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Retire With Purpose - The Retirement Podcast
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Retire With Purpose - The Retirement Podcast

Author: Casey Weade

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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.
596 Episodes
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Today, I'm excited to welcome Jacob Schroeder to the podcast. Jacob is a financial writer, content strategist, and creator of The Root of All blog, where he explores the relationship between money, meaning, psychology, and living a good life. His writing challenges the conventional ways we think about wealth and what it really means to be financially successful. After spending decades working hard, saving, and building wealth, retirement is supposed to be the time when you finally get to enjoy it. But having enough money to retire and actually feeling like you have enough are two very different things. And even when you've achieved financial independence, there's no guarantee that the happiness and fulfillment you've been working toward will follow. In our conversation, Jacob shares why the way we use our wealth matters just as much as how much we've accumulated. We also explore the emotional challenges of transitioning from saving to spending, why our relationship with money continues to evolve throughout retirement, and what it really takes to build a life that feels rich beyond the numbers in your portfolio. In this podcast interview, you'll learn: Why reaching your retirement savings goal doesn't always create a sense of financial security. How to recognize when you're accumulating wealth without a meaningful purpose behind it. Why having more money can magnify who you already are rather than make you happier. How to give yourself permission to spend on experiences without jeopardizing your financial future. The difference between résumé virtues and eulogy virtues and how they shape your financial decisions. Why creating meaningful relationships and feeling like you matter are essential to a fulfilling retirement. Show Notes: HowardBailey.com/596 📧 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
Retirement opens the door to new possibilities, but how do you decide what deserves your time, energy, and attention? Retirement coach Joe Casey explores the concept of retirement "electives" and how they can help you build a life filled with purpose, curiosity, and connection. In this episode, you'll learn: How to find the right amount of volunteering in retirement When work adds purpose — and when it simply fills your calendar Why becoming a beginner again can be so difficult Why "tiny experiments" can help you discover what you enjoy A simple 30-day challenge to help you find your next elective Listen in as CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/595 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu  📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process
Your retirement plan has to do more than survive market volatility; it has to keep working through a long life, changing health, unexpected costs and the possibility that you may one day struggle to make the decisions it requires. In this episode, you'll learn: Why longevity risk goes far beyond simply "not running out of money" How early market losses can affect your retirement income The hidden trade-off behind dynamic spending strategies Why health and long-term care costs can reshape your plan How cognitive decline can create a financial risk years before a diagnosis Practical ways to simplify and strengthen your retirement plan Today's article is from the Financial Planning Association titled, Beyond Sequence of Returns: The Four Risks to Retirement Security. Listen in as CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/594 📧 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 one of the keys to a happier, more meaningful retirement isn't doing more, but becoming more curious about the people and world around you? In this episode, psychology professor Dr. March Schulz explores: Why curiosity and attention are essential to deeper relationships Why talking to strangers can boost your happiness How to bring "fresh eyes" to a decades-long marriage or friendship A 7-day curiosity challenge you can try yourself Listen in as CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/593 📧 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
New research is challenging the way we think about the 4% rule — and revealing why a smarter retirement income strategy may be less about preserving every dollar and more about confidently funding the life you saved for. In this episode, you'll learn: What the 4% rule gets right — and where it falls short What new research reveals about hybrid income strategies The tradeoff between income, liquidity, inflation protection, and legacy How Social Security, investments, taxes, and guaranteed income can work together Today's article is from Insurance Newsnet titled, A Hybrid Approach Outperforms the 4% Rule, Researchers Find. Listen in as CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/592 📧 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
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