Retire With Purpose - The Retirement Podcast
Whether you are in retirement or have yet to make the transition, The Retire With Purpose podcast is a show designed to help you maximize your financial confidence and elevate your fulfillment in this chapter of life. Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and CEO of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you’ve always imagined and deserve. Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations. ©2026 HOWARD BAILEY FINANCIAL, INC.
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565: By the Numbers: Why 42% of Inheritances Disappear Within a Year
05/15/2026
565: By the Numbers: Why 42% of Inheritances Disappear Within a Year
What if the biggest risk to your legacy isn’t taxes, but what your heirs do with the money once it’s in their hands? Topics covered in this episode: Emotional and psychological triggers behind overspending Wealth transfer vs. wealth preservation Ways to give heirs a “second chance” with smarter distributions The role of trusts, trustees, and incentive-based planning Why communication with heirs is essential to a lasting legacy Today's article is from ThinkAdvisor blog titled . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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564: Signal vs. Noise: How to Make Smarter Retirement Planning Decisions with Jesse Cramer
05/11/2026
564: Signal vs. Noise: How to Make Smarter Retirement Planning Decisions with Jesse Cramer
Today, I’m very excited to welcome Jesse Cramer to the podcast. Jesse is the founder of The Best Interest blog and host of the Personal Finance for Long-Term Investors podcast, where he helps individuals cut through the noise of financial media and focus on what truly matters. In a world filled with headlines, predictions, and never-ending market chatter, Jesse brings a refreshing perspective for understanding what’s actually important for your retirement plan. Jesse began his career as an aerospace engineer before transitioning into personal finance, combining analytical thinking with clear communication. His work has been featured in outlets such as CNBC and The Wall Street Journal, and his writing has gained a strong following for its ability to simplify complex financial topics, including investing, tax planning, and retirement strategy. We’ve featured Jesse’s work many times over the years in our Weekend Reading series, and for good reason. In our conversation, we explore the concept of “signal vs. noise” and how it applies to retirement planning. Jesse explains why so much of what we hear in the media is designed to grab attention rather than provide value, and how retirees can filter through that noise to focus on what actually impacts their long-term success. In this podcast interview, you’ll learn: How to distinguish between financial “signal” and “noise” in today’s media landscape. Why confidence in retirement comes from adaptability, not perfect predictions. How sequence of returns risk impacts your retirement more than average returns. Why tax planning requires looking at your entire retirement timeline, not just the next year. The concept of “before and after” tax phases and how they shape your strategy. How different withdrawal strategies work and why there’s no one-size-fits-all solution. Why understanding your own biases is critical to making better financial decisions. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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563: Freedom After 50: From Bucket List to Life Strategy with Jet Vertz
05/08/2026
563: Freedom After 50: From Bucket List to Life Strategy with Jet Vertz
What if the goal of your bucket list isn’t to slowly check it off, but to finish it, rebuild it, and use it to fuel a more meaningful retirement? Topics covered in this episode: How to build a purpose-driven bucket list that actually gets completed Why most bucket lists are too “self-focused” and how to fix that The power of small, achievable goals Why sharing your goals increases follow through The surprising reason retirees come back to create bigger bucket lists Listen in as Founder and CEO of , Casey Weade is joined by Jet Vertz to rethink the bucket list to explain how completing, rebuilding, and sharing it can fuel a more meaningful retirement. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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562: By the Numbers: Why Your Tax Refund Isn’t What You Think
05/01/2026
562: By the Numbers: Why Your Tax Refund Isn’t What You Think
Are you actually better off getting a tax refund, or is your brain tricking you into celebrating a financial loss? Topics covered in this episode: Tax refunds vs. tax liability: what actually matters Behavioral biases (framing, loss aversion, anchoring, etc.) Strategic tax planning vs. emotional decision-making Real-world examples from retirees and working families How to align tax strategy with long-term financial goals Today's article is from Best Interest blog titled . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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561: Freedom After 50: The 80% Rule That Could Change Your Retirement Timeline with Jordan Grumet, MD
04/24/2026
561: Freedom After 50: The 80% Rule That Could Change Your Retirement Timeline with Jordan Grumet, MD
What if waiting until you’re “fully ready” for retirement is actually costing you some of the best years of your life? Topics covered in this episode: The controversial “retire at 80%” framework Why most retirees don’t run out of money The reality behind retirement spending patterns The emotional and psychological barriers to retiring Why time may be more valuable than financial certainty How to determine if you’re closer to retirement than you think Today's article is from The Purpose Code blog titled, . Listen in as Founder and CEO of , Casey Weade is joined by Jordan Grumet to explore the “retire at 80%” framework and why time may matter more than perfect financial certainty. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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560: By the Numbers: Can You Really Beat the Market by Avoiding the Worst Days?
