“Nerdy and awkward” is how Diane Flacks describes her teenage self. As a young woman she was constantly worried about fitting in with her peers at Tanenbaum Community Hebrew Academy of Toronto (CHAT). Now, she doesn’t worry about fitting in. Instead, she writes about it.

For years she wrote a column for the Toronto Star called In the Thick of It about people who rose above unfortunate circumstances. As a former columnist for a large newspaper, a contributor to CBC Radio’s Definitely Not the Opera and a critically acclaimed actress, Flacks has an influential platform to explore these kinds of social issues.

“I’ve written a lot about the struggles outside of the field: Whether that is sexism or a disenfranchised person trying to fit in, how people manage to handle it when life throws them something insane and how they manage to cope with it.”

When Flacks reflects upon her high school experience, she says in retrospect she was probably less offbeat than she thought. Although she may have felt like an outsider, the school was a positive experience. The tough academic standards of CHAT prepared her for the hard life of an artist. She says that CHAT laid the foundation for her to create “cohesive and coherent arguments,” which has had a direct impact on her work. To add meaning to her art, Flacks forms a point of view about certain aspects of society in order to present her audience with a thoughtful discussion — skills she had learned  in high school.

“I loved the academic rigour that I learned there. You have to work hard and really fast, and despite the fact that people think artists aren’t thinkers, you have to be.”

Flacks typically juggles multiple projects at once. But, like many artists, there have been lulls in her career. Despite her success at the CBC, the Globe and Mail, the Toronto Star and other major publications, she insists she still sometimes struggles. However, she is so busy that sometimes she longs for periods of temporary unemployment.

“There are so many people who are successful, but it’s an 85 per cent unemployment rate. It’s easy to get discouraged … you have to be nimble enough to participate in many different forms.”

Currently she is preparing for her upcoming film, Portrait of a Serial Monogamist, with Christina Zeidler.