My Improv Journey Through The Decades

I have been improvising and teaching improv for the last four decades. I don't know what has changed more: improv or me. But since the year is coming to a close, I thought it was a good time to reflect back on the past, so I wanted to go through the decades with you. Are you ready?

My 20s (1982-1994)

When I first started out in my 20s, I was consumed by improv. I was taking classes, doing shows. I was close to 300 lbs. and was drinking too much, as a result of hanging out at the bar before, during, and after said shows.

People still thought improv was stand-up comedy then, since there was no “Whose Line Is It Anyway?” I, of course, thought I was a better improviser than I really was. I was full of myself. When my family and friends would come to my shows, they would say things like: “Is this supposed to be funny or was it just over our heads?” and I just thought they didn’t get it. My friends who weren’t in improv thought I was crazy and my family thought I was wasting my time and thought I had joined a cult.

My 30s (1994-2004)

When I was in my 30s, people who I started out in improv with started leaving Chicago and becoming famous. Not a great decade. I kept believing I would be the next one to be famous.

Spoiler Alert: It did not happen. I was putting way too many expectations on improv. I was still playing to prove to myself and others that I was talented and thought the Chicago improv community should give me the respect I deserved, while I watched people who started out after me pass me up. One of the highlights of the decade, though, was I started teaching improv full time and developing my Art of Slow Comedy curriculum.

My 40s (2004-2014)

By the time I got into my 40s, I actually began to get good at improv, because I stopped doing a lot of the bullshit of comparing myself to others and constantly trying to prove to myself. I had nothing to prove anymore, because most of the people I started out with were gone. And the ones who were still here, I appreciated even more. I started to learn from the younger people I played with and my students. It was a real shift. I felt the pressure was off, and I started to understand that the results I was looking for in improv didn’t come just from doing a show. Even better, I met Lauren (on New Year’s Eve 2008) and we got married.

My 50s (2014-today)

In my 50s, my responsibilities changed. I became a dad at 52. Now I have a lot more life experience to draw from in my improv. My daughter teaches me to be more silly and playful. Today, I improvise to express myself, which is the whole reason I fell in love with improv in my 20s in the first place. Today, I realize that I love improvising, but I love teaching people to improvise even more than doing it myself. It feels good to stop trying to get laughs and instead pass on what I have learned.

As we enter a new year in 2023, I’m interested to see where my improv career goes next. What has your improv journey been like? Tell me in the comments below.

Want to take your improv to the next level? Don't miss Jimmy's Long Form Tune-Up on Dec. 31! Or want to try it for the first time? The next Level 1 class starts Jan. 12!