New York taught me to be willing to fail publicly

The celebration of storytelling that is Broadway, the Manhattan skyline framed by the Brooklyn Bridge, the clouds of potent weed smoke enveloping me like a forced hug- I was there to take it all in.

"This is the guy I’m here for", I told my brand new husband.

We had gotten lucky, and had snagged seats right in front of the mic at the Comedy Cellar on MacDougal Street in the stand-up capital of the world, New York City.

I was willing to get picked on at this hot seat, if that's what it took. All in.

Sam Morril was fourth in the line-up that night. The comedians before him had good sets, but I was eagerly anticipating Morril’s set. Edgy jokes, dark punchlines, deadpan delivery- bring it on. I was ready.

And then... he bombed.

What?

How could this be?

A professional comic with a Netflix special wasn’t able to make people who had paid to laugh on a Wednesday night, laugh.

I had seen all of his specials, so I knew he was good. Better than good. Effortless. Each of his specials has a few million views online, yet here he was, failing in a room of 150.

Wait- maybe that was the whole point. That it was a room of just 150.

He was trying new material- his jokes were edgier than usual, the punchlines were half-fleshed, and the delivery was undecided. Bombing in smaller rooms night after night is how he got to millions of views. Experimenting with new ideas, cutting out what didn’t work, perfecting the delivery.

Trying. 

Watching this act of bravery made me realize that I’m coasting. Not really trying.

I don’t ask questions unless they are perfectly framed, rehearse what I want to say in my head only to remain silent when the moment arrives, and almost never try anything new unless it is behind a screen.

At school, succeeding by doing seemingly nothing is what makes you cool. Anyone making an effort is “trying too hard”. In real life, making an effort is not just acceptable—it’s essential. Mastery comes from committing to the craft and putting in the reps.

But I was still taking pride in avoiding real effort because it felt safe—if I didn’t try, I couldn’t fail. 

If Sam Morril with his 737k followers could afford to fail, how was my army of 14 stopping me?

I used to think it’s because I’m not good enough. But maybe that’s not it. Maybe I just have an inflated sense of self that prefers to maintain an illusion of superiority over those willing to take risks and potentially stumble. Maybe my shyness isn’t a personality trait, but an unwillingness to fail publicly. 

Maybe shyness is a mask.

Oh crap. 

The good thing about a mask though is that I can take it off.

Whenever I want.

As we were walking back from the Comedy Cellar to our hotel, I saw the comics taking a break before they went in again, for the next show. He looked happy. He had crushed it, put in one more rep.

New York delivered.