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The 3 Myths of Passive Income You Should Avoid

January 30, 2019

Have you felt overworked and wishing you could generate that elusive thing called passive income?

Well, friend, you’re not alone. We’ve spent the better part of a decade trying to master generating revenue while we sleep and we’re here to tell you it’s not as simple as some folks may lead you to believe (#spoileralert #realtalk).

With our disclaimer out of the way, we do want to let you know that it is absolutely possible to make some extra side income so you can feel a bit more financially stable. 

We’re going to talk specifically about three myths when it comes to creating passive income with digital products. Ready to rock? Let’s do this!

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

Passive Income 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.


Passive Income Myth #1

You can create a passive income business without building an audience

Other people make it sound easy right? Build a digital product, spin up a sales page, go to sleep and wake up every morning with more money in your bank account. The issue is that most of us have tried this and it hasn’t worked.

Passive income only works when you have a steady stream of qualified traffic finding out about your product.

In today’s crowded digital landscape, potential customers need to hear from you multiple times and learn to trust your expertise over time. This means you’ll need to capture their attention and communicate with them on an ongoing basis if you want to sell to them, and that means building an audience.

By the way, when we say build an audience, we don’t just mean on social media. Social channels are where most people consume passively — they scroll or read for a moment and then it’s on to the next thing. It’s a great place for awareness or reminders, but not necessarily sales.

Instead, you want an engaged email list providing consistent, helpful content tailored to your target audience.

Attract them by delivering value, and continue to deliver that value to build trust, or else your “passive” product will remain the best-kept secret on the internet, and secrets don’t add up to revenue.

RELATED GUIDE: The Ethical Guide To Building An Email List Without Sleazy Tactics


Passive Income Myth #2:

Passive income is ‘set it and forget it’…and it will last forever.

Most people assume that if they can just get the right funnel with the right price point and the right strategy that sales will roll in and never dry up.

The truth is, things are always changing in online business. Ad prices, media habits, competitors…it’s always shifting.

That’s why you need a clear plan for tracking your product performance and evaluating your marketing efforts on a regular basis.

You can set it and forget it for a WHILE, but eventually, something will change and you’ll have to tweak things and test them in order to respond.

The biggest thing to realize here is that passive income isn’t the savior of your business—the thing you set up one time and spend the rest of your time counting your money. You have to continuously test, tweak and evolve if you want to keep those sales coming.


Passive Income Myth #3:

You can create passive income products about anything, even something you don’t have direct experience in.

In the “passive income” world, we often see people trying to jump on a trend or topic that there’s demand for. They’ll try to teach you how to be more effective on Instagram, for example, without themselves having figured out how to be effective on Instagram.

This is something our friend Paul Jarvis calls teaching “second-hand knowledge” and it could work, but customers aren’t as easily fooled as marketers want to believe.

We believe the best digital product ideas are the ones that stem from your authentic experience.

Make sure your product is on a topic you know intimately, with processes and information you’ve picked up and practiced over time, and add your own unique personal spin to it.


If you’re looking for a step-by-step program to help you launch digital products and potentially create passive income 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 Actually Create Passive Income:

Let’s recap what it really takes to build up a passive income source

#1 Make sure you have a good email list to create passive income

Your email list needs to deliver consistent, helpful information about your product topic. Don’t send out a bunch of fluff email content. Don’t list of a bunch of links unrelated to what you are trying to sell. Be direct. Be helpful. Be consistent.

#2 Re-evaluate your passive income funnel every 3 months

Use an experimenter’s mindset to figure out what works and what doesn’t to build up passive income. Remember: There is no set it and forget it. You need to set things, check on them, tweak them, and not forget about them.

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

#3 Create a passive income digital product you have direct experience with

Create a product around something you have hands-on knowledge of and can speak confidently about. You want to make sure to teach in your own unique way and with your own twists. Don’t try to sell secondhand knowledge.

Last but not least when it comes to passive income…

You can’t just create a product and put up a sales page expecting it to bring in real revenue for you overnight. Like anything else in your business, it takes time and effort and passive income is not the silver bullet everyone wants it to be.

The sooner you let go of the desire for it to solve all your financial difficulties, the sooner you can get to work making REAL product income that can positively impact your life.

The Things We Wish We’d Known When We Started Our Businesses

January 7, 2019

Don’t Need Video? Listen Now

Episode Summary

Whether you’re starting a business or you’ve been on your own entrepreneurial journal for over a decade like we have, we’ve got some lessons learned and tips for you in this episode!

When was the last time you set out to plant seeds for your business? No, not actual seeds, but tasks and to-do items that may not bear fruit for many months? This can seem difficult if you’re trying hard to generate revenue right now, but it’s an important way to shift your thinking to play the long-game with your biz.

We also discuss how to use an “experimenter’s mindset” with your business and practical next steps. So much of our positive progress and growth has come from putting our ideas and assumptions to the test (and not counting ideas out before giving them a chance!)

And we chat about comparison traps, dealing with feelings of overwhelm, and focusing on taking imperfect action. Lots of goodies for you this week!

QUESTION FOR YOU: What seeds are you planting for your business this year? (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.

Watch Us Build Our Next Business, Wandering Aimfully, In Real-Time

March 26, 2018

You’re looking at the BRAND NEW Wandering Aimfully website! YAY! We’ll update this post in a few weeks and you can still read our under construction articles here.

This is no small feat for us. I’ve been hinting at this project here and there, including a mention in my State of the Union at the beginning of this year. This is the business baby my wife and I are having together (sorry folks, human babies are a bit further down the line).

Don’t need to read anymore? Want to check this new biz out?

Note: This post will be updated weekly, so feel free to check back for updates in the “WEEKS” section below.

