Money & Career

'I pranked my bully boss.' 7 women on their biggest career risks

The secret to a career you love may lie in your willingness to bravely take a leap.
By Sarah Boesveld, Dominique Lamberton and Katie Underwood
Taking career risks may be the secret to getting ahead. Photo, iStock.

If comfort and complacency are the enemies of success, calculated risk is its best friend. That’s truer now more than ever, when short-term contracts have replaced cushy salaries, self-made side hustles abound and achieving work-life balance often means sticking up for your own damn self. Yet taking a leap, whether it’s quitting your job or sharing an unpopular opinion, can still be excruciatingly hard.

In a recent Vancouver TED Talk, Reshma Saujani, founder of a tech advocacy group called Girls Who Code, argues that many girls are taught perfection (be polite, be pretty, play nice) while boys are taught bravery (swing high, play rough, jump). This early conditioning, she contends, results in a fear of imperfection and risk aversion that has nothing to do with ability or intelligence and everything to do with durable ideas about how women should behave.

Studies back her up, showing that women take fewer risks than men, particularly when we’re stressed out. Her solution? Celebrate women not for perfection but for courage and a willingness to try, even if trying means failing. We asked Canadian women of varying ages and professions to share their biggest career risks: rewarding, not so rewarding and everything in between.



I walked away from my dream promotion

I used to work in the radio and television industry as a marketing manager — a job I loved. Then I got pregnant, and I naively thought my life would remain exactly the same, except that I would have a kid. Soon after, a promotion came up for a director-level position. I had always been pretty ambitious, and I was aggressive about going after it. I took the position two months before my mat leave, and I had every intention of going back. But when I was off, my husband was travelling a lot, my extended family was an hour away, and I couldn’t find a daycare that I liked. A month before I was scheduled to go back, I turned to my husband and said, “I can’t do this.” As a type A perfectionist, I knew I would kill myself trying to balance everything. My kid and marriage would suffer.

So I approached my manager, an older guy, before I was scheduled to come back, saying, “Let me do this, but on different terms. Maybe I come back six months later, when I feel better about daycare?” Work-life balance was not in his vocabulary. He said, “Nope. You’re either all in or you’re out.” So I said, “Then I’m out.” A week later, the company offered me a freelance contract so I could work from home. I did that, two days a week, for nine years.

Financially, our family took a hit — we had food on the table, but we didn’t go on a vacation for, like, 10 years. I still feel like a bit of a failure because so much of my identity was tied up in my career success, but I can live with that. I was able to do a lot of “Mommy and Me” stuff: take my kids to museums, be with them without my smartphone taking over everything. Now that they’re older, I’m back to work full-time, which was a relatively easy transition because of my experience, but I’m very deliberate with my time. I used to feel guilty about that, but I’m getting my job done. And I’m doing it well.



I opted out of my office’s bro culture

I work in the sales department of a very large, very young company. There are a lot of great aspects to the culture, but it’s very heavily male. The guys shoot Nerf guns at each other, and their after-work activities involve hockey leagues. It’s a frat house in there, and if you’re not a member, people don’t respond well. I opted out early on, which, to me, meant not hiding who I was — I’m smart and I’m a feminist. I didn’t change myself to be less threatening or to fit in with the bros.

Soon after I started, I realized some of the men took issue with me. They weren’t messing with my work, but they made it uncool for other people to talk to me, sometimes by teasing me or excluding me from post-work parties. I knew I was screwing myself over by not making an effort to fit in. In my department, the conversations that get people to the top happen when you go golfing or drinking, and when you abstain from the social stuff, you are actively choosing not to build those professional relationships.

I believe opting out has slowed my progress; I had to work for three years before I got the promotion I thought I deserved. If I had gone along and pretended to be less opinionated, maybe I’d have gotten to my current job faster, but never in a million years would I want to earn something on false pretenses. It was very hard for a while, but I am better for it, I think... I hope.



I started my own business while I was pregnant

When my husband and I started our own software business [Plum, a platform that tests job seekers based on behavioural science to match them with employers], we had just moved back to Canada from the U.S. and into my mother’s house with our seven-month-old. It was early going with the business and we weren’t financially stable, so we waited another year to have a second child, then finally took the plunge. We were still fundraising for our start-up, and I worried about how to talk to investors while pregnant — would they think I’d be too distracted by the baby to do my job? I’m a larger, curvier person, so I wasn’t obviously showing, and I waited until the late months of my pregnancy to disclose to investors.


