Messy, Flawed, Cool and a bit Playful: A Challenger Cities Future Watchlist

Why the future of urban innovation won’t come from the usual suspects and who I want to talk to next; a highly biased shortlist.

This is not a list of the ‘world’s best cities’, not is it even ranking of Challengers. It’s not scientific, it’s not exhaustive and it’s entirely, unfairly subjective.

These are ten cities I keep coming back to when looking for inspiration for Challenger Cities. Some are really well known in urbanism circles, others are not really. There’s one or two in here that I would expect people to raise an eyebrow at and wonder what I’m thinking. Some are tourism darlings, others would have a lot of people unable to place them on a map. A few are megacities, but many are firmly in the ‘secondary city’ category for their region or nation.

None of them are perfect … actually quite a few are deeply flawed. But each of them has, at some point, done something that made me think “hmm, that’s very cool”. They’ve tried things and they’ve messed some of those things up. They’ve annoyed incumbents, broken rules or sidestepped conventional planning wisdom entirely.

And in doing so, they’ve made themselves more interesting.

That’s what Challenger Cities is about. Not always celebrating the usual suspects, but noticing the ones that are on their way to becoming something, often doing so on their own terms. Whether it’s a massive infrastructure push, a cultural statement, a planning tweak or perhaps even something that was initially a bit trivial and involved some paint.

I’ve been to some of these places, while others are still on the list, one or two I’ll be going to very soon. But this isn’t a travel blog, at least not yet with my budget. It’s about creating momentum for cities that haven’t figured it all out yet, but are giving it a go, and how that can awaken some other places that probably should know better.

This is not a definitive list, it’s a living one. Cities were left off, including one with a hopefully upcoming guest. It’s a mix of scale, region, pace and politics … but by no means representative. Though if you care about where cities are headed, and what lessons might be hiding in less obvious corners of the world, these are a selection worth watching.

I want to understand what these cities have done, what they’re doing, what they regret, what they’re dreaming up next. Whether it’s a multi-billion dollar rail line or an experiment that cost a few rebellious souls a grand or two.

So here they are, and here’s how you can help tell the story. If you know someone who’s helping make one of these places better, even in small, imperfect, or ridiculous ways, I’d love an intro so we can tell their story more.

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Tirana

Notorious for: post-communist sprawl and a total lack of formal planning.
Inspirational for: painting its way back to life. Under artist turned mayor turned Prime Minister, Edi Rama, Tirana quite literally added colour to a city gripped by greyness.

It wasn’t so much policy as an act of emotion, that kinda worked; sparking a civic self-belief that’s still unfolding in public space, transport and housing. I’ve heard there’s a bit of punk energy to how Tirana operates, less committee, more courage. Even when the current Mayor is under arrest.

Even better. I’ll be there next month.

Photo by Gledisa Golikja on Unsplash

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Kaohsiung

Notorious for: being Taipei’s industrial workhorse, known more for smokestacks than street life.
Inspirational for: pulling off a design-led reinvention on the waterfront. The Pier-2 Art District is a masterclass in cultural reuse. A city that built its circular light rail not because it was the cheapest, but because it made best sense. One of a couple of cities on this list where post-industrial space is now playground, studio and gallery.

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Dakar

Notorious for: unending traffic and a state that often lags behind demand.
Inspirational for: thriving in spite of that. Dakar runs on youth, creativity and clever workarounds.

It’s a cultural capital of West Africa that’s building civic identity through fashion, art, and a little ingenuity alongside the big, bureaucratic infrastructure plans like rail and BRT.

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Zurich

Notorious for: being too perfect, too safe and coming across as a bit boring.
Inspirational for: showing what happens when everything just works. The trains, the housing, even the water fountains.

Scratch beneath the efficiency though, and you’ll find a city quietly gathering momentum with participatory budgeting, housing cooperatives and what smart governance really looks like. A reminder that boring and brilliant aren’t opposites.

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Lahore

Notorious for: pollution, congestion and a development pattern only a speculator could really desire.
Inspirational for: ambition that doesn’t quit. The Metrobus system shouldn’t have worked, really, given what stalls other projects, but it did after a very rapid build.

The digital and creative scenes are starting to punch through, often despite the system, not because of it. It’s a city of friction and contradiction with broken infrastructure one moment, fierce local pride to do something about it the next. Dysfunction sits right alongside a real sense of momentum, especially among a younger generation that’s choosing to build rather than wait.

