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Retire With Purpose - The Retirement Podcast

Advertise on podcast: Retire With Purpose - The Retirement Podcast

Rating
★★★★★
4.7
from
564 reviews
This podcast has
592 episodes
Language
English
Publisher
Casey Weade
Explicit
No
Date created
2018/08/31
Latest episode
2026/10/16
Average duration
30 min.
Release period
6 days

Description

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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Check latest episodes from Retire With Purpose - The Retirement Podcast podcast


The Retirement Income Strategy That Could Help You Spend More
2026/10/16
New research is challenging the way we think about the 4% rule — and revealing why a smarter retirement income strategy may be less about preserving every dollar and more about confidently funding the life you saved for. In this episode, you'll learn: What the 4% rule gets right — and where it falls short What new research reveals about hybrid income strategies The tradeoff between income, liquidity, inflation protection, and legacy How Social Security, investments, taxes, and guaranteed income can work together Today's article is from Insurance Newsnet titled, A Hybrid Approach Outperforms the 4% Rule, Researchers Find. Listen in as 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/592 📧 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
The Art of Living a More Interesting Life in Retirement
2026/10/12
Today, I'm excited to welcome Dr. Lorraine Besser to the podcast. Lorraine is a philosopher and author of The Art of Interesting: What We Miss in Our Pursuit of the Good Life and How to Cultivate It. Her work explores what it really takes to live a good life and why happiness and meaning may only be part of the equation. Retirement is supposed to be the reward for decades of hard work. You finally have more freedom, fewer obligations, and the opportunity to spend your time however you want. But what happens when the retirement you worked so hard to create still feels flat, repetitive, or like something is missing? In our conversation, Lorraine explains why adding more interesting experiences to our lives can create what she calls psychological richness. We also talk about rediscovering what lights you up, paying attention to what resonates with you, trying new things, and becoming more intentional about creating a retirement that continues to evolve with you. GET A FREE COPY OF LORRAINE'S BOOK, THE ART OF INTERESTING: WHAT WE MISS IN OUR PURSUIT OF THE GOOD LIFE AND HOW TO CULTIVATE IT  In this podcast interview, you'll learn: Why happiness and meaning aren't the only ingredients of a good life. How psychological richness can make retirement feel more engaging and interesting. Why new experiences don't have to be big or time-consuming to change your perspective. How examining what lights you up can help you rediscover parts of yourself you've lost touch with. Why paying attention to feelings of resonance and dread can help guide how you spend your time. How to know when a new activity deserves more time and when it's better to move on. Show Notes: HowardBailey.com/591 📧 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
The ABCs of a Meaningful Retirement
2026/10/09
What if retirement isn't the end of your story, but the beginning of one of its most meaningful chapters? Best-selling author Bruce Feiler explores how to rediscover purpose, identity, connection, and meaning when life — and retirement — takes an unexpected turn. In this episode, you'll learn: Bruce's ABCs of Meaning: Agency, Belonging, and Cause Why retirement can feel like a major "plot twist" How to redefine your identity when your career no longer defines your days How to intentionally create the next chapter of your life A simple exercise you can use to create more meaning starting today Listen in as 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/590 📧 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
The Hidden Tax Drag That Could Cost You Millions
2026/10/02
The market's return is only part of the story. Find out how taxes can quietly erode your retirement wealth and the planning strategies that can help you keep more of what you've worked so hard to build. In this episode, you'll learn: Why tax drag can cost far more than the tax bill you see How asset location can improve your after-tax returns Why the timing of a sale can make a meaningful difference How Roth conversions and capital-gain harvesting can fit into a retirement tax strategy The KEEP framework for thinking about taxes throughout retirement Today's article is from SSRN titled, Uncle Sam's Cut: A Century of the Federal Tax Drag on US Equity Returns. Listen in as 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/589 📧 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
The 90-10 Rule: What Really Matters After You Retire
2026/09/25
What if the thing you spend 90% of your time planning for before retirement becomes the thing you think about least once you get there? Fritz Gilbert of The Retirement Manifesto joins us to explore the 90-10 rule and why preparing for a fulfilling retirement requires just as much thought about your life as your money. In this episode, you'll learn: How to start planning the non-financial side of retirement Why analytical people can get stuck in endless "what-if" scenarios How to prepare for boredom, isolation, and loss of identity The "spokes" that help create balance in your life How to stress-test your life — not just your retirement portfolio Listen in as CEO of Howard Bailey Financial, Casey Weade and Fritz Gilbert provide thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/588 📧 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
Why Age-Gap Couples Need a Different Retirement Plan
2026/09/18
If you and your spouse are several years apart in age — or simply plan to retire at different times — this episode reveals the financial and relationship challenges most couples never anticipate and how to prepare for them. Listen for insight on: Why retirement comes in three distinct phases How to create a "retirement operating agreement" as a couple Medicare and healthcare planning pitfalls for age-gap couples Social Security strategies that could impact lifetime income Tax planning opportunities before both spouses retire Practical ways to build a retirement plan that works through every stage Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/587 📧 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
Why Social Connections Are Essential for a Healthy Retirement
2026/09/14
Today, I'm excited to welcome Ken Stern to the podcast. Ken is the founder and chair of the Longevity Project, host of Century Lives from the Stanford Center on Longevity, former CEO of NPR, and author of Healthy to 100: How Strong Social Ties Lead to Long Lives. His research explores an aspect of retirement planning that rarely gets enough attention: our social health. Far too many people spend years wondering whether they've saved enough to retire, but very few think about whether they are socially ready to retire. Work provides much more than a paycheck. It provides routines, relationships, purpose, and regular interaction with other people, but when that disappears, retirement can become far more isolating than most people anticipate. In our conversation, Ken explains why strong social connections are critical to our health and longevity, how to replace the relationships and routines we lose when we leave the workforce, and why we should approach retirement with the same intentionality we brought to our careers. GET A FREE COPY OF KEN'S BOOK,  HEALTHY TO 100: HOW STRONG SOCIAL TIES LEAD TO LONG LIVES 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 being financially ready for retirement doesn't necessarily mean you're socially ready. How leaving the workforce can unexpectedly disrupt your relationships, routines, and sense of purpose. Why strong social connections can play such an important role in healthy aging and longevity. What longer-lived countries can teach us about work, learning, volunteering, and intergenerational connection. How place planning and proximity can make it easier to build meaningful relationships in retirement. Why your social connection plan should begin long before your final day of work. Show Notes: HowardBailey.com/586 📧 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
The U-Curve of Happiness: Why Life Gets Better with Age
2026/09/11
What if getting older doesn't mean losing happiness, but gaining more of it? Author Don Ezra explores the surprising science behind the U-curve of happiness and why perspective, purpose, gratitude, and letting go of perfection can make the years ahead some of your best. In this episode, you'll learn: Why happiness often dips in midlife and rises again later in life How dopamine influences our desire for "more" The connection between purpose and life satisfaction A simple exercise for cultivating gratitude and greater life satisfaction Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade and Don Ezra provide thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/585 📧 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
The Market Concentration Myth: Is Your Portfolio Riskier Than You Think?
2026/09/04
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
The 4 Fundamentals of a Thriving Retirement
2026/08/28
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
Should You Stop Saving for Retirement? The Surprising Truth
2026/08/21
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
Are You Socially Fit for Retirement?
2026/08/14
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
Die With Zero: Rethinking Wealth, Retirement, and Fulfillment with Bill Perkins
2026/08/10
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
Will Social Security Really Run Out? What Retirees Need to Know
2026/08/07
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
The Fear of Running Out vs. The Fear of Missing Out
2026/07/31
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

