Retire With Purpose - The Retirement Podcast-logo

Retire With Purpose - The Retirement Podcast

Business & Economics Podcasts

Whether you are in retirement or have yet to make the transition, The Retire With Purpose podcast is a show designed to help you maximize your financial confidence and elevate your fulfillment in this chapter of life. Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and CEO of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you've always imagined and deserve. Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations. ©2026 HOWARD BAILEY FINANCIAL, INC.

Location:

United States

Description:

Whether you are in retirement or have yet to make the transition, The Retire With Purpose podcast is a show designed to help you maximize your financial confidence and elevate your fulfillment in this chapter of life. Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and CEO of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you've always imagined and deserve. Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations. ©2026 HOWARD BAILEY FINANCIAL, INC.

Language:

English


Episodes
Ask host to enable sharing for playback control

550: By the Numbers: The Anchors of Retirement Confidence, Part 2 — Building a Plan for the Next Market Crash

2/20/2026
Join us as we continue our "Anchors of Retirement Confidence" series, where we discuss four areas of retirement uncertainty plus strategies to replace your anxiety with clarity and control. In part 2, we explore what really puts retirements at risk during market downturns — and how to build a plan that's designed to withstand them. In this episode, you'll learn: Today's article is from Morningstar titled, 8 Tips to Stop Worrying About Running Out of Money 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/550 📧 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

Duration:00:17:27

Ask host to enable sharing for playback control

549: Freedom After 50: The Hidden Link Between Your Money Habits and Your Life

2/13/2026
Are your investment habits quietly shaping the way you live — and could a few mindset shifts help you build a more patient, resilient, and fulfilling retirement? In this episode, you'll learn: life Today's article is from Vishal Khandelwal's Substack titled, One Long Game. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore how investing habits shape life beyond money—and how mindset shifts can build patience, resilience, and fulfillment in retirement. Show Notes: HowardBailey.com/549 📧 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

Duration:00:32:05

Ask host to enable sharing for playback control

548: Conscious Aging: Finding Meaning, Purpose, and Growth in Retirement with Ron Pevny

2/9/2026
Today, I'm thrilled to welcome Ron Pevny to the podcast. Ron is the founder and director of the Center for Conscious Eldering, a certified Sage-ing Leader with Sage-ing International, and a longtime guide for individuals navigating life's most meaningful transitions. With a master's degree in integral counseling and psychotherapy, Ron has spent decades helping people move through major life passages with intention, clarity, and depth. Ron is also the author of Conscious Living, Conscious Aging: Claiming the Gifts of Elderhood, a powerful guide for those entering the later chapters of life and seeking more than just rest or recreation. His work reframes aging not as decline, but as an opportunity to step into elderhood with purpose—drawing on wisdom, lived experience, and a renewed commitment to growth and contribution. In our conversation, we explore what it truly means to become an elder in today's world. Ron shares the catalysts that led him into this work, including profound health challenges that reshaped his perspective on purpose and calling. We also discussed the three-phase transition into elderhood and why honoring each stage is essential for discovering what's next after retirement. GET A FREE COPY OF RON PEVNY'S BOOK, CONSCIOUS LIVING, CONSCIOUS AGING: CLAIMING THE GIFTS OF ELDERHOOD 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: Show Notes: HowardBailey.com/548 📧 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

Duration:01:02:15

Ask host to enable sharing for playback control

547: By the Numbers: The Anchors of Retirement Confidence, Part 1 — Finding Your Sustainable Spending Range

2/6/2026
Join us for our "Anchors of Retirement Confidence" series, where we discuss four areas of retirement uncertainty plus strategies to replace your anxiety with clarity and control. In part 1, we tackle how to create a flexible spending system that adapts with you. In this episode, you'll learn: Today's article is from Morningstar titled, 8 Tips to Stop Worrying About Running Out of Money 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/547 📧 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

Duration:00:19:37

Ask host to enable sharing for playback control

546: Freedom After 50: How to Stay Grounded When the Future Feels Unknown

1/30/2026
What if the key to a calmer, more meaningful retirement isn't having all the answers, but learning how to trust yourself when you don't? In this episode, we discuss: trueloud Today's article is from our very own blog titled, Approaching Uncertainty with Yada. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore why retirement can feel more uncertain than working life. Show Notes: HowardBailey.com/546 📧 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

Duration:00:31:16

Ask host to enable sharing for playback control

545: By the Numbers: Our 2026 Market Predictions

1/23/2026
Will 2026 deliver another strong bull-market year — or a long-overdue reality check as AI, market valuations, and global shifts collide? In this episode, we discuss: Today's article is from Kitces.com titled, 10 Charts To Help Explain The 2026 Market To Clients. 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/545 📧 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

Duration:00:33:12

Ask host to enable sharing for playback control

544: Freedom After 50: Are You Living for Your Resume—or Your Eulogy?

