I have a soft spot for first conversations. They’re usually messier and more speculative, because we’re still fining out feet, working out what to say. When I recorded the very first Challenger Cities conversation about eighteen months ago, I didn’t really have a format, a full thesis, or even the faintest sense that this would turn into a sustained project. I mostly had a feeling that Toronto felt off, and a suspicion that the usual language from the standard urbanism scene wasn’t getting through.
My first conversation was with Jasmine Palardy, and in retrospect she wasn’t just my first guest, she was a key instigator too. She egged me on, dragged me further into urbanism than I intended and pulled me into the WRLDCTY orbit where many of these conversations found a wider context. Looking back now, after dozens of interviews and an awful lot of walking, watching, travelling, noticing and stewing about how places actually work, or don’t, it felt right to loop back. Not to repeat the conversation, but to consider what has shifted.
Eighteen months ago, urbanism still felt like something you opted into as a field or a discipline. Now it feels less elective, as more people seem to have arrived at city questions through unconventional paths, often without meaning to. Jasmine points out how she’s “… noticed more and more people who never thought of themselves as urbanists suddenly becoming very interested in how their cities are designed and how that affects them. Designers, people from healthcare, engineers. They’re asking, ‘What is my role in shaping the future of my street, my neighbourhood, my city?’”
These people who spent years working on systems that were supposedly abstract, suddenly finding themselves fixated on streets, pavements, transit stops, rivers, main streets … not because it’s fashionable (is it!?), but because the friction and frustrations can’t be ignored … has to be a reason for optimism.
Jasmine described it neatly when she talked about “accidental urbanists” which is also how I’ve described myself. People who didn’t wake up wanting to shape cities, but who came out of the pandemic noticing, perhaps for the first time, how much the built environment was shaping them. When your world shrinks to the size of a few blocks, you start to feel every bad decision in your feet, your shoulders, your nervous system. You start asking why traffic is so awful, why public space feels hostile, why it’s so hard to do simple things well … think irritations over ideologies.
That irritation, I think, is where most meaningful urban change actually begins.
Somewhere along the way, urbanism became overly associated with control, though Jasmine, like a friend over text this week pointed out the term itself. “Urbanism is a funny word, like innovation. It means nothing and everything at the same time, depending on who you’re talking to. And that means there’s a responsibility for those of us who care about cities to be open to messiness, and to not assume we’re the ones in control,” she said. As someone who has defined his career first in innovation, and now in urbanism, I feel a bit seen.
With masterplans, permissions, frameworks and the idea that good cities are the result of sufficiently detailed foresight, consultation and planning. Then when you look at the places people actually love, that story falls apart very quickly … nobody has really planned their way into affection for the places we care about most.
Jasmine frequently brings up the people she calls informal city builders, and there’s maybe 10-30 of them in every city. Not planners or architects, but the butcher who opens a shop so good people cross the city for it, the baker who unintentionally anchors a neighbourhood, the person who takes over a downtrodden theatre or warehouse with more conviction than capital and somehow makes it work. These are rarely the people celebrated upfront as you don’t make them, you often can’t predict them and what they get up to is too idiosyncratic, unusual, or risky to defend up front before you can post-rationalise it. Cities are very good at retrospectively claiming them once they’ve succeeded though, but according to Jasmine … “Our job isn’t to manufacture them. It’s to create the conditions where they can survive long enough to succeed.”
What they are not very good at is creating the conditions for these people to survive long enough to succeed in the first place.
This is where complexity and complication quietly diverge. Cities are complex, no question. We can point to lots of things that cities must enable, so fire trucks need to turn, water needs to flow, safety matters and we’ve got all sorts of effective and ineffective requirements for such things. We’ve layered that complexity with an extraordinary amount of professionalised complication, often justified less by outcomes than by accreditations. Rules that began with care and good intentions harden into obstacles when they meet the real world.
Simplicity can be seen with suspicion, and intuition might be seen as naive. Anything that can’t be defended in advance is basically treated as irresponsible. Professions have a habit of over-complicating things because complication validates their importance. The problem is that cities pay the price.
Somewhere in our conversation, a comment from another conversation resurfaced. The idea that urbanism, in the current climate (have you seen the news!?), is a luxury belief. This is something at the time that I imminently pushed back on, though Jasmine gave it a little more time.
It probably does contain a partial truth, because talking about cities can be a luxury, as can some of the fantasy like imagination of alternative futures we kind of know will never come to pass. But living in a city that doesn’t work as well as it should, or doesn’t really work at all, is surely not a luxury belief.
