
Paul (Caller from Chicago)
Private individual caller featured in the episode seeking financial and retirement planning advice about downshifting work and managing savings, pensions, and real estate.
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Jan 15, 2026 • 21min
When Can I Downsize My Job?
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.