What is Wandering Aimfully?

JasonDoesStuff (and The Action Army), Made Vibrant (my wife’s biz), and BuyOurFuture are turning into: Wandering Aimfully

The journey to combine our three business ventures into one has officially started. And of course, we’re being complete weirdos and sharing EVERY DETAIL. If you want to get daily emails and see all the nitty-gritty details we’ll be undertaking, you can click here to get daily updates.

You may be wondering why I’m making a big deal about this transition. Isn’t it easy to spin up an online business?

  • You buy a domain
  • You create a biz plan (of sorts)
  • You build a brand and website
  • You create some (meaningful) content to attract customers
  • You promote your biz in some way
  • People pay you
  • Boom – you’re in business!

Now we all know there’s a bit more that goes into creating an online business, but it gets even more complicated when you’re taking multiple existing biz properties and joining them together.

That’s why we’re going to share all the details on our Under Construction Wandering Aimfully website.

Here’s a bit more of exactly what we’re going to be doing and sharing (I’ll be updating this weekly):


We have a business name, Wandering Aimfully, but what the heck does it mean? What does it do? Who does it serve? What does it look like? All those questions and much more were be answered.


We aren’t writing a business plan in the conventional sense, but we are planning out the business. What are we selling? How much will we charge? What happens to existing customers? How are we working together as a husband and wife team? Read more here.


We’ll have a standard consumer-facing website, like anyone else (with an about page, blog articles, etc), but we’re also building a kickass customer experience like no-other. We definitely didn’t finish all the designs by the end of this week, but we made huge progress.


Articles? Social media? YouTube videos? A podcast? Where does it all fit in? What happens to all our existing content? Read about our intentional approach to creating meaningful content (and not being on ALL the social media sites).


We’re using an open and closed launch strategy to sell our monthly memberships. But, we also decided to take pre-orders. Get caught up on that.


While we took a break to go on family vacation, our developers didn’t. They were hard work turning our designs into a reality. When we got back into word mode, we shared some of the biggest challenges we’re facing.


This week was the start of migrating our content from JasonDoesStuff, Made Vibrant, and BuyOurFuture into our new Wandering Aimfully WordPress site. I say “the start” because we didn’t get very far.


We have some updating to do… hah.

This will be no small undertaking. In fact, we’ve already been working on it, planning, and ideating for months. But we want to pull back all the curtains and share as much as our sanity will allow.

The under construction site for Wandering Aimfully won’t have much to it the first few days, but very quickly it’s going to fill up with daily posts, weekly videos (sometimes with completely unedited planning meetings we’ve had), and hopefully a bunch of fun peppered in!


JasonDoesStuff and The Action Army will cease to exist after this change… and that’s scary.

The good thing is, I won’t be changing at all. Hah. My action-taking focused content will continue with Wandering Aimfully, but this site and my weekly email newsletter will go away completely (ahhhhh!). We worked that out and talked more about it in Week #4!

If you’re an Action Army email subscriber, here’s what you can expect to get in your inbox the next few weeks:

  • What’s gone well for us?
  • What’s gone wrong?
  • How are we staying sane during this process?
  • Do we have any semblance of a life? (spoiler alert: you bet we will!)
  • What are our goals and aspirations?
  • How can you be part of the journey?

The fun thing, and what I’m really excited about, is that Wandering Aimfully means so much more than “JasonDoesStuff” ever did.

There’s so much more value I hope to bring to your life and business as we move forward on this adventure.

I can guarantee we’ll mess a few things up along the way, but I’m hopeful you’ll enjoy seeing how we deal with those inevitable bumps in the road.

Here’s an Easy Way to Decide Between Being a Specialist or Generalist

August 30, 2017

One of the toughest questions I’ve wrestled with during my time as an entrepreneur is: should I be a specialist and focus on one thing, or be a generalist and explore multiple interests? 

You may be struggling with the same question. Trying to figure out what your “niche” is, or whether you’re better suited to working on lots of different things.

I believe I’ve found the answer to our question, and it has to do with money. That precious thing that gives our businesses oxygen. That commodity required to feel a sense of freedom in our lives. Good or bad, money makes the world go round, and it’s the simplest answer to the specialize/generalize question I’ve discovered.


Specialist or Generalist? Here’s how to decide…

Do you need money in the next 90 days? You should be a specialist and focus on one thing.

If your goal is to make money and be profitable as quickly as possible, specializing is the absolute best option. Pick one thing to focus on. Solve a very specific problem for someone (or yourself). This will help you build a business quickly and efficiently.

Remember one important thing about building and running a business: A business is the exchange of goods or services for money.

There must be something you are giving someone in exchange for money to qualify as a business and to have any chance of sustainability.

What are some types of specialist businesses that you can focus on and generate money quickly?

Within the next few days/weeks, you can make money…

1. Selling your time (aka freelance design, development, photography, videography, etc)
2. As a 1-on-1 consultant or coach

Within the next 90 days, you can make money…

3. Building a software application (also known as SaaS)
4. Creating a mobile app
5. Offering in-depth educational content (online courses, workshops, etc)

Those lists could go on and on, but the key here is to keep things simple and focused. The simpler you keep things, especially in the early stages of business, the easier your life will be and the quicker you’ll make money.

Specializing gives you a clear path to hone a specific skill. Some folks call this your “zone of genius.” Be bullish on mastering that zone. Don’t let anything distract you.

Specialist Example: Let’s say you want to be a freelance photographer.

Step 1 (First Day) – Buy the best camera and lens(es) you can afford. If you have no budget for new gear, use what you have (an old camera gathering dust in the drawer, your dad’s camera, or even your phone camera), and move to Step 2.

