And why urban messiness is an important feature of cities
February 4, 2026 · View original
I’m back in Toronto. And another “fresh pow annual” is in the books.
The BC interior is a specific kind of ski and snowboard trip. It’s not about dancing on tables in neon onesies while Champagne gondolas fly overhead. It’s about chasing champagne powder with like-minded middle-aged men, all pretending that they don’t otherwise live a sedentary, low-range-of-motion lifestyle for the balance of the year.
Both have their merits.
We stayed in four different accommodations for this trip, and one of the things that became very apparent is that everyone is trying to over-optimize around “good service.” In each case, I was getting text messages and emails before the stay, during the stay, and after the stay.
“Here’s how to prepare before check-in.” “Is there anything we can do to make your stay more enjoyable?” “How was your stay?” “Please share your experience with us here.” In one case, I even received a phone call from the front desk as soon as I got to my room: “We just wanted to see if everything in your room is to your liking.”
On the one hand, this level of communication and responsiveness is fantastic when you do need something. But on the other hand, it can be overwhelming. Blasting everyone with automated text messages and emails does not, in my opinion, stand out as exceptional hospitality, especially since everyone now seems to be doing it.
Outstanding hospitality is emotional, rather than technical.
In city-building news, Bloomberg recently published an article about why cities should embrace “messiness.” In it, they cite a book that was assembled by some fellow Torontonians:
> This premise — that urban planning’s efforts to impose order risk editing out the culture, character, complexity and creative friction that makes cities cities — is a guiding theme in Messy Cities: Why We Can’t Plan Everything, a collection of essays, including Thorne’s, gathered by Toronto-based editors Zahra Ebrahim, Leslie Woo, Dylan Reid and John Lorinc. In it, they argue that “messiness is an essential element of the city.” Case studies from around the world show how imperfection can be embraced, created and preserved, from the informal street eateries of East Los Angeles to the sports facilities carved out of derelict spaces in Mumbai.
Messiness and allowing for ground-up urban interventions are themes that I have written a lot about on this blog over the years. I think we have gone overboard with rules and regulations, to the point that we stamp out many of the things that make cities so wonderful.
Top-down planning will never get everything right. It’s impossible. And the big thing about over-planning is that, in the end, we don’t actually know what we’re missing out on. We don’t know what might have been possible if only we had allowed for it or were more flexible in our approaches.
Messiness is a feature of cities, not a bug. We should be embracing it.
