Retire With Purpose - The Retirement Podcast
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...
4 Retirement Risks Your Financial Plan May Be Missing
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...The Secret to a More Connected Retirement
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 yourselfListen in as CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies...
The Retirement Income Strategy That Could Help You Spend More
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 togetherToday's article is from Insurance Newsnet titled, A Hybrid Approach Outperforms the 4% Rule, Researchers Find. Listen in as...
The Art of Living a More Interesting Life in Retirement
Today, I'm excited to welcome Dr. Lorraine Besser to the podcast. Lorraine is a philosopher and author of The Art of Interesting: What We Miss in Our Pursuit of the Good Life and How to Cultivate It. Her work explores what it really takes to live a good life and why happiness and meaning may only be part of the equation.
Retirement is supposed to be the reward for decades of hard work. You finally have more freedom, fewer obligations, and the opportunity to spend your time however you want. But what happens when the retirement you...
The ABCs of a Meaningful Retirement
What if retirement isn't the end of your story, but the beginning of one of its most meaningful chapters? Best-selling author Bruce Feiler explores how to rediscover purpose, identity, connection, and meaning when life — and retirement — takes
an unexpected turn.
In this episode, you'll learn:
Bruce's ABCs of Meaning: Agency, Belonging, and Cause Why retirement can feel like a major "plot twist" How to redefine your identity when your career no longer defines your days How to intentionally create the next chapter of your life A simple exercise you can use to create more meaning start...The Hidden Tax Drag That Could Cost You Millions
The market's return is only part of the story. Find out how taxes can quietly erode your retirement wealth and the planning strategies that can help you keep more of what you've worked so hard to build.
In this episode, you'll learn:
Why tax drag can cost far more than the tax bill you see How asset location can improve your after-tax returns Why the timing of a sale can make a meaningful difference How Roth conversions and capital-gain harvesting can fit into a retirement tax strategy The KEEP framework for thinking about taxes throughout retirement <...The 90-10 Rule: What Really Matters After You Retire
What if the thing you spend 90% of your time planning for before retirement becomes the thing you think about least once you get there? Fritz Gilbert of The Retirement Manifesto joins us to explore the 90-10 rule and why preparing for a fulfilling
retirement requires just as much thought about your life as your money.
In this episode, you'll learn:
How to start planning the non-financial side of retirement Why analytical people can get stuck in endless "what-if" scenarios How to prepare for boredom, isolation, and loss of identity The "spokes" that help create balance...Why Age-Gap Couples Need a Different Retirement Plan
If you and your spouse are several years apart in age — or simply plan to retire at different times — this episode reveals the financial and relationship challenges most couples never anticipate and how to prepare for them.
Listen for insight on:
Why retirement comes in three distinct phases How to create a "retirement operating agreement" as a couple Medicare and healthcare planning pitfalls for age-gap couples Social Security strategies that could impact lifetime income Tax planning opportunities before both spouses retire Practical ways to build a retirement plan that works through every stageListen in as F...
Why Social Connections Are Essential for a Healthy Retirement
Today, I'm excited to welcome Ken Stern to the podcast. Ken is the founder and chair of the Longevity Project, host of Century Lives from the Stanford Center on Longevity, former CEO of NPR, and author of Healthy to 100: How Strong Social Ties Lead to Long Lives. His research explores an aspect of retirement planning that rarely gets enough attention: our social health.
Far too many people spend years wondering whether they've saved enough to retire, but very few think about whether they are socially ready to retire. Work provides much more than a paycheck. It provides...
The U-Curve of Happiness: Why Life Gets Better with Age
What if getting older doesn't mean losing happiness, but gaining more of it? Author Don Ezra explores the surprising science behind the U-curve of happiness and why perspective, purpose, gratitude, and letting go of perfection can make the years
ahead some of your best.
In this episode, you'll learn:
Why happiness often dips in midlife and rises again later in life How dopamine influences our desire for "more" The connection between purpose and life satisfaction A simple exercise for cultivating gratitude and greater life satisfactionListen in as Founder and CEO of Howard Bailey F...
The Market Concentration Myth: Is Your Portfolio Riskier Than You Think?
You may own hundreds of stocks, but that doesn't necessarily mean you're diversified. Discover where concentration risk is really hiding and what you can do about it.
In this episode, you'll learn:
Why owning an S&P 500 index fund may expose you to more concentration risk than you realize. The difference between company concentration and sector concentration Whether international investing actually reduces portfolio risk. Why equal-weight investing is gaining attention in today's market. How to think about highly appreciated individual stock positions before retirement. The one portfolio analysis every retiree should consider.Today's article is from Trend...
The 4 Fundamentals of a Thriving Retirement
Your finances may be ready to enter your second act, but retirement coach Joe Casey explains why the bigger question is whether you've prepared for the life, relationships, health, learning, and fun that come after work.
