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 ...
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Independentadvisor Podcasts
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540: Freedom After 50: The Quiet Fear Beneath Retirement (and How to Outsmart It)
20:33
20:33
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20:33If 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 fr…
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539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions
30:38
30:38
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30:38Could 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…
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538: Freedom After 50: Why Enough Is a Mindset, Not a Number
25:38
25:38
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25:38What 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…
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537: The Most Overlooked Elements of a Successful Retirement with Fritz Gilbert
1:07:16
1:07:16
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1:07:16Today, 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,…
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536: By the Numbers: Cash Out or Hold On? The Retiree's Dilemma
38:52
38:52
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38:52With 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 Practi…
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535: Freedom After 50: The "Unforgivable Sin" in the Second Half of Life
29:51
29:51
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29:51Discover 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…
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534: By the Numbers: Gold vs. Stocks — What the Data Says About Retirement Portfolios
27:59
27:59
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27:59Gold 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…
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533: By the Numbers: The Case for "Good Enough" — Why Simplicity Often Beats Perfection in Retirement Planning
18:54
18:54
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18:54Could 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. M…
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532: Debunking Advice From Financial "Gurus" to Create An Efficient Retirement Income Plan with David McKnight
1:01:25
1:01:25
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1:01:25Today, 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 …
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531: By the Numbers: Why Retirees Often Spend Too Little, Too Late
26:21
26:21
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26:21Discover 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 regre…
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530: Freedom After 50: How Challenge Rekindles Purpose in Your Next Chapter
26:31
26:31
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26:31What 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 resili…
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529: By the Numbers — Your Financial Wake-Up Call: How to Stop Delaying the Decisions That Matter Most
22:35
22:35
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22:35What'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 "…
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528: Freedom After 50: Finding Peace in the Mystery – Why Financial Control Is an Illusion
36:34
36:34
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36:34The 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…
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527: Challenging the Conventional Wisdom of Stocks vs. Bonds and Common Retirement Planning Strategies with Edward McQuarrie
1:00:07
1:00:07
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1:00:07Today, 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 feat…
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526: Rethinking Social Security: Why Waiting Until 70 Isn't Always Best
30:22
30:22
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30:22What 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…
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525: Freedom After 50: 12 Belief Traps Keeping You from a Meaningful and Impactful Retirement
39:38
39:38
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39:38Retirement 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 …
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524: A New 4-Bucket Approach to Investing Before and After Retirement
23:00
23:00
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23:00You'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 retiremen…
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523: Freedom After 50: Beyond the Pyramid—Rethinking Happiness in Retirement
29:21
29:21
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29:21Many 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 "…
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522: The Six Pillars to Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 2
40:50
40:50
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40:50Living 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 l…
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521: 5 Timeless Proverbs for a Wise and Wealthy Retirement
30:47
30:47
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30:47What 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 Emerge…
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520: The Six Pillars of Living Longer & Healthier in Retirement with Dr. Bobby Dubois - Part 1
1:01:10
1:01:10
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1:01:10Today, 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 C…
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519: Freedom After 50: How to Break Free from Your Old Story and Shape Wisdom That Lasts
28:35
28:35
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28:35Retirement 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 enga…
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518: Beyond Investment Risk: Why Income Risk Could Change Your Retirement Plan
19:21
19:21
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19:21Most 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 Ca…
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517: Freedom After 50: The Need for Next—Finding Meaning Beyond Milestones
32:28
32:28
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32:28Why 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 fo…
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516: Mind the Inflation Gap: Why Forecasts Fail and How to Hedge Smart
21:10
21:10
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21:10Inflation 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 expectati…
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515: The Soul of Wealth: Bridging the Gap Between Money and Happiness with Daniel Crosby, PhD
1:02:05
1:02:05
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1:02:05Today'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 S…
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514: Freedom After 50: You Planned Wisely—But Is Your Money Aligned with What Matters Most?
