn’t scare me. It’s also not something I plan on doing long-term. I’m looking at it as an experiment and if it’s too many people and none are converting, I’ll stop.

However, we want to see if the test drive experience and the personal email outreach helps us convert new members. Again, I’ve basically been doing this during our monthly launches already, so instead of cramming all my effort into one week per month, it’s spreading that workload out based on the schedule of people who sign up and show some interest.

Our goal is to get the WAIM Test Drive up and running in the next few weeks. Even if Caroline isn’t feeling up to recording any video, I can have some fun with that and record solo. As with everything, just get started even if it’s imperfectly.

Note: I’m also going to be taking a social media detox for the month of February which will immediately free up the extra time that will go into creating the Test Drive and doing direct outreach throughout the month.

To recap: As of January 30, 2019, we’re at $6,917 MRR (or 21% of our goal)

Like anyone else, we’re doing our best to keep things moving along. The most important thing for us is to have Caroline recover and get back to feeling normal.

I’m going to skip the BEST and WORST part of the recap because this update is already reaaaaally long and in-depth. Plus, instead of thinking about what we don’t have yet in regards to our goal, let’s zoom the lens out and see what we do have…

Wandering Aimfully Membership Growth May 2018 to January 2019

We’re super appreciative that you take the time to read these updates and hope they help you on your journey to your own version of “enough.”

Have anything you wish we’d talk about? Want to give us feedback? Shoot us an email and let us know.



Here’s What We Plan To Accomplish Before March 14, 2019

Since we’re moving away from the monthly launch model and we want to gather some good data from our WAIM Test Drive experiment, the next update will be in mid-March.

Here’s what we’ll be working until the next update:

As a reminder, we’ll be sending updates about our Journey to 330 to our Wandering Weekly email list. If you want to get notified first when we have an update, hop aboard and subscribe now.



The Tools And Services We Use To Make Wandering Aimfully Tick

Note: Some of the services below have our affiliate links in which we make a tiny commission if you sign up.

Flywheel – We’re huge fans of Flywheel’s WordPress hosting! I joined them really early on with my previous JasonDoesStuff site and have loved every minute of paying them money. For just $15/month you get an intuitive dashboard, free SSL, fantastic customer service, and included hands-on migration from your existing WP host.

Restrict Content Pro (RCP) – We were completely new to RCP when we started building WAIM but we heard great things about it. RCP has lived up to the hype and is incredibly powerful if you’re trying to run a membership community using a WordPress website. The features are great, the help documentation is solid, and customer service has also been top notch.

Drip – Our current email provider of choice is Drip. We love all the fancy stuff you can do with automations, workflows, customer tagging, and more. Drip may be more than you need for email marketing so be sure to read our comparison article on MailChimp vs ConvertKit vs Drip.

Wistia – While we use YouTube for most of our video content, we also pay for Wistia every month. Wistia is perfect for videos that don’t need to be searchable or videos we want to share with our WAIM Members only. If you’re looking for a really slick video host that has a bunch of nice customizations, you’ll be super happy with Wistia.

Crowdcast – Alongside Wistia, we also do a decent amount of live workshops. Crowdcast has the most user-friendly interface of any live video provider and they’re constantly making improvements to the platform.

Airtable – Boy oh boy do we looooooove Airtable! Caroline has mastered the art of spreadsheets and Airtable lets her take things to the proverbial next level. We manage all of our WAIM Members, our personal finances, our content calendar, and our ongoing tasks/to-dos within Airtable. I’m not sure we’d be able to run WAIM (or our lives) without Airtable at this point!

Slack – With over 400 WAIM Members, we wanted our own private place to hang out and chat, free from distractions (we’re looking at you FB Groups). We use the free Slack plan and cherish all the amazing features we get. If you run a community or just want a way to chat with friends/co-workers, Slack is a must-use.

Baremetrics – The most beautiful way to keep track of our monthly recurring revenue and overall financial growth of WAIM. Baremetrics takes minutes to set up and is completely automated if you use Stripe (we do have to input our PayPal members manually).

Have any amazing tool recommendations we should check out that you think we’d enjoy? Send us an email.

The Business Analytics That Actually Matter

October 23, 2017

When you run an online business, it can be very easy to get caught up wondering which business analytics actually matter.

