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 Founder 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. ©2024 HOWARD BAILEY FINANCIAL, INC.

534: By the Numbers: Gold vs. Stocks — What the Data Says About Retirement Portfolios 11/21/2025

533: By the Numbers: The Case for “Good Enough” — Why Simplicity Often Beats Perfection in Retirement Planning 11/14/2025

532: Debunking Advice From Financial “Gurus” to Create An Efficient Retirement Income Plan with David McKnight 11/10/2025

532: Debunking Advice From Financial “Gurus” to Create An Efficient Retirement Income Plan with David McKnight Today, I’m speaking with David McKnight. David is a best-selling author, world-renowned tax strategist, and financial educator who challenges some of the most popular (and misleading) retirement gurus and influencers in the financial advice space. He’s also a great friend, and beloved guest on the show and I’m excited to welcome him back for a 3rd time on the podcast. David is well known as the author of The Power of Zero which was made into a full-length documentary film. In his latest book, The Guru Gap, he exposes why one-size-fits-all financial guidance from so-called experts often leaves retirees underprepared and overexposed to risk. We discussed the psychological appeal of “guru” advice and how to identify when those blanket statements—like “annuities are bad” or “the 4% rule always works,”—do more harm than good. One of the things that I love about David is that he shares math-based insights into retirement income planning. We’re talking about the true cost of longevity risk, and why annuities can often create more liquidity and peace of mind than traditional withdrawal strategies. David also shares his perspective on the newly extended tax cuts, how to time Roth conversions in light of the One Big Beautiful Bill, and the three critical questions everyone needs to answer before moving money from tax-deferred to tax-free accounts. Whether you’re skeptical about annuities, curious about LIRPs, or confused by conflicting advice online, this episode will help you cut through the noise and design a retirement plan that’s truly tailored to you—not to the masses. GET A FREE COPY OF DAVID MCKNIGHT’S NEW BOOK, THE GURU GAP 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 “one-size-fits-all” financial advice can be dangerous in retirement planning. The psychological reason Americans follow gurus—and how it can derail your goals. The real math behind annuities, the 4% rule, and the illusion of liquidity. How life insurance can serve as a volatility buffer and long-term care resource. The truth about Roth conversions and the importance of your “drop-dead date.” What the new One Big Beautiful Bill means for future tax rates. Why simplicity—not complexity—is the hallmark of truly successful investors. 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: /episode/index/show/retirewithpurposepodcast/id/38919805

531: By the Numbers: Why Retirees Often Spend Too Little, Too Late 11/07/2025

530: Freedom After 50: How Challenge Rekindles Purpose in Your Next Chapter 10/31/2025

529: By the Numbers — Your Financial Wake-Up Call: How to Stop Delaying the Decisions That Matter Most 10/24/2025

528: Freedom After 50: Finding Peace in the Mystery – Why Financial Control Is an Illusion 10/17/2025

528: Freedom After 50: Finding Peace in the Mystery – Why Financial Control Is an Illusion The belief that more data equals more control is an illusion. Our obsession with finding the “perfect” financial plan and receiving constant information often leads to anxiety, not peace. Join us as we explore why embracing uncertainty, focusing on what you can control, and leading with purpose can help create true financial (and emotional) freedom. In this episode, we discuss: How to balance control with surrender The pitfalls of too much information Dangers of financial fundamentalism How to go from analysis to action Today's article is from The Net Worthwhile® Weekly blog titled . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to discuss how embracing uncertainty, focusing on what you can control, and leading with purpose fosters true financial and emotional freedom. 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: /episode/index/show/retirewithpurposepodcast/id/38535700

527: Challenging the Conventional Wisdom of Stocks vs. Bonds and Common Retirement Planning Strategies with Edward McQuarrie 10/13/2025