In this episode, you'll learn:
Why having more free time doesn't automatically create a fulfilling life How retirement can expose gaps in your social life Why your "best Wednesdays" may matter more than your bucket list How to start experimenting with your future before retirement The questions you and your spouse should be asking before you leave workListen...
Should You Stop Saving for Retirement? The Surprising Truth
Could doing everything "right" with your retirement savings actually be limiting your financial freedom?
As part of our "By the Numbers" series, in this episode, you'll learn:
Why "max out your 401(k)" isn't always the right answer The overlooked value of liquidity and accessible cash When you may have already saved enough for retirement How taxes can quietly become one of retirement's biggest expenses Why your retirement plan should support your life; not the other way aroundToday's article is from the Use Your Wealth blog titled You Should Probably Stop Saving for Retirement. Listen in as Fo...
Are You Socially Fit for Retirement?
What if one of the biggest keys to a healthy, meaningful retirement has nothing to do with money? Author and psychology professor Dr. Marc Schulz reveals why your relationships, social connections and "social fitness" may play a surprisingly important role in how well you age — and how you can strengthen them before and during retirement.
In this episode, you'll learn:
How retirement can disrupt your social network Ways introverts and extroverts can approach social fitness differently The "2 a.m. friend" test for evaluating your relationships How couples can navigate different social needs in retirement Dr. Schulz's practi...Die With Zero: Rethinking Wealth, Retirement, and Fulfillment with Bill Perkins
Today, I'm excited to welcome Bill Perkins to the podcast. Bill is an entrepreneur, hedge fund manager, investor, and bestselling author of Die With Zero: Getting All You Can from Your Money and Your Life. Throughout his career, he's challenged one of the most common assumptions about wealth: that accumulating more money should always be the ultimate goal. Instead, Bill encourages people to think differently about how they use their time, health, and financial resources to create a more fulfilling life.
Far too many retirees spend decades building wealth only to discover that saving money is much...
Will Social Security Really Run Out? What Retirees Need to Know
Headlines say Social Security is going bankrupt, but the real story is far more nuanced, and understanding it could help you make smarter retirement decisions before it's too late.
In this episode, you'll learn:
What the latest 2026 Trustee Report reveals Why retirees could still receive benefits, even without Congressional action How AI, longevity, and future productivity could change the outlook The most likely solutions Congress could pursue How to stress test your retirement income plan for multiple Social Security scenariosToday's article is from the Center for Retirement Research at Boston College titled, Social Security's Financial...
The Fear of Running Out vs. The Fear of Missing Out
When it comes to a confident retirement, what if the biggest risk isn't running out of money, but waiting too long to enjoy it? As part of our "Freedom After 50" series, author Mike Drak explores:
Why so many retirees struggle emotionally with spending How retirement spending naturally changes over time The difference between spending on things vs. meaningful experiences How fear of future healthcare costs can hold you back today Practical ways to spend with greater confidence and fewer regretsListen in as Founder and CEO of Howard Bailey Financial, Casey Weade and Mike Drak provide thoughtful insigh...
Long-Term Investing: What Many Retirees Get Wrong
Everyone says to "invest for the long term," but what does that actually mean when you're approaching or living in retirement?
As part of our "By the Numbers" series, in this episode, you'll learn:
Why "long term" means much more than simply waiting How retirement changes the way you should think about investing The psychological cost of staying invested during market downturns Why buying and forgetting isn't a successful investment strategy How to know if you're taking more risk than you actually needToday's article is from the Safal Niveshak blog titled What I Mean When I Say...
The Retirement Exercise That Changes Everything
What if one simple exercise could help you uncover what truly brings you joy, clarify your purpose, and shape a more meaningful retirement?
As part of our "Freedom After 50" series, author Jet Vertz shares:
How the "Lifeline Exercise" helps uncover defining moments in your life Why your happiest moments often reveal your deepest values How to identify the strengths, passions, and experiences that should shape your retirement Why honesty with yourself is essential to creating a retirement filled with meaning instead of simply staying busy A simple reflection exercise you can do on your own, or even with...Why Your Health Is Your Greatest Retirement Asset with Dr. Phil Pearlman
Today, I'm excited to welcome Dr. Phil Pearlman to the podcast. Phil is the founder of the Pearl Institute, a clinical psychologist, former financial executive, and one of the leading voices exploring the intersection of health, behavioral psychology, and long-term performance. Through his writing, coaching, and research, he helps people build healthier lives by focusing on sustainable habits, emotional resilience, and purposeful daily decisions.
After years of success in finance, Phil experienced his own health transformation that completely changed how he thinks about performance, longevity, and fulfillment. Today, he believes one of the biggest blind spots in...
Why Most Stocks Fail (And What Retirees Need to Know)
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 expectations How to think about risk, diversification, and income in retirement The surprising case for Treasury bills and liquidityListen in as Founder and CEO of Howard Bailey Financial, Casey Weade and Bruce...
