Louis CK turned down $500,000 a year from Conan in the early 90s so he could go broke instead. Conan wanted to hire him as head writer of his show.

Every step of the way, spanning 20 years, he put a challenge in front of himself that seemed impossible and it was until he passed it.

Now he’s the best comedian ever. One can argue with that, but one can argue about anything.

He was offered the job of head writer at one of the hottest comedy shows in the world. He would’ve grown from that and be set for life.

Instead he decided to hit the road. He went from gas station to comedy club to bowling alley to hotel to wherever to tell his hour of jokes.

He talks in one interview about he loved to perform at proms. “I would get booed by drunk teenagers even before I got on stage. If you can handle that you can handle anything.”

He was already one of the best comedians in the world already in 1997 when I first saw him perform.

But that wasn’t the end of it. In the mid 2000s, he made a radical transformation to his act. Inspired by one of his heroes / mentors, George Carlin, he did two things:

1. CONSTANT CHANGE.

He changed his act every year – “January 1, I had no material.” He would start from scratch. This is incredibly difficult to do.

To be honest, I don’t quite know how to do that with my writing although I try.

2. AUTHENTICITY.

He decided to leave behind the classic jokes of comedians (“What’s my ethnic background? Here’s how I make fun of it?”) and talk more about his personal life.

In 2010, I played some of Louis CK’s jokes to my kids. His jokes were then about how his kids basically suck. My children were horrified. “Isn’t he being mean? What do his kids think?”

But it was funny. They laughed.

And Louis CK doesn’t tell those jokes anymore. Every year they get better.

But that’s not all Louis CK did after he turned down the job for Conan.

3. MASTER EVERY ASPECT.

He also wrote a movie. It was crazy stupid wild. Pootie Tang. It’s a cult favorite. And everyone hates it. Watch it. It is completely insane. He directed, produced, and wrote it, getting experience from two different sides of the camera.

He also made an HBO show that got cancelled (starring not only Louis but also my prior podcast guest, Jim Norton). The HBO show was a direct insult to the then current form of TV production.

He also pitched a show to CBS, they rejected it. And he pitched a show to FX (they barely accepted it, giving him the lowest possible budget per show ever and he turned that into one of the most successful series on TV).

Before that he wrote on the Chris Rock show, getting experience in other forms of comedy.

4. UNDERSTAND THE BUSINESS SIDE.

I can keep going. Louis CK released on his website his comedy special even though any major network would’ve been happy to pay him for it. He made over 7 figures in a day.

Constantly experimenting: he worked on his art (listen to the way he does voices now versus 10 years ago, 20 years ago).

He worked on his authenticity. He challenged himself in ways that seemed impossible (coming up with an hour of material every year, it took Jerry Seinfeld 15 years to do that).

He wrote, he was a director, he was a producer, he created a TV show, he wrote for TV shows, he handled rejection, he created an e-commerce site, and he constantly expanded his rolodex and network.

He didn’t put in 10,000 hours. He put in 20,000 hours.

5. UNDERSTAND ALL THE SUBTLETIES.

Jonah Hill tells a story when he was on Howard Stern. Jonah Hill and Seth Rogen were in the movie Funny People playing stand-up comedians.

So they wanted to get experience as comedians. They did an open mic night at a local club. The Jonah Hill segment is on YouTube and is pretty funny.

But by coincidence, Louis CK was also performing there that night. So Seth and Jonah were terrified.

After the show Louis CK comes up to them. Jonah Hill was an academy award nominee and one of the funniest actors on the planet. Seth Rogen is a mega-comedy superstar in every movie (yes, even in the Green Hornet).

Louis CK said, “What, are you guys playing comedians or something and practicing for the role?”

Seth and Jonah said yes.

Louis CK said, “Ok.” He turned to Seth Rogen. “You did ok.”

He turned to Jonah Hill and said, “You need a lot of work.” Jonah Hill had never done stand up before. Seth Rogen had done some stand up as a kid (a clip of Rogen doing stand up as a 13-year-old is on YouTube).

Louis CK saw every subtlety.

We’re all born with a limited set of resources. Energy, intelligence, time, money. Louis CK could’ve taken that $500,000 a year job and kept improving from that point.

6. DELIBERATELY PUTTING CHALLENGES IN FRONT OF YOURSELF.

But 10,000 hours of work isn’t about improving. It’s about starting from a place of hunger, and going above and beyond the ceilings placed above you, and achieving mastery.

It’s about taking all the resources you have and investing completely in yourself so that you constantly have nothing to fall back on except your own ingenuity and success.

It’s about taking everything you have, emptying your “life bank account” and pouring it back into yourself. Looking for the “return on YOU” instead of the “return on investment.”

Louis kept starting from scratch and challenging himself to force himself to master some aspect of comedy he had never mastered before. To start from scratch:

at a job. Giving up $500,000 a year to have no job security forced him to up his skills enough to get paid on the road versus every other comic in the world.

at writing a movie

at writing comedy fresh every year

at being authentic and honest and not falling on the comedy standard used by other comedians

7. BREAKING BOUNDARIES

at starring in a TV show that broke boundaries (“Lucky Louie” took 70s style TV direction and brought it, unsuccessfully, into the 21st century).

at writing, producing, directing, starring in a new TV show with almost no budget.

at constantly hitting that gray area where he both insults the audience and gets the audience to love him (“can all the Jews leave now?” – Louis CK is part Jewish, part Mexican, part Boston, part other things).

because we are in an arena where the gatekeepers are dying, Louis CK made his own website the source of distribution when nobody in comedy had ever done that.

Study his comedy in the 80s, the mid 00s, now. See how he improves. How he constantly invested in himself. Do the same with another master: Jerry Seinfeld, and compare the different ways they improved. Louis CK has defined a new level of mastery in comedy.

8. FAILING

at failure. How many things has Louis Ck failed at? Writing a movie, two TV shows, probably numerous comedy events.

He was already one of the greats, but why did CBS reject him and FX barely accept him? How did he overcome this frustration when he was divorced, getting into his 40s, and having no prospects for success (he’s a high school dropout – this was IT for him).

He must have been scared? He must have had some despair on his chances. And then he did it.

9. BUILDING YOUR SCENE YOU ACHIEVE MASTERY WITH.

In the show Louie, which is semi-autobiographical, the main character (played by Louis CK) is watching a TV clip from the 80s and sees himself performing and Sarah Silverman performing.

He calls Sarah Silverman on the phone and they watch it together and are nostalgic for those years when they were so young and just starting out.

10. STUDYING THE HISTORY.

Comedy isn’t about telling jokes. It’s about observation. And studying the observation of all the observers before you.

From that moment on in the 80s, he invested in himself. He studied the history. He studied every comedian. He studied failure. He studied every aspect of the art. His “return on himself” was one million percent.

Not everyone needs to do that to feel a sense of success. I don’t think I’ve done it. But it’s beautiful to watch and appreciate it.

Louis CK is not my favorite because of a single joke or two.

He’s my favorite because he invested in himself and not the opinions of others. He invested in himself and not the gatekeepers.

I want to be like him when I grow up.