Episodes

If you have a specific subject on your mind, you can use our complete episode index, organized by topic, to find the conversation you're looking for.

Wealth Psychology in Retirement Garrett Crawford, CFP® Wealth Psychology in Retirement Garrett Crawford, CFP®

One More Year Syndrome: Why Proactive Tax Planning is the Cure for High-Net-Worth Retirees

Could staying at your desk for just six extra months be worth 30 years of previous savings? Discover an interesting math discussion behind a 2018 NBER study called The Power of Working Longer and why it’s important for high-net-worth retirees to take note. In this episode of Retirement Tax Matters, Garrett Crawford, CFP® breaks down the three levers of One More Year Syndrome and the proactive tax-return-driven strategies you might consider if you encounter this.

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Wealth Psychology in Retirement Garrett Crawford, CFP® Wealth Psychology in Retirement Garrett Crawford, CFP®

Why Converting Your Traditional IRA to Roth Might Feel Like Paying Off Your Home Mortgage

Episode 24 of Retirement Tax Matters was inspired by Dave Ramsey’s Debt-Free Scream and the parallels we see when high-net-worth retirees settle their tax liability with the IRS. Learn why the psychological victory of a Roth conversion often outweighs the raw math of a calculator.

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Wealth Psychology in Retirement Garrett Crawford, CFP® Wealth Psychology in Retirement Garrett Crawford, CFP®

The Downside of Tax Minimization: Why Paying Taxes Can Be a Winning Strategy

Episode 16 of Retirement Tax Matters tackles the financial psychology of tax aversion—the emotional resistance high-net-worth retirees often feel toward paying taxes, even when it might be the most strategic move. We explore why successful savers, who built wealth by minimizing costs, often struggle to execute strategies like Roth conversions or selling highly appreciated stock because they view paying tax dollars as a loss of capital.

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