The Punchline I Almost Never Found
What stand-up comedy taught me about perfectionism
“Perfectionism kills curiosity by telling us that we have
to know everything or we risk looking ‘less than.’”
-Brené Brown, Atlas of the Heart
For over a decade, I did stand-up comedy.
I started in Montana, driving hundreds of miles across the Western states to perform at a different bar or hotel lounge each night. Road comedy. Eventually, I moved to New York City to try to earn my stripes as a club comic. I took one of the first classes offered at the Comedy Cellar and started hitting open mics.
Comedy became my second language.
It also became the place where my perfectionism felt most at home.
Yellow Legal Pads
My process looked like this: I’d write jokes longhand on yellow legal pads. Write them, cross them out, rewrite them. When a joke started to feel close, I’d tear out the page and tape it to my bedroom wall.
Then I’d stand in front of it and practice out loud. Over and over, adjusting words and tightening the rhythm, until every beat felt right.
Only then would I take it to an open mic. Some jokes took months.
I told myself this was discipline. High standards and respect for the craft. And some of it was. Good comedy does require precision. Timing matters. Word choice matters. A single syllable can be the difference between a laugh and silence.
But somewhere along the way, the preparation stopped being about the work and started being about the control. If I could get the joke perfect on paper, I wouldn’t have to risk it falling apart on stage.
Five Minutes at Gotham
Two years after moving to NYC, I got a spot at Gotham Comedy Club.
It was a bringer showcase, which meant I had to bring a certain number of audience members just to get five minutes of stage time. Five minutes. Every second counts.
That night, something shifted. I knew my material cold. Every word, every pause, every beat. But instead of running through my mental script the way I usually did, I let it go. I stopped worrying about whether every line would land exactly the way I’d rehearsed it in my bedroom.
I just stepped onto the stage.
Towards the end of the set, I got to a bit about my love of cheese. It had one joke I’d been working on for a while, testing different punchlines, trying to find the right one. I had a version I’d been performing. It was fine. It worked.
But that night, standing in the lights at Gotham with the audience already with me, I threw out the punch line I’d been rehearsing and tried something simpler. One word instead of a full sentence.
The room erupted. And I did something that took me years to learn. I shut up and rode the wave. Time slows down when a room is fully with you. I could read every face, feel exactly when to push and when to wait. That performance got me invited back for more sets.
And I never would have found it on a yellow legal pad.
The Perfectionism Trap
Brené Brown has spent over twenty years studying what keeps people stuck. She names the trap precisely: perfectionism kills curiosity. It tells us that mistakes are personal defects, so we either avoid trying new things or barely recover when we inevitably fall short.
I lived that pattern for years on those legal pads, rewriting jokes until they felt safe enough to perform. The preparation looked like professionalism. But I wasn’t trying to be great. I was trying not to fail.
And the cost of that? I wasn’t curious on stage. I was careful. Every set was a test I was trying not to bomb, instead of a conversation I was trying to have.
The night at Gotham, I stopped being careful. Not because I was brave, but because I was present enough to trust myself in the moment. It’s what gives you the chance to find a punch line you’d never have written in your bedroom at 2 AM.
The Coordinate: Grow Curiously
In the ENOUGH Compass, Grow Curiously means your path unfolds through exploration, not optimization.
Growth doesn’t come from perfecting what you already know. It comes from trying what you haven’t figured out yet.
Ask yourself:
Where am I perfecting something instead of testing it?
What would I try if I weren’t waiting to feel ready?
What The Culture of More Gets Wrong
We treat perfectionism like a virtue. A sign that we care more than everyone else.
Scarcity says: it has to be perfect before it counts. Keep refining. Keep rehearsing. The world will judge you for anything less than flawless.
Sufficiency says: good enough is the starting line. Start before you’re ready and trust that you’ll find what you need along the way.
The best comedians know this. You don’t find your voice by writing in isolation. You find it by getting on stage before you feel ready and listening to what comes back.
A Small Practice
This week, notice where perfectionism is disguising itself as preparation.
Where are you rewriting instead of sending?
Rehearsing instead of starting?
Waiting for the “right” version instead of testing the one you have?
Give yourself permission to try the version that feels 80% ready. The last 20% might show up on its own. Or it might not matter as much as you thought.
See you next week.
P.S. What’s something you’ve been perfecting instead of starting? What would happen if you tried it before it felt ready?