Improv Nerd with Lyndsay Hailey

The risk of taking risks

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You hear this all the time in your improv classes – you need to take more risks on stage. But what improv teachers forget to tell you is that when you take risks, you’re going to feel feelings: anger, sadness, anxiety, fear, shame and, in rare cases, joy. This is a by-product of taking risks, and the quicker you accept this, the quicker you will increase your chances of taking more of them in your life and on stage.

If you take a risk and feel shame afterwards, like “Oh man, I went too far,” don’t assume that means you did something wrong. You will feel uncomfortable because you did something different, not because it was necessarily “bad.”

In fact, the one thing I can tell you for sure is if you are taking risks, you are always succeeding, even if it may not feel like it, because it’s the practice of taking them that really counts, not the results.

Last Sunday I was interviewing Lyndsay Hailey for Improv Nerd. She was so honest and revealing, talking about sensitive subjects like being sexually abused when she was a kid, her adrenal fatigue syndrome and her dating struggles. Lyndsay was taking huge risks, and if she knew it or not, she was inspiring me to join her. That’s how it works.

Towards the end of the interview, I asked her about her current boyfriend, and she started to answer the question and then interrupted herself and said “He’s in the audience.” So I asked him to come up on stage. The audience gasped, and the message in my head was, “You are going too far.” But I lucked out that he also was an improviser, and I’m sure he appreciated the extra stage time.

“What’s going on with the relationship?” I asked. The audience gave me an even louder gasp than first one, and I think: “Shit, why didn’t I play it safe?”

Everyone in the audience was uncomfortable, including me. I got the sense from her boyfriend’s answer that he was ambivalent about his relationship with Lyndsay. So I asked him if they had sex too soon in the relationship. At this point, my producer, Ben Capraro, was so uncomfortable he had to leave the room.

I was lost at sea. Lyndsay’s boyfriend diffused the situation with a joke, and then she said she was grateful her boyfriend had been around while she was uncovering her past with sexual abuse. Finally I felt like could see land in the distance, thank god, and I focused back on Lyndsay for the rest of the interview.

When I got off stage I felt excited. The show was everything I had envisioned Improv Nerd to be: vulnerable, real, edgy. It certainly was a different show than I normally do, and I didn’t get the usual “Great show!” comments I have come to expect from the audience, and because of that, I was confused.

On the ride home, my wife, Lauren, said “I bet you’re high from the show?”

“Actually, I’m not,” I said, like a little league right fielder who dropped the routine fly ball to lose the championship game.

I was filled with fear, shame, sadness and anxiety. I began second guessing my instinct to bring Lyndsay’s boyfriend up on stage. Never trust your feelings in this case. You could be feeling them for a million reasons, and one of them might be that it actually paid off. You cannot measure your risks by whether or not they “succeed,” only by the frequency that you take them.

Sometimes risks do not pay off immediately, and sometimes the results of taking a risk come weeks later, in another show or another audition, or in your life.

The important thing is to keep taking them, and you’ll know that if you are having feelings afterward, you’ve hit gold.

3 replies
  1. Pete
    Pete says:

    Jimmy, I love your interview style and the way you take risks and ask the difficult or left-of-field questions. Not just “what happened” but “how did that affect you”. I think it allows your guest to be vulnerable and honest, even though it’s an improv show and the instinct might be to go for comedy.

    The Lyndsay Hailey interview sounds amazing and I can’t wait to hear it.

    Reply
  2. Deborah J.
    Deborah J. says:

    😆 well written my friend. A golden egg award to you. I missed seeing you both tonight. Grateful and much love to you both over the holiday.

    Reply

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