Retire With Purpose - The Retirement Podcast

Casey Weade
  • 4.7 (548)
  • INVESTING
  • UPDATED WEEKLY

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.

  1. 2D AGO

    Freedom After 50: Why Retirement Fear Might Be a Sign You're Ready

    What if the fear you feel about retirement isn't a warning sign, but an invitation to step into a more meaningful, self-directed life?  In this episode, you'll learn:  Why hitting your retirement number can increase anxiety The difference between financial independence and fulfillment Three powerful questions to clarify whether it's time to retire How purpose evolves after work — and why fear often shows up first Today's article is from The Purpose Code blog titled, When it Comes to Retirement, Fear is an Invitation. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore why hitting your number can increase anxiety, how financial independence differs from fulfillment, and the key questions that clarify when it's truly time to retire. Show Notes: HowardBailey.com/554 📧 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

    31 min

  2. 6D AGO

    A Step-by-Step Guide to Leverage AI As a Thought Partner & Find Purpose In Retirement with Geoff Woods

    Today, I'm thrilled to finally welcome my friend, Geoff Woods, to the podcast. Geoff is the founder of AI Leadership and The AI-Driven Leadership Collective, the author of The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions, and a leading expert on AI. He previously served as Chief Growth Officer of Jindal Steel & Power, where he played a key role in scaling the company from a $750 million market cap to over $12 billion in just four years. He also co-founded the company behind The ONE Thing, advising organizations with revenue ranging from $10 million to $60 billion. In our conversation, Geoff doesn't just explain what AI does in theory—he'll walk you through a live demonstration of how to use it as a thought partner to help navigate the transition into retirement with greater clarity, confidence, and a renewed sense of purpose. Geoff introduces his CRIT framework for prompting AI more effectively and shares practical strategies for using AI to identify purpose, strengthen daily habits, and avoid common pitfalls.  Geoff also shares his insights on how AI is rapidly shaping the world we live in, addresses concerns about job disruption for the next generation, and explains why learning to use it now will give you an advantage over those who choose to live in fear of it. GET A FREE COPY OF GEOFF'S BOOK, THE AI-DRIVEN LEADER: HARNESSING AI TO MAKE FASTER, SMARTER DECISIONS 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: A simple explanation of AI and how it differs from machine learning and generative AI. Why AI will impact retirees even if it wasn't specifically designed for them. How AI can support better daily decisions around health, habits, and planning. The simplest way to manage privacy settings and reduce concerns about personal data with ChatGPT. Why AI should be treated as a thought partner, not a replacement for your thinking. How the CRIT framework helps generate deeper, more customized responses. Three strategies for transitioning into retirement with more structure and purpose. Why technological change shifts skill value rather than simply eliminating opportunity. Show Notes: HowardBailey.com/553 📧 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

    59 min

  3. MAR 6

    552: By the Numbers: The Anchors of Retirement Confidence, Part 3 — Why Tax Flexibility Matters More Than Tax Savings

    Join us as we continue our "Anchors of Retirement Confidence" series, where we discuss four areas of retirement uncertainty plus strategies to replace your anxiety with clarity and control. In part 3, we explore why the biggest threat to your retirement isn't always market volatility, but the taxes you didn't see coming until it was too late.  In this episode, you'll learn:  How tax concentration quietly limits income flexibility The three core tax buckets every retiree should understand How Roth accounts help create control in an unpredictable tax system Real-life case studies showing why "textbook" strategies don't always work Today's article is from Morningstar titled, 8 Tips to Stop Worrying About Running Out of Money in Retirement. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/552 📧 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

    22 min

  4. FEB 27

    Freedom After 50: Why Retirement Decisions Feel Heavier — and What to Do About It

    What if the confidence you're searching for in retirement decisions hasn't disappeared, but has simply been drowned out by noise?  In this episode, you'll learn:  Why retirement decisions feel more emotionally loaded after 50 The difference between useful information and paralyzing overwhelm How anxiety can be a guide; not a warning sign How to rebuild trust in your intuition and inner voice Today's article is from our own blog titled, Trusting Yourself Again with Yada. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore how retirees can cut through the noise, manage emotional overwhelm, and rebuild confidence in decisions by trusting their intuition and inner voice. Show Notes: HowardBailey.com/551 📧 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

