Retire With Purpose - The Retirement Podcast

Hosted by Casey Weade

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581

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Aug 2026

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About the show

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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August 21, 2026Episode 58227 min

582: Should You Stop Saving for Retirement? The Surprising Truth

Could doing everything "right" with your retirement savings actually be limiting your financial freedom? As part of our "By the Numbers" series, in this episode, you'll learn: Why "max out your 401(k)" isn't always the right answer The overlooked value of liquidity and accessible cash When you may have already saved enough for retirement How taxes can quietly become one of retirement's biggest expenses Why your retirement plan should support your life; not the other way around Today's article is from the Use Your Wealth blog titled You Should Probably Stop Saving for 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/582 📧 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

August 14, 2026Episode 58132 min

581: Are You Socially Fit for Retirement?

What if one of the biggest keys to a healthy, meaningful retirement has nothing to do with money? Author and psychology professor Dr. Marc Schulz reveals why your relationships, social connections and "social fitness" may play a surprisingly important role in how well you age — and how you can strengthen them before and during retirement. In this episode, you'll learn: How retirement can disrupt your social network Ways introverts and extroverts can approach social fitness differently The "2 a.m. friend" test for evaluating your relationships How couples can navigate different social needs in retirement Dr. Schulz's practical 30-day social fitness challenge Listen in as Founder and CEO of Howard Bailey Financial , Casey Weade and Dr. Marc Schulz provide thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/581 📧 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

August 10, 2026Episode 58057 min

580: Die With Zero: Rethinking Wealth, Retirement, and Fulfillment with Bill Perkins

Today, I'm excited to welcome Bill Perkins to the podcast. Bill is an entrepreneur, hedge fund manager, investor, and bestselling author of Die With Zero: Getting All You Can from Your Money and Your Life. Throughout his career, he's challenged one of the most common assumptions about wealth: that accumulating more money should always be the ultimate goal. Instead, Bill encourages people to think differently about how they use their time, health, and financial resources to create a more fulfilling life. Far too many retirees spend decades building wealth only to discover that saving money is much easier than confidently spending it. Bill believes retirement isn't about maximizing your account balance; it's about maximizing your experiences while you still have the health and time to enjoy them. That means being intentional about when you travel, when you create memories with loved ones, and even when you pass wealth on to the next generation. In our conversation, Bill explains why money should always serve your life instead of becoming the goal itself, how "time bucketing" can help prioritize life's most meaningful experiences, why health may be your most valuable retirement asset, and how intentionally spending, giving, and creating memories can ultimately lead to a richer and more purposeful retirement. GET A FREE COPY OF BILL'S BOOK, DIE WITH ZERO: GETTING ALL YOU CAN FROM YOUR MONEY AND YOUR LIFE Here's how: Just 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: Why maximizing fulfillment—not maximizing wealth—should become your retirement goal. How time bucketing helps you prioritize experiences before opportunities disappear. Why your health becomes one of your most valuable retirement resources. How memory dividends can create lasting returns long after an experience ends. Why intentionally giving wealth during your lifetime may create a greater legacy than leaving an inheritance after you're gone. How designing simple systems can help you live more intentionally instead of on autopilot. Show Notes: HowardBailey.com/580 📧 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

August 7, 2026Episode 57918 min

579: Will Social Security Really Run Out? What Retirees Need to Know

Headlines say Social Security is going bankrupt, but the real story is far more nuanced, and understanding it could help you make smarter retirement decisions before it's too late. In this episode, you'll learn: What the latest 2026 Trustee Report reveals Why retirees could still receive benefits, even without Congressional action How AI, longevity, and future productivity could change the outlook The most likely solutions Congress could pursue How to stress test your retirement income plan for multiple Social Security scenarios Today's article is from the Center for Retirement Research at Boston College titled, Social Security's Financial Outlook: The 2026 Update in Perspective. 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/579 📧 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

July 31, 2026Episode 57816 min

578: The Fear of Running Out vs. The Fear of Missing Out

When it comes to a confident retirement, what if the biggest risk isn't running out of money, but waiting too long to enjoy it? As part of our "Freedom After 50" series, author Mike Drak explores: Why so many retirees struggle emotionally with spending How retirement spending naturally changes over time The difference between spending on things vs. meaningful experiences How fear of future healthcare costs can hold you back today Practical ways to spend with greater confidence and fewer regrets Listen in as Founder and CEO of Howard Bailey Financial , Casey Weade and Mike Drak provide thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/578 📧 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

