SSS #65: 5 Lessons From Jerry Seinfeld


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5 Lessons From Jerry Seinfeld

I totally missed the boat on Jerry Seinfeld. I’m aware he’s a creative genius, but I never found myself in a position to enjoy his work.

I know he headlined a crazy popular sitcom back in the 90s, but it didn’t catch my eye.

I remember him being the voice of a bee in a mega-hit animated movie, but I was likely pretending to be “too cool to watch that”.

More recently, I caught a trailer of his show on Netflix: Comedians in Cars Getting Coffee. He got Obama? OK, this dude is legit.

So after a lifetime of regretfully missing out on the legend that is Jerry Seinfeld, I decided to watch his Netflix Stand Up Special 23 Hours to Kill.


Because I’m obsessed with personal development and every self-help book and blog out there often refers to the “Seinfeld Strategy”. You know, the one where you have to do something (like write a joke) every single day. The only rule is you can’t miss two days in a row.



When I realized Jerry was the guest on Episode #485 of The Tim Ferriss Show, I downloaded it immediately and sat down at my laptop to take some notes.

Finally, a chance to learn from someone I knew I respected, but didn’t really know why.

You can listen to the episode here:

Or you can read my notes below and get the gist of a 90 minute interview in 10 minutes or less.

Lesson 1: Use Analogies to Make the Esoteric More Relatable

When Jerry first started stand up comedy, he described it as a “completely hermetically sealed world that is, frankly, unrelated to the rest of the entertainment industry. It is really unrelated to almost all the other creative arts”.

Stand up comedy is foreign to almost everyone. We might enjoy a show here and there and know the names of some of the greats, but practically none of us know what it’s like to get on stage and tell a joke.

He manages to explain the nuances of being a comedian with a ton of analogies, most of which are about sports, animals, and vehicles.

There were 3 analogies Jerry used in the episode that made me appreciate what he was talking about a little bit more than I would have if he didn’t use them.

1. Jerry compared the different categories of comedic arts to vessels on the water. He says...

Movies are like yachts. Everyone thinks yachts are the ultimate way to go across the water because they’re beautiful, expensive, and there’s a lot of people involved.

TV shows are like boats. They’re much less expensive and you only need a few friends on board to really enjoy the experience.

Standup is like a surfboard. It’s just you. You paddle out and try to catch a wave. After that you come back home. Nobody really knows what happened out there except you.

2. When you have a creative gift, it’s like someone just gifted you a horse. He says...

If you’re gifted a black stallion (utmost creativity), you must learn how to ride it. Otherwise it will throw you off its back and trample you. There are many examples of creative geniuses who go crazy, get depressed, or don’t fit into society because they never learn how to ride their horse.

*cough* Kanye *cough*

3. A 60 Minute Show = 9 innings

Jerry compares a 60 minute stand up set to a full baseball game. Anything shorter than 60 minutes is Busch League. If you get a gig for a full hour, that’s a complete game where you take the crowd through a full rotation a few times.

These great analogies make me wonder: how can I use analogies to explain esoteric ideas in the world of real estate, business, and personal finance? Sometimes spitting out facts and numbers don’t do the trick.

Lesson 2: Use Positive Constraints & Rewards To Create Systems & Habits

Jerry says his writing sessions used to be arduous and painful. “It was like pushing against the wind in soft, muddy ground with a wheelbarrow full of bricks”.

But he had to do it to succeed because stand up comedy is more about being a writer than it is about making people laugh.

So how did he make his writing sessions more enjoyable? By treating his brain like a puppy.

He says the brain is a stupid little dog you have to train with repetition, positive constraints, and incentives.

You’ve got to control what your brain can take.

You don’t sit down to write for an undetermined amount of time whenever you want. Nor do you workout for an undetermined amount of time whenever you want.

You need to come up with a simple system that has positive constraints. If an hour long workout is too long, try 30 minutes. If a 15 minute meditation session is too long, try 10. Start with something you know you can do.

The reward is the timer hitting 00:00. That’s when you can stop.

Lesson 3: Learn to Accept Your Mediocrity

No one is naturally great at anything. The people that typically rise to the level of greatness are the people that just put a tremendous amount of hours into their craft.

Writing (or any skill) is not a game of talent, it’s a game of tonnage.

Lesson 4: Scaffolding To Mitigate Depression

Jerry believes depression is a small part of the creative kit. He doesn’t know a single creative person that doesn’t have a tendency to feel depressed every now and then.

With that said, he prefers natural remedies over chemical interventions (drugs), depending on the severity, of course.

Jerry claims the combination of weight-training and Transcendental Meditation can solve just about anyone’s life.

Weight-training is the stress inducing activity that builds the resilience of your nervous system.

Transcendental Meditation is the stress relieving activity that also helps energy recovery and defer concentration fatigue.

Lesson 5: Your Failures Are Your Most Valuable Experiences

Jerry tells the story about moving from New York to LA at 25 years old. He had been doing comedy for 4 years and felt it was time to move up to the Major Leagues.

The Comedy Store was THE stage to be on in LA, but Jerry could never get a spot. He called the owner, Mitzi Shore, and asked for an in-person meeting. In that meeting, Mitzi stepped on Jerry’s ego by saying she’d never give him a spot.

His resentment towards her lead him to:

  • Start performing in discos
  • Go from writing 3 days per week to 7 days per week
  • Get on the tonight show, which ultimately catapulted him into stardom

If you ever have to rank your experiences, put your failures at the top of the list.

Is This Anything?

In October of 2020, Jerry Seinfeld released his first book in 25 years, titled: Is This Anything?

It’s a curated collection of his favorite material since his start back in 1975.

If you’re like me and totally missed the bulk of his career, but ultimately respect him as an artist, it might be worth picking up the book.

Link: Is This Anything by Jerry Seinfeld