DiscoverRetire With Purpose - The Retirement Podcast539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions
539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions

539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions

Update: 2025-12-19
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Could a counterintuitive tax move today potentially lead to thousands in savings — or an unexpected tax trap tomorrow? 

In this episode, we discuss: 

  • Why some retirees intentionally harvest capital gains
  • How the 0% bracket really works
  • When it may make sense to pay capital gains taxes now
  • How to evaluate tax gain harvesting vs. Roth conversions using long-term projections
  • Key tax-planning windows before Social Security, RMDs, and spousal filing changes

Today's article is from the Best Interest blog titled, The Numbers Behind Tax-Gain Harvesting. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation.

Show Notes: HowardBailey.com/539

📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu 

📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB

ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

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539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions

539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions

Casey Weade