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!


What I’ve Learned from John Hildreth

Sunday, Nov. 3 will mark the eighth anniversary of the Jimmy and Johnnie show. For the last eight years, on the first Sunday of the month John Hildreth and I and at least one special guest have improvised together. And the experience has really been a blast.

I can’t even take credit for the show’s beginning. John had been a guest on Improv Nerd and my producer at the time, Ben Capraro, suggested John and I should put a show on together. So John took the ball and ran with it. Originally Jimmy, Johnnie and Jet with Jet Eveleth. Jet moved to LA shortly after that, but we decided to continue doing the show and just find a guest to sit in with us each week.

When we started, I wasn’t very good. I was rusty and tentative and was having a hard time improvising again. I was putting too much pressure on myself, thinking, “I’d better be brilliant. I have been doing this for 25 years.”

It also took me a while to figure out how John played. Though we both are from the same generation of improvisers in Chicago, we had never performed together before. He was a Cardiff Giant guy, which was great bunch of improvisers out of the University of Chicago who always were very smart players and very character-based. I was more of an iO and Jazz Freddy guy, meaning I play very grounded scenes and am more trained to find the game in the scene. Even back when we were in our 20s, those two worlds didn’t collide.

So, as John and I performed together, it slowly became fun again to improvise, though it did not come overnight.

Today, with Jimmy and Johnnie, I get to play with some of the best improvisers in the city, and John is one of the best that I’ve ever played with.

The thing that’s so incredible about John is he always starts a scene with a strong point of view. And he does so organically. He gets it from a tiny little thing that someone says in the scene in the first couple of seconds. Then he keeps heightening the shit out of it until it’s super exaggerated and funny. It’s fun to watch and even better to improvise with. I have asked John hundreds of times how he does this, and I have never gotten an answer. It’s not that he doesn’t want to tell me, I think he just takes it for granted.

He is also up for trying new forms, even if they fall flat in the show. I am more cautious, but John wants to keep learning and keep pushing himself.

The other thing I admire about John is that he is very inclusive. We always have an opening act, typically former students of his or mine, and John is warm and friendly to them and it has become a tradition for us to take a selfie with our opening act and our special guest. This kind of inclusivety and camaraderie really inspires me and reminds me that we are all part of one big improv family.

Performing with John over the last eight years has really helped me become a better improviser. First of all, John’s energy and most of his choices are more positive than the dark-cloud, negative ones I like to play. And I’m happy to say that his positivity has been rubbing off on me.

I am also taking more risks and making bolder choices. I am more confident and relaxed on stage and yes, I would even say enjoying it.

I think a huge part of that comes from trust, not only trusting John as a performer and a person, but also trusting his talent. Every time I play with John, I know that he will be consistently funny. He’s one of those rare people who gets a laugh from the very first the first thing that comes out of his mouth. When we first started improvising together, I think I was more competitive with him and I wanted to be as funny or funnier than he was. But when I realized that wasn’t possible, I just started to relax and have more fun.

So on the eve of my next improv anniversary with John, I’d like to say thank you, John, for making me a better improviser. I’ve been honored to work with you over the past eight years, and here’s to many more.

The One Thing To Make You a Better Improviser

If you have been improvising for a while, you may start to get on autopilot when it comes time to doing shows. (I know I do). You get into the habit of rushing to the theater or bar, barely making your call time and then throwing your body on stage. When it’s all over, you wonder, “Am I getting any better at this?”

And if you want to keep getting better, you have to keep learning. That doesn’t mean you have to keep taking classes. It just means you have to find a way to keep pushing yourself to try new things.

So, I’d like to share this with you something that has worked for me and some of the groups I’ve played with over the years to help us continue to get better. It’s so simple, I’m almost embarrassed to tell you. Here you go:

Before each and every show, gather your team up and decide as a group on ONE thing you are going to focus on during that show. That is it: ONE. You can focus on something like doing bigger characters, or more agreement, or heightening, editing etc. But just pick one. Anything more than ONE will put you in your head and cause you not to have fun, which, as you know, is the poison that kills improv.

Keep the discussion short. It’s not a let’s-rehash-our-last-show-session. Avoid blame and criticizing. Keep it simple. Say something like, “Tonight let’s focus on letting our scene develop before we do walk-ons or edits.” Done. Since it’s a group, other people will have other ideas, so let them flow, and then quickly come to an agreement as a group about what you will focus on. That is it. Do not over complicate it.

With the more experienced or mature groups that I have performed with, this conversation takes a matter of minutes. Now before I continue, for those who think this is planning or cheating, let me reassure you it’s not. It’s simply a way to make sure we keep growing and developing as a group and as performers. It’s called learning.

Before every Jimmy and Johnnie show, John Hildreth and I will run down the show with our guest and briefly discuss the ONE thing we’d like to focus on for that show. Lately, it has been quicker editing. Before that it was doing more of a variety of characters, or being more physical, or using the environment. Here is the thing: If the group has been improvising for a long time, you know what you need to work on instinctually.

Doing this has helped my improv immeasurably because it continues to challenge me and get me out of my comfort zone. Focusing on ONE thing keeps me out of my head, since I have something else to focus on besides my own performance. It makes me feel more connected to my group because we are all working toward a common goal. And in a weird way, it makes me more open, honest and less defensive in the notes session afterwards and encourages me to tell on myself, which always leads to more learning and makes me a better improviser.

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Beware of the buzz kill

Beware of the buzz kill. That person who is in your group or in your class who takes a perfectly good show or class and shits all over it. They do it with their words. They do it with their negativity. Have pity on them; they don’t know any better. I should know, I am that person. I am the buzz kill.

That is how I am wired. It is a character defect. I cannot let myself have too much fun in my life – and that’s especially true when I improvise. It is as if my thermostat can only go to 62 degrees, and when I try to go higher and am having a great time, a mechanism kicks in and tries to regulate it. I open my mouth and try to find something wrong. The more fun I have, the harder I have to work to find something to regulate the temperature. But I will always find it. I am a professional.

It happened last night, after an incredibly fun show with two people I love improvising with: John Hildreth and Jay Sukow. I am so grateful that I get to work with them. They are both so filled with talent and positivity that I am hoping some of it rubs off on me.

After a show of 45 minutes of pure bliss, John and Jay look like two teenage boys at an amusement park who just got off the roller coaster and want to get back in line to go on it again. I am the dark looming cloud. We go back stage. The excitement is still in the air and on their faces, and I say, “I think we could be more focused in our warm ups before the show, instead of talking about Second City we could spend the last 5 to 10 minutes before we go on stage focusing on what we want to do in the show.” God help me.

The thing about buzz kills is they are usually smart, respected and rationale people. Like myself. They are so noble in their efforts and so full of shit at the time. So their points can make sense, but no one really wants to hear them at that moment, since everyone is still having a great time. The buzz kill’s goal is to have you join them in their misery.

We had a quick, thoughtful discussion on how we would warm up next time. And during that conversation here is the best part: I caught myself. “You know what? I am a buzz kill,” I said. “When I have too much fun I look for something to bring it down.”

I was proud of myself for saying that because you know what? I don’t want to be like that anymore. I really don’t. I actually hate that about myself, I do.

I have been doing this my whole life and believe me, it’s not just with improv.

People say we can use the concepts we learn in improv and apply them to our everyday life, but I believe the opposite is also true. There are things about myself that only become obvious to me before, during or after improvising and one thing is clear, I am a buzz kill and I really don’t want to be that person in the group any more. Who does?


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