Jill on Money with Jill Schlesinger Do I Need to Find Another Job?
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Feb 27, 2026 Jane, recently laid off in 2024, is seeking practical money direction after severance. The conversation covers housing decisions with a low mortgage rate, heavy ESPP stock holdings and liquidity concerns, retirement account choices including a cash-balance pension, tax timing for selling stock, and options for part-time work to bridge expenses.
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Laid Off at 57 Then Took a Career Break
- Jane was laid off in 2024 and initially used a generous severance parked in a high-yield money market while she job-searched.
- She took a break, traveled, then resumed interviewing and reached final rounds but hasn’t secured a role yet.
Kept ESPP For Dividends That Covered Property Taxes
- Jane holds $148,000 in ESPP shares and used dividends to cover half her property taxes, showing dependence on that stock for cash flow.
- She kept shares after learning colleagues sold, partly to maintain income from dividends.
Sell ESPP Now To Boost Emergency Reserve
- Sell at least half the ESPP shares now while taxable income is low to lock in cash and take advantage of lower tax brackets.
- Use proceeds to beef up the severance/emergency reserve and cover living costs before tapping retirement accounts.