Sheelagh Whittaker’s new memoir chronicles a lifetime of breaking boundaries
Women Leaders24.03.2025
After decades of pushing boundaries and breaking barriers, Sheelagh Whittaker is finally taking a moment to reflect.
An accomplished businesswoman, Whittaker has made a name for herself by successfully conquering the corporate ladder, landing CEO positions at major companies like Cancom and EDS Canada.
Her impressive resume, and the incredible journey that got her there, is the catalyst for her new project: a memoir entitled Through the Glass Ceiling: Reflections on Feminism from the C-Suite.
In it, she looks back on her trailblazing career, sharing stories from the boardroom, navigating the highs and lows of leadership as a woman, and the personal lessons she learned along the way.
The Honest Talk had a chance to chat with Sheelagh about her career, the new book, as well as her thoughts on the challenges women are facing today and where we can still look for hope in the darkness.
Q: Sheelagh, you’ve had quite a career! In fact, you were the first woman to ever be CEO of a company listed on the Toronto Stock Exchange. How did that feel?
Sheelagh: What a good question. I don’t know if anyone ever asked me that before! It was exciting. I felt proud and happy to share that with my family. Almost like, “Look what mommy accomplished!”
Q: What struck you the most once you were on the other side of that glass ceiling?
Sheelagh: I think women who make it to the top often carry a lot of guilt. I would talk to groups of senior women, and I always came away with this feeling that society was holding them back because of the guilt they carried, which was often tied to motherhood. And that can be really difficult.
For me, I was a mom and loved my kids. But I realized early on that I needed to work, that my passion was my career. I recognized that might mean I wouldn’t win a “Mother of the Year” award, but you find a balance that works. And you don’t let that stop you from aiming higher.
Q: Do you think that kind of glass ceiling still exists? Is it the same, or is it different these days?
Sheelagh: I thought we were making real progress. I think a lot of us did, unfortunately. But now you have these anti-democratic initiatives rising that are somehow always synonymous with relegating females to more junior roles. So that’s scary.
I was hoping that I was in the more revolutionary period, that we were working on language and saying our bit. I hoped we had entered the evolutionary stage, where we weren’t fighting so much as building on progress. I still have hope when I look at my daughter, who is a proud Crown prosecutor, or my granddaughter, who is taking engineering at Dalhousie. To me, that’s a sign that we’re getting there and making progress, but I am still afraid of these other forces at play.
Q: You touch on a lot of these ideas in your new book, Through the Glass Ceiling: Reflections on Feminism from the C-Suite. What’s your relationship with feminism?
Sheelagh: It’s very, very deep. I was lucky to be in the initial ferment, where we were trying to work out what we wanted as women. Then, I was interested in the social change that we needed to create an environment where people were dealt with more as individuals.
I was pretty interested in the role that language plays, and still am. They used to laugh at me during board meetings because they would say, “It’s going to take us 27 man days to do this..” or “manpower,” and I would always reply with, “We use staff days.” Those small changes in vocabulary can make a big difference in people feeling included. Admittedly, I’m a little sad these days because there’s a lot of rolling back on the language side, and it’s incredibly disappointing to watch.
Q: What inspired you to write this book?
Sheelagh: It was back in 2020, which was not a great year for the world. My adopted son and my husband had both died and the following year, I had to undergo surgery. I had a fantastic caregiver during that period, and we chatted a lot about her life and about my own. She’s the one who said to me, “You should write these stories down.” And she went out and bought me a scribbler, gave it to me, and told me to write down my story. So I did!
Q: I love the idea that you were physically writing down your stories in a notebook! What was that experience like to look back on your career and reflect on your accomplishments?
Sheelagh: You know what? It had an unexpected and wonderful dimension, actually. When you’re living it, you’re not revelling in it. It goes back to our earlier conversation about how I felt when I became CEO. You don’t actually sit in that moment and think, “This is pretty amazing!” But this enabled me to do that, and it was wonderful to think back on those opportunities that I had.
Q: What was your biggest takeaway from that? Or the biggest lesson you hope others take away from your story?
Sheelagh: It’s to be yourself. When I think about the successful women that I know, and I’ve been lucky to know many, they are natural, stand up for themselves, are well qualified, and know it. And I don’t mean that in a stuck up, or aggressive way. I just mean they are real people who manage or lead in a way that is consistent with who they are outside of work.
I genuinely believe that if you keep on acting as if you expect to be treated equally, it’s much more difficult for somebody to put you down or relegate you. So, never be afraid to just be yourself!
