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I was trying to cheer someone up. “The sun feels nice,” I said.

“I don’t even notice those things,” he said.

My friend was depressed. But I thought I could help.

They say you can’t make everybody happy. But really, you can’t make anybody happy.

I know this. But it doesn’t always stop me from trying.

Six months ago, I did my first stand-up show. Now I have a new experiment. I take one photo a day. And I tell a story.

But I haven’t stopped thinking about stand-up. And I want to get better.

So I interviewed Gary Gulman. He’s one of my favorite comedians. Top two. Him and Louis C.K.

I’ll throw Amy Schumer into the mix. Top three.

Gary started 23 years ago. And I’ve watched his Netflix special, “It’s About Time” twice (so far).

The best way to learn anything is to study the masters.

Studying Gary taught me there are three steps to developing talent in anything:

Step 1: Start somewhere

Gary first tried stand-up in 1993. But that’s not how he got started.

Before that, he watched comedy. He repeated jokes to friends and got laughs. That’s how all successes start. You just do it for fun.

That’s how Derek Sivers started CD Baby and how AirBnB began. They were experiments.

Gary only had five minutes on stage.

“Back then I did impressions,” he said.

He did one of Seinfeld and Kramer playing basketball.

But “within a year, I had decided my impressions were not very good.”

That’s step 2: Evolve.

Doubt is a leader. It can take you away from what you don’t love and into what you do love.

“That’s how I got on the track I’m on now,” he says.

If you’re “good,” you’ll just sit back. And someone who’s no good will get better.

  • They’ll get a mentor
  • They’ll reinvent themselves
  • They’ll practice for 10,000+ hours
  • They build a love for it

If the “good” ones don’t evolve, they’ll remain just that… good.

Step 3: Tell your story

“I have symptoms of depression,” he said. “I almost feel like I’m moving in slow motion. There doesn’t seem to be any amount of sleep that satisfies me.”

I can’t sugar coat it. It sounds miserable. But it’s also the source of his comedy.

“I guess if I didn’t have a depressive view of the world, I wouldn’t have the premises to go off,” he said.

“But at the same time, if I didn’t have the depressive nature, I would have more confidence and more energy to write more and maybe expand into more acting or podcasting or writing a book.”

It’s a balance.

“On the days you get out of it, how do you get yourself out of it?” I asked.

There was a long pause.

“Or have you never gotten out of it?” I asked.

I wanted to find out what works for him.

And it came back to helping people.

“Stand-up comedy gave me a lot of reward,” he said, “as far as making people feel a little bit better and forgetting about their problems for a short time.”

He turns pain into humor, which morphs back into pain.

That pain becomes a bit. And that bit becomes a laugh.

You can’t make people happy. But if you tell your story, maybe you can make them laugh.

Resources and Links:

Also mentioned:

  • Gary’s favorite comedians:
  • Gary’s book recommendation for people interested in comedy: “True Story: A Novel” by Bill Maher
  • Gary’s favorite comedy-related documentaries: