Maya May left a 6-figure office job for comedy: Now she can make more in 1 hour than she did in 3 weeks

Maya May left her six-figure corporate job in Chicago to find success as a comedian in Los Angeles.

Maya May.
Photo by Tandem Photo

After Maya May's first comedy set in 2014, she left New York-based Gotham Comedy Club and burst into tears. Happy tears. For the first time in her life, she felt like she was on the right path. 

"It was an epiphany," says May, who thought to herself, "This is the thing that you were meant to do on this planet." After her light-bulb moment, May decided she didn't want to do anything else for a living. She wanted to "write jokes and tell jokes and be on stage." Her next step was to figure out how to do it. 

Thus began a six-year journey to become a successful stand-up comedian. Going from her previous jobs as an entrepreneur and executive assistant making six figures to a successful comedy career wasn't easy, especially since she was also a mom to a young daughter. Here's how she did it.

Since comedy doesn't pay 'at all off the bat,' she came prepared

Changing from one career to another is rarely simple. For May, who was working as an entrepreneur in the language learning industry, becoming a stand-up comic wasn't one big move so much as a series of little ones. 

May understood she could make comedy her career if she focused on it but also acknowledged that comedy "is not one of those careers that pays really anything at all off the bat." Even though she already found success by performing at a big comedy festival a few months after taking her first class, May continued to work full time at her corporate job. But she found it tough to balance a full-time job with stand-up comedy.

Eventually, she decided to make life changes that let her work smarter, not harder.

The first: "Underemploy" herself so that she could focus more on comedy. She landed an executive assistant position that pulled in six figures but that she found pretty easy. "I knew that I could do the job, basically, in my sleep. I wasn't great at it, but I did my best," she laughs. "Because my focus really, truly was comedy. So apologies to that boss."

Maya May: How I left my corporate job to become a comedian

Video by Courtney Stith

Even then, May didn't have time to "spend hours at the club, networking with people [and] doing shows," because of her day job and needing to care for her daughter. So she moved her family closer to the comedy clubs in downtown Chicago and her job to shrink her commute.

Those changes let her focus on getting into the "right" shows and festivals. When she couldn't get on stage, she still put in the time, writing jokes and performing them to her daughter and to her toiletries.

While working this way made May's career grow faster, she says that she still had to do "grunt work" like every other comedian. To get an audition for an NBCUniversal stand-up program in 2014 and 2015, May slept on the sidewalks of New York City the night beforehand so she could be one of the first 100 comedians in line. Even though May was ultimately unsuccessful in getting into the program, the experience underlined her commitment to comedy. 

"It was one of those things where it's like, 'Oh, Maya, like if you're willing to do this, clearly this is the career that you're willing to sacrifice things for,'" she says. 

She positioned herself to break into the 'big leagues'

In 2018, May decided to make a big change and move to either New York City or Los Angeles to have a chance to join the "big leagues." 

After testing the scenes in the two cities, May decided to move to Los Angeles and dedicate the next year to doing comedy. Once she arrived on the West Coast, May was lucky to find an agent at The College Agency. Within a few months, she was flying around the United States performing.

Moving to Los Angeles meant that May was leaving her six-figure salary and all of the benefits that come with a corporate job, like health care. Still, she had six months of living expenses saved for her and her daughter to live on while she tried her hardest to make comedy pay. 

And once she leapt in full time, May saw the earning potential of a successful comedy career: She could make more in one hour of comedy than she did in three weeks at her day job. 

I didn't want to be one of those people that got to later in life and regretted the fact that I didn't go for the thing I really wanted to do.
Maya May
Stand-up comedian

"I was like, 'What have I been doing my whole life?' I should have been focusing on this!" she says. "Now obviously, there's all the background work that goes into stand-up comedy so it's not just the one hour that you're on stage. But I love all the background work that goes into comedy."

Since being able to book new shows on a regular basis wasn't guaranteed, May looked at her career like a new business, with trajectory and milestones. If she was hitting her milestones, then she would keep going, even if that meant spending down her savings or taking on debt. 

"People have no problem investing in a business, right?" she asks. "But for some reason when that business is ourselves and when it's tied to the arts — something that can seem like it's a long shot — then we have a harder time."

Maya May performs virtual comedy.
Photo by Maya May

Pivoting to virtual comedy

In 2020, despite the instability the coronavirus pandemic caused, May's commitment to risk-taking, combined with her practical approach, really started to pay off. 

When the pandemic caused shutdowns around the world, May's agency pivoted to virtual comedy. May did a Zoom show and realized she had a leg up on most comedians, thanks to her hours at home practicing performing in the bathroom to her toiletries. 

"I felt so fortunate," says May, who realized, "this thing that actually hindered me before now actually helps me because virtual is a format that I'm very comfortable with."

As colleges and universities adapted to virtual events, requests started flowing in. Currently, she's "touring" nationwide through her "Virtually There" comedy tour and performs for 5 to 6 hours a week — a feat she says was unheard of before the pandemic. 

How to follow your dreams while 'everything is up in the air'

Now is the perfect time for people to pursue their passions, May says, because "everything is up in the air" due to the pandemic. She recommends mapping out your plans and cutting out any after-work activities that don't support them, with the exception of self-care. May prioritizes exercise, meditation, journaling, and getting at least six hours of sleep.

As a 43-year-old who started comedy at age 36, May says it's never too late to invest in yourself and your dreams. For her, achieving success is about calculated risk and managing fear. Instead of viewing fear as a bad thing, May believes it's a signal that you're trying something new. 

"It's your brain telling you, 'Hey, what you're doing ... you didn't do it before. Why are you trying something new?'" says May. "So I thank my brain: 'Thank you for warning me that this is crazy. I got this.'"

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This story has been updated to reflect how many hours per week May performs comedy.