At 17, I left high school to care for my adopted mother as she was dying. By the time I earned my diploma at 22, I was raising a daughter of my own and trying to imagine a better future for us both. With a toddler at home, I enrolled in a radio broadcasting program—drawn to the energy, creativity and chance to connect with people from all walks of life. When I graduated, however, the media business was in trouble. Jobs were disappearing and the path forward felt uncertain. At 25, I let go of my radio dream and took a gig answering phones for a telecom company, chasing something more stable.

I worked my way up from $18 an hour in customer service to $50,000 a year running a retail location. I loved my team, and I liked the dynamics of retail. I was hitting targets, managing staff, solving problems. No two days were ever the same. On paper, all of this looked like success. But the unpredictability that made it interesting also made it exhausting. There were constant crises: customers in the middle of mental health episodes, people filming us and posting accusations online because we couldn’t meet impossible demands—like delivering 45 iPhones within the hour. Once, a woman stumbled in drunk at opening time and threw up all over the floor.

More than a decade into the job, I started to feel stuck. I was raising my daughter, who was a teenager at that point, as a single mom. My rent was $2,000 a month. I was still carrying student debt. I was living paycheck to paycheck, and the pressure never let up. Some weeks, I’d be standing in a store full of the latest iPhones, wondering how I was going to pay my own phone bill. And even though I was good at the job, I couldn’t shake the feeling that I wasn’t moving the needle on anything that mattered or building something tangible.

Right around then, in the fall of 2018, a friend went back to college. When she talked about it, she was lit up and excited in a way I hadn’t felt in years. I didn’t know exactly what I was looking for, but seeing her so energized seemed like a sign.

Centennial College was the closest college to my home in the northeast area of Toronto, so I started scrolling through their course listings online. I stumbled upon a two-year diploma program in special event planning. Something clicked. The birthday parties I threw for my daughter were never fancy—we didn’t have a lot of money, so I DIYed many of the decorations—but there was always a theme. One year, she dressed up as Hannah Montana for Halloween, which inspired a........

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