Prepare to Fail

If there is one thing that is certain in improv, it’s that you are going to fail. Hopefully, you will continue to fail throughout your career, because in improv, if you don't give up, that failure eventually turns into success. No matter how hard you try to avoid it, you cannot have one with other. Unfortunately, that’s how it works in the arts.

For us to fail on a regular basis we must take risks. Most of us avoid taking risks because we are sacred that we will look stupid or be rejected, which in our minds computes to failure. So we live our lives protecting ourselves from any form of rejection. We play it safe.

That is why we would rather send an email than pick up the phone. It’s why we hide behind Facebook and Twitter instead of talking to people in person. It’s why we don't ask that person out on date. When we avoid taking risks, we are not living a life — we are in damage control.

But what if you could look at it a little differently? What if you could take a risk and actually embrace failing?

Because I’ve improvising for a long time, I’ve gotten pretty good at taking risks, both in the classroom as a teacher and on stage as a performer. Taking risks has become part of my DNA. But even though I’ve taken risks, I was never really comfortable with failing. Anytime I took a risk that didn’t turn out well, I’d beat myself up about it. Until two weeks ago.

On Super Bowl Sunday, John Hildreth and I trudged out in the cold Chicago weather to do our show to a very appreciative audience. We were joined by three great, old-school improvisers: Pat Musker, Scott Levy and Mark Czoske.

The first scene turned into a musical improv, which I am not very good at it and I sucked. My song did not make any sense, I had no idea what I was singing or saying. Thank God for the rest of the cast.

For me, improvising a song is an enormous risk, one I typically avoid. And this risk really ended in a bomb. But the miracle is that I wasn’t upset at myself that I failed. In fact, for one of the first times in my life, I was simply proud of myself for having taken a risk.

When the scene was over, I thought to myself, "Good! I took a risk and failed, and now I have an even better chance of succeeding tonight." Who was this guy? Where was the perfectionist ready to beat me up for making myself look so stupid?

I don't know, but he wasn't in the theater, that’s for sure.

Neither was the guy who usually has to over compensate for a bad start and puts pressure on himself to make up for his “so called” mistake.

Or the guy who is so filled with shame after a mistake that he stays stuck in the back line until the show is over.

Taking the risk at the top of the show had forced me out of my comfort zone, forcing me to do characters and play with energies I hadn’t before with the support of these really great improvisers. I felt free. The show was a blast. Was that the only so-called mistake I made? No way, I made plenty more. In one scene, I entered in accidentally and didn’t know if they wanted me to stay or go, so I was a bit lost and felt I might have screwed them up.

Regardless, I felt great after the show. I learned a lot that night. A.) That there is no such thing as a perfect show. Sure, we can shoot for it, but it does not exists. And B.) That even when you have a great show, there a lot of things you wish you had done differently.

I think the problem we all have in taking risks is that if it does not pay off immediately, we think we did something wrong. We then stop taking them on stage and even worse in life.

But what if we gave ourselves credit for just taking the freaking risk and trust that we will be rewarded later, just like in this show?

It’s really sad to think about all of the risks that I avoided taking throughout my career — like turning down an audition for Saturday Night Live, saying no to a TV writing job, or leaving or closing successful shows too soon — all because I was afraid of rejection. (My therapist may argue I was afraid of success).

I don’t feel regret that I didn’t get those things, but I do feel regret for not having the courage to experience failure, because the Universe always rewards you for taking a risk. Sometimes you are rewarded directly, and sometimes indirectly, but there is always a reward.

But the truth is, I did not see that until this last show. So now hopefully, I can pass this lesson down to my students, to my daughter and now to you.

Looking to take your improv to the next level? Sign up for Jimmy's Art of Slow Comedy Level 2 class, starting Feb. 28! (You don't need to have taken Level 1 to take this class). Early Bird pricing ends Feb. 14!