Leaving Canada Every Winter for 13 Years Has Changed My Life - Here’s How We Do it

Jonathan Goodman
February 11, 2026
10 min read
Jonathan Goodman and Family leaving Canada to live abroad with Boundless Life in Bali

Jonathan Goodman’s latest book is Unhinged Habits: A Counterintuitive Guide for Humans to Have More by Doing Less.


My home is Toronto, but I’m in Indonesia with Boundless Life as you read this.

Each year, for the past 13 consecutive years, my family has fled Canada in winter to live abroad – Greece, Costa Rica, Montenegro, Nicaragua, Uruguay, Mexico, the Dominican Republic and so on. Eight months in the city, four months somewhere else, more or less.

My kids are in public school the first half of the year. We unenroll them when we go abroad. It’s never been a problem. Just a document to submit. All the school secretary tells us is that they can’t guarantee my kids a spot in the same class when we return. That’s never even happened, by the way.

I know others who rent their homes out. We don’t. Instead, we let friends stay there who need a bigger place for a short period of time. For example, after 8 years a nanny for our neighbor was able to bring her husband over to Canada. They’re staying in our house while abroad this year as they begin their new lives together in Canada.

My opinion is that a house becomes a home when it’s full of memories. I can make money elsewhere. I prefer to maximize its specialness. Two years ago a different family was staying and dented the floor. They offered to pay for it to be fixed. I said no. That the damage is a memory of their time and makes our home more special. Maybe I’m weird, but this is how I think.

Jonathan Goodman's family arriving at the Boundless Life Education Center in Sanur Bali

Toronto Is a Hustle – Living Abroad Is a Season

Look, Toronto’s is a hustle culture. People who live here are trying to get ahead. My weeks are full of professional and social responsibilities. It’s great. I love it – until I don’t. Then I need to get the heck out. In the four months when my family lives abroad, we chill. There’s no professional or social responsibilities. My calendar is mostly empty. It’s a slower pace. I read a lot, work out a lot and walk on the beach a lot. And I actually listen to music. Not as background sound. I sit and I listen. It’s great. I love it – until I don’t. Then I crave a more frenetic energy, and we get the heck out and come back to the city.

What started as a yearning for year-round sun evolved into much more: an energizing return, of sorts, to a more seasonal way of living.

I’ve thought a lot about what drives this seasonal exploration. It has little to do with seeing beautiful things and less to do with sitting on airplanes. What it does is break me out of the noise of my routine.

Routines. Patterns. Habits. They’re the invisible architects of our lives. Some serve us well. But they can also trap us in a downward cycle.

With work, my time abroad is a calmer season. I’ve accepted that others are going to choose to work longer hours all-year round and get ahead professionally. The decision I’ve made is a tradeoff––time and adventure with my family in exchange for fewer professional accolades.

Travel is for turning on; vacations are for shutting off. Travel heightens your senses; vacations dull them. Travel is for discovery; vacation, escapism. Living amongst different cultures lets me test living in different ways. And every time that I do it, I return back home more of the person I want to be––a person more true to me.

A family try street food in Sanur Bali

The magic, I’ve found, lies not in choosing one season over the other but in understanding when to shift gears. The structure of Toronto makes meaningful spontaneity possible. Spontaneity provides the raw material that makes structured seasons productive.

Without seasons of intense focus, spontaneity becomes aimless wandering. Without periods of openness, structured seasons become rigid and depleting. Think of it like breathing: you need both the inhale (structure) and exhale (spontaneity) for a complete breath.

Life is short. But it’s deeper than that. Each moment you have just disappears. If you’re not present for it, if you’re stressed out or you’re anxious or you’re thinking about something else, you miss it.

When was the last time you took an art class, just because? In Toronto, my wife Alison would never give herself permission. Too much to do. Too many people to see. The days pass quickly. But whenever we’re in a new place, she explores that side of herself for the season and takes lessons. Mosaic. Silver. Resin. Crochet. Whatever is around.

