Retirement Answer Man

Listener Questions: What Should I Be Doing When I'm Two Years from Retirement?

20 snips
Apr 15, 2026
Practical steps for the two-years-out retirement timeline. Clear guidance on handling inflation risk and hedging strategies. How to design your retirement life first, then map income from Social Security and pensions. Tips on positioning accounts, building after-tax cash for flexibility, and timing Roth conversions to reduce tax and Medicare surprises.
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ADVICE

Keep Enough Stocks To Hedge Inflation

  • Do not get too conservative with investments before retirement because inflation is a long-term risk that erodes purchasing power.
  • Maintain meaningful equity exposure so your portfolio can act as an inflation hedge as Roger recommends with Jeremy Siegel's research.
ANECDOTE

Jim's Injury Taught Activity Diversification

  • Jim retired at 58 and planned active hobbies but suffered a back injury that limited physical activities initially.
  • He pivoted to non-physical pursuits and learned to diversify retirement activities as a safety net.
ADVICE

Make A Detailed Preretirement Budget

  • Do build a high-fidelity budget for your base great life now, listing monthly expenses for housing, healthcare, travel, and food.
  • Map discretionary wants with timing and dollars so you can test feasibility two years before retiring.
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