Is it your social media follower numbers? Your total website traffic each day/week/month? How much money you make every minute of every hour of every day?

Google Analytics you are confusing

(Oh Google Analytics, I want to love you. I really do.)

With nearly a decade of online business experience, I’d like to share my perspective on the analytics you should be paying attention to. Spoiler alert: None of them will have to do with your social media accounts.

Before we begin, let’s discuss what I’m talking about when it comes to running an online business…

Website – You have a website for whatever it is that you sell. This website should be getting traffic from multiple sources (direct, organic, social, etc).

Product – You have a product (or service) that you sell on your website. It could be a widget, a gizmo, a gadget, or even rare golden thimbles. Seriously though, you sell something for money on your website that people can purchase (via credit card, PayPal, etc).

Subscribers – You have people who purchase things from you and people who just want to get email updates from you. For sake of simplicity, let’s group them together and refer to them as subscribers (and you can segment them later, if you’re into that sort of thing).

Those three items (website, product, subscribers) are what make your business run. There’s typically a direct cause and effect between each:

  1. Your website gets traffic, putting more eyeballs on your product(s).
  2. Your product(s) get purchased or people sign up to learn more.
  3. Your subscribers continue to buy from you or get messages from you.

This loop happens over and over again. You’ve probably experienced this loop in a varying degree of sizes. Sometimes you have traffic spikes, which lead to spikes in sales – Yay! Sometimes you have slow times, which lead to you wanting to pull your hair out and wondering if everything you do should be completely flipped upside and you should go back to that full-time job you used to have – BOO! (don’t do that!) Either way, your online business revolves around traffic, subscribers, and revenue.


The Business Analytics That Should Matter To You: Website Traffic, Email Subscribers, And Revenue

This may not seem like news to you, but for many online business owners, myself included, the data that really matters lies in between each of those main analytics (traffic, subscribers, revenue).

Important In Between Data Point #1 – Do you know your traffic to subscriber conversion rate?

If you don’t, that’s okay! Traffic to subscriber conversion rate is simply the percentage of visitors to your website that sign up for your email list.

Why traffic to subscriber conversion rate matters: Whatever traffic you have coming to your website, you want to capture it and keep the attention of those subscribers (remember: these people purchase from you or pay attention to you). If someone simply visits your website, looks around, and leaves without doing anything, you’ve potentially lost that person forever. Instead, because you’re running a business here, you want them to purchase something from you or at least opt-in to hear from you in their email inbox.

Let’s look at example data for my previous website

Traffic to Subscriber Conversion Rate

(This screenshot is from Spruce Metrics, a business analytics software I co-own and that I’ll talk more about in a moment.)

There are a handful of numbers to look at there, but I’ve highlighted the conversion rate in red for you (you’re welcome!) The month of traffic you’re looking at had 42,002 sessions* (website traffic) on JasonDoesStuff. From those sessions 3,714 people became new subscribers.

Therefore, JasonDoesStuff converted 8.84% of website traffic into subscribers that month.

*We choose “sessions” as our traffic data point of choice because people who are smarter than me agree it’s the most comprehensive way to track a website visitor.

What’s a good traffic to subscriber conversion rate to shoot for? We could go down a rabbit hole discussing what optimal traffic to subscriber conversion rate is, but what’s most important is that you actually KNOW this statistic exists. It shows you how good of a job you’re doing converting a website visitor to an email subscriber. Once you know this data point, then you can start to make tweaks to improve it.

How can you improve your traffic to subscriber conversion rate? Ahhh, great question! There are a ton of things you can change on your website to increase your conversion, but here are the ones I’d propose starting with right away:

  1. Look at the three highest trafficked pages of your website. Do they all have an email signup form prominently placed on the page? If not, get on that.
  2. Explain the value a potential subscriber gets if they give you their email address. Do NOT just say “sign up for updates” or “get on my list.” Don’t do that. Explain the value of what you’ll send them and how it can help them.
  3. I absolutely love my honest Welcome Mat on JasonDoesStuff. It’s just like a welcome mat you might put at the front door of your home.

Popup vs Welcome Mat

I ran a 3-week experiment where I tested a website pop-up (left), Welcome Mat (right), or exit intent pop-up. I wanted to see which option my website visitors preferred. You already know the answer, but you can read more here.