1/16/2026
What if the real measure of a successful retirement isn't what you've built, but who you've been, and how your money supports the life you want to be remembered for? In this episode, we discuss: Today's article is from The Root of All titled, Living for the Eulogy. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore how redefining success through purpose, legacy, and "eulogy virtues" can transform retirement. Show Notes: HowardBailey.com/544 📧 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

Duration:00:25:37

Ask host to enable sharing for playback control

543: The Stress Paradox: Why the Right Kind of Stress Helps You Thrive in Retirement with Dr. Sharon Bergquist, MD

1/12/2026
Today, I'm excited to welcome Dr. Sharon Bergquist to the podcast. Sharon is a board-certified physician, research scientist, founder of Emory Lifestyle Medicine & Wellness, and an internationally recognized leader in lifestyle medicine. She has led or co-led over a dozen clinical trials that have received $61 million in funding to evaluate lifestyle interventions and identify early biomarkers for chronic disease, including ongoing studies for early detection of Alzheimer's disease and cancer. Her work is at the forefront of how we understand the role of stress and resilience on our health and longevity. As the author of The Stress Paradox: Why You Need Stress to Live Longer, Healthier, and Happier, Dr. Bergquist brings a deeply personal and scientific perspective to the conversation. She shares how early-life adversity shaped her understanding of resilience and how decades of clinical research led her to challenge the conventional narrative about stress. Sharon explains why not all stress is harmful, how the body is biologically designed for growth through challenge, and why eliminating stress may actually harm long-term health and longevity. In our conversation, we explore the science behind how good stress in the "Goldilocks Zone" can strengthen the body and mind. Sharon outlines how purposeful stress supports mitochondrial health, cognitive function, physical capacity, and emotional well-being, and explains why recovery is just as essential as the challenges we create and overcome. GET A FREE COPY OF DR. SHARON BERGQUIST'S NEW BOOK, THE STRESS PARADOX: WHY YOU NEED STRESS TO LIVE LONGER, HEALTHIER, AND HAPPIER 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: Show Notes: HowardBailey.com/543 📧 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

Duration:01:01:11

Ask host to enable sharing for playback control

542: By the Numbers: From Fear to Freedom — Learning How to Spend in Retirement

1/9/2026
You saved diligently for decades — so why does giving yourself permission to spend still feel so hard? In this episode, we discuss: Today's article is from the Kitces blog titled, Helping Underspenders And "Savers" Understand They CAN Spend More With 4 Stages Of "Experiments". 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/542 📧 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

Duration:00:36:11

Ask host to enable sharing for playback control

541: Your 2026 Reset: The Best of the Retire With Purpose Podcast

1/2/2026
What can our top five Retire With Purpose Podcast episodes of 2025 teach you about avoiding regrets, spending confidently, and living with purpose as you head into 2026? In this episode, we discuss: Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade kicks off the new year with a "Best Of" episode to reflect on the best moments from 2025 by revisiting the insights that resonated the most with you, the listener, this past year. Show Notes: HowardBailey.com/541 📧 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

Duration:00:38:24

Ask host to enable sharing for playback control

540: Freedom After 50: The Quiet Fear Beneath Retirement (and How to Outsmart It)

12/26/2025
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: 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

Duration:00:20:33

Ask host to enable sharing for playback control

539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions

12/19/2025
Could a counterintuitive tax move today potentially lead to thousands in savings — or an unexpected tax trap tomorrow? In this episode, we discuss: 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

Duration:00:30:38

Ask host to enable sharing for playback control

538: Freedom After 50: Why Enough Is a Mindset, Not a Number

12/12/2025
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: 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

Duration:00:25:38

Ask host to enable sharing for playback control

537: The Most Overlooked Elements of a Successful Retirement with Fritz Gilbert

12/8/2025
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: non-financial 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

Duration:01:07:16

Ask host to enable sharing for playback control

536: By the Numbers: Cash Out or Hold On? The Retiree's Dilemma

12/5/2025
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: 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

Duration:00:38:52

Ask host to enable sharing for playback control

535: Freedom After 50: The "Unforgivable Sin" in the Second Half of Life

11/28/2025
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: 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

Duration:00:29:51

Ask host to enable sharing for playback control

534: By the Numbers: Gold vs. Stocks — What the Data Says About Retirement Portfolios

11/21/2025
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: 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

Duration:00:27:59

Ask host to enable sharing for playback control

533: By the Numbers: The Case for "Good Enough" — Why Simplicity Often Beats Perfection in Retirement Planning

11/14/2025
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: 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

Duration:00:18:54

Ask host to enable sharing for playback control

532: Debunking Advice From Financial "Gurus" to Create An Efficient Retirement Income Plan with David McKnight

11/10/2025
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: 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

Duration:01:01:25

Ask host to enable sharing for playback control

531: By the Numbers: Why Retirees Often Spend Too Little, Too Late

11/7/2025
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: 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

Duration:00:26:21