When Hayden Clarkin, known widely on social media as The Transit Guy, joins a conversation about urban transit, you can expect honesty, insight, and just the right amount of provocation. Hayden doesn’t shy away from calling out inefficiency and dreaming big, actually that’s why I thought we needed to chat about Challenger Cities following a recent Substack post from him about how we need a new agenda for fixing our cities.
Our chat explored where North America’s cities are failing, why they’re failing, and more importantly, how they can rise to the challenge.
A Broken System with Deep Roots
For Hayden, the problem starts with history. "Canadians and Americans have really never seen public transit work since at least the Second World War," he explains. It’s a sobering point. Generations have grown up thinking transit is inherently flawed, while cities like Zurich or Amsterdam leave us wondering, “Why can’t we have that here?”
The answer lies in what he calls the "chicken or the egg" problem of transit. "We need to get really great transformative transit so that people will ride it, so they’ll support it, and we can compound on it." Unfortunately, decades of car-first planning dismantled the robust systems we once had. "A lot of the time, I’m just talking about restoring what we had, not changing anything drastic here."
The Governance Trap
But there’s more to the story than cars. Hayden pointed to governance and bureaucracy as a major hurdle. He recounted the infamous “La Sombrita” project in LA—a metal sunshade at a bus stop so small it provided no actual shade. "It was designed to scapegoat all the processes so that it could just be fixed on a pole. The city was patting itself on the back for skirting around its own broken regulations instead of fixing them."
And it's not just LA. Whether it’s high-speed rail in California or bike lanes in Toronto, processes seem designed to obstruct rather than enable progress. "If the second-biggest city in the world’s biggest economy can’t build a bus shelter, why are we talking about Medicare for All?" he asks pointedly. It’s a warning for those who think big ideas can ignore small failures.
The High Costs of Inefficiency
For Hayden, inefficiency is at the core of North America’s transit woes. "The MTA spent $30 million on a staircase. In Milan, that same money could build two and a half subway stations. What are we doing here?"
We contrasted this with how Europe approaches infrastructure. The French build TGV networks incrementally, with the budget dictating how far they go. In the likes of the UK, US and I really hope not in Canada, we dream up big high speed rail projects and start lopping pieces off when costs spiral. By the time they’re done, the original benefits have been unrealised, or what they were supposed to be has been forgotten.
Hayden doesn’t hold back when it comes to high-profile failures, like California’s high-speed rail project. "It’s an unbelievable project and absolutely should happen. But the way it was designed and governed has been an unmitigated mess."
The Role of Culture and Experience
Hayden pointed out how shared experiences can open people’s eyes to better possibilities for infrastructure. He used the example of airports: "There’s such a shared experience in America around flying. And people don’t get that with passenger rail because it’s just not something we really have in a way that’s transformative."
It’s a really important thing, because transit is a creative act. Once it’s there, it changes how you behave in ways you might not have previously imagined. I often use this example in Italy where high speed trains open up previously impossible lifestyles, where you can live in Bologna, go to Florence for lunch, work for a company based in Rome or Milan, and frequently go to the opera in Verona. In a world before fast, frequent and affordable rail, you wouldn’t have dreamed about such mobility and way of living.
He also emphasised the impact of seeing world-class systems firsthand. "I always bring up Disney World. Millions of people visit this walkable Main Street every year and think, ‘How cute is this!’ without realising it’s based on a real town—Marceline, Missouri. We used to have these kinds of places, and now they’re theme parks. Why can’t we have that here again?"
Building for the Future
So what’s the solution? For Hayden, the answer lies in a bold, coordinated approach that prioritises vision, execution and trust-building.
"We need a national vision for transportation—something that shows what America can look like in 2040. Then reverse-engineer it, just like Switzerland does," he says. Switzerland’s model of planning decades ahead, with detailed clock-face schedules and infrastructure to match, exemplifies what’s possible when a country commits to seamless integration. It’s not about dreaming up isolated projects; it’s about crafting a connected, future-proof system.
But a grand vision means nothing without effective implementation. Hayden is adamant that politicians need to know their limits: "Politicians shouldn’t be making policy; they should be seeking it out. There are so many good bureaucrats and experts with ideas. Let them lead, and focus on getting it done." He sees the role of elected officials as enablers, clearing the way for subject matter experts to deliver results.
For Hayden, the crisis in North American cities goes beyond transit—it’s about the erosion of public trust. "People don’t care about policy; they feel delivery," he emphasises. A grand infrastructure bill or sweeping policy announcement won’t matter if it doesn’t translate into tangible improvements in daily life. "If we can’t deliver something as basic as a bus shelter, why would people trust us with bigger things?"
The path forward isn’t easy, but it’s possible. Hayden points to historical successes as proof: "We’ve done it before, and we can do it again." From building comprehensive streetcar networks in the early 20th century to constructing world-class subway systems, North America once led the way in transit innovation. The question, he warns, is whether we are willing to rediscover that ambition. "Are we bold enough to rebuild, or will we keep patching the cracks until the system falls apart?"
Hayden leaves us with a challenge: to stop thinking incrementally and start thinking transformationally. It’s not just about moving people efficiently; it’s about inspiring them to believe in their cities again. And for that, we need more than ideas. We need action.
To being Challengers.
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