Your Money Guide on the Side

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


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Your 50s are a tax-planning sweet spot—a decade when smart strategies can save you tens or even hundreds of thousands over the course of retirement. In this episode, Part Two of our two-part series, we explore four advanced but practical moves to keep more of your money compounding where it belongs.

Here’s what we cover in this episode:

  • The HSA Triple Play: Why this account is the most underrated retirement tool, and how to turn it into a stealth IRA with triple tax benefits.
  • Social Security Timing & Taxes: How your claiming age affects not just your benefit but how much the IRS quietly takes back.
  • Charitable Giving with Donor-Advised Funds: A Costco-sized deduction now, with the ability to give on your terms for years. Plus, how Qualified Charitable Distributions can kill two birds with one IRA.
  • Bracket Shifting by Gifting to Kids: Move money to lower tax brackets within your family—legally—while supporting education, housing, or even a responsible jet ski purchase.
  • Together with Part One (Roth conversions, withdrawal sequencing, and tax-efficient investing), this gives you a full seven-strategy toolkit for your 50s. No gimmicks, no offshore shell games—just thoughtful planning that keeps more money in your pocket and less in Uncle Sam’s.

    👉 If this series has been helpful, please leave a review or share it with a friend. It’s the best way to help the show grow—and it keeps me from muttering about Roth conversions to my dogs in the Vermont woods without witnesses.


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    Your Money Guide on the SideBy Tyler Gardner

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