How to Avoid a Boomerang U.S.-to-Canada Move


Have you ever considered a U.S.-to-Canada move?

That’s exactly what Mina and Trevor (not their real names) did when they quit their soul-crushing 9-5 jobs, downsized, sold their condo, and moved from Los Angeles, California to Toronto, Ontario in 2017. Over the next few months, however, the couple had a series of epiphanies that led them to abandon their plans to live in Canada and move back to L.A.

In this post, you’ll learn about 9 unexpected discoveries that prompted their boomerang U.S.-to-Canada move. You’ll also find out 3 ways Your Place Finder could have helped them – and can help you – avoid a costly and stressful moving mistake!

Great expectations

Mina and Trevor envisioned a better life for themselves in Toronto.

A Canadian citizen who had lived in the U.S. for 18 years, Trevor’s memories of growing up in Canada promised the more minimalist lifestyle and less consumer-oriented culture that they sought. They figured Trevor could get a job in Toronto that would provide enough health insurance and income, so that Mina could start and grow her own online business.

Family also played a role in their decision. The couple was hoping the move would help to strengthen relationships with his parents. By moving to Toronto, they would be closer to Trevor’s parents in the suburbs.

Toronto seemed to check off all their boxes as well. From previous visits they know they liked its cosmopolitan feel – with lots of great food, entertainment and a thriving local artisan community. And, based on their online research, Toronto had many of the qualities they were looking for: four seasons, lots of events and parks, wine and coffee tasting, good public transportation, an active live music community, and a bohemian culture.

Stark realities

And so, the couple packed up everything and moved with their cat to Canada in September 2017. For the first four months, the couple lived with Trevor’s parents. In January, they moved into a 600 square-foot apartment in Toronto within walking distance of Trevor’s new workplace. Over the next few months, the couple made a series of surprising discoveries which ultimately led them to leave Canada and move back to L.A.

What did they learn from their boomerang U.S.-to-Canada move? Let’s have a look.


After moving to Canada, Mina, a U.S. citizen, and Trevor, a Canadian citizen, learned that in order for Trevor to keep his U.S. legal residency, he’d have to return to the U.S. every six months. Both were worried his U.S. Green Card would be revoked and he’d have to start the process all over again. On top of that was the unacceptable possibility they might have to live apart. As a married couple they thought it would be easier for Mina to apply for residency in Ontario than it was for Trevor to apply in the U.S.

Once the couple decided to head back to the U.S, Mina stopped her application to become a Canadian permanent resident after learning it was just as difficult to apply in Canada as it was for Trevor to apply for residency in the U.S. To maintain Mina’s U.S. citizenship and Trevor’s legal residency status, they would have to continue to pay state taxes for three more years and federal taxes for as long as Mina wanted to maintain U.S. citizenship.

Health insurance

Health insurance was another major deal-breaker. Mina and Trevor found out they had to live in Ontario for three months to qualify for health insurance there. They also learned that Canada’s government health insurance provided for basic medical care only. This meant they would need to get supplemental vision and dental care insurance through Trevor’s employer. Except that, contrary to what they had originally thought, Mina was not eligible for health insurance as the wife of a Canadian citizen. To qualify for healthcare coverage, she would have to work full-time for a Canadian company and commit to six months employment. This put an end to her dream of starting her own online business.

Health care availability

The couple also didn’t expect health care availability to be such an issue. The reality was it could take months to get a medical appointment. When they did get an appointment, it might be in the middle of the night in a hospital setting instead of at a local medical center like in the California. A 2019 Frasier Institute study found overall waiting times for medically necessary treatment ranged from four months in Ontario to nearly a year in Prince Edward Island.

Housing costs

Mina and Trevor quickly learned how impractical it was to live in a 600 square-foot apartment – even for two minimalists and one cat. But, in Toronto, a tiny apartment was all they could afford on a well-paid professional’s salary. (Although they got an underground parking spot – not a common perk in downtown Toronto!) Buying a house was out of the question. Even housing and other costs of living outside Toronto were considerably higher than they had anticipated. They were shocked when they realized the cost of housing in Ontario proved to be just as high, if not higher, than in southern California.

Mina and Trevor liked the city of Hamilton, located a few hours outside of Toronto, but could only afford to buy a fixer-upper house there. After factoring in costs to renovate a fixer upper in Ontario, which are much higher than L.A. due to the extreme cold weather, the couple realized they were priced out of that market and that they would rather live near the beach for the same price.


After living for the past 18 years in Los Angeles, Mina and Trevor wanted to live someplace with four seasons. They liked that it was sunny most days in Toronto. But they didn’t like that the temperatures stayed below freezing for six months, and that the cold was SO COLD. After being outside every day in California, they didn’t like having to spend so many months indoors. It was only after living in Toronto that they realized they preferred to live someplace where the weather is warmer year-round. A place like southern California.

