If retirement is supposed to bring freedom, why do so many people still feel unsettled, and what's behind that tension?

In this episode, we discuss:

• Why fear persists even with a strong financial plan
• Dangers of letting the news cycle shape your outlook
• Why retirees often search for a "true sage" — and why that search fails
• The "Yada" reflective framework and techniques for cultivating presence, peace, and self-awareness

Today's article is from our very own blog titled, When Knowledge Isn't Enough & The Quiet Fear Beneath Retirement. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore how news-driven anxiety, the search for certainty, and misplaced trust impact peace, and discover the Yada framework for cultivating presence and self-awareness.

Show Notes: HowardBailey.com/540

📧 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 a counterintuitive tax move today potentially lead to thousands in savings — or an unexpected tax trap tomorrow?

In this episode, we discuss:

• Why some retirees intentionally harvest capital gains
• How the 0% bracket really works
• When it may make sense to pay capital gains taxes now
• How to evaluate tax gain harvesting vs. Roth conversions using long-term projections
• Key tax-planning windows before Social Security, RMDs, and spousal filing changes

Today's article is from the Best Interest blog titled, The Numbers Behind Tax-Gain Harvesting. 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/539

📧 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 biggest obstacle to a joyful retirement isn't your money — but the belief that you never have enough of it?

In this episode, we discuss:

• Why "having enough" is both a financial and emotional question
• When saving "too well" creates new problems
• The FIRE movement cautionary tale
• The role of curiosity, creativity, and craft in a purposeful retirement

Today's article is from The Root of All titled, The Joy of Giving Up on "Having Enough". Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore the emotional side of financial security, the pitfalls of oversaving, and how curiosity, creativity, and craft can lead to a more purposeful next chapter.

Show Notes: HowardBailey.com/538

📧 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 thrilled to welcome Fritz Gilbert back for his second appearance on the podcast. Fritz is an award-winning blogger and author of The Retirement Manifesto, one of the most influential retirement blogs in the country. He has now been retired for six years, and while many people think the big transition ends the day you leave the workforce, Fritz's journey proves that retirement continues to evolve in meaningful, surprising, and deeply personal ways.

Recently, he announced he is stepping away from full-time blogging to spend more of his life "outside the walls," shifting his time toward family, exercise, charitable work, and the flexibility that first drew him to retirement. Fritz explains why stepping back wasn't a loss—it was a necessary reshuffling of cards in the ongoing "game of retirement poker."

In our conversation, Fritz discusses the surprising emotional journey of redefining retirement. He explains why he has never struggled with boredom, depression, or identity loss, and highlights how he avoided the most difficult retirement phase that nearly 70% face.

We also talk about one of the most overlooked elements of retirement satisfaction: giving yourself permission to spend your money—or gift to your kids—while you can enjoy the benefits, rather than clinging to your savings out of habit or fear. Fritz explains why intentional spending is not only rational but also often essential for living a fully realized, purposeful retirement.

In this podcast interview, you'll learn:

• How Fritz avoided boredom, identity loss, and the infamous "retirement dip."
• The surprising emotional transition his wife experienced after caregiving.
• Why replacing the non-financial benefits of work is a must.
• How to refine a bucket strategy and reduce interest-rate risk in retirement.
• The real challenge of Roth conversions and why liquidity matters.
• Why many retirees spend too little and how Fritz overcame that fear.
• How to support adult children without jeopardizing their independence.
• Why the 90/10 rule becomes unavoidable in retirement.

Show Notes: HowardBailey.com/537

📧 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

With talk of bubbles, corrections, and overvaluation dominating the headlines, we unpack how you can stay confident, stay invested, and stay sane when markets feel anything but predictable.

In this episode, we discuss:

• Reasons why you might reduce stock exposure
• Poor (or dangerous) reasons to move to cash
• The biggest threat to your portfolio
• Practical investment frameworks to leverage in today's economic climate

Today's article is from the Best Interest blog titled, Should Retirees Sell Stocks, Move to Cash? 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/536

📧 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

Discover why the biggest barrier to deeper relationships after 50 isn't conflict — it's the certainty we cling to without even realizing it.

