Seven Years After We Said Goodbye to Our Careers

What seven years of freedom have taught us about life, travel, and money

Seven years ago this month, we were closing out our apartment in Singapore, selling off almost everything we owned. Every day, more furniture and household goods disappeared to a parade of buyers, leaving us eating meals camped on the living-room floor because we’d sold the dining chairs along with the sofa, the coffee table, and anything else we could put a price tag on.

This was the final stage in the intense run up to leaving our jobs and beginning a new life as financially independent, early retired globetrotters. We were, in fact, very early retired as I was 46 at the time and Gillian was just 38. We’d spent the previous couple years cutting costs, chasing our investment targets, and dreaming of travel. Now we were finally ready to give up the corporate jobs that were slowly but surely crushing our spirits. The plan: hop on a one-way flight to Europe with just two suitcases, two backpacks, and two poodles. We had an itinerary covering the six months or so and then we’d see what came next.

What followed was over four years of slow travel through 19 countries across Europe and the Americas. We couldn’t have picked a worse time, of course, as COVID exploded across the world just as we reached our fourth country. Still, we flew to whatever destination was open to us at the time and kept exploring.

Eventually we reached a saturation point. We had crammed so many peak, once-in-a-lifetime experiences into a relatively short period—seeing the sun rise over the Acropolis, hiking the rim of a crater in Ecuador, surfing in Puerto Escondido—and every week of travel added even more to the list. We were also, quite frankly, burnt out from all the travel planning. Dreaming of new destinations is a pleasure but booking flights and accommodations covering 12 months of the year is just plain exhausting.

This led to our current chapter of post-work life. We bought a house in a little village in Ontario and now spend the warmest, sunniest months of the year enjoying the quiet pleasures of small town living. During the winter, we’re slow traveling through new destinations with our two dogs. Spring and autumn are for the epic multi-day hiking trips that we love.

It’s been seven years since this journey began, which feels like a good time to take stock. Back in 2019, we headed off to Singapore’s Changi Airport feeling like life was full of possibilities now that we no longer had to work for a living. Seven years later, what have we learned about ourselves, travel, finances, and pursuing a life of freedom?

We don’t miss work one bit

As we set off to travel the world, we often wondered whether we would wake up one rainy morning in some European city surrounded by our luggage and feel like we’d made a terrible mistake in quitting our jobs. After all, we had both spent the majority of our adult lives in pursuit of building our careers. Along the way, Gillian had acquired one master’s degree and I had two, all in the name of professional development. While Gillian had been mulling over the idea of early retirement for many years, I always assumed that I would keep working far into the distant future

Contrary to our secret fears of regret, once we left work, we never looked back. We didn’t miss going to the office each day or sitting through lengthy meetings or spending Saturday mornings catching up on our emails. We no longer had to fine tune our LinkedIn profiles or worry about pitching ideas to higher ups. That part of our life was over and we were thrilled to be done with it.

There are a lot of hours in the day

While we didn’t miss work, we soon realized that the lack of a job meant that we had an extra eight hours a day to fill with meaningful activities. Make that 10 hours if we include the time we used to spend packing lunches, dressing up for work, and commuting to the office.

Of course, being travellers exploring new cities each month took up a large portion of our time. However, we quickly discovered that it wasn’t possible or even desirable to play tourist everyday. Full-time travel is most sustainable when treated as a marathon, not as a one-week vacation sprint. For us, that meant maybe one or two major excursions each week, leaving us with a lot of time to fill.

In between tourist attractions, we needed fairly substantial projects as creative outlets. While we were traveling full time, that project was churning out Youtube videos every week or two for years. Now that we have a home base, we have a variety of pastimes to keep us busy: we’re both volunteering for an international dog rescue, I’m fostering kittens, and Gillian is cultivating the vegetable garden she always wanted. And we have this monthly newsletter and the occasional video when we’re excited to share our latest adventures. These are all meaty projects that keep us feeling productive but on our own terms.