Cultural compatibility

Another post-move revelation for Mina and Trevor was just how well-suited they really were to the California culture and lifestyle. When they’d left L.A. for Toronto, one of their goals had been to experience a different culture. The couple had hoped Canada would be less capitalistic. They learned after their move, however, that capitalism is worse in some ways there than in the U.S. as there are more monopolies.

Mina and Trevor also realized that the things they were really “into” culturally – tiki bars, vegan restaurants, Trader Joe’s, mariachi music, and Mexican festivals like Day of the Dead – were California things. On top of that was the discovery that they weren’t as interested in being active in the music community as they had been in the past.


Toronto’s excellent commuter rail was one reason Mina and Trevor chose to move there. However, because not enough trains ran during the winter, a lot of people were left stranded out in the cold. And driving was not a desirable option since traffic congestion was bad and drivers were aggressive. Plus, icy roads and snowstorms were a major concern.

Food availability

Mina and Trevor were surprised to discover that food availability was an issue in Toronto. In California, they’d had access to fresh fruit and vegetables year-round. After learning this was not the case in Canada, they realized just how much living in California had spoiled them for anywhere else.

Social compatibility

The lack of social connection that Mina and Trevor felt in Toronto was the final straw. Although they had visited before, it was only after living in Toronto that they realized how incompatible they were with the isolated lifestyle of Canada’s winter weather. Without friends or acquaintances – not even their neighbors – their isolation further stoked their plans to move back to L.A. in May 2018.

Silver linings

Ultimately, Mina and Trevor’s boomerang U.S.-to-Canada move revealed a silver lining. The move renewed their appreciation for the California lifestyle. It also deepened the relationships they had with their parents. Fast forward two years – the couple is happy living close to Mina’s parents in a “sleepy” southern California beach community where they can live the lifestyle they want.

3 takeaways and strategies to guide your search.

Mina and Trevor’s boomerang U.S.-to-Canada move made them realize the place they had left behind was where they were meant to be. But they had to take the long way around to arrive at this discovery – one that cost them a substantial amount of money, time and anguish.

What steps could they have taken to avert a wrong move? And what can you take away from their experience to inform your own search for the right place to move?

To answer these pressing questions, I’m highlighting 3 takeaways from Mina and Trevor’s boomerang U.S.-to-Canada move, along with 3 expert strategies that could have helped their search and that you can use right now to guide YOUR search for the perfect retirement location.

1. Pay close attention to where you get your information.

Online research can make or break the search for your perfect location to retire.

Online research works for you when you know exactly what data to look for and where to find the most accurate information. And it can really work against you when you don’t. The secret to research success lies in the ability to discern between fact and fiction. That way you don’t act based on misleading or bad information.

For example, faulty online research was largely to blame for Mina and Trevor’s boomerang U.S.-to-Canada move. Had they gathered accurate information on critical issues such as immigration, healthcare insurance, and housing costs in the first place, they could have been spared the cost and hassle of a wrong move.

2. Align your priorities with who you are now.

You are not the same person now as you were in your twenties.

In all likelihood, your priorities have shifted over the last few decades. This is why it’s so important to stop to take inventory BEFORE launching the search for your perfect location to retire. Dig deep. Ask yourself what matters most to you. Who are you now? What is your vision for retirement?

Mina and Trevor’s boomerang U.S.-to-Canada move happened in part because they allowed outdated priorities to drive their decision. Had they stopped at the beginning to reflect on and articulate their current priorities, interests, needs and goals, they would have realized that many of the community attributes they had assumed were important to them no longer were.

Your search needs to be built on a solid foundation. That’s why exploring and identifying your current priorities, needs, interests and goals is so important to creating a roadmap to your most promising locations to retire!

3. Be rigorous and intentional with your scouting visits.

Although online research is a vital step in your search for the right place to live, it has its limits.

The only way to really get a feel for a place is to scout it out in person. Scouting visits bring living in a place out of the realm of ideas and into the realm of reality. But there’s a science to carrying out a scouting visit that will yield the information you’ll need to make the best decision.

Mina and Trevor scouted out Toronto before moving there, but their vetting process was lax. They figured they’d be at home in Toronto based on their previous experiences. Had their scouting visit been more rigorous and intentional, they might have thought twice before embarking upon their boomerang U.S.-to-Canada move.

Get top-notch results from Your Place Finder!

Your Place Finder blends the science of prospect research and strategic planning and the art of one on one consulting and coaching to help you track down your perfect retirement location both quickly and cost effectively. Learn more about the PlaceFinder Program here!

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About the Author

I founded Your Place Finder in 2017 to help retirees and almost retirees like you anticipate and overcome the pitfalls and challenges – and reap the rich rewards – of finding the perfect location to move for retirement.

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