When I was 22, I decided I was going to take a real shot at writing and publishing a book. I had no idea what a never-ending series of humiliations was heading my way.

I’m a firm believer in the positive power of delusion.

I had been writing little stories since I was a kid, but this was the first time that I was going to try to write out my science fiction novel and submit it to publishers. If I knew how little I knew, I don’t know if would have had the will to start. …

Fresh out of college, I listened to a few Tim Ferriss podcasts. I decided it was my dream to move to Austin, Texas, and work for a start-up.

With what my mentor referred to as “chutzpah,” I waltzed into the scene with only my degree in philosophy and a big mouth. The next few years were spent navigating a failing business and the resulting personalities. I learned more doing this than college ever taught me.

Mid-twenties are hard for all of us, right? 3 years into start-up life, I fell on hard times when my girlfriend dumped me. After doing…

When I was born, the doctor told my mother, “He had his umbilical cord wrapped around his neck and tied in a knot. Good thing he is a serene baby — otherwise, he would have hung and starved himself.”

Shocking bedside manner aside, I love this story. My mom still tells it. Recently, I was thinking about how much I’ve changed since I was that baby.

I thought… Maybe I don’t need to struggle toward my writing goals? What if the struggling is the exact thing hanging and choking me?

Minimum Possible Force

There’s a Taoist principle called Wu Wei. …

I’m not a clickbait hater. There is an art to making your headlines enticing. But there is a high cost to only making your headlines enticing.

When I was a kid, there was a local firefighter who ran for Mayor. To secure more votes, he switched his political party. His wife, his close friends, and his kids all encouraged him to do it. What did he care?

He won the race by a tiny margin. The plan seemed to work! He celebrated and gave a speech later that night at the Town Hall. He hedged his position in the speech…

The only chance we have to win the game is hitting a home run. The other team is bigger and stronger. It’s little-league baseball, and I’m watching in the dugout.

The pitcher is a kid named Benny. He throws the ball so hard that you can see tears of pain in his eyes from home plate. We’re all afraid of the legendary Benny.

My friend goes up to bat. He’s a terrible batter and the most scared of Benny. On the first pitch, he closes his eyes and swings wildly. Strike.

On the second pitch, he steadies himself. He swings…

Earning a living from creativity might as well be impossible. But some people do it. For the last decade, my obsession has been — how?

I’ve written a novel, worked with successful and unsuccessful entrepreneurs, am an entrepreneur myself, pitched pilots in Hollywood, and met famous people who lasted and those who didn’t. They all seem so different…what unites them?

There are common attributes to creatives who make it — and last. It took me a long time to understand them. Hopefully, you can skip the line and steal what I’ve learned.

1. You Are a Rare Mixture of Playful and Disciplined

Some people are born more playful, some people…

When my start-up in Austin was looking to promote my co-worker or me — they didn’t look at our degrees.

Thank God because I drank myself to death in a state school and had a degree in the humanities. He had a master’s degree from Carnegie Mellon.

They promoted me because I could speak and write.

Schools Teach Obedience, Not Power

If they wanted to empower you, they’d teach you to speak and write. Those are the most deadly skills for any profession you can think of. Instead, they teach you to sit in neat rows and memorize text. …

My best friend from middle school was on fire. I watched him carefully. When I caught on fire a moment later, I knew how to put out the flames because I had watched him. “This is it!” I thought, feeling like a winner. “I’m finally going to be able to succeed in life!” Just then, the entire dream collapsed into a white line like a 50’s TV turning off. I couldn’t move and somehow I knew I had failed.

2 days later, I was driving to the park. “I should have put him out!” I yelled. …