Even freedom needs some structure

There was a brief honeymoon period when we first gave up work and were suddenly able to spend our time however we wanted. We slept in, had lengthy brunches, enjoyed an afternoon tipple, and binged on TV shows. It was a long weekend feeling that never had to end—except that we are happiest when we face the day with goals and a plan.

After a few weeks of lazy mornings and equally lazy afternoons, we returned to the healthy habits that had seen us through our stressed-out working years. Most importantly, no matter where we are in the world, we start our day with fitness, whether it’s lifting weights, running, or yoga. Add to that two to three walks with our dogs each day, cooking most of our meals at home, time for reading and language learning, and it’s a recipe for what we feel is a fairly healthy lifestyle.

Relationships take work

One of the most significant outcomes from retiring early to travel the world is that we’re out of sync with our peers. Most of our friends or family members in the same age bracket are spending their time doubling down on work during their prime earning years. Travel is something that gets squeezed into one or two week vacations. Our life of freedom is almost totally unrelatable to the people who have known us the longest.

Of course, we’ve built a new community around us of fellow nomads and early retirees, thanks in large part to our Youtube channel. However, the reality of making friends with other travelers is that everyone is always on the move. We might enjoy a wonderful lunch together in Brasov, Romania and then never ever see each other again.

We’ve found that we need to put in an effort with all our important relationships, which is one of the reasons we wanted to have a home base back in Canada after living abroad for a decade. Video calls are great for staying in touch but there is ultimately no substitute for spending quality time in person. We’re now focused on creating more memorable occasions with the people we love, which is helping us catch up after so many years overseas.

The wanderlust never went away

Even though we have a home now, we still want to see the world. In fact, having a home makes travel even easier for us; we can leave our dogs with housesitters and explore destinations that would be difficult to visit with a menagerie in tow.

Since settling into our home base, we’ve trekked to Machu Picchu, hiked the Cotswold Way in England, adventured through the country of Georgia, and toured Shikoku, Japan. Our more adventurous trips are even more enjoyable knowing that we are returning to our own home with our own bed. And shifting from full-time travel to one-off, intentional trips has helped bring the magic back to our world explorations.

Our finances have faded into the background

There was a time when we listened to financial podcasts on the way to the office, read our favourite FIRE blogs through lunch, and spent evenings debating how we could cut even more costs from our spendy expat lifestyle in Singapore. Thankfully, those exhausting days are now over.

Yes, we still maintain a massive spreadsheet with our investments, expenses, and safe withdrawal rate scenarios all laid out. And, yes, we still track our spending down to the penny and hold quarterly financial summits to review our portfolio. But we can largely rest easy knowing that our financial strategy has been road tested over the past seven years and functions just as we hoped it would. We can attest that the financial independence premise—spend less than you make, invest the difference, buy your freedom—really does work.

Chasing big goals is important to us

We’ve spent most of this newsletter looking back at what the past seven years have taught us. But we’ve been working towards one major life-changing goal after another for much longer than that—about 15 years, in fact.

First, the move to Singapore, which was only possible because we spent long evenings plumbing the depths of LinkedIn to find companies willing to give us jobs. Next came a lengthy period focused on career progression while we built a life in Singapore. Then the discovery of the financial independence community and a lifestyle shift from extravagance to frugality. From there, world travel, and then finally settling back in our home country.

We don’t know what the next chapter will bring but we’re hoping that it will be just as challenging and interesting as what we’ve accomplished so far.

See you on the road,

Stephanie & Gillian

P.S. Just a few days ago, we returned from a milestone hike that we’ve been dreaming of for years. The Tour du Mont Blanc is a 10-day hike that travels up and down the mountain passes of France, Italy and Switzerland, and was most certainly our biggest challenge to date—not least because we had to spend one night in a cozy dorm with five strangers 😅. We’re sharing all the details (including a video!) in next month’s newsletter.