Jill on Money with Jill Schlesinger Retirement and Leaving a Legacy
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Feb 13, 2026 Mike (Jersey Mike), a retiree with long career savings and multiple pensions, describes his family, incomes, and savings. The conversation covers pension timing, annuity choices, tax issues like RMDs and Roth conversions, and plans to downsize or protect legacy wealth. Practical decisions about investment risk and when to claim fixed income are explored in short, clear advice segments.
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Pensions And Family Context
- Mike (Jersey Mike) described being 54, married, with two college-age children while his wife already retired and receiving a pension.
- He and his wife plan to retire together with combined pensions and significant savings.
Big Pots Mean Big Tax Issues
- Mike has large investable assets including joint savings, rollover IRA, annuity, and deferred comp totaling millions.
- Jill points out that big pension and retirement pots create both freedom and future tax challenges.
Handle Non‑Qualified Annuity Carefully
- For the non‑qualified annuity, Jill recommends separating or moving its proceeds into joint accounts rather than annuitizing if undesirable.
- She warns annuity gains are taxed as ordinary income, not capital gains.