527: Challenging the Conventional Wisdom of Stocks vs. Bonds and Common Retirement Planning Strategies with Edward McQuarrie Today, I’m speaking with Edward McQuarrie. Ed is the Professor Emeritus at Santa Clara University, where he taught in the marketing department for more than three decades before retiring in 2016. After stepping away from teaching, Ed pursued a new passion in researching financial market history and retirement income planning. His work has been featured in the Wall Street Journal, MarketWatch, and Barron’s, and he frequently contributes to our Weekend Reading for Retirees series. He was introduced to us by past guest William Bernstein, who insisted Ed would be a must-hear voice on the show. In this conversation, Ed challenges decades of conventional wisdom around investing. He explains why “stocks for the long run” isn’t always the safest bet, how cherry-picked data can mislead investors, and why separating risk-free assets from growth assets may be more important than diversification alone. Ed also shares the insights from his extensive historical research, covering stock and bond returns going back to the 1700s, and how it relates to retirement planning today. We also dig into the evolving conversation around Roth conversions, the limitations of relying solely on stocks and bonds, and why tools like TIPS ladders or annuities can help secure baseline retirement income. Ed’s clear-eyed, historically grounded perspective will challenge the assumptions you’ve been taught and help you build a more resilient, reality-based plan for the future. In this podcast interview, you’ll learn: Why “stocks always outperform bonds” is a myth—and what 200 years of history actually reveal. The risks of relying on cherry-picked data in financial planning. How economic “regimes” shape investment returns across decades and centuries. Why risk separation, not just diversification, is key to retirement planning. The pros and cons of Roth conversions—and why sometimes doing nothing may be the smartest move. How to use TIPS ladders, annuities, and other tools to secure your baseline retirement income. 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: /episode/index/show/retirewithpurposepodcast/id/38491920

526: Rethinking Social Security: Why Waiting Until 70 Isn’t Always Best 10/10/2025

525: Freedom After 50: 12 Belief Traps Keeping You from a Meaningful and Impactful Retirement 10/03/2025

525: Freedom After 50: 12 Belief Traps Keeping You from a Meaningful and Impactful Retirement Retirement is about more than finances — it’s about meaning and growth. Join us as we explore common “belief traps” that can hold you back, how to reframe your story, and expand what’s possible in the years ahead. In this episode, we discuss: How the echo chamber and certainty traps limit perspective and growth Why the comfort trap keeps you stuck — and how to break free The danger of the perfection and irrelevance traps in later life A powerful exercise to reframe your time horizon and live with greater purpose Today's article is from our own blog titled . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to uncover common belief traps, how to reframe your story, and practical ways to expand what’s possible in the next chapter of 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: /episode/index/show/retirewithpurposepodcast/id/38420260

524: A New 4-Bucket Approach to Investing Before and After Retirement 09/26/2025

524: A New 4-Bucket Approach to Investing Before and After Retirement You're told to shift from “growth” to “protection” the moment you retire and leave the workforce. But is it really that simple? Join us as we break down the false dichotomy of pre- vs. post-retirement investing, showing why your strategy should always include a mix of offense and defense. In this episode, we discuss: Your biggest risks in retirement How to leverage all your assets (stocks, bonds, pensions, Social Security, real estate, life insurance, etc. in your income strategy) Forbes writer Tim Maurer’s 4-Bucket Approach to a holistic retirement plan Today's article is from the Forbes 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: /episode/index/show/retirewithpurposepodcast/id/38321290

523: Freedom After 50: Beyond the Pyramid—Rethinking Happiness in Retirement 09/19/2025

522: The Six Pillars to Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 2 09/15/2025

522: The Six Pillars to Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 2 Living longer is one thing. Living well is another. In Part 2 of my conversation with Dr. Bobby Dubois, we unpack the final three pillars of his blueprint for longevity: mind-body harmony, heat & cold exposure, and social relationships. Dr. Bobby explains why practices like meditation, breathwork, and even walking in nature can calm the brain and lower anxiety. We also explore the science-backed benefits of sauna and cold plunging—and what’s hype versus what’s real. Finally, we uncover why social connection is the single strongest predictor of living a long, healthy, and fulfilling life. If you want practical, evidence-based ways to boost your health, not just your longevity, this episode shows you how to put it all together. In this podcast interview, you’ll learn: How meditation and breathwork improve brain and heart health. Why saunas reduce risk of heart attack and stroke. The science behind cold plunges and their impact on mood and happiness. Why social connection is the strongest predictor of longevity, even more than exercise. How to be your own “quarterback” for health and wellness instead of hiring multiple coaches and gurus. 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: /episode/index/show/retirewithpurposepodcast/id/38153140

521: 5 Timeless Proverbs for a Wise and Wealthy Retirement 09/12/2025

520: The Six Pillars of Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 1 09/08/2025

