Retire With Purpose - The Retirement Podcast

Casey Weade
  • 4.7 (543)
  • INVESTING
  • UPDATED BIWEEKLY

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 Founder 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. ©2024 HOWARD BAILEY FINANCIAL, INC.

  1. 1D AGO

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

    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:  Why retirement feels more uncertain than working life How identity shifts after 50 can create anxiety What's true vs. what's just loud How to focus on what you can control — in life and money A 4-step practice to calm fear and regain clarity 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

    31 min

  2. JAN 23

    By the Numbers: Our 2026 Market Predictions

    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:  2026 S&P 500 predictions (15.2% vs. 6.7%) AI's explosive growth The Magnificent Seven's shrinking dominance Why equal-weighted investing reduces volatility Why bonds, gold, and diversification matter again How pre-retirees can protect gains while staying invested 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

    33 min

  3. JAN 16

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

    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:  Resume virtues vs. eulogy virtues Why many retirees feel "lost" after achieving everything they worked for How purpose changes the way you think about money, work, and time Using financial planning to create freedom, not pressure Redefining identity, success, and legacy after 50 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

    26 min

  4. JAN 12

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

    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: Why not all stress is harmful—and how the right stress promotes longevity. The difference between distress, eustress, and not enough stress. How meaning and purpose challenges us and strengthens resilience. Why avoiding stress in retirement can backfire physically and mentally. The role mitochondria play in our energy, aging, and stress levels. The importance of recovery and how it transforms stress into growth. Why purpose is actually beneficial in protecting us against aging. How to rethink retirement as a season of continued growth and contribution. 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

    1h 1m

  5. JAN 9

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

    You saved diligently for decades — so why does giving yourself permission to spend still feel so hard?  In this episode, we discuss:  Why many retirees underspend despite having a secure financial plan Emotional and psychological barriers to spending How lifelong, "saver" habits impact retirement decisions Low-risk strategies to help build spending confidence 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

    36 min

  6. JAN 2

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

    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:  The most common retirement regrets How to generate flexible, reliable income in retirement The Surplus Bucket Strategy and why it can help spending confidence How to understand your level of retirement readiness Why delaying joy can come at a higher cost than you think 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

    38 min

  7. 12/26/2025

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

    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

    21 min

  8. 12/19/2025

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

    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

    31 min
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4.7
out of 5
543 Ratings

About

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 Founder 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. ©2024 HOWARD BAILEY FINANCIAL, INC.

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