July 24, 2026Episode 57723 min

577: Long-Term Investing: What Many Retirees Get Wrong

Everyone says to "invest for the long term," but what does that actually mean when you're approaching or living in retirement? As part of our "By the Numbers" series, in this episode, you'll learn: Why "long term" means much more than simply waiting How retirement changes the way you should think about investing The psychological cost of staying invested during market downturns Why buying and forgetting isn't a successful investment strategy How to know if you're taking more risk than you actually need Today's article is from the Safal Niveshak blog titled What I Mean When I Say 'Long Term' 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/577 📧 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

July 17, 2026Episode 57621 min

576: The Retirement Exercise That Changes Everything

What if one simple exercise could help you uncover what truly brings you joy, clarify your purpose, and shape a more meaningful retirement? As part of our "Freedom After 50" series, author Jet Vertz shares: How the "Lifeline Exercise" helps uncover defining moments in your life Why your happiest moments often reveal your deepest values How to identify the strengths, passions, and experiences that should shape your retirement Why honesty with yourself is essential to creating a retirement filled with meaning instead of simply staying busy A simple reflection exercise you can do on your own, or even with your spouse Listen in as Founder and CEO of Howard Bailey Financial , Casey Weade and Jet Vertz provide thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/576 📧 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

July 13, 2026Episode 5751 hr 2 min

575: Why Your Health Is Your Greatest Retirement Asset with Dr. Phil Pearlman

Today, I'm excited to welcome Dr. Phil Pearlman to the podcast. Phil is the founder of the Pearl Institute, a clinical psychologist, former financial executive, and one of the leading voices exploring the intersection of health, behavioral psychology, and long-term performance. Through his writing, coaching, and research, he helps people build healthier lives by focusing on sustainable habits, emotional resilience, and purposeful daily decisions. After years of success in finance, Phil experienced his own health transformation that completely changed how he thinks about performance, longevity, and fulfillment. Today, he believes one of the biggest blind spots in retirement planning isn't your portfolio, it's your health. Because no matter how well you've prepared financially, it's difficult to enjoy the retirement you've worked so hard to build without the physical and mental capacity to fully experience it. In our conversation, Phil shares why health and wealth follow many of the same behavioral principles, how our relationship with food and money is driven by the same psychological forces, and why improving your health may be the greatest investment you can make in your future. In this podcast interview, you'll learn: Why your health may be the most overlooked risk to a successful retirement. How our relationship with food and money is shaped by the same psychological biases. Why lasting health habits are built through identity, not willpower. How improving your metabolic health can lead to better decisions, focus, and resilience. Why comparing yourself to your past self and nobody else creates the greatest long-term progress. The simple daily habits Phil believes deliver the biggest return for your future health. Show Notes: HowardBailey.com/575 📧 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

July 10, 2026Episode 57432 min

574: Why Most Stocks Fail (And What Retirees Need to Know)

Your greatest investment risk may not be missing the market, but relying on your ability to identify the small handful of stocks that become the next big winners. As part of our "By the Numbers" series, topics covered in this episode include: Why most individual stocks fail to outperform the market What increasing market concentration means for retirees Why average returns can create dangerous expectations How to think about risk, diversification, and income in retirement The surprising case for Treasury bills and liquidity Listen in as Founder and CEO of Howard Bailey Financial , Casey Weade and Bruce Feiler provide thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/574 📧 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

July 3, 2026Episode 57319 min

573: The Life Transition Every Retiree Must Learn to Master

Retirement isn't just about leaving your career; it's about learning how to navigate one of life's biggest transitions with confidence and resilience. As part of our "Freedom After 50" series, best-selling author Bruce Feiler shares why the most fulfilling retirements come from embracing change instead of resisting it. Topics covered in this episode: Why retirement is often a "lifequake," not just a life event The three phases everyone experiences during major life transitions How to avoid getting stuck after retirement How couples can navigate retirement transitions together A simple exercise to identify where you are and what you need most Listen in as Founder and CEO of Howard Bailey Financial , Casey Weade and Bruce Feiler provide thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/573 📧 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