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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:
    566: Freedom After 50: How to Avoid Retirement Shock and Find Purpose Again with Mike Drak May 22, 2026
    Show notes

    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


    565: By the Numbers: Why 42% of Inheritances Disappear Within a Year May 15, 2026
    Show notes

    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


    564: Signal vs. Noise: How to Make Smarter Retirement Planning Decisions with Jesse Cramer May 11, 2026
    Show notes

    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


    563: Freedom After 50: From Bucket List to Life Strategy with Jet Vertz May 08, 2026
    Show notes

    What if the goal of your bucket list isn't to slowly check it off, but to finish it, rebuild it, and use it to fuel a more meaningful retirement?

    Topics covered in this episode:

    • How to build a purpose-driven bucket list that actually gets completed
    • Why most bucket lists are too "self-focused" and how to fix that
    • The power of small, achievable goals
    • Why sharing your goals increases follow through
    • The surprising reason retirees come back to create bigger bucket lists

    Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Jet Vertz to rethink the bucket list to explain how completing, rebuilding, and sharing it can fuel a more meaningful retirement.

    Show Notes: HowardBailey.com/563

    📧 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


    562: By the Numbers: Why Your Tax Refund Isn't What You Think May 01, 2026
    Show notes

    Are you actually better off getting a tax refund, or is your brain tricking you into celebrating a financial loss?

    Topics covered in this episode:

    • Tax refunds vs. tax liability: what actually matters
    • Behavioral biases (framing, loss aversion, anchoring, etc.)
    • Strategic tax planning vs. emotional decision-making
    • Real-world examples from retirees and working families
    • How to align tax strategy with long-term financial goals

    Today's article is from Best Interest blog titled We Are So Irrational (Literally) About Taxes. 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/562

    📧 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


    561: Freedom After 50: The 80% Rule That Could Change Your Retirement Timeline with Jordan Grumet, MD Apr 24, 2026
    Show notes

    What if waiting until you're "fully ready" for retirement is actually costing you some of the best years of your life?

    Topics covered in this episode:

    • The controversial "retire at 80%" framework
    • Why most retirees don't run out of money
    • The reality behind retirement spending patterns
    • The emotional and psychological barriers to retiring
    • Why time may be more valuable than financial certainty
    • How to determine if you're closer to retirement than you think

    Today's article is from The Purpose Code blog titled, Retire at 80%. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Jordan Grumet to explore the "retire at 80%" framework and why time may matter more than perfect financial certainty.

    Show Notes: HowardBailey.com/561

    📧 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


    560: By the Numbers: Can You Really Beat the Market by Avoiding the Worst Days? Apr 17, 2026
    Show notes

    What if trying to avoid the market's worst days is actually one of the fastest ways to sabotage your retirement plan?

    Topics covered in this episode:

    • Why best and worst market days often occur back-to-back
    • The math of gains vs. losses — and why it's not equal
    • The "lost decade" and what it teaches investors
    • Why avoiding bad years matters more than avoiding bad days
    • How reduced volatility strategies can stabilize retirement outcomes

    Today's article is from Morningstar titled You Can Beat the Stock Market by Avoiding Its Worst Days. But You Won't. 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/560

    📧 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


    559: How Dopamine Shapes Your Motivation, Happiness, and Purpose in Retirement with Michael Long Apr 13, 2026
    Show notes

    Today, I'm excited to welcome Michael Long to the podcast. Michael is a physicist-turned-writer and the co-author of the international bestseller The Molecule of More. His work explores one of the most powerful forces shaping our lives: the brain chemical dopamine — and how it influences motivation, ambition, and our constant drive for "more."

    Michael is also the author of Taming the Molecule of More: A Step-by-Step Guide to Making Dopamine Work for You. Over the course of his career, he has written speeches for members of Congress, presidential candidates, Fortune 10 CEOs, while also teaching at Georgetown University and producing award-winning screenplays.

    In our conversation, Michael explains why dopamine isn't actually the chemical that makes us happy, it's the chemical that makes us want more. More trips, more gadgets, more fun stuff on our phones. We discuss how this pursuit of "more" drives innovation and progress, but can also leave retirees feeling restless or unfulfilled if they're not careful.

    Michael also shares practical ways to recognize when dopamine is driving your decisions, how to create healthier habits that restore balance, and why learning to live more fully in the present moment can transform your experience of retirement.

    GET A FREE COPY OF MICHAEL'S BOOK, TAMING THE MOLECULE OF 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 dopamine isn't the "happiness chemical" — it's the chemical that drives our desire for more.
    • How dopamine helped humans survive in a world of scarcity and danger.
    • Why modern technology and social media can hijack your dopamine system.
    • How retirees can redirect dopamine toward curiosity, purpose, and meaningful goals.
    • The difference between dopamine (future-focused) and "here-and-now" brain chemicals.
    • Simple habits that help reduce impulsive dopamine-driven decisions.
    • Why learning to pause and appreciate the present moment can dramatically improve life satisfaction in retirement.

    Show Notes: HowardBailey.com/559

    📧 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


    558: By the Numbers: The Bucket Strategy vs. 60-40 - Who Really Wins? Apr 10, 2026
    Show notes

    What if the strategy you trust most for retirement income is quietly costing you hundreds of thousands of dollars?

    Topics covered in this episode:

    • The real driver behind outperformance
    • Sequence of returns risk and the "retirement risk zone"
    • Why rebalancing can help (or hurt) your long-term results
    • The surprising case for increasing equity exposure over time
    • Limitations of bonds in modern retirement portfolios
    • How small tweaks can potentially add six figures to your retirement

    Today's article is from The Retirement Manifesto titled The 60/40 Portfolio vs. The Bucket Strategy. 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/558

    📧 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


    557: By the Numbers: The Fragile Decade That Could Make (or Break) Your Retirement Apr 03, 2026
    Show notes

    What if the real retirement risk zone isn't during retirement… but the five critical years before and after it begins?

    In this episode, you'll learn about:

    • Pre- vs. post-retirement sequence of returns risk
    • How to stress test your retirement plan effectively
    • The role of asset allocation shifts in late-stage accumulation
    • Why target date funds may carry more risk than expected
    • How to build income certainty and protection strategies
    • The psychology of transitioning from growth to preservation

    Today's article is from ThinkAdvisor.com titled Exploring the Retirement Risk Zone. 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/557

    📧 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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