
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 Founder 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.
©2024 HOWARD BAILEY FINANCIAL, INC.
Latest episodes

Apr 18, 2025 • 35min
495: Freedom After 50: The World is Ending… What’s Next?
Les McDaniel, a certified retirement coach and the chief purpose officer at Howard Bailey Financial, joins Casey Weade to tackle profound existential questions about life and contentment. They dive into the impact of letting go of control and embracing uncertainty. Discover how the pursuit of pure contentment outweighs chasing fleeting happiness. The duo shares five thought-provoking questions designed to help listeners cultivate mindfulness and joy in the present, all while navigating life's complexities.

19 snips
Apr 14, 2025 • 1h 9min
494: Beyond the Headlines: How Retirees Can Navigate Investment Risks with Larry Swedroe
In this discussion with Larry Swedroe, former Chief Research Officer at Buckingham Strategic Wealth and author of over 18 books, listeners dive deep into the world of evidence-based investing. Larry emphasizes the power of passive investing and its role in wealth-building. He discusses common emotional biases that lead to poor investment decisions and highlights the importance of a globally diversified portfolio. With insights on risk versus uncertainty, he provides retirees with essential strategies to navigate investment challenges confidently.

9 snips
Apr 11, 2025 • 28min
493: Chaotic Markets: A 4-Point Checklist to Safeguard Your Retirement Savings
Feeling uneasy about market turmoil? Discover a four-point checklist to safeguard your retirement savings. Explore how emotional resilience can guide your financial decisions during chaos. Learn about strategic tax management, including tax loss harvesting and Roth conversions, to capitalize on downturns. The impact of quantum computing on market stability is also discussed. Equip yourself with innovative strategies to enhance your investment strategy and ensure financial security in uncertain times.

8 snips
Apr 4, 2025 • 23min
492: 3 Levels of Retirement Readiness: Where Do You Stand?
How ready are you for retirement? Discover the crucial differences between financial and non-financial readiness. Explore the importance of a solid income strategy and long-term care insurance. Learn how to assess your personal financial situation and prepare for changes ahead. This insightful discussion will guide you through the levels of retirement readiness and provide actionable advice to ensure a smoother transition into this exciting phase of life.

22 snips
Mar 28, 2025 • 32min
491: Freedom After 50: 8 Reasons the Month You Retire Matters
Les McDaniel, a certified retirement coach, joins to discuss the non-financial aspects of retirement timing. They explore the irrational fears that often hold people back from retiring and explain the '3 Cs' of timing: family, health, and social considerations. A fable about a fisherman reimagines the balance between work and leisure, while emphasizing the need for planning a fulfilling post-retirement life. The conversation also touches on the benefits of staggered retirement for couples and the importance of financial guidance in building a robust retirement strategy.

Mar 21, 2025 • 27min
490: Retirement Withdrawal Strategies in Down Markets: Should You Shift Yours?
Market volatility is inevitable. Whether you’re 10 months or 10 years into retirement, it’s vital to ask: is your investment strategy prepared? In this episode, we discuss: Why market volatility is necessary When down markets no longer become an opportunity How to avoid sequence of returns risk 4% withdrawal rule flaws Today's articles are from The Best Interest blog titled, Should I “Reset” Retirement Withdrawals in Bad Markets? and Are You Not Entertained?! 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: RetireWithPurpose.com/490 📧 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

15 snips
Mar 14, 2025 • 27min
489: Freedom After 50: The 4 Myths of Security Keeping You Stuck Today and Fearful of Tomorrow
Les McDaniel, a certified retirement coach and chief purpose officer, challenges conventional beliefs about security. He discusses the pitfalls of the linear success myth, encouraging listeners to embrace flexibility and create their unique paths. Delving into the importance of living in the moment, he highlights the balance between enjoying life now and planning for the future. McDaniel also emphasizes the role of community in fostering well-being, pushing against four common myths about security that often keep people feeling stuck.

12 snips
Mar 10, 2025 • 1h 1min
488: From Accumulating to Spending: 20 Lessons for a Happy & Successful Retirement with Christine Benz
Christine Benz, Director of Personal Finance at Morningstar and a renowned figure in retirement planning, shares her insights on gracefully transitioning into retirement. She emphasizes the need to practice your retirement lifestyle before fully committing, offering tips on sabbaticals and trial runs. Christine introduces innovative spending strategies, challenging the traditional 4% withdrawal rule with a flexible bucket approach. She underscores the importance of social connections and adjusting financial plans based on personal values, all while maintaining joy and purpose in retirement.

Mar 7, 2025 • 27min
487: Should You Pay Off Your Mortgage Before Retirement?
Is it OK for you to bring debt into retirement? More specifically, what about your mortgage? To gain clarity, you must approach this decision from a financial and emotional perspective. In this episode, we discuss: Historical vs. potential future of mortgage rates Why a mortgage can be a valuable asset How to determine your mortgage value Today's article is from A Wealth of Common Sense titled, Should You Pay Off Your Mortgage Before 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: RetireWithPurpose.com/487 📧 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

Feb 28, 2025 • 31min
486: Freedom After 50: How to Talk About the Tough Stuff—Money, Religion & Politics
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: RetireWithPurpose.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
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