Jill on Money with Jill Schlesinger Feeling Stuck as I Approach Retirement
8 snips
Dec 30, 2025 Jackie, a 63-year-old listener, shares her concerns about retirement after losing money in the past. She discusses her transition from saving to spending and feels stuck. They delve into topics like Social Security timing, with Jill suggesting a strategic delay until 70. They also talk about the importance of reassessing investment allocations and the emotional hurdles of decumulation. Jill encourages Jackie to gradually reintroduce market exposure and consider Roth conversions while in a low tax bracket. It's a candid discussion about navigating the complexities of retirement planning.
AI Snips
Chapters
Transcript
Episode notes
Fear From Past Market Crash
- Jackie got spooked years ago when the market crashed and moved most holdings into safe, stable-value funds.
- That fear now leaves her reluctant to reinvest despite approaching retirement at 65.
Count Guaranteed Income First
- Tally guaranteed and predictable income sources first to assess how much of your expenses are covered.
- Jackie and her husband nearly cover their needs with pension, business income, and Social Security projected at age 67.
Convert IRA To Roth Strategically
- Consider converting some of your husband's IRA to a Roth while you're in a low tax year to lock in tax-free growth.
- Convert only enough each year to stay within the 12% tax bracket and pay taxes from non-retirement cash.