Step 2 (First Week) – Give yourself one week to consume as much knowledge about your camera and the craft of photography as you can. Watch YouTube videos. Read in-depth articles about composition. Take an online course about running a freelance photography business. Be a sponge. But finish being a sponge after the first week.

Step 3 (First Month) – Use the hell out of your camera for one month. Shoot every event and situation you can. Take 500-1,000 photos per day. Delete them all. Shoot. Delete. Shoot. Delete. Build up your resistance to taking the perfect photo, and just learn your gear and hone your photography skills.

Step 4 (Second Month) – Spend one month doing unpaid photography work for friends. Headshots. Weddings (even if they have a “professional” photographer, ask to tag along). Corporate shoots. This could be done in conjunction with Step 3.

Step 5 (Second Month) – Build a super simple website. I’d recommend using a template from Squarespace. Give yourself one weekend to put your site together. On the homepage of the website highlight the type of photography you want to focus on (weddings, corporate, etc). Showcase your work based on that focus*. Give someone a way to pay you for an hour of photography (or at least contact you for bookings. is a great option). Make a list of 25-50 friends, and email them your photography website. Ask them to share it with anyone they know who might need your services.

*Remember: We’re specializing here so we can get to money-making as quickly as possible.

Step 6 (Third Month+) – Search local event guides, reach out to small businesses, or scour craigslist for happenings in your city that might require an official photographer. Call the decision makers and pitch yourself and your services. Keep shooting. Keep getting better. Keep trying to find your unique photography style. Kick serious ass and over deliver so that these local event folks want to share you with their friends.

I guarantee if you followed those six steps you would build a profitable photography business in just three months. Sure, you may only be making $500-$1000 in your first month, but that’s more than $0. And once you start making money and landing clients, more opportunities will come your way.

If making money immediately isn’t an immediate priority, become a generalist without a niche.

In 2013 I set out to reinvent myself and my business. I gave myself a two-year window to be a generalist and consistently experiment. In those two years, I had a very broad focus (and still do!). By being willing to create all kinds of things, and in my own way, doors opened.

Sometimes the door of your business is barely cracked. Sometimes the door of your business is wide open. But either way, the door isn’t shut!

Being a generalist and not having a singular focus will lead you down many paths. 90% of those paths help you learn what you don’t want to do.

It’s often more important, in the long run of running and owning a business, to figure out all the things you don’t want to do be doing.

You don’t learn and grow from success. Where the learning and true growth happens is when you screw up and when things go bad.

What are some pursuits that are more generalist?

  • Start a blog, podcast, YouTube channel, or newsletter to explore and share your interests publicly. Invite all your family and friends personally to subscribe, share, and follow along. Commit to these for at least six months to give them a chance to succeed.
  • Conduct a 30-day experiment and record your experiences in real time on your site, Medium, etc. Do multiple experiments and continue to share them.
  • Write up a bucket list for the next year, and commit to doing one or two things on that list every week. (Obviously, this list will have to be more practical than outlandish, but you know what I mean.)
  • Learn six new skills in the next year. Use a service like Treehouse to learn something in a month, then apply that learning by using that skill for a month. Rinse and repeat five times. Do any of your new skills stand out as something you should continue doing?
  • Become an apprentice to people/companies you admire. Pick 3-4 companies and offer your effort to them for free for 30-60 day periods of time. Soak up all the experience you can, especially if you can work in-person. (Tip: The quickest way to get these folks to say “yes” to you is to give them a plan of exactly what you can/could do to help them and how you’ll provide value.)

Just like the specialist lists above, this one could go on, but the secret to success here is to avoid becoming too narrowly focused. Don’t get too specific about what you’re doing or where you’re going. Stay open to possibilities, take care to notice the doors that open as you do so, and decide on the fly whether to walk through them.

Being a generalist keeps your options open and lets you develop some competency in a variety of skills. You’ll harness distractions as opportunities to discover and pursue something cool.

In summary…

I’m not advocating that you become either a generalist or a specialist. That choice is up to you, but I think the question of when you need money helps to make the decision simpler.

Need money now? Specialize. Pick one skill and GO.

Have time? Generalize. Enjoy the ride and soak up all the experiences.

How To Start A Creative Business: Focus on the Foundation First

June 5, 2017

I started my first blog back in 2011.

May 18, 2011 to be exact. How do I know this? Well my first post still exists. You can read it here. (But not yet! You have a whole email to get through first before I lose you to the time machine/rabbit hole known as the internet. SO keep reading then you can satisfy your curiosity by seeing what the 2011 version of me found so interesting to write about…)

Back when I started this first blog, I had just ONE intention: get the thoughts and ideas swirling in my head out and “on paper.” I felt like I had things to say and every day that went by without saying them felt like a waste of creative potential.

My own self-doubt was my greatest challenge, so just hitting ‘publish’ on a post was a HUGE win for me. The more posts I published, the less fearful I felt. The more confidence I gained.

Once I got a handle on my doubt and cultivated the self-discipline to sit down and actually write, my One Intention evolved.

I actually want people to read this, I thought. So I shared links to my blog posts on Facebook with my friends. And on Twitter with people following me. And people started to read my posts and share them. I started to build a tiny audience of people who cared about what I was making and what I had to say.

For the next three years, it didn’t even occur to me to try and turn this creative outlet into a business. I let pure passion and curiosity direct my time and attention. I taught myself design and Photoshop. I honed my voice and my writing skills. I learned how to stick to a content schedule and to get over my perfectionism. I figured out what I believed in. 

All of these things turned out to be essential in building a strong foundation for the creative business that would evolve from it all by 2014 when Made Vibrant was born. That’s when my One Intention became finding a way to turn my creative expression into something of value for others, something my small audience of people might pay me for.