520: The Six Pillars of Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 1 Today, I’m speaking with Dr. Bobby Dubois. Dr. Bobby is a Harvard-educated physician, Board-Certified in Internal Medicine with over 25 years of experience. He’s an author, entrepreneur, wellness doctor, and Ironman Triathlete. Most recently, he led a health policy research organization in Washington, D.C. (National Pharmaceutical Council) as its Chief Science Officer and Executive Vice President. Prior to that, he served as the Chief Medical Officer of Cerner Life Sciences and co-founded Proto Care Sciences. He's the host of the Live Long and Well podcast and has made it his mission to help others cut through the noise and live longer with more energy as they age. The simple fact is, most retirees and pre-retirees want more time, energy, and independence to enjoy the life they’ve worked so hard to build. However, the reality is that longevity without good health won’t achieve the lifestyle that most retirees envisioned during their working years. In part 1 of this 2-part conversation, we delve into the life-extending benefits of aerobic exercise, the scientific advantages of consistent sleep, and the surprising role of relationships in promoting increased longevity. Dr. Bobby outlines his six pillars of health and explains how to apply them in retirement. And here’s the good news: it’s never too late to start. In its simplest form, his advice is strikingly similar to what you’d hear from a financial advisor: It’s much better to start saving and exercising young, but it’s never too late to start. If you want to live not only longer, but better, this episode provides a clear path and roadmap to get there. GET A FREE COPY OF DR. BOBBY DUBOIS’ E-BOOK, HOW TO LIVE LONG AND WELL 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 exercise is the most powerful lever for longevity. The six pillars of health that drive longevity and overall wellness. Why it’s never too late to start strength training and the surprising results from those who start later in life. The importance of a good sleep and tips to make it happen consistently. How sleep clears toxins from the brain and extends healthspan. How to diagnose the placebo effect to know when changing routines is working or not. Why social connection is just as important as diet and exercise. 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: /episode/index/show/retirewithpurposepodcast/id/38069685

519: Freedom After 50: How to Break Free from Your Old Story and Shape Wisdom That Lasts 09/05/2025

518: Beyond Investment Risk: Why Income Risk Could Change Your Retirement Plan 08/29/2025

517: Freedom After 50: The Need for Next—Finding Meaning Beyond Milestones 08/22/2025

516: Mind the Inflation Gap: Why Forecasts Fail and How to Hedge Smart 08/15/2025

516: Mind the Inflation Gap: Why Forecasts Fail and How to Hedge Smart Inflation is unpredictable—and it doesn’t care what the experts think. Join us as we explore why traditional forecasting fails, how real assets like real estate and commodities can act as powerful inflation hedges, and whether Bitcoin truly deserves its "digital gold" title. In this episode, we discuss: Consumer vs. professional inflation expectations What it means to leverage “Real Assets” as a hedge Why equities still matter The role of diversification A planning framework to help safeguard against inflation Today's article is from the CFA Institute 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: /episode/index/show/retirewithpurposepodcast/id/37767775

515: The Soul of Wealth: Bridging the Gap Between Money and Happiness with Daniel Crosby, PhD 08/11/2025

515: The Soul of Wealth: Bridging the Gap Between Money and Happiness with Daniel Crosby, PhD Today’s guest is Dr. Daniel Crosby, a leading psychologist and behavioral finance expert who helps individuals and organizations understand how our thoughts, emotions, and behaviors intersect with the markets—and ultimately, our sense of purpose. He serves as Chief Behavioral Officer at Orion Advisor Solutions and is the bestselling author of The Soul of Wealth: 50 Reflections on Money and Meaning. He’s been recognized by AARP and Monster.com as a top financial thinker and is the host of the Standard Deviations podcast. Daniel was on the podcast back in 2020, and I’m thrilled to have him back on the podcast to explore how uncertainty continues to shape investor behavior and how political biases can derail sound investment decisions. We discuss the psychological toll of financial news overload, why tuning out the noise is essential, and the critical importance of focusing on the controllable aspects of wealth-building. In our conversation, you’ll hear Daniel explain why wealth alone doesn’t lead to fulfillment—and how retirees, despite having ultimate time freedom, often struggle with depression and a lack of direction. He shares the five facets of a flourishing life and offers a fresh lens on using fear as a spotlight for opportunity. Daniel’s last appearance on the pod was fantastic, and I think this conversation is even better, so you won’t want to miss it! GET A FREE COPY OF DANIEL CROSBY’S NEW BOOK, THE SOUL OF WEALTH: 50 REFLECTIONS ON MONEY AND MEANING 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 uncertainty continues to drive market volatility—and how investors respond emotionally. How our political views can unconsciously distort our financial decisions. What to do when “too much time freedom” becomes a burden in retirement. How to identify and rewrite harmful financial scripts passed down from past generations. The five essential ingredients of a purpose-filled life after retirement. Why your relationship with money needs to evolve once you “have enough.” 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: /episode/index/show/retirewithpurposepodcast/id/37715270

514: Freedom After 50: You Planned Wisely—But Is Your Money Aligned with What Matters Most? 08/08/2025

513: The One Big Beautiful Bill Act: What It Really Means for Your Retirement Taxes 08/01/2025

512: Freedom After 50: The Sunk Cost Fallacies Sinking Your Future Vision 07/25/2025

