488: From Accumulating to Spending: 20 Lessons for a Happy & Successful Retirement with Christine Benz
Retire With Purpose - The Retirement Podcast
Release Date: 03/10/2025
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: ...
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513: The One Big Beautiful Bill Act: What It Really Means for Your Retirement Taxes
Retire With Purpose - The Retirement Podcast
What does the “One Big Beautiful Bill Act” mean for your retirement? Find out how the latest tax legislation—from permanent TCJA extensions to surprising changes in charitable giving, Social Security taxation, 529 plan use, and more—could affect your tax strategy for years to come. In this episode, we discuss: Updated inflation adjustments Capital gains nuance Enhanced standard deduction for seniors Social Security misconceptions New “below-the-line" deductions Today's article is from the Kitces.com blog titled, . Listen in as Founder and CEO of , Casey...
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512: Freedom After 50: The Sunk Cost Fallacies Sinking Your Future Vision
Retire With Purpose - The Retirement Podcast
Have you ever held on to something just because you’ve “put too much into it to let it go”? Many of us fall into the sunk cost fallacy trap—the quiet force that keeps us tied to the past. Whether it’s a house full of memories that no longer fits your lifestyle, a career that defined your identity for decades, or a friendship that’s no longer life-giving, this conversation will help you identify what might be holding you back—and, more importantly, how to move forward. In this episode, we discuss: How sunk costs can go far beyond money Why letting go = gaining...
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511: Sequence Risk Meets RMDs: The Retirement Trap No One Talks About
Retire With Purpose - The Retirement Podcast
Are your Required Minimum Distributions (RMDs) setting you up for failure? Find out how sequence of returns risk combines with RMD rules to create a hidden hazard—and how smart planning, asset allocation, and timely Roth conversions can help you sidestep it. In this episode, we discuss: Why RMDs are self-regulating The RMD tax chain reaction Why withdrawal timing and asset allocation matters The power of Roth conversions Today's article is from the Best Interest blog titled, Listen in as Founder and CEO of , Casey Weade, breaks down the article and...
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510: Managing Investment Risk When You've Already Won The Game with William Bernstein
Retire With Purpose - The Retirement Podcast
Today, I'm speaking with William Bernstein. Bill is a renowned investment advisor, author, and retired neurologist. He's the co-founder of Efficient Frontier Advisors, a leading voice in the world of personal finance, and the author of several acclaimed books, including The Four Pillars of Investing, The Investor's Manifesto, and The Intelligent Asset Allocator. With a unique background in neurology and finance, Bill brings a practical and evidence-based perspective to long-term investing, risk management, and financial behavior—especially for retirees and those nearing retirement....
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509: Freedom After 50: 7 Practices to Help You Stop Hiding and Start Growing
Retire With Purpose - The Retirement Podcast
What if your greatest growth in retirement didn’t come from doing more—but from finally sitting with who you are? Throughout this discussion, we explore the concept of the “shadow self”—the parts of yourself that you may avoid, hide, or ignore—and how bringing light to these areas can lead to true peace and deeper connection in the second half of life. In this episode, we discuss: How unresolved emotional patterns can impact health, relationships, and joy Why it’s important to take inventory of the roles you’ve been praised for How to leverage retirement as a...
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508: More Control, Less Surprise: A Real Retirement Tax Wake-Up Call
Retire With Purpose - The Retirement Podcast
What if you did everything “right” in retirement, but were still left surprised? That’s exactly what happened to Fritz Gilbert, one of our favorite past podcast guests. In this episode, we unpack his recent article, “My Biggest Surprise in Retirement,” and explore why his carefully planned Roth conversions didn’t make the impact he expected. This conversation is for anyone who wants to stay in the driver’s seat—no surprises, no backseat driving from Uncle Sam—just thoughtful, purpose-driven planning. In this episode, we discuss: Why Roth conversions may...
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507: Freedom After 50: You’re Not Looking for Advice—You’re Looking for Alignment, Part 2
Retire With Purpose - The Retirement Podcast
In this powerful follow-up episode, Casey Weade and Certified Retirement Coach Les McDaniel return to explore the deeper question behind advice-seeking: Are you truly looking for direction, or for alignment with your values? Drawing from real-life coaching stories, they unpack six invitations to help you pause, reflect, and realign your financial decisions with your life’s purpose. In this episode, we discuss: How to ask better questions Ways to elevate your emotional awareness How to separate valuable advice from projection-based advice Today's article is from our very...
info_outlineToday, I'm very excited to welcome Christine Benz back to the podcast. Christine is the Director of Personal Finance and Retirement Planning at Morningstar. She has become a trusted voice in the industry and has been recognized as one of Barron’s Top 100 Most Influential Women in Finance and one of the Ten Most Influential Women in Wealth Management. She’s also the co-host of The Long View and How to Retire podcasts where she brings a wealth of expertise and real-world insight to every conversation.
In her newest book, How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement, Christine draws from her “Me Search” project and lays out practical strategies that help you transition from a lifetime of accumulation to a lifestyle rich in purpose and meaningful spending.
In our conversation, Christine outlines the importance of practicing your retirement lifestyle before you fully commit. She explains how experimenting with sabbaticals and trial runs can help you strike the right balance between structure and flexibility. We discussed the movement of rethinking the traditional 4% rule with a bucket strategy—so you can build confidence in managing your cash flow and spending.
GET FREE ACCESS TO CHRISTINE’S BOOK TITLED, HOW TO RETIRE: 20 LESSONS FOR A HAPPY, SUCCESSFUL, AND WEALTHY RETIREMENT
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- Step 1.) Subscribe to the podcast and leave an honest rating & review over on iTunes.
- Step 2.) Text the word BOOK to 866-599-4491 and we’ll make sure you get signed up for free. It’s that simple!
In this podcast interview, you’ll learn:
- Why testing your retirement lifestyle before you retire can save you stress later.
- How a balanced mix of routine and flexibility fuels a fulfilling daily life.
- Why rethinking the 4% rule with a bucket strategy builds spending confidence.
- How proactive long-term care planning can shield you from future costs.
- Why syncing your spending with your portfolio and other income sources reduces fear and anxiety.
- The smart steps women can take to overcome unique retirement challenges.
Show Notes: Howardbailey.com/488
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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