In April, I dipped my toes into the frightful waters of stand-up comedy by enrolling in a 6-week level 1 class at Manhattan Comedy School. Last month I performed my first set at a major NYC comedy club. Tomorrow, I’m performing in a new talent showcase.

Every time I go to get on stage, I have a little pang of what was I thinking? I love this feeling of discomfort that tells me I’m on my edge.

Here’s what I am LOVING about doing stand-up comedy, and what I am learning from doing it.

Being Myself Without Apology

For most of my life, I have been trapped by the expectation of what I need to say or be or wear or look like or do to attract clients or potential partners. I have been imprisoned in the belief that when I step out into the world I represent my family or my business or my company or my religion.

(Yes, in high school we were told that wherever we went we represented the entire Jewish people).

Talk about pressure to succeed.

In the world of comedy, that goes out the window.

This is the place where the only way to win is to show up as yourself. In fact, the more of your natural personality you can being, the more people can relate to you.

I get to release all expectations that others have of me, or that I have of myself.

It’s liberating.

Freedom to Fail

The system is built on failure.

You’re going to bomb. You will fall flat. You will suck.

Everyone does.

In comedy, you work out your content in public. This is the only way to know what works. Nobody knows what will work in front of a crowd until they put it in front of a crowd.

Nobody.

The biggest names in comedy still go to the clubs to work out new material because the only way to know what works is to test it in front of a real audience.

What I’m learning is that all I need to do is show up. Obviously, I have to write the jokes. But there’s no way to show up with perfect jokes. First, because no joke is perfect. Second, because the only way a joke gets better is when you tell it to people and then listen to the feedback.

I can try things many different ways. Even if I don’t hit it all (or any of it), that’s ok. In fact, it’s the point.

There is complete freedom to fail.

Think about that. Would you even know how to handle it? I’m only starting to realize the magnitude of this.

Honestly I LOVE this so much. Like I’m actually mad I didn’t get into this earlier in my life.

Success vs Failure

In the world of entrepreneurship and personal development everyone talks about the freedoms that come with success.

I am realizing we have it all wrong.

Success begets imposter syndrome, golden handcuffs, perfectionism, and higher expectations. It traps us in a myth of who we must be and what we must do to maintain our status

If you want freedom, embrace failure. Chase failure. Failure offers you the opportunity to reinvent yourself again tomorrow, to try something in a new way, to experiment with a new approach. Failure gives you a lens for fresh perspectives.

There is no greater freedom than the freedom to fail.