4 Tax Moves That Can Save You 6 Figures - Part 1 of 2 episode artwork

EPISODE · Oct 13, 2025 · 26 MIN

4 Tax Moves That Can Save You 6 Figures - Part 1 of 2

from Your Money Guide on the Side · host Tyler Gardner

Taxes in your 50s may not be cocktail party conversation, but they can make or break your retirement plan. In this episode, I kick off a two-part series on the smartest tax moves to make once the kids are (hopefully) off your payroll and you’re staring down retirement. In Part One, we cover four essential strategies: Roth Conversions: Why your 50s and early 60s may be the perfect window to pay taxes on your terms, not Uncle Sam’s. Withdrawal Sequencing: The order in which you raid your taxable, pretax, and Roth accounts can extend your portfolio by years. Tax-Efficient Investing: How to avoid paying tax on “phantom income” by using ETFs, low-turnover funds, and muni bonds. Tax Loss Harvesting: Turning portfolio lemons into lemonade by using losses to offset gains and shrink your tax bill. Think of this episode as a tax tune-up: no jargon—just practical strategies that can save you tens or even hundreds of thousands over your lifetime. And this is only Part One. Next week, we’ll cover the HSA triple play, Social Security timing, and two bonus strategies for the charitably inclined and family-minded. 👉 Subscribe so you don’t miss Part Two, and if you’re finding these episodes helpful, consider leaving a quick review. It helps more people discover the show — and keeps me from muttering about Roth IRAs to my dogs in the Vermont woods entirely in vain.

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4 Tax Moves That Can Save You 6 Figures - Part 1 of 2

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This episode is 26 minutes long.

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This episode was published on October 13, 2025.

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Taxes in your 50s may not be cocktail party conversation, but they can make or break your retirement plan. In this episode, I kick off a two-part series on the smartest tax moves to make once the kids are (hopefully) off your payroll and you’re...

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