James (caller)
Caller from North Carolina in his early 50s seeking financial guidance about cutting back work to spend more time with his young child; provides detailed personal financial information used as the basis for advice on the episode.
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6 snips
Dec 2, 2025 • 12min
Can We Cut Back on Work?
Caller James from North Carolina, a dedicated father in his early 50s, seeks financial guidance on cutting back work to spend more time with his young son. He shares details about his $2M retirement investments and minimal cash reserves, sparking a discussion on maintaining liquidity. Jill advises reducing retirement contributions for a cash cushion while balancing current income and future plans. They explore self-employment options and essential insurance coverage, ensuring James is prepared for his family’s financial future.
Jan 28, 2026 • 7min
Should My Parents Buy an Annuity?
James, a concerned son calling about his parents’ retirement, asks whether moving $475K into an annuity is wise. The conversation digs into annuity types, fees, and motives. Experts urge caution, suggest getting a second opinion from a fiduciary, and weigh security versus market risk in short, practical advice.
