Retire With Purpose - The Retirement Podcast

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: https://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

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

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: https://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

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

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: https://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

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

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: https://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

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

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: https://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

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

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: https://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

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

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: https://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

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

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: https://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

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

Today, I'm excited to welcome Ken Stern to the podcast. Ken is the founder and chair of the Longevity Project, host of Century Lives from the Stanford Center on Longevity, former CEO of NPR, and author of Healthy to 100: How Strong Social Ties Lead to Long Lives. His research explores an aspect of retirement planning that rarely gets enough attention: our social health.

Far too many people spend years wondering whether they've saved enough to retire, but very few think about whether they are socially ready to retire. Work provides much more than a paycheck. It provides routines, relationships, purpose, and regular interaction with other people, but when that disappears, retirement can become far more isolating than most people anticipate.

In our conversation, Ken explains why strong social connections are critical to our health and longevity, how to replace the relationships and routines we lose when we leave the workforce, and why we should approach retirement with the same intentionality we brought to our careers.

GET A FREE COPY OF KEN'S BOOK, HEALTHY TO 100: HOW STRONG SOCIAL TIES LEAD TO LONG LIVES

Here's how: Just 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 being financially ready for retirement doesn't necessarily mean you're socially ready.
• How leaving the workforce can unexpectedly disrupt your relationships, routines, and sense of purpose.
• Why strong social connections can play such an important role in healthy aging and longevity.
• What longer-lived countries can teach us about work, learning, volunteering, and intergenerational connection.
• How place planning and proximity can make it easier to build meaningful relationships in retirement.
• Why your social connection plan should begin long before your final day of work.

Show Notes: https://howardbailey.com/586

📧 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

What if getting older doesn't mean losing happiness, but gaining more of it? Author Don Ezra explores the surprising science behind the U-curve of happiness and why perspective, purpose, gratitude, and letting go of perfection can make the years ahead some of your best.

In this episode, you'll learn:

• Why happiness often dips in midlife and rises again later in life
• How dopamine influences our desire for "more"
• The connection between purpose and life satisfaction
• A simple exercise for cultivating gratitude and greater life satisfaction

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

Show Notes: https://howardbailey.com/585

📧 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

You may own hundreds of stocks, but that doesn't necessarily mean you're diversified. Discover where concentration risk is really hiding and what you can do about it.

In this episode, you'll learn:

• Why owning an S&P 500 index fund may expose you to more concentration risk than you realize.
• The difference between company concentration and sector concentration
• Whether international investing actually reduces portfolio risk.
• Why equal-weight investing is gaining attention in today's market.
• How to think about highly appreciated individual stock positions before retirement.
• The one portfolio analysis every retiree should consider.

Today's article is from TrendLabs titled, What You Need To Know About the Market Concentration Myth. 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: https://howardbailey.com/584

📧 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

Your finances may be ready to enter your second act, but retirement coach Joe Casey explains why the bigger question is whether you've prepared for the life, relationships, health, learning, and fun that come after work.

In this episode, you'll learn:

• Why having more free time doesn't automatically create a fulfilling life
• How retirement can expose gaps in your social life
• Why your "best Wednesdays" may matter more than your bucket list
• How to start experimenting with your future before retirement
• The questions you and your spouse should be asking before you leave work

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

Show Notes: https://howardbailey.com/583

📧 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

Could doing everything "right" with your retirement savings actually be limiting your financial freedom?

As part of our "By the Numbers" series, in this episode, you'll learn:

• Why "max out your 401(k)" isn't always the right answer
• The overlooked value of liquidity and accessible cash
• When you may have already saved enough for retirement
• How taxes can quietly become one of retirement's biggest expenses
• Why your retirement plan should support your life; not the other way around

Today's article is from the Use Your Wealth blog titled You Should Probably Stop Saving for 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: https://howardbailey.com/582

📧 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

What if one of the biggest keys to a healthy, meaningful retirement has nothing to do with money? Author and psychology professor Dr. Marc Schulz reveals why your relationships, social connections and "social fitness" may play a surprisingly important role in how well you age — and how you can strengthen them before and during retirement.

