What does the “One Big Beautiful Bill Act” mean for your retirement? Find out how the latest tax legislation—from permanent TCJA extensions to surprising changes in charitable giving, Social Security taxation, 529 plan use, and more—could affect your tax strategy for years to come.

In this episode, we discuss:

• Updated inflation adjustments
• Capital gains nuance
• Enhanced standard deduction for seniors
• Social Security misconceptions
• New “below-the-line" deductions

Today's article is from the Kitces.com blog titled, Breaking Down The “One Big Beautiful Bill Act”: Impact Of New Laws On Tax Planning. 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/513

📧 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

Have you ever held on to something just because you’ve “put too much into it to let it go”? Many of us fall into the sunk cost fallacy trap—the quiet force that keeps us tied to the past. Whether it’s a house full of memories that no longer fits your lifestyle, a career that defined your identity for decades, or a friendship that’s no longer life-giving, this conversation will help you identify what might be holding you back—and, more importantly, how to move forward. 

In this episode, we discuss: 

• How sunk costs can go far beyond money
• Why letting go = gaining freedom
• 3 strategies to overcome the sunk cost fallacy
• KHIs vs. KPIs

Today's article is from The Critical Thinker titled The Sunk Cost Fallacy and How It Influences Our Decisions. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to unpack the sunk cost fallacy and how it quietly holds retirees back.

Show Notes: HowardBailey.com/512

📧 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

Are your Required Minimum Distributions (RMDs) setting you up for failure? Find out how sequence of returns risk combines with RMD rules to create a hidden hazard—and how smart planning, asset allocation, and timely Roth conversions can help you sidestep it.  

In this episode, we discuss: 

• Why RMDs are self-regulating
• The RMD tax chain reaction
• Why withdrawal timing and asset allocation matters
• The power of Roth conversions

Today's article is from the Best Interest blog titled, RMDs + Sequence Risk = Retirement Destruction? 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/511

📧 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 William Bernstein. Bill is a renowned investment advisor, author, and retired neurologist. He's the co-founder of Efficient Frontier Advisors, a leading voice in the world of personal finance, and the author of several acclaimed books, including The Four Pillars of Investing, The Investor's Manifesto, and The Intelligent Asset Allocator. 

With a unique background in neurology and finance, Bill brings a practical and evidence-based perspective to long-term investing, risk management, and financial behavior—especially for retirees and those nearing retirement. You'll hear why Bill believes the purpose of money isn't to buy things—it's to purchase autonomy, time, and peace of mind.

In our conversation, we explore what it really means to "win the game" of investing—and why continuing to play after you've won could jeopardize your retirement security. Bill breaks down the risks investors often overlook, including deep risk versus shallow risk, the need versus capacity and tolerance framework, and why having a basic understanding of financial history is an underrated skill set.

They also discuss how aging affects investment decisions, how burn rate should influence equity allocation, and why a purposeful retirement plan extends far beyond growing net worth. 

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• Step 1.) Subscribe to the podcast and leave an honest rating & review over on iTunes.
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In this podcast interview, you’ll learn:

• Why investors should reduce risk once they've “won the game”—and what that means in real terms.
• The critical differences between deep risk and shallow risk, and how to guard against both.
• How age and withdrawal rate should shape your stock-to-bond ratio in retirement.
• Why Treasury Inflation-Protected Securities (TIPS) can play a key role in risk management.
• The emotional traps investors fall into—and why historical financial knowledge is a great asset.
• What purpose in retirement really looks like—and why forging connections may be more valuable than money.

Show Notes: HowardBailey.com/510

📧 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 your greatest growth in retirement didn’t come from doing more—but from finally sitting with who you are? Throughout this discussion, we explore the concept of the “shadow self”—the parts of yourself that you may avoid, hide, or ignore—and how bringing light to these areas can lead to true peace and deeper connection in the second half of life. 

In this episode, we discuss: 

• How unresolved emotional patterns can impact health, relationships, and joy
• Why it’s important to take inventory of the roles you’ve been praised for
• How to leverage retirement as a mirror and own where you’re out of alignment

Today's article is from our very own blog post which you can find here. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore how embracing your “shadow self” can lead to deeper peace and fulfillment in retirement. 