In this episode, we discuss:

• Why certainty "hardens" as we age
• How to navigate generational divides
• How fear shapes our beliefs and actions
• Viewing values as flexible filters vs. rigid rules

Today's article is from our very own blog titled, The "Unforgivable Sin" in the Second Half of Life: When Certainty Replaces Wonder. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to discuss how to bridge generational divides, and how flexible values can open the door to more meaningful connections.

Show Notes: HowardBailey.com/535

📧 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

Gold has been surging lately, but is it truly a golden opportunity for retirees, or just another glittering distraction? Join us as we break down what's really driving gold's rise, explore its role as a diversification tool, and reveal what the data says about whether it deserves a spot in your portfolio.

In this episode, we discuss:

• Gold's big run
• Historical data of gold vs. equity returns
• Inflation confusion
• Central banks' role
• How to diversify and own gold wisely

Today's article is from the Of Dollars and Data titled, What's Going on With Gold?. 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/534

📧 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 striving for the "perfect" portfolio be holding you back from the fulfilling, financially confident life you've worked so hard for? Join us as we explore why embracing a "good enough" mindset can lead to greater happiness, balance, and confidence in retirement.

In this episode, we discuss:

• The myth of the "perfect" portfolio
• Satisficers vs. Maximizers
• The Boglehead Paradox
• Your life's "cups" of energy

Today's article is from the Morningstar titled, The Case for a 'Good Enough' Portfolio. 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/533

📧 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 speaking with David McKnight. David is a best-selling author, world-renowned tax strategist, and financial educator who challenges some of the most popular (and misleading) retirement gurus and influencers in the financial advice space. He's also a great friend, and beloved guest on the show and I'm excited to welcome him back for a 3rd time on the podcast.

David is well known as the author of The Power of Zero which was made into a full-length documentary film. In his latest book, The Guru Gap, he exposes why one-size-fits-all financial guidance from so-called experts often leaves retirees underprepared and overexposed to risk.

We discussed the psychological appeal of "guru" advice and how to identify when those blanket statements—like "annuities are bad" or "the 4% rule always works,"—do more harm than good. One of the things that I love about David is that he shares math-based insights into retirement income planning. We're talking about the true cost of longevity risk, and why annuities can often create more liquidity and peace of mind than traditional withdrawal strategies.

David also shares his perspective on the newly extended tax cuts, how to time Roth conversions in light of the One Big Beautiful Bill, and the three critical questions everyone needs to answer before moving money from tax-deferred to tax-free accounts.

Whether you're skeptical about annuities, curious about LIRPs, or confused by conflicting advice online, this episode will help you cut through the noise and design a retirement plan that's truly tailored to you—not to the masses.

GET A FREE COPY OF DAVID MCKNIGHT'S NEW BOOK, THE GURU GAP

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 "one-size-fits-all" financial advice can be dangerous in retirement planning.
• The psychological reason Americans follow gurus—and how it can derail your goals.
• The real math behind annuities, the 4% rule, and the illusion of liquidity.
• How life insurance can serve as a volatility buffer and long-term care resource.
• The truth about Roth conversions and the importance of your "drop-dead date."
• What the new One Big Beautiful Bill means for future tax rates.
• Why simplicity—not complexity—is the hallmark of truly successful investors.

Show Notes: HowardBailey.com/532

📧 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

Discover what new research reveals about how retirees actually spend their money — and why front-loading your retirement income plan could be the key to enjoying your healthiest, most fulfilling years first.

In this episode, we discuss:

• Pitfalls of traditional retirement income plans
• What to know about the "retirement spending smile"
• Spending regret factors for retirees
• Health and longevity perceptions

Today's article is from the ThinkAdvisor titled, Most Retirees Want to Front-Load Their 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/531

📧 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