Jill on Money with Jill Schlesinger When Can I Downsize My Job?
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Jan 15, 2026 In this engaging discussion, Paul from Chicago, a 57-year-old contemplating a more meaningful and less stressful second act, seeks guidance on downshifting in his career. He explores the intricacies of his savings, retirement accounts, and the potential of leveraging his home equity. Jill offers strategic advice on managing college costs, emphasizes testing a new location by renting first, and underscores the significance of engaging a financial planner for tailored insights. Their conversation is enlightening for anyone considering a mid-career pivot.
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Plan A Gradual Off-Ramp
- Do plan a glide path to reduce work rather than quitting abruptly and protect your finances while you downshift.
- Consider a 3–5 year timeline to transition into lower-stress, meaningful work while still earning and saving.
Savings Create Flexibility
- High current earnings plus disciplined retirement contributions create flexibility for an earlier downshift.
- Maxing 401(k)s and shifting to Roth contributions boosts retirement tax diversification.
Count Only Vested Balances
- Do inventory all retirement balances and treat vested deferred comp conservatively when planning to leave.
- Only count vested amounts toward near-term plans because unvested funds may be forfeited on exit.