Is working one more year the smartest move—or the wrong tradeoff? In this episode of The Modern Retirement Playbook, Jason Matthews breaks down the financial, tax, healthcare, and emotional considerations behind delaying retirement. The conversation explores how one extra year of income can affect Social Security, 401(k) contributions, taxes, and guaranteed income planning, while also weighing health, family responsibilities, and lifestyle goals. Jason also discusses the “sandwich generation,” market volatility near retirement, and why emotional readiness matters just as much as the numbers. It’s a thoughtful look at how timing, planning, and personal priorities intersect at the retirement decision point.

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