Q&A: I’m Burned Out But Not Quite Ready to Retire

2026-02-10

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#688: Anonymous: "Anonymous Sheryl" is 38, mortgage-free and exhausted after 15 years of teaching. She’s torn between pushing a few more years toward FIRE or switching to relief teaching now for better work-life balance. How do you trade speed to FIRE for sustainability without blowing up the plan? Anonymous : "Anonymous Ray" hired a bank portfolio manager but isn’t sure how to judge the results after just a few years. With mixed performance, dividend-heavy funds and higher fees, when is it fair to ...

#688: Anonymous: "Anonymous Sheryl" is 38, mortgage-free and exhausted after 15 years of teaching. She’s torn between pushing a few more years toward FIRE or switching to relief teaching now for better work-life balance. How do you trade speed to FIRE for sustainability without blowing up the plan?

Anonymous : "Anonymous Ray" hired a bank portfolio manager but isn’t sure how to judge the results after just a few years. With mixed performance, dividend-heavy funds and higher fees, when is it fair to evaluate a manager — and would a simple index ETF outperform?

Nathan: Nathan’s 14-year-old just earned his first W-2 income, and Nathan wants to jump-start his son’s investing journey with a Roth IRA. But with household income above the Roth limits, is there a legal way to make this work without sacrificing the child tax credit?

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