The biggest benefit of leaving Toronto each winter and returning home in the spring is the discovery of something I now call unhinged habits. Its timing can vary and it isn’t about travel. It’s about having seasons. Which is about contrast. It’s about being excited for the phase you’re in, knowing that it’s not always the phase you’ll be in.

Jonathan Goodman's family exploring Bali with Boundless Life

How I Reset My Calendar Every Season

Every year when I leave and come back, I wipe my calendar clean and build it back up imagining that I don’t have any commitments and that this is the first time that I’ve scheduled anything in.

The order for rebuilding my calendar is:

  1. Fitness comes first.
  2. Have to do.
  3. In-Season season priority.
  4. Need to do.
  5. Outsource / delegate / hire out / ignore.

Every time I clear my calendar I put less back in it. After 12 years, the result’s a mostly empty schedule with three days a week completely clear. This works for me. Your perfect calendar will look different than mine. The only way for you to figure it out is to reliably clear it at least twice a year and repopulate it back from nothing.

Each time you leave one season and enter another, repeat the process starting with an evaluation of how the last period went.

Nothing fancy: phone off; pen and paper; three questions.

  1. What felt good?
  2. Where did I feel resistance?
  3. What can I eliminate next season?

Every iteration gets you closer to your perfect. With each season, you’ll become more aligned with how you work best, more focused on your priority, and more energized because you’ll be doing more of what fuels you, and less of the accumulated crap that inevitably builds up over time.

Jonathan Goodman and wife complete the half marathon in Bali


Most of what we’re doing, I’ve discovered, we don’t really need to be doing; we’ve just been doing it for so long that it’s become a thing that we do, and we don’t ever think about whether it actually needs to be done.

Over the course of a season, you’ll add obligations, tasks and responsibilities. Stuff. Just stuff. You’ll buy stuff. Accumulate stuff. Commit to stuff. But rarely, if ever, will you subtract stuff. If you’re in a never-ending season, odds are, you’ll be never-ending adding. Do I still need to own this? Is that weekly meeting impactful? Am I happy with the time I’m spending with my kids? Every move forced me to pause, hit the reset button, and re-evaluate my priorities not as they were, but as they are.

For more than a decade, as I came and went from Toronto, I wiped my calendar clean and started new. Every time that I left one place, I found myself excited for the next. If I’d felt burned out in Toronto before I left, I was excited to return – not just excited to sleep in my bed again but excited to reset my schedule, reprioritize my commitments and start over.

Dishwashing machines. Central heating. Fresh orange juice. Imagine if you were from another planet with none of those things. Imagine how full of wonder they would all seem. How unjaded you would be by everything amazing in front of you.

Anhedonia is the inability to feel pleasure. An unfeeling. It comes on passively through hedonic adaptation. Do you know that term? No matter how good or how bad something is, constant exposure to it for even a short period of time causes a numbing, a return to a relatively stable, baseline level of happiness.

When something ends, even for a short period of time, and restarts, you feel invigorated and revitalized. There’s no limit for how often you can repeat this cycle. A new project at work. A weekend away from your family. The beginning of a baseball season.

Jonathan Goodman and family go bike riding in Bali

Why Seasonal Living Works

Burnout exists because the clock, combined with the light bulb, created artificial time and removed the seasonality we’ve been hard-wired to crave. This, combined with too much stimulus of the same kinds – the same routine, work, people and pleasures – extended over long enough periods of time leads to a lack of appreciation for even the greatest things.

Everywhere you turn, you are being limited. This can change. You can change your programming. Your life is not a predetermined path but an ongoing conversation between who you are and who you might become. Returning to a seasonal way of living is the beginning of that process.

We are not meant to be static beings, carefully protecting ourselves from the unknown, sheltered by our own habits and creative comforts. We are meant to be wanderers, investigators, persistent questioners of our own limitations. Every time we choose to enter a new season, we choose growth. Every time we embrace contrast, we evolve.

The reason why I love living seasonally is simple. It’s because the starting and stopping nature of seasonal living is the practice of being led gently back to my true self.

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