Retiring in Comfort—Without Ever Experiencing a Canadian Winter Again

I haven’t had to scrape frost off my car’s windshield for more than 8 years.

I haven’t had to shovel a snowy path or driveway, and I haven’t had to put on a winter’s jacket–other than during a 2 week Christmas visit to my wife’s family in Pennsylvania.

Eight years.

No cold hands.

No heating the house.

No treacherous driving.

No cold spring wetness.

Ahhh, the luxury of never spending a winter in Canada—ever again.

To be honest, I hate winter. OK—there are a few winter activities I like, but I’d prefer jetting into winter, skiing for a weekend or a week, and then getting the heck out to thaw at Pulau Tioman or Pulau Rawa

I haven’t retired. My wife and I are still working at Singapore American School. But when we decide not to work full-time (the word “retire” sounds too much like dying to me) we’ll spend summers in North America, and we’ll do long term rentals in places like Lombok or Bali, where we can find accommodations for $250 a year. Yeah, you read that right: $250 a year.  We won’t be paying tourist prices. … read more

We might rent a different place every winter—in a different country each time. My wife and I love to travel, meet different people, experience different cultures and soak in perpetual summers.

When we’re no longer teaching in Singapore, we’ll officially move back to Canada where we’ll spend the more pleasant months of the year. We’ll move our money into a Canadian brokerage account, probably “couch potato” our investments (with a 50% bond component) and draw roughly 3-4% of our portfolio each year into our chequing account, for living expenses.

Overall, this lifestyle will allow us to quit working much earlier, giving us far more time with family and friends. In fact, we’ll be around so often, they won’t be able to wait for winter to come.

And when it does come—we’re gone. No more cold Canadian winters for us.

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Andrew Hallam

I’m a financial columnist for Canada’s national paper, The Globe and Mail, as well as for AssetBuilder, a financial service firm based in Texas. I’m also the author of Millionaire Teacher: The Nine Rules of Wealth You Should Have Learned in School (2nd Ed. Wiley 2017) and The Global Expatriate’s Guide To Investing: From Millionaire Teacher to Millionaire Expat (Wiley 2015). My mission is to educate, motivate and inspire people on basic retirement planning and best practices for investing, using evidence-based strategies. I'm happy to comment on your questions. However, please read the Terms of Use, Privacy Policy and the Comments Policy.

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17 Responses

  1. Kevin@InvestItWisely says:

    "And when it does come—we’re gone. No more cold Canadian winters for us." Haha.

    You guys are already long out of the rat race. You do what you love and have the time to travel and enjoy yourselves as well. That is the dream.

    P.S. $250 a year sounds incredibly cheap!

  2. @Kevin@InvestItWisely

    Hey Kevin, the next time you're in SE Asia, hang around and find out what some of the retired expats are paying for accomodations in some of the non tourist areas of Thailand, Indonesia and The Phillippines. In many cases, what tourists pay for one night's accomodation will cover a month. The $250 a year in Lombok is the best deal we've found yet.

  3. Hello Andrew

    I'me not familiar with Lomboc, but having spent some time in the Philippines, I can attest to the very low cost of living and balmy weather. And good beer.

  4. @Andrew @ 101 Centavos

    It's a rough place to put yourself, isn't it Andrew? But I guess some of us have to do it.

  5. It is super cold this year in Canada- did you hear about the -17 degree weather in of all places, Vancouver?! I was shocked- but now it's warm again.

    When do you think you might move back to Canada?

  6. @youngandthrifty

    I heard about the crazy weather you've been having Young. I'm sure glad that I'm not part of it right now. As for moving back, I'm not sure. We like what we're doing, and we're still young. I used to want to retire when I was 43, and I'm 40 now, but we're still enjoying our jobs. Next year I'll be taking a year off to promote a book, which will be fun. We might not be moving back for a really long time. We just know that we don't want any more Canadian winters.

  7. larry macdonald says:

    I have to stand up for Canada and say I would rather be wrapped up in three layers of clothing playing shinny hockey on an outdoor rink for 2-3 hours in -15 celsus weather than parading my knobby knees and fat gut on some tropical beach! No, seriously!

  8. @Andrew – loved the post. Inspirational. Next year, you're going to have your book completed? Of course you'll let us know!?

    Maybe I don't have to travel to Sinapore to visit you, I simply need to wait a few years until you move back? 🙂 Argentina was excellent BTW, you and your wife should visit it if you can someday.

    The other 50% of your portfolio, keep it in dividend-payers I assume?

    @Larry, that was funny.



  9. @larry macdonald

    Everyone knows you used to be a swimsuit model Larry. Well…loads of people know, anyway.

  10. @Financial Cents

    Hey Mark,

    We'd love to see Argentina. My wife speaks Spanish and loves South America, so we may end up living there for a time. As for my portfolio, yeah, it's going to be pretty low maintenance—much like the one I have right now.

  11. Terry Pratt says:

    Are there any countries where a single low-income retired North American ($10K-$15K annual income) could live reasonably well?

    Are there any countries where a low-income working-age North American would be allowed to work and earn income?

  12. Hi Terry,

    I think the answers to both of your questions are: yes and yes.

    Let me know what you think of this:

  13. Julie says:

    Hi Andrew,

    Great blog. Read your 9 laws to financial freedom. I just ordered your book from Amazon.

    Couldn’t help myself but laugh out loud when I read about this post. I am a Singaporean living in Rossland in BC. Skiing here is great! It’s the very foggy autumn days (I can hardly see beyond 1 metre) and treacherous winter road conditions (yes, the black ice) that horrible.

    Here’s a weather update:

  14. Jeffro says:

    Hi Everyone,

    Do any expats have any TRUSTWORTHY info or first-hand experience with buying overseas real estate — particularly in SE Asia?

    I’m looking into RE markets in SEA and there’s a ton of online material to sift through. Just want to see if I can narrow my focus a little bit.

    Thanks ; )

  15. Mark Holmes says:

    I have retirement question. I often hear the 4% rule, where you can draw 4% of you retirement fund per year and adjust it for inflation each year. But how do you set what 4% is? If I retire at 60 and the market is at its peak, my total portfolio might be worth $1,000,000, then I get to draw $40,000 a year. If I retire at 60, having saved exactly the same amount of money, but the market is at a low and I only have $700,000, then I only get to draw $28,000. How do you judge what 4% is? It’s entirely possible that the $700,000 may rise to $1,000,000 within a relatively short time. It’s also possible the $1,000,000 may drop to $700,000 within a similar time span. At what point do you assess your 4% benchmark? Should you look at the average over the last five years or look at the top and bottom of the last up and down swing?

    • Hi Mark,

      As a retiree, a 40% market drop would only likely affect your portfolio by about 17%…if your money were properly diversified. I would go with the value of the portfolio upon retirement, as my base, and realize that the markets would fluctuate many many times between when I start withdrawing and when I die. But I would be consistent with the amount withdrawn, from the base rate of 4% when I retired, adding amounts to cover inflation. At times, what you take out will be a lot more than 4% of your total, other years, much less.


  16. no one has more first hand experience helping expat investors

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