Jill on Money with Jill Schlesinger Can I Quit My Job at 57?
9 snips
Mar 27, 2026 Anthony, a 57-year-old caller balancing retirement accounts, brokerage, HSA and cash, seeks clarity about leaving work early. He discusses renting vs buying, timing a sabbatical around bonuses, short-term cash and health insurance plans. The conversation covers using Rule of 55, withdrawal timing from 401(k)s, tax strategy, and updating estate paperwork.
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Take A Gap Year To Reorient Before Quitting
- Do plan a sabbatical instead of immediate permanent exit if you want to rediscover passions and then pursue part-time work later.
- Anthony envisions a one-year gap to take classes and then transition to lower-paying, more satisfying part-time work.
Large Nest Egg Enables Flexible Retirement Timing
- High savings plus disciplined living gives flexibility to quit even before typical retirement age.
- Anthony has roughly $3M across accounts despite a $150k base salary, enabling many lifestyle options.
Convert Short Term Cash Before Leaving Work
- Do build a short runway in cash and move brokerage equity to safe liquid holdings before quitting so you can cover immediate living and insurance costs.
- Jill recommends two years of cash from brokerage and savings and buying health insurance while not working.