Important In Between Data Point #2 – Do you know the value of your subscribers?

These are people who can pay you in attention (just subscribing and opening your emails), but again, you’re running a business and you need revenue to survive. We want your subscribers to become paying customers.

It can be a bit tricky to calculate the value of your subscribers, but even knowing the estimated value is incredibly helpful.

How do you calculate the estimated value of your subscribers? For nice round numbers, I’m going to show you how to do this annually.

Let’s assume your business generates $50,000 in revenue each year and you have 2,000 total email subscribers during that year. You’d divide 50,000 by 2,000 to get the estimated value of $4 per subscriber.

This is a great piece of data to know because it can show you how your revenue should grow as your amount of subscribers grows (either organically or through paid acquisition).

What do I do once I know the estimated value of a subscriber? Assuming our example subscriber value of $4/per, you can acquire new subscribers at a cost of $3/per (leaving $1 per to make a decent profit). If your subscriber value is much lower, let’s say $0.25/per, you are going to need to have a pretty sizable email list to run a profitable business. A lower value per subscriber would tell me that I need to:

  • Potentially raise the price of my product(s)
  • Improve my sales strategy to get more subscribers to purchase
  • Have additional products my customers can buy

Many online business owners focus on customer acquisition over customer retention. If someone has already paid you (remember: with their attention or by purchasing a product), you should do everything in your power to increase their value* to your business.

*I’m not telling you to hard sell and constantly be pitching your subscribers to buy from you, but you may not be selling enough.

Here are two other business metrics you should keep an eye on…

#1 Subscriber Growth Rate

It can become easy to obsess over how many people subscribe and unsubscribe from your email list. You may know how many new subscribers you get each month (or maybe not), but most email service providers don’t show you monthly growth rate.

Subscriber Growth Rate is your percentage change in total subscribers month over month. Here’s an example of that data, highlighted in red:

Subscriber Growth Rate

You can see in the image above my friend Matt’s Subscriber Growth Rate. He figured out the wonderful combination of acquiring more new subscribers AND lowering his monthly unsubscribes.

If your subscriber growth rate is decreasing and you think it might be due to high unsubscribes, here are a couple things you can try:

  1. On your email signup forms make it clearer of what a subscriber should expect to get from you if they subscribe.
  2. Send consistent content to your subscribers. If you’re just showing up in their inbox every couple months, a subscriber might forget why they joined at all.
  3. Make your welcome email amazing. This first email someone gets right after subscribing will have the highest open rate of ANY email you send (ever). Add some surprise and delight to this email to create a stronger trust factor with your subscribers.

#2 Refund Percentage

This one may be obvious, but many commerce platforms don’t clearly show you what percentage of your sales get refunded. Refund percentage is easy to calculate: Just take the total numbers of refunds divided by total number of purchases.

For example: Let’s say you had 9 refunds on 90 purchases. Your refund percentage is 10%.

To me, 10% is a high refund percentage. Something isn’t connecting between the sales pitch of your product and what the product actually delivers. You can improve your refund percentage by doing a couple things:

  1. Ask people who’ve refunded their purchase why they refunded. Was it the quality? Did the product not meet their expectations? Did they expect one thing and get something completely different? This feedback is critical and should be taken often.
  2. Under promising and over delivering. When someone purchases a product from you, have something unexpected come with it. That doesn’t have to be another product (but it could be). It might be a personalized video from you, a guide to getting the most out of the product, or a well crafted thank you email…

CD baby thank you email

(This is a pretty famous post-purchase email that Derek Sivers used for his company CD Baby. It’s been shared everywhere and customers loved this little surprise after a purchase. This simple email actually become a huge piece of marketing and retention!)


The Only Analytics You Should Care About

The analytics you should be paying attention to for your online business are:

  • Traffic to subscriber conversion percentage
  • Revenue per subscriber
  • Subscriber growth rate
  • Refund percentage

These data points are critically important and can be heavily improved through a handful of things mentioned in this article. Before you try to improve them, you probably want to make sure you’re calculating them and can see them in an ongoing basis!

If you’re overwhelmed by keeping track of all your business metrics and wish you could see them all in one place, give Spruce Metrics ($19/mo) a try!