Now… why am I sharing all of this with you and taking you down Made Vibrant Memory Lane?

It’s actually to illustrate a point that I think could help SO many of you out there, especially those of you still searching for a way to turn your skills and passions into a business. It starts with this advice:

Focus on trying to walk before you try to run.

I know you’re probably searching for the blog posts or the online programs or courses that are going to give you that one magical shortcut — the thing that is going to take you from no audience to a paying audience like yesterday. And it’s only natural for you to want that, especially with how many more resources there are now online about how to start your business.

Trust me when I say this, though:

Searching for a shortcut is actually just distracting you from the one tactic guaranteed to be effective: putting in the TIME. 

“Searching for a shortcut is actually just distracting you from the one tactic guaranteed to be effective: putting in the TIME.”

Every day and month and, yes, YEAR that goes by while you try to plan out the perfect strategy, that is all time that you could have spent actually making something, which is the foundation for any profitable creative business. Time you could have spent honing your voice and your skills. Time spent figuring out what YOU believe in.

It’s all too tempting to focus on the big, complex, well-oiled machine thing right out of the gate. You want the polished brand, the booming blog, the online products bringing you passive income, the adoring audience with thumbs and hearts and comments at the ready, the segmented content based on interests, the podcast interview requests, the book deal and the sponsored travel.

If this is what you’re chasing down though, it’s likely that you’re going to find yourself with a lot of half-baked ideas, more spinning plates than you can handle, and a lot of unmet expectations.

Instead, I recommend doing what my 2011-self did. Begin with ONE intention: to get your ideas out of your head.

Hone your message. Develop your confidence. Figure out what you want to say. Better yet, figure out HOW you want to say it by going within to understand who you are and what makes your perspective on the world one-of-a-kind.

To put it simply: focus on the foundation first.

All big, beautiful trees must begin with a seed, right? This seed may be a simple beginning, but it is powerful with potential. From it, a network of strong and sturdy roots begins to spread, creating a foundation that will support whatever complex growth this tree might undergo in the future.

What I would do if I was starting a creative business right now from scratch

If I was starting my business over from the beginning, here’s how I would start simple and layer in the complexity as I grew.

1. Begin by making things FOR YOURSELF.

Practice getting those ideas out of your head and into reality. What is your craft? How can you improve it and develop your own unique recognizable style or approach to what you do? Do you enjoy what you do? Would you still do it if no one ever paid you for it? There isn’t a shortcut to making things, so start TODAY. Quit strategizing and start making.

2. Share your work (consistently).

Once you know your intention is pure and your craft is somewhat focused, you’re in the best place to connect with an audience. However, you can’t build an audience of people who value what you do if they can’t see what you do. Create a portfolio. Share your writing. Post your artwork. Take on pro bono work. Whatever you need to do to make your work visible, do that. Stay connected to your audience with a newsletter or through email correspondence — social media changes all the time but email is still the best way to maintain a line of communication with your audience that you control.

3. Identify ways to package your skills.

AFTER you’ve spent time building an audience and you know you have something that connects, consider ways that someone could pay you in exchange for your skills, services or work. Then… ask. Avoid making assumptions about what people will or won’t pay for. Instead, test those assumptions by making the ask and learning from the results.

4. Evolve, evolve, and evolve some more.

It’s entirely possible that you’ll go through several ideas — some winners, some losers — while you figure out a business offering that connects with your audience AND makes you sustainable income. That’s okay. That is the core challenge of being a creative entrepreneur. If you can’t find a way to enjoy that process of trial and error, well it’s possible that owning your own business may not be the right path for you.

5. Optimize your processes and deepen the connection with your audience.

Many people make the mistake of trying to over-optimize before they have any sustainable revenue streams, and this is what leaves them completely overwhelmed and exhausted. (I’ve been guilty of this myself.) It’s probably not all that helpful to distract yourself with automation and list segmenting and marketing to new audiences if you don’t even have a product or service offering that is working yet. Remember, focus on the foundation BEFORE you add unnecessary complexity to your business. That is the key to not completely burning out before you land on something that works.

I know we all want to skip ahead to “the good part.” The part where it’s all working smoothly, we’re making a sustainable living, and we get to spend our days creating and doing what we love.

But trust me, for the sake of your creativity and your sanity, begin with the roots and THEN branch out as you go, when it makes sense. 

If you give yourself permission to block out the branches for now, to focus on the foundation—planting the seed or strengthening the roots—you may finally get that “shortcut” you’ve been hunting for in the form of some good old-fashioned hard work.

The Difference Between Getting Paid and Making Money

January 29, 2017

I’d made well over $13 before 2008. In fact, I had a perfectly acceptable 9-5 job that paid me thousands of dollars per month (as many of you reading this probably do). But on one morning in 2008, I made $13 and for the first time in my life experienced making money completely on my own. Someone random on the Internet paid me money for an idea I had.

I’d made every single dollar, until 2008, in “normal” ways. I did chores as a kid and had an allowance (it was measly, but aren’t all allowances supposed to be that way?). I had a handful of “normal” jobs growing up:

  • I mowed lawns as an angsty teenager.
  • I worked at a “health-food grocery store” as a produce boy, and sometimes register boy when they weren’t afraid that a 15-year old kid would pocket money from the cash machine (quick aside for the younger readers: Cash was this thing we used to carry around in our pockets. It was like paper, but it had weird, made-up value. Oh, you know what cash is? Great, we’ll carry on!).
  • I sold pagers at a Verizon store.
  • I pumped gasoline at a gas station.
  • I worked as a summer camp counselor.
  • I had a whole bunch of part-time design jobs.

I share all of these jobs with you to point out that it was always a standard payment for services rendered. Normal jobs, if you will.

