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.

502: Freedom After 50: The Hidden Cost of Delayed Gratification in Retirement 05/30/2025

501: The Four Futures of Retirement: Which Path Are You On? 05/23/2025

500: Freedom After 50: 6 Crucial Signs You're Ready for a New Direction 05/16/2025

499: Retirement Income Strategies to Quell Inflation Fears and Spend Comfortably with David Blanchett 05/12/2025

499: Retirement Income Strategies to Quell Inflation Fears and Spend Comfortably with David Blanchett Today, I'm thrilled to welcome David Blanchett back to the podcast. David is the Managing Director and Head of Retirement Research at PGIM DC Solutions and one of the most respected voices in retirement income planning today. You've likely come across his work in Morningstar, Kiplinger, and our Weekend Reading series—and for good reason. His research has earned accolades from nearly every major financial planning organization. In our conversation, we picked up where we left off back in Episode 55 with David's groundbreaking research on retirement spending patterns and adapting it to today's environment of elevated interest rates and persistent inflation. From challenging the idea of a "retirement crisis" that is making headlines everywhere to rethinking the 4% retirement income rule, David helps us distill the data and build income strategies grounded in behavioral and financial realities. In our conversation, we discuss the value and confidence that guaranteed lifetime income annuities provide retirees and how inflation concerns are impacting spending patterns. If you're planning your retirement or considering an adjustment to your current plan, this episode is packed with insights to help you spend your hard-earned dollars with confidence and design a secure and fulfilling retirement. In this podcast interview, you’ll learn: Why “retirement crisis” is an overused headline—and why “challenge” is the better word. What David’s research reveals about how real retirees spend—and why most don’t adjust spending for inflation as expected. Why a 5% withdrawal rate may be more appropriate than 4% in today’s interest rate environment. The behavioral power of guaranteed income—and how it gives retirees the freedom to actually enjoy their savings. How to build inflation hedges into your portfolio using tools like TIPS, annuities, and real assets. 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/36431075

498: 4 Ways to Cultivate Character Amid Market Chaos 05/09/2025

497: Freedom After 50: 5 Numbers Stealing Your Time, Wealth, and Joy 05/02/2025

496: Claiming Social Security Early: Is it the Right Strategy for You? 04/25/2025

495: Freedom After 50: The World is Ending… What’s Next? 04/18/2025

494: Beyond the Headlines: How Retirees Can Navigate Investment Risks with Larry Swedroe 04/14/2025

494: Beyond the Headlines: How Retirees Can Navigate Investment Risks with Larry Swedroe Today, I’m speaking with Larry Swedroe. Larry is the former Chief Research Officer at Buckingham Strategic Wealth, an accomplished author with 18+ books on investing, and a true pioneer in evidence-based investing. He’s also a well-known advocate for cutting through the financial media noise to focus on strategies that actually work. In Larry’s latest book, Enrich Your Future: The Keys to Successful Investing, he distills decades of financial wisdom into 40 powerful stories that make investing principles easy to understand and apply. In our conversation, Larry shares the science behind behavioral finance and explains why most investors fall prey to emotional biases, media hype, and market timing traps. We also dive into why passive investing remains a leading strategy among investors, how to truly measure risk, and why a globally diversified portfolio beats stock-picking in the long run. GET FREE ACCESS TO LARRY’S BOOK TITLED, ENRICH YOUR FUTURE: THE KEYS TO SUCCESSFUL 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 passive investing isn't just a trend—it’s a game-changer for wealth-building. The biggest mistakes investors make and how to avoid them. The difference between risk and uncertainty, and why most investors get it wrong. Why the market is smarter than any single investor and what that means for your portfolio. How to structure an investment portfolio based on empirical research, not emotions. The surprising link between retirement, purpose, and mental health—especially for retired men. 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/35928405

493: Chaotic Markets: A 4-Point Checklist to Safeguard Your Retirement Savings 04/11/2025

492: 3 Levels of Retirement Readiness: Where Do You Stand? 04/04/2025

491: Freedom After 50: 8 Reasons the Month You Retire Matters 03/28/2025

490: Retirement Withdrawal Strategies in Down Markets: Should You Shift Yours? 03/21/2025