Spruce Metrics is a piece of software I co-founded and it will help bring your website traffic, email subscribers, and revenue together. Then, we crunch that data for you and show you some of the data points I’ve talked about here (revenue per subscriber is coming soon).

Spruce Metrics JasonDoesStuff

If you want to monitor the business analytics that matter and see it all in one simple dashboard, that’s what we built Spruce Metrics for.

You can stop looking at Google Analytics every day. It’s time you started paying attention to the metrics that are actually going to grow your biz 👍🏻.

Break Out of the 40-Hour Work Week, The Working To Live Framework

May 20, 2017

Do you constantly find yourself wishing you had more hours in the day?

Do you feel like you have very little extra time to spend with family and friends?

Are you running your own business, but feel like your business is actually running you?

What if you stopped letting your business dictate your lifestyle, and instead put a plan in place to put your life first? To put your family first? To stop focusing on when the next chunk of money might come in, and instead built a plan that feels more sustainable?

When I set out on my entrepreneurial journey in 2007, it was all sunshine and rainbows. I wore sweatpants every day. I had some money saved up that felt like a nice cushion. I even had a business idea that took off (IWearYourShirt).

But then, an unfortunate chain of events occurred:

  • I went from working 9-5 to 9-9
  • I never had weekends off
  • I never felt like I could take a break
  • I was stressed to the max
  • I gained weight
  • I had more expenses than I’d ever had before
  • I never had time for friends and family

My life was completely out of balance. To say the rainbows and sunshine disappeared would be an understatement.

The reason everything was out of balance was that I put my business first. I didn’t define the type of lifestyle I wanted. I just assumed a great life would come with a thriving business.

Boy oh boy, was I wrong!

When you don’t start with a plan to control your own business, it will control you.

I know what it’s like to start your own business and feel completely out of control. Like you don’t control your time, your income, or even your decisions (to some degree).

My wife, Caroline, has felt the same way.

Caroline Zook

(Caroline in her natural habitat.) 

In 2014, when Caroline started Made Vibrant, it was a generic graphic design company. Not generic in the way it looked or was represented (obviously, Caroline is amazing), but in that she didn’t have a core offering or a concrete plan for how she should run her business.

Through some hard conversations, we were able to figure out:

  1. The hours that Caroline actually wanted to be working.
  2. What work she really wanted to be doing.
  3. What her prices and product offerings should be.
  4. What bare-bones expenses she had to cover in her business.

When we got to the other side of those conversations, we realized something crazy: she’d been overworking herself to reach someone else’s idea of success. She didn’t have to work nearly as hard as she thought she did. She’d been doing the same things I had been doing with IWearYourShirt, and we’d both gotten ourselves out of alignment. All because we’d put our business goals ahead of our life goals.


The Working To Live Framework Challenges The Conventional 40-Hour Work Week

We believe that the way things have always been done is the way things have to be done. But it’s not true. The 40-hour work week is actually the result of labor laws passed in the 1940s. Prior to that, assembly-line workers often put in 100 hours per week (or more!) at their jobs, and union reps decided that was ridiculous. They fought long and hard to mandate fewer working hours, and they succeeded…kind of. Fast-forward to 2017, and far too many entrepreneurs are back to putting in 100-hour workweeks and calling it “hustle.” It’s not hustle. It’s outdated. And if you’ve ever read The 4-Hour Workweek by Tim Ferriss, you might agree that even 40 hours is too much these days.

It’s never been easier or faster to start your own business, so why are we still adhering to a century-old way of thinking about running our businesses?

I’d like to give you four action steps to shift your thinking from living to work, to working to live.

Action Step #1: Identify your life metrics and schedule them before work

Before we design a business around the life you want, we have to get really specific about what that life looks like.

Questions to ask to start identifying your ideal life:

  1. How many hours a week do you *really* want to be working?
  2. What headaches are you tired of re-living over and over?
  3. What do you never make time for that you’re tired of neglecting?
  4. What are you always wishing you had more of in your days?
  5. What are the things you value most?
  6. What activities bring you the most joy and peace?

I want to challenge you to break down everything you know or expect from “normal” work hours and work days. Remember: YOU get to make the rules.