41:08
41:08
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41:08What 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 art…
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513: The One Big Beautiful Bill Act: What It Really Means for Your Retirement Taxes
49:26
49:26
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49:26What 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 …
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512: Freedom After 50: The Sunk Cost Fallacies Sinking Your Future Vision
27:07
27:07
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27:07Have 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-g…
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511: Sequence Risk Meets RMDs: The Retirement Trap No One Talks About
28:18
28:18
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28:18Are your Required Minimum Distributions (RMDs) setting you up for failure? Find out how sequence of returns risk combines with RMD rules to create a hidden hazard—and how smart planning, asset allocation, and timely Roth conversions can help you sidestep it. In this episode, we discuss: Why RMDs are self-regulating The RMD tax chain reaction Why wi…
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510: Managing Investment Risk When You've Already Won The Game with William Bernstein
53:36
53:36
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53:36Today, I'm speaking with William Bernstein. Bill is a renowned investment advisor, author, and retired neurologist. He's the co-founder of Efficient Frontier Advisors, a leading voice in the world of personal finance, and the author of several acclaimed books, including The Four Pillars of Investing, The Investor's Manifesto, and The Intelligent As…
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509: Freedom After 50: 7 Practices to Help You Stop Hiding and Start Growing
40:04
40:04
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40:04What if your greatest growth in retirement didn't come from doing more—but from finally sitting with who you are? Throughout this discussion, we explore the concept of the "shadow self"—the parts of yourself that you may avoid, hide, or ignore—and how bringing light to these areas can lead to true peace and deeper connection in the second half of l…
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508: More Control, Less Surprise: A Real Retirement Tax Wake-Up Call
23:00
23:00
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23:00What if you did everything "right" in retirement, but were still left surprised? That's exactly what happened to Fritz Gilbert, one of our favorite past podcast guests. In this episode, we unpack his recent article, "My Biggest Surprise in Retirement," and explore why his carefully planned Roth conversions didn't make the impact he expected. This c…
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507: Freedom After 50: You're Not Looking for Advice—You're Looking for Alignment, Part 2
43:19
43:19
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43:19In this powerful follow-up episode, Casey Weade and Certified Retirement Coach Les McDaniel return to explore the deeper question behind advice-seeking: Are you truly looking for direction, or for alignment with your values? Drawing from real-life coaching stories, they unpack six invitations to help you pause, reflect, and realign your financial d…
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506: The Surplus Bucket Strategy: A Way to Spend More Confidently in Retirement
22:56
22:56
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22:56If you're like many retirees we meet with, you may struggle to spend confidently in retirement, even when you've saved enough. Here, we explore a potential strategy: an alternative to the annuity-based "License to Spend" model. In this episode, we discuss: The dynamics of underspending in retirement How to apply the "Funded Status Metric" and "Surp…
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505: Freedom After 50: You're Not Looking for Advice—You're Looking for Alignment, Part 1
28:12
28:12
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28:12Understanding your own story is the missing link between receiving advice and applying it meaningfully. If you've ever felt stuck between wanting direction and feeling overwhelmed by options, this episode offers a practical path toward clarity, purpose, and peaceful resilience. In this episode, we discuss: Advice vs. application A 3-step advice fra…
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504: How to Stay Sharp and Prevent Cognitive Decline in Retirement with Dr. Ross Andel
47:57
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47:57Today, I'm speaking with Dr. Ross Andel. Dr. Andel is a gerontologist, professor, and director of the PhD program at Arizona State University. Ross has spent decades researching aging, memory, and lifestyle-related cognitive health risks. In 2023, he was elected a lifetime fellow of the American Association for his achievements in the study of risk…
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503: Investing at the Sleeping Point: Finding Peace in Your Portfolio
16:41
16:41
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16:41After a sharp rebound in the market, you may still feel the lingering effects of recent volatility. But before the next tide of turmoil, now is an ideal time to deploy the "Sleeping Point" Strategy: adjusting your portfolio to a level where you can sleep soundly at night. In this episode, we discuss: The importance of reducing risk before panic How…
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502: Freedom After 50: The Hidden Cost of Delayed Gratification in Retirement
28:04
28:04
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28:04You're encouraged to save, delay gratification, and be disciplined with your spending—but what happens when that mindset becomes a roadblock in retirement? In this episode, we discuss: The psychology of postponement How to unwind a lifetime of discipline The "Joy Budget" concept Tools to reframe spending Today's article is from The Wall Street Jour…
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501: The Four Futures of Retirement: Which Path Are You On?
