How to Make Financial Mistakes and Still FIRE! | Doug Cunnington of Mile High FI Podcast | 243

What if getting to FI has less to do with avoiding mistakes and more to do with surviving them without setting too much money on fire? Bill joins Doug Cunnington of Mile High FI for a refreshingly imperfect look at the financial decisions they wish they could redo. Between them: credit card debt, lifestyle inflation, whole life insurance, expensive advisors, an underwater dream house, a foreclosure, selling stocks at exactly the wrong time, and the very FI-specific problem of eventually becoming too good at saving. But this isn't just a financial confession booth. Bill and Doug compare what actually helped them recover, why "good enough" beats perfect, and how both still reached FI despite getting plenty wrong along the way.

This episode covers

Why financial mistakes are often part of the learning process rather than proof you've failed Bill's late-start wake-up at 50 and Doug's accidental path into the FI community How missing financial education can turn needs, wants, and lifestyle inflation upside down Whole life insurance, expensive advisors, and the opportunity cost of bad financial products When DIY investing works—and when professional advice can uncover expensive blind spots Doug's housing mistake, rental losses, and strategic foreclosure Bill's over-renovated home, car payments, debt, and the cost of "too much house" Investing mistakes including selling during crashes and chasing recent winners Why aggressive savers can eventually struggle to give themselves permission to spend Bill's "fog of FI," phased retirement, and learning to use financial independence instead of merely reaching it

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