Canada Day: A Celebration of Good Enough
Why Canada keeps losing its best people—and seems oddly okay with it
Happy Canada Day.
As fireworks erupt, it’s hard not to feel a gnawing sense of ambivalence. The sentiment, the symbolism, the celebration - it all feels increasingly detached from the substance of where Canada is headed. While the rest of the world barrels forward, Canada seems trapped in a comfortable kind of stasis. GDP is contracting and the best people are leaving. And yet, most of the national conversation remains distracted by symptoms - Trudeau, immigration levels, the carbon tax, pipelines.
The Culture of “Good Enough”
I grew up in Winnipeg, which might be the most Canadian city in spirit. A city where the word “entrepreneur” describes someone with a snow-clearing route in the winter and a landscaping crew in the summer. Where a career in banking means becoming a teller at RBC. Where the best-case scenario is often a stable salary, a mortgage in the suburbs, and one day inheriting your dad’s lake cabin in Kenora.
There’s nothing wrong with any of that. But when that becomes the ceiling - when the entire culture is built around preservation instead of progression - you get inertia in place of innovation.
Even in Toronto, where I spent summers interning at companies like Brookfield (on paper, the country’s most impressive corporate success story), the vibe was all too similar. While on the outside, many Canadian companies are respected global machines, on the inside, everything is plagued by the same Canadian malaise. All processes are meticulously structured. Everything is predictable. There is no sense of upward explosion, only smooth continuation. You perform, but never break form.
Why Ambition Leaves
In 12th grade (“Grade 12” for the canuck crowd), I was accepted to UPenn, and the first thing my teacher said was: “That seems like a dumb financial decision. University of Manitoba teaches the same stuff.”
It’s a small comment, but it captures something much bigger: in Canada, wanting more is often seen as naïve. Risk is treated as something to be avoided, so the people who want to chase something bigger simply leave. And when they do, no one tries to stop them.
The Canadian startup ecosystem reflects this perfectly. Canadian VCs are infamous for demanding aggressive early ownership while offering minimal strategic value. It’s a funding environment built to constrain founders rather than empowering them. There's no room for failure - which means there's no room for greatness either. And when the most ambitious founders or the most talented engineers leave? They’re told “good riddance” and “we didn’t need you anyway”.
And yet, the raw talent is staggering. Universities like Waterloo and U of T produce engineers that Silicon Valley fights over. The rigor at these schools is brutal and unrelenting - you either flunk out or emerge a god-tier engineer with the equivalent of 10 years’ work experience. A young population guided by extremely talented, well-educated students (many of whom are highly driven second-gen immigrants) has infinite potential. Toronto, if properly energized, has everything required to become a world-class innovation hub.
Instead, Canada’s become a discount labor pool. A place where American tech companies come to hire elite talent at a 50% markdown. The Bangalore of the North.
What Canada Could Become
This piece isn’t all about dunking on Canada. I’m still Canadian. I’d love more than anything for the country to turn things around.
Canada rewards continuity. It likes institutions. It trusts what’s proven. And that works… for a while. But eventually, if you don’t create new value, you run out of old value to preserve.
It’s a cultural failure compounded by decades of policy failure. A culture that says: be safe, be modest, be grateful. Don’t move too fast. Don’t talk too loud. Don’t take up too much space.
But great companies don’t come from modesty. They come from urgency, from dissatisfaction, from people who aren’t willing to wait their turn. Founders shouldn’t have to choose between building something big and building it at home.
Canada has the stability and the talent. What it doesn’t have is the cultural will. And until that shifts, Canada Day will keep feeling like we’re cheering for a house that hasn’t yet collapsed.