Unconventional Wisdom

Multi-Millionaire's Dilemma: Stay in Stocks or Go Conservative After Retiring?

April 23, 2026·15 min
Episode Description from the Publisher

You've worked hard, built up a few million dollars, and now you're seventy-five, retired, and staring at your portfolio wondering — do I really need to keep riding the stock market rollercoaster?  Or is it finally time to play it safe? That's the multi-millionaire's dilemma, and it's a lot more common than you might think. We have seen it many times. Far more money than you will spend during your life.  Continue investing for growth or switch to conservative? In my latest video, podcast episode and blog post you'll learn: What is the "Multi-Millionaires' Dilemma"? Why consider going conservative? Why consider continuing to invest for growth? What is the maximum that equities are likely to be down at the end of your life? What are the odds equities are down over periods of 5, 10, 15 or 20 years? How much growth are you likely giving up by switching from equities to GICs? Can the numbers make this clearer? What is your money for? Why Ed will be 100% equities his entire life.

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