Show Notes: HowardBailey.com/509

📧 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 you did everything “right” in retirement, but were still left surprised? That’s exactly what happened to Fritz Gilbert, one of our favorite past podcast guests. In this episode, we unpack his recent article, “My Biggest Surprise in Retirement,” and explore why his carefully planned Roth conversions didn’t make the impact he expected. This conversation is for anyone who wants to stay in the driver’s seat—no surprises, no backseat driving from Uncle Sam—just thoughtful, purpose-driven planning. 

In this episode, we discuss: 

• Why Roth conversions may not reduce your tax-deferred balance as expected
• Why waiting until retirement to convert might be too late
• Strategic conversions = lower RMDs, Medicare premiums, and taxes for heirs
• The ripple effects of taxes: Medicare IRMAA, Social Security, legacy

Today's article is from The Retirement Manifesto blog titled, My Biggest Surprise in 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/508

📧 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

In this powerful follow-up episode, Casey Weade and Certified Retirement Coach Les McDaniel return to explore the deeper question behind advice-seeking: Are you truly looking for direction, or for alignment with your values? Drawing from real-life coaching stories, they unpack six invitations to help you pause, reflect, and realign your financial decisions with your life’s purpose.  

In this episode, we discuss: 

• How to ask better questions
• Ways to elevate your emotional awareness
• How to separate valuable advice from projection-based advice

Today's article is from our very own blog post which you can find here. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore how aligning advice with your core values leads to better financial decisions.

Show Notes: HowardBailey.com/507

📧 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're like many retirees we meet with, you may struggle to spend confidently in retirement, even when you've saved enough. Here, we explore a potential strategy: an alternative to the annuity-based "License to Spend" model.    

In this episode, we discuss: 

• The dynamics of underspending in retirement
• How to apply the “Funded Status Metric” and “Surplus Bucket” to your income plan
• Pros and cons of leveraging this strategy
• A refresher of the “Funded Ratio”
• How to find an income strategy that aligns with your values

Today's article is from Advisor Perspectives titled, Use the Funded Status Metric & A ‘Surplus Bucket’ to Increase Spending in 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/506

📧 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

Understanding your own story is the missing link between receiving advice and applying it meaningfully. If you’ve ever felt stuck between wanting direction and feeling overwhelmed by options, this episode offers a practical path toward clarity, purpose, and peaceful resilience. 

In this episode, we discuss: 

• Advice vs. application
• A 3-step advice framework
• Advice overload
• Why incomplete context = incomplete advice

Today's article is from our very own blog post which you can find here. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to discuss how knowing your story can turn generic advice into meaningful action.

Show Notes: HowardBailey.com/505

📧 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 Dr. Ross Andel. Dr. Andel is a gerontologist, professor, and director of the PhD program at Arizona State University. Ross has spent decades researching aging, memory, and lifestyle-related cognitive health risks. In 2023, he was elected a lifetime fellow of the American Association for his achievements in the study of risk factors for age-related cognitive decline for Alzheimer's disease and other types of dementia.

Dr. Andel explains how daily routines and purpose directly impact brain function and why some retirees experience faster cognitive decline than others. He shares his findings from several international studies—including his viral TED Talk, "Is Retirement Bad for Your Brain?"—and delves into why your post-retirement plan matters just as much as your financial one. 

In our conversation, you'll hear why those who retire from high-level managerial careers may be at greater risk for faster cognitive decline in retirement, how volunteering and pursuing new hobbies improves brain function and Dr. Andel's poignant advice for anyone who is a caretaker for a loved one that is suffering from dementia or Alzheimer's.

In this podcast interview, you’ll learn:

• Why retirement without purpose can accelerate cognitive decline—and how to avoid the retirement trap.
• The connection between high-engagement careers and faster post-retirement mental decline.
• What research says about sleep, supplements, and cardiometabolic health for brain function.
• How race, gender, and job complexity influence cognitive aging differently.
• Why routine, exercise, and meaningful engagement are essential to brain longevity.

Show Notes: HowardBailey.com/504

📧 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