My first taste of entrepreneurial money

In 2008, I got my first taste of entrepreneurial money. That sweet, sweet nectar that I became addicted to and would continue to chase (and still do, but in a healthy way). My IWearYourShirt business had just launched to crickets (and they didn’t have money, those cheap-insect-jerks), and I started emailing friends and family to share my website with them. This was both in a moment of panic, but also because I had a thought: “If I don’t tell people about this idea, how in the world do I expect them to find it?”

Don’t be afraid to share your ideas. If you’re proud of what you’ve created, share it!

Those few emails to friends and family weren’t sales pitches. They were just friendly hellos, accompanied by a request to check out or share this crazy t-shirt wearing scheme (err, business) I had come up with. Unbeknownst to me, a few of the email recipients took pity on me and deposited money into my PayPal account via the fancy buttons on the website link I’d sent them.

Brace yourself: After the first day of sending emails, I’d made $13.

I’ll give you a moment to pick yourself up off the floor. Are you okay? You are? Great. Things get a little bit more exciting from here.

In the coming weeks after sending those first emails, the money-making part of IWearYourShirt started to gain some traction.

That $13 increased to $500. Then $1,000. Then, after two and a half months of emails and tweets, I was looking at a PayPal balance containing over $6,000.


The Difference Between Making Money And Getting Paid

I’m going to steal this wonderful sentiment from my wife, Caroline. Mostly because she’s the better writer of the two of us, and because… joint household (see, babe? If I win, we both win!)

Anyone can get paid. Anyone can get a job. Anyone can exchange time for money. But it’s another ball of wax (why is it a ball of wax? who even has ever owned a ball of wax?) to make money.

When my IWearYourShirt business started making money, I noticed a shift in my thinking. Sure, I’d read about and seen other people who were making money from their ideas, but I had never done it. I had never had that experience.

That first $13 was like seeing the light. It opened my eyes to this idea that you literally can do anything and make money from it.

If getting paid to wear t-shirts isn’t proof of that, I don’t know what is. The feeling you get when someone gives you money for your thoughts is unlike any other. Many successful people, or at least experienced entrepreneurs, will tell you that the money itself pales in comparison to the transaction that happens. Someone is essentially voting for you, saying YES to you, with their dollars. If you haven’t felt this feeling before, I will warn you: Once you feel it, you won’t want to stop feeling it.

You don’t get what you don’t ask for

This little eight-word phrase has become a mantra for me. It works well in life, but it works especially well in business. Any time I have an idea and self-doubt starts to creep in, I simply combat that self-doubt with the broadsword of asking. It’s not a physical broadsword, although that would be really cool. But it is a metaphorical-weapon I keep in my arsenal.

Self-doubt will say, “You’re an idiot! no one will pay for this! Hahahahaha, you’re also ugly!”
(We all know self-doubt is also a name-calling a-hole.)

My broadsword of asking will reply, “You may be right, self-doubt, but we won’t know until we ask, right?”

Then self-doubt retorts, “You’re still ugly!”

It’s silly, especially imagining self doubt and a broadsword arguing, but we all deal with it. We all have some version of these thoughts. But if I’ve learned one important thing since making my first $13, it’s this:

The asking gets easier over time.

The rejection you receive from asking also gets easier over time, because you know you’ll have something more interesting to ask for again in the future.

This eight-word mantra, “You don’t get what you don’t ask for,” has popped up time and time again since that initial day in 2008. I continue to refer back to my broadsword of asking. I continue to make money, not only because I have ideas and execute them, but also because I’m unafraid of the consequences of asking.

Making money makes momentum

How about that for a sweet alliteration? It’s also the truth. If you can land ONE sale, you’ll feel a sense of empowerment that can fuel you to continue. But without that one sale, you can feel powerless.

So, is it that simple? You just have to make your first sale?

I’d say: YES.

Sure, you aren’t going to retire rich, pay off all your debt, and buy that gold-plated yacht you’ve been dreaming about with just one sale. But it will give you something you can’t manufacture: momentum. And with momentum, you can push through and more easily combat your thoughts of self-doubt.

If you’ve already made your first sale, awesome. Relish that. Enjoy it. Learn everything you can from it so you can make your next sale. And then your next. And then your next.

I hope you make way more than $13 from whatever you’re working on, but don’t lose sight of the fact that everyone starts with a version of this story. And everyone remembers their version, no matter if they go on to make $1,000 $100,000 or $100,000,000.

You just have to start.

My Definition of Innovation: Make Awesome Where Awesome Is Not

September 25, 2016

It was 2011, and I was on stage at Fast Company’s Innovation Uncensored event. I sat in the chair where Gary Vaynerchuk was supposed to be. Gary was the guest for this particular panel but his flight got delayed so the folks at Fast Company asked me if I’d be willing to slide up and fill his spot. You can imagine the audience’s disappointment, right?

On the spot, the moderator asked me what my definition of innovation was, and without giving it too much of a thought, I responded:

“Make awesome where awesome is not.”

I only remember this so vividly because it’s the same definition my wife still uses to this day (and repeats back to me in an effort to point out my occasional overuse of the word “awesome.”)

Now here’s why I think this definition matters, and especially why it might matter to you if you’ve had an idea brewing in your head for a while now but have yet to turn it into a reality…

Whether you have an idea that feels like it’s been done 100 times or whether you have an idea that feels so far-fetched it could only work on Elon Musk’s Mars, YOU are more than capable of innovation.

Let me explain.

Chances are, if you have an idea and you haven’t turned it into a reality yet, it fits into one of these two categories:

Category 1: You like this idea, but it feels like it’s never been done before, and that scares the shit out of you.

