As I wore it more often, its meaning changed. Nobody who really knew me respected me more (or less) because I wore the ring. It felt too obnoxious for business meetings. An acquaintance once told my girlfriend that there was no way it was real. I kept the certificate of authenticity, I didn’t think I’d actually need it though!

When someone drives a fast, loud sports car, they feel proud because they’re the center of attention. They feel respected and important. They don’t realize that many of us know that they paid a lot of money to buy this thing to impress us, and that may be a reflection of their own insecurity. Was it possible for them to feel important without the sports car? I wondered if my big gold ring said the same thing about me.

I stopped wearing it for a variety of reasons, but mostly because I decided that I didn’t want to impress everyone anymore. I’d only wear it if I really wanted to wear it, if the occasion felt right, and if it matched the rest of what I was wearing.

Most importantly, I got a better sense of what I valued and what I didn’t care about. I didn’t want to play those kinds of games. No more big rings.

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It’s wonderful to see these festivities in North America. When I grew up, lunar new year was barely even mentioned; it was just another day at school for me, and at the office for my parents. As a teenager, a handful of classmates would stay home to celebrate. I was told that the lunar new year was a huge deal in Asia.

A few years ago, when I lived in Hong Kong, the city bustled with people shuttling to and from family events. People want to preserve the fortune that comes with the new year. For example, nobody gets haircuts on new year’s day, so barbershops are closed. Similarly, people clean their houses the night before so they don’t sweep their good fortune away.

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And yet, people ask for directions. Even with the maps, the signs, and other wayfinding designs, people still ask. And they do so for all sorts of reasons:

Because they are in a rush.

Because they don’t want to get the wrong answer.

Because the digital map isn’t working properly.

Because they don’t have a device, connection, or app. Or they don’t want to use it. Or they’re out of battery.

Because they feel disoriented.

Because they want someone, even a stranger, to give them instructions.

Because they want a guide, or a companion.

Because they want an excuse to start a conversation.

Because it’s snowing and they can barely make out anything.

Because they’re in a new part of town.

Because.

Imagine when the context is less clear; where someone doesn’t know what they want, (literally or metaphorically) where they even are, and can’t speak the language. Imagine scenarios where they desperately need expertise.

No matter how old or advanced technology gets, people need people, for all sorts of reasons.

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If you want to save money on travel, your best bet is to be flexible either with where you want to go, or when you want to go. Preferably both.

A couple wants to celebrate Valentine’s Day, without paying exorbitant Valentine’s prices. Instead of getting dinner on February 14, they set a date for February 13.

Whether you want to stretch your dollar or avoid crowds, being flexible with timing can work to your advantage.

Because it’s unusual, it also creates tension, which in turn creates an occasion for an interesting story.

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That’s less the case now. There are several restaurants and stores open on Christmas Day, and what’s really nice is they offer a third space—not home, or the office—for people to get together. 

Whether they are students, expats, travellers, or locals who just want to get out of the house, there is a comfortable place for a person to get a cup of hot cocoa and be around other people, if they want.

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Techvibes was acquired in 2016, and most of the articles were stripped of author credentials. Some of them have all but disappeared from the internet.

Only one article has my name left on it, an interview with Carl Bass when he was leading Autodesk. 

Another post, which has all but disappeared from the internet, was one I’d written near the summer’s end of 2012, which my mind went to when I recently wrote about Cumberland Terrace.

I’m sharing these as both a reminder to myself of how much I’ve improved in a little over a decade, and also to give a very realistic sense of what early work looks like. It’s also a reminder that early work is supposed to feel embarrassing. 

I feel grateful for Rob and Knowlton, who led Techvibes at the time. The opportunity helped me change my life. 

P.S., Rob advised me to travel while I was young. It was good advice, and I ran with it.

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The most northern point of the Path is the Atrium on Bay. Several blocks north of this, there’s actually another set of underground tunnels that connects the Bloor-Yonge subway station with the Holt Renfrew Centre in Yorkville. 

