Chicago Has Your Back

This post is part of The Heart of Chicago Series that will be running on South of I-80 for the month of March. Jessica Mitolo is an instructor at The Second City Training Center and I was fortunate enough to have learned from her.

Chicago Has Your Back by Jessica Mitolo

I moved to Chicago six years ago to study improvisation and sketch comedy. I was living in Washington, DC at the time and while I had been interested in comedy for several years and wanted to take classes in the city known for training all of my favorite performers, I wasn’t sure what to expect and I worried about leaving behind the friends and opportunities that I had in DC. After giving it a lot of thought, I still remember the exact moment I knew I had to make the move:

I was on the phone with my friend Adam who had moved, with his adorable wife, Alisa, to Chicago a year earlier. “Jessica,” Adam said, “I can’t promise that you will make a lot (or any) money doing comedy out here. But I can promise that there are a ton of opportunities for anyone who wants them. And, there is a group of people out here who would really love to see you.”

Two weeks later, I moved into my own studio apartment in Lakeview and it wasn’t long before I realized that Adam was right. Not only were there more opportunities to take classes and workshops than I could have imagined but every teacher and coach that I had was more than generous with their stories, advice, and time. I know that Adam meant that our friends from college would be happy to see me – but it felt like everyone that I met was warmly welcoming me into the city.

Photo courtesy of Erin Skibinski

Photo courtesy of Erin Skibinski

I realized that what makes Chicago the best place in the world for improvisation is that people here aren’t only performing improv, they LIVE improv. People in Chicago will do everything in their power to help you get where you are going. They listen to one another. They are open and able to adjust when something doesn’t go as planned (especially those of us who rely on public transportation). And year after year, they accept the cold and the snow because they know that summer is on its way and that it will be worth the wait.

My favorite improv ritual is that before a show, the performers gather backstage tell each other “I’ve got your back.” What this means is that no matter what happens during the show, everyone in the ensemble is going to look out for one another and make sure that every, single move each person makes will be not only accepted, but it will be celebrated. And while there is a magic about watching this happen during a show or in a writers’ room, what always astounds me are the ways that I watch students, teachers, performers, alumni, and audiences within the comedy community time and time again prove that this is just as true offstage as it is on.

People leave their house at 11:30 pm during the worst days of winter to catch a friend’s midnight show. People donate their money and time to help fund and create one another’s dream projects and even, on more than one occasion, rally together to help pay off emergency medical bills.

Six years after moving to Chicago, I feel so lucky to be teaching improvisation and sketch writing to so many people who, like I did, walked into their first class not 100% sure what to expect. I love knowing that I am welcoming them into a community that will support them and help them grow not only as artists, but as communicators as well. And while I like to think that every student might be the next Tina Fey or Steven Colbert, I know that every student will walk away being a little more confident and the people in Chicago have their back.


Jessica Mitolo is originally from Ohio. She currently teaches at The Second City Training Center. She as produced, directed, written, and acted in several shows across Chicago.

Jessica Mitolo pic 2

Photo courtesy of Jessica Mitolo

If you liked this post, you may also like: My American Dream, My Chicago,  Sweet Home Chicago as Told by a Southern CalifornianThe Bonds of Chicago are Unbreakable, World Class Chicago, The Chicago Connection

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