04/17/2026
560: By the Numbers: Can You Really Beat the Market by Avoiding the Worst Days?
What if trying to avoid the market’s worst days is actually one of the fastest ways to sabotage your retirement plan? Topics covered in this episode: Why best and worst market days often occur back-to-back The math of gains vs. losses — and why it’s not equal The “lost decade” and what it teaches investors Why avoiding bad years matters more than avoiding bad days How reduced volatility strategies can stabilize retirement outcomes Today's article is from Morningstar titled . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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559: How Dopamine Shapes Your Motivation, Happiness, and Purpose in Retirement with Michael Long
04/13/2026
559: How Dopamine Shapes Your Motivation, Happiness, and Purpose in Retirement with Michael Long
Today, I’m excited to welcome Michael Long to the podcast. Michael is a physicist-turned-writer and the co-author of the international bestseller The Molecule of More. His work explores one of the most powerful forces shaping our lives: the brain chemical dopamine — and how it influences motivation, ambition, and our constant drive for “more.” Michael is also the author of Taming the Molecule of More: A Step-by-Step Guide to Making Dopamine Work for You. Over the course of his career, he has written speeches for members of Congress, presidential candidates, Fortune 10 CEOs, while also teaching at Georgetown University and producing award-winning screenplays. In our conversation, Michael explains why dopamine isn’t actually the chemical that makes us happy, it’s the chemical that makes us want more. More trips, more gadgets, more fun stuff on our phones. We discuss how this pursuit of “more” drives innovation and progress, but can also leave retirees feeling restless or unfulfilled if they’re not careful. Michael also shares practical ways to recognize when dopamine is driving your decisions, how to create healthier habits that restore balance, and why learning to live more fully in the present moment can transform your experience of retirement. GET A FREE COPY OF MICHAEL’S BOOK, TAMING THE MOLECULE OF MORE Here’s how: Step 1: Subscribe to the podcast and leave an honest rating & review on iTunes. Step 2: Text the word BOOK to 888-599-4491, and we’ll send you a link to claim your free copy! In this podcast interview, you’ll learn: Why dopamine isn’t the “happiness chemical” — it’s the chemical that drives our desire for more. How dopamine helped humans survive in a world of scarcity and danger. Why modern technology and social media can hijack your dopamine system. How retirees can redirect dopamine toward curiosity, purpose, and meaningful goals. The difference between dopamine (future-focused) and “here-and-now” brain chemicals. Simple habits that help reduce impulsive dopamine-driven decisions. Why learning to pause and appreciate the present moment can dramatically improve life satisfaction in retirement. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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558: By the Numbers: The Bucket Strategy vs. 60-40 - Who Really Wins?
04/10/2026
558: By the Numbers: The Bucket Strategy vs. 60-40 - Who Really Wins?
