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Do you remember how "dating" worked in fourth grade? I do.

I'd ask my friend to ask her friend to ask her if she would like me – hypothetically speaking – if I liked her.

It makes you chuckle, but it's not too different as an adult. Now, you use Tinder. You tell Tinder who you like, and Tinder tells you who likes you – but only if the feeling is mutual.

It's no different in art. When you feel scared to make your art, it's because you feel love, or affection, or lust for an idea. But, you're afraid of getting hurt.

What if you pursue it, and it rejects you? What if your chemistry experiment blows up in your face, or your startup pitch falls flat, or nobody reads your blog post?

Stuff like this hurts, but it's a part of making art. You have to be weary of when these fears cause you to hold yourself back.


Even though there is art inside you, and even though your true Self is pushing to get out, there is a force that's always there trying to hold it all in.

It does it because it wants things to stay the same. It wants to fit in. It wants to convey the prim and proper and obedient version of yourself to the world. It doesn't want your true Self to get out.

This force is the Ego. People often think of the Ego as being a source of arrogance. Really, that arrogance is just the Ego trying to reconcile what the Self feels, and the Self's conflict with what the outside world seems to want.


You see the conflict between the Ego and the Self in the posturing in entrepreneurship today. It's very common for budding entrepreneurs to use violent language to describe what they're up to. "Man, I'm killing it. I'm hustling."

They feel that the outside world wants to see them making lots of money. But inside, they don't feel like they're enough. Their true Selves would rather be exploring those feelings, but the Ego freaks out. The Ego is like "no, you've gotta fit in!" The result is an overcompensation.

Acting this way can help you motivate yourself, and making art can be so scary and hard that it's nearly impossible to not puff up your chest to motivate yourself once in awhile.

But in the long term, this just creates a big gap between the person you present yourself to be, and the true Self that you could actually become.

I think this is why, when a person gets too absorbed in what he thinks the outside world wants, people might call him "a shell of a human being." He might even feel like one.


I know I felt like a shell once. I had been living in Silicon Valley for a couple of years, working at startups that had raised millions of dollars.

Then, I started a startup of my own. I found a co-founder, and we built an app. Then, I never lined up a single investor meeting.

But, I still thought of myself as a Silicon Valley entrepreneur. It took me a long time to realize that I wasn't.

I didn't want to raise money. I didn't want to run a company with no business model in sight. I didn't want to manage a team.

I know now that I wouldn't be good at those things. It was never my calling.


The more you try to reach to be something you're not, the bigger and more vacuous your shell gets. This is why you might hear a person described as "vacuous," which originates from the latin "vacuus."

"Vacuus" is also the origin of "vacuum." If you had an actual dome-like shell (your Ego) over a mound (your Self), and the distance between that shell and that mound got bigger and bigger (whether because the mound was getting smaller, or the shell was getting bigger), then you'd have yourself a vacuum. If you punctured that shell, all of the air would escape, and it would collapse into a withered mass on the mound.

My shell was finally punctured when a woman I had been dating broke up with me. I think we've all dated someone well beyond the expiration date, and this was one of those cases. By the end of the conversation, I realized that it was much more than this relationship that wasn't a fit. It was my whole life.

So, I shut down my startup and left Silicon Valley. I rented a cheap apartment in Chicago's Ukrainian Village, and did everything I could to give myself time and space to explore what interested me. I needed to reconcile this conflict between my Self and my Ego. I had a lot of fixing to do.


During that time, I had a recurring vision in my mind. I pictured a mound of dirt, and my hands in the dirt, and even cleaning the dirt from under my fingernails to add it to the mound and make it a teeny tiny bit bigger.

I didn't want to reach anymore. I wanted to build upon that tiny mound, work with what I had, and what was natural and good to me, and maybe, just maybe someday that mound would become a hill – or maybe even a mountain.

Like anyone else, I'm still full of hot air from time-to-time, but the distance between my Self and my Ego is thinner and thinner. It's not easy to follow your art. Your Self experiences rejection, and judgement from others, and downright heartbreak.

To me, it's better than being delusional. We used to put several layers of people between ourselves and disappointment when we were asking out our classmates  on the playground. Most people protect themselves the same way in their work.

It's more comfortable to work where you can blame things that go wrong on a coworker, your boss, your boss's boss, or even The Board. When you're on your own, you quickly learn that only you are responsible for your own success or failure.

Sure, things might happen that aren't your fault. Your shipment of paint supplies are late, your sous chef calls in sick, or your server goes down. But whether or not it's your fault is irrelevant. You are responsible.


This is why the Ego is so quick to puff up. It provides a cushion between your Self and heartbreak. This is Law #3 of art: Your Ego fears your art.

Your Ego fears your art because if you follow your art, you will Self-actualize. You will become your true Self. But to do so, you will experience failure, and rejection, and heartbreak.

This is hard, but it's rewarding. You will finally know the truth. Your Ego wants to protect you from harm. That's why it's always protecting you: Telling you it's not your fault, that you should blame others, or that you should just play it safe.


There's a format to almost every great story called "the hero's journey." The hero receives a "call:" He needs to get revenge on the man who killed his father, or she needs to convince the board she's the right CEO. The story is the hero pursuing that call.

But for the story to be interesting, the hero has to reject the call. This is easy, because we're always rejecting what's calling us.

Walter White of the TV series Breaking Bad received various calls, and the storyline of the series is driven by the rejection, and acceptance, of those calls. First, he gets diagnosed with cancer – a call. He sits down with his family and tells them he's not going to get treatment – a rejection of the call. His Ego is rightfully scared of the rigors of treatment.

One morning he wakes up alone in bed. He's smelling his wife's pillow, and her lotion on the nightstand. She's in the kitchen doing dishes. He embraces her, and tells her he'll get the treatment. His Self has broken through the fear of his Ego, to accept the call.

Because Walter can't afford the treatment, he's driven into manufacturing methamphetamine. After his first experience killing a man – an experience also woven of rejections and acceptances – he decides he's through. Later, when he's at the hardware store, he comes across a couple of guys who are clearly buying supplies to make meth. This triggers rage within him, and challenges his sense of manhood. He walks out into the parking lot and confronts the men. "Stay out of my territory." At this point, he accepts the call of drug manufacturing.

Walter White was actually an "anti-hero," and his nefarious actions in Breaking Bad were apparently driven by his feelings of inadequacy, exacerbated by an ex-business partner and an ex-lover. I don't mean to illustrate that you should become a meth manufacturer. I mean to illustrate that the tension between the Ego and the Self makes for great stories.


We all are heroes in our own stories, and we all experience tension between the Ego and the Self. We all reject our calls. But many of us reject the call, and never answer it. We never become our true selves. We never Self-actualize.

We give up our dream of becoming a stunt car driver to choose a safer career, we put our box of paints away and let it collect dust, or we sit down to write our novel once every six months – then eventually never again.

Sometimes you have to decide that a dream of yours is just not a priority. The author, Malcolm Gladwell, mentioned in his interview on The Tim Ferriss Show making a conscious decision to quit running track in high school, because it would take energy away from other things. But if you aren't decisive about abandoning a dream, the tension between the Ego and the Self remains because the call has not been answered.


So, now you know the forces that control the pursuit of your art. There is art inside you. It's your calling to bring that work into the world, and Self-actualize. But, your Ego will try to protect you from the inevitable discomfort that will follow.

How can you possibly face that discomfort? It's not simply a matter of sucking it up, of swallowing the bitter medicine. You can make it manageable, and increase your odds of triumphing. That's what the rest of this book is for.


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