508: More Control, Less Surprise: A Real Retirement Tax Wake-Up Call
Retire With Purpose - The Retirement Podcast
Casey Weade
4.7 • 556 Ratings
🗓️ 4 July 2025
⏱️ 23 minutes
🧾️ Download transcript
Summary
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
📧 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
Transcript
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| 0:00.0 | Nobody wants to be surprised in retirement. |
| 0:02.9 | Today, we discuss one of our past podcast guests, Fritz Gilbert's biggest retirement surprise. |
| 0:18.2 | Hey, this is Casey. |
| 0:19.9 | Welcome to the show. Where does my mission to deliver clarity and purpose and elevate meaning in your life? If you're wondering what that means, well, that means we have both financial and non-financial conversations having to do with freedom after 50. Now, if you're looking specifically for those non-financial conversations, I want you to know what to look out for. Check out those Freedom After 50 episodes. That is how they're titled. That's where we bring in our very own certified retirement coach, Les McDaniel. And we take deep dives into the non-financial, more emotional side of retirement, if you will, and beyond. We also bring you |
| 0:54.3 | world-class guests, weekend and week out, and a variety of different topics. And then today, |
| 0:59.4 | which is every other Friday, between our freedom after 50 episodes, I get together with my |
| 1:04.4 | good friend and fellow certified financial planner practitioner, Marshall Johnson, |
| 1:09.0 | and we discuss more of the financial side of retirement. |
| 1:12.8 | Marshall, we've been talking about naming this one. We didn't get a name like less. So I'm feeling |
| 1:18.2 | a little bit left out. Yeah, we need to come up with one. Maybe this is some numbers or something. |
| 1:22.4 | I like that. So if you got any great ideas, just go ahead and shoot us an email over here at Howard Bailey. Visit us at the website, Howard Bailey.com, and shoot us over what you think we should title these episodes. Michael Kitsies already has my favorite blog name. What's that? Nerds I View. Okay. Well, we're not going to be able to use that one. We're not going to be able to use that one. That one's a good one. But we are going to have nerd out. |
| 1:44.7 | So maybe we'll be nerdy in some way, shape or four. But these conversations, most of our conversations are going to come out of things that we've read recently. And the things that Marshall and I are reading, we like to pass on to you as our listener. and we put that in an email every single Friday called Weekend Reading Free Tyrese. |
| 2:03.7 | Then email hits your inbox every day. on to you as our listener, and we put that in an email every single Friday called Weekend |
| 2:02.3 | Reading for Retirees, then email hits your inbox every Friday, four articles, trending |
| 2:06.6 | topics, summaries, takeaways, and all kinds of other great resources. If you sign up right |
| 2:11.8 | now, we'll also send you a free digital copy of my Wall Street Journal, Best Sallic Book, |
| 2:15.7 | job optional. Just text us the key letters, |
| 2:18.1 | W.R. to 888-59-4491. Now, let's get in to the brass tax of things. We're talking about a blog |
| 2:27.6 | post that was written here June 12th of 2025 by Fritz Gilbert, one of our favorite past podcast guest. It is titled My Biggest Surprise in |
| 2:38.5 | Retirement. The reason that I loved having Fritz on is because he's uniquely chronicled his |
| 2:45.6 | retirement experience from pre-retirement and through. He's enjoyed seven years of retirement, and he says it's been |
| 2:54.0 | the best time of his entire life, which I love hearing, and I think it is because he's done so |
... |
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