What if the strategy you trust most for retirement income is quietly costing you hundreds of thousands of dollars? Topics covered in this episode: The real driver behind outperformance Sequence of returns risk and the “retirement risk zone” Why rebalancing can help (or hurt) your long-term results The surprising case for increasing equity exposure over time Limitations of bonds in modern retirement portfolios How small tweaks can potentially add six figures to your retirement Today's article is from The Retirement Manifesto titled . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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557: By the Numbers: The Fragile Decade That Could Make (or Break) Your Retirement
04/03/2026
557: By the Numbers: The Fragile Decade That Could Make (or Break) Your Retirement
What if the real retirement risk zone isn’t during retirement… but the five critical years before and after it begins? In this episode, you’ll learn about: Pre- vs. post-retirement sequence of returns risk How to stress test your retirement plan effectively The role of asset allocation shifts in late-stage accumulation Why target date funds may carry more risk than expected How to build income certainty and protection strategies The psychology of transitioning from growth to preservation Today's article is from ThinkAdvisor.com titled . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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556: By the Numbers: Could the Government Tax Your Roth IRA in the Future? What if Congress Changes the Rules?
03/27/2026
556: By the Numbers: Could the Government Tax Your Roth IRA in the Future? What if Congress Changes the Rules?
If you convert to a Roth today, could Congress change the rules tomorrow — and should that fear stop you from taking action? In this episode, you’ll learn: The truth about retroactive Roth taxation Why traditional IRA risk may be greater than Roth risk How RMDs can quietly create massive tax exposure What recent legislation signals about the future of Roth accounts Why tax diversification — not fear — should guide your strategy How to determine if a Roth conversion makes sense for your numbers Today's article is titled Could the Government Tax Your Roth IRA in the Future? Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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555: By the Numbers: The Anchors of Retirement Confidence, Part 4 — Building a Retirement That Can’t Break
03/20/2026
555: By the Numbers: The Anchors of Retirement Confidence, Part 4 — Building a Retirement That Can’t Break
Join us as we continue our “Anchors of Retirement Confidence” series, where we discuss four areas of retirement uncertainty plus strategies designed to replace your anxiety with clarity and control. In part 4, we explore the protection anchors — and how preparing for worst-case scenarios can help you feel more confident through market volatility. In this episode, you’ll learn about: Why guaranteed income floors can help improve spending confidence How to manage long-term care as a catastrophic risk How to compare income strategies and trade-offs The power of using home equity as a last-resort safety net How stacking protection anchors removes fear and uncertainty Today's article is from Morningstar titled, . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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554: Freedom After 50: Why Retirement Fear Might Be a Sign You’re Ready
03/13/2026
554: Freedom After 50: Why Retirement Fear Might Be a Sign You’re Ready
What if the fear you feel about retirement isn’t a warning sign, but an invitation to step into a more meaningful, self-directed life? In this episode, you’ll learn: Why hitting your retirement number can increase anxiety The difference between financial independence and fulfillment Three powerful questions to clarify whether it’s time to retire How purpose evolves after work — and why fear often shows up first Today's article is from The Purpose Code blog titled, . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore why hitting your number can increase anxiety, how financial independence differs from fulfillment, and the key questions that clarify when it’s truly time to retire. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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553: A Step-by-Step Guide to Leverage AI As a Thought Partner & Find Purpose In Retirement with Geoff Woods
03/09/2026
553: A Step-by-Step Guide to Leverage AI As a Thought Partner & Find Purpose In Retirement with Geoff Woods
