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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:
    416: Elder Justice: Taking the Initiative on Elder Abuse with Marie-Therese Connolly Jan 22, 2024
    Show notes

    Today, I'm talking to Marie-Therese Connolly. MT Connolly is a lawyer working in the courts and in Congress to tackle an ongoing and fundamental issue of elder abuse–both physical and psychological–as well as financial exploitation and wrongful deprivation of rights.

    She was instrumental in architecting the federal Elder Justice Act. She also founded the DoJ's Elder Justice Initiative and authored the Elder Justice Roadmap.

    In her book, The Measure of Our Age: Navigating Care, Safety, Money, and Meaning Later in Life, she addresses the challenges of aging, how things go wrong, and offers powerful tools we can use to forge better and healthier lives for ourselves, our families, and our communities.

    In today's conversation, MT and I discussed how we can protect our parents and grandparents, what our culture teaches us about aging (and conversely, what aging teaches us), and why it's a great time to get old–even though our support systems appear to be broken.

    GET A FREE ACCESS TO MT CONNOLLY'S BOOK TITLED, THE MEASURE OF OUR AGE: NAVIGATING CARE, SAFETY, MONEY AND MEANING LATER IN LIFE

    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 866-482-9559 and we'll make sure you get signed up for free. It's that simple!

    In this podcast interview, you'll learn:

    • Why elder abuse has been a longstanding problem in our society and our world.
    • How we as people underestimate the power of aging and its challenges.
    • What happened as MT fought for the Elder Justice Act, what went wrong, and what she's optimistic about.
    • Why so many people don't realize how many resources they need to cover long-term care, to stay in their homes, or get other support they might need.
    • How to evaluate retirement communities and care homes.
    • The common risks of families taking on caregiving.
    • Why old and young people are meant to spend time together and learn from one another.
    • The special challenges facing solo and childless retirees–and the importance of building community.
    • How to protect yourself and your loved ones from financial exploitation.

    Also, our Market Outlook Webinar is coming soon! To get a registration link once the webinar is available, please text MARKET to (866) 482-9559.

    Show Notes: Howardbailey.com/416

    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


    415: 7 Steps to Use Strategic Thinking to Create the Life (and Retirement) You Want Jan 19, 2024
    Show notes

    What does it look like to build your own life strategy, and why do you really need one? In this episode of the Retire With Purpose Podcast, we're exploring seven questions business corporations leverage that can help you construct a vision for your most impactful, purposeful life.

    Today's article comes from the Harvard Business Review titled, Use Strategic Thinking to Create the Life You Want. 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.

    Also, our Market Outlook Webinar is coming soon! To get a registration link once the webinar is available, please text MARKET to (866) 482-9559.

    Show Notes: Howardbailey.com/415

    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


    414: Our 2024 Market Predictions Jan 12, 2024
    Show notes

    This week's retirement reading is from Of Dollars And Data titled, Will 2024 Be an Up Year for the Stock Market? Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/414.

    Our Market Outlook Webinar is coming soon! To get a registration link once the webinar is available, please text MARKET to (866) 482-9559.

    Show Notes: Howardbailey.com/414

    Rate & Review the Podcast: RetireWithPurpose.com/review

    Sign Up to Casey's Weekend Reading Email!

    Sifting through the copious amount of conflicting financial advice and retirement information can be daunting - but it doesn't have to be! Each week, Casey makes it super easy. He hand-picks 4 of the most important articles you need to read, that are beneficial to you whether you're at, near, or in retirement! If you want them sent straight to your inbox, sign up by visiting RetireWithPurpose.com/weekend-reading


    413: Tools for Processing Grief to Experience Post-Traumatic Growth with Krista St-Germain Jan 08, 2024
    Show notes

    Today, I'm speaking with Krista St-Germain. Krista is a Master Certified Life Coach, grief expert, and host of the Widowed Mom Podcast, where she specializes in helping widows move forward and love their life again.

