Intersections are never the same

Are there any intersections in the city that get you thinking, feeling or reflecting? 

Today I was standing at the intersection of Bay and Dundas Streets in Toronto. That’s one of those intersections for me. 

Since this newsletter is called The Intersection, it’s time to share something about that very idea.

Street intersections mean different things to different people, but what’s consistent about intersections is that they’re never static. An intersection transforms over time — a café closes, a condo goes up, new storefronts appear, or maybe the streetlights change. Even the billboards shift or entire sections get blocked off for construction. Intersections are always in motion, much like the people crossing them, the cars passing through, or the changes happening around us.

Every time you look, it’s different.

The Evolution of an Intersection

Years ago, I had my studio in a run-down building at Bay & Dundas — a building that still has one of the last remaining elevator operators in the city. No air-conditioning, but a lot of character. We called our space Now Common and built it into more than just an office — it became a studio and community hub. We even rented desks to fellow entrepreneurs and ran Training Tuesday meetups.

I spent countless hours at that intersection — early mornings, late nights, and everything in between (including lots of bubble tea runs).

During the day, it’s filled with corporate workers and students from Toronto Metropolitan University. But at night it’s completely different, with energy spilling over from the nearby Yonge-Dundas Square (also changing, being renamed Sankofa Square).

Just like the space itself, the people and energy there have changed a lot over the years. 

Reflecting Society

Intersections are a metaphor for society. People come and go, constantly evolving and changing, while the structures — the systems — remain and adapt much slower. Laws and government always seem to be playing catch-up with how people live and interact.

For years, I frequented that intersection for agency-related meetings. Now, my focus has shifted to conversations about social entrepreneurship and innovation. 

Social Innovation and the Future

A few months ago, the Social Venture Zone hosted an event on the future of Toronto’s economy, particularly around social enterprises. It was held at the Centre for Social Innovation, where I’m also a member through The Good Growth Company. At this event, I got to hear from social entrepreneurs, investors, and other partners about their success stories. The variety of voices in the Ontario social innovation landscape is incredible — business leaders, nonprofit founders, government representatives — all working together to create a better future. 

This work doesn’t happen in isolation. It thrives at the intersection of business, nonprofit, and government sectors. Collaboration is a given. 

Walking the Talk, Literally

I had the chance to go for a walk with the head of the Social Venture Zone, someone who has built an incredible career at the intersections of government, business, and nonprofit. He’s consulted with countless clients on social innovation while co-founding and directing Canada’s leading social entrepreneurship incubator. Our walk took us through these same intersections. 

I left from the conversation feeling more connected than ever to my communities, to the work, and to the potential for even greater impact. These intersections — literal and metaphorical — remind me that by leveraging our collective strengths, we can create meaningful change, locally and globally.

Today’s a reminder of the power of working at the intersections. It’s where the magic happens, where ideas collide, and where progress is made. 

More and more, that’s where I get to spend time. 

Here’s to the intersections — of people, ideas, and change.