This is the category that most of my own projects have fallen under over the years. Whether it was getting paid to wear t-shirts for a living with my company IWearYourShirt back in 2009 (I donned t-shirts with logos and made YouTube videos before “YouTuber” was a widely accepted occupation); or selling my last name twice (auctioned off my last name for $45,500 to become Jason Headsetsdotcom in 2013 and again for $50,000 to become Jason Surfrapp in 2014); or making $75,000 on my first book, Creativity For Sale, by selling sponsorships at the bottom of every page (before I had written a single word of the book); for a while there, I had the market cornered on “business ideas that will make people laugh in your face.”

With every single one of these ideas, I asked my friends or family or close business peers what they thought, and with every single one, the majority of those people doubted I could make any money at all.

That’s the trouble with Category 1 ideas…

What hasn’t been done before (aka “where awesome is not”) is made up of equal parts endless possibility and raging disbelief.

But then, of course, you have Category 2.

Category 2: You like this idea, but it feels like it’s been done already, and that scares the shit out of you too!

Let’s take a second to talk about ideas “that have been done already,” shall we?

In 1996, two smart guys started working on a project together out of their garage. While this project was unique to them, and they were going to put their own twist on it, there were many other companies who had already created businesses in their specific niche – twelve of them in fact, a handful of which had become extremely popular and profitable.

But these two guys believed in themselves and saw an opportunity to do things differently. They knew they could add their own unique twist on an existing idea.

Maybe you already know that the guys I’m talking about are Larry Page and Sergey Brin, the founders of Google. But maybe you didn’t know that 12* other companies had already created search engines (many of them doing extremely well) before the idea for Google came to be.


Innovation Can And Will Scare You

In both idea-categories I mentioned, you have a tremendous opportunity to make awesome where awesome is not in this world.

Your opportunity for innovation gets taken away by never doing anything at all.

Innovation doesn’t just have to mean that you invent the technology that revolutionizes communication. It can also mean that you simply make something that didn’t exist before.

It could be that you find a way to monetize platforms that already exist like I did (in spite of those that don’t believe it can be done.) It could be that your version of “making awesome” isn’t necessarily in the what you make but in the how you make it, like Larry and Sergey figured out a way to do search in a way it hadn’t been done.

Whatever kind of idea you have though, the only way that your opportunity for innovation gets taken away is by never doing anything at all. By standing still. By letting that fear get the better of you.

Whether you’re starting a business and doing something that’s never been done before, or you’re twisting an existing idea into your own, the beginning will most likely be the hardest part.


3 Steps To Getting Your Innovative Idea Off The Ground

Here are the three things that have made the biggest difference for me in getting my ideas off the ground.

#1 Believing in yourself won’t bring you any guaranteed success, but it will help you get further along than most.

You could be building the next Instagram. You could be creating an online course. You could be writing your own book. You could be trying to get paid to wear t-shirts for a living.

No matter what you’re creating, if you don’t believe in yourself and your idea first, you’ll never reach any level of success.

Thankfully for me, this is a trait that I was born with. For as long as I can remember, even as a little kid sitting in a bedroom dreaming up ideas for comic book characters, I always looked at the world differently. There were times in my childhood when it became clear that doing things differently wasn’t the way to get ahead, especially in school. I was starting to pick up the fact that maybe being “smart” was a better way to navigate than being “different.” Boy am I glad I didn’t let those voices get to me because as it turns out, being smart isn’t the only thing that counts. Scoring well on tests isn’t the only thing that counts.

As long as you carry an unwavering belief in yourself and trust your gut when navigating those deep, dark, and uncertain waters of creating something unique or something that hasn’t been created before then you also have the power to help people see your vision of the world and what could be.

#2 You don’t get what you don’t ask for.

Every idea I’ve ever had has had one thing in common: I wanted to get XYZ thing, more than I feared what it took to get it.

That’s what sets people who make ideas happen apart from people who don’t, and that’s the very first reason any of my ideas go from thoughts swirling around in my head to viable businesses that create value and generate revenue.

Your original idea is nothing until you make the first version of it and then ask people to download it, buy it, or subscribe to it.

Until you make an ask, your idea is nothing more than a cartoon bird floating around in your mind. (And unfortunately, you can’t pay for lattes or your rent with cartoon birds in your mind.)

Ironically, being willing to make the ask is also what can help you overcome the self-doubt. The fear of the unknown is crippling: Will people hate my idea? Will they laugh at me?

Once you realize hearing “no” isn’t as bad as you thought (and it never is), you gain the ability to keep asking until you hear a “yes.” And let me tell you, all you need is one “yes” to stoke the flames of your own belief.

Your friends. Your customers. Your clients. Your shareholders. They’re not going to show up on your doorstep and throw yeses at you because you read this article or any other article on entrepreneurship, business, etc. But they will show up if you believe in yourself and you ask them to show up. It may not happen the first time. You may have to ask more times than you’re comfortable asking. You may have to modify your ask and change up who you’re asking, but if you want to achieve your dream more than you fear the reality to takes to get you there, your ask(s) will be rewarded.

#3 With patience, your bucket of appreciation will fill up.

Everyone wants happy customers with glowing testimonials to put on their websites or the back of their books right out of the gate, but it takes time to gain an appreciation for your ideas.

That’s probably why a lot of people never act on their ideas in the first place – not necessarily the fear that their idea will be met with rejection but the fear that people won’t even care at all.

Imagine that the gaping void of validation that you crave for your idea is in the shape of a bucket. A bucket of appreciation. The mistake most people make is forgetting to look at their buckets of appreciation in relation to where they are on their journey.

