There’s a certain mediocrity pervasive in Canada. It invades our governments and their policies, stifles our innovation, and makes our cultural presence weak at best. This mediocrity was a key cause of the failure of Sidewalk Labs in Toronto.
Sidewalk Labs (SWL) was a subsidiary of Google, who won a bid to develop a coveted and underdeveloped part of Toronto’s waterfront — a site called Quayside. Toronto’s eastern waterfront has suffered greatly in the years after industry evacuated the city. The shell of factories and refineries has left a hole in Toronto’s core that is still unfilled properly to this day. This presented an obvious opportunity to Toronto’s stakeholders to provide a model for how we could use underutilised land.
This is fundamentally a story about the tech industry trying to do non-tech things. Sidewalk wanted to propose a new paradigm for how cities are planned and built. They proposed a techno futuristic smart city full of sensors and big data and always-running algorithms. Their manifesto, a Yellow Book, was comically dystopian. It’s like they never thought about non-tech perspectives. Who really wants mass data collection or lives dictated by an algorithm? Part of the big problem of the digital world is that things are dictated by things out of our control — network outages, data loss (in the storage sense), and data breaches (in the security sense) — and there’s often not much we can do about it.
Tech is hyper-individualistic, so its solutions are too. Sidewalk proposed pod housing and self-driving cars. They assumed a fast deadline, because timelines in big tech move incredibly fast. But the reality is that timelines in the real world run comparably slower. Objectively, this mismatch results in the inevitable downfall of SWL. Their ideas could’ve worked in practice, but we’ll never know because they would’ve had to put up with years and possibly decades of slow change.
In fact, I’d argue that for a city of the future to come into form, we have to be brave enough to try one out, to prototype the ideas, and to stress and strain them. Indeed, the future won’t come into fruition if we don’t try things out or if we rule things out before they even get off the ground.
Of course, things don’t have to be slow. The government is inefficient sometimes, and there are often lots of assessments for no reason. There’s lots of institutional inertia that prevents good projects and good change. But the overarching rationale behind these checks is that decisions that impact people should be thoughtful and executed not by incompetent actors.
And that’s not to say that the private sector (and big tech) holds a monopoly on incompetence. The Sidewalk Toronto saga has revealed the staggering incompetence of Toronto’s municipal government and of Canada’s federal government during the 2010s.
Let’s start with Toronto itself. Sideways diagnoses correctly why Sidewalk came to Toronto in the first place. Chapter 5 defines two of “Toronto’s defining, competing attributes — ambition and insecurity”. For the first, we desire the prestige and wealth that comes with big tech investment and being a cultural powerhouse of the world, but without diagnosing what makes cities like New York or London or Chicago so attractive. For the latter, we compare ourselves with these global cities on grounds that no reasonable person can agree to, or to cities we are decidedly not in the same tier with. A pervasive cultural mediocrity. Waterfront Toronto decided to choose a CEO from Colorado Springs during this vital time. Because we emulate America so often, we import their worst aspects.
“Sidewalk Labs’ original sin” is arguably solely on the part of Waterfront Toronto, the multi-government organisation that ran the show. They couldn’t bother giving enough detail about what they wanted. In fact, I’d argue this objectively proves it’s not ultimately fully on Google that Sidewalk Toronto failed. For every failure on SWL’s parts, political mediocrity and bureaucracy has made another misstep.
Sideways also correctly predicts the direction the data collection was going (so well that the book will have aged well in 5-10 years) — already in the 2010s, big data and algorithmic frameworks were controlling an unprecedented amount of the Internet. It’s notable, in this respect, that Canada is still not ready for the Internet age. While Europe and California have adopted reasonable data privacy measures, Canada’s baseline is PIPEDA, originally adopted in 2000 in a much different world. It’s telling that the federal government could not even step up to such a basic challenge. This could’ve been an easy win, but our overwhelming political mediocrity has forced everyday Canadians to be surveilled on with no protections of our own.
I will end on this note. It is truly infuriating to see incompetence at a scale like this. Not only in Waterfront Toronto (who were incapable of clear communication), and in Google (who couldn’t figure out a cohesive vision for what they wanted), and in the federal government (who flip-flopped on regulation so much that SWL would’ve been unviable even if everything else went as planned). Quayside could’ve been much more than what we got — but we will never know.
4.5/5
Written 7 September 2025
Adapted from my review on Goodreads.
Notes
- a story about the tech industry trying to do non-tech things
- timelines in tech move fast, but timelines in the real world comparably slower
- objectively you can think of this mismatch as being the inevitable downfall of SWL. their ideas could work in practice but we’ll never know because they would’ve had to put up with years and possibly decades of slow change
- don’t have to be slow — govt is inefficient sometimes, lots of assessments for no reason. lots of institutional inertia that prevents good projects and good change
- tech is hyper individualistic, so its solutions are too (pods, self driving cars)
- i’d argue that for a city of the future to come into form, we must try one out, prototype the ideas, and stress and strain them. indeed, the future in general won’t come into fruition if we don’t try things out or if we rule things out before they even get off the ground
- sidewalk labs’ yellow book is comically dystopian. it’s like they don’t even think about non-tech perspectives. who would want mass data collection or lives dictated by an algorithm? part of the problem of the digital world is that things are dictated by things outside of our control — network outages, data loss, etc. and there’s not much we can do about it
- chapter 5 or so is really good at diagnosing why sidewalk labs came to toronto in the first place
- it’s an indictment of toronto mediocrity — two defining traits — insecurity and something else idk
- stealing other cities’ slogans
- terrible urban design — single family homes as far as the eye can see
- cultural mediocrity that defines everything — this is why we’re not as good as cities like Chicago or Montréal or NYC or Seattle
- chose some dude from bumfuck middle of nowhere (Boulder Springs, Colorado). because we emulate the US in so many aspects, we import their worst aspects
- this is still grating to me. lots of American cities do things wrong, but it’s the middling cities of middle America that we shouldn’t be emulating
- “SWL’s original sin” — because Waterfront Toronto couldn’t possibly even give enough detail about what they wanted
- i feel like this objectively proves it’s ultimately not fully on GOOG that SWL failed. it’s literal political mediocrity and bureaucracy that failed things too
- it’s an indictment of toronto mediocrity — two defining traits — insecurity and something else idk
- writing is okay right now
- a little boring, but i think sets the scene well so far. might be better because it’s an audiobook, so the tedium is lost a little
- hits on a good point re: AI and the direction data collection was heading
- inherent mediocrity of Canadian governments
- copying half baked regulations from other countries
- PIPEDA and data privacy (still not a solved problem)