508: More Control, Less Surprise: A Real Retirement Tax Wake-Up Call
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
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507: Freedom After 50: You’re Not Looking for Advice—You’re Looking for Alignment, Part 2
In this powerful follow-up episode, Casey Weade and Certified Retirement Coach Les McDaniel return to explore the deeper question behind advice-seeking: Are you truly looking for direction, or for alignment with your values? Drawing from real-life coaching stories, they unpack six invitations to help you pause, reflect, and realign your financial decisions with your life’s purpose. In this episode, we discuss: How to ask better questions Ways to elevate your emotional awareness How to separate valuable advice from projection-based advice Today's article is from our very own blog post which you can find here. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore how aligning advice with your core values leads to better financial decisions. Show Notes: HowardBailey.com/507 📧 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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506: The Surplus Bucket Strategy: A Way to Spend More Confidently in Retirement
If you're like many retirees we meet with, you may struggle to spend confidently in retirement, even when you've saved enough. Here, we explore a potential strategy: an alternative to the annuity-based "License to Spend" model. In this episode, we discuss: The dynamics of underspending in retirement How to apply the “Funded Status Metric” and “Surplus Bucket” to your income plan Pros and cons of leveraging this strategy A refresher of the “Funded Ratio” How to find an income strategy that aligns with your values Today's article is from Advisor Perspectives titled, Use the Funded Status Metric & A ‘Surplus Bucket’ to Increase Spending 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/506 📧 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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505: Freedom After 50: You’re Not Looking for Advice—You’re Looking for Alignment
Understanding your own story is the missing link between receiving advice and applying it meaningfully. If you’ve ever felt stuck between wanting direction and feeling overwhelmed by options, this episode offers a practical path toward clarity, purpose, and peaceful resilience. In this episode, we discuss: Advice vs. application A 3-step advice framework Advice overload Why incomplete context = incomplete advice Today's article is from our very own blog post which you can find here. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to discuss how knowing your story can turn generic advice into meaningful action. Show Notes: RetireWithPurpose.com/505 📧 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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504: How to Stay Sharp and Prevent Cognitive Decline in Retirement with Dr. Ross Andel
Today, I'm speaking with Dr. Ross Andel. Dr. Andel is a gerontologist, professor, and director of the PhD program at Arizona State University. Ross has spent decades researching aging, memory, and lifestyle-related cognitive health risks. In 2023, he was elected a lifetime fellow of the American Association for his achievements in the study of risk factors for age-related cognitive decline for Alzheimer's disease and other types of dementia. Dr. Andel explains how daily routines and purpose directly impact brain function and why some retirees experience faster cognitive decline than others. He shares his findings from several international studies—including his viral TED Talk, "Is Retirement Bad for Your Brain?"—and delves into why your post-retirement plan matters just as much as your financial one. In our conversation, you'll hear why those who retire from high-level managerial careers may be at greater risk for faster cognitive decline in retirement, how volunteering and pursuing new hobbies improves brain function and Dr. Andel's poignant advice for anyone who is a caretaker for a loved one that is suffering from dementia or Alzheimer's. In this podcast interview, you’ll learn: Why retirement without purpose can accelerate cognitive decline—and how to avoid the retirement trap. The connection between high-engagement careers and faster post-retirement mental decline. What research says about sleep, supplements, and cardiometabolic health for brain function. How race, gender, and job complexity influence cognitive aging differently. Why routine, exercise, and meaningful engagement are essential to brain longevity. Show Notes: RetireWithPurpose.com/504 📧 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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