Retire With Purpose - The Retirement Podcast

Casey Weade
  • 4.7 (557)
  • Investing
  • Updated Weekly

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.

  1. 3d ago

    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 How I Finally Stopped Caring About Spending. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/571 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu  📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

    24 min

  2. Jun 12

    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 The Shockingly Simple Math Behind Social Security. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/570 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu  📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

    27 min

  3. Jun 8

    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: HowardBailey.com/569 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu  📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

    47 min

  4. Jun 5

    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, The 4 Phases of Retirement. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/568 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu  📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

    21 min

  5. May 29

    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, Do You Really Need a Trust? And Other Estate Planning Questions Retirees Ask Most. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/567 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu  📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

    32 min

  6. May 22

    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 Howard Bailey Financial, Casey Weade is joined by Mike Drak to explore why retirement can trigger a deeper search for purpose, identity, and fulfillment. Show Notes: HowardBailey.com/566 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu  📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

    20 min

  7. May 15

    By the Numbers: Why 42% of Inheritances Disappear Within a Year

    What if the biggest risk to your legacy isn't taxes, but what your heirs do with the money once it's in their hands?  Topics covered in this episode:  Emotional and psychological triggers behind overspending Wealth transfer vs. wealth preservation Ways to give heirs a "second chance" with smarter distributions The role of trusts, trustees, and incentive-based planning Why communication with heirs is essential to a lasting legacy Today's article is from ThinkAdvisor blog titled Heirs Beware: 42% Spend Inheritance Within a Year, Study Finds. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/565 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu  📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

    24 min

  8. May 11

    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: HowardBailey.com/564 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu  📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

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4.7
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About

Whether you are in retirement or have yet to make the transition, The Retire With Purpose podcast is a show designed to help you maximize your financial confidence and elevate your fulfillment in this chapter of life. Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and CEO of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you've always imagined and deserve. Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations. ©2026 HOWARD BAILEY FINANCIAL, INC.

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