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How to Be Yourself

There’s nothing inherently wrong with run-of-the-mill businesses. But this guide isn’t for those types of businesses. It’s for unique businesses that don’t fit neatly into boxes. Run by unique people who don’t fit neatly i boxes

That previous sentence (fragment) is important. That’s why it’s bold. Duh.

Crazy, one-of-a-kind businesses aren’t run by boring people. Nor are they run by people who don’t know what they want. Nor by people who are too afraid to be themselves. (And in Chapter 4 we’ll talk about how they’re not run by fat slobs either.)

And perhaps most importantly, running a successful businesses depends entirely on your definition of success.

Are you successful if you net seven figures but you hate your life? Unless you have a messed up definition of success, no.

This chapter will help you find yourself, be comfortable being that self, and try to instill in you a non-messed up definition of success.

Here we go.

What do you want?

Such a simple question. Yet how much time do any of us spend truly thinking about it? You might be tempted to brush this off as some hippy-dippy nonsense. But that would be dumb. Bypass this question and you might spend the next 25 years chasing a lofty business dream that you don't actually care about.

Or to a much less dramatic end, you might spend the next year building a Facebook following only to realize that you don't want a Facebook following.

We need to get past what you think you want. Past what you think you're supposed to want. And all the way to what you want.

This is a hell of a difficult question to answer. At least it was for me. It takes time and it takes some vulnerability. But at least beginning to think about this is a prerequisite for the rest of this guide. Because until you can get a grip on the answer the rest of this guide (and every other guide) is going to be pointless.

What does your perfect life look like?

“What does your perfect day look like” is the more common question. But if all of my days were the same I’d be miserable. And I’m sure you would be, too.

So... what’s the answer?

You’re not alone if the answer doesn’t jump out at you. We’ve spent such a dominant percentage of our lives focused on getting good grades, getting into a good school, rising in an esteemed career, and having a healthy retirement account at the age of 67 that most of us never stopped to consider if all of that is really what we want.

The goal here isn’t to bash the status quo for its being the status quo. That seems to be getting more and more common in the digital era, but for what reason? If you prefer Nickelback, that’s cool. If you prefer Random Underground Band, that’s equally cool. But if you actually prefer Nickelback but say you prefer Random Underground Band, then you’re just a tool. (Though preferring Tool is unrelated, and also cool.)

All of that is to say that there is no right or wrong answer to what you want. Want what you want. Be okay with it. And move along.

My perfect life is one where I’m able to spend multiple hours outside each day. One where I have enough money that I’m able to go skiing, rock climbing, and vacationing as much as I want without stressing about the expense, and also to eat top-quality food without stressing about the expense. My perfect life also involves immersing myself in a constant stream of new solvable problems, and solving them. It involves spending lots of offline time with people that make me happy and that I can make happy.

But that’s not something that I was able to figure out in five minutes. That took me several days - completely free of the Internet and of any world obligations - of deliberately thinking about that question and writing down whatever popped into my head, no matter how idiotic. And maybe or maybe not some intoxicants.

My perfect life cliche. That’s because a lot of people say that’s what they want their life to look like. But how many people actually work toward that life?

Actions speak louder than words. It’s easy to say that money isn’t the ruler of your life. Actually, for that matter, it’s easy to live it, too. You just have to get started.

What are you “passionate” about?

The answer to this doesn’t have to be what you think it has to be. You don’t have to be passionate about sports, or safe cars, or accountability software, or social media, or blogging. That’s totally cool if you are passionate about any of those things, but there’s nothing wrong with you if you aren’t.

I’m “passionate” about trying new things, figuring out the ins and outs of those new things, getting really good at them, and then moving on to something else. There are things wrong with me, for sure, but they are unrelated to my “passion” or lack thereof.

It’s easy to believe that we need to be passionate about one specific niche. But if we believe that, falsely, - just because we think we should - then we are setting ourselves up for failure.

What happens if you build a sports website because you incorrectly think that your passion is sports? I did this very thing one time, so I can tell you exactly what happens. Your interest in the project fizzles out. Pretty soon you realize that you weren’t actually passionate about sports, but rather you had a honeymoon crush on sports very similar to the one you had on Melissa in 7th grade. And then you’re stuck doing something you don’t feel like doing.

If you agree with my logic so far then you might think that we’re all doomed to a destiny of running websites that we don’t care about. But I’m here to save you from this doomsday feel free to imagine me with a superhero cape on right now.

If you are passionate about a niche, lucky you. Your path is pretty straightforward. But if you’re more like me, and you’re passionate about variety, then the key is to accept that passion and not to fight it.

