508: More Control, Less Surprise: A Real Retirement Tax Wake-Up Call

Retire With Purpose - The Retirement Podcast

What if you did everything “right” in retirement, but were still left surprised? That’s exactly what happened to Fritz Gilbert, one of our favorite past podcast guests. In this episode, we unpack his recent article, “My Biggest Surprise in Retirement,” and explore why his carefully planned Roth conversions didn’t make the impact he expected. This conversation is for anyone who wants to stay in the driver’s seat—no surprises, no backseat driving from Uncle Sam—just thoughtful, purpose-driven planning.

In this episode, we discuss:

• Why Roth conversions may not reduce your tax-deferred balance as expected
• Why waiting until retirement to convert might be too late
• Strategic conversions = lower RMDs, Medicare premiums, and taxes for heirs
• The ripple effects of taxes: Medicare IRMAA, Social Security, legacy

Today's article is from The Retirement Manifesto blog titled, My Biggest Surprise in Retirement. 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/508

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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