Retire With Purpose - The Retirement Podcast

Casey Weade
  • 5.0 (4)
  • Investing
  • Updated fortnightly

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. 1 day ago

    The Market Concentration Myth: Is Your Portfolio Riskier Than You Think?

    You may own hundreds of stocks, but that doesn't necessarily mean you're diversified. Discover where concentration risk is really hiding and what you can do about it. In this episode, you'll learn: Why owning an S&P 500 index fund may expose you to more concentration risk than you realize. The difference between company concentration and sector concentration Whether international investing actually reduces portfolio risk. Why equal-weight investing is gaining attention in today's market. How to think about highly appreciated individual stock positions before retirement. The one portfolio analysis every retiree should consider. Today's article is from TrendLabs titled, What You Need To Know About the Market Concentration Myth. 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/584 📧 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

  2. 28 Aug

    The 4 Fundamentals of a Thriving Retirement

    Your finances may be ready to enter your second act, but retirement coach Joe Casey explains why the bigger question is whether you've prepared for the life, relationships, health, learning, and fun that come after work. In this episode, you'll learn: Why having more free time doesn't automatically create a fulfilling life How retirement can expose gaps in your social life Why your "best Wednesdays" may matter more than your bucket list How to start experimenting with your future before retirement The questions you and your spouse should be asking before you leave work Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade and Joe Casey provide thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/583 📧 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

  3. 21 Aug

    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

  4. 14 Aug

    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

  5. 10 Aug

    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

  6. 7 Aug

    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

  7. 31 Jul

    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

  8. 24 Jul

    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

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Ratings & Reviews

5
out of 5
4 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.

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