Two Sides of FI

Our Biggest Fears About Early Retirement

Jun 1, 2025
What are the scariest aspects of early retirement? Finances might be just the tip of the iceberg. The conversation dives into fears about identity shifts, social isolation, and the societal judgments that come when leaving work behind. Listeners discover how to navigate unexpected costs, adjust budgets, and even maintain social connections. The hosts share their personal experiences, emphasizing that emotional readiness can be just as important as financial security when taking the leap into a new lifestyle.
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INSIGHT

Managing Financial Fears

  • Financial fears at early retirement mainly center on sequence risk and market drops.
  • Strategies like conservative asset allocation and CAPE-based withdrawals help manage this anxiety.
ANECDOTE

Handling Unexpected Expenses

  • Unexpected expenses often arise, such as car repairs for adult children.
  • Jason used income from options trading to handle unplanned costs smoothly.
ADVICE

Plan for Rising Healthcare Costs

  • Plan for rising healthcare premiums in early retirement by adjusting your projections.
  • Use tools like Projection Lab to model increasing healthcare costs above inflation.
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