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Bilbao

Notorious for: industrial collapse and unemployment in the ‘80s, with a bit of separatism thrown in.
Inspirational for: playing the long game. Everyone talks about the Guggenheim, but the real story is coordinated reinvention across transport, public space, housing and identity.

Bilbao didn’t just do what it did to attract tourists, it made itself worth staying in for the next generations of Basque culture.

Photo by Numan Torres on Unsplash

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Riyadh

Notorious for: oil, autocracy and top-down urbanism.
Inspirational for: sheer scale and ambition. Say what you will about Saudi politics, but Riyadh is moving fast. The new metro and bus system is enormous. The parks are grand. The construction goes on and on. Vision 2030 isn’t remotely subtle, but it’s happening anyway.

It forces uncomfortable but necessary questions about what capital and control can do when they’re pointed somewhere other than the past.

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Mexico City

Notorious for: smog, inequality and creaking institutions.
Inspirational for: being one of the world’s great cities. Full stop. CDMX isn’t ‘developing’ for it’s a modern, powerful and endlessly creative metropolis that happens to operate with constant constraint.

It’s Latin America’s commercial and cultural engine, where multinational HQs and informal street markets exist side by side. From government innovation labs to grassroots mobility campaigns, top-down ambition meets bottom-up ingenuity. The city doesn't run perfectly, but it runs because people take matters into their own hands.

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Jakarta

Notorious for: floods, sinking, chaos and a built form allergic to planning.
Inspirational for: how it survives and adapts. From GoJek to kampung-led infrastructure that handles floods, waste and public space without involving city hall, it’s a city where informal fixes often outperform formal systems.

Even with the city’s pragmatic approach to civic tech, Jakarta has built its own systems in the gaps left by government. Now, with the capital moving, the question is what happens when Jakarta is no longer the political hub?

Photo by Refhad on Unsplash

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Montreal

Notorious for: corruption scandals, endless construction and the winter cold.
Inspirational for: refusing to be boring. Montreal is one of the few North American cities that feels like it enjoys being a city, rather than wanting to be a series of suburbs with a downtown core.

Montreal takes culture seriously, throws street festivals in winter and has more fun with public space than most places manage with twice the budget. It doesn’t ask for permission to be weird, it just accepts that it already is, and hopefully always will be.

Plus I live here now. So there’s that.

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But what about the cities struggling to be Challengers.

We should also pick a few cities that are failing to challenge, places that are a bit comfortable. Places that should be charging ahead but have instead curled up under the weight of process, politeness and a healthy dose of political fear.

They have the wealth, the brains, the narrative … but they’ve lost the will.

Toronto

Obvs! Talks a big game, but acts small. A city with the population of Chicago, a place that should have taken the mantle on as being North America’s genuine second city … but instead has all the urgency, and the rizz of a compliance committee. It could be extraordinary, but it’s been swallowed whole by its own bureaucracy. The result is a city that’s stuck debating bike lanes while affordability, mobility and culture quietly suffocate.

Dublin

Ireland’s global darling, struggling to house its own people. A tech-fuelled boom town that’s pricing out everyone who makes it interesting. Dublin’s crisis isn’t just about housing, it’s about courage. Policy has been slow and scared of upsetting anyone, all while buildings in prime locations literally collapse into themselves. .

Brasília

The architectural fever dream that became a planning cautionary tale. Built to be visionary, Brasília ended up being a city for no one. Over-zoned, over-designed and disconnected, literally and metaphorically, from the country it governs. A brutal reminder that beautiful maps don’t guarantee human cities.

An extra honourable mention here might be Brussels. The administrative capital of Europe somehow forgot to become a great city, despite the chocolate, mussels, frites, waffles and beer. A place that could be inspiring, but something just doesn’t really do it. Even with all those political types.

What I’m Looking For

I want to speak with people who are changing these cities, not just talking about it. That includes the urbanists, but also developers, architects, mobility operators, retailers, startups, cultural programmers, politicians and civic entrepreneurs. People inside and outside the system, public and private. People building things as well as breaking things.

If you know someone in one of these cities doing something that deserves attention, please send them this way because I want them for a future episode.

Cities don’t change with white papers, as much as I sometimes wish they could, they need those people that do something that might be small, is bold, a bit naughty or perhaps somewhat unreasonable.

Let’s find them.

To being Challengers.