Retire With Purpose - The Retirement Podcast

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

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: 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: 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: 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: 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: 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: 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: 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: 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: 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