Today, I’m thrilled to finally welcome my friend, Geoff Woods, to the podcast. Geoff is the founder of AI Leadership and The AI-Driven Leadership Collective, the author of The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions, and a leading expert on AI. He previously served as Chief Growth Officer of Jindal Steel & Power, where he played a key role in scaling the company from a $750 million market cap to over $12 billion in just four years. He also co-founded the company behind , advising organizations with revenue ranging from $10 million to $60 billion. In our conversation, Geoff doesn’t just explain what AI does in theory—he’ll walk you through a live demonstration of how to use it as a thought partner to help navigate the transition into retirement with greater clarity, confidence, and a renewed sense of purpose. Geoff introduces his CRIT framework for prompting AI more effectively and shares practical strategies for using AI to identify purpose, strengthen daily habits, and avoid common pitfalls. Geoff also shares his insights on how AI is rapidly shaping the world we live in, addresses concerns about job disruption for the next generation, and explains why learning to use it now will give you an advantage over those who choose to live in fear of it. GET A FREE COPY OF GEOFF’S BOOK, THE AI-DRIVEN LEADER: HARNESSING AI TO MAKE FASTER, SMARTER DECISIONS Here’s how: Step 1: Subscribe to the podcast and leave an honest rating & review on iTunes. Step 2: Text the word BOOK to 888-599-4491, and we’ll send you a link to claim your free copy! In this podcast interview, you’ll learn: A simple explanation of AI and how it differs from machine learning and generative AI. Why AI will impact retirees even if it wasn’t specifically designed for them. How AI can support better daily decisions around health, habits, and planning. The simplest way to manage privacy settings and reduce concerns about personal data with ChatGPT. Why AI should be treated as a thought partner, not a replacement for your thinking. How the CRIT framework helps generate deeper, more customized responses. Three strategies for transitioning into retirement with more structure and purpose. Why technological change shifts skill value rather than simply eliminating opportunity. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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552: By the Numbers: The Anchors of Retirement Confidence, Part 3 — Why Tax Flexibility Matters More Than Tax Savings
03/06/2026
552: By the Numbers: The Anchors of Retirement Confidence, Part 3 — Why Tax Flexibility Matters More Than Tax Savings
Join us as we continue our “Anchors of Retirement Confidence” series, where we discuss four areas of retirement uncertainty plus strategies to replace your anxiety with clarity and control. In part 3, we explore why the biggest threat to your retirement isn’t always market volatility, but the taxes you didn’t see coming until it was too late. In this episode, you’ll learn: How tax concentration quietly limits income flexibility The three core tax buckets every retiree should understand How Roth accounts help create control in an unpredictable tax system Real-life case studies showing why “textbook” strategies don’t always work Today's article is from Morningstar titled, . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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551: Freedom After 50: Why Retirement Decisions Feel Heavier — and What to Do About It
02/27/2026
551: Freedom After 50: Why Retirement Decisions Feel Heavier — and What to Do About It
What if the confidence you’re searching for in retirement decisions hasn’t disappeared, but has simply been drowned out by noise? In this episode, you’ll learn: Why retirement decisions feel more emotionally loaded after 50 The difference between useful information and paralyzing overwhelm How anxiety can be a guide; not a warning sign How to rebuild trust in your intuition and inner voice Today's article is from our own blog titled, . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore how retirees can cut through the noise, manage emotional overwhelm, and rebuild confidence in decisions by trusting their intuition and inner voice. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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550: By the Numbers: The Anchors of Retirement Confidence, Part 2 — Building a Plan for the Next Market Crash
02/20/2026
550: By the Numbers: The Anchors of Retirement Confidence, Part 2 — Building a Plan for the Next Market Crash
Join us as we continue our “Anchors of Retirement Confidence” series, where we discuss four areas of retirement uncertainty plus strategies to replace your anxiety with clarity and control. In part 2, we explore what really puts retirements at risk during market downturns — and how to build a plan that’s designed to withstand them. In this episode, you’ll learn: Why market volatility isn’t the real danger in retirement How a recession buffer creates emotional and financial stability How to separate “living money” from “growth money” Why using time-based buckets can help you gain confidence and clarity Today's article is from Morningstar titled, . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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549: Freedom After 50: The Hidden Link Between Your Money Habits and Your Life
02/13/2026
549: Freedom After 50: The Hidden Link Between Your Money Habits and Your Life
Are your investment habits quietly shaping the way you live — and could a few mindset shifts help you build a more patient, resilient, and fulfilling retirement? In this episode, you'll learn: How investing principles translate into life decisions Using stress and uncertainty as tools instead of threats Why margin of safety matters beyond your portfolio The difference between being rich and being truly wealthy What it really takes to prepare for the life side of retirement Today's article is from Vishal Khandelwal's Substack titled, . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore how investing habits shape life beyond money—and how mindset shifts can build patience, resilience, and fulfillment in retirement. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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548: Conscious Aging: Finding Meaning, Purpose, and Growth in Retirement with Ron Pevny
