Jill on Money with Jill Schlesinger Taking Advantage of a Unique Year
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Dec 26, 2025 Jennifer, a former high earner, took a planned year off work, creating an opportunity for strategic financial planning. She explores whether her unique low-income year allows for a Roth conversion to minimize taxes. Jill advises her to roll over her 457 account to Vanguard and consolidate her investments while discussing ongoing conversion strategies. They also touch on charity planning and ensuring her estate documents are updated, all while navigating the complexities of retirement planning in this transition year.
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Taking A Planned Gap Year
- Jennifer took a planned gap year after leaving a 17-year job and lived off savings while doing consulting and volunteering.
- She described improved sleep, travel, and gradual readiness to return to work after about ten months.
Work Timeline Shapes Conversion Strategy
- Jennifer can comfortably live on her new salary of about $190–200k and plans to work roughly another decade.
- That horizon makes aggressive Roth conversion planning and long-term retirement projections practical.
Liquidity Enables Tax-Planning Flexibility
- Jennifer has diversified liquid assets across retirement, brokerage, and cash totaling roughly $2 million.
- That liquidity gives flexibility to pay conversion taxes and pursue Roth strategies without jeopardizing living expenses.