Motley Fool Money

Two Retirement Experts Discuss How They’ll Decide When to Retire

54 snips
Jan 31, 2026
Dan Caplinger, Motley Fool contributor and former financial planner, shares decades of retirement planning experience. They discuss the emotional uncertainty of stopping work. They talk spreadsheets and calculators used to validate plans. They cover healthcare before Medicare, phased transitions versus full retirement, and preparing socially for life after work.
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ADVICE

Create Financial Escape Valves

  • Build multiple 'escape valves' or slush funds to handle unknown future expenses.
  • Use spreadsheets and calculators to stress-test scenarios and preserve your core budget.
ADVICE

Verify Numbers With Trusted Calculators

  • Cross-check your spreadsheets with reputable online calculators like the Social Security site and Motley Fool tools.
  • Then customize assumptions to match your unique preferences and risk tolerance.
INSIGHT

Money Alone Rarely Resolves Retirement Doubts

  • Even with ample savings, retirees often feel they never have enough due to unknown future risks.
  • Emotional uncertainty about lifestyle and contingencies can delay the retirement decision.
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