About a year ago, I was in Toronto, feeling stuck.
Not just physically, but mentally, but stuck in a city that seems almost chemically resistant to innovation, creativity or even a bit of novelty. A place that talks a big game about being "world-class" while making it nearly impossible to build a home, operate a coherent transportation system, or take a risk without running into a ten-year planning process and a public consultation full of people who've already decided to attend because their natural reaction to anything new is ‘no’.
So I started this podcast.
I didn’t really know where it would go. I had a handful of followers and a big question: Could I find the people who were trying to make their cities better, even if they weren’t the ones usually invited to speak on stage?
And that became the first series, Challenger City TO. Toronto-focused, born of frustration, scrappy, earnest. A bit of a rant with structure. I talked to unconventional voices in the form of accidental urbanists, creative schemers and people trying to fix one tiny thing that no one else seemed to care about. And then I moved to Montreal which was a bit of a reset. The podcast moved with me, becoming a bit broader, bigger, hopefully a bit more ambitious.
By Series 2, we’d opened the lens. Cities across Canada, across the Atlantic and into unexpected corners like rural bits of Texas, oh and Walthamstow. I found myself having conversations I didn’t think I’d get to have. People started reaching out with “Can I be on the podcast?” or “You should speak to this person”. I even heard from a couple of CEOs of big Canadian companies saying, “That episode really hit—we’re working on something related.”
It’s grown into something more than I thought it would.
This isn’t just a podcast anymore. It’s starting to feel like a bit of a playbook writing itself, and a sketch of a manifesto is in my mind. A slightly cheeky rebellion against the slow, sad drift toward civic mediocrity.
What I’ve learned along the way is the most interesting cities aren’t the ones with the best plans. They’re the ones that are willing to at least be less wrong, faster, and in a more interesting way. They try things, make mistakes and build momentum instead of waiting for permission.
And while I still love a good urbanist fairy tale from Amsterdam or Paris, I’m much more interested in the cities that no one’s watching. The ones doing something strange with small budgets and big imagination. The ones whose greatest strength is that they haven’t yet convinced themselves they’re already doing everything right.
So that’s where Series 3 is going.
This season will take us to some new places like Dakar, Rabat, Tirana, Gdańsk, Copenhagen. The last one of those is a ‘poster child”, sure. But I’m after the underdogs, the overlooked, the hopeful and even the glorious failure.
And the question I’ll keep asking at the end of each episode is the same one I always do: If you had a magic wand, what would you do?
And nearly every time, the answer isn’t fantasy. It’s something we could do tomorrow. If we just decided to stop waiting for a mayor, or a minister or a memo from the city manager. If we stopped pretending progress has to come with a perfect plan. If we started with the smallest possible action that points toward the biggest possible future.
So as we kick off Series 3, here’s what I’d love:
If you’ve been listening, or reading along, thank you.
Now: send it to someone else.
Rate it. Review it. Forward it to the friend who thinks their neighbourhood could be more interesting. And send me stories. The places you think deserve a spotlight. The cities being interestingly less wrong, the people doing things quietly brilliant or at least applaudably brave.
Because we’re not Amsterdam. That’s fine, because we have the opportunity to be anything we want to be.
Let’s go find the next ones.
Series 3 starts now.
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