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Running in Portugal

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I finished my trip with 4 nights in Lisbon. It was the middle of the week so my days resembled something like a regular routine. 

Each day, I’d meet up with my friend Carlin, and together we’d settle into what I think is one of Europe’s most remote-friendly cities. In the day, we’d work and eat in local cafes. In the evening, we’d wander around for the best food, bars, and companions, often with good luck.

A talented singer in the nightlife district.

In between, I ran.

Lisbon is a remarkably hilly and wet city – not my favourite running conditions. But by this leg of the trip, since I hadn’t been able to easily access a gym or court, my general inclination towards running turned into a full-blown habit. So I ran.

Why had I come to enjoy running so much?

It helps that my body naturally excels at it. So does the fact that it helps keep me in shape. But I think running began to resonate with me on a deeper level on this trip because it aligns with how I think about travelling.

One of my favourite things about running is discovery. Whether I’m running through Seville or South Granville, I love that running gives me an excuse to pick a new place to experience and set out for it. I like to chart my runs around points of interest. 

In North Vancouver, for example, I’d often run to the river behind my house, and in Lisbon, that started with the Praca do Comercio and extended to many other city landmarks.

This is, of course, one of the best parts about travelling as well: charting out adventures to great sights. In Lisbon, the highlight was a trip to Sintra. I had never heard of it, but Carlin insisted that I find a way to get there, and I wasn’t disappointed. 

It was similar in many ways to my trip to Ronda from Seville: absurdly good food, interesting architecture, nice people, natural beauty. But just as the Spanish and Portuguese are similar-yet-distinct, this excursion too had its own flavour. Spain’s sombre, grandiose statements of Catholicism were exchanged for more baroque, unrestrained expressions of early capitalism and Freemasonry (see: Initiation Well below).

Of course, anyone will tell you that travelling is not just about the destination. I enjoy running too because although it can be goal-oriented, it forces you to pay attention to the journey.

For one, if you focus your running on trying to get somewhere as soon as possible in a straight line, it’s a pretty boring activity. Running is only enjoyable when you savour the process itself. That can mean paying attention to your technique, but it can also just mean finding enjoyment in the time spent with yourself. I enjoy my time running the most when I either have something in my life I want to reflect on, have a podcast I want to listen to, or want to listen to music for the sake of music. Running frees my brain to do that.

Running is also improvisational in nature. I have the option to randomly change my path, follow my instinct, or adjust my pace. Some of my favourite moments running are when I stumble upon a random park, alley or oddity that I had no idea existed. 

Recently while running in Vancouver, I stumbled into Almond Park, which I commuted by every day for years but never noticed. In Lisbon, one of my highlights was running through their graffiti-drenched staircases and switchbacks, trying (and failing) to reorient myself. Some of my favourite moments in Sintra included our random stop-offs outside the main castle.

My friend Drew is always trying to convince me to take up cycling, and that’s one of the reasons I never will. I don’t want to give up even a little bit of that improvisational freedom.

Last, for me, both running and travelling are escapes. Although I think this is healthier than the word connotes. 

I consider myself to be blessed with a career I’m obsessed with. But business never stops, and at times, I have a hard time stopping thinking about it. I typically only stop when I have a forcing function.

Travel acts as a macro forcing function, forcing me to set aside not just work but many of the other activities than end up filling my day. This makes for lots of time for grounding activities.

In my day-to-day life, running is one of my few micro forcing functions. It allows me to create space that’s completely my own. As I’ve settled back into life this year, that space has helped me process both my Toronto move-and-back and the news of Lily getting cancer.


Since leaving Portugal, my ability to travel has been restricted by COVID-19 and cancer. Ironically, since my movement is restricted, I have more time for my other escape, running. This has been really crucial to my wellbeing in a difficult time. In a way, my time running while travelling was the perfect preparation for being able to cultivate a sense of discovery and enjoy the journey at home.

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