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.

580: Die With Zero: Rethinking Wealth, Retirement, and Fulfillment with Bill Perkins 08/10/2026

580: Die With Zero: Rethinking Wealth, Retirement, and Fulfillment with Bill Perkins Today, I'm excited to welcome Bill Perkins to the podcast. Bill is an entrepreneur, hedge fund manager, investor, and bestselling author of Die With Zero: Getting All You Can from Your Money and Your Life. Throughout his career, he's challenged one of the most common assumptions about wealth: that accumulating more money should always be the ultimate goal. Instead, Bill encourages people to think differently about how they use their time, health, and financial resources to create a more fulfilling life. Far too many retirees spend decades building wealth only to discover that saving money is much easier than confidently spending it. Bill believes retirement isn't about maximizing your account balance; it's about maximizing your experiences while you still have the health and time to enjoy them. That means being intentional about when you travel, when you create memories with loved ones, and even when you pass wealth on to the next generation. In our conversation, Bill explains why money should always serve your life instead of becoming the goal itself, how "time bucketing" can help prioritize life's most meaningful experiences, why health may be your most valuable retirement asset, and how intentionally spending, giving, and creating memories can ultimately lead to a richer and more purposeful retirement. GET A FREE COPY OF BILL’S BOOK, DIE WITH ZERO: GETTING ALL YOU CAN FROM YOUR MONEY AND YOUR LIFE Here’s how: Just 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 maximizing fulfillment—not maximizing wealth—should become your retirement goal. How time bucketing helps you prioritize experiences before opportunities disappear. Why your health becomes one of your most valuable retirement resources. How memory dividends can create lasting returns long after an experience ends. Why intentionally giving wealth during your lifetime may create a greater legacy than leaving an inheritance after you're gone. How designing simple systems can help you live more intentionally instead of on autopilot. 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/42310160

579: Will Social Security Really Run Out? What Retirees Need to Know 08/07/2026

579: Will Social Security Really Run Out? What Retirees Need to Know Headlines say Social Security is going bankrupt, but the real story is far more nuanced, and understanding it could help you make smarter retirement decisions before it's too late. In this episode, you’ll learn: What the latest 2026 Trustee Report reveals Why retirees could still receive benefits, even without Congressional action How AI, longevity, and future productivity could change the outlook The most likely solutions Congress could pursue How to stress test your retirement income plan for multiple Social Security scenarios Today's article is from the Center for Retirement Research at Boston College 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 /episode/index/show/retirewithpurposepodcast/id/42297055

578: The Fear of Running Out vs. The Fear of Missing Out 07/31/2026

577: Long-Term Investing: What Many Retirees Get Wrong 07/24/2026

576: The Retirement Exercise That Changes Everything 07/17/2026

576: The Retirement Exercise That Changes Everything What if one simple exercise could help you uncover what truly brings you joy, clarify your purpose, and shape a more meaningful retirement? As part of our “Freedom After 50” series, author Jet Vertz shares: How the "Lifeline Exercise" helps uncover defining moments in your life Why your happiest moments often reveal your deepest values How to identify the strengths, passions, and experiences that should shape your retirement Why honesty with yourself is essential to creating a retirement filled with meaning instead of simply staying busy A simple reflection exercise you can do on your own, or even with your spouse Listen in as Founder and CEO of , Casey Weade and Jet Vertz provide 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/42052010

575: Why Your Health Is Your Greatest Retirement Asset with Dr. Phil Pearlman 07/13/2026