For me this means that I don’t take on projects that are going to take me more than a few months to execute. I know myself. I know that my enthusiasm will fizzle if I go beyond that. So I’m honest with myself, and I stay within my boundaries.

It means that I’ve stopped blogging, and instead have turned to writing guides (like this one) and online books. I know first hand that if I try to blog about X then I’ll eventually get bored and stop doing it. But if I instead write a book about X then I have a concrete end point already established. Writing guides and books does take a little more upfront cognitive energy as you have to strategically plan out how all of the pieces will fit together. But the result is a single coherent body of work, and that’s well worth the tradeoff.

If you feel like your back is in a corner, turn around. There are almost certainly some creative ways that you can do what you want to do every day. You just have to take the time to figure them out, and then you have to be okay with the fact that those ways might not fall in line with’s Top 10 Ways to Run a Business.

What do you do?

What does running your business involve? What do you do to make it all tick?

There are (very few) things you have to do, or find someone else to do, like filing your business taxes. But most things are optional, even if we don’t realize it.

You don’t have to have a Twitter account or a Facebook account. You don’t have to blog or build an email list. You don’t have to offer opt-in incentives or have exit-intent popups.

Those are all things that every online business “guru” blows his or her load over. But you are not every business, so you do not need to listen to every business “guru” (which is a term that requires quotes). You do not need to have their loads blown on you.

I’m not promising that it will be easy to make millions of dollars if you skip any or all of those things. There are several things that perhaps you should do if your sole goal is to make money. But it’s unlikely that your sole goal is to make money.

Let X be equal to something you hate doing.

How much are the benefits of X worth to you? How much are the benefits of not doing X worth to you? Act accordingly.

How do you do it?

I write like I’m talking to my best friend. When I talk to said best friend I occasionally use some crude language. So my writing occasionally has some crude language.

This is important. The crudity itself isn’t important, but the fact that I type the same way I talk is important. Once I begin filtering out certain words it’s a slippery slope to the bottom of a hill in which I no longer have a unique voice. And that’s a one way ticket to yawnsville.

My occasional crudity isn’t a sign of disrespect. I will not use potty language in front of your mother (unless she uses it first). But this is my domain, and on my domain I will do what I want to do, how I want to do it.

How do you do business? Is it how you truly want to? If I were to meet you in real life and then read your blog (not that you need one), would I think that it’s the same person talking?

If not, we have a problem. As a potential fan it’s going to be hard for me to fall in love with you if I never get the chance to see the real you.

Your solopreneur business is not a billion-dollar multinational empire. You do not have to remain neutral on everything. Understand your values and don’t compromise on them (unless they suck).

What is success?

If you successfully answered the “what do you want” question then you already know success. Success is what you want. Nothing more. That was easy. Moving on.

Are you self-conscious?

Running a unique business sometimes means being bold and pushing boundaries. But what if you’re scared to be bold and push boundaries?

Fear not, because we’re all self-conscious. It’s just a matter of to what degree, and of whether or not it cripples us.

I’m self-conscious. And that’s precisely the reason I like doing things like walking around with no shirt on. The Vitamin D is a toasty side-benefit, no doubt. But the main benefit is that it conditions me to stop giving so much of a hoot.

Having people stare at you judgingly is not fun. But it gets less and less not fun as time goes on. And then one day you realize that not many people were actually staring at you. You were inventing it.

Obviously there are some things that you avoid because they're inconsiderate. And as a fellow planet-inhabitor, I appreciate you refraining from those things. But you also avoid some things purely out of self consciousness.

If you're doing - or not doing - things only to avoid judgement, then you're not living your life. And if you're not living your life then you sure as hell are not going to be able to run an outside-the-box creative business.

Some people aren't going to like the way you run your business. You need to be strong enough to tell those people, at least in your head, to go blow themselves. Your business is going to be run however you want it to be run. Because it's yours. And you're the boss.

Do you think of yourself as someone who pushes boundaries? Then start pushing.

How? The upcoming section about creativity should give you plenty of ideas. Do any of those “embarassing” things and you’ll be on your way.

Do you stifle your creativity?

Part of being a creative entrepreneur is being creative. Astute observation, I know.

Fortunately creativity isn’t something that can be toggled on and off like Airplane Mode. I say fortunately because if this weren’t the case then everybody would be creative. Which would mean that nobody would be creative. Or something like that. At the very least it would mean that we’d all have a much harder time standing out.

We live in a time where creative freedom is at an all-time high, but creative thought (on average) is at an all-time low. This is because creativity doesn’t just happen. It must be allowed to happen. And very few of us allow it.

