Casey Weade

Retire With Purpose - The Retirement Podcast

Business EN ↓ 574 episodes

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. Investmen...

Author

Casey Weade

Category

Business

Podcast website

retirewithpurpose.com

Latest episode

Jul 10, 2026

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Episodes

574: Why Most Stocks Fail (And What Retirees Need to Know) 10.07.2026

Your greatest investment risk may not be missing the market, but relying on your ability to identify the small handful of stocks that become the next big winners.  As part of our "By the Numbers" series, topics covered in this episode include:  Why most individual stocks fail to outperform the market What increasing market concentration means for retirees Why average returns can create dangerous e...

573: The Life Transition Every Retiree Must Learn to Master 03.07.2026

Retirement isn't just about leaving your career; it's about learning how to navigate one of life's biggest transitions with confidence and resilience. As part of our "Freedom After 50" series, best-selling author Bruce Feiler shares why the most fulfilling retirements come from embracing change instead of resisting it. Topics covered in this episode:  Why retirement is often a "lifequake," not jus...

572: Is AI Carrying the Entire Stock Market? 26.06.2026

Could AI be the force preventing a recession, and are today's biggest AI winners only the beginning of a much larger economic transformation?  As part of our "By the Numbers" series, topics covered in this episode include:   Why market "breadth" matters more than headlines How today's AI boom compares to the dot-com era The four phases of the AI market cycle What retirees should consider amid conc...

571: You've Saved for Retirement — So Why Does Spending Still Feel Wrong? 19.06.2026

You've accrued wealth to finally retire, but your "best" retirement involves learning how to enjoy the life your wealth was meant to support. As part of our "Freedom After 50" series, hospice doctor Jordan Grumet explores how to discover what truly brings you fulfillment once money is no longer the main objective.  Topics covered in this episode:  The emotional transition from accumulation to reti...

570: Is Your Social Security Really Worth $1 Million? 12.06.2026

What if your Social Security benefit is worth far more than you realize, and the decision of when to claim it could be one of the biggest financial choices you'll ever make?   As part of our "By the Numbers" series, topics covered in this episode include:  Why Social Security should be viewed as an asset, not just monthly income How claiming at 62 vs. 67 vs. 70 impacts lifetime value The role infl...

569: Rethinking the 4% Rule for Today's Retirees with Bill Bengen 08.06.2026

Today, I'm honored to welcome Bill Bengen to the podcast. Bill is widely known as the father of the 4% Rule and as one of the most influential retirement-income researchers in history. His groundbreaking research transformed the way financial advisors and retirees think about generating sustainable income in retirement, and his work continues to shape retirement planning decades after its initial...

568: The 4 Emotional Phases of Retirement with Fritz Gilbert 05.06.2026

What happens when the retirement you worked so hard for doesn't feel as fulfilling as you imagined, and how can you rediscover purpose, structure, and joy in this next chapter of life?  As part of our "Freedom After 50" series, topics covered in this episode include:  Why the "honeymoon phase" of retirement eventually fades Why curiosity may be the single most important retirement skill Practical...

567: Hidden Estate Planning Risks Retirees Overlook 29.05.2026

Could one outdated beneficiary form, missing trust provision, or overlooked document completely derail the legacy you intended to leave behind?  Topics covered in this episode:  The biggest misconceptions retirees have about wills vs. trusts Why beneficiary designations can override your will The real purpose of a revocable living trust, and what it does NOT do Why estate planning failures often c...

566: Freedom After 50: How to Avoid Retirement Shock and Find Purpose Again with Mike Drak 22.05.2026

Retirement isn't always the carefree finish line people imagine. For many, it marks the start of a deeper search for purpose, identity, and fulfillment.  Topics covered in this episode:  Why so many retirees experience "retirement shock" after leaving work How loss of structure and purpose can impact happiness and mental health The growing importance of part-time work, passion projects, and volunt...

565: By the Numbers: Why 42% of Inheritances Disappear Within a Year 15.05.2026

What if the biggest risk to your legacy isn't taxes, but what your heirs do with the money once it's in their hands?  Topics covered in this episode:  Emotional and psychological triggers behind overspending Wealth transfer vs. wealth preservation Ways to give heirs a "second chance" with smarter distributions The role of trusts, trustees, and incentive-based planning Why communication with heirs...

564: Signal vs. Noise: How to Make Smarter Retirement Planning Decisions with Jesse Cramer 11.05.2026

Today, I'm very excited to welcome Jesse Cramer to the podcast. Jesse is the founder of The Best Interest blog and host of the Personal Finance for Long-Term Investors podcast, where he helps individuals cut through the noise of financial media and focus on what truly matters. In a world filled with headlines, predictions, and never-ending market chatter, Jesse brings a refreshing perspective for...

563: Freedom After 50: From Bucket List to Life Strategy with Jet Vertz 08.05.2026

What if the goal of your bucket list isn't to slowly check it off, but to finish it, rebuild it, and use it to fuel a more meaningful retirement?  Topics covered in this episode:  How to build a purpose-driven bucket list that actually gets completed Why most bucket lists are too "self-focused" and how to fix that The power of small, achievable goals Why sharing your goals increases follow through...