575: Why Your Health Is Your Greatest Retirement Asset with Dr. Phil Pearlman Today, I'm excited to welcome Dr. Phil Pearlman to the podcast. Phil is the founder of the Pearl Institute, a clinical psychologist, former financial executive, and one of the leading voices exploring the intersection of health, behavioral psychology, and long-term performance. Through his writing, coaching, and research, he helps people build healthier lives by focusing on sustainable habits, emotional resilience, and purposeful daily decisions. After years of success in finance, Phil experienced his own health transformation that completely changed how he thinks about performance, longevity, and fulfillment. Today, he believes one of the biggest blind spots in retirement planning isn't your portfolio, it's your health. Because no matter how well you've prepared financially, it's difficult to enjoy the retirement you've worked so hard to build without the physical and mental capacity to fully experience it. In our conversation, Phil shares why health and wealth follow many of the same behavioral principles, how our relationship with food and money is driven by the same psychological forces, and why improving your health may be the greatest investment you can make in your future. In this podcast interview, you’ll learn: Why your health may be the most overlooked risk to a successful retirement. How our relationship with food and money is shaped by the same psychological biases. Why lasting health habits are built through identity, not willpower. How improving your metabolic health can lead to better decisions, focus, and resilience. Why comparing yourself to your past self and nobody else creates the greatest long-term progress. The simple daily habits Phil believes deliver the biggest return for your future health. 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/42003575

574: Why Most Stocks Fail (And What Retirees Need to Know) 07/10/2026

573: The Life Transition Every Retiree Must Learn to Master 07/03/2026

573: The Life Transition Every Retiree Must Learn to Master Retirement isn't just about leaving your career; it's about learning how to navigate one of life's biggest transitions with confidence and resilience. As part of our “Freedom After 50” series, best-selling author Bruce Feiler shares why the most fulfilling retirements come from embracing change instead of resisting it. Topics covered in this episode: Why retirement is often a "lifequake," not just a life event The three phases everyone experiences during major life transitions How to avoid getting stuck after retirement How couples can navigate retirement transitions together A simple exercise to identify where you are and what you need most Listen in as Founder and CEO of , Casey Weade and Bruce Feiler provide 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/41945560

572: Is AI Carrying the Entire Stock Market? 06/26/2026

571: You've Saved for Retirement — So Why Does Spending Still Feel Wrong? 06/19/2026

571: You've Saved for Retirement — So Why Does Spending Still Feel Wrong? You’ve accrued wealth to finally retire, but your “best” retirement involves learning how to enjoy the life your wealth was meant to support. As part of our “Freedom After 50” series, hospice doctor Jordan Grumet explores how to discover what truly brings you fulfillment once money is no longer the main objective. Topics covered in this episode: The emotional transition from accumulation to retirement Why reaching financial independence doesn't automatically create peace of mind The 3 phases of spending and how expectations often clash with reality Ways to spend with confidence while staying aligned with your values Today's article is from the The Purpose Code 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/41685810

570: Is Your Social Security Really Worth $1 Million? 06/12/2026

570: Is Your Social Security Really Worth $1 Million? What if your Social Security benefit is worth far more than you realize, and the decision of when to claim it could be one of the biggest financial choices you’ll ever make? As part of our “By the Numbers” series, topics covered in this episode include: Why Social Security should be viewed as an asset, not just monthly income How claiming at 62 vs. 67 vs. 70 impacts lifetime value The role inflation, taxes, and longevity play in your decision Common misconceptions about Social Security “running out” Practical steps to begin analyzing your own benefits today Today's article is from the Mr. Money Mustache 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/41518450

569: Rethinking the 4% Rule for Today's Retirees with Bill Bengen 06/08/2026

569: Rethinking the 4% Rule for Today's Retirees with Bill Bengen Today, I'm honored to welcome Bill Bengen to the podcast. Bill is widely known as the father of the 4% Rule and as one of the most influential retirement-income researchers in history. His groundbreaking research transformed the way financial advisors and retirees think about generating sustainable income in retirement, and his work continues to shape retirement planning decades after its initial publication. Over the past 30 years, Bill has studied hundreds of historical retirement scenarios to better understand how retirees can spend confidently without the fear of running out of money. In his latest book, A Richer Retirement: Supercharging the 4% Rule to Spend More and Enjoy More, he challenges many assumptions people have about retirement spending and financial security. In our conversation, Bill addresses one of the biggest misconceptions about the 4% Rule, which was never intended to be a spending target for everyone, why inflation remains the greatest threat to retirement income, and how market valuations impact sustainable withdrawal rates. Bill also shares his views on diversification, annuities, retirement spending, and the common reasons retirees continue to underspend despite having more than enough. GET A FREE COPY OF BILL’S BOOK, A RICHER RETIREMENT: SUPERCHARGING THE 4% RULE TO SPEND MORE AND ENJOY 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 the original 4% Rule was designed around the worst retirement scenario in modern history. How Bill's research evolved from a 4% withdrawal rate to 4.7% through broader diversification. Why inflation remains the single greatest threat to a retiree's long-term success. How market valuations influence sustainable withdrawal rates and retirement income planning. Why many retirees could safely spend more than they currently believe. Why planning horizons should extend well beyond your projected life expectancy. 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/41518115

