Improvising to improve business

Second City improviser Andy Eninger says risk-taking was a lesson he needed to learn more than anybody.

October 14, 2013

Dan Weissmann

Back in the summer, librarians from all over the country flew into town for the American Library Association’s annual conference. On a Friday morning a few dozen of them gathered in Second City’s main theater. A big space was cleared in front of the stage. 

Workshop leader Andy Eninger told the group what to expect.

“So, today, is going to be very interactive,” he said. “It’s a little like learning to swim, this improvisation.  You can analyze it, you can talk about it, but its only when you jump in the water that you realize how it’ll work.  So we’re going to throw you in the proverbial water.”

Before tossing them in, Eninger reassures them with a fable about himself. Once upon a time, in the 1990s, he was a guy with an office job. “I worked at an advertising agency—not as a creative person but as a database administrator—and was sneaking off at night to take improv classes.” 

And the classes, he says, transformed him. “The more I studied improv here at Second City the better I got at my job by day, and began to manage people— not just some servers and machines— and started to do more and more creative work.”

Eventually, he quit to do improv full time, “and have not looked back since,” he tells them. “Well, maybe a couple of times, for the health insurance.  But other than that…”

Like anybody spinning a fable, Eninger is leaving out some important stuff. Actually, there were some lean times in there. Leaner than lean. When he left his office job in May, 2000, he stepped off a cliff and fell pretty hard.

He and a friend rented an office and hung out a shingle as improvisers for hire— doing custom shows and running trainings like the one he’s doing today, but entirely on their own.

“We had a few gigs on the line, so we had a few gigs coming up,” he says. “But there was this crushing reality that there was no real income. We didn’t know where it was going to come from.”

It got worse. Just as their enterprise was starting to pick up steam, 9/11 happened. An agency representing their company on the college circuit scammed them for thousands of dollars. He had three years of negative income, and racked up credit-card debt that took ten years to pay off.

“We had a lot of pitfalls,” he says. “Things that, if I had known those things were coming up, I never would have taken that risk.”

And yet: Today, he calls those pitfalls an investment. And risk-taking is a big part of what Andy is here to teach the librarians in the Friday improv workshop.

Any performance— especially improvising— is inherently full of risk: The risk that you’ll fall on your face, look like a jerk. 

In everyday life and in business, we confront the same risk every time we raise our hand in a meeting, propose a new project, or initiate a new business deal.

Improv training focuses on getting people into the habit of taking those kinds of risks.

When he first started learning to improvise, it was a lesson Andy Eninger needed to learn as much as anyone.

“I mean, I’m the person who, in fifth grade, went to the bathroom in my pants because I was scared to ask to go in from recess to go to the bathroom,” he says. “I still have that operating, any time I have to raise my hand or speak out of turn. And improv is the thing that makes it possible.”

What he learned from improv, he says, was “to risk in the moment—to say the first thing that comes to mind. Because I was doing it in class, every night and all the time, I couldn’t not-do it in my job.”

And so, he became a much more valuable worker in that day job.

“I always would see opportunities, or see systems that were not working,” he says. “Like, ‘Oh, you’re dealing with this ridiculous spreadsheet. It gave me the confidence to speak up and say, if you allow me to work on this, then I know I can make it better.”

So, he did, and he got noticed. He got promoted. He survived layoffs. He even started to do some creative work.

“But there was a moment when I thought, if I don’t disrupt it now, I can see my life laid out in front of me,” he says.

So he saved up some money, and took a bigger risk. He left that cushy day job. And we’ve already heard about how tough that was at first.

But over time things turned around, thanks to Second City. Andy started doing corporate training workshops, got some gigs as a performer, and eventually became head of the writing program at Second City’s Training Center. By 2008, he says his take-home pay finally matched the paycheck from his old corporate job. It felt pretty good.

Andy still makes time for the corporate workshops, which are a big moneymaker for Second City. They charge thousands of dollars per session, to clients including Pepsi, General Electric, and hundreds of others like the American Library Association.

So, how does it work?

WIth the librarians, Andy gets everyone into a big circle, and asks a volunteer, Mike, to come to the center. Then he has him strike a pose. It can be anything.

Mike makes a silly face and holds his arms up.

“Perfect, now hold that for a moment,” Andy tells Mike.

“Now, this”—Mike—”is the first half of a statue,” Andy tells the group. “Somebody come out and show us the second half by adding another pose.”

Someone does. “Mike you can say thank you,” Andy says. “Your job is done, good work.”

Now it’s time for another volunteer. And another. The poses are goofy, random, and gone in an instant.

“It’s perpetual motion,” Andy tells them. “Someone is always coming out to join.”

Volunteers keep coming up, one after another, and Andy eggs them on.  “If you haven’t been out, just urge yourself to go out, trust that gut instinct,” he says.

When it’s done, Andy asks a question: “If you did not go out, why did you hesitate to go out?”

“I didn’t know what pose to do,” a librarian answers.

“Right,” says Andy. “Because how many poses would be wrong in this game?”

The room fills with laughter—recognition and release.

“Yeah,” Andy says, “it’s a game in which really anything will be right.”

Andy builds on the moment.  He asks the group, “What does that person in the center want?”

Immediately the answer comes: To get out of there.

“Yes, to get out of there!” Andy says, channeling the player: “‘OOOH. come in and save me!’  And we’re all there thinking, ‘Someone should go and help them out.  Not us, but someone should go out there.’”

Andy tells the group that the impulse to help others is one of the things that lets improvisors take risk after risk.

“We find out that that bravery comes not from any brilliance on our part,” he says, “but from: ‘I need to get my idea out there to support that other person.’”

After the workshop, library administrator Sarah Dallas reflects.

“I’m kind of a shy person, and this was a real challenge for me to do something like this and I knew I had to be more out there,” she says. “And I was kind of going through this and getting through…”

And then came the final exercise: Working in a small group the librarians created a whole scene— a fake ad for a fake product— out of nothing and performed it for the group.

“When we got the final assignment, to perform in front of everybody, I just wanted the floor to open up and let me drop down,” she says. “But it didn’t. And with the support of the group, I survived, and for me that’s a victory.”

She says she’ll remember these moments when she’s running meetings back home at her job..

Responses like these are exactly what Andy Eninger hopes for.

“We don’t make them pretend to be improv performers,” he says. “For us, it’s all about what they’re doing  It’s all about what their challenges are. We want them to have the joy that improv is for us, but we want them to be able to take it away, so they can use it that next Monday.”

That is, he wants to give them just enough risk to help them re-think their routine.

Dan Weissmann is a reporter for Marketplace.  Follow him @danweissmann.

“At What Cost?” is made possible in part by the John A. Wing Society, an initiative of the Illinois Humanities Council to improve dialogue about business and the common good.