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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:

576: The Retirement Exercise That Changes Everything Jul 17, 2026

Show notes

What if one simple exercise could help you uncover what truly brings you joy, clarify your purpose, and shape a more meaningful retirement?

As part of our "Freedom After 50" series, author Jet Vertz shares:

How the "Lifeline Exercise" helps uncover defining moments in your life
Why your happiest moments often reveal your deepest values
How to identify the strengths, passions, and experiences that should shape your retirement
Why honesty with yourself is essential to creating a retirement filled with meaning instead of simply staying busy
A simple reflection exercise you can do on your own, or even with your spouse

Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade and Jet Vertz provide thoughtful insights and advice on how it applies to your unique financial situation.

Show Notes: HowardBailey.com/576

📧 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

575: Why Your Health Is Your Greatest Retirement Asset with Dr. Phil Pearlman Jul 13, 2026

Show notes

Today, I'm excited to welcome Dr. Phil Pearlman to the podcast. Phil is the founder of the Pearl Institute, a clinical psychologist, former financial executive, and one of the leading voices exploring the intersection of health, behavioral psychology, and long-term performance. Through his writing, coaching, and research, he helps people build healthier lives by focusing on sustainable habits, emotional resilience, and purposeful daily decisions.

After years of success in finance, Phil experienced his own health transformation that completely changed how he thinks about performance, longevity, and fulfillment. Today, he believes one of the biggest blind spots in retirement planning isn't your portfolio, it's your health. Because no matter how well you've prepared financially, it's difficult to enjoy the retirement you've worked so hard to build without the physical and mental capacity to fully experience it.

In our conversation, Phil shares why health and wealth follow many of the same behavioral principles, how our relationship with food and money is driven by the same psychological forces, and why improving your health may be the greatest investment you can make in your future.

In this podcast interview, you'll learn:

Why your health may be the most overlooked risk to a successful retirement.
How our relationship with food and money is shaped by the same psychological biases.
Why lasting health habits are built through identity, not willpower.
How improving your metabolic health can lead to better decisions, focus, and resilience.
Why comparing yourself to your past self and nobody else creates the greatest long-term progress.
The simple daily habits Phil believes deliver the biggest return for your future health.

Show Notes: HowardBailey.com/575

📧 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

574: Why Most Stocks Fail (And What Retirees Need to Know) Jul 10, 2026

Show notes

Your greatest investment risk may not be missing the market, but relying on your ability to identify the small handful of stocks that become the next big winners.

As part of our "By the Numbers" series, topics covered in this episode include:

Why most individual stocks fail to outperform the market
What increasing market concentration means for retirees
Why average returns can create dangerous expectations
How to think about risk, diversification, and income in retirement
The surprising case for Treasury bills and liquidity

Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade and Bruce Feiler provide thoughtful insights and advice on how it applies to your unique financial situation.

Show Notes: HowardBailey.com/574

📧 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

573: The Life Transition Every Retiree Must Learn to Master Jul 03, 2026

Show notes

Retirement isn't just about leaving your career; it's about learning how to navigate one of life's biggest transitions with confidence and resilience. As part of our "Freedom After 50" series, best-selling author Bruce Feiler shares why the most fulfilling retirements come from embracing change instead of resisting it.

Topics covered in this episode:

Why retirement is often a "lifequake," not just a life event
The three phases everyone experiences during major life transitions
How to avoid getting stuck after retirement
How couples can navigate retirement transitions together
A simple exercise to identify where you are and what you need most

Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade and Bruce Feiler provide thoughtful insights and advice on how it applies to your unique financial situation.

Show Notes: HowardBailey.com/573

📧 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

572: Is AI Carrying the Entire Stock Market? Jun 26, 2026

Show notes

Could AI be the force preventing a recession, and are today's biggest AI winners only the beginning of a much larger economic transformation?

As part of our "By the Numbers" series, topics covered in this episode include:

Why market "breadth" matters more than headlines
How today's AI boom compares to the dot-com era
The four phases of the AI market cycle
What retirees should consider amid concentrated market growth

Today's article is from the TrendLabs.com titled Would We Be in a Recession Without AI Stocks? 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/572

📧 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

571: You've Saved for Retirement — So Why Does Spending Still Feel Wrong? Jun 19, 2026

Show notes

You've accrued wealth to finally retire, but your "best" retirement involves learning how to enjoy the life your wealth was meant to support. As part of our "Freedom After 50" series, hospice doctor Jordan Grumet explores how to discover what truly brings you fulfillment once money is no longer the main objective.

