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Katie Taylor is the former CEO of Four Seasons Hotels and the first woman to chair the board of a Big Five bank.Sam Singh/The Globe and Mail

My first job was as a banquet waitress. We had to work as a team, and we worked in service of people. I’m a classic extrovert, so those kinds of roles were the ones I found easiest to do. They didn’t deplete my energy.

I wasn’t someone who went to law school because I wanted to be lawyer, but I ended up at Goodmans. I cycled through every department and hated them all. I ended up in corporate securities and loved the excitement of it.

When the market crashed in 1987, we went from working 18 to 20 hours a day to having nothing to do. Being a kid with no net to fall back on, my main objective was to stay employed. So I said to my boss, “What would you think if I went to the OSC and learned the other side of the Street?”

It was an unbelievably exciting time for the OSC, but then my mentor from Goodmans asked if I wanted to be No. 2 at Four Seasons. He said, “You’ll have so much fun.” And I got to work with him again. People rarely quit and join companies. They quit and join their bosses.

It was one of the more fantastical career experiences: an iconic founder of an unbelievably successful global brand. I was never more than 50 paces from Issy’s office. And I was general counsel, so almost everything ran through my office.

I had a seat at the table, which was mostly men. They were all, including Issy, interested in developing me as a more rounded, more successful leader.

Like any young mother, it was hair-on-fire most of the time. I had an incredible support system, but there’s no replacement for the mom. That’s why I do a lot of talking about why there’s no work-life balance; there’s only work-life integration. You try to fit your lives together the best you can.

We’d taken Four Seasons private in 2007, and by 2013, the new investors were looking to have a larger role in running the business. In the circumstances, my departure – though sudden – was not too surprising.

I’d spent years on the road, sometimes 150 or more days a year. So never going to Pearson again seemed like a good thing.

I went out with Phyllis Yaffe, who’d been CEO of Alliance Atlantis. I asked why she’d hung up the skates. And she said, “Because I had the extraordinary luck of working for the best company in the best industry with the best people and the best team. The chances of repeating that twice in one lifetime is close to zero, so I decided not to set myself up for disappointment.” I went home and told my husband, “I’m not being a CEO again.”

When I became the first woman chair at RBC, it was zero out of five at the Big Banks, then it was one out of five. Now it’s two out of five. I call that progress.

If you look at the composition of the largest companies in Canada, most have a very diverse slate of directors. Where things have not progressed at nearly the pace I expected is on the executive and executive pipeline side.

Take more risk in your 20s. Pivot, pivot, pivot. Because once you’re in your 30s, the cement has formed around your feet.

We’re in a relationship deficit. People are spending less time together. Get out there and get connected. Over time, that’s going to matter hugely.

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