Mary (caller)
Caller to the show seeking personal finance guidance about slowing down work and retirement planning, describing her situation as a 60-year-old realtor with investments, cash reserves, a pension and Social Security.
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Dec 29, 2025 • 13min
Do I Have Enough to Slow Down?
Mary, a 60-year-old realtor, calls in seeking advice on whether she can afford to slow down her work life. With $1.6M in brokerage accounts and a mortgage-free condo, she discusses her solid financial foundation. They explore spending needs, part-time work options, and the timing for her Social Security benefits. Jill recommends strategic Roth conversions to optimize her tax situation while ensuring Mary's lifestyle goals, including her dream trips to Italy and Sardinia, remain within reach.
