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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:
    486: Freedom After 50: How to Talk About the Tough Stuff—Money, Religion & Politics Feb 28, 2025
    Show notes

    In retirement and beyond, strong social connections are at the heart of human happiness and fulfillment. But to create those solid relationships, you often need to learn how to dig deeper with your conversations.

    In this episode, we discuss:

    • Why quality of relationships is crucial for longevity and happiness
    • How the "Coin's Edge" philosophy helps you understand other points of view
    • The importance of curiosity for growth
    • How to have deeper conversations with the TALK acronym

    Today's article is from The Atlantic titled, Don't Make Small Talk. Think Big Talk. 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/486

    📧 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/3z5mXIw

    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

    485: Top 5 Retiree Regrets and How to Avoid Them Feb 21, 2025
    Show notes

    You want to ensure you have all your ducks in a row before entering retirement. Today, we're pulling back the curtain on the biggest retiree regrets so that they don't become yours too.

    In this episode, we discuss:

    • Do you need to be a millionaire to retire?
    • The Social Security "breakeven" number
    • Pros and cons of bringing debt into retirement
    • Preparing for a forced retirement

    Today's article is from The Retirement Manifesto titled, 5 Top Regrets of Retirees (and how to avoid them). 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/485

    📧 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/3z5mXIw

    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

    484: Freedom After 50: Fearless Freedom – Unlocking Radical Resilience for Life's Next Chapter Feb 14, 2025
    Show notes

    What role does spirituality play in your life and how can it help you cultivate a purpose-driven retirement? Join us for a conversation about wisdom, the deeper truths that have endured across time, and why this is all central to a purposeful retirement.

    In this episode, we discuss:

    • How spirituality and faith impact retirement
    • When and where fear can impact happiness after 50
    • The importance of connecting with others who have different viewpoints

    Listen in as Casey Weade is once again joined by Les McDaniel to discuss the role of spirituality in shaping a purposeful retirement.

    To receive your FREE WISE Wealth Assessment worksheet, text WISE to 888-599-4491

    Show Notes: Howardbailey.com/484

    📧 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/3z5mXIw

    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

    483: The Future of Tax Rates: How to Keep More of Your Money and Pay Less Taxes with Ed Slott Feb 10, 2025
    Show notes

    Today, I'm joined by one of the country's most renowned tax and retirement distribution experts—Ed Slott. Ed is a CPA, best-selling author, and the founder of Ed Slott and Company. He's also the Professor of Practice at the American College of Financial Services and The Wall Street Journal has named him the best source for IRA advice.

    We discussed his latest book, The Retirement Savings Time Bomb Ticks Louder, which is the ultimate guide to reclaim control of your financial future. We also discussed how to navigate taxes in retirement, Roth conversion strategies, the future of tax rates, and why IRAs may be the worst asset to pass on to your beneficiaries.

    In our conversation, Ed weighs in on whether the new administration will extend the TCJA (Tax Cuts & Jobs Acct), the potential downsides of the extension, and why worrying about timing the market on Roth conversions isn't worth the stress. He always shares his expertise on why investors should take advantage of historically low tax rates while you can.

    GET FREE ACCESS TO ED'S BOOK TITLED, THE RETIREMENT SAVINGS TIME BOMB TICKS LOUDER

    Here's all you have to do...

    • Step 1.) Subscribe to the podcast and leave an honest rating & review over on iTunes.
    • Step 2.) Text the word BOOK to 866-599-4491 and we'll make sure you get signed up for free. It's that simple!

    In this podcast interview, you'll learn:

    • Why most investors and advisors don't realize how much tax they'll owe on their retirement savings.
    • The critical difference between tax preparation and tax planning—and why ignoring tax planning can cost thousands of dollars.
    • The "sweet spot" years for Roth conversions—before RMDs kick in at age 73.
    • The biggest mistakes people make with IRAs and 401(k)s and how to avoid unnecessary tax landmines.
    • What Ed predicts will happen to the Tax Cuts & Jobs Acct and tax rates in the coming years.
    • The power of life insurance as a tax-free legacy tool and why Ed personally uses it in his own planning.

    Our Market Outlook Webinar is live! Visit https://bit.ly/4bmHkUb to register.

    Show Notes: Howardbailey.com/483

    Rate & Review the Podcast: RetireWithPurpose.com/review

    📧 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/3z5mXIw

    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

    482: Freedom After 50: How to Build a Legacy That Will Outlast You—Exploring the Wise Wealth Matrix - Part 4 Feb 07, 2025
    Show notes

    Are you living a life that reflects the legacy you want to leave behind? Join us as we wrap up our exploration of the Wise Wealth Matrix with this final installment.

    In this episode, we discuss:

    • Why most legacies fail
    • How to leverage the Wisdom & Wealth pillars for legacy planning
    • How to activate legacy with impact

    Listen in as Casey Weade is once again joined by Les McDaniel to discuss the Wise Wealth Matrix and key insights on legacy planning and impact.

    To receive your FREE WISE Wealth Assessment worksheet, text WISE to 888-599-4491

    Our Market Outlook Webinar is live! Visit https://bit.ly/4bmHkUb to register.