    When her husband was killed by a drunk driver just 3 ½ months after their wedding, her life was flipped upside down. As she worked through her loss, she realized that she can leverage her loss to make her life better and has helped others do the same. Her Moms Go On program has given hundreds of widowed moms the tools they need to create futures they can get excited about.

    In today's conversation, we dig into the biggest reasons people avoid talking about grief, the magic that can be found in post-traumatic growth and how grief doesn't always work in the 5 stages that we've always heard about.

    GET A FREE ACCESS TO KRISTA'S ONLINE WIDOW GRIEF COURSE

    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 GRIEF to 866-482-9559 and we'll make sure you get signed up for free. It's that simple!

    In this podcast interview, you'll learn:

    • Why grief is so much more than just the feeling of bereavement.
    • How traumatic loss gives us the power to redefine our lives, find new meaning, and live more authentically.
    • Why Krista believes that the five stages of grief (DABDA) has become outdated, and what it means to truly and authentically navigate grief and the ways it affects our lives.
    • What Krista would've done differently to prepare for traumatic loss.
    • How to rethink our relationship to money as we navigate grief.
    • What–and what not–to say to people who have lost loved ones.

    Show Notes: Howardbailey.com/413

    Rate & Review the Podcast: RetireWithPurpose.com/review

    Sign Up to Casey's Weekend Reading Email!

    Sifting through the copious amount of conflicting financial advice and retirement information can be daunting - but it doesn't have to be! Each week, Casey makes it super easy. He hand-picks 4 of the most important articles you need to read, that are beneficial to you whether you're at, near, or in retirement! If you want them sent straight to your inbox, sign up by visiting RetireWithPurpose.com/weekend-reading


    412: Making the Most of Middlescence: Why It's Okay to Suck When You Try Something New Jan 05, 2024
    Show notes

    This week's retirement reading is from Vox titled, It's Okay to Suck When You Try Something New. Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/412.

    Show Notes: Howardbailey.com/412

    Rate & Review the Podcast: RetireWithPurpose.com/review

    Sign Up to Casey's Weekend Reading Email!

    Sifting through the copious amount of conflicting financial advice and retirement information can be daunting - but it doesn't have to be! Each week, Casey makes it super easy. He hand-picks 4 of the most important articles you need to read, that are beneficial to you whether you're at, near, or in retirement! If you want them sent straight to your inbox, sign up by visiting RetireWithPurpose.com/weekend-reading


    411: How Charitable Remainder Trusts Can Help Maximize Your Retirement Savings Dec 29, 2023
    Show notes

    This week's retirement reading is from The Street titled, Maximize Retirement Savings With Charitable Remainder Trusts: A 2023 Guide. Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/411.

    Show Notes: Howardbailey.com/411

    Rate & Review the Podcast: RetireWithPurpose.com/review

    Sign Up to Casey's Weekend Reading Email!

    Sifting through the copious amount of conflicting financial advice and retirement information can be daunting - but it doesn't have to be! Each week, Casey makes it super easy. He hand-picks 4 of the most important articles you need to read, that are beneficial to you whether you're at, near, or in retirement! If you want them sent straight to your inbox, sign up by visiting RetireWithPurpose.com/weekend-reading


    410: 7 Principles of Estate Planning and Building a Legacy That Lasts with David York Dec 25, 2023
    Show notes

    Today, I'm speaking with David York. David is an attorney, a CPA, an author, speaker, and managing partner at York, Howell & Guymon. David has over 26 years of estate planning experience and has helped thousands of clients with their estate and tax planning needs, in addition to businesses and nonprofit entities.

    He's the co-creator of the Entrusted Planning™ process and the co-author of two books, including Entrusted: Building a Legacy That Lasts, and we'll be diving into his 7 principles of entrusted planning today.

    In our conversation, David weighs in on several excellent estate planning questions from our Weekend Reading subscribers on trusts, the difference between legacy and estate planning, and the 3 questions children of any family (especially high net worth families) should know the answers to before you leave your wealth behind and much more!