Podcast reviews

Read Retire With Purpose - The Retirement Podcast podcast reviews


4.7 out of 5
564 reviews
★★★★★
Jim@Mystic 2026/10/14
The Art of Interesting
I really enjoyed Casey’s interview with Dr Lorraine Besser. Casey is a great host and knows just the right questions to ask. I’ve been retired from ...
★★★★★
Ballgame1520 2026/10/14
Great information
I’ve been listening to these podcast for the last several months since I’m nearing retirement. I feel like I have a pretty good handle on the financia...
★★★★★
Guille_Arg 2026/10/13
Excellent guide for anyone navigating this stage of life
Since I retired, I have been listening to the Retire with Purpose podcast. It has provided me with valuable insights for building a successful retirem...
★★★★☆
GoingToRetire 2026/10/13
Retire Well
Previously gave this 5 stars, but the book offers seem to be a scam to get reviews. I filled out the necessary info on the day the podcasts dropped f...
★★★★★
AZ Marc 2026/08/15
Listen every week
Casey’s interviewing skills are super as is his selection of guests. Highly recommend this podcast for anyone that ever thinks they may retire someday...
★★★★★
irbdave25 2026/08/10
Casey is one of my AI truth tellers
I’ve built an AI tool to help my team with Investment & Retirement Education and Casey is one of the advisors I’ve included. Always provides well thou...
★★★★★
Tgdg5580 2026/08/10
Die with zero
Bill Perkins is the man. I see way too many friends and relatives that have a major issue with spending their money in retirement. I think Bill has ...
★★★★★
Dow Jane 2026/07/02
Both financial & non financial advice
This podcast has a great blend of financial and nonfinancial topics and both are important.
★★★★★
CWTIV 2026/06/27
Helpful!
Excellent insight into retirement planning.
★★★★★
cnujjf 2026/06/25
Rethinking the 4% rule…
Excellent podcast!
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