4 Things You Need to Help You Take More Risks

Risk. When we think about taking a risk we usually think about disaster. We certainly don’t think about succeeding on the first try.

That’s how I used to think. I thought risks were supposed to be painful. I assumed taking a risk meant I would fail miserably and the learning would be in the doing and the lessons would come later down the road.

Risk never seemed to result in immediate success, until last Sunday night.

John Hildreth and I were doing our show, Jimmy and Johnnie, with our special guest, Dee Ryan. John has a long history with Dee going back to the ’90s at Second City and I have gotten to get to know her even better over the last four or five years playing with us. We are all the same generation and there is a lot of mutual respect and trust among ourselves, which it makes it easier to take risks.

Dee had been talking before the show about a form she had done at the Chicago Dramatic Improv Festival with Joe Bill and Dave Razowksy. It was called a Chekhov, after the playwright. Essentially, it’s a mono scene set in one location and the improvisers play one character the whole time with a lot of entrances and exits.

So we decided to try it. Dee explained that it would start with one of us having a conversation with an audience member to get information to inspire us the mono scene. We decide we would try it with the three of us in chairs instead of one, for more support. To end the piece we were supposed to bring the chairs back up and finish the conversation with the audience member. This would bookend the form.

I was both afraid and excited. Sometimes it’s fun to try new things, when I am in the mood. And that night, I was in the mood.

John always seems much more open to trying new things than I do, which I appreciate, but I’m really proud that all of us were open to trying something new that night.

The show went better than I expected. Not only was it really funny, but it was well received from the audience. I felt like we accomplished something as a group. It was satisfying, and I like playing a little slower and more emotionally than we normally play.

It was a success the first time out of the gate. What the fuck? That’s not supposed to happen. And it did. I felt great.

On the car ride home, I thought about how I look at taking risks as learning by failing.

The idea that you could take a risk on stage and have it payoff instantly was a new concept to me. Even though I am sure it has happened to be many times before, it was the first time I was aware of it.

Maybe my negative outlook life has clouded me all these years, but it was great to try something and have it work out so well. It got me thinking of all the things we have done right over the years that allowed us to take such a big risk. Here’s what I came up with:

  1. Find People to Play With Whom You Trust
    It’s always easier to take risks with people you trust. I have seen this in my classes all the time — the risks students take on the first day of class versus the last day of class are much different, since over the course of the class they have built a level of trust. My overall trust was in John and Dee’s ability and talent, and I knew that regardless of what happened, we could pull off an entertaining show for the audience. So to take risks on stage, make sure you find people you can trust to play with. It usually takes time to find the right people, so have some patience. When you find them, your work will blossom.
  2. Don’t Have Any Expectations
    This is hard, especially when you are doing a show in front of a paying audience where you would like to get a lot of laughs and be admired as the greatest improviser ever. I think part of the reason it felt like such a huge success to me is because I’ve learned that when I try something new, I  lower my expectations, and I knew there was a good chance this might not be a killer show. And when it is a killer show, it’s even that much better.
  3. Don’t Do It Alone
    There was something powerful in committing to take a risk before the show started. It made me feel like we had each other’s backs more than I normally do on stage. In a strange way, it gave me more freedom to make mistakes and take some chances that I normally don’t take because we are on the same page about figuring out together.
  1. Know You Are Never Going To Do It Perfectly
    Having a show go well is better than having a show that goes perfectly. There is no such thing as going perfectly. For example, even though I thought we nailed the form the first time out, we forgot to bring the chairs up and end the form with a conversation with an audience member. So what. This did not take away from what we did, and it reminded me that, “it’s about progress not perfection.”

Want to embrace taking risks? Sign up for Jimmy’s Intro to the Art of Slow Comedy Improv Workshop on Jan. 25! Sign up today!


Being Open to Learning

If you want to get better at your art, you have to constantly stay open to learning.

This has not always come easily for me. After a couple of years of improv classes, I thought I had it all figured out. I was done with classes. I was more interested in the results than in getting better.

But a true artist (and I know plenty) never stops learning.

Today, as old as I am and as big as my ego can be at times, I am grateful that I do a pretty good job at staying opening to learning.