02/09/2026
548: Conscious Aging: Finding Meaning, Purpose, and Growth in Retirement with Ron Pevny
Today, I’m thrilled to welcome Ron Pevny to the podcast. Ron is the founder and director of the Center for Conscious Eldering, a certified Sage-ing Leader with Sage-ing International, and a longtime guide for individuals navigating life’s most meaningful transitions. With a master’s degree in integral counseling and psychotherapy, Ron has spent decades helping people move through major life passages with intention, clarity, and depth. Ron is also the author of Conscious Living, Conscious Aging: Claiming the Gifts of Elderhood, a powerful guide for those entering the later chapters of life and seeking more than just rest or recreation. His work reframes aging not as decline, but as an opportunity to step into elderhood with purpose—drawing on wisdom, lived experience, and a renewed commitment to growth and contribution. In our conversation, we explore what it truly means to become an elder in today’s world. Ron shares the catalysts that led him into this work, including profound health challenges that reshaped his perspective on purpose and calling. We also discussed the three-phase transition into elderhood and why honoring each stage is essential for discovering what’s next after retirement. GET A FREE COPY OF RON PEVNY’S BOOK, CONSCIOUS LIVING, CONSCIOUS AGING: CLAIMING THE GIFTS OF ELDERHOOD Here’s how: Step 1: Subscribe to the podcast and leave an honest rating & review on iTunes. Step 2: Text the word BOOK to 888-599-4491, and we’ll send you a link to claim your free copy! In this podcast interview, you’ll learn: What “conscious eldering” really means—and why it matters. Why retirement without purpose often leads to feeling stuck or disengaged. The three phases of transitioning into elderhood. How the neutral zone creates space for clarity and renewal. Why denying aging limits growth and fulfillment. How to identify and express your signature gifts. The role elders play in supporting future generations. Why purpose helps offset physical and emotional challenges later in life. How growth and service remain essential at every age. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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547: By the Numbers: The Anchors of Retirement Confidence, Part 1 — Finding Your Sustainable Spending Range
02/06/2026
547: By the Numbers: The Anchors of Retirement Confidence, Part 1 — Finding Your Sustainable Spending Range
Join us for our “Anchors of Retirement Confidence” series, where we discuss four areas of retirement uncertainty plus strategies to replace your anxiety with clarity and control. In part 1, we tackle how to create a flexible spending system that adapts with you. In this episode, you’ll learn: Why safe withdrawal “rules” can create unnecessary stress How to find your personal sustainable spending range The power of small spending adjustments Why most retirees naturally spend less as they age How flexibility becomes your strongest retirement asset Today's article is from Morningstar titled, . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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546: Freedom After 50: How to Stay Grounded When the Future Feels Unknown
01/30/2026
546: Freedom After 50: How to Stay Grounded When the Future Feels Unknown
What if the key to a calmer, more meaningful retirement isn’t having all the answers, but learning how to trust yourself when you don’t? In this episode, we discuss: Why retirement feels more uncertain than working life How identity shifts after 50 can create anxiety What’s true vs. what’s just loud How to focus on what you can control — in life and money A 4-step practice to calm fear and regain clarity Today's article is from our very own blog titled, . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore why retirement can feel more uncertain than working life. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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545: By the Numbers: Our 2026 Market Predictions
01/23/2026
545: By the Numbers: Our 2026 Market Predictions
Will 2026 deliver another strong bull-market year — or a long-overdue reality check as AI, market valuations, and global shifts collide? In this episode, we discuss: 2026 S&P 500 predictions (15.2% vs. 6.7%) AI’s explosive growth The Magnificent Seven’s shrinking dominance Why equal-weighted investing reduces volatility Why bonds, gold, and diversification matter again How pre-retirees can protect gains while staying invested Today's article is from Kitces.com titled, . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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544: Freedom After 50: Are You Living for Your Resume—or Your Eulogy?
01/16/2026
544: Freedom After 50: Are You Living for Your Resume—or Your Eulogy?
