Why Did I Cycle Canada?

Curious as to why I left a cushy lawyer job to ride a bike and live in a tent? Me too.

Starting in June 2023, I began a bicycle trip from Tuktoyaktuk, in the Northwest Territories, to Victoria, British Columbia, and then on to St. John’s, Newfoundland and Labrador. My ride covered all three Canadian coasts: the Arctic Ocean, the Pacific Ocean, and the Atlantic Ocean. I crossed through ten Canadian provinces, two Canadian territories, twelve capital cities, and pedalled over 12,600 km.

You’re probably have questions about my trip, including: Why would I want to bicycle Canada? Why swap a great job and city lifestyle for unemployment and a tent? Why, if I wanted to travel, would I travel by bicycle?

I grew up on a bicycle, which let me access endless adventures from the moment I hopped on the saddle.

Bicycling has been a feature of my life since childhood. Some of my earliest memories are on two wheels, as are my greatest adventures. Biking has given me the opportunity to explore more of the world than I could by foot, and more intimately than I could by car or train.

In 2019, I completed my biggest ride from the Texas-Mexico border to Regina, Canada. I travelled via the Rocky Mountains and covered more than 4,200 km in three weeks. I loved all of it: the people I encountered, the landscapes my eyes couldn’t believe, the sense of accomplishment I felt at the end.

I put biking on pause while I focused on my legal career. This trip was my chance to return to that passion.

I graduated from university in 2018 with a law degree and practiced law in Toronto, Canada, and London, England.

My career proved enjoyable and fruitful. I worked on cases that changed lives and made the front pages of the business papers.

Work has never been dull: it’s always provided me with a sense of thrill and accomplishment. But being a lawyer is a demanding job, and the days can be long. That made it hard to pursue some of my personal goals, which often got pushed off so that I could focus on building my career.

In 2023, the time felt right to change my focus. But what would change look like? I approached this question with typical lawyer caution, thinking through the pros and cons and potential outcomes. My rational self told me to play it safe. But my gut kept telling me that the time was ripe for an adventure.

Adventure meant biking.

I have long held the dream of bicycling the world. For years, I pushed this dream aside on the basis that it was impractical and impossible. But this time felt different. The more I considered it, the more I thought: Why not?.

Of course, there are many answers as to “why not?” bike the world. But maybe, I thought, I could still find adventure on a bicycle if I narrowed the scope of my ride. Instead of a global circumnavigation, why not cross my home country, Canada?

Narrowing the scope of my ride to Canada felt right. It would let me bike a long distance, seek out adventure in new places, and get to better know my home country. This ride felt achievable while still maintaining a high degree of challenge.

Stepping aside from a budding law career to pursue a cross-country adventure on two wheels might seem foolish to some people. I can understand that perspective. It took me a while to decide on this trip. In the end, I grew comfortable with the idea that sometimes dreams can’t be rationalized or easily explained.

This trip felt right. And in the end, it was worth it.