489: Freedom After 50: The 4 Myths of Security Keeping You Stuck Today and Fearful of Tomorrow 03/14/2025

488: From Accumulating to Spending: 20 Lessons for a Happy & Successful Retirement with Christine Benz 03/10/2025

488: From Accumulating to Spending: 20 Lessons for a Happy & Successful Retirement with Christine Benz Today, I'm very excited to welcome Christine Benz back to the podcast. Christine is the Director of Personal Finance and Retirement Planning at Morningstar. She has become a trusted voice in the industry and has been recognized as one of Barron’s Top 100 Most Influential Women in Finance and one of the Ten Most Influential Women in Wealth Management. She’s also the co-host of The Long View and How to Retire podcasts where she brings a wealth of expertise and real-world insight to every conversation. In her newest book, How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement, Christine draws from her “Me Search” project and lays out practical strategies that help you transition from a lifetime of accumulation to a lifestyle rich in purpose and meaningful spending. In our conversation, Christine outlines the importance of practicing your retirement lifestyle before you fully commit. She explains how experimenting with sabbaticals and trial runs can help you strike the right balance between structure and flexibility. We discussed the movement of rethinking the traditional 4% rule with a bucket strategy—so you can build confidence in managing your cash flow and spending. GET FREE ACCESS TO CHRISTINE’S BOOK TITLED, HOW TO RETIRE: 20 LESSONS FOR A HAPPY, SUCCESSFUL, AND WEALTHY RETIREMENT 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 testing your retirement lifestyle before you retire can save you stress later. How a balanced mix of routine and flexibility fuels a fulfilling daily life. Why rethinking the 4% rule with a bucket strategy builds spending confidence. How proactive long-term care planning can shield you from future costs. Why syncing your spending with your portfolio and other income sources reduces fear and anxiety. The smart steps women can take to overcome unique retirement challenges. 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/35445930

487: Should You Pay Off Your Mortgage Before Retirement? 03/07/2025

486: Freedom After 50: How to Talk About the Tough Stuff—Money, Religion & Politics 02/28/2025

485: Top 5 Retiree Regrets and How to Avoid Them 02/21/2025

484: Freedom After 50: Fearless Freedom – Unlocking Radical Resilience for Life’s Next Chapter 02/14/2025

483: The Future of Tax Rates: How to Keep More of Your Money and Pay Less Taxes with Ed Slott 02/10/2025

483: The Future of Tax Rates: How to Keep More of Your Money and Pay Less Taxes with Ed Slott Today, I'm joined by one of the country's most renowned tax and retirement distribution experts—Ed Slott. Ed is a CPA, best-selling author, and the founder of Ed Slott and Company. He’s also the Professor of Practice at the American College of Financial Services and The Wall Street Journal has named him the best source for IRA advice. We discussed his latest book, The Retirement Savings Time Bomb Ticks Louder, which is the ultimate guide to reclaim control of your financial future. We also discussed how to navigate taxes in retirement, Roth conversion strategies, the future of tax rates, and why IRAs may be the worst asset to pass on to your beneficiaries. In our conversation, Ed weighs in on whether the new administration will extend the TCJA (Tax Cuts & Jobs Acct), the potential downsides of the extension, and why worrying about timing the market on Roth conversions isn't worth the stress. He always shares his expertise on why investors should take advantage of historically low tax rates while you can. GET FREE ACCESS TO ED’S BOOK TITLED, THE RETIREMENT SAVINGS TIME BOMB TICKS LOUDER 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 most investors and advisors don’t realize how much tax they’ll owe on their retirement savings. The critical difference between tax preparation and tax planning—and why ignoring tax planning can cost thousands of dollars. The "sweet spot" years for Roth conversions—before RMDs kick in at age 73. The biggest mistakes people make with IRAs and 401(k)s and how to avoid unnecessary tax landmines. What Ed predicts will happen to the Tax Cuts & Jobs Acct and tax rates in the coming years. The power of life insurance as a tax-free legacy tool and why Ed personally uses it in his own planning. Our Market Outlook Webinar is live! Visit to register. Show Notes: Rate & Review the Podcast: 📧 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/35155395

482: Freedom After 50: How to Build a Legacy That Will Outlast You—Exploring the Wise Wealth Matrix - Part 4 02/07/2025

