Every creative field has its overnight sensations.  However, for most  comics working the microphone, success means building on smaller goals to reach bigger ones – which Megan Gailey has done since leaving her original hometown of Indianapolis for Chicago about five years ago.

“When you're starting out, you need to be onstage constantly, getting up as much as you can,” said Gailey.  “I had a friend that moved here: 'There's two or three open mikes a night – you can be doing it at a higher intensity.'”

Of course, moving to a bigger place also means more competition, and working harder to keep up. “You visit a club, do a guest spot, and if they like you, you'd get to come back, and work,” recalled Gailey, of her move. “I still do that.  You're constantly sending feelers out: 'You want me?'  You compile a list of clubs that you go to, and set the goal further and further out.”

Gailey began doing standup at 22, after graduating from Purdue – and living at home as a full-time Alzheimer's caregiver for her grandmother. She's since performed all over the U.S, as well as Ireland and the United Kingdom – and has been named one of Comedy Central's “Chicago Comics to Watch.” 

“I'd always known that I wanted to do standup, but didn't know how to get into it,” said Gailey.  “I had a wide open schedule, so I'd watch an open mike in Indy, sign up, and wait a month to go up.  I went up for my first time, loved it, and wanted to keep doing it.”

Since moving to Chicago, Gailey's also distinguished herself as the co-founder of Your Funniest Friends, and serving as a co-host for “Naked Sports Live,” a weekly comedy podcast.  She sees herself as a comic who's able to get laughs out of the regular things in life.

“I'm a 27-year-old straight woman, which is a pretty under-represented voice in standup comedy,” said Gailey.  “I like to have fun.  I'm a little flirty, but it's mostly just about my life.  I definitely talk about dating, but I also talk about my family a lot, and stuff that I'm going through.”

Gailey also draws inspiration from work experiences, including her 18 months as a retirement community programming director, which marked the next major transition in her comedy career.  “I left to do standup successfully – even if you're working at a day job, you want to be doing something else,” said Gailey.  “That is the reality of it.  I reached the point where I was having to turn stuff down because of the day job.”

In many ways, however, Gailey's biggest test is coming next month, when she leaves Chicago for a tour that keeps her busy  through mid-April – which she'll follow by moving to New York City.

“A lot of my closest friends have moved there in the last year,” said Gailey.  “I've reached a point where I love it here (in Chicago), and gotten to do everything I want to do, but I'm also telling myself, 'It's time to move on.'”

Such groundwork lays the foundation for success, however. “My dream is to be funny in any room.  I've performed in a Harley Davidson dealership, (and) basements of churches that have been shut down.  It's not all nice clubs. and theaters. To be funny anywhere is the main goal, I think,” she said.

Such moments, Gailey jokes, underscore the need for being “delusional enough” to quit worrying about the odds of success.

“Once you stop thinking you're going to be fine, that's when you stop.  But when you're still at the point of (saying), 'This sucks, it's gonna take a long time, but I truly believe it will work out' – that's why you just keep doing it.”

About The Author
Author: Ralph Heibutzki


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