Photography by Miguel Jacob Credits: Photography by Miguel Jacob
Though she has already built an undeniably impressive career (Kirstine Stewart has become a household name and a mustfollow on Twitter—and she's done it while raising two children), Kirstine is remarkably modest. When asked how she made it to where she is today (was there a 10-year plan?), she says, laughing, that all the plans she's made have failed miserably.
Kirstine started out with the ambition of working in publishing, but around the time she graduated from the University of Toronto with a degree in English literature, the publishing market took a downturn and her dreams were dashed. She had no choice but to answer an ad for a receptionist job. "You don't know where you're going to be, and that's kind of the fun part," says Kirstine, reminiscing. She found a great role model in her boss at that first job and slowly moved up the ladder in the media world, working at Trio NewsWorld International, Hallmark Channel and Alliance Atlantis before eventually becoming executive vicepresident of English services at CBC.
That's where she was when she landed a job at Twitter. Many speculators thought it was a huge risk to leave the media giant for a relatively young social networking company, but Kirstine didn't see it as risky; she knew that a company based in social media was the future.
Tech companies like Twitter are all about taking chances— doing something different in order to move forward. "Ultimately, what we're chasing is what people want and need," says Kirstine. "And they can't communicate what those needs and wants are, necessarily, so you have to build for that before they even know what that is." She explains that, at Twitter, it was the users who came up with the idea of retweets and hashtags. "Clever companies are really listening to what people are saying they need. And that changes how leadership can happen."
Taking risks and delivering groundbreaking ideas require confidence, which
can be a challenge for someone who's shy. Over the years, the naturally reserved Kirstine (who's never taken a selfie) has learned to get past the selfdoubt in the back of her mind. "I had to get over myself and ask, Wait a minute, what am I afraid of?" she says. "When you're self-doubting, maybe you're thinking too inwardly and letting that inhibition curtail what you're going to contribute." And, like many with a lot of responsibility, she's dealt with a bit of impostor syndrome—the feeling that you don't deserve your success—but she used it to her advantage. "If you can channel it and make it something that motivates you to learn more, that's a good thing."
"Learn more" is the best advice Kirstine can give in today's fast-changing business world. It's what she tells her two daughters, who will be entering the job market in the next few years. "The eldest is already in university. She doesn't know what she wants to do, and I told her to keep it as broad as she could, because who knew jobs like this existed four years ago? I said, ‘Concentrate on your interests and just learn as much as you can about everything.' "
Having a mother who has shattered the glass ceiling as a high-powered VP at an ahead-of-the-curve social media company has taught Kirstine's daughters another important lesson: Success is within reach no matter who you are. "They think they can do anything," says Kirstine. "And I think that's pretty cool."
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