Jill on Money with Jill Schlesinger Do We Have Enough To Retire at My Age 59.5?
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Sep 8, 2025 The conversation dives into navigating retirement finances for those in their mid-fifties, emphasizing careful planning for healthcare and asset management. There's a thoughtful discussion about the role of inheritances in retirement plans and the uncertainties tied to them. The podcast also touches on the importance of estate planning, especially for blended families, and encourages younger listeners to secure their financial futures. A listener shares their desire to retire early and explores investment strategies like Roth conversions.
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Listeners Considering Earlier Retirement
- Derek and his wife are mid-50s, working full-time and wondering if they can retire earlier than planned.
- He is considering getting a CFP and small post-retirement work, while she may continue working depending on job security.
Tax Mix Drives Strategy
- Their portfolio is heavily weighted to pre-tax accounts which affects tax and withdrawal strategy.
- Significant Roth and brokerage balances plus low mortgage debt create flexibility for early retirement options.
Factor Healthcare Timing Into Retirement
- Keep employer health coverage plans in mind when timing retirement since healthcare is expensive before Medicare.
- Plan for one spouse to work longer if needed to maintain benefits until age 65.