What became clearer through the conversation is that the real luxury isn’t imagination, but control.
“I think it’s a luxury to be the one in control,” Jasmine said, continuing, “and maybe that’s why we struggle with cities. Because letting go feels risky, even though we can never predict everything anyway.” When you sit with that, a lot of behaviour snaps into focus. The obsession with certainty, the discomfort with experimentation, the desire to know, in advance, exactly what will happen, on what timeline, at what cost. The fantasy that cities can be fully specified before they are lived in.
They can’t. They never have. Never will.
This is why the places that feel most interesting right now are often the ones that ran out of certainty first. Calgary came up repeatedly, not because it’s perfect … I have long used Calgary as my urban scapegoat … but because it was forced to confront its fragility early. Skyrocketing office vacancy in a downtown office based monoculture and infrastructure debt that surfaces itself as water mains burst.
Ironically, all in a city of engineers faced with problems that could no longer be deferred.
Jasmine suggested Calgary is like a teenager … (others have used the same analogy for Toronto) … naive, overconfident, but malleable enough to take risks (that bit Toronto hasn’t quite got yet though). When denial stops being an option, because your downtown is dead and one morning the water was off … experimentation becomes possible. Office-to-residential conversions, cultural anchors and infrastructure triage … also aided by the big flood not so long ago. Not because they were trendy, though they are now, but because something had to give.
What’s telling is that much of the progress happens not at the scale of the whole city, but at the scale of districts and neighbourhoods. Cities are unwieldy beasts after all, and election cycles, budget cuts, political theatre all add friction to the process. So you focus on districts as they are smaller, more legible and more forgiving of trial and error.
“Cities are living ecosystems with competing mandates. When people start to understand that complexity, they become better advocates and better neighbours.”
This is where municipal development corporations, BIDs/BIAs (pick your term for business improvement groups) and community real-estate experiments start to matter. They aren’t silver bullets, but are places where learning through success, failure, or a bit of both, can actually happen.
It’s also where an uncomfortable absence becomes visible when you notice that developers and financiers hold a lesser representation the room at urban conversations. Not because they don’t care, but because they don’t need to be, as it is they who hold the capital, so they can wait o r arrive later as catalytic investors once something already feels inevitable.
The irony, of course, is that the things which make places work are almost impossible to model in advance. Suggesting that a neighbourhood will go viral if it got a really good butcher will get you laughed out of the room. Six years later, once the butcher has attracted the baker, the restaurant, the foot traffic, the housing demand and eventually the transit upgrade, everyone will nod knowingly and explain why it was obvious all along.
Downtowns and urban centres are currently living inside this contradiction. Most cities spent the past few years talking about reimagined business districts and experience economies. Many strategy documents were written, but far fewer places have actually been programmed. Jasmine pointed out how the strategy is one thing, but someone still needs to hold the budget for making a place feel alive and referring to Ashley Chandler and her work programming Bentall Place, under Hudson Pacific Properties in Vancouver.
“Ashley and her team programmed the podiums of those buildings and their plazas two thirds of the year. Two thirds. They specifically invested in taking what would have been retail space and making it plug-and-play for vendors, events and temporary pop-ups. They recognised it might take years to hit the books in a meaningful way, but they took that medium to long-term bet, and it’s paid off.”
What sits beneath all of this is a growing weariness with copy-paste urbanism. Being the Silicon Valley of the North, the Copenhagen of the South, the Berlin of somewhere. It’s lazy, and people can feel it. What they’re craving now isn’t best practice, but tangible specificity. Places that feel like somewhere, not everywhere else.
Which is why Jasmine’s magic wand answer is a fun one. For it’s not really a megaproject or more masterplanning, but an ecosystem hub, akin to a Canadian equivalent of Copenhagen’s Bloxhub. A place that backs interesting people working on the future of cities before their ideas are tidy, defensible or respectable. Think an innovation of ways, rather than things.
Eighteen months on, that feels like a good through-line of Challenger Cities. The work isn’t about control, perfection or grand visions that survive contact with nobody. It’s about loosening the grip just enough for the right kinds of people to act, noticing what’s already working and getting out of its way to allow more momentum. We should accept that cities will always be a little unfinished, a little unruly and far better for it.
So urbanism isn’t a luxury belief, but the idea that we can perfectly plan it all out before we commit to it, is. So I’ll leave that to Jasmine to wrap up up for she articulated it nicely …“We need to get out of the way so people can make things great. That actually makes everyone else’s job easier in the long run.”
To being Challengers.