Here’s an example of how my wife and I break the 9-5 norms and schedule our weeks around our ideal life metrics:

  • We see movies in the middle of the week, usually on Mondays
  • #FreeYourMindFridays (no work on Fridays. Instead, we get outside and explore.)
  • Summer sabbatical (taking 4-6 weeks completely off work )
  • We prioritize exercise and white-space time (time doing nothing)
  • Taking off the entire month of December
  • No calls on Mondays or Fridays

We wrote down the things we wanted and then we worked to have them fit into our lives. It didn’t happen overnight, but without actually committing to making changes, it never would have happened.

ACTION ITEM: I don’t want you to read this article and not work toward making a positive change. It’s time to write down your life non-negotiables and nice-to-haves. Then, up next you’ll learn how to block off time on your weekly calendar, starting with your life (FIRST!).

As an example week, my wife Caroline wrote down these life metrics:

  • Non-negotiable: Work out at least three times a week
  • Non-negotiable: Time to create in my studio
  • Nice-to-have: Daily time for white space (aka “recess”)
  • Nice-to-have: Dedicated time for “adulting” (aka “life”)

Then, she blocked them off FIRST on her calendar:

Working To Live calendar exercise

After her life was scheduled, she THEN added her work blocks to her calendar:

Working To Live calendar exercise part 2

You’ll notice her work hours add up to a 26-hour workweek. Sorry Tim Ferriss, we’re go-getters around here. Joking aside, this is a fairly standard workweek Caroline. Yes, it does change from time to time, just as life changes. But the point is to set the intention each week to focus on LIFE first, then work.

Action Step #2: Break your life metrics down into measurable goals

The way we measure things matters. What we measure = the way we define success.

Are you measuring only money? If you are, you’re conditioning your mind and heart to live or die based on your bank account. Spoiler alert: this is a recipe for never being satisfied.

Instead of thinking about standard business metrics first, how about thinking of life metrics like these:

  • Number of hours you actually work?
  • Date nights you have with your spouse?
  • Trips you take?
  • Hobbies you pick up?
  • Saturdays you spend away from a screen?
  • Getting married on a random Tuesday?
  • Fitness goals?

Let’s bring my wife back into the mix and and show you how she created a practical exercise to write out her life metrics and then reflect on them.

Here’s the practical life metrics chart you can use:

Working To Live life metrics exercise

Here’s Caroline’s life metrics chart filled in (honestly, which is important!):

Working To Live life metrics exercise filled in

Alrighty, this is all well and good. Now that we know what a good life looks like (our life metrics), and how to measure it, let’s talk about MONEY. More specifically: Using money as a TOOL.

Action Step #3: Come up with your “MMM” Number (Minimum Monthly Magic Number)

You may feel the financial crunch of money on a monthly, weekly, or even daily basis. My wife and I felt this exact same way a few years ago. Until we realized we needed a Minimum Monthly Magic (MMM) number.

How do you define your MMM number?

Identify the LEAST amount of money you need to get your Life Metrics where you want them.

There are two questions that can really help during the MMM number discovery process:

  1. How much money are you REALLY spending right now?
  2. Where are you willing to make SACRIFICES to lower that number?

Before I give you the MMM number formula we’ve created, I want to hit home an important point: your current choices about money and life haven’t gotten you where you want to be yet, have they? So, if you aren’t willing to make a change, how do you ever expect to get the things you actually want? Change is uncomfortable, but absolutely necessary.

Here is our MMM number formula:

Monthly living expenses
+ Monthly business expenses
+ Paying off debt
+ Peace of mind cushion
= Your MMM number

I’m bringing Caroline back into the mix because we’ve been using her as a guinea pig, so why stop now??

Working To Live Monthly Magic Number

As you can see, Caroline’s MMM number was $3,000. That number may be high or low for you. The number is only important as a measuring stick to achieving the life you actually want. The MMM number will change over time and may change within the next few months. That’s okay!

One of the major problems we encountered when we were struggling financially was that it was hard to see how much money we were actually spending on a monthly basis. Banks and credit cards show you a list of transactions, but a list can be very difficult to apply to your entire monthly financial situation (aka budget).

If you want some further reading on how we found thousands of extra dollars every year that we could save by making small sacrifices, read our getting out of debt guide. The tip about setting a weekly budget meeting (in that article) may also be extremely helpful for you, as it has been for us.

