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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:

496: Claiming Social Security Early: Is it the Right Strategy for You? Apr 25, 2025

Show notes

Conventional financial wisdom encourages you to delay collecting Social Security benefits until age 70, but in certain cases, your "optimal" claiming age might actually be to pull benefits early.

In this episode, we discuss:

Factors that benefit filing early
Your "breakeven" number of filing early vs. later
How your rate of return should factor into your Social Security strategy

Today's article is from Vanguard titled, Social Security: For Some, Early Claiming is Better. 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/496

📧 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/3z5mXIw

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

495: Freedom After 50: The World is Ending… What's Next? Apr 18, 2025

Show notes

If you saw the amount of time you had left to live—whether it was one day or one year—how would you spend it? What would you worry about?

In this episode, we discuss:

How to let go of always trying to control your narrative
Why the pursuit of contentment is greater than the pursuit of happiness
5 questions to help you find pure contentment in the present

Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to run through 5 questions that will help you find pure contentment by living in the now.

Show Notes: Howardbailey.com/495

📧 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/3z5mXIw

494: Beyond the Headlines: How Retirees Can Navigate Investment Risks with Larry Swedroe Apr 14, 2025

Show notes

Today, I'm speaking with Larry Swedroe. Larry is the former Chief Research Officer at Buckingham Strategic Wealth, an accomplished author with 18+ books on investing, and a true pioneer in evidence-based investing. He's also a well-known advocate for cutting through the financial media noise to focus on strategies that actually work.

In Larry's latest book, Enrich Your Future: The Keys to Successful Investing, he distills decades of financial wisdom into 40 powerful stories that make investing principles easy to understand and apply.

In our conversation, Larry shares the science behind behavioral finance and explains why most investors fall prey to emotional biases, media hype, and market timing traps. We also dive into why passive investing remains a leading strategy among investors, how to truly measure risk, and why a globally diversified portfolio beats stock-picking in the long run.

GET FREE ACCESS TO LARRY'S BOOK TITLED, ENRICH YOUR FUTURE: THE KEYS TO SUCCESSFUL INVESTING

Here's all you have to do...

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 passive investing isn't just a trend—it's a game-changer for wealth-building.
The biggest mistakes investors make and how to avoid them.
The difference between risk and uncertainty, and why most investors get it wrong.
Why the market is smarter than any single investor and what that means for your portfolio.
How to structure an investment portfolio based on empirical research, not emotions.
The surprising link between retirement, purpose, and mental health—especially for retired men.

Show Notes: Howardbailey.com/494

📧 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/3z5mXIw

493: Chaotic Markets: A 4-Point Checklist to Safeguard Your Retirement Savings Apr 11, 2025

Show notes

Are you feeling uneasy right now? If market turmoil is causing you stress, it's time to determine if your retirement plan is truly built for the unexpected.

In this episode, we discuss:

How a process can give you greater investment and financial control
How to assess your liquid/safe reserves
Tax and inflation protection opportunities brought by market volatility

Today's article is from Morningstar titled, What Now? An Investor's To-Do List for Chaotic Markets. 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/493

📧 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/3z5mXIw

492: 3 Levels of Retirement Readiness: Where Do You Stand? Apr 04, 2025

Show notes

How would you rate yourself on the retirement readiness scale? When you understand where you are and how to proceed, you are more likely to feel elevated confidence to and throughout retirement.

In this episode, we discuss:

Financial vs. non-financial retirement readiness
Why your income strategy is key
Considerations for long term care insurance
How to prepare for financial change in retirement

Today's article is from The Retirement Manifesto titled, 3 Levels of Retirement Readiness: Where Do You Stand? 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/492

📧 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/3z5mXIw

491: Freedom After 50: 8 Reasons the Month You Retire Matters Mar 28, 2025

Show notes

Before you make your transition into retirement, it's important to dial in the ideal timing not just for your money, but your mind.

In this episode, we discuss:

Irrational reasons to not retire
The "3 Cs" of retirement timing
Family, health, and social considerations in retirement

Listen in as Casey Weade is once again joined by Les McDaniel to explore the common irrational fears about retiring.

To receive your FREE WISE Wealth Assessment worksheet, text WISE to 888-599-4491

Show Notes: Howardbailey.com/491

📧 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/3z5mXIw

490: Retirement Withdrawal Strategies in Down Markets: Should You Shift Yours? Mar 21, 2025

Show notes

Market volatility is inevitable. Whether you're 10 months or 10 years into retirement, it's vital to ask: is your investment strategy prepared?

In this episode, we discuss:

Why market volatility is necessary
When down markets no longer become an opportunity
How to avoid sequence of returns risk
4% withdrawal rule flaws

Today's articles are from The Best Interest blog titled, Should I "Reset" Retirement Withdrawals in Bad Markets? and Are You Not Entertained?! 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/490

📧 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/3z5mXIw

489: Freedom After 50: The 4 Myths of Security Keeping You Stuck Today and Fearful of Tomorrow Mar 14, 2025

Show notes

For decades, you've been told that security is the key to a successful life; Work hard, save wisely, and one day, you'll be able to retire with peace of mind. But what if the very idea of security is holding you back?

In this episode, we discuss:

The power of a decision-making framework
Pitfalls of delayed gratification
Financial security disillusions

Listen in as Casey Weade is once again joined by Les McDaniel to discuss challenges to the traditional notion of security as the key to a successful life.

To receive your FREE WISE Wealth Assessment worksheet, text WISE to 888-599-4491

Show Notes: Howardbailey.com/489

📧 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/3z5mXIw

488: From Accumulating to Spending: 20 Lessons for a Happy & Successful Retirement with Christine Benz Mar 10, 2025

Show notes

Today, 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

Here's all you have to do...

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

📧 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/3z5mXIw

487: Should You Pay Off Your Mortgage Before Retirement? Mar 07, 2025

Show notes

Is it OK for you to bring debt into retirement? More specifically, what about your mortgage? To gain clarity, you must approach this decision from a financial and emotional perspective.

In this episode, we discuss:

Historical vs. potential future of mortgage rates
Why a mortgage can be a valuable asset
How to determine your mortgage value

Today's article is from A Wealth of Common Sense titled, Should You Pay Off Your Mortgage Before 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/487

📧 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/3z5mXIw

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