Retire With Purpose - The Retirement Podcast
Retire With Purpose is a retirement-focused podcast hosted by Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and CEO of Howard Bailey Financial. Each episode features conversations with financial and retirement experts, along with discussion of current topics that can affect listeners' finances. The show aims to help people build financial confidence and fulfillment whether they are already retired or still preparing for retirement. It offers strategies intended to support better financial decisions and the pursuit of a desired lifestyle. The podcast is produced in the United States.
Episodes
591: 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
590: 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"
589: 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 differe
588: 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
587: 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
586: 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 y
585: 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 des
584: 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 actual
583: 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 Wednesda
582: 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 e
581: 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 retire
580: 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
579: 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 outloo
578: 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 health
577: 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 fo
576: 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 tha
575: 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, emo
574: 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
573: 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 ju
572: 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 con
571: 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 ret
570: 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 inf
569: 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
568: 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
567: 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
566: 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 volun
565: 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
564: 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
563: 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 throug
562: 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 wi
561: 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
560: 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 strateg
559: 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 M
558: 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 ret
557: 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
556: 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
555: 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 guarant
554: Freedom After 50: Why Retirement Fear Might Be a Sign You're Ready
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 oft
553: A Step-by-Step Guide to Leverage AI As a Thought Partner & Find Purpose In Retirement with Geoff Woods
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 $7
552: By the Numbers: The Anchors of Retirement Confidence, Part 3 — Why Tax Flexibility Matters More Than Tax Savings
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
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
550: By the Numbers: The Anchors of Retirement Confidence, Part 2 — Building a Plan for the Next Market Crash
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
549: Freedom After 50: The Hidden Link Between Your Money Habits and Your Life
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: How investing principles translate into life decisions Using stress and uncertainty as tools instead of threats Why margin of safety matters beyond your portfolio The difference between being rich and bei
548: Conscious Aging: Finding Meaning, Purpose, and Growth in Retirement with Ron Pevny
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 passag
547: By the Numbers: The Anchors of Retirement Confidence, Part 1 — Finding Your Sustainable Spending Range
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: Why safe withdrawal "rules" can create unnecessary stress How to find your personal sustainable spendin
546: 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 reg
545: 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 prot
544: 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 c
543: 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 fo
542: 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 b
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 retirem
540: 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
539: 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
538: Freedom After 50: Why Enough Is a Mindset, Not a Number
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: Why "having enough" is both a financial and emotional question When saving "too well" creates new problems The FIRE movement cautionary tale The role of curiosity, creativity, and craft in a purposeful retirement Today's article is from The Root o
537: The Most Overlooked Elements of a Successful Retirement with Fritz Gilbert
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
536: By the Numbers: Cash Out or Hold On? The Retiree's Dilemma
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: Reasons why you might reduce stock exposure Poor (or dangerous) reasons to move to cash The biggest threat to your portfolio Practical investment frameworks to leverage in today'
535: Freedom After 50: The "Unforgivable Sin" in the Second Half of Life
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: Why certainty "hardens" as we age How to navigate generational divides How fear shapes our beliefs and actions Viewing values as flexible filters vs. rigid rules Today's article is from our very own blog titled, The "Unfo
534: By the Numbers: Gold vs. Stocks — What the Data Says About Retirement Portfolios