    18 min

  5. FEB 20

    By the Numbers: The Anchors of Retirement Confidence, Part 2 — Building a Plan for the Next Market Crash

    Join us as we continue our "Anchors of Retirement Confidence" series, where we discuss four areas of retirement uncertainty plus strategies to replace your anxiety with clarity and control. In part 2, we explore what really puts retirements at risk during market downturns — and how to build a plan that's designed to withstand them.  In this episode, you'll learn:  Why market volatility isn't the real danger in retirement How a recession buffer creates emotional and financial stability How to separate "living money" from "growth money" Why using time-based buckets can help you gain confidence and clarity Today's article is from Morningstar titled, 8 Tips to Stop Worrying About Running Out of Money in Retirement. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/550 📧 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

    17 min

  6. FEB 13

    Freedom After 50: The Hidden Link Between Your Money Habits and Your Life

    Are your investment habits quietly shaping the way you live — and could a few mindset shifts help you build a more patient, resilient, and fulfilling retirement?  In this episode, you'll learn:  How investing principles translate into life decisions Using stress and uncertainty as tools instead of threats Why margin of safety matters beyond your portfolio The difference between being rich and being truly wealthy What it really takes to prepare for the life side of retirement Today's article is from Vishal Khandelwal's Substack titled, One Long Game. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore how investing habits shape life beyond money—and how mindset shifts can build patience, resilience, and fulfillment in retirement. Show Notes: HowardBailey.com/549 📧 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

    32 min

  7. FEB 9

    Conscious Aging: Finding Meaning, Purpose, and Growth in Retirement with Ron Pevny

    Today, I'm thrilled to welcome Ron Pevny to the podcast. Ron is the founder and director of the Center for Conscious Eldering, a certified Sage-ing Leader with Sage-ing International, and a longtime guide for individuals navigating life's most meaningful transitions. With a master's degree in integral counseling and psychotherapy, Ron has spent decades helping people move through major life passages with intention, clarity, and depth. Ron is also the author of Conscious Living, Conscious Aging: Claiming the Gifts of Elderhood, a powerful guide for those entering the later chapters of life and seeking more than just rest or recreation. His work reframes aging not as decline, but as an opportunity to step into elderhood with purpose—drawing on wisdom, lived experience, and a renewed commitment to growth and contribution. In our conversation, we explore what it truly means to become an elder in today's world. Ron shares the catalysts that led him into this work, including profound health challenges that reshaped his perspective on purpose and calling.  We also discussed the three-phase transition into elderhood and why honoring each stage is essential for discovering what's next after retirement. GET A FREE COPY OF RON PEVNY'S BOOK, CONSCIOUS LIVING, CONSCIOUS AGING: CLAIMING THE GIFTS OF ELDERHOOD 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: What "conscious eldering" really means—and why it matters. Why retirement without purpose often leads to feeling stuck or disengaged. The three phases of transitioning into elderhood. How the neutral zone creates space for clarity and renewal. Why denying aging limits growth and fulfillment. How to identify and express your signature gifts. The role elders play in supporting future generations. Why purpose helps offset physical and emotional challenges later in life. How growth and service remain essential at every age. Show Notes: HowardBailey.com/548 📧 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

    1h 2m

  8. FEB 6

    By the Numbers: The Anchors of Retirement Confidence, Part 1 — Finding Your Sustainable Spending Range

    Join us for our "Anchors of Retirement Confidence" series, where we discuss four areas of retirement uncertainty plus strategies to replace your anxiety with clarity and control. In part 1, we tackle how to create a flexible spending system that adapts with you.  In this episode, you'll learn:  Why safe withdrawal "rules" can create unnecessary stress How to find your personal sustainable spending range The power of small spending adjustments Why most retirees naturally spend less as they age How flexibility becomes your strongest retirement asset Today's article is from Morningstar titled, 8 Tips to Stop Worrying About Running Out of Money in Retirement. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/547 📧 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

    20 min
See All (554)

4.7
out of 5
548 Ratings

About

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.

Information

You Might Also Like