In this episode, you'll learn:

• How retirement can disrupt your social network
• Ways introverts and extroverts can approach social fitness differently
• The "2 a.m. friend" test for evaluating your relationships
• How couples can navigate different social needs in retirement
• Dr. Schulz's practical 30-day social fitness challenge

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

Show Notes: https://howardbailey.com/581

📧 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

Today, I'm excited to welcome Bill Perkins to the podcast. Bill is an entrepreneur, hedge fund manager, investor, and bestselling author of Die With Zero: Getting All You Can from Your Money and Your Life. Throughout his career, he's challenged one of the most common assumptions about wealth: that accumulating more money should always be the ultimate goal. Instead, Bill encourages people to think differently about how they use their time, health, and financial resources to create a more fulfilling life.

Far too many retirees spend decades building wealth only to discover that saving money is much easier than confidently spending it. Bill believes retirement isn't about maximizing your account balance; it's about maximizing your experiences while you still have the health and time to enjoy them. That means being intentional about when you travel, when you create memories with loved ones, and even when you pass wealth on to the next generation.

In our conversation, Bill explains why money should always serve your life instead of becoming the goal itself, how "time bucketing" can help prioritize life's most meaningful experiences, why health may be your most valuable retirement asset, and how intentionally spending, giving, and creating memories can ultimately lead to a richer and more purposeful retirement.

GET A FREE COPY OF BILL'S BOOK, DIE WITH ZERO: GETTING ALL YOU CAN FROM YOUR MONEY AND YOUR LIFE

Here's how: Just 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 maximizing fulfillment—not maximizing wealth—should become your retirement goal.
• How time bucketing helps you prioritize experiences before opportunities disappear.
• Why your health becomes one of your most valuable retirement resources.
• How memory dividends can create lasting returns long after an experience ends.
• Why intentionally giving wealth during your lifetime may create a greater legacy than leaving an inheritance after you're gone.
• How designing simple systems can help you live more intentionally instead of on autopilot.

Show Notes: https://howardbailey.com/580

📧 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

Headlines say Social Security is going bankrupt, but the real story is far more nuanced, and understanding it could help you make smarter retirement decisions before it's too late.

In this episode, you'll learn:

• What the latest 2026 Trustee Report reveals
• Why retirees could still receive benefits, even without Congressional action
• How AI, longevity, and future productivity could change the outlook
• The most likely solutions Congress could pursue
• How to stress test your retirement income plan for multiple Social Security scenarios

Today's article is from the Center for Retirement Research at Boston College titled, Social Security's Financial Outlook: The 2026 Update in Perspective. 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: https://howardbailey.com/579

📧 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

When it comes to a confident retirement, what if the biggest risk isn't running out of money, but waiting too long to enjoy it? As part of our "Freedom After 50" series, author Mike Drak explores:

• Why so many retirees struggle emotionally with spending
• How retirement spending naturally changes over time
• The difference between spending on things vs. meaningful experiences
• How fear of future healthcare costs can hold you back today
• Practical ways to spend with greater confidence and fewer regrets

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

Show Notes: https://howardbailey.com/578

📧 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

Everyone says to "invest for the long term," but what does that actually mean when you're approaching or living in retirement?

As part of our "By the Numbers" series, in this episode, you'll learn:

• Why "long term" means much more than simply waiting
• How retirement changes the way you should think about investing
• The psychological cost of staying invested during market downturns
• Why buying and forgetting isn't a successful investment strategy
• How to know if you're taking more risk than you actually need

Today's article is from the Safal Niveshak blog titled What I Mean When I Say 'Long Term' 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: https://howardbailey.com/577

📧 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

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: https://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

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: https://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

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