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: Gold's big run Historical data of gold vs. equity returns Inf
533: By the Numbers: The Case for "Good Enough" — Why Simplicity Often Beats Perfection in Retirement Planning
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: The myth of the "perfect" portfolio Satisficers vs. Maximizers The Boglehead Paradox Your life's
532: Debunking Advice From Financial "Gurus" to Create An Efficient Retirement Income Plan with David McKnight
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 au
531: By the Numbers: Why Retirees Often Spend Too Little, Too Late
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: Pitfalls of traditional retirement income plans What to know about the "retirement spending smile" Spending regret factors for retirees Health and longevity per
530: Freedom After 50: How Challenge Rekindles Purpose in Your Next Chapter
What if the key to a fulfilling retirement isn't about relaxation — but about doing the hard things you'd rather avoid? From rewiring your brain to deepening your sense of purpose, discover how challenges — big or small — can restore meaning, resilience, and joy in your next chapter of life. In this episode, we discuss: Why comfort can erode resilience How to leverage "controlled challenges" Wa
529: By the Numbers — Your Financial Wake-Up Call: How to Stop Delaying the Decisions That Matter Most
What's really holding you back from taking that next financial step? Join us as we explore how avoidance slowly erodes confidence, why shame and fear create roadblocks, and how to replace procrastination with purposeful progress. In this episode, we discuss: Why avoidance = erosion, not explosion The Hurricane vs. Tornado analogy How to conduct a "Shame Audit" Why small steps can create big fin
528: Freedom After 50: Finding Peace in the Mystery – Why Financial Control Is an Illusion
The belief that more data equals more control is an illusion. Our obsession with finding the "perfect" financial plan and receiving constant information often leads to anxiety, not peace. Join us as we explore why embracing uncertainty, focusing on what you can control, and leading with purpose can help create true financial (and emotional) freedom. In this episode, we discuss: How to balance c
527: Challenging the Conventional Wisdom of Stocks vs. Bonds and Common Retirement Planning Strategies with Edward McQuarrie
Today, I'm speaking with Edward McQuarrie. Ed is the Professor Emeritus at Santa Clara University, where he taught in the marketing department for more than three decades before retiring in 2016. After stepping away from teaching, Ed pursued a new passion in researching financial market history and retirement income planning. His work has been featured in the Wall Street Journal, MarketWatch, and
526: Rethinking Social Security: Why Waiting Until 70 Isn't Always Best
What if the common advice to wait until age 70 for Social Security isn't always the best move? Could claiming earlier actually give you more freedom and peace of mind in retirement? In this episode, we discuss: Risks of "blanketed" Social Security advice Determining your expected value vs. expected utility Mortality, sequence of returns, and policy risks Pinpointing your "personalized discount
525: Freedom After 50: 12 Belief Traps Keeping You from a Meaningful and Impactful Retirement
Retirement is about more than finances — it's about meaning and growth. Join us as we explore common "belief traps" that can hold you back, how to reframe your story, and expand what's possible in the years ahead. In this episode, we discuss: How the echo chamber and certainty traps limit perspective and growth Why the comfort trap keeps you stuck — and how to break free The danger of the perfe
524: A New 4-Bucket Approach to Investing Before and After Retirement
You're told to shift from "growth" to "protection" the moment you retire and leave the workforce. But is it really that simple? Join us as we break down the false dichotomy of pre- vs. post-retirement investing, showing why your strategy should always include a mix of offense and defense. In this episode, we discuss: Your biggest risks in retirement How to leverage all your assets (stocks, bon
523: Freedom After 50: Beyond the Pyramid—Rethinking Happiness in Retirement
Many of us spend decades climbing Maslow's pyramid — seeking security, comfort, and experiences — only to realize that the top is where true joy lives. Join us as we explore the "Happiness Hierarchy" and why lasting fulfillment comes not from what you buy or where you travel, but from who you become. In this episode, we discuss: How to shift from "having enough" to "becoming more" Why Maslow's
522: The Six Pillars to Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 2
Living longer is one thing. Living well is another. In Part 2 of my conversation with Dr. Bobby Dubois, we unpack the final three pillars of his blueprint for longevity: mind-body harmony, heat & cold exposure, and social relationships. Dr. Bobby explains why practices like meditation, breathwork, and even walking in nature can calm the brain and lower anxiety. We also explore the science-backed b
521: 5 Timeless Proverbs for a Wise and Wealthy Retirement
What can ancient wisdom teach us about modern retirement? From budgeting with freedom to preparing for life's surprises, tackling debt, planning wisely, and redefining generosity in retirement, insights of the past can show how true wealth goes beyond dollars. In this episode, we discuss: The importance of having a budget, even in retirement Emergency fund: How much do you need? Debt and depend
520: The Six Pillars of Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 1
Today, I'm speaking with Dr. Bobby Dubois. Dr. Bobby is a Harvard-educated physician, Board-Certified in Internal Medicine with over 25 years of experience. He's an author, entrepreneur, wellness doctor, and Ironman Triathlete. Most recently, he led a health policy research organization in Washington, D.C. (National Pharmaceutical Council) as its Chief Science Officer and Executive Vice President.