512: Freedom After 50: The Sunk Cost Fallacies Sinking Your Future Vision Have you ever held on to something just because you’ve “put too much into it to let it go”? Many of us fall into the sunk cost fallacy trap—the quiet force that keeps us tied to the past. Whether it’s a house full of memories that no longer fits your lifestyle, a career that defined your identity for decades, or a friendship that’s no longer life-giving, this conversation will help you identify what might be holding you back—and, more importantly, how to move forward. In this episode, we discuss: How sunk costs can go far beyond money Why letting go = gaining freedom 3 strategies to overcome the sunk cost fallacy KHIs vs. KPIs Today's article is from The Critical Thinker titled . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to unpack the sunk cost fallacy and how it quietly holds retirees back. 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: /episode/index/show/retirewithpurposepodcast/id/37499705

511: Sequence Risk Meets RMDs: The Retirement Trap No One Talks About 07/18/2025

510: Managing Investment Risk When You've Already Won The Game with William Bernstein 07/14/2025

510: Managing Investment Risk When You've Already Won The Game with William Bernstein Today, I'm speaking with William Bernstein. Bill is a renowned investment advisor, author, and retired neurologist. He's the co-founder of Efficient Frontier Advisors, a leading voice in the world of personal finance, and the author of several acclaimed books, including The Four Pillars of Investing, The Investor's Manifesto, and The Intelligent Asset Allocator. With a unique background in neurology and finance, Bill brings a practical and evidence-based perspective to long-term investing, risk management, and financial behavior—especially for retirees and those nearing retirement. You'll hear why Bill believes the purpose of money isn't to buy things—it's to purchase autonomy, time, and peace of mind. In our conversation, we explore what it really means to "win the game" of investing—and why continuing to play after you've won could jeopardize your retirement security. Bill breaks down the risks investors often overlook, including deep risk versus shallow risk, the need versus capacity and tolerance framework, and why having a basic understanding of financial history is an underrated skill set. They also discuss how aging affects investment decisions, how burn rate should influence equity allocation, and why a purposeful retirement plan extends far beyond growing net worth. GET FREE ACCESS TO WILLIAM BERNSTEIN’S BOOK TITLED, THE FOUR PILLARS OF INVESTING Here's all you have to do... Step 1.) Subscribe to the podcast and leave an honest rating & review over on iTunes. Step 2.) Text the word BOOK to 866-599-4491 and we’ll make sure you get signed up for free. It’s that simple! In this podcast interview, you’ll learn: Why investors should reduce risk once they've “won the game”—and what that means in real terms. The critical differences between deep risk and shallow risk, and how to guard against both. How age and withdrawal rate should shape your stock-to-bond ratio in retirement. Why Treasury Inflation-Protected Securities (TIPS) can play a key role in risk management. The emotional traps investors fall into—and why historical financial knowledge is a great asset. What purpose in retirement really looks like—and why forging connections may be more valuable than money. 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: /episode/index/show/retirewithpurposepodcast/id/37234105

509: Freedom After 50: 7 Practices to Help You Stop Hiding and Start Growing 07/11/2025

509: Freedom After 50: 7 Practices to Help You Stop Hiding and Start Growing What if your greatest growth in retirement didn’t come from doing more—but from finally sitting with who you are? Throughout this discussion, we explore the concept of the “shadow self”—the parts of yourself that you may avoid, hide, or ignore—and how bringing light to these areas can lead to true peace and deeper connection in the second half of life. In this episode, we discuss: How unresolved emotional patterns can impact health, relationships, and joy Why it’s important to take inventory of the roles you’ve been praised for How to leverage retirement as a mirror and own where you’re out of alignment Today's article is from our very own blog post which you can find . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore how embracing your “shadow self” can lead to deeper peace 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: /episode/index/show/retirewithpurposepodcast/id/37330470

508: More Control, Less Surprise: A Real Retirement Tax Wake-Up Call 07/04/2025

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, . 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: /episode/index/show/retirewithpurposepodcast/id/37234005

507: Freedom After 50: You’re Not Looking for Advice—You’re Looking for Alignment, Part 2 06/27/2025

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 Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore how aligning advice with your core values leads to 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: /episode/index/show/retirewithpurposepodcast/id/37142080

506: The Surplus Bucket Strategy: A Way to Spend More Confidently in Retirement 06/20/2025

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, . 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: /episode/index/show/retirewithpurposepodcast/id/37064505

505: Freedom After 50: You’re Not Looking for Advice—You’re Looking for Alignment, Part 1 06/13/2025

Retire With Purpose - The Retirement Podcast

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