What if the real measure of a successful retirement isn’t what you’ve built, but who you’ve been, and how your money supports the life you want to be remembered for? In this episode, we discuss: Resume virtues vs. eulogy virtues Why many retirees feel “lost” after achieving everything they worked for How purpose changes the way you think about money, work, and time Using financial planning to create freedom, not pressure Redefining identity, success, and legacy after 50 Today's article is from The Root of All titled, . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore how redefining success through purpose, legacy, and “eulogy virtues” can transform retirement. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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543: The Stress Paradox: Why the Right Kind of Stress Helps You Thrive in Retirement with Dr. Sharon Bergquist, MD
01/12/2026
543: The Stress Paradox: Why the Right Kind of Stress Helps You Thrive in Retirement with Dr. Sharon Bergquist, MD
Today, I’m excited to welcome Dr. Sharon Bergquist to the podcast. Sharon is a board-certified physician, research scientist, founder of Emory Lifestyle Medicine & Wellness, and an internationally recognized leader in lifestyle medicine. She has led or co-led over a dozen clinical trials that have received $61 million in funding to evaluate lifestyle interventions and identify early biomarkers for chronic disease, including ongoing studies for early detection of Alzheimer’s disease and cancer. Her work is at the forefront of how we understand the role of stress and resilience on our health and longevity. As the author of The Stress Paradox: Why You Need Stress to Live Longer, Healthier, and Happier, Dr. Bergquist brings a deeply personal and scientific perspective to the conversation. She shares how early-life adversity shaped her understanding of resilience and how decades of clinical research led her to challenge the conventional narrative about stress. Sharon explains why not all stress is harmful, how the body is biologically designed for growth through challenge, and why eliminating stress may actually harm long-term health and longevity. In our conversation, we explore the science behind how good stress in the “Goldilocks Zone” can strengthen the body and mind. Sharon outlines how purposeful stress supports mitochondrial health, cognitive function, physical capacity, and emotional well-being, and explains why recovery is just as essential as the challenges we create and overcome. GET A FREE COPY OF DR. SHARON BERGQUIST’S NEW BOOK, THE STRESS PARADOX: WHY YOU NEED STRESS TO LIVE LONGER, HEALTHIER, AND HAPPIER Here’s how: Step 1: Subscribe to the podcast and leave an honest rating & review on iTunes. Step 2: Text the word BOOK to 888-599-4491, and we’ll send you a link to claim your free copy! In this podcast interview, you’ll learn: Why not all stress is harmful—and how the right stress promotes longevity. The difference between distress, eustress, and not enough stress. How meaning and purpose challenges us and strengthens resilience. Why avoiding stress in retirement can backfire physically and mentally. The role mitochondria play in our energy, aging, and stress levels. The importance of recovery and how it transforms stress into growth. Why purpose is actually beneficial in protecting us against aging. How to rethink retirement as a season of continued growth and contribution. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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542: By the Numbers: From Fear to Freedom — Learning How to Spend in Retirement
01/09/2026
542: By the Numbers: From Fear to Freedom — Learning How to Spend in Retirement
You saved diligently for decades — so why does giving yourself permission to spend still feel so hard? In this episode, we discuss: Why many retirees underspend despite having a secure financial plan Emotional and psychological barriers to spending How lifelong, “saver” habits impact retirement decisions Low-risk strategies to help build spending confidence Today's article is from the Kitces blog titled, Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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541: Your 2026 Reset: The Best of the Retire With Purpose Podcast
01/02/2026
541: Your 2026 Reset: The Best of the Retire With Purpose Podcast
What can our top five Retire With Purpose Podcast episodes of 2025 teach you about avoiding regrets, spending confidently, and living with purpose as you head into 2026? In this episode, we discuss: The most common retirement regrets How to generate flexible, reliable income in retirement The Surplus Bucket Strategy and why it can help spending confidence How to understand your level of retirement readiness Why delaying joy can come at a higher cost than you think Listen in as Founder and CEO of , Casey Weade kicks off the new year with a "Best Of" episode to reflect on the best moments from 2025 by revisiting the insights that resonated the most with you, the listener, this past year. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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540: Freedom After 50: The Quiet Fear Beneath Retirement (and How to Outsmart It)
