

Retire With Purpose - The Retirement Podcast
Casey Weade
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.
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.
Episodes
Mentioned books

6 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: Howardbailey.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: 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

Feb 21, 2025 • 26min
485: Top 5 Retiree Regrets and How to Avoid Them
Marshall Johnson, a certified financial planner, shares invaluable insights into common retiree regrets and strategies to avoid them. He emphasizes the importance of saving adequately, revealing that many retirees wish they had saved more. The conversation also covers the significance of Social Security decisions and the challenges of managing debt in retirement. Furthermore, they discuss the regrets of early retirement and stress the need for health awareness and financial readiness. Overall, practical advice is provided to help listeners navigate their retirement planning effectively.

Feb 14, 2025 • 23min
484: Freedom After 50: Fearless Freedom – Unlocking Radical Resilience for Life's Next Chapter
Les McDaniel, a certified retirement coach and chief purpose officer at Howard Bailey, explores spirituality’s pivotal role in achieving a meaningful retirement. He discusses how faith can guide individuals through life's transitions and alleviate post-50 fears. The conversation encompasses embracing diverse perspectives for deeper connections, overcoming isolation, and fostering community. McDaniel also emphasizes the journey toward understanding life's complexities, drawing parallels from various philosophies to cultivate resilience and purpose in the golden years.

8 snips
Feb 10, 2025 • 1h 3min
483: The Future of Tax Rates: How to Keep More of Your Money and Pay Less Taxes with Ed Slott
Ed Slott, a CPA and best-selling author renowned for his expertise in retirement distribution, shares valuable insights on managing taxes in retirement. He discusses strategies such as Roth conversions and highlights common misconceptions about tax liabilities. Slott emphasizes the importance of proactive tax planning and suggests that now is the time to take advantage of historically low tax rates. He also warns that IRAs might not be the best assets to inherit, prompting thoughtful estate planning.

Feb 7, 2025 • 31min
482: Freedom After 50: How to Build a Legacy That Will Outlast You—Exploring the Wise Wealth Matrix - Part 4
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

13 snips
Jan 31, 2025 • 28min
481: Comparing 4 Flexible Income Strategies for Retirement
Discover the evolution of retirement income strategies and their adaptation to financial challenges. Explore four flexible income approaches that cater to individual needs, departing from traditional methods like the 4% rule. Learn how market conditions and inflation affect withdrawal strategies, ensuring financial stability. Plus, delve into the Required Minimum Distribution (RMD) for retirees and its implications. Equip yourself with insights to align your spending with market performance for a secure retirement.

Jan 24, 2025 • 33min
480: Freedom After 50: The Shadow Side of Wealth - Exploring the Wise Wealth Matrix - Part 3
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

8 snips
Jan 17, 2025 • 23min
479: Our 2025 Market Predictions
Financial experts dive into predictions for the stock market in 2025, reflecting on past forecasts and the current market landscape. They humorously weigh optimism against skepticism, discussing the surprise absence of negative predictions. The conversation shifts to the impact of tech advancements and the importance of diversification in an evolving market. Listeners can expect insights on asset performance, particularly the rise of small caps and international stocks, alongside an engaging upcoming webinar on economic trends.