    GET A FREE COPY OF DAVID'S BOOK, ENTRUSTED: BUILDING A LEGACY THAT LASTS

    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 BOOK, that's BOOK to 866-482-9559 for a link to our book request page, complete the form and we will ship you the book for free. It's that simple!

    In this podcast interview, you'll learn:

    • How the baby boomer generation is the largest wealth transfer in history going to half as many people, and why most of them are unprepared.
    • David's definition of estate planning and why it's more of a life plan and not a death plan.
    • How you can add purpose to your estate planning by creating an opportunity transfer instead of a wealth transfer.
    • Defining the 7 principles of Entrusted Planning™ and how investors can identify them.
    • Three questions that children, especially of high net worth families, should know the answers to before transferring wealth to them.
    • Some words of caution for incorporating generosity, foundations and charitable contributions in your estate plan.
    • David's thoughts on AI, ChatGPT, online resources, trust accounts and how to use them for various estate planning needs.

    Show Notes: Howardbailey.com/410

    Rate & Review the Podcast: RetireWithPurpose.com/review

    Sign Up to Casey's Weekend Reading Email!

    Sifting through the copious amount of conflicting financial advice and retirement information can be daunting - but it doesn't have to be! Each week, Casey makes it super easy. He hand-picks 4 of the most important articles you need to read, that are beneficial to you whether you're at, near, or in retirement! If you want them sent straight to your inbox, sign up by visiting RetireWithPurpose.com/weekend-reading


    409: Guaranteed Lifetime Income vs. Taxable Bonds: Which is Better Amidst High Interest Rates? Dec 22, 2023
    Show notes

    This week's retirement reading is from Advisor Perspectives titled, Guaranteed Lifetime Income is a Better Solution than Taxable Bonds. Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/409.

    Show Notes: Howardbailey.com/409

    Rate & Review the Podcast: RetireWithPurpose.com/review

    Sign Up to Casey's Weekend Reading Email!

    Sifting through the copious amount of conflicting financial advice and retirement information can be daunting - but it doesn't have to be! Each week, Casey makes it super easy. He hand-picks 4 of the most important articles you need to read, that are beneficial to you whether you're at, near, or in retirement! If you want them sent straight to your inbox, sign up by visiting RetireWithPurpose.com/weekend-reading


    408: Goal-Setting in Retirement: The Power of Creating a "What I Don't Want" List Dec 15, 2023
    Show notes

    This week's retirement reading is from Mr-Stingy.com titled, The "What I Don't Want" List. Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/408.

    Show Notes: Howardbailey.com/408

    Rate & Review the Podcast: RetireWithPurpose.com/review

    Sign Up to Casey's Weekend Reading Email!

    Sifting through the copious amount of conflicting financial advice and retirement information can be daunting - but it doesn't have to be! Each week, Casey makes it super easy. He hand-picks 4 of the most important articles you need to read, that are beneficial to you whether you're at, near, or in retirement! If you want them sent straight to your inbox, sign up by visiting RetireWithPurpose.com/weekend-reading


    407: A Guide to Better Decision-Making: How to Overcome FOBO, the Fear of Better Options Dec 08, 2023
    Show notes

    This week's retirement reading is from the Darius Foroux blog titled, Understanding and Overcoming FOBO (Fear of Better Options). Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/407.

    Show Notes: Howardbailey.com/407

    Rate & Review the Podcast: RetireWithPurpose.com/review

    Sign Up to Casey's Weekend Reading Email!

    Sifting through the copious amount of conflicting financial advice and retirement information can be daunting - but it doesn't have to be! Each week, Casey makes it super easy. He hand-picks 4 of the most important articles you need to read, that are beneficial to you whether you're at, near, or in retirement! If you want them sent straight to your inbox, sign up by visiting RetireWithPurpose.com/weekend-reading


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