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    Business

    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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    Latest Episodes:
    526: Rethinking Social Security: Why Waiting Until 70 Isn't Always Best Oct 10, 2025
    Show notes

    What if the common advice to wait until age 70 for Social Security isn't always the best move? Could claiming earlier actually give you more freedom and peace of mind in retirement?

    In this episode, we discuss:

    • Risks of "blanketed" Social Security advice
    • Determining your expected value vs. expected utility
    • Mortality, sequence of returns, and policy risks
    • Pinpointing your "personalized discount rate"

    Today's article is from the Kitces.com blog titled, Why Delaying Social Security Benefits Isn't Always The Best Decision. 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/526

    📧 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


    525: Freedom After 50: 12 Belief Traps Keeping You from a Meaningful and Impactful Retirement Oct 03, 2025
    Show notes

    Retirement is about more than finances — it's about meaning and growth. Join us as we explore common "belief traps" that can hold you back, how to reframe your story, and expand what's possible in the years ahead.

    In this episode, we discuss:

    • How the echo chamber and certainty traps limit perspective and growth
    • Why the comfort trap keeps you stuck — and how to break free
    • The danger of the perfection and irrelevance traps in later life
    • A powerful exercise to reframe your time horizon and live with greater purpose

    Today's article is from our own blog titled 12 Belief Traps Keeping You from a Meaningful and Impactful Retirement. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to uncover common belief traps, how to reframe your story, and practical ways to expand what's possible in the next chapter of life.

    Show Notes: HowardBailey.com/525

    📧 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


    524: A New 4-Bucket Approach to Investing Before and After Retirement Sep 26, 2025
    Show notes

    You're told to shift from "growth" to "protection" the moment you retire and leave the workforce. But is it really that simple? Join us as we break down the false dichotomy of pre- vs. post-retirement investing, showing why your strategy should always include a mix of offense and defense.

    In this episode, we discuss:

    • Your biggest risks in retirement
    • How to leverage all your assets (stocks, bonds, pensions, Social Security, real estate, life insurance, etc. in your income strategy)
    • Forbes writer Tim Maurer's 4-Bucket Approach to a holistic retirement plan

    Today's article is from the Forbes titled, The (False) Dichotomy Of Investing Before And After 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/524

    📧 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


    523: Freedom After 50: Beyond the Pyramid—Rethinking Happiness in Retirement Sep 19, 2025
    Show notes

    Many of us spend decades climbing Maslow's pyramid — seeking security, comfort, and experiences — only to realize that the top is where true joy lives. Join us as we explore the "Happiness Hierarchy" and why lasting fulfillment comes not from what you buy or where you travel, but from who you become.

    In this episode, we discuss:

    • How to shift from "having enough" to "becoming more"
    • Why Maslow's hierarchy is often misunderstood
    • The three levels of happiness
    • Why reflection unlocks the freedom to become

    Today's article is from Jordan Grumet blog titled Rethinking Maslow. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore the "Happiness Hierarchy.

    Show Notes: HowardBailey.com/523

    📧 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


    522: The Six Pillars to Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 2 Sep 15, 2025
    Show notes

    Living longer is one thing. Living well is another. In Part 2 of my conversation with Dr. Bobby Dubois, we unpack the final three pillars of his blueprint for longevity: mind-body harmony, heat & cold exposure, and social relationships.

    Dr. Bobby explains why practices like meditation, breathwork, and even walking in nature can calm the brain and lower anxiety. We also explore the science-backed benefits of sauna and cold plunging—and what's hype versus what's real. Finally, we uncover why social connection is the single strongest predictor of living a long, healthy, and fulfilling life.

    If you want practical, evidence-based ways to boost your health, not just your longevity, this episode shows you how to put it all together.

    In this podcast interview, you'll learn:

    • How meditation and breathwork improve brain and heart health.
    • Why saunas reduce risk of heart attack and stroke.
    • The science behind cold plunges and their impact on mood and happiness.
    • Why social connection is the strongest predictor of longevity, even more than exercise.
    • How to be your own "quarterback" for health and wellness instead of hiring multiple coaches and gurus.

    Show Notes: HowardBailey.com/522

    📧 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


    521: 5 Timeless Proverbs for a Wise and Wealthy Retirement Sep 12, 2025
    Show notes

    What can ancient wisdom teach us about modern retirement? From budgeting with freedom to preparing for life's surprises, tackling debt, planning wisely, and redefining generosity in retirement, insights of the past can show how true wealth goes beyond dollars.

