Jill on Money with Jill Schlesinger

Retirement After 25 Years, What’s Next?

16 snips
Aug 21, 2025
A listener shares their emotional journey of leaving a 25-year career, highlighting the need for careful planning. The discussion dives into early retirement readiness, examining savings and investments without a pension. Health insurance costs and spending habits are tackled, illustrating their significant role in retirement finance. The importance of rental income and social security benefits is emphasized, aiming to create a balanced retirement lifestyle. The conversation also reflects on the emotional aspects of moving on from a long-standing career.
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ADVICE

Inventory Your Accounts First

  • Do catalogue all your accounts (401k, brokerage, IRA, HSA, savings) before deciding withdrawals.
  • Use those balances to plan taxable timing and withdrawal amounts for early retirement.
ADVICE

Treat Your Mortgage-Free Home As Leverage

  • Do confirm home equity and mortgage status when planning retirement cashflow.
  • Owning the home outright reduces living-cost pressure and increases flexibility.
ADVICE

Include Taxes And Health Costs In Budget

  • Do calculate realistic monthly spending including taxes and health insurance before retiring.
  • Use an annualized number and include projected insurance costs to avoid surprise shortfalls.
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