How to Fail Early and Often

Photo credit: John Karpinsky

If you want to learn something about dealing with failure, try to do some improvisational acting. Because when you act, you fail a lot. On stage. In front of everyone.

During summer weekends, I am part of the cast of the Bristol Renaissance Faire, an outdoor theater near Kenosha, Wisconsin. The Faire is a recreation of Bristol, England, in 1574. Faire guests pay $25.95 to immerse themselves in a world that recreates the sights, sounds, and smells of a Renaissance-era village. There are stage shows, shops, restaurants, and actors dressed up in period garb walking around to play with visitors.

I portray a character named Nicolas Wright, and my friend Kendall Monaghan plays Dandy Goodwell. We are two of the characters guests meet in the streets. In essence, the Bristol streets are our stage. Our job is to engage with people quickly and figure out how to uplift them through improvised talking and joking that usually lasts a few minutes per encounter.

Photo credit: Denise Beidler Bennorth

We do this kind of street improv all day, from 10 a.m. to 7:30 p.m. And we are good at it. We know how to read people and find a way to engage them with our improvised comedic bits. People are asking us all the time how we do it. Well, we’re good because we fail a lot and learn from failure.

Photo credit: John Karpinksy

When you meet and greet people all day in an outdoor theater, you’re going to mess up. You’re going to make a joke that falls flat. You might approach a Mom just when she’s distracted with a fussy child. Or maybe you’ll forget the name of someone you met 5 minutes ago. This is the nature of street improv.

One recent weekend, Kendall and I really screwed up. We wanted to stage a water balloon toss with some patrons on a particularly hot day. We thought the idea was brilliant. Who wouldn’t want to play catch with a water balloon and see it splash all over dusty streets?

We chose a heavily trafficked spot in the park and placed several water balloons on the ground. Then we called out to different patrons. Would they like to have a water balloon toss?

Guess what: no one cared. In clusters of two, three, and four, the patrons just kept walking past us like we didn’t exist. Every once in a while, we might convince someone to stop and play, but it was obvious they were bored out of their skulls. It didn’t help that the balloons never broke, and everyone’s aim sucked, leading to several moments where one of us needed to stop, scurry off, and retrieve a rolling water balloon.

We called an end to the toss after about 5 minutes, which seemed like five years. Here’s what we did next:

  • We went backstage and had a good laugh. Could you believe how bad we bombed? we asked each other. And how about the 20-something dude who looked like he was ready to doze off in the middle of the balloon toss? Could we have failed any more spectacularly?
  • We figured out what we needed to fix. We realized we’d made two crucial mistakes: first, we’d chosen a location near the entrance of the park. Well, when people are just walking through the front gates, they don’t want to stop and play with two actors in 16th Century garb. They’ve usually decided to go see one of the stage acts or the joust, and they are focused on walking to their destination. We were a distraction to their day, not a source of fun. And, second, we tried too hard to get people to play with us. We were like the desperate kid brother and sister who beg everyone to play. We were too needy.

Based on our analysis of what we did wrong, we adapted our approach. We chose a spot where people tend to tarry a bit and take in the day. We carried out our water balloons in big reproductions of 16h Century military shields for a little visual theater. And then we started tossing the balloons at each other without asking anyone to participate.

As it turns out, when people see two people playing and having fun, something happens: they stop eating their turkey legs and watch. They become curious. What’s going on? What’s up with the flying water balloons? And some of them want to join in.

Within a few minutes, patrons just started naturally picking up the balloons we’d set on the ground. We formed a circle and started tossing water balloons until one of us dropped them, leading to laughter when the balloons splattered on the grass. Sounds kind of silly, right? Well, when you’re dressed up in a funny costume, something as mundane as a water balloon toss seems amusing to other people.

Photo credit: John Karpinsky

The bit worked so well that we repeated it over a few weekends. Then we experimented with a watermelon toss, which really went over well. A water balloon splattering on the grass is funny. A watermelon exploding all over the place is spectacular.

Success!

The key to dealing with failure: we laughed. We owned the failure. But we learned and got better.

How do you bounce back from public failures?