Memoir: I was a 50-year-old Bay Street intern

Memoir: I was a 50-year-old Bay Street intern

In 2005, I left my finance job to raise a family. Nearly a decade later, I returned to Bay Street

(Illustration: Anastasiya Milova)

I’ve known since I was a teenager that I wanted to work on Bay Street. I’d always loved math, but when my high school economics teacher played a stock-trading game with us, that was it—I was hooked. After university, I found a management-training position at Midland Walwyn, an investment dealer in Toronto, and, while still earning my MBA at U of T, joined the company’s investment banking group.

It was 1992, and I was one of the first female investment bankers at the firm. I was often the only woman in meetings. Client events, such as golf outings, seemed designed for men. But I refused to be sidelined: I worked hard to earn respect, and I bought a set of clubs, hit the driving range and learned how to play.

Several years later I joined an asset management start-up. I stayed for seven and a half years while the company’s assets grew from $100 million to $29 billion. I often worked 60-hour weeks only to slog through more files on the weekend. Occasionally, I’d wonder if I was missing out on life outside Bay Street, but I loved my work.

Along the way, I met my husband, an investment banker, and we had a son. When my baby was still less than a year old, I found out the company was being sold and I needed to cut my maternity leave short. I started waking up before my son, logging full days at the office, then heading home in the early evenings to spend a few hours with him before bedtime. My life was a blur of phone calls, dirty diapers and early mornings at the office.

A year and a half later, the deal was finalized and I learned I was out of a job. A few years earlier, I would have been devastated, but the more I thought about it, the more relieved I felt. After 17 years on Bay Street, I was burnt out. I decided to try full-time parenting. It wasn’t a tough decision; in my mind, I’d be back to work in no time. I approached stay-at-home parenting with the same all-in attitude I brought to my career. We had our second child, a daughter, and I joined the parents’ council at my son’s school and volunteered with his hockey club. At one tournament, I helped to feed 3,000 people, chopping 100 pounds of onions in the arena kitchen. Parenting, like finance, was a non-stop gig.

Eventually, I began to miss Bay Street, but I couldn’t fathom going back to work with two young children. When a tempting opportunity popped up six years after I left, I was intrigued but didn’t feel ready. I wondered if I ever would. I didn’t know how to re-enter the capital markets industry or whether an employer would be interested in the skills of someone who’d spent so many years away.

When my daughter was finishing kindergarten, I pushed those doubts aside and asked my family how they’d feel if I started working again. Their resounding response: go for it. Before I even started an official job search, an acquaintance told me about Women in Capital Markets’ Return to Bay Street program. It’s an internship designed to help women transition back into the business world after an extended absence. After attending an info seminar, I convinced myself to apply. I spent the July long weekend assembling my resumé, hunting down references and drafting a cover letter. I even hired an employment coach to help me practise for the interview. It paid off: at age 50, I got a four-month internship at BMO Capital Markets.

I was excited to be back but anxious about where I’d fit in. After feeling rusty at first, I quickly regained my confidence. I was an intern by title, but I was treated with respect and assigned challenging work. There was no fetching coffee or answering to assistants of assistants; instead, I worked on a variety of regulatory projects, participated in team meetings and reported to senior executives. I still remember, near the end of my internship, sitting in a meeting with the president of capital markets, walking him through a presentation I’d made. Once I’d finished, he gave me great feedback. I began to see what I could offer at the office—and realized my family was doing just fine.

After work, I spoke to whoever would meet with me, re-familiarized myself with capital markets and scoped out job opportunities. Then, when the internship ended, BMO offered me a full-time position that led to my current role in investment banking. I’m no longer answering directly to clients, so the job affords greater flexibility. The hours are lighter, and I can work from home when I need to.

In my first stint on Bay Street, I immersed myself entirely in my work. When I had kids, I dedicated myself totally to them. Now, for the first time, I feel like I have balance. I don’t know if parenting has made me better at my job, or if having a career has made me a better mom, but I know I’m happy. I get to do work I’m passionate about and spend time with the family I love. My husband and I have a membership at a golf club and are teaching the kids to play. My daughter is still young, but I figure it can’t hurt for her to get a head start.

Barbara Glassford is a director at BMO Capital Markets.