Jill on Money with Jill Schlesinger Moving From Saving to Spending
4 snips
Mar 17, 2026 Chris, a recent retiree navigating the shift from saving to spending, calls in with questions about withdrawals, Roth conversions, and asset allocation. The conversation covers tax-smart conversion timing, using savings to pay conversion taxes, pension and Social Security timing, charitable giving via donor-advised funds, and simplifying accounts and fees. Practical choices and next steps are explored in short, actionable talk.
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Do Roth Conversions In Low Income Years
- Do consider doing Roth conversions when your taxable income is temporarily low to lock in lower tax rates today.
- Jill recommends converting an amount (example: $150,000) this year while Chris is likely in a lower bracket before his pension and Social Security raise taxable income.
Caller Profile Shows Strong Savings And Low Spending
- Chris is 61, single, retired 1.5 years, with a $600k Roth in a 401, $1.1M taxable in the 401, plus brokerage Roth $250k and taxable $900k, $125k high-yield cash and $250k laddered CDs.
- He spends about $9–10k/month, draws from Fidelity 401 and brokerage, has a paid-off $1.1M house and a pension option starting now or next year ($3,500 rising to $3,800).
Pay Conversion Taxes From Cash Reserves
- Do use cash reserves to pay the tax on conversions rather than selling investments, preserving market exposure.
- Jill suggests using high-yield savings and rolling maturing CDs into that cushion to fund conversion tax bills.