Jill on Money with Jill Schlesinger Do I Have Enough to Slow Down?
Dec 29, 2025
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.
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Sold Townhouse, Bought Mortgage-Free Condo
- Mary sold a townhouse and bought a two-bedroom condo outright, leaving her mortgage-free.
- She also holds about $1.6M in investments plus $500k in cash, giving her strong flexibility.
Bridge Slowdown With Cash And Roth Conversions
- Use your cash cushion to bridge a slower work phase and cover living expenses without strain.
- Withdraw modestly and plan Roth conversions while your taxable income stays low to reduce future taxes.
Convert Now To Avoid Larger Future Tax Hits
- Expect pre-tax retirement balances to grow and push you into higher tax brackets later in retirement.
- Convert some pre-tax funds to Roth gradually now to avoid bigger tax hits when required minimum distributions kick in.