This evening I attended the 27th Annual Toronto Planning Dinner. It’s an annual dinner for people in planning and development, put on by the University of Waterloo Planning Alumni of Toronto. Thank you Wood Bull LLP for the invite.

The keynote speaker was Dr. Anthony Townsend. He is the author of SMART CITIES: Big Data, Civic Hackers, and the Quest for a New Utopia. I haven’t read it (yet), but his talk offered a preview of it and I think it would be of interest to all of you.

It deals with many of the topics that we discuss on this blog, one of which is the interrelationship between our physical environment and the networks and software layers that we are now building on top of it.

These layers have the potential to augment and enhance our cities (maybe make them smarter), but they also have the potential to do us harm. One important issue that Townsend brought up is that of privacy.

Cities used to enable anonymity. 

When essayist and art critic Charles Baudelaire wrote about “modernity” in 19th century industrializing Paris, it referred to an ephemeral and fleeting kind of urban environment. Pass someone on the street and you may never see them again. That must have felt sad at the time.

Today we live in a fish bowl. 

Networks connect us, check us in, ping us when we are nearby people we know, and help us find people to meet and date. And we already have devices, like Alexa, that spy on us in our homes so that companies can serve us targeted ads. (This is deplorable by the way.)

Will the city of the future endeavour to do the same as we equip it with more “smarts”?

I guess that’s why Townsend believes that privacy will define a big part of 21st century urbanism. There’s no doubt that it will be very important.

Yesterday it was announced (here, here, and here) that Toronto-based Top Hat has raised $22.5 million (USD) in Series-C funding. The round was led by New York-based Union Square Ventures.

I am always excited to see Toronto-based startups doing well and I am particularly excited by this remark in USV’s blog announcement:

“Also worth noting is that Toronto continues to impress us with its quality and diversity of companies. We now have five investments there, placing Toronto third as a location in the USV portfolio after New York and San Francisco.”

Here is another quote from Fred Wilson’s blog:

“Toronto is a great place for startups. In addition to five investments of ours that are HQ’d there, I know of at least one other USV portfolio company that has much of their engineering team in Toronto. The talent, mindset, and quality of the people in the Toronto/Waterloo tech/startup community is really top notch and we love investing there.”

Go Toronto. 

(Of course, Toronto really means Toronto-Waterloo. That’s the geography of the ecosystem.)

When I was 18 years old, I moved from the suburbs of Toronto to Waterloo, Ontario, which is about an hour west of the city.

I largely did this for two reasons.

Firstly, I had started visiting friends at both Wilfrid Laurier University and the University of Waterloo while I was in high school, and I thought that I wanted that kind of University town experience.

Secondly, I started University as a Computer Science student and I figured that Waterloo was a pretty good place to study that. Research In Motion (later renamed to Blackberry) was an important company at the time and interesting things were happening.

Though to be clear, I was a student at Laurier and not at the University of Waterloo – the better of the two schools for Computer Science – because I didn’t have the grades for the latter.

But a funny thing ended up happening. I hated living in Waterloo. I felt so out of place. So much so that I spent every weekend back in Toronto visiting my friends who had instead decided to go to the University of Toronto.

And I remember vividly how I felt during those weekends. I would stand in my friend’s apartments – most of which had dens and solariums that were hacked into bedrooms so that they could afford to live there – and I would look across the skyline and think to myself: why the hell do I not live here?

So I transferred to the University of Toronto. And that solved that.

The reason I bring up this story today is that I was reminded of it while reading a recent CityLab article by Richard Florida called, The Self-Confident City.

The three main arguments in the article are:

(1) Where we choose to live has a massive impact on our life outcomes.

(2) Self-confident people – according to a recent study – seem to be drawn to big cities.

(3) Self-confidence can also be a self-fulfilling prophecy for people in big cities.

Now, I don’t know if it was really self-confidence and youthful hubris that told me I needed to live in a bigger city than Waterloo. (It was probably part of it.) All I know is that I wanted to live in a super dynamic place that felt bigger than me. I wanted to feel like I was a small fish in a big pond trying to make some sort of meaningful dent.

That was true for me when I was 18. And it remains true for me today at 32.