The Most Dangerous Years of Retirement

The Most Dangerous Years of Retirement

September 4, 2026 · 39 min · Episode 361

About this episode

Bob and Brian discuss the critical first five years of retirement and various financial strategies to consider.

On this episode of Simply Money, Bob and Brian explain why the first five years of retirement can make or break your financial plan, how a rising market can quietly increase the risk in your portfolio, and why having enough money to buy something doesn’t necessarily mean you should. Plus, they tackle tax-loss harvesting pitfalls, managing concentrated company stock, and why today’s mortgage rates shouldn’t be the only factor driving your decision to buy a home.

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Hosts: Bob, Brian

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Organizations: Simply Money, Allworth Financial

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