In between these two sits the Cumberland Terrace, a shopping mall that made its debut a few decades ago. I spent a bit of time there, mostly over a decade ago when I did an internship in one of the office buildings. I remember while the mall felt outdated, the entrepreneurs and customers made the place feel vibrant, and there were a lot of people moving around. 

I recently learned that Cumberland Terrace was slated for demolition, and that there’d be new condos coming up. There’s a good opportunity for a new, better, underground shopping mall to come up. Still, I can’t help but consider that if the place was renovated properly, maybe it would’ve maintained its momentum.

If the new mall can get enough people interested, with enough time and resources, maybe the Path can extend to this set of tunnels (as well as the Shops at Aura, underground at Yonge and College, which sounds like it could use the connection).

P.S., Samuel Hughes did a fun write up of it for Works in Progress. I would be curious to learn more about what it would take for the Path to expand.

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My wife and I moved away from NYC, where we lived for two years, back to Toronto. I left my job as the director of marketing for FGX.

I spent a lot of time in the suburbs where I grew up, and that felt equal parts nostalgic and overwhelming. It felt like memories constantly streamed into my mind, whether they were welcome or not. I walked down sidewalks I hadn’t walked down in, probably, two decades. The suburbs are a place for people to survive. There is a wide range of people who live here. I see more babies and seniors here than I did in Manhattan. 

During this time, I regained a clearer sense of the child I used to be. I know a friend of a friend who works at the civic center, the building right beside my old high school. It’s not impossible to imagine a possibility that I never left the suburbs, and stayed in that area, eating at the same restaurants in the same plaza I grew up in. I’d be a very different person.

When I live in the suburbs, I feel more compelled to focus on defense. I feel inclined to spend less, instead of focusing on earning more or creating larger opportunities. This can feel draining and pessimistic. I realize why I felt so frustrated when I lived here in my younger, more proactive, years; I wanted to focus on offense, and my context set me up to focus on defense. Now, I’m more mature, and I can see the value of focusing on the foundation, and also set myself up for different modes. It seems to me like a lot of people live frugally. A couple of entrepreneurs I met in NYC started living in the city, then moved upstate or to Connecticut. 

Libraries offer free meeting rooms. We effectively started up our project in these spaces. It’s hard to believe, because time in a space like those rooms would have easily cost a couple of hundred bucks in Manhattan. 

We got to spend a bunch of time with family, both in Toronto and Hong Kong. We also visited Japan. I visited Kyoto for the first time, and I loved it. As we returned back to Toronto, the jet lag hit particularly hard.

My wife and I kicked off a project that will be marketing ready in a month or so, and production ready a few weeks after that. The work continues. Our little project quickly opened up a sense of possibility. We learned to lean into our respective strengths, and blend them to come up with something new. It’s plausible that it will evolve into a feasible business. I’m excited to ship to see what reality has to say about the vision. Either way, I feel really proud of what we have made. 

After a whirlwind of moves, we finally found a place to live downtown Toronto. It feels relieving and orienting.

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You compete with them by coming together with your team (which could be official teammates like co-workers, or unofficial teammates like friends and acquaintances). 

You share ideas and synthesize new ones together. You learn to rely on one another. You apologize when you make mistakes. You make adjustments to your approach when it doesn’t work.

This was inspired by the film, La Grand Maison Paris, which was very difficult to find with English subtitles. It was an energizing movie, and I didn’t want to share too many spoilers. My wife and I managed to find it on a Cathay Pacific flight, and we were delighted. We watched it twice.

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Try a new coffee shop, restaurant, or bar. Visit a nearby local town. Don’t order your favorite dish, set out to find a second favorite.

Don’t be surprised to find yourself getting luckier.

P.S., There is a time and place to commit, and to maintain what’s working well. This is not a call to interrupt either.

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