Superpower on the Side is a series that features WeWork team members and how they spend their time when they’re not at work.
If you were one of the 8,000 employees who attended the 2018 WeWork Summer Camp outside London, chances are you witnessed Ashley England in her element: onstage, microphone in hand, improvising jokes, and making people laugh.
It was an impromptu set, but she was ready for it. Minutes before she took the mic, backstage organizers were trying to figure out how to fill time between presenters—and that’s when cofounder Miguel McKelvey suggested England get onstage.
“I was floored that he would be that supportive to give me that opportunity,” says England. Serving as the master of ceremonies in front of thousands of your colleagues is not for everyone, but England is comfortable in front of an audience. In addition to her job as a learning experience designer working out of the company’s New York City HQ, the 34-year-old is also a comedian.
She first performed for her colleagues at the 2016 Summer Camp. “It was the first time I performed on a huge stage and showed New York that I was not just a ‘learning’ person,’” she says. Since then, in addition to emceeing the 2018 Summer Camp, she did introductions and entertained the crowd between presentations at the company’s Global Summit at Hulu Theater at Madison Square Garden in January.
“The biggest challenge [of being a comedian] is I can’t turn it off,” says England. “I am joking all day long. So hosting is a great opportunity for me to use that for good at the company.”
After hours, most of England’s nights are dedicated to improv. She rehearses with her improv ensemble team, Varsity, a few times a week to prep for their gig every other Tuesday at the Upright Citizens Brigade Theatre (cofounded by Amy Poehler—maybe you’ve heard of her?). She also dedicates one evening a week to writing her own stuff. And, if she has the time, she’ll pick up other shows around the city.
“A lot of improvisers don’t have day jobs or work little jobs,” says England. “I feel very lucky to work in an office environment because I get such good material and have such different experiences than maybe other people in comedy. There’s such good stuff at all-company meetings or just in the hallway.”
Learning and improv have been connected in England’s world from the start. She graduated with her master’s degree in education from Canisius College in Buffalo, NY and got a job teaching fifth and sixth graders.
“When I was teaching, I was performing the whole time,” she says. “I would get on tables, sing songs. If my kids weren’t paying attention, I would just fall on the floor like I’d died. I was a pretty insane teacher, but I think they also liked it. I was always drawn to trying to make people laugh.”
So she decided to hone her skills. “I remember seeing in the paper Level One improv, six classes for $100,” recalls England. “I thought, I can take one night of classes a week.” That led to her enrolling in a six-week summer intensive program at iO Theater in Chicago. (Poehler is an alum, as are Tina Fey, Stephen Colbert, Chris Farley, Seth Meyers, and Vince Vaughn, among other famous funny people.)
“I was so bad at improv, but I just fell in love with it for some reason,” she says of those early years. She left teaching to pursue her passion, exploring the different types of improv, including sketch and music. Her work in the latter category is what caught the attention of the staff at famed comedy club and improv school Second City, and in 2013 she joined their music conservatory program, then the regular conservatory program one year later. By 2015, she was on the Second City House Team. Later that year, she landed a role performing on a Norwegian cruise ship.
But while she was finally getting paid to do the thing she loved, and the money was good, after four months the long days at sea started to wear on her. “I’d always wanted to live in New York City, but I kept taking other paths,” she says. “All my stuff was packed because of the ship, so I decided that was the time to move.”
England started looking for jobs before she got off the ship. When she came across a listing for a position on the learning team, creating learning and professional development experiences for the WeWork community, she decided to apply.
“I’ve always been an instructional designer,” she says. “Even when I was a teacher, we didn’t have textbooks so I was always making my own stuff. That just sort of continued.”
In April 2016, two weeks after leaving the cruise ship, England moved to New York. Two days later, she started her job at WeWork. And her first weekend in the city, she started classes at UCB, where she continues to perform.
Sometimes, her coworkers go to her shows to support her—and that means a lot. “To think someone wants to spend an hour watching me being my most authentic self, making up funny characters and stories, it’s just so very nice,” she says. “It makes me feel like this is a real community and we want everyone in the community to do well at whatever they choose.”
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