502: Freedom After 50: The Hidden Cost of Delayed Gratification in Retirement
Retire With Purpose - The Retirement Podcast
Release Date: 05/30/2025
523: Freedom After 50: Beyond the Pyramid—Rethinking Happiness in Retirement
Retire With Purpose - The Retirement Podcast
Many of us spend decades climbing Maslow’s pyramid — seeking security, comfort, and experiences — only to realize that the top is where true joy lives. Join us as we explore the “Happiness Hierarchy” and why lasting fulfillment comes not from what you buy or where you travel, but from who you become. In this episode, we discuss: How to shift from “having enough” to “becoming more” Why Maslow’s hierarchy is often misunderstood The three levels of happiness Why reflection unlocks the freedom to become Today's article is from Jordan Grumet blog titled ....
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522: The Six Pillars to Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 2
Retire With Purpose - The Retirement Podcast
Living longer is one thing. Living well is another. In Part 2 of my conversation with Dr. Bobby Dubois, we unpack the final three pillars of his blueprint for longevity: mind-body harmony, heat & cold exposure, and social relationships. Dr. Bobby explains why practices like meditation, breathwork, and even walking in nature can calm the brain and lower anxiety. We also explore the science-backed benefits of sauna and cold plunging—and what’s hype versus what’s real. Finally, we uncover why social connection is the single strongest predictor of living a long, healthy, and fulfilling...
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521: 5 Timeless Proverbs for a Wise and Wealthy Retirement
Retire With Purpose - The Retirement Podcast
What can ancient wisdom teach us about modern retirement? From budgeting with freedom to preparing for life’s surprises, tackling debt, planning wisely, and redefining generosity in retirement, insights of the past can show how true wealth goes beyond dollars. In this episode, we discuss: The importance of having a budget, even in retirement Emergency fund: How much do you need? Debt and dependence Generosity in retirement: Stewardship, legacy planning, and the “Die with Zero” philosophy Today's article is from our very own blog post titled, Listen in as Founder and...
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520: The Six Pillars of Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 1
Retire With Purpose - The Retirement Podcast
Today, I’m speaking with Dr. Bobby Dubois. Dr. Bobby is a Harvard-educated physician, Board-Certified in Internal Medicine with over 25 years of experience. He’s an author, entrepreneur, wellness doctor, and Ironman Triathlete. Most recently, he led a health policy research organization in Washington, D.C. (National Pharmaceutical Council) as its Chief Science Officer and Executive Vice President. Prior to that, he served as the Chief Medical Officer of Cerner Life Sciences and co-founded Proto Care Sciences. He's the host of the Live Long and Well podcast and has made it his mission to...
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519: Freedom After 50: How to Break Free from Your Old Story and Shape Wisdom That Lasts
Retire With Purpose - The Retirement Podcast
Retirement isn’t the end — it’s your greatest opening. Join us as we explore how to break free from old stories, embrace wisdom, and turn life’s challenges into a legacy of meaning and impact. In this episode, we discuss: Why lifequakes = growth Fluid vs. crystallized intelligence How to redefine success in retirement The role of curiosity and engagement Today's article is from our very own blog post titled, . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore how to transform lifequakes into growth, embrace wisdom, and redefine...
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518: Beyond Investment Risk: Why Income Risk Could Change Your Retirement Plan
Retire With Purpose - The Retirement Podcast
Most financial plans focus on how your investments perform, but what about the risks to your income along the way? Join us as we unpack groundbreaking research that shows why traditional retirement calculators and rules of thumb may be leaving you exposed. In this episode, we discuss: Traditional planning gaps The three types of income risk Risk Capacity vs. Need vs. Attitude Retirement “buffering” The Retirement Red Zone Today's article is from Morningstar, titled . Listen in as Founder and CEO of , Casey Weade, breaks down the article and...
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517: Freedom After 50: The Need for Next—Finding Meaning Beyond Milestones
Retire With Purpose - The Retirement Podcast
Why do so many retirees struggle to find fulfillment after leaving the workforce, and how do they break free from the traps of status, constant pleasure-seeking, and busywork? Together, we unpack practical strategies for moving beyond milestones to craft a retirement rich in purpose, connection, and legacy. In this episode, we discuss: The “need for next” mindset Five common non-financial retirement traps The “good enough” principle How to avoid pleasure-only living and flow with life’s seasons Today's article is from Mr-Stingy.com titled . Listen in as Founder and CEO...
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516: Mind the Inflation Gap: Why Forecasts Fail and How to Hedge Smart
Retire With Purpose - The Retirement Podcast
Inflation is unpredictable—and it doesn’t care what the experts think. Join us as we explore why traditional forecasting fails, how real assets like real estate and commodities can act as powerful inflation hedges, and whether Bitcoin truly deserves its "digital gold" title. In this episode, we discuss: Consumer vs. professional inflation expectations What it means to leverage “Real Assets” as a hedge Why equities still matter The role of diversification A planning framework to help safeguard against inflation Today's article is from the CFA...
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515: The Soul of Wealth: Bridging the Gap Between Money and Happiness with Daniel Crosby, PhD
Retire With Purpose - The Retirement Podcast
Today’s guest is Dr. Daniel Crosby, a leading psychologist and behavioral finance expert who helps individuals and organizations understand how our thoughts, emotions, and behaviors intersect with the markets—and ultimately, our sense of purpose. He serves as Chief Behavioral Officer at Orion Advisor Solutions and is the bestselling author of The Soul of Wealth: 50 Reflections on Money and Meaning. He’s been recognized by AARP and Monster.com as a top financial thinker and is the host of the Standard Deviations podcast. Daniel was on the podcast back in 2020, and I’m thrilled to...
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514: Freedom After 50: You Planned Wisely—But Is Your Money Aligned with What Matters Most?
Retire With Purpose - The Retirement Podcast
What if true wealth isn't just about how much you’ve saved, but how wisely you’re living? Join us as we explore the WiseWealth Matrix, a tool built on six life “currencies” that go far beyond money. In this episode, we discuss: The WiseWealth Framework Wealth vs. Wisdom currencies The 4 zones of the Matrix And, an exciting announcement! Today's article is from our very own blog post titled . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore how to live wisely, not just save wisely. Show Notes: ...
info_outlineYou're encouraged to save, delay gratification, and be disciplined with your spending—but what happens when that mindset becomes a roadblock in retirement?
In this episode, we discuss:
- The psychology of postponement
- How to unwind a lifetime of discipline
- The “Joy Budget” concept
- Tools to reframe spending
Today's article is from The Wall Street Journal titled, The Downside of Delayed Gratification. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to discuss how to shift from saving mode to truly living in your retirement years.
Show Notes: Howardbailey.com/502
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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