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Retire With Purpose - The Retirement Podcast

Casey Weade
Retire With Purpose - The Retirement Podcast
Latest episode

589 episodes

  • Retire With Purpose - The Retirement Podcast

    589: The Hidden Tax Drag That Could Cost You Millions

    2026/10/02 | 28 mins.
    The market's return is only part of the story. Find out how taxes can quietly erode your retirement wealth and the planning strategies that can help you keep more of what you've worked so hard to build.
    In this episode, you'll learn:
    Why tax drag can cost far more than the tax bill you see
    How asset location can improve your after-tax returns
    Why the timing of a sale can make a meaningful difference
    How Roth conversions and capital-gain harvesting can fit into a retirement tax strategy
    The KEEP framework for thinking about taxes throughout retirement
    Today's article is from SSRN titled, Uncle Sam's Cut: A Century of the Federal Tax Drag on US Equity Returns. Listen in as 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/589
    📧 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
  • Retire With Purpose - The Retirement Podcast

    588: The 90-10 Rule: What Really Matters After You Retire

    2026/09/25 | 20 mins.
    What if the thing you spend 90% of your time planning for before retirement becomes the thing you think about least once you get there? Fritz Gilbert of The Retirement Manifesto joins us to explore the 90-10 rule and why preparing for a fulfilling
    retirement requires just as much thought about your life as your money.
    In this episode, you'll learn:
    How to start planning the non-financial side of retirement
    Why analytical people can get stuck in endless "what-if" scenarios
    How to prepare for boredom, isolation, and loss of identity
    The "spokes" that help create balance in your life
    How to stress-test your life — not just your retirement portfolio
    Listen in as CEO of Howard Bailey Financial, Casey Weade and Fritz Gilbert provide thoughtful insights and advice on how it applies to your unique financial situation.
    Show Notes: HowardBailey.com/588
    📧 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
  • Retire With Purpose - The Retirement Podcast

    587: Why Age-Gap Couples Need a Different Retirement Plan

    2026/09/18 | 25 mins.
    If you and your spouse are several years apart in age — or simply plan to retire at different times — this episode reveals the financial and relationship challenges most couples never anticipate and how to prepare for them.
    Listen for insight on:
    Why retirement comes in three distinct phases
    How to create a "retirement operating agreement" as a couple
    Medicare and healthcare planning pitfalls for age-gap couples
    Social Security strategies that could impact lifetime income
    Tax planning opportunities before both spouses retire
    Practical ways to build a retirement plan that works through every stage
    Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade provides thoughtful insights and advice on how it applies to your unique financial situation.
    Show Notes: HowardBailey.com/587
    📧 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
  • Retire With Purpose - The Retirement Podcast

    586: Why Social Connections Are Essential for a Healthy Retirement

    2026/09/14 | 55 mins.
    Today, I'm excited to welcome Ken Stern to the podcast. Ken is the founder and chair of the Longevity Project, host of Century Lives from the Stanford Center on Longevity, former CEO of NPR, and author of Healthy to 100: How Strong Social Ties Lead to Long Lives. His research explores an aspect of retirement planning that rarely gets enough attention: our social health.
    Far too many people spend years wondering whether they've saved enough to retire, but very few think about whether they are socially ready to retire. Work provides much more than a paycheck. It provides routines, relationships, purpose, and regular interaction with other people, but when that disappears, retirement can become far more isolating than most people anticipate.
    In our conversation, Ken explains why strong social connections are critical to our health and longevity, how to replace the relationships and routines we lose when we leave the workforce, and why we should approach retirement with the same intentionality we brought to our careers.
    GET A FREE COPY OF KEN'S BOOK,  HEALTHY TO 100: HOW STRONG SOCIAL TIES LEAD TO LONG LIVES
    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 being financially ready for retirement doesn't necessarily mean you're socially ready.
    How leaving the workforce can unexpectedly disrupt your relationships, routines, and sense of purpose.
    Why strong social connections can play such an important role in healthy aging and longevity.
    What longer-lived countries can teach us about work, learning, volunteering, and intergenerational connection.
    How place planning and proximity can make it easier to build meaningful relationships in retirement.
    Why your social connection plan should begin long before your final day of work.
    Show Notes: HowardBailey.com/586
    📧 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
  • Retire With Purpose - The Retirement Podcast

    585: The U-Curve of Happiness: Why Life Gets Better with Age

    2026/09/11 | 23 mins.
    What if getting older doesn't mean losing happiness, but gaining more of it? Author Don Ezra explores the surprising science behind the U-curve of happiness and why perspective, purpose, gratitude, and letting go of perfection can make the years
    ahead some of your best.
    In this episode, you'll learn:
    Why happiness often dips in midlife and rises again later in life
    How dopamine influences our desire for "more"
    The connection between purpose and life satisfaction
    A simple exercise for cultivating gratitude and greater life satisfaction
    Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade and Don Ezra provide thoughtful insights and advice on how it applies to your unique financial situation.
    Show Notes: HowardBailey.com/585
    📧 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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About 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.
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