Deciding to hang up your boots and finally enjoy the fruits of your labour is one of life’s greatest harvests. Deciding when it’s time to take that step requires a hard look at your finances.
Many Canadian workers who are approaching retirement feel unprepared. A recent BMO Financial Group survey found that 76% of Canadians say they’re worried they won’t have enough money in retirement amid rising prices (1).
Another study by the Healthcare of Ontario Pension Plan (HOOPP) and Abacus Data reveals 59% of working Canadians believe they may never retire due to their financial situation (2). These studies showcase the widespread uncertainty and pressure many Canadians feel as they try to “reap what they sowed” during their professional years.
In an exclusive interview with Money.ca content partner, Moneywise, New York Times bestselling author Morgan Housel shares his take on what to do if you’re feeling behind in preparing for retirement (3). Fresh off the release of his new book, The Art of Spending Money, Housel suggests that instead of taking risks and betting on the market, the best thing you can do is to lower your expectations.
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“The market does not know or care what you need to happen,” Housel told Moneywise. “It’s going to do whatever it’s going to do. So a lot of people in that situation end up taking risks that they can’t endure.”
Here’s how to grow your harvest, without having to neglect or jeopardize your savings.
Risking it all won’t buy you peace of mind
It’s easy to get swept up in the latest money trends, whether it’s the cryptic promises of cryptocurrency or the allure of investing in gold. But when you’re nearing retirement, chasing those get-rich-quick ideas can feel more like gambling with your future.
Sure, crypto and gold have their place in a diversified portfolio, but if you’re banking on them to carry you to your sunset years after 65, it might be time to take a step back.
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“The most likely outcome is that you’re going to blow yourself up in the process of doing it anyway,” Housel said. “So this is one of those things where wealth is what you have minus what you want.”
In the digital era, that’s becoming increasingly true. In 2022, Statistics Canada reported 21% of Canadians aged 65 to 74 were working, with approximately 12% saying it was by choice, whereas 9% claimed it was out of necessity (4).
Meanwhile, the Canada Pension Plan (CPP) only provides a modest income: for new CPP beneficiaries aged 65, maximum monthly amounts are calculated at about $1,433 as of January 2025; however, the average monthly CPP pension amount was estimated at $848.37 (5).
To qualify for the highest CPP payout, you must contribute at or above the maximum pensionable earnings for at least 39 years of your working life, a threshold that changes yearly. In 2025, that threshold was $4,034.10 or 5.9% of your salary, minus $3,500 — whichever is lower (6).
These amounts could leave mature workers feeling concerned they’re too far behind to reach their retirement milestone, and they may start considering risky investments in order to catch up.
Instead, the smarter move may be to redefine what’s “enough” for you. That dream boat or luxury car might get swapped for something smaller and more practical.
Read more: Here are 5 expenses that Canadians (almost) always overpay for — and very quickly regret. How many are hurting you?
The Morgan Housel playbook
When it comes to investing for the long haul, Housel emphasized a financial harvest that’s he believes will get you through your retirement.
“The variable that I want to maximize with my investments is endurance and longevity,” Housel said. “I know that if I can be an average investor for the next 50 years, I will achieve every financial goal that I have and then some.”
Housel’s entire net worth is built on that strategy. His portfolio consists of four pillars: house, cash, index funds and shares of Markel — where he’s on the board. “It’s as simple and boring and plain vanilla as it gets,” he admitted.
Yet, that’s the secret. Instead of reacting, he builds his plan market fluctuations, which are inevitable. You don’t have to find the next Tesla or foresee when to buy or sell. A portfolio built around low-cost index funds, steady contributions and a strong cash cushion can quietly help you build up your nest egg.
That doesn’t mean you shouldn’t adjust your plan accordingly. Housel suggests taking the occasional pause to review your portfolio and see if it still aligns with your goals as retirement nears. The goal isn’t to eliminate risk, but to make sure your financial harvest can withstand the waves of drought or pestilence without going to pot.
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If you find yourself tempted by the latest “can’t miss” trend, take a breath. Ask yourself whether the trend adds endurance or complicates things. Because, as Housel reminds us, wealth doesn’t come from the flashiest trades or the trendiest assets. It comes from consistency, patience and understanding that the most powerful investment strategy might just be the one that lets you sleep at night.
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Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
BMO (1); Healthcare of Ontario Pension Plan (2); Moneywise (3); Statistics Canada (4); Government of Canada (5); Wealthsimple (6)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.