481: Comparing 4 Flexible Income Strategies for Retirement 01/31/2025

480: Freedom After 50: The Shadow Side of Wealth - Exploring the Wise Wealth Matrix - Part 3 01/24/2025

480: Freedom After 50: The Shadow Side of Wealth - Exploring the Wise Wealth Matrix - Part 3 Are you using your net worth as a score card? Join us for Part 3 of our exploration of the Wise Wealth Matrix and find out how wisdom can help you redefine wealth as a tool for meaning, balance, and connection. In this episode, we discuss: 3 cultural norms most distorted by modern society Risks associated with the pursuit of “more” Pros and cons of “hustle culture” How to live authentically Listen in as Casey Weade is once again joined by Les McDaniel to discuss the Wise Wealth Matrix and how applying wisdom can transform your perspective on wealth. To receive your FREE WISE Wealth Assessment worksheet, text WISE to 888-599-4491 Our Market Outlook Webinar is live! Visit to register. Show Notes: Rate & Review the Podcast: 📧 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/34964290

479: Our 2025 Market Predictions 01/17/2025

478: Cracking the Code to Maximize Happiness By Finding Meaning and Purpose in Retirement with Jordan Grumet, MD 01/13/2025

478: Cracking the Code to Maximize Happiness By Finding Meaning and Purpose in Retirement with Jordan Grumet, MD Today, I’m thrilled to welcome Dr. Jordan Grumet back to the podcast. Jordan is the Associate Medical Director at Unity Hospice, a financial blogger, and the host of the Earn and Invest Podcast. In his new book, The Purpose Code: How to Unlock Meaning, Maximize Happiness, and Leave a Lasting Legacy, he follows up his work in Taking Stock to explore how to make a mark, set goals that are meaningful to you, and create a map for anyone to find happiness. In our conversation, Jordan shares examples, exercises, and tools you can use to define and create meaning in your life right now. We talk about how finding meaning and purpose is accomplished by taking action and working towards it, and how Jordan’s rules help turn your “purpose anchors” into forward momentum. GET FREE ACCESS TO JORDAN’S BOOK TITLED THE PURPOSE CODE: HOW TO UNLOCK MEANING, MAXIMIZE HAPPINESS, AND LEAVE A LASTING LEGACY 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 888-599-4491 and we’ll make sure you get signed up for free. It’s that simple! In this podcast interview, you’ll learn: How an antique store owner who collected baseball cards taught Jordan the power of purpose, self-confidence and community. That finding your purpose after retiring can take months, and that’s okay. What makes talking about purpose so anxiety-inducing–and how Instagram and TikTok have made it worse. Why we all need interpersonal connections and community. How Jordan describes the difference between purpose and goals. Our Market Outlook Webinar is live! Visit to register. Show Notes: Rate & Review the Podcast: 📧 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/34703810

477: 10 Steps to Prepare Your Finances for Retirement 01/10/2025

476: Freedom After 50: Exploring the Wise Wealth Matrix - Part 2 01/03/2025

475: Freedom After 50: Exploring the Wise Wealth Matrix - Part 1 12/27/2024

475: Freedom After 50: Exploring the Wise Wealth Matrix - Part 1 What does it mean to be wealthy and wise in mid-life? As part of our retirement coaching process, this is your opportunity to discover how to pave the way for an intentional, purpose-filled life by leveraging our Wise Wealth Blueprint. In this episode, we discuss: What it means to live in the “Freedom Zone” The power of “long life learning” The three pillars of wealth Listen in as Casey Weade is joined by Les McDaniel to reveal the Wise Wealth Matrix, and offer guidance on how to move from feeling stuck in the isolation zone, stress zone or comfort zone and into the freedom zone. To receive your FREE WISE Wealth Assessment worksheet, text WISE to 888-599-4491 Our Market Outlook Webinar is live! Visit to register. Show Notes: Rate & Review the Podcast: 📧 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/34555260

474: The Reality of Investment Risk: Why Low Probability of Loss Doesn’t Equal Low Risk 12/20/2024

473: Retirement Tax Planning: Exploring the Impact of a Republican Trifecta on Your Taxes and Bottom Line 12/13/2024

Retire With Purpose - The Retirement Podcast

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