When I had my baby, I stopped fundraising, but I was back at it in six weeks, with my husband taking the newborn in tow. I ended up raising $700,000, and we won a U.S. competition that got us $300,000 in start-up funds. The timing wasn’t ideal; I’m sad that I missed time with my babies, but I hear from all my friends that they’re waiting for the perfect moment to have kids: They have to have been at the company long enough, they have to have proven themselves. But I’ve learned the timing doesn’t need to be perfect. It just needs to not be the wrong moment. 


I disclosed my drinking problem to my boss

Five years ago, I was working as an associate editor at a magazine based in Yellowknife. I’ve had an ongoing problem with alcohol since around age 18, and in the North, it is normal to go out for after-work beers four nights a week. For me, it got out of hand: I was drinking so much that I was sick, coming in late all the time and functioning at half-capacity. Eventually, I said, “Okay, I need to address this or they’re going to fire me.” Thankfully, I had a good relationship with my boss — we worked closely. Plus, he was a very warm person, so I figured that being open was the best way to approach it; then he could decide what was best for the company. I’d rather people know I’m an alcoholic than think I’m bad at my job.


When we sat down, he looked at me and said, “You should never be so hungover that you’re missing work,” which was hard to hear. But he was accepting: He said he’d like me to keep working there, and to keep him updated on how things were going with AA, which I’d just started. I’d be lying if I said disclosing didn’t make things awkward for a while. And, ultimately, I didn’t end up staying — because I couldn’t keep my shit together. That was an extremely scary time, but he made me feel supported. There’s going to be the rare person who sees mental illness or addiction as a failing on your part, but asking for accommodation is something that people should never be afraid to do. It helped me a lot. 


I asked for a standing desk


Four years ago, I joined a charity bike ride. One day, when I was training for the two-day, 200-km ride, something went wrong in my lower back. I kept going, and I did the ride, but I was in so much pain. Over the next two years, the pain persisted, and I was diagnosed with a bulging disc. I discovered that when I was active on the weekends — I ski a lot — the pain usually went away, but at work, because I sit most of the day, it got worse.

I found out that I wasn’t alone: Several people in my department suffer from back problems, including people in their 20s. I saw that there was a need to do something, so I researched standing desks and sent HR a proposal, providing links on the health benefits. You never know how the company is looking at people like me — they’re always trying to save money — but I decided that I wouldn’t want to work for an organization that didn’t help its employees, and I went for it. The request was approved and my department got two standing desks. HR also approved two more for other offices. The benefits I feel are so great — I’m energized, I don’t need coffee at two o’clock anymore, I’m more alert and I haven’t been back to physio since I started working standing up.


I came out at work


In 2003, I was working in the financial security business [Osler is now the senior vice-president of the Financial Crimes & Fraud Management Group at TD Bank Group] and struggling to be recognized as a woman in a field that’s driven by men. I didn’t disclose my sexuality at work because I didn’t want to exacerbate an already difficult dynamic. I always felt there was this white noise going on among my colleagues: “Is she or isn’t she?” I tried to ignore it, but then I met my future wife, Linda. She didn’t have the slightest intention of keeping quiet about who she was, but there I was living this under-the-radar corporate life. So I started mentioning her name in conversations. Then, eventually, I told a few trusted co-workers. The minute I said “My partner is Linda,” the white noise went away. I’ve had much richer opportunities in my career because I’m able to be my whole self — like everyone else around the table — without any limitations.


I pranked my bully boss and sexist male coworkers

When I worked in London, U.K., in the late 1980s, I was in charge of marketing for one of the banks, and I had to deal with the trading side, which was mostly men. Typically, guys would go on a holiday and send postcards of naked or topless women back to the office for their colleagues to stick up on their desks. So I went to my boss and said, “I’m uncomfortable with having pictures of naked women in the trading room. I don’t think it’s appropriate — this is a business environment.” My boss said, “There’s nothing wrong with that.” I said, “You’re sure? This is exactly how it needs to be?” He said, “Absolutely.” Okay, fine.


On my lunch break, I went to the corner store and bought a few copies of  Playgirl, which were full of naked men. I tore out the images and put them all over the trading room. All of these giant dicks everywhere! And these men — these are Englishmen — were having a mental. They went rushing to my boss, who is also their boss, saying, “This is so terrible.” But I said, “No, no, no. You said this was acceptable — naked images are completely fine. Am I misunderstanding you?” Then all the images — men and women — had to come down. I put an end to it while I was there — what happened after I left, who the heck knows?

*Names have been changed at the subjects’ requests because they would like to keep their jobs.


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