Why Am I Cycling 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’ll be riding my bicycle from Tuktoyaktuk, in the Northwest Territories, to Victoria, British Columbia, and on to St. John’s, Newfoundland and Labrador. My ride will cover all three Canadian coasts: the Arctic Ocean, the Pacific Ocean, and the Atlantic Ocean. I’ll cross through ten Canadian provinces, two Canadian territories, twelve capital cities, and nearly 15,000km.

And if I still have energy once I reach the Atlantic Ocean, might I push south to Ushuaia, Argentina, and complete a cycle tour of the Americas?

You’re probably have questions, 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. Now, I want to return to that passion.

I graduated from university in 2018 with a law degree, and then worked at a top corporate law firm in Toronto, Canada. As I became more comfortable in my job, I craved new challenges. So in 2021, I packed my bags and took up a new job at a large law firm in London, England.

I’ve now been a lawyer for about five years. Throughout my career, I’ve worked on cases that have 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.

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: surely, I could balance my career and personal goals by tweaking the scope of my existing job, or perhaps by finding a new job.

But my gut kept telling me that the time was ripe for an adventure – and adventure meant biking.

I have long held the dream of bicycling the world. For years, I pushed this dream aside, thinking it impractical and impossible. But this time felt different. The more I considered it, the more I thought “Why not?”.

Of course, there are many reasons why one shouldn’t (or can’t) bicycle the world, including the hard-to-avoid fact that many of the countries I would need to cross are dealing with political instabilities and/or at war. But maybe, I thought, I could still obtain a bicycle adventure if I narrowed the scope of my ride. Instead of a global circumnavigation, why not cross my home country, Canada? Why not cross my home continent, North America? And if I’m already going that far, why not push to the end of the road at the southern tip of the Americas?

I decided to narrow the scope of my ride to one country: Canada. That change felt right. A Canadian route 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 – even stupid – to some people. I can understand their perspective. My rational self is still trying to rationalise this trip. Sometimes, however, dreams can’t be rationalised or easily explained.

This trip feels right. It represents a shift in my focus to a purely personal goal. It’s a re-set from my recent past.

My career as a lawyer is far from over, but it will be going on pause. I wanted change, and what better way to find change than over the course of some 15,000 km?