Topics covered in this episode:

The emotional transition from accumulation to retirement
Why reaching financial independence doesn't automatically create peace of mind
The 3 phases of spending and how expectations often clash with reality
Ways to spend with confidence while staying aligned with your values

Today's article is from the The Purpose Code blog titled How I Finally Stopped Caring About Spending. 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/571

📧 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

570: Is Your Social Security Really Worth $1 Million? Jun 12, 2026

Show notes

What if your Social Security benefit is worth far more than you realize, and the decision of when to claim it could be one of the biggest financial choices you'll ever make?

As part of our "By the Numbers" series, topics covered in this episode include:

Why Social Security should be viewed as an asset, not just monthly income
How claiming at 62 vs. 67 vs. 70 impacts lifetime value
The role inflation, taxes, and longevity play in your decision
Common misconceptions about Social Security "running out"
Practical steps to begin analyzing your own benefits today

Today's article is from the Mr. Money Mustache blog titled The Shockingly Simple Math Behind Social Security. 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/570

📧 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

569: Rethinking the 4% Rule for Today's Retirees with Bill Bengen Jun 08, 2026

Show notes

Today, I'm honored to welcome Bill Bengen to the podcast. Bill is widely known as the father of the 4% Rule and as one of the most influential retirement-income researchers in history. His groundbreaking research transformed the way financial advisors and retirees think about generating sustainable income in retirement, and his work continues to shape retirement planning decades after its initial publication.

Over the past 30 years, Bill has studied hundreds of historical retirement scenarios to better understand how retirees can spend confidently without the fear of running out of money. In his latest book, A Richer Retirement: Supercharging the 4% Rule to Spend More and Enjoy More, he challenges many assumptions people have about retirement spending and financial security.

In our conversation, Bill addresses one of the biggest misconceptions about the 4% Rule, which was never intended to be a spending target for everyone, why inflation remains the greatest threat to retirement income, and how market valuations impact sustainable withdrawal rates. Bill also shares his views on diversification, annuities, retirement spending, and the common reasons retirees continue to underspend despite having more than enough.

GET A FREE COPY OF BILL'S BOOK, A RICHER RETIREMENT: SUPERCHARGING THE 4% RULE TO SPEND MORE AND ENJOY MORE

Here's how:

Step 1: Subscribe to the podcast and leave an honest rating & review on iTunes. Step 2: 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 the original 4% Rule was designed around the worst retirement scenario in modern history.
How Bill's research evolved from a 4% withdrawal rate to 4.7% through broader diversification.
Why inflation remains the single greatest threat to a retiree's long-term success.
How market valuations influence sustainable withdrawal rates and retirement income planning.
Why many retirees could safely spend more than they currently believe.
Why planning horizons should extend well beyond your projected life expectancy.

Show Notes: HowardBailey.com/569

📧 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

568: The 4 Emotional Phases of Retirement with Fritz Gilbert Jun 05, 2026

Show notes

What happens when the retirement you worked so hard for doesn't feel as fulfilling as you imagined, and how can you rediscover purpose, structure, and joy in this next chapter of life?

As part of our "Freedom After 50" series, topics covered in this episode include:

Why the "honeymoon phase" of retirement eventually fades
Why curiosity may be the single most important retirement skill
Practical ways to experiment, reinvent yourself, and find purpose again
How retirees can avoid getting stuck in the "lost and loss" phase
Why retirement planning should include far more than finances

Today's article is from The Retirement Manifesto titled, The 4 Phases of 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/568

📧 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

567: Hidden Estate Planning Risks Retirees Overlook May 29, 2026

Show notes

Could one outdated beneficiary form, missing trust provision, or overlooked document completely derail the legacy you intended to leave behind?

Topics covered in this episode:

The biggest misconceptions retirees have about wills vs. trusts
Why beneficiary designations can override your will
The real purpose of a revocable living trust, and what it does NOT do
Why estate planning failures often come down to poor account titling and coordination
How trusts can protect children, spouses, and inherited assets from divorce, lawsuits, or poor financial decisions

Today's article is from The Retirement Manifesto titled, Do You Really Need a Trust? And Other Estate Planning Questions Retirees Ask Most. 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/567

📧 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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