562: By the Numbers: Why Your Tax Refund Isn't What You Think 01.05.2026

Are you actually better off getting a tax refund, or is your brain tricking you into celebrating a financial loss?   Topics covered in this episode:  Tax refunds vs. tax liability: what actually matters Behavioral biases (framing, loss aversion, anchoring, etc.) Strategic tax planning vs. emotional decision-making Real-world examples from retirees and working families How to align tax strategy wit...

561: Freedom After 50: The 80% Rule That Could Change Your Retirement Timeline with Jordan Grumet, MD 24.04.2026

What if waiting until you're "fully ready" for retirement is actually costing you some of the best years of your life?   Topics covered in this episode:  The controversial "retire at 80%" framework Why most retirees don't run out of money The reality behind retirement spending patterns The emotional and psychological barriers to retiring Why time may be more valuable than financial certainty How t...

560: By the Numbers: Can You Really Beat the Market by Avoiding the Worst Days? 17.04.2026

What if trying to avoid the market's worst days is actually one of the fastest ways to sabotage your retirement plan?  Topics covered in this episode:  Why best and worst market days often occur back-to-back The math of gains vs. losses — and why it's not equal The "lost decade" and what it teaches investors Why avoiding bad years matters more than avoiding bad days How reduced volatility strategi...

559: How Dopamine Shapes Your Motivation, Happiness, and Purpose in Retirement with Michael Long 13.04.2026

Today, I'm excited to welcome Michael Long to the podcast. Michael is a physicist-turned-writer and the co-author of the international bestseller The Molecule of More. His work explores one of the most powerful forces shaping our lives: the brain chemical dopamine — and how it influences motivation, ambition, and our constant drive for "more." Michael is also the author of Taming the Molecule of M...

558: By the Numbers: The Bucket Strategy vs. 60-40 - Who Really Wins? 10.04.2026

What if the strategy you trust most for retirement income is quietly costing you hundreds of thousands of dollars?   Topics covered in this episode:  The real driver behind outperformance Sequence of returns risk and the "retirement risk zone" Why rebalancing can help (or hurt) your long-term results The surprising case for increasing equity exposure over time Limitations of bonds in modern retire...

557: By the Numbers: The Fragile Decade That Could Make (or Break) Your Retirement 03.04.2026

What if the real retirement risk zone isn't during retirement… but the five critical years before and after it begins?   In this episode, you'll learn about:  Pre- vs. post-retirement sequence of returns risk How to stress test your retirement plan effectively The role of asset allocation shifts in late-stage accumulation Why target date funds may carry more risk than expected How to build income...

556: By the Numbers: Could the Government Tax Your Roth IRA in the Future? What if Congress Changes the Rules? 27.03.2026

If you convert to a Roth today, could Congress change the rules tomorrow — and should that fear stop you from taking action?  In this episode, you'll learn:  The truth about retroactive Roth taxation Why traditional IRA risk may be greater than Roth risk How RMDs can quietly create massive tax exposure What recent legislation signals about the future of Roth accounts Why tax diversification — not...

555: By the Numbers: The Anchors of Retirement Confidence, Part 4 — Building a Retirement That Can't Break 20.03.2026

Join us as we continue our "Anchors of Retirement Confidence" series, where we discuss four areas of retirement uncertainty plus strategies designed to replace your anxiety with clarity and control. In part 4, we explore the protection anchors — and how preparing for worst-case scenarios can help you feel more confident through market volatility.  In this episode, you'll learn about:  Why guarante...

554: Freedom After 50: Why Retirement Fear Might Be a Sign You're Ready 13.03.2026

What if the fear you feel about retirement isn't a warning sign, but an invitation to step into a more meaningful, self-directed life?  In this episode, you'll learn:  Why hitting your retirement number can increase anxiety The difference between financial independence and fulfillment Three powerful questions to clarify whether it's time to retire How purpose evolves after work — and why fear ofte...

553: A Step-by-Step Guide to Leverage AI As a Thought Partner & Find Purpose In Retirement with Geoff Woods 09.03.2026

Today, I'm thrilled to finally welcome my friend, Geoff Woods, to the podcast. Geoff is the founder of AI Leadership and The AI-Driven Leadership Collective, the author of The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions , and a leading expert on AI. He previously served as Chief Growth Officer of Jindal Steel & Power, where he played a key role in scaling the company from a $...

552: By the Numbers: The Anchors of Retirement Confidence, Part 3 — Why Tax Flexibility Matters More Than Tax Savings 06.03.2026

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 3, we explore why the biggest threat to your retirement isn't always market volatility, but the taxes you didn't see coming until it was too late.  In this episode, you'll learn:  How tax concentration...

551: Freedom After 50: Why Retirement Decisions Feel Heavier — and What to Do About It 27.02.2026

What if the confidence you're searching for in retirement decisions hasn't disappeared, but has simply been drowned out by noise?  In this episode, you'll learn:  Why retirement decisions feel more emotionally loaded after 50 The difference between useful information and paralyzing overwhelm How anxiety can be a guide; not a warning sign How to rebuild trust in your intuition and inner voice Today...

550: By the Numbers: The Anchors of Retirement Confidence, Part 2 — Building a Plan for the Next Market Crash 20.02.2026

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:  Why market volatility isn't the r...

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