I would even say that learning brings me joy. And if you have been reading this blog for some time, you know joy does not come easy for me, either.

When it comes to learning, this weekend was a big deal for me. On Saturday I re-opened my one person show, “World’s Greatest Dad(?),” and it went extremely well. The show and my performance keeps getting stronger because I willing to learn.

For this run, I am working with stand-up comedian Dave Maher. Dave is about 20 years younger than I am, but I wanted to work with him because he had put up a successful one-person show called “The Coma Show” about him waking up from a coma. I also like his style of comedy, so despite the age difference, I decided to give him a call.

We’ve been working together for several weeks, rehearsing and tightening the show. He is smart, funny and gives honest feedback. He’s given me writing notes, performance notes and helped me with the show’s structure. Working with him has been really fun, and I’m so grateful for all of the help. Now I just need to slow down a little and pause for the laughs a little more.

Then on Sunday, was the 8th anniversary show of Jimmy and Johnnie, and our special guest was TJ Jagodowski. I have always learned by watching TJ improvise, and I learn even faster when I am lucky enough to play with him.

TJ’s and John Hildreth’s approach to improv is similar — they can organically find a point of view for character in a scene in a matter of seconds and just heighten the shit out of it. This is something I struggle with since I am more reactive in my improv.

As an improviser, TJ always plays at the top of his character’s intelligence, he always responds honestly, and he always brings a sense of playfulness to his improvisation. This can be ego-deflating or inspiring, or a little of both.

When I play with him, it can be easy to fall into the trap of comparing myself to him, but when I do that and tell myself I’m shit, I block myself from learning. Instead, I try to approach playing with TJ as if I’m in a grad school class for improv, and remember that playing with someone who is better than me can only make me better, too.

I am grateful today that I am able to keep learning from these artists and don’t have to leave Chicago to do so.

Are you a seasoned improviser looking to get out of a rut? Don’t miss Jimmy’s Advanced Two-Person Scene Tune-Up on Jan. 4! Sign up today!

The Best Way to Get Out Of Your Comfort Zone

Improv is collaboration. That is why we do it, because we love to collaborate with other people. But when you have been improvising for a while, you can get set in your ways. You can start to feel comfortable only playing a certain style of improv or playing only with certain people.

I know this works for some people, but for me, it’s important to play with people who have a slightly different style than I do to ease me out of my comfort zone.

That is why I enjoy playing with John Hildreth in Jimmy and Johnnie. Although we are from the same generation of improvisers in Chicago, our approaches to the work are very different.

The guy is a genius. I am constantly trying to figure out how John comes up with a point of view so quickly at the top of every scene. I typically work slower, and I’m more serious. John brings a lot more silliness and boldness to his improv, which helps me get out of my improv rut. That is what can make it fun.

Each month, we also invite different guests to play with us, and each of them plays a different style. Though it can be scary to play with different people all of the time, it can also be fun.

Recently, we played with Thomas Kelly and Michael Brunlieb from one of the best improv groups in Chicago, Sand. They are quicker and more absurd in their play than I am, and they really know how to have fun on stage — three things I still need to work on in my improv.

I was blown out my comfort zone like with a stick of dynamite from the first scenes. The pace of the show was like a runaway freight train. It was exciting, but because I don’t usually play absurd, I spent a lot of time trying to stay on the same page with everyone. Some of the time I succeed and sometimes I was confused, and I am sure I confused them. It was terrifying and fun all at the same. I am looking forward to having them back.

When someone plays differently than we do, it’s easy to judge their style of playing and to want to look down on them. And it’s natural to want to find others who have a similar artistic sense to you to want to form a group with.

But that doesn’t mean we shouldn’t ever play with people who have different styles. Having new experiences on stage or off should be part of every improviser’s homework. That is how we grow and get better.

So, if you always play silly, maybe you should find someone who plays slow and serious to play with and see how that feels. If you only play long form, try short form. If you typically play really angry characters, find someone who can help lighten you up. You can go to an open improv jam to play with new people, or you can invite a special guest to join you in your regular show.

However you can make yourself more open to other ideas can only help you. Let me know how it goes.

Want to make improv as easy as having a conversation? Don’t miss Jimmy’s next Intro to the Art of Slow Comedy Workshop on Oct. 13!


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