Back to the Future Again?

Reflections on Leaving Toronto After 25 Years

Twenty-five years ago, I was living on 48th Street on the East Side of Manhattan. I was working at a major ad agency on Madison Avenue and had just clinched a significant win—our team landed the contract to build the first website for Lipitor, the then-new statin drug for treating high cholesterol. We’d pitched hard against the incumbent AOR (agency of record), and the victory felt sweet.

It was the summer of 1999, and while I was savouring this career milestone in the heart of the advertising world, I was also preparing to leave New York City—and the Jersey Shore, where I grew up—to start a new chapter in Toronto, Ontario. The move was fully personal. I had met someone online a couple of years earlier, and what began as long weekends between New York and Mississauga became something more grounded. I liked Toronto. The city felt open and evolving, and I was drawn to the rhythm of life there. My family wasn’t that enthusiastic, and my friends made fun of me because I had New York City to meet people, but I had to go elsewhere.

Now, as I prepare to leave Toronto and head to Florida, I can’t help but feel a strange sense of déjà vu. That same murky cocktail of excitement, uncertainty, and hope that swirled around me in 1999 has returned.

But this move carries different tones. This time, I’m not chasing a job or a relationship—I’m moving in with my father. It’s a decision rooted in love and responsibility. We’ll share space and time in a way we haven’t since I was a teenager. But I have been staying with him over these ten years, and lived there when my mother Audree was ill and needed extra help caring for her.

Looking back on these almost 25 years in Toronto, I feel grateful. This city became my canvas for reinvention. I taught, created, and built meaningful educational experiences.

I worked for a dot.com at first in Toronto. It was the heady days of the late 90s, and lots of things were being thrown against the wall to see if they stuck. My first boss was fired because he got a vendor pregnant. We bought other competitor sites and nobody knew why. The management team went this way and that, but I hired a wonderfully smart group to handle content strategy, and we lumbered on as a team. Everybody had a cell phone and a landline for no clear reason, and nobody knew what their job really was. We had senior meetings to discuss the lobby flooring. One day, I was asked into the CEO’s office, and he proudly showed me the Windows desktop icon shortcut, and I realized he was an idiot in management consulting drag, and I quit. It was the final straw.

Then it was a big job at Nortel. I got access passes to the head office. We were an army. I called on major Telcos. I worked on Data Centre designs. I had access to engineers proposing fibre optic networks and meetings to discuss media usage in these builds. It was another level of growth. I loved how scary and demanding it was for a kid who caught minnows with his brother for gas money before college. They set me up with a home office and shipped a workstation and a $2100 office chair, which I am still sitting in as I type this post. And not too much later, the company imploded. 349 people on my team were fired on a conference call in 2001.

Next for me was Saatchi & Saatchi, which as the next level of Ad agency. And it keep going, with Cineplex and other roles for more than 20 years. I love to work. I love to learn. I don’t have any desire to retire at all. Toronto gave me more than professional success. It eventually gave me resilience, a deeper understanding of myself, and the long winters further taught me patience and planning. It also gave me stories—so many stories.

Now, looking ahead to my move to Florida, I feel something stirring again. A creative energy. A lightness. I want to write more personally, share more openly, and explore what it means to teach and learn in this next phase of life. To everyone who’s been with me on this journey: thank you. I’m bringing everything I’ve learned with me. This isn’t an ending. It’s a reset. A new chapter in an ongoing story.

And just like in 1999, I feel ready.