Action Step #4: Break down the exact changes you need to make in your life and business

Where are you NOW vs where you WANT to be? What’s the gap? How do you make up the gap? Example: $3,000 (your ideal MMM) – $1,000 (current MMM) = $2,000 (MMM gap)

We have three strategies you can use to make up the MMM gap:

Strategy #1 Your product: Charge more per hour, raise prices, look for efficiencies. This is the place you should ABSOLUTELY start. It may not be the sexy and exciting place to start, but it doesn’t require reinventing any wheels. It requires only being willing to make your existing wheel(s) more efficient.

Strategy #2 Your marketing: Get more projects, more customers, new audiences. If you feel your product is on-point, then it may be time for marketing. Marketing tip #1: Marketing is not one tweet, one Facebook post, or one email. Marketing looks a lot like continual effort. Marketing tip #2: Specialize/narrow your offering, and you’ll actually create more opportunities (ex: don’t call yourself a designer, call yourself a designer who focuses on branding).

Strategy #3 New revenue streams. This is the shiny object in the mix. If you’ve exhausted your existing product(s) and your existing marketing for those product(s), it may be time to create/offer something new.

Here’s a handy-dandy decision tree to help you decide which strategy you should work on to help you make up your MMM gap.

Working To Live decision tree

Everyone always wants to START with “new revenue stream,” but that’s the hardest thing. You’re starting from scratch.

Caroline created this chart to help figure out exactly how to fill the MMM gap using the three strategies and then applying specific tactics to make those strategies actually happen.

Here’s a look at the strategies, or the overarching structure she would use to reach her goals:

Working To Live long-term strategies

And then here’s a look at the tactics that she would use to implement those strategies:

Working To Live long-term tactics

I won’t bore you with the long-winded story of how it all worked out, but let’s just say that Caroline was able to go from making ~$1,000 per month to over $3,000 per month in just six months using these exact strategies and tactics. Yes, that is absolutely all the time it took for her to hit her MMM number. And spoiler alert: since that time (two years ago), Caroline has tripled her annual revenue!

Remember your business is the means to get the LIFE you want. Life metrics are the goal, business metrics are how you get there.


Having The Life You Want Isn’t Going To Happen By Accident

If you’re completely happy with your life and business, then you can move on from this article and continue working to live.

But if you’re not happy with your life and business, it’s time to take action. It’s time to look through the four action steps and put in the work I’ve outlined here.

This isn’t a get-rich-quick solution. You will have to make sacrifices You will have to put in some hard work. If you aren’t willing to break your bad habits you’ve picked up over the years, how can you ever expect anything to change?

Embrace short-term pain for long-term gain.

The best way to find hidden money you can save right now is to list out EVERY expense you have (line by line) in one spreadsheet. Once you have that list, you’ll find places where you can make sacrifices.

Getting the life you want typically has to do with money and time. Let’s look at both and how you can make sacrifices with each.

Money: Here’s what we found when we made a list of all our expenses and took a hard look at trimming back (in the short term):

  • Eating less meals out: saved us $1,000/month
  • Calling credit card companies to reduce monthly APR: saved us $400/month
  • Not doing any unnecessary shopping: saved us $300/month
  • Reducing our phone bill by calling AT&T: saved us $100/month
  • Cutting cable: saved us $100/month
  • Stopping business product subscriptions: saved us $250/month
  • TOTAL SAVINGS: $2,150* every month!

*Your number may not be close to this, or it may be higher. No matter what, find YOUR amount of money you can save each month by making a few sacrifices.

Time: Here’s how we found more hours we could spend enjoying our lives (or using for Action Step #4 above):

  • Limiting social media to twice per day: saved us 3 hours
  • Limiting Netflix to two hours at night: saved us 2 hours
  • Limiting time reading articles/emails: saved us 1 hour
  • Limiting time spent using iPhone: saved us 1 hour
  • TOTAL SAVINGS: 8 hours PER DAY!*

*That’s an extra 240 hours each month! These numbers might shock you and they shocked us too. Start keeping track of your time spent in a journal or through an app like RescueTime

Did you catch that? We literally save ourselves an entire 40-hour work week just in “wasted” hours. We could each work an extra full-time job with those hours! (Or not. That’s the whole point.)

People don’t focus on this stuff enough (I know we didn’t!). As business owners, we’re always telling people what’s possible, but we often forget to share what it takes to get there. We had to give up A LOT in the short-term to experience the life that we now have.