    Show Notes: Howardbailey.com/482

    Rate & Review the Podcast: RetireWithPurpose.com/review

    📧 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/3z5mXIw

    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

    481: Comparing 4 Flexible Income Strategies for Retirement Jan 31, 2025
    Show notes

    If you want to spend your hard-earned dollars confidently in retirement, then you need an income plan that aligns with your personal goals.

    In this episode, we discuss:

    • How income strategies have evolved
    • Why retiree spending changes
    • What makes an income strategy "flexible"
    • How to know which income strategy is best for you

    Today's article is from Morningstar.com titled, The Best Flexible Strategies for Retirement Income. 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.

    Our Market Outlook Webinar is live! Visit https://bit.ly/4bmHkUb to register.

    Show Notes: Howardbailey.com/481

    Rate & Review the Podcast: RetireWithPurpose.com/review

    📧 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/3z5mXIw

    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

    480: Freedom After 50: The Shadow Side of Wealth - Exploring the Wise Wealth Matrix - Part 3 Jan 24, 2025
    Show notes

    Are you using your net worth as a score card? Join us for Part 3 of our exploration of the Wise Wealth Matrix and find out how wisdom can help you redefine wealth as a tool for meaning, balance, and connection.

    In this episode, we discuss:

    • 3 cultural norms most distorted by modern society
    • Risks associated with the pursuit of "more"
    • Pros and cons of "hustle culture"
    • How to live authentically

    Listen in as Casey Weade is once again joined by Les McDaniel to discuss the Wise Wealth Matrix and how applying wisdom can transform your perspective on wealth.

    To receive your FREE WISE Wealth Assessment worksheet, text WISE to 888-599-4491

    Our Market Outlook Webinar is live! Visit https://bit.ly/4bmHkUb to register.

    Show Notes: Howardbailey.com/480

    Rate & Review the Podcast: RetireWithPurpose.com/review

    📧 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/3z5mXIw

    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

    479: Our 2025 Market Predictions Jan 17, 2025
    Show notes

    It's that time of year again in the finance world; time to ring in this year's stock market predictions! Are analysts erring toward bull—or bear? We give you our take.

    In this episode, we discuss:

    • How our past market predictions fared
    • How today's market activity compares to the 90s
    • Why we could be due for a correction
    • How technological advancements can impact market activity

    Today's article is from Best Interest blog titled, The Oldest Bad Joke on Wall Street. 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.

    Our Market Outlook Webinar is live! Visit https://bit.ly/4bmHkUb to register.

    Show Notes: Howardbailey.com/479

    Rate & Review the Podcast: RetireWithPurpose.com/review

    📧 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/3z5mXIw

    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

    478: Cracking the Code to Maximize Happiness By Finding Meaning and Purpose in Retirement with Jordan Grumet, MD Jan 13, 2025
    Show notes

    Today, I'm thrilled to welcome Dr. Jordan Grumet back to the podcast. Jordan is the Associate Medical Director at Unity Hospice, a financial blogger, and the host of the Earn and Invest Podcast.

    In his new book, The Purpose Code: How to Unlock Meaning, Maximize Happiness, and Leave a Lasting Legacy, he follows up his work in Taking Stock to explore how to make a mark, set goals that are meaningful to you, and create a map for anyone to find happiness.

    In our conversation, Jordan shares examples, exercises, and tools you can use to define and create meaning in your life right now. We talk about how finding meaning and purpose is accomplished by taking action and working towards it, and how Jordan's rules help turn your "purpose anchors" into forward momentum.

    GET FREE ACCESS TO JORDAN'S BOOK TITLED THE PURPOSE CODE: HOW TO UNLOCK MEANING, MAXIMIZE HAPPINESS, AND LEAVE A LASTING LEGACY

    Here's all you have to do...

    • Step 1.) Subscribe to the podcast and leave an honest rating & review over on iTunes.
    • Step 2.) Text the word BOOK to 888-599-4491 and we'll make sure you get signed up for free. It's that simple!

    In this podcast interview, you'll learn:

    • How an antique store owner who collected baseball cards taught Jordan the power of purpose, self-confidence and community.
    • That finding your purpose after retiring can take months, and that's okay.
    • What makes talking about purpose so anxiety-inducing–and how Instagram and TikTok have made it worse.
    • Why we all need interpersonal connections and community.
    • How Jordan describes the difference between purpose and goals.

    Our Market Outlook Webinar is live! Visit https://bit.ly/4bmHkUb to register.

    Show Notes: Howardbailey.com/478

    Rate & Review the Podcast: RetireWithPurpose.com/review

    📧 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/3z5mXIw

    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

    477: 10 Steps to Prepare Your Finances for Retirement Jan 10, 2025
    Show notes

    How should you modify your portfolio for retirement? It doesn't take a one-size-fits-all approach, but let's begin with the basics.

    In this episode, we discuss:

    • How your emergency fund might change in retirement
    • Why your income strategy is key to retirement success
    • How to fill for your income "gap"
    • Asset vs. tax allocation
    • The "tax oasis"

    Today's article is from The Retirement Manifesto titled, 10 Steps To Prepare Your Finances For 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.

    Our Market Outlook Webinar is live! Visit https://bit.ly/4bmHkUb to register.

    Show Notes: Howardbailey.com/477

    Rate & Review the Podcast: RetireWithPurpose.com/review

    📧 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/3z5mXIw

    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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