12/26/2025
540: Freedom After 50: The Quiet Fear Beneath Retirement (and How to Outsmart It)
If retirement is supposed to bring freedom, why do so many people still feel unsettled, and what’s behind that tension? In this episode, we discuss: Why fear persists even with a strong financial plan Dangers of letting the news cycle shape your outlook Why retirees often search for a “true sage” — and why that search fails The “Yada” reflective framework and techniques for cultivating presence, peace, and self-awareness Today's article is from our very own blog titled, . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore how news-driven anxiety, the search for certainty, and misplaced trust impact peace, and discover the Yada framework for cultivating presence and self-awareness. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions
12/19/2025
539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions
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, Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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538: Freedom After 50: Why Enough Is a Mindset, Not a Number
12/12/2025
538: Freedom After 50: Why Enough Is a Mindset, Not a Number
What if the biggest obstacle to a joyful retirement isn’t your money — but the belief that you never have enough of it? In this episode, we discuss: Why “having enough” is both a financial and emotional question When saving “too well” creates new problems The FIRE movement cautionary tale The role of curiosity, creativity, and craft in a purposeful retirement Today's article is from The Root of All titled, . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore the emotional side of financial security, the pitfalls of oversaving, and how curiosity, creativity, and craft can lead to a more purposeful next chapter. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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537: The Most Overlooked Elements of a Successful Retirement with Fritz Gilbert
12/08/2025
537: The Most Overlooked Elements of a Successful Retirement with Fritz Gilbert
Today, I’m thrilled to welcome Fritz Gilbert back for his second appearance on the podcast. Fritz is an award-winning blogger and author of The Retirement Manifesto, one of the most influential retirement blogs in the country. He has now been retired for six years, and while many people think the big transition ends the day you leave the workforce, Fritz’s journey proves that retirement continues to evolve in meaningful, surprising, and deeply personal ways. Recently, he announced he is stepping away from full-time blogging to spend more of his life “outside the walls,” shifting his time toward family, exercise, charitable work, and the flexibility that first drew him to retirement. Fritz explains why stepping back wasn’t a loss—it was a necessary reshuffling of cards in the ongoing “game of retirement poker.” In our conversation, Fritz discusses the surprising emotional journey of redefining retirement. He explains why he has never struggled with boredom, depression, or identity loss, and highlights how he avoided the most difficult retirement phase that nearly 70% face. We also talk about one of the most overlooked elements of retirement satisfaction: giving yourself permission to spend your money—or gift to your kids—while you can enjoy the benefits, rather than clinging to your savings out of habit or fear. Fritz explains why intentional spending is not only rational but also often essential for living a fully realized, purposeful retirement. In this podcast interview, you’ll learn: How Fritz avoided boredom, identity loss, and the infamous “retirement dip.” The surprising emotional transition his wife experienced after caregiving. Why replacing the non-financial benefits of work is a must. How to refine a bucket strategy and reduce interest-rate risk in retirement. The real challenge of Roth conversions and why liquidity matters. Why many retirees spend too little and how Fritz overcame that fear. How to support adult children without jeopardizing their independence. Why the 90/10 rule becomes unavoidable in retirement. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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536: By the Numbers: Cash Out or Hold On? The Retiree’s Dilemma
12/05/2025
536: By the Numbers: Cash Out or Hold On? The Retiree’s Dilemma
With talk of bubbles, corrections, and overvaluation dominating the headlines, we unpack how you can stay confident, stay invested, and stay sane when markets feel anything but predictable. In this episode, we discuss: Reasons why you might reduce stock exposure Poor (or dangerous) reasons to move to cash The biggest threat to your portfolio Practical investment frameworks to leverage in today’s economic climate Today's article is from the Best Interest blog titled, Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: 📅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: 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:
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