The Life Transition Every Retiree Must Learn to Master
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 just a life event The three phases everyone experiences during major life transitions How to avoid getting stuck after retirement How couples can navigate retirement transitions together A simple exercise to identify where you are and what y...Is AI Carrying the Entire Stock Market?
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 concentrated market growthToday's article is from the TrendLabs.com titled Would We Be in a Recession Without AI Stocks? Listen in as Founder and CEO of Howard Bailey Financial...
You've Saved for Retirement — So Why Does Spending Still Feel Wrong?
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 retirement Why reaching financial independence doesn't automatically create peace of mind The 3 phases of spending and how expectations often clash with reality Ways to spend with confidence while staying aligned with your valuesToday's artic...
Is Your Social Security Really Worth $1 Million?
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 inflation, taxes, and longevity play in your decision Common misconceptions about Social Security "running out" Practical steps to begin analyzing your own benefits todayToday's article is...
Rethinking the 4% Rule for Today's Retirees with Bill Bengen
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 publication.
Over the past 30 years, Bill has studied hundreds of historical retirement scenarios to better understand how retirees can spend confidently without the fear of running out of money. In his latest book, A Richer Retirement: Supercharging...
The 4 Emotional Phases of Retirement with Fritz Gilbert
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 ways to experiment, reinvent yourself, and find purpose again How retirees can avoid getting stuck in the "lost and loss" phase Why retirement planning should include far more than financesToday's articl...
Hidden Estate Planning Risks Retirees Overlook
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 come down to poor account titling and coordination How trusts can protect children, spouses, and inherited assets from divorce, lawsuits, or poor financial decisionsToday's article is from The Retirement Manifesto titled, Do You Really Need...
Freedom After 50: How to Avoid Retirement Shock and Find Purpose Again with Mike Drak
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 volunteering Author Mike Drak's "late bloomer" philosophy for creating a second act How the Ikigai Method can help retirees uncover meaningful work and purposeListen in as Founder and CEO of Howard Bailey Financial, Casey Weade is...
By the Numbers: Why 42% of Inheritances Disappear Within a Year
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 is essential to a lasting legacyToday's article is from ThinkAdvisor blog titled Heirs Beware: 42% Spend Inheritance Within a Year, Study Finds. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks do...
Signal vs. Noise: How to Make Smarter Retirement Planning Decisions with Jesse Cramer
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 understanding what's actually important for your retirement plan.
Jesse began his career as an aerospace engineer before transitioning into personal finance, combining analytical thinking with clear communication. His work has been...
Freedom After 50: From Bucket List to Life Strategy with Jet Vertz
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 The surprising reason retirees come back to create bigger bucket listsListen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Jet Ver...
By the Numbers: Why Your Tax Refund Isn't What You Think
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 with long-term financial goalsToday's article is from Best Interest blog titled We Are So Irrational (Literally) About Taxes. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtfu...
Freedom After 50: The 80% Rule That Could Change Your Retirement Timeline with Jordan Grumet, MD
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 to determine if you're closer to retirement than you thinkToday's article is from The Purpose Code blog titled, Retire at 80%. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Jo...
By the Numbers: Can You Really Beat the Market by Avoiding the Worst Days?
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 strategies can stabilize retirement outcomesToday's article is from Morningstar titled You Can Beat the Stock Market by Avoiding Its Worst Days. But You Won't. Listen in as Founder and...
How Dopamine Shapes Your Motivation, Happiness, and Purpose in Retirement with Michael Long
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 More: A Step-by-Step Guide to Making Dopamine Work for You. Over the course of his career, he has written speeches for members of Congress, presidential candidates, Fortune 10 CEOs, while also teaching at Georgetown University an...
By the Numbers: The Bucket Strategy vs. 60-40 - Who Really Wins?
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 retirement portfolios How small tweaks can potentially add six figures to your retirementToday's article is from The Retirement Manifesto titled The 60/40 Portfolio vs. The Bucket Strategy. Listen in as Founder and CEO of Howar...
By the Numbers: The Fragile Decade That Could Make (or Break) Your Retirement
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 certainty and protection strategies The psychology of transitioning from growth to preservationToday's article is from ThinkAdvisor.com titled Exploring the Retirement Risk Zone. Listen in as Founder and CEO of Howard...
By the Numbers: Could the Government Tax Your Roth IRA in the Future? What if Congress Changes the Rules?
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 fear — should guide your strategy How to determine if a Roth conversion makes sense for your numbersToday's article is titled Could the Government Tax Your Roth IRA in the Future? Listen in...
By the Numbers: The Anchors of Retirement Confidence, Part 4 — Building a Retirement That Can't Break
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 guaranteed income floors can help improve spending confidence How to manage long-term care as a catastrophic risk How to compare income strategies and trade-offs The power of using home equity as a last-resort safety net How stacking protection anc...