568: The 4 Emotional Phases of Retirement with Fritz Gilbert 06/05/2026

568: The 4 Emotional Phases of Retirement with Fritz Gilbert What happens when the retirement you worked so hard for doesn’t feel as fulfilling as you imagined, and how can you rediscover purpose, structure, and joy in this next chapter of life? As part of our “Freedom After 50” series, topics covered in this episode include: Why the “honeymoon phase” of retirement eventually fades Why curiosity may be the single most important retirement skill Practical ways to experiment, reinvent yourself, and find purpose again How retirees can avoid getting stuck in the “lost and loss” phase Why retirement planning should include far more than finances 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: /episode/index/show/retirewithpurposepodcast/id/41503550

567: Hidden Estate Planning Risks Retirees Overlook 05/29/2026

567: Hidden Estate Planning Risks Retirees Overlook Could one outdated beneficiary form, missing trust provision, or overlooked document completely derail the legacy you intended to leave behind? Topics covered in this episode: The biggest misconceptions retirees have about wills vs. trusts Why beneficiary designations can override your will The real purpose of a revocable living trust, and what it does NOT do Why estate planning failures often come down to poor account titling and coordination How trusts can protect children, spouses, and inherited assets from divorce, lawsuits, or poor financial decisions 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: /episode/index/show/retirewithpurposepodcast/id/41419900

566: Freedom After 50: How to Avoid Retirement Shock and Find Purpose Again with Mike Drak 05/22/2026

566: Freedom After 50: How to Avoid Retirement Shock and Find Purpose Again with Mike Drak Retirement isn’t always the carefree finish line people imagine. For many, it marks the start of a deeper search for purpose, identity, and fulfillment. Topics covered in this episode: Why so many retirees experience “retirement shock” after leaving work How loss of structure and purpose can impact happiness and mental health The growing importance of part-time work, passion projects, and volunteering Author Mike Drak’s “late bloomer” philosophy for creating a second act How the Ikigai Method can help retirees uncover meaningful work and purpose Listen in as Founder and CEO of , Casey Weade is joined by Mike Drak to explore why retirement can trigger a deeper search for purpose, identity, and fulfillment. 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/41356680

565: By the Numbers: Why 42% of Inheritances Disappear Within a Year 05/15/2026

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: /episode/index/show/retirewithpurposepodcast/id/41199900

563: Freedom After 50: From Bucket List to Life Strategy with Jet Vertz 05/08/2026

562: By the Numbers: Why Your Tax Refund Isn’t What You Think 05/01/2026

561: Freedom After 50: The 80% Rule That Could Change Your Retirement Timeline with Jordan Grumet, MD 04/24/2026

560: By the Numbers: Can You Really Beat the Market by Avoiding the Worst Days? 04/17/2026

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: /episode/index/show/retirewithpurposepodcast/id/40615165

558: By the Numbers: The Bucket Strategy vs. 60-40 - Who Really Wins? 04/10/2026

557: By the Numbers: The Fragile Decade That Could Make (or Break) Your Retirement 04/03/2026

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: /episode/index/show/retirewithpurposepodcast/id/40493345

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: /episode/index/show/retirewithpurposepodcast/id/40292110

554: Freedom After 50: Why Retirement Fear Might Be a Sign You’re Ready 03/13/2026

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: /episode/index/show/retirewithpurposepodcast/id/40291670

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: /episode/index/show/retirewithpurposepodcast/id/40224740

551: Freedom After 50: Why Retirement Decisions Feel Heavier — and What to Do About It 02/27/2026

Retire With Purpose - The Retirement Podcast

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