    In this episode, we discuss:

    • The importance of having a budget, even in retirement
    • Emergency fund: How much do you need?
    • Debt and dependence
    • Generosity in retirement: Stewardship, legacy planning, and the "Die with Zero" philosophy

    Today's article is from our very own blog post titled, Five Timeless Proverbs for a Wise and Wealthy 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/521

    📧 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


    520: The Six Pillars of Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 1 Sep 08, 2025
    Show notes

    Today, I'm speaking with Dr. Bobby Dubois. Dr. Bobby is a Harvard-educated physician, Board-Certified in Internal Medicine with over 25 years of experience. He's an author, entrepreneur, wellness doctor, and Ironman Triathlete. Most recently, he led a health policy research organization in Washington, D.C. (National Pharmaceutical Council) as its Chief Science Officer and Executive Vice President.

    Prior to that, he served as the Chief Medical Officer of Cerner Life Sciences and co-founded Proto Care Sciences. He's the host of the Live Long and Well podcast and has made it his mission to help others cut through the noise and live longer with more energy as they age.

    The simple fact is, most retirees and pre-retirees want more time, energy, and independence to enjoy the life they've worked so hard to build. However, the reality is that longevity without good health won't achieve the lifestyle that most retirees envisioned during their working years.

    In part 1 of this 2-part conversation, we delve into the life-extending benefits of aerobic exercise, the scientific advantages of consistent sleep, and the surprising role of relationships in promoting increased longevity. Dr. Bobby outlines his six pillars of health and explains how to apply them in retirement. And here's the good news: it's never too late to start.

    In its simplest form, his advice is strikingly similar to what you'd hear from a financial advisor: It's much better to start saving and exercising young, but it's never too late to start. If you want to live not only longer, but better, this episode provides a clear path and roadmap to get there.

    GET A FREE COPY OF DR. BOBBY DUBOIS' E-BOOK, HOW TO LIVE LONG AND WELL

    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 exercise is the most powerful lever for longevity.
    • The six pillars of health that drive longevity and overall wellness.
    • Why it's never too late to start strength training and the surprising results from those who start later in life.
    • The importance of a good sleep and tips to make it happen consistently.
    • How sleep clears toxins from the brain and extends healthspan.
    • How to diagnose the placebo effect to know when changing routines is working or not.
    • Why social connection is just as important as diet and exercise.

    Show Notes: HowardBailey.com/520

    📧 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


    519: Freedom After 50: How to Break Free from Your Old Story and Shape Wisdom That Lasts Sep 05, 2025
    Show notes

    Retirement isn't the end — it's your greatest opening. Join us as we explore how to break free from old stories, embrace wisdom, and turn life's challenges into a legacy of meaning and impact.

    In this episode, we discuss:

    • Why lifequakes = growth
    • Fluid vs. crystallized intelligence
    • How to redefine success in retirement
    • The role of curiosity and engagement

    Today's article is from our very own blog post titled, Freedom After 50: Break Free from Your Old Story and Shape the Wisdom That Lasts. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore how to transform lifequakes into growth, embrace wisdom, and redefine success with curiosity, engagement, and lasting impact.

    Show Notes: HowardBailey.com/519

    📧 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


    518: Beyond Investment Risk: Why Income Risk Could Change Your Retirement Plan Aug 29, 2025
    Show notes

    Most financial plans focus on how your investments perform, but what about the risks to your income along the way? Join us as we unpack groundbreaking research that shows why traditional retirement calculators and rules of thumb may be leaving you exposed.

    In this episode, we discuss:

    • Traditional planning gaps
    • The three types of income risk
    • Risk Capacity vs. Need vs. Attitude
    • Retirement "buffering"
    • The Retirement Red Zone

    Today's article is from Morningstar, titled The Importance of Incorporating Income Risk Into Financial Planning. 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/518

    📧 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


    517: Freedom After 50: The Need for Next—Finding Meaning Beyond Milestones Aug 22, 2025
    Show notes

    Why do so many retirees struggle to find fulfillment after leaving the workforce, and how do they break free from the traps of status, constant pleasure-seeking, and busywork? Together, we unpack practical strategies for moving beyond milestones to craft a retirement rich in purpose, connection, and legacy.

    In this episode, we discuss:

    • The "need for next" mindset
    • Five common non-financial retirement traps
    • The "good enough" principle
    • How to avoid pleasure-only living and flow with life's seasons

    Today's article is from Mr-Stingy.com titled The Need for Next. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore strategies to embrace purpose, connection, and legacy in retirement.

    Show Notes: HowardBailey.com/517

    📧 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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