Jan 7, 2026
Deciding when to hang up your boots and finally enjoy the fruits of your labor is one of life’s greatest harvests; it’s also one that deserves a hard look at your finances.
A new Bankrate survey shows that 58% of Americans feel their retirement savings are falling behind, leaving many soon-to-be retirees at a crossroads as they try to reap what they sowed. (1)
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In an exclusive interview with Moneywise, New York Times bestselling author Morgan Housel — whose new book, The Art of Spending Money, shares his take on what to do if you’re feeling behind on retirement. (2) Instead of taking risks and betting on the market, the best thing you can do is lower your expectations.
“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 leave your savings lying fallow.
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 what wealth is, is what you have minus what you want.”
In the digital era, that’s becoming increasingly true. According to Axios’ analysis of Bureau of Labor Statistics data, nearly 19% of Americans aged 65 and older were still working in 2024. (3) Social Security helps, but only so much. The average retired worker receives about $1,980 per month, or roughly $23,760 per year, according to the Social Security Administration.
Instead of trying to risk it all to play catch-up, the smarter move may be to redefine what is enough for you. That dream boat or luxury car might get swapped for something smaller and more practical.
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The Housel playbook
When it comes to investing for the long haul, Housel emphasized a financial harvest that’s going to 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.
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“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 around it. He said he knows that market downturns aren’t anomalies; they’re 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 suggested taking the occasional pause to check if your portfolio 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.
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.
Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editoriacl ethics and guidelines.
Bankrate (1); Moneywise (2); Axios (3); Social Security (4).
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Victoria Vesovski is a Toronto-based Staff Reporter at Moneywise, where she covers the intersection of personal finance, lifestyle and trending news. She holds an Honours Bachelor of Arts from the University of Toronto, a postgraduate certificate in Publishing from Toronto Metropolitan University and a Master’s degree in American Journalism from New York University’s Arthur L. Carter Journalism Institute. Her work has been featured in publications including Apple News, Yahoo Finance, MSN Money, Her Campus Media and The Click.
