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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:
    466: The Four A's of a Regret-Free Retirement Nov 08, 2024
    Show notes

    Successfully transitioning from the end of work into retirement takes work. But what does that "work" really involve?

    In this episode, we discuss:

    • What it means to have a non-financial, diversified retirement
    • How to create a life map
    • How to leverage your past to create a fulfilling future
    • The concept of "radical resistance"

    Today's article is from the Harvard Business Review titled, Retire Without Regrets. 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/466

    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


    465: Tax-Efficient Retirement Planning: IRAs and 401(k)s vs. Taxable Accounts Nov 01, 2024
    Show notes

    What is the best type of account for you to allocate your retirement savings? One of the biggest factors in helping you make this decision will be taxes.

    In this episode, we discuss:

    • Current tax deduction vs. ongoing tax deferral
    • Impact of the SECURE Act
    • Why tax location is important
    • How to factor in tax-free accounts

    Today's article is from Morningstar titled, The True Tax Benefit of IRAs and 401(k)s. 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/465

    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


    464: The Conscious Elder Revolution: Reclaiming Ancient Wisdom for a Deeper Life Oct 25, 2024
    Show notes

    What does it mean to be a "Conscious Elder?" With a strong sense of self awareness, it's about discovering how to unlock the deeper wisdom your story has to offer.

    In this episode, we discuss:

    • The concept of Conscious Eldering
    • What it means to share your wisdom
    • How ancient theologies can bring your life clarity now
    • Steps to embrace being a Conscious Elder

    Today's article is from our very own blog titled, The Conscious Elder Revolution: Reclaiming Ancient Wisdom for a Deeper Life. 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/464

    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


    463: Why Investment Survival is Key to a Successful Retirement Portfolio Oct 18, 2024
    Show notes

    Your bottom line when it comes to successful investing for retirement isn't maximizing returns. Instead, survival should be your primary goal; not only avoiding disastrous financial outcomes, but having the ability to manage your emotions.

    In this episode, we discuss:

    • What it means to "diversify from disaster"
    • Understanding investment longevity
    • How to leverage historical averages
    • Survivorship bias

    Today's article is from Behavioural Investment titled, Investors Must Survive. 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/463

    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


    462: Strategies to Maximize Your Social Security Benefits with Mary Beth Franklin Oct 14, 2024
    Show notes

    Today, I'm talking to Mary Beth Franklin. Mary Beth is a CERTIFIED FINANCIAL PLANNER, a former Capitol Hill reporter at United Press International, and the retirement and tax editor at Kiplinger Personal Finance. She also has a new edition of her bestselling book, Maximizing Social Security Benefits, a must-read for retirees and pre-retirees.

    My first interview with Mary Beth was our most downloaded and most watched episode of this podcast, so I'm thrilled to have another chance to talk to her about Social Security (and if you haven't listened to that first episode, be sure to do so before diving into this one, as it covers the foundational elements of Social Security).

    In today's conversation, we discussed what's changed about Social Security over the last several years, how to take advantage of these changes in your financial and retirement planning, and, of course, the future of Social Security and its potential insolvency. You'll also hear what semi-retirement looks like for Mary Beth, as she very recently semi-retired herself, and shares advice for anyone who still enjoys working in their pre-retirement years.

    GET A FREE ACCESS TO MARY BETH'S BOOK: MAXIMIZING SOCIAL SECURITY BENEFITS

    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:

    • Why so many of the Social Security claiming strategies that became popular in the late 2000s have disappeared.
    • What it would mean for Social Security to become insolvent–and why it's highly unlikely for anything to be done about it anytime soon.
    • How your Social Security is calculated, and how to get a clear picture of what your benefits look like (or would look like) right now.
    • Why more people regret claiming benefits too early rather than too late.
    • Social Security claiming strategies that haven't been eliminated by Congress, especially for divorced and widowed retirees.
    • What Mary Beth has learned from her husbands' retirement and her own semi-retirement.

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

    Show Notes: Howardbailey.com/462

    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


    461: The Retirement Myth: How to Revisit, Reflect, and Reinvent Your Next Chapter Oct 11, 2024
    Show notes

    Retirement isn't the finish line. It's a time to rewind and rediscover the next phase of your life as a time of reinvention and impact.

    In this episode, we discuss:

    • The origins of retirement
    • How to navigate forced retirement
    • What is a "Repurposement Plan"?

    Today's article comes from our very own blog titled, Rewind Retirement: Revisit, Reflect, and Reinvent Your Next Chapter. 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/461

    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


    460: Are We in the Longest Bull Market in History? Oct 04, 2024
    Show notes

    Are we living in the longest bull market in history – or is a major market crash on the way? To gain some clarity, it can be helpful to understand how today's economy compares to years' past.

    In this episode, we discuss:

    • Today's market vs. the 80s and 90s
    • Cyclical vs. secular markets
    • How interest rate cuts impact the market

    Today's article is from A Wealth of Common Sense titled, An Epic Bull Market. 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/460

    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


    459: An Estate Planning Alternative: Pros and Cons of a Living Inheritance Sep 27, 2024
    Show notes

    If you're a parent, do you plan to leave your child/children an inheritance? While generally, this wealth transfers upon your passing, another option to consider is the concept of a living inheritance.

    In this episode, we discuss:

    • The impact of a living inheritance
    • Why you need to have open dialogue about your estate plan with children
    • How to strike a balance between transferring wealth today and in the future
    • Gifting tax considerations

    Today's article is from WealthManagement.com titled, Pros and Cons of a Living Inheritance. 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/459

    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


    458: Is the Pursuit of Happiness Killing Your Second Half of Life Joy? Sep 20, 2024
    Show notes

    The happiness you experience is built through mindful, compassionate actions. However, in the second half of life, the quest isn't for fleeting happiness anymore; it's for something deeper: Joy.

    In this episode, we discuss:

    • Happiness vs. joy
    • 5 barriers to joy
    • 5 practices to cultivate joy
    • The power of relationships

    Today's article comes from our very own blog titled, Five Practices to Cultivate JoyListen 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/458

    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


    457: Finding Meaningful Work in a Post-Career World with Bruce Feiler Sep 16, 2024
    Show notes

    Today, I'm thrilled to welcome Bruce Feiler back to the podcast. Bruce has written seven New York Times bestsellers, given three TED Talks viewed more than 4 million times and teaches the TED course How to Master Life's Transitions, and has been a longtime columnist for the New York Times.

    While our previous conversation was all about navigating transition, this episode focuses on Bruce's new book, The Search: Finding Meaningful Work in a Post-Career World. In the book, Bruce shares a toolkit with 21 questions to find work that you love.

    In our conversation, we explore the different aspects of work that make it more meaningful, what a "workquake" is and why the average American has at least 20 of them in their lifetime. We'll also walk you through the process of conducting a "meaning audit" to live the life you want–not the one you think you should.

    GET A FREE ACCESS TO BRUCE'S BOOK: THE SEARCH: FINDING MEANINGFUL WORK IN A POST-CAREER WORLD

    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:

    • What Bruce learned from the time he spent working with his grandfather, and how that experience shaped the rest of his life.
    • Why we're seeing suicide rates skyrocket for retirees and pre-retirees.
    • What "post-career" really means–and how Bruce's interviews with over 500 everyday Americans helped him develop a better understanding of life's transitions.
    • The common traits of people that love what they do.
    • Why work doesn't need to be miserable, despite what history and narratives have told us
    • How to find balance and fulfillment at any age by writing your own work story.

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

    Show Notes: Howardbailey.com/457

    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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