Improvise your way to business success: Lessons from The Annoyance

Published · 4 min read

It’s Friday night. You’ve got a drink and a snack, and you’re settled into a cushy theater seat, eyes on the stage. The actors appear under the bright lights and launch into a scene. There’s raucous laughter around you from start to finish, because this isn’t any old theater show—this is improv.

And improv is a lot like business. Sometimes the people around you do something unexpected. Sometimes you try out an idea and it falls totally flat. Sometimes you get nervous and have to forge ahead anyway, because the show must go on.

Charley Carroll, the managing director of The Annoyance Theatre & Bar in Chicago, knows all about both. After graduating from Valdosta State University (“Which I always joke is an Ivy League school,” Charley laughed, always true to his comedy roots), he moved to Chicago with the goal of starting his own theater one day. In the meantime, he managed antique art shows, taught high school for a while, and eventually ended up at Groupon for about five years. “I quickly moved up the ranks in their account management organization, working with small business to help grow their marketing,” Charley explained. “I really got to learn small businesses as a whole, all their ins and outs, and help them establish marketing goals.”

Meanwhile, Charley’s comedy home was The Annoyance. Last fall, he was able to combine his passion and his work as the managing director of the theater. He’s been able to parlay lessons from the stage and his business career into ongoing success for The Annoyance—and now he’s sharing his wisdom with the Sage community.

Find your niche.

“Chicago is sort of the comedy capital of the country, if not the world. There’s Second City, Improv Olympic, and The Annoyance,” Charley explained. “The Annoyance is the one that was built later than those other two schools. The way we distinguish ourselves is that we use improv to create full length musicals and plays. So you can come see a written musical, but it was established and created by the actors through improv.”

In a city with so many high quality comedy options, this distinction is important. Second City uses improv to develop sketches, and Improv Olympic uses improv as a medium in itself. The Annoyance was able to carve out its own distinct niche that allows it to flourish. That also fosters positive relationships throughout the rest of their specific business community, Charley said. “We have great relationships with both of those theaters. A student can come to The Annoyance and learn our style, and then they can go to Improv Olympic and learn that style, and then they can go to Second City and learn that style. We’re never going to limit that—we think we can all build off of each other well. We share a lot of performers, and we have our own niche.”

That philosophy is clearly working. The Annoyance has two theaters and currently runs 31 different shows per week. “It’s a blossoming community,” Charley said, and it’s only continuing to grow.

Stay focused on the big picture.

“My number one philosophy is try to keep the big goals in mind,” Charley said. “It’s very easy when your job encompasses a lot of things to get sucked into very small things and just do the day-to-day ‘get by’ things.” But Charley is determined to do more than that: a new marketing plan, a more robust advertising strategy, and so on. By keeping those top of mind, he’s able to make even the smaller activities more productive. “I try to spin the little tasks in a way that helps me accomplish the larger goal,” which is only possible because he keeps his eyes on the prize.

He’s also keeping an eye on the larger trends of business, such as the opportunities that data can offer. “How to collect data and use data to inform you about your own business—that’s huge.” Charley’s ideal is being able to say, “I know exactly how much money I’m making whenever I sell this product, whenever I sell a class, and how many I need to have in order to grow us as a company.” To get there, he emphasized, business owners have to operate on more than just gut feelings. During his time at Groupon, he recalled lots of small businesses saying “I don’t feel like this is working.” His response? “I’d always say, ‘I respect that feeling, but I can’t work with you on feeling—I can only work with you in numbers.” As you look at the big picture of your business, use all the data available to make sure that picture is accurate.

Learn to be confident.

The magic of improv—which can serve every businessperson—is confidence. “You don’t dread the inevitable presentation we all have to give. You learn how to be comfortable just being yourself,” Charley explained. “That’s really what The Annoyance’s style is all about. We talk about creating a character, believing in that character, and playing that for a length of time without judging yourself. The same is true in a business meeting.” You learn how to get up in front of a group of peers and convey information in a confident way, Charley said.

The other part of that confidence is being willing to say what you really want out of life. Charley told an anecdote about Andy Richter, of “Conan” fame, who started off at The Annoyance. At the beginning of class, the instructor asked everyone “Why are you studying comedy? What do you want to do with it?” Most people gave the typical responses: for fun, to be comfortable in front of groups, and so on. But Richter said “I want to be on late night television.” By putting his dreams out there honestly, he increased his chances of connecting with the opportunities that would get him there. “So just be really honest about what you want,” Charley advised. Whether it’s for your business to grow to a certain size, a particular dream client, or some other personal benchmark of success—name it and claim it, confidently.

Just be ready to improvise a little bit along the way.

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