What are you willing to trade to get the life you want?

These aren’t forever changes. The things you sacrifice now are simply a way for you to accelerate your journey toward having the life and business you want.

The problem is that so many people don’t want to give things up, so they settle for tiny pieces of the life they want in the present instead of buckling down and making sacrifices in the short term to experience the WHOLE of the life they want in the longer term.

As a final note, I really want to distinguish between the short-term pain of budgeting and sacrificing to achieve your ideal lifestyle (which I advocate), and the so-called short-term pain of working crazy hours now so you can become a millionaire in a few years (which I have done, and do NOT advocate). Not all sacrifices are the same. Your life and time are as important right now as they will be when/if you reach some random IPO goal in the future, so please consider your whole life when making decisions about where to spend your time and money.

We’ve given you the exercises. We’ve talked about the theory of Working To Live. But now it’s up to you.

Are you going to put in the time it takes to have the life you dream about?

Are you going to embrace the short-term pain to achieve the long-term gain?

If you’re working your ass off right now and wondering when you’ll finally be able to come up for air, let me leave you with this one question:

What is it all for, anyway?

Honestly? What’s the point of all the blood, sweat, and tears — the launches, the clients, the hustle, the risks — if not to architect a life filled with all the things you’ve always wanted?

Challenge All of the Assumptions, Especially Your Self-Limiting Ones

May 7, 2017

Whether you’re looking to succeed in business or make changes in your life, the first step is to challenge your assumptions.

Our brains have this mystical, magical, and commanding power over us. We know this. We even acknowledge it. But it can be incredibly difficult to challenge our own thoughts.

Phrases like “I don’t think this will work” or “I don’t know what will happen” are assumption-based.

We give our assumptions more authority and power than they deserve when trying to make decisions and take action.

I’d like to tell you I’ve come up with a perfect framework for you to test all your assumptions and never let your assumptive thoughts dictate your decisions again. But I haven’t. Maybe someone way smarter than me does, but all I have to share is a life of assumption-challenging experiences.


How To Challenge Assumptions When Starting A Business

I’m amazed at how often I hear from people who are talking themselves out of being successful (a term, for which, you must define yourself, not based on any outside metrics). They use phrases like these:

  • “My idea has already been done before”
  • “I’m not special. Why would anyone care what I have to say?”
  • “I don’t have the skills required to make my idea happen”
  • “I can’t make money doing what I want to do”
  • “I don’t know where to start”

Let’s attack these assumptions together.

“My idea has already been done before.”

AWESOME! That means the market is proven for this product or service. People are already paying for it. The assumption you’d want to test (people being willing to buy this) has already been proven for you, and you don’t have to scale the huge mountain of trying to prove that there are actually people out there who will pay for your idea. It’s a good thing that there are are virtually ZERO new ideas left. Our species is too smart. Everything is just a remix of other ideas at this point. Embrace what makes your remix of an idea unique.

“I’m not special. Why would anyone care what I have to say?”

Whoever told you that you weren’t special was an a-hole. You are special. I am special. We are special little snowflakes. Now that we’ve gotten that out of the way, being “special” isn’t what’s going to help you succeed, anyway. No one lines up to buy the newest iPhone or pair of Air Jordans because Steve Jobs or Phil Knight are special people. They are special (just like you and I are), but the blood, sweat, tears, work, sacrifices, failures, mistakes, and assumption-testing thinking is what’s led to you wanting to buy the product they’re producing. People will absolutely care what you have to say. You just have to understand it may take years for you to find the right, resonant way to say it. You are significant.

“I don’t have the skills required to make my idea happen.”

I have virtually NO specific skills. I’m a jack of all trades, master of none. I dabble in design, but I’m years behind designers whose work actually receives praise and accolades. I don’t know a thing about programming languages. I’m terrible at managing people. Really, you could argue, all I have are my ideas. But yet, I find ways to turn my ideas into realities. I seek out people to whom I can outsource my weaknesses. If you really want your ideas to happen, the skillset you have doesn’t matter one bit. The only skill you need is the work ethic to figure out how the heck you’re going to get your idea out into the world. Someone else in the world knows what you don’t. Find them. Pay them money. Exchange something for their time. No skills required.

