There is a school of thought that out-of-office messages are only for the unserious. If you're a top-performing executive, owner, or whatever, you need to be available and reachable at all times, and so an OOO message sends completely the wrong signal. It says that you're just not that committed to what you do. Yeah, I always use an OOO message when I'm away.

While I appreciate that school of thought and I know firsthand that when you have your own business you're on 24/7 (because of some unhealthy combination of drive and obsession), I also believe that the following two things are true.

One, we could all die tomorrow and it's important to take some time when you can. In fact, I'd say greater freedom is the objective. As Charlie Munger famously stated: "I did not intend to get rich. I wanted to get independent, I just overshot."

Two, as connected as we all are today, there's no way that when I'm crushing back bowls at high elevations I'm going to be able to respond as quickly as I do when I'm sitting at my desk for 15 hours a day. So I think it's important to let people know, "Hey, if I don't respond to you in 38 seconds, I have not died; you just need to wait a bit longer."

The signal is a recalibration of expectations, not of my level of commitment.

Cover photo by Luca Bravo

My sense is that density is a misunderstood characteristic of successful cities. I think most people see it as a bug. They see some of the negative externalities associated with cities, such as traffic congestion, and they assume that the culprit is too many people.

But they are confusing population density with land-use inefficiencies. This, I can only assume, is why some people arrive at the selfish conclusion that their city is full.

There are, of course, many counterexamples to this line of thinking. Paris, Seoul, Barcelona, Singapore, Tokyo, and many others have both high population density and are viewed as being highly livable and desirable cities.

Not all high-density cities are livable, but that's because other ingredients are missing. I will remind you that Tokyo once again placed first in Monocle's annual quality-of-life survey this year.

What I think gets missed are the following three key features of urban density.

One, dense cities dramatically lower the cost of delivering infrastructure over the long term and reduce per capita energy consumption.

Two, cities are wealth-generating machines and density drives "agglomeration economies." Put smart and entrepreneurial people in close proximity to one another, and good things happen.

Three, the only way to create an enormous, well-functioning city like Tokyo is on the backbone of transit. And the only way to make transit viable and convenient for most people is to build density all around it. Density is the unlock that makes it all possible.

Ironically, then, density is what can make cities feel less congested and more livable.

Cover photo by Agathe

So, what bold and uncomfortable 21st-century master plan should Toronto adopt? I don't know exactly, but what I was getting at in my lead-up post is that it's hard not to sometimes feel like Toronto is trying to run a 21st-century global city on a 19th-century Victorian street grid, surrounded by Houston.

In the core of the city, we have narrow, generally 20-metre rights-of-way. Many of these east-west arteries are beautiful streets to walk on with fine-grained retail patterns, but the streets themselves have slow-moving streetcars in the middle two lanes and on-street parking on both sides. The result is streets that don't move and are frustrating to navigate for all users: drivers, transit riders, and cyclists. It can take an hour to drive 10 km.

Other major streets don't have streetcars or much retail activity, but the land-use pattern reflects a bygone era. It doesn't make sense to have only single-family housing on Toronto's busiest arteries. It's time for these streets to grow up. (To be fair, the City of Toronto is trying to achieve this with its new Major Streets policies, but the development economics do not make these changes feasible at scale.)

As you move out of the core, Toronto's major streets naturally widen along with the recency in which they were built. Now we have the opposite problem where we're faced with "stroads" with little to no urbanity. Overall, it's the result of a city that grew organically over time without the same kind of defined plan seen in cities like New York, Barcelona, and Paris (after it had already been built out).

Here's the thing: Toronto's low-rise single-family era is over. Virtually the only single-family housing that gets built nowadays is when somebody demolishes an existing house and builds anew. The future is a uniformly higher-density city built on the backbone of robust transit, vehicular, and cycling networks; not a monocentric downtown that people commute to.

So what might that mean exactly?

To start, I believe it means getting our transit vehicles onto their own dedicated lanes, widening certain major streets (for the benefit of cars), shrinking and pedestrianizing others (for the benefit of human-scaled urbanism), carving through new major streets to fix connectivity gaps, and pricing congestion as a means of funding constant transit expansion. My fellow urbanists may not want to hear me advocate for the selective widening and creation of arterial roads, but we have to stop pretending that cars are going to disappear.

Once the bones are in place, it's then a matter of getting the land-use policies right and letting the private sector do what it does best — build for the future. Now, I don't profess to know the exact combination of major street widths, one-way patterns, and whatever else should be done, but I do feel strongly that it's time for a bold and uncomfortable 21st-century master plan for Toronto.

What does Toronto want to be? We should host an international design competition and find out.

Cover photo by Oles Borys