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Retire With Purpose – The Retirement Podcast

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.

Latest Episodes:

596: Rethinking What It Means to Be Wealthy in Retirement with Jacob Schroeder Nov 09, 2026

Show notes

Today, I'm excited to welcome Jacob Schroeder to the podcast. Jacob is a financial writer, content strategist, and creator of The Root of All blog, where he explores the relationship between money, meaning, psychology, and living a good life. His writing challenges the conventional ways we think about wealth and what it really means to be financially successful.

After spending decades working hard, saving, and building wealth, retirement is supposed to be the time when you finally get to enjoy it. But having enough money to retire and actually feeling like you have enough are two very different things. And even when you've achieved financial independence, there's no guarantee that the happiness and fulfillment you've been working toward will follow.

In our conversation, Jacob shares why the way we use our wealth matters just as much as how much we've accumulated. We also explore the emotional challenges of transitioning from saving to spending, why our relationship with money continues to evolve throughout retirement, and what it really takes to build a life that feels rich beyond the numbers in your portfolio.

In this podcast interview, you'll learn:

Why reaching your retirement savings goal doesn't always create a sense of financial security.
How to recognize when you're accumulating wealth without a meaningful purpose behind it.
Why having more money can magnify who you already are rather than make you happier.
How to give yourself permission to spend on experiences without jeopardizing your financial future.
The difference between résumé virtues and eulogy virtues and how they shape your financial decisions.
Why creating meaningful relationships and feeling like you matter are essential to a fulfilling retirement.

Show Notes: HowardBailey.com/596

📧 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

595: 4 Retirement "Electives" That Can Bring More Purpose to Your Life Nov 06, 2026

Show notes

Retirement opens the door to new possibilities, but how do you decide what deserves your time, energy, and attention? Retirement coach Joe Casey explores the concept of retirement "electives" and how they can help you build a life filled with purpose, curiosity, and connection.

In this episode, you'll learn:

How to find the right amount of volunteering in retirement
When work adds purpose — and when it simply fills your calendar
Why becoming a beginner again can be so difficult
Why "tiny experiments" can help you discover what you enjoy
A simple 30-day challenge to help you find your next elective

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/595

📧 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

594: 4 Retirement Risks Your Financial Plan May Be Missing Oct 30, 2026

Show notes

Your retirement plan has to do more than survive market volatility; it has to keep working through a long life, changing health, unexpected costs and the possibility that you may one day struggle to make the decisions it requires.

In this episode, you'll learn:

Why longevity risk goes far beyond simply "not running out of money"
How early market losses can affect your retirement income
The hidden trade-off behind dynamic spending strategies
Why health and long-term care costs can reshape your plan
How cognitive decline can create a financial risk years before a diagnosis
Practical ways to simplify and strengthen your retirement plan

Today's article is from the Financial Planning Association titled, Beyond Sequence of Returns: The Four Risks to Retirement Security. 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/594

📧 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

593: The Secret to a More Connected Retirement Oct 23, 2026

Show notes

What if one of the keys to a happier, more meaningful retirement isn't doing more, but becoming more curious about the people and world around you?

In this episode, psychology professor Dr. March Schulz explores:

Why curiosity and attention are essential to deeper relationships
Why talking to strangers can boost your happiness
How to bring "fresh eyes" to a decades-long marriage or friendship
A 7-day curiosity challenge you can try yourself

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/593

📧 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

592: The Retirement Income Strategy That Could Help You Spend More Oct 16, 2026

Show notes

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

591: The Art of Living a More Interesting Life in Retirement Oct 12, 2026

Show notes

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

590: The ABCs of a Meaningful Retirement Oct 09, 2026

Show notes

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

589: The Hidden Tax Drag That Could Cost You Millions Oct 02, 2026

Show notes

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

588: The 90-10 Rule: What Really Matters After You Retire Sep 25, 2026

Show notes

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

587: Why Age-Gap Couples Need a Different Retirement Plan Sep 18, 2026

Show notes

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

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