“I can’t make money doing what I want to do.”

Why not? Because other people haven’t been able to? Because others already have? Those are other people, they aren’t you. I’m never willing to accept assumptions based on the actions of others. This is a blessing and a curse. But you can make money doing literally anything right now. I once wrote a silly joke in an email about becoming a professional snuggler. Then, a few weeks later, I received an email from a woman named Sam who actually created a popular Snuggling Agency because of my silly joke (amazeballs!). I’ve made money doing weirdly outlandish things. My name has been included in segments on TV called “they get paid for that?” and “jobs you never thought you could get paid for.” As the old adage goes, you won’t know until you try. And as it relates to making money doing what you want to do, you absolutely won’t know until you try (and try in all the different ways that other people haven’t thought of before, or in ways they haven’t done it as well as you will).

“I don’t know where to start.”

By reading this article, you are starting. By wanting to start, you are starting. But those things aren’t enough. Eventually, you just have to put one foot in front of the other (or click a mouse one click in front of the other). Because guess what? I didn’t know how to start, either. I still don’t know how to start most projects, but I do it, anyway. I find my way by giving myself permission to start ugly, learning all I can, and then trusting my intuition along the way. It looks different every time, but the important part is that I start at all.

There is no straight line to success

Our culture loves to tout the successful. Magazines, TV shows, movies, and websites love to glamorize how people “made it” and “became so insanely rich they turned into a pile of money and flew off in the wind.”

People assume success is a straight line. You start on your little dot on a map. Then you cross a single line, and you’re at the X. Success!


Success looks like a treasure map.

You follow a dotted line that twists, turns, curves, hits all kinds of obstacles in your way, and eventually you find the X (maybe).

Treasure Map illustration by Tim Vandevall

(Treasure map illustration by Tim Vandevall)

The unfortunate thing about the treasure map to success is that sometimes you get shipwrecked. Sometimes you get stranded. Sometimes your only friend is a volleyball. No one can predict when you’ll get marooned on a deserted island (read: when you will have a mistake or failure). But it will happen. It happens to everyone at some point or another.

Just like testing all your assumptions, if you accept the fact that success looks like a treasure map, you’re going in the right direction. You will veer off path. You will hit roadblocks. You will have challenging moments when you question the entire journey altogether, but the journey wouldn’t be worth it if you didn’t.


Why You Should Test All Of The Assumptions All Of The Time

As I mentioned, there’s no framework for getting better at testing your own assumptions. All you can do is make the decision to start testing all your assumptions (and the assumptions of society, your friends, your family, etc.) all of the time.

I don’t assume anything will work a second time around. I don’t assume that just because I read something in a book that it will work for me. I don’t assume that because someone else does something a certain way that’s how I need to do it.

I test those things. One by one. Assumption by assumption.

Here’s one question that always helps me when I’m on the dotted line of my treasure map and being met with an assumption:

“Have I dealt with this exact issue before with the same exact circumstances?”

Almost always, the answer is “No.” It’s nearly impossible for the answer to be “Yes.” And because the answer is “No” you have to test your assumptions. Sometimes, it feels like you’re re-testing assumptions you’ve already re-tested in a re-test of assumption re-testing before. Well, welcome to life and business. It’s not a straight line. It gets pretty damn windy, and you’d better hold on for the ride.

My wife, Caroline, and I have some of our most emotionally charged discussions when testing assumptions. We typically use the three whys:

“Why does it have to be done this way?”

“Why do we have to run our relationship the same way as other people?”

“Why do we ever have to do anything the same as anyone else, ever??”

That last one is a troublemaker, and admittedly, must be obnoxious to deal with (Sorry, Carol, love you!).

Constantly testing assumptions in life and business has gotten me where I am today. A place where I truly feel I’ve “made it.”

That’s not because of a certain amount of dollars in my bank account, and it’s definitely not because of a number of friends I’ve amassed on a social media site.

The point here is that I’ve “made it” because I’m willing to question everything (and I have the ability to do so). I am in control of my outcomes and I’ve earned every bit of success I’ve achieved. I could lose everything in an instant, and I’d be okay, because I know what it’s taken me to get where I am today. A place (or some version of it) I could get to again, knowing I’ll have to follow a pretty damn windy treasure map to get there.