Retire With Purpose - The Retirement Podcast

Updated: 18 Jul 2025 • 512 episodes
retirewithpurpose.com/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.

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Are your Required Minimum Distributions (RMDs) setting you up for failure? Find out how sequence of returns risk combines with RMD rules to create a hidden hazard—and how smart planning, asset allocation, and timely Roth conversions can help you sidestep it.   In this episode, we discuss:  Why RMDs are self-regulating

28 min
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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 Man

53 min
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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 conn

40 min
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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

23 min
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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

43 min
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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 t

22 min
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