The best way I’ve found to foster creativity is with a two-pronged attack of childishness and boredom.

Being Childish

When’s the last time you climbed a tree, built a sandcastle, had a water balloon fight, did a cartwheel, ran around barefoot, or built a pillow fort?

Hopefully “earlier today” is your answer. But it’s probably not. Are you too good for these things? Are you too “mature” for these things?

I hope not, because being childish improves your brain, your body, and your spirit.


Childish activities stimulate your brain in ways that it’s not used to being stimulated. Throwing a water balloon is freaking weird. It bends around your hand as you try to propel it forward, and your brain is like WTF?!? But in a good way.

The more (unique) problems your brain solves, the more agile it becomes, and the better it’s able to solve other problems. Figuring out how to do a cartwheel without face-planting will help with that blog post that you’ve been struggling to finish for the past three days.

Which is cool, because it’s a never-ending excuse to have fun. The next time your spouse walks in and sees you doing a handstand you can say “I’m working, honey.”


If you are like most people your daily exercise is either (sadly) nothing or it’s (perhaps even more sadly - stay tuned for Chapter 4) cardio.

Maybe you’ve kicked it up a notch and you also do some pushups and pull-ups. That’s great. And maybe you’ve kicked it up another notch and you also do some squats and deadlifts. That’s really great. But, no matter how many exercises you incorporate into your routine, you will never hit all of your muscles.

Unless you incorporate childishness.

What happens when you rake leaves, shovel snow, go skiing, play basketball, or go hiking? You are sore as hell for the next couple of days, right? That’s because you just worked muscles that aren’t used to being worked.

Every time you climb a tree (they’re all different), throw a water balloon, jump over a fence, or do a summersault you’re working a whole slew of muscles that most people never work. You are undoing musculature imbalances that most people never undo. And you are drastically decreasing your chance of injury as you age.

So yeah, being childish is good for your body. Which, as we’ll discuss in Chapter 4, is good for your business.


If you build a pillow fort you are going to have a good time. You’re going to giggle incessantly. No, not laugh, but giggle.

25 minutes later you start writing the copy for your new landing page, and the copy turns out to not only be hilarious, but also warm and welcoming. Because you just built a freaking pillow fort. You’re glowing, and that glow is easy to see in your writing.

Your refreshing copy is the reason people sign up for your site instead of signing up for your competitor’s site. And therefore the reason your site takes off instead of fluttering.

This is the reason you often hear the common phrase “Businesses are built one pillow fort at a time.”

Being Bored

When’s the last time you were bored for more than 45 seconds, excluding showering and pooping? Probably the last time you had a water balloon fight, around 6-7 years ago.

Actually, nobody even poops in peace anymore. The shower is the last escape. And the shower thoughts subreddit just so happens to be the one with the most creative thoughts. Is this a coincidence? No, it is not.

Don’t get me wrong: I understand this constant connection. Obviously the world would not function properly if someone had to leave you a voicemail, if the finale of The Bachelor got spoiled for you, or if someone had to wait more than 12 minutes for you to respond to her Tweet. Hashtag sike.

In a world where busyness, no matter how unproductive, is perceived as worthiness, staring blankly at a screen is socially (and often economically) rewarded. But often times taking an hour of secluded silence to think about a problem, and nothing more, is the most productive thing you can do. But it doesn’t look productive. And it’s not comfortable. So we don’t do it.

Luckily, since if you’re reading this you probably work for yourself (at least on the side), you don’t have to bend to those social pressures of busyness. You can spend your time actually getting stuff done, not pretending to get stuff done.

The next time you come across a business problem that you’re having a tough time hurdling, I dare you to go into the forest for an hour with nothing but a notebook and a pen and not make progress on the problem. You will fail miserably at the dare. But you will win at problem-solving.

Chapter in review.

If you were looking for a quick fix then you probably didn’t want to read this chapter. If I had to, I’d guess that you wanted to read Chapters 2, 3, 6, and 7, the chapters that help you make and sell things.

But not giving you the quick fix was a deliberate decision. This guide includes tips for growing your audience, but it’s not about growing your audience. It’s about the totality of running a creative online business without it compromising your personal life. And, like it or not, this chapter is a required part of that totality.

This chapter exists to plant a seed in your brain. You’re not going to figure out all of life’s deep questions today. Don’t worry about that. That’s not the point. Just keep all of this stuff in mind as we move forward. That way when we talk about how to grow your email list later in the course, you can stop and ask yourself whether or not you want an email list. Maybe you don’t, and that’s okay. But even if you do, which is most likely the case, the simple act of questioning will reinforce your desire to build an email list, and will make you that much more committed to it.

See you soon.