Say Yes To A Bigger Career

Most improvisers do improv as a hobby while they work a day job to pay their bills. Many wish that someday they could quit their day job and just do improv, but they can’t really figure out how to get there.

If you want to quit your day job or just make a little extra money in improv, you first have to start saying yes to artistic opportunities that come your way, even if  you never done them before. So if someone asks you to direct a sketch show, and you never done it before, give them a big fat yes, because it is in the realm of your art. On the other hand, if your roommate asks you to operate on his leg, that is a no.

The number one reason people say no to new opportunities is because they don't want to feel like a fraud. But by saying no, they miss out on learning a new skill, and the future opportunities (and potential new paycheck) that new skill could bring.  Most improvisers are perfectionists, which is not an asset, and unless they can do something perfectly they are often not interested in trying. I don't have to tell you, anyone who is great at something, sucked at it first.

This can be a hard concept for many improvisers to embrace, especially if they think they already know what they want to be successful at. I’ve often heard people say things like, “I only want to act,” or “I’m a writer,” or “I  only do short form.”

In the arts, if you limit what you do, you will limit what you make. Most successful artists in any field have to cobble together several different things to make a living, and you can’t do that when you pigeon-hole yourself. How may Hollywood actors end up directing, writing and producing? They diversify themselves to have many different skills, all while staying within their art.

I’ve heard that millionaires typically have six different revenue streams. And even if we’re never going to be millionaires, we can use the same concept for our careers. The more sources of revenue you have, the better chance you will be able to quit your day job. My income comes from teaching improv, doing private storytelling coaching, writing books, podcasting, performing shows and acting for the camera.

The Dream

When I started taking improv classes in Chicago in the late ’80s and early ’90s, my goal was simple: To get hired by Second City so I could be on Saturday Night Live. The way I saw it, the path was very narrow. All I wanted to do was act. I wanted to be rock star in the comedy world -- the next John Belushi, Bill Murray or Eddie Murphy. If any of my improviser friends even thought about teaching, directing, producing, or writing, we thought they were giving up on their dream. For me, it was acting or nothing.

By the time I was in my 30s, most of my friends had figured out that to be successful, they had to give up on their dreams of being in front of the camera in order to make a living in the comedy world. Many of them were moving to New York to write for Conan and SNL. For them, it seemed natural to go from being a comedy performer to a comedy writer, but not me for me. I was still holding on to the hope that I was going to make it as an actor. I wish I could have learned from their example, but unfortunately, I don’t work that way. I learn through pain, years of it.

For me, my dream had become a nightmare. By the time I was in my 40s, I was single, teaching one improv class a week and living off credit cards and spending a lot of time in my bathtub listening to Howard Stern. I was a starving artist who was on the verge of becoming a homeless one.

Then things started to change when I started to “yes" more.

Saying Yes

I was very familiar with saying “yes” on stage doing improv. The concept of “Yes, And…” is simple in improv. When you are on stage improvising, you want to say “yes, and…” to other people’s ideas and add something to it.

But when it came to work, I was not nearly as good at saying yes because I was very narrow-minded in what I thought I wanted to do. But finally, when I was in enough pain and desperation,  I started saying yes to more different kinds of work. And what do you know? The more I said yes to opportunities that came my way, the more work I got and the more money I made. I was becoming a Renaissance man for hire.

People started asking me if I could coach them in writing a screenplay, or direct their one-person show, or teach a podcast workshop. And I started saying yes, even though I had never done any of those things before and, frankly, didn’t think I had the confidence to pull them off.

But you know what? I said yes anyway, and I trusted that if I got in over my head, I could ask for help from other artists in my field. And 83% of the time I was better at it then I thought.

Four Star Comedy Festival

One of the biggest things I said yes to that I had never done before was to co-produce a comedy festival.

The idea came from my friend, Ben Capraro, who is filled with a lot of energy and passion for comedy. In December 2011, he told me about his idea of doing a one-day improv festival at Chicago’s iconic Navy Pier with a rather large budget (in improv dollars it seemed like millions). His idea was to have improv workshops during the day and then performances from four different improv groups in front of 300 people at night.

He wanted to know if I wanted to be a co-producer.

I had never produced something as big as The Four-Star Comedy Festival before. Even though I felt like fraud and suffered from a case of imposter syndrome, I kept saying yes, just to see where it would go, secretly hoping it would fall apart.

Thank God for my wife, Lauren. She kept saying “Shut up, and keep doing what’s in front of you.” Well, co-producing was in front of me, so I decided to do it, even though I felt I was over my head. We asked for a lot of help along the way and got it, and when we finally put the festival on in October 2012, it was a big success.

And when it was all over, I am glad I did it. It’s rare in improv comedy in Chicago to get paid as much as we paid the groups that night, and it’s even rarer to get paid as much as we did to produce the festival. And most importantly, by saying yes to this opportunity, even though I wasn’t sure I could do it, I gained more valuable skills that helped me to diversify.

Teaching Improv Online

One of my main revenue streams is teaching improv. I have been successfully filling my improv classes and workshops for the last 15 years. I have to market my ass off to do it, and I often worry that my classes won’t sell out, but usually they do.

But when the pandemic hit in March, I did not know what I was going to do. We could no longer meet safely in person, and I had a master-level class already filled. I kept pushing the start date back because I didn’t know how I was going to teach the class. I was panicking.

Second City had moved to teaching online, using Zoom, which is a video conferencing service, but I wasn’t sure I could do that. I was skeptical. I was resistant. I was terrified. Just ask Lauren.

So, before I could say yes, I started doing my research and started calling my friends who were already doing what I thought was impossible — teaching improv online.

Kevin Reome, who teaches at Second City, spent over an hour on the phone going over his lesson plan with me, and reassuring me that doing improv online was actually fun. Another teacher there, John Hildreth, gave me some advice and some games I could try online. The next day, Noah Gregoropoulos e-mailed me asking me if I would like to improv on Zoom with another old friend of mine, David Koechner.

Noah was going to teach his improv class online for DePaul University and wanted to get comfortable with the technology and record some scenes to show his class.

When I got the e-mail, I was like “Fuck you, Universe, for giving me such a clear sign.” So I said yes and tried it.

On Thursday, the three of us met on Zoom and Dave and I did a couple of scenes and they were solid. Noah recorded them and played them back to us. When I saw the quality of work that can be done on Zoom, I thought, “I can do this! It will not replace doing live shows or live classes, but it’s a great alternative right now.” It made me excited.

After that, I asked a couple of friends to do a practice session with me before my class on Monday and called Noah to help me with the technology part, which intimated the hell out of me.

By Monday, I was all in. I was scared as hell, but excited too. I taught my first online improv class to a group of very experienced improvisers, and I was impressed at how agile they were with the technology and how quickly they were able to adapt to the new medium. Their scene work was outstanding and they guided me  through the technology when I hit a bump.

When the class ended, a couple of people mentioned that they had been skeptical, but were really pleased with how it went.

“Me too,” I said. “Me too.”

I have been teaching on Zoom for six months now, and I continue to stay financially afloat even in these uncertain times -- all because I said “yes.”

Once you get good at saying “yes,” you will also have to learn to start saying “no.” Next week I will talk about how saying “no” is an important part of making money from you art, too.

Interested in trying a new approach to your improv? Check out Jimmy's Art of Slow Comedy Fall Intensive, happening Oct. 24-25. Only $129 if you register by Oct. 10! Sign up today!