The day I launched IWearYourShirt, 12 people showed up to the website (and I’m pretty sure 5 of those were my Grama.) If I had been expecting a response that would fill a Grand Canyon-sized bucket of appreciation, I probably would have given up and shut the whole thing down that very day. I had the ability to see that I was just at the very beginning of the life of my idea, and those 12 people were enough to feel appreciated in a bucket the size of which matched the age of my idea.

Google didn’t start out as one of the most profitable companies in the world. They started out with a $100,000 check from their first investor (and a slightly upgraded garage). Sure, you may or may not be chasing $100,000 at the beginning stages of your idea like Google, but the point is that if you don’t appreciate your business or idea at every stage in its existence, you’re quickly going to overwhelm yourself with unrealistic expectations. Your bucket of appreciation will end up feeling too large, and any praise you do get will barely cover the bottom.

It’s important to dream big but also to match your expectations with your reality.

Instead, it’s important to match your expectations with your reality. Dream the big dream of creating the next Google if that’s your aim, but put your expectations in check with what your current circumstances are.

With patience, not only will you find the right people to fill up that bucket of appreciation that you’re so desperate for, but you’ll find that the size of your bucket will grow in proportion to the hard work you’re willing to put into your idea.

These are the ways that I’ve been able to make my own awesome, in my own way, for over a decade now as an entrepreneur, and I’m far from being done.


Here’s The Truth About Innovation And Sharing Your Ideas

I wrote this article because I hope you turn your current or next idea into a reality. I hope the cartoon bird version of it flies out of your mind and morphs into a first (actual) version that someone can pay for.

I hope that you stop looking at competition in whatever market you’re in as a hurdle, and instead, see it as proof that people are willing to pay for some version of your idea and as an opportunity to innovate in your own unique way. I hope you believe in yourself and channel that belief into the work it takes to receive the appreciation you’ll get if you make the asks (and then repeat that process over and over again).

I’ve been blown away by the appreciation of my ideas over the years, and I want the exact same thing for you.

I said it as an offhanded comment in 2011 and I’ll say it again:

All that innovation requires you to do is make awesome where awesome is not.

Let the making begin.

You Shouldn’t Do It

August 7, 2016

I love Nike’s slogan: Just do it. It’s a great motivator. There are lots of difficult things in life that you should do anyway. But for this article, I want to tell you why you shouldn’t do it.

And what’s “it?” Starting and running your own business.

You shouldn’t do it because it takes effort

Are you someone who loves the idea of putting your entire business on autopilot and automating everything? Yeah…first of all, best of luck with that. I know absolutely no one who runs a successful business that is completely automated. But secondly, the effort (read: the journey) should be the fun part. It has to be, actually, because the challenge is going to crush you otherwise. You’re going to work longer and harder than you ever have in your life, and the payoff is so far removed from “overnight success” that everyone who’s ever succeeded in business just laughs at that concept.

If you aren’t ready to invest countless hours and make big sacrifices in your life, you shouldn’t do it.

You shouldn’t do it because you’ll have to change everything

You can have the most ironclad and well-thought-out business plan of all time. You can have experience from previous businesses. You can have amazing mentors and maybe even a bunch of funding.

But you know what? Your plans will change. If you’re doing it right, your vision will be shaped and molded by what your customers are actually willing to pay for. Your plans will fall apart as quickly as you can say pivot.

If you’re allergic to change, you shouldn’t do it.

You shouldn’t do it because you’re not famous

You aren’t going to be the next Steve Jobs.

You aren’t going to be the next Elon Musk.

You aren’t going to be the next anyone.

You are going to be you. No one knows who you are, and that’s a really big hurdle in people’s minds. They’re not going to trust someone they don’t know, and it’s a lot of work to get people to both recognize and trust you. It’s an even bigger hurdle to do the work your business requires without the expectation of ever getting accolades for it.

If you’re hoping to see your name or your business’ name in lights someday, you shouldn’t do it.

You shouldn’t do it because you’re going to mess up

You are going to make mistakes. You are going to have to make tough decisions, and no one is going to be able to give you all the answers. All the advice in the world can’t help you when YOU have to be the one to make the tough call. And sometimes, you’re going to make the wrong one. It’s going to suck.

If you are afraid of failing often, and in public, you definitely shouldn’t do it.

You shouldn’t do it because you have a good thing going

You shouldn’t start your own business. You should keep your job and make the best of it you can. Enjoy every day of job security that you can soak up. Relish the idea that you know where your paycheck is coming from and that someone else has to make all the tough decisions.


If these things don’t scare you into hiding, then maybe you should do it.

Your Idea Isn’t Good Enough and How To Find A Good Idea

June 12, 2016

Wait, what? Is that contraction supposed to be there? Shouldn’t that have said your idea is good enough?


If your idea was good enough, you would pursue it. If your idea was good enough, you would carve out precious time for it. If your idea was good enough, it would keep you up at night and force you to work on it, hour after hour.

Let me be clear: I’m not saying your idea sucks. I’m not saying your idea is bad.

What I’m saying is that you’re resisting taking action with your idea. The reasons for resisting might be totally legitimate. Sometimes we’re just not ready, and that’s okay. Not being ready is okay.

Sometimes we’re TOO ready, and we get dangerously consumed by an idea. Some people’s ideas take control of their lives.

It can be scary to have an idea so powerful, or a job so demanding, that it ruins relationships and destroys your health.

Sounds drastic, right? How could a simple thing like an idea do that? Ask Mita Diran, the 24-year-old copywriter who died at her desk after spending 30 straight hours in the office. Consider the Japanese concept of karoshi, which translates as “death by overwork” and is estimated to claim 200 workers every year.

That’s not what we’re going for here. I don’t want you to swing from procrastination all the way to dangerous obsession.

The key is to find a comfortably challenging place between procrastination and obsession. A place that will empower you to get things done and still enjoy your life. To take action with your idea.

