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Mindy Kaling.Rich Fury/Getty Images

Mindy Kaling should be everybody’s boss – I concluded that one minute into our half-hour Zoom interview. We were talking about the fireside chat she’ll do on Oct. 19 at C2 Montreal (an annual conference that aims for the overlap of commerce and creativity), and she came across as this terrific mashup of game and wise, passionate and amused. I would follow her anywhere.

Few artists have had such a smashing evolution – from the “lucky employee” who starred in and wrote 26 episodes of The Office, to the head of her own successful film and television company, Kaling International. Her multiple high-profile projects include the Netflix series Never Have I Ever (40 million viewers; season three in development); the HBO Max series The Sex Lives of College Girls, which drops in November; the film Legally Blond 3 (Reese Witherspoon returns as the iconic Elle Woods); a comedy for Priyanka Chopra; and a series based on the front office of the Los Angeles Lakers, co-produced by Lakers’ president Jeanie Buss.

At 42, Kaling is also a single mother to Katherine, 4, and Spencer, 1 (their paternity is private), and the author of three bestselling books – most recently Nothing Like I Imagined, which came out last October. Plus, her company is adapting a Canadian novel, Hana Khan Carries On, by Toronto writer Uzma Jalaluddin. It’s a romcom in the spirit of You’ve Got Mail, set in a halal restaurant.

“What I’m trying to do is really simple – see family stories and romances through a different lens, and show worlds people haven’t necessarily seen,” Kaling says. “Uzma’s book is a perfect example. Muslim-Canadian, so fresh and funny – she defies a lot of expectations. But someone like her getting to have a platform is unusual, so that’s exciting.”

With Hana Kahn, Kaling’s C2 appearance and Never Have I Ever – whose star, Maitreyi Ramakrishnan, hails from Mississauga, Ont. – is Kaling having a Canadian moment? “I’m constantly finding talent in Canada – particularly South Asian talent,” she replies. “One reason we hired Maitreyi was that she feels so at home in her skin. Her point of view isn’t as outsider as mine was growing up in the 1980s and 90s.”

Mindy Kaling in The Mindy Project.FOX

Kaling was singular from the start. Her architect father and doctor mother, who met while working in Nigeria, moved to Cambridge, Mass., the year Kaling was born. “They veered from traditional Indian immigrant parents in ways I didn’t understand until I was an adult,” Kaling says. “For one thing, they spoke only English as home, which Americanized me quickly.”

A “bookish, chubby, outgoing” kid, Kaling would head after school to her mother’s medical office, where she’d write comedic plays in the phlebotomy room. Her parents indulged her love for Mad magazine cartoonist Sergio Aragones, even though they thought Mad was “very rude;” on their 11-hour family car trips to Niagara Falls (“the most Indian thing you can do growing up on the East Coast,” Kaling says), they’d listen to Nichols and May routines.

The wider world was less supportive. In her schools, a girl who was into comedy was an anomaly, and she never even landed a good role in a school play. “My daughter is already showing the seeds of a comedy mind,” Kaling says. “She loves to point out ironies, inconsistencies and hypocrisies.” She laughs. “Which can be irritating.” So when Kaling was touring potential schools for her kids, she made a point of saying to administrators, “I hope you like girls who are funny.”

After graduating from Dartmouth College and doing stand-up in New York, Kaling wrote a spec script that landed her in the writers’ room of The Office. She was just 24 years old – and the only woman in a staff of eight. “I had this personality defect – I refused to believe I didn’t belong in that world, even though I never saw anyone who looked like me on TV,” Kaling says. “I definitely felt the pressure to represent all women, all people of colour. But I refused to be Othered.”

Fiercely single-minded, she wrote the six-season The Mindy Project TV series for herself, and for several years treated her career as a “one-woman operation,” wanting to read every script, produce every show, give every note. “You know the saying, ‘Don’t sweat the small stuff?’” Kaling asks. “That saying was so frustrating to me, because I only sweat the small stuff.” But now as head of her company, she’s learning how to choose her team well and give them autonomy.

“It’s hard,” she admits. “I’m a controlling artist whose opinions and artistic choices feel fundamental to my soul. Those are not necessarily qualities that make a generous leader. But I have to be a mentor, because I don’t want to be the only Indian woman who gets TV shows on the air.”

Her strategy is genius: She’s hires young people, particularly young women of colour, for entry-level positions. In a year or two she puts them in the writers’ room of one of her shows. “Then when they have development ideas for pilots, they want to come to me first.”

She also takes the time she needs to find the talent she wants. To run her Jeanie Buss project, “I could have found 100 comedy writer guys who love basketball,” Kaling says. “But I wanted it to be a woman, so we took a few extra months, and found an amazing Asian-American writer, Elaine Ko.”

There have been snags in her learning curve, but Kaling chortles about them. “I worked on a show for eight years that made fun of the worst kind of boss you can be – Michael Scott,” she says, referring to Steve Carell’s character on The Office. “So when I became a boss, I kept telling myself, ‘I cannot be Michael Scott.’ I thought I would have a finely honed sense of when I was slipping into parody. And at least once a week, I’ll do something and think, ‘Oh, my god – I am Michael Scott.’”

For example? “Early on, I would ask these young women for an opinion about something I was writing or wearing, and they gave me such positive reinforcement, I’d think, I must be perfect! Finally I realized, they’re not going to tell me their brutally honest truth – they work for me.”

Kaling is aware that some of the interest her work is getting from entertainment bigwigs is “fear-driven – people not wanting to seem behind the curve of change and inclusion. You worry that once they get comfortable again, everything will go back to the way it was. But I also know that no one is coming to me out of the goodness of their hearts. It’s a business decision.”

Still, she has no intention of relaxing into her success. “I’m still striving, striving, striving,” Kaling says. “As a mom and a boss in my 40s, my life is objectively more difficult and complicated than ever. Yet I’m happier now than I’ve ever been.

“I don’t come from people who know how to enjoy and relish,” she continues. “I barely know how to vacation. Where I feel the most comfortable is launching into a project and getting it going. That’s when I feel the most myself.”

Special to The Globe and Mail

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