Credit: Lisa Predko

Posen, 47, is artistic director for Stage 773, program head at Second City Training Center, and executive producer of the Chicago Sketch Comedy Festival.

I grew up in Glencoe. My older sister—she’s nine years older—would be practicing the piano, and after she got done, I, as a five-year-old, would sit down and start playing the same thing she was playing.

When I went into high school I started getting involved in musicals. But when I graduated I said, “I’ll be a good North Shore boy and get real-world degrees.” So I took a prelaw degree and a psych degree on top of that at Indiana University, with a concentration in business.

When I graduated, I took a year off and I started taking classes at Second City because someone said, “Hey, these classes were fun. You should do it.” That was back in ’87, ’88, ’89, and the scene was very different. There were only 100 or 150 people studying back then, not like the 2,000 people you have at Second City now.

I loved it. About six months in, I quit my job. I started waiting tables. My characters were weak, so I started taking classes at Columbia. I ended up getting another undergrad degree, this time in acting. By then I was acting and auditioning in Chicago but I ended up getting my MFA from the University of Illinois in performance.

I was waiting tables when I met a patron who said, “Hey, I run Focus on the Arts for Highland Park. Do you want to teach a workshop?” I remember taking this napkin the night before and jotting down a couple of exercises that I kind of remembered from classes. I show up the next day in my ripped-up jeans because it was the late 80s, and I’m being guided down the hall to my classroom. And I go, “As long as I have five people in the classroom—that’s all I want.” And then I’m walking closer to the room I go, “Holy balls, is that my room?” And looking at this little piece of napkin and this room of hundreds of kids and going, “What the fuck? Dude!”

I go in there and taught a class for 45 minutes, and when I left that workshop I go, “I want to be a teacher when I grow up.”

At the end of grad school I had an equity contract in Wisconsin. I was going to travel the United States doing Shakespeare. So I go up there and within a couple of days my dad was diagnosed with colon cancer. I had to break the contract to move back to Chicago and be with my dad.

So here I am with a grad degree, living in the house that I grew up in, and I’m going, “Dude, I just fucked myself.” But then I called the head of the training center at Second City, because I wanted advice on how I could tap into teaching at one of these institutions. So I went over and we hung out for about an hour and a half, and he said, “I got an instinct about you. I want you to teach my class tomorrow for the first hour.” I show up at Second City the next day and do that. He calls me back and says, “You start next week. You have three classes.”

From there I started teaching at Second City. And then Columbia picked me up. Then I started teaching at Steppenwolf. I still feel like the more I teach, the less I know. The more I dig in, the more I realize I don’t know anything about this.

I always had these strong ideals about what theater is. There is nothing like Chicago theater, which is all ensemble takes—the power of the group. It’s an honor to be on stage, to communicate a story, to move an audience to action and thought. And I really love that every single person has something to offer.

I started a company and we started doing really good work. We started putting up more and more shows. We won award after award. In 2001 we were planning on doing this original musical, but we couldn’t get the budget down. So I pulled the plug on it, but I had this space at the theater. I said, “What if we take this space and get all these sketch groups together and give them a run?” It was a fluke.

After the third year, [Chicago Sketch Fest] popped. If you follow your vision it will stick. Last year we had close to a hundred people on a list just to volunteer to pick up beer bottles, because they want to be part of that vibe. Almost 11,000 people came last year over eight days.

Then I created a not-for-profit company, and in about 2004 our bylaws and board members were set and we started moving forward on creating a multitheater complex. We were getting really close to signing on a property when the Theatre Building called us up and said, “Let’s talk.” They were having a tough time so they passed the torch to us.

So we took over the operations and infused close to $2 million into the property. We took this tired, historically wonderful complex and breathed new life into it. We picked up the cabaret community, the stand-up community, the improv-sketch community, the storytelling community, the burlesque community—all these different mediums. We took our things that we hold sacred and brought them to this complex to give back to the arts community. —As told to Kevin Warwick