What would you create if money didn’t need to be involved?

What’s something you just feel you need to get out into the world? What is something you can’t stop thinking about?

We all have bills to pay, but we all also spend hours wasting time. Watching TV. Reading random articles on the Internet. Reading every book by Seth Godin. Scrolling through social media feed after social media feed. Every single person, myself included, has the extra time to create the thing we can’t stop thinking about.

You’ll know when your idea is good enough

How? You’ll stop having so much time to read articles like this one. You’ll fall behind on your favorite podcast. Heck, you may even miss hitting inbox zero for a few days/weeks.

But when your idea is good enough, it will demand your time. Not all of it, because your idea wants you to have a life, too. But a lot of your time. And when your idea is good enough, the time you invest will be rewarded.

There Are No Business Rules, So Have More Fun

May 29, 2016

For as long as men and women have walked upright, there has been some sort of commerce. Trading food, pelts, gold, goods for services, etc. Throughout it all, there is one common element that has secretly remained unchanged: there are no rules.

You may think there are rules, but look at our current reality as an example:

Tomorrow, I could buy a domain, put up a website, and sell a product or service—all without asking a single person for permission.

Even more interesting (to me, at least) is that I could sell whatever* I want to whomever I want. Used cereal boxes? Yep. A subscription service about the mating habits of chameleons? Sure. Snow? It’s been done. If you can dream it up, you can sell it, and no one can tell you no.

*Of course, I can’t sell drugs or anything that’s illegal. Stay with me here, and try not to poke a hole in this theory just because there are also no rules about criticism.

Another great non-rule about starting a business right now? You could make $100,000 tomorrow. It would be incredibly difficult to do, but the ability for that to happen is 100% possible. 50 years ago? Good luck.

But if there are no rules, why aren’t more of us having fun with our businesses?

I bet you can count on your fingers and toes the number of people you know who hate their jobs. You might even be one of them.

Why do we resign ourselves to doing work all the time that doesn’t bring us joy and happiness? Why do we subscribe to “rules” that don’t exist about how to work and live?

I’m not trying to paint a picture where everyone in society has a job they love. I know that’s only going to lead to people saying, “Who’s going to clean our toilets?” and “Do you think all the trash men/women have fun disposing of your garbage?” So let’s not go down that road (for now).

Let’s go down the road of making time and space for fun in our work. Time and space for making your own rules.

I don’t mean a corporate trip to Legoland to do team building and synergistic yoga exercises (…everyone get into downward-facing-demand-chain-economic-reporting). I mean allotting time for projects that have no immediate tangible benefit. Doing things that are a bit outlandish and may even veer into bizarre/crazy/what-the-hell-were-we-thinking spectrum.

Beautiful things happen when you stop following the rules.

Amazing discoveries are made when you’re willing to have some fun without limitations (revenue projections, legalese, etc). If every decision you make has to involve the bottom dollar, then I truly feel sorry for the way you run your business.


Fun In Business Has Unintended Outcomes

You know what people talk about? They talk about things being done differently. They talk about the weird things that pique their interest. They talk about memorable things. Not a single person goes and tells their friends about the amazing time they had doing downward-facing dog poses with the accounting team.

Trying to have fun can spur ideas.

Trying to have fun can land you press and attention.

Trying to have fun can do more for personal and team morale than any raise, bonus, or product launch.

I read an article recently by Ali Mese titled I can’t tell you why your business is growing. There was one point that stuck out for me:

“No matter how strong the temptation to obsess about conversions or short-term hacks, we need to understand that what lies behind sustainable growth is our ability to delight our customers with our dedication to extreme value creation.”

I strongly believe that adding a little fun here and there can (and will) delight your customers. Even if whatever fun thing you create isn’t something they can buy or have.

It’s nearly impossible to measure the ROI of fun. But not everything in business needs a measurable ROI.

What are some ways you can have fun with your business?

Make one day of the work week about exploration and play: Encourage your employees (or just yourself) to spend one day of the work week having fun and creating for the sake of creation.

Fun doesn’t need an ROI. Fun just needs to be fun!

Show and tell goes a long way: My friend Paul Jarvis and I set out to create a silly product in 24-hours called Emojibombs. By most people’s measurement that project was a failure (it didn’t make money and we shut it down fairly quickly thereafter). But, we saw it as a success because we got to engage our audience for a couple days, show them every stop of the process, and people still remember that project.

Build a tool or website that you’d enjoy: Similar to the Emojibombs example, build a tool or website that you’d love. Maybe it’s a how-to guide on DIY’ing your own saddle for corgis? Sounds super silly, but if you love dogs, you may make something that other dog owners would enjoy and share. You could also make something helpful, just remember to keep it fun!

Travel: As obvious as it sounds, there’s so much fun and discovery to be had by getting out of your comfort zone and routines. You don’t have to go somewhere extravagant either, odds are you have something fun and unique to check out just a few miles from where you currently sit.

Films some videos or a podcast: Creating content can be incredibly fun, especially when there are no business objectives behind it. Just create for creation sake and follow one of your passions. Don’t measure anything. Don’t look at the analytics. Just. Have. Fun.

Share your fun!

I would imagine most entrepreneurs and business owners don’t have fun for fear of what people will think.

What if I alienate a customer who thinks we don’t take our business seriously?

What if we show that we’re having fun and a big client thinks we just goof off all day?

What if YOU drew a line in the sand and were okay with embracing fun instead of working a few extra hours to try to make extra money?

In our current no-rules-in-business society, you get a badge of honor for working hard and hustling. What if instead of another honor badge, you went for some colorful flair (fun!)?

I’m up for having more fun and not worrying about it increasing my revenue. Are you ready to join me?