519: Freedom After 50: How to Break Free from Your Old Story and Shape Wisdom That Lasts
Retirement isn't the end — it's your greatest opening. Join us as we explore how to break free from old stories, embrace wisdom, and turn life's challenges into a legacy of meaning and impact. In this episode, we discuss: Why lifequakes = growth Fluid vs. crystallized intelligence How to redefine success in retirement The role of curiosity and engagement Today's article is from our very own b
518: Beyond Investment Risk: Why Income Risk Could Change Your Retirement Plan
Most financial plans focus on how your investments perform, but what about the risks to your income along the way? Join us as we unpack groundbreaking research that shows why traditional retirement calculators and rules of thumb may be leaving you exposed. In this episode, we discuss: Traditional planning gaps The three types of income risk Risk Capacity vs. Need vs. Attitude Retirement "buf
517: Freedom After 50: The Need for Next—Finding Meaning Beyond Milestones
Why do so many retirees struggle to find fulfillment after leaving the workforce, and how do they break free from the traps of status, constant pleasure-seeking, and busywork? Together, we unpack practical strategies for moving beyond milestones to craft a retirement rich in purpose, connection, and legacy. In this episode, we discuss: The "need for next" mindset Five common non-financial retir
516: Mind the Inflation Gap: Why Forecasts Fail and How to Hedge Smart
Inflation is unpredictable—and it doesn't care what the experts think. Join us as we explore why traditional forecasting fails, how real assets like real estate and commodities can act as powerful inflation hedges, and whether Bitcoin truly deserves its "digital gold" title. In this episode, we discuss: Consumer vs. professional inflation expectations What it means to leverage "Real Assets" as
515: The Soul of Wealth: Bridging the Gap Between Money and Happiness with Daniel Crosby, PhD
Today's guest is Dr. Daniel Crosby, a leading psychologist and behavioral finance expert who helps individuals and organizations understand how our thoughts, emotions, and behaviors intersect with the markets—and ultimately, our sense of purpose. He serves as Chief Behavioral Officer at Orion Advisor Solutions and is the bestselling author of The Soul of Wealth: 50 Reflections on Money and Meanin
514: Freedom After 50: You Planned Wisely—But Is Your Money Aligned with What Matters Most?
What if true wealth isn't just about how much you've saved, but how wisely you're living? Join us as we explore the WiseWealth Matrix, a tool built on six life "currencies" that go far beyond money. In this episode, we discuss: The WiseWealth Framework Wealth vs. Wisdom currencies The 4 zones of the Matrix And, an exciting announcement! Today's article is from our very own blog post titled Fre
513: The One Big Beautiful Bill Act: What It Really Means for Your Retirement Taxes
What does the "One Big Beautiful Bill Act" mean for your retirement? Find out how the latest tax legislation—from permanent TCJA extensions to surprising changes in charitable giving, Social Security taxation, 529 plan use, and more—could affect your tax strategy for years to come. In this episode, we discuss: Updated inflation adjustments Capital gains nuance Enhanced standard deduction for seni
512: Freedom After 50: The Sunk Cost Fallacies Sinking Your Future Vision
Have you ever held on to something just because you've "put too much into it to let it go"? Many of us fall into the sunk cost fallacy trap—the quiet force that keeps us tied to the past. Whether it's a house full of memories that no longer fits your lifestyle, a career that defined your identity for decades, or a friendship that's no longer life-giving, this conversation will help you identify