24:17
24:17
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24:17What does your future retirement look like? Whether your path includes unexpected challenges, careful frugality, or joyful surprises, it's vital to prepare for known unknowns, and build a resilient future that adapts to life's curveballs. In this episode, we discuss: Why retirement isn't linear How to plan for different potential retirement futures…
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500: Freedom After 50: 6 Crucial Signs You're Ready for a New Direction
38:38
38:38
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38:38Do you ever experience those moments when something doesn't feel quite right? Your body and spirit have ways of alerting you when it's time for recalibration, often with persistent whispers that grow louder the longer you ignore them. In this episode, we discuss: The power of listening to your intuition Daily actions that can reconnect you to your …
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499: Retirement Income Strategies to Quell Inflation Fears and Spend Comfortably with David Blanchett
57:04
57:04
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57:04Today, I'm thrilled to welcome David Blanchett back to the podcast. David is the Managing Director and Head of Retirement Research at PGIM DC Solutions and one of the most respected voices in retirement income planning today. You've likely come across his work in Morningstar, Kiplinger, and our Weekend Reading series—and for good reason. His resear…
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498: 4 Ways to Cultivate Character Amid Market Chaos
25:22
25:22
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25:22How can you use the recent market crisis to refine both your portfolio and your character? In this episode, we discuss: Why times of turmoil are opportunities for personal growth How to reinterpret stressors as forward-thinking steps Inaction vs. action: How to decide which is best for your portfolio amidst times of turmoil Today's article is from …
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497: Freedom After 50: 5 Numbers Stealing Your Time, Wealth, and Joy
38:54
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38:54True financial and personal well-being requires alignment between your money, values, and purpose. But how do you bridge the gap between merely accumulating wealth and living a life rich with meaning? In this episode, we discuss: The 50/30/20 Rule and how to align it with your values Debt ratios: Is your debt for survival or for status? Meaningful …
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496: Claiming Social Security Early: Is it the Right Strategy for You?
22:46
22:46
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22:46Conventional financial wisdom encourages you to delay collecting Social Security benefits until age 70, but in certain cases, your "optimal" claiming age might actually be to pull benefits early. In this episode, we discuss: Factors that benefit filing early Your "breakeven" number of filing early vs. later How your rate of return should factor int…
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495: Freedom After 50: The World is Ending… What's Next?
34:58
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34:58If you saw the amount of time you had left to live—whether it was one day or one year—how would you spend it? What would you worry about? In this episode, we discuss: How to let go of always trying to control your narrative Why the pursuit of contentment is greater than the pursuit of happiness 5 questions to help you find pure contentment in the p…
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494: Beyond the Headlines: How Retirees Can Navigate Investment Risks with Larry Swedroe
1:08:36
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1:08:36Today, I'm speaking with Larry Swedroe. Larry is the former Chief Research Officer at Buckingham Strategic Wealth, an accomplished author with 18+ books on investing, and a true pioneer in evidence-based investing. He's also a well-known advocate for cutting through the financial media noise to focus on strategies that actually work. In Larry's lat…
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493: Chaotic Markets: A 4-Point Checklist to Safeguard Your Retirement Savings
27:45
27:45
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27:45Are you feeling uneasy right now? If market turmoil is causing you stress, it's time to determine if your retirement plan is truly built for the unexpected. In this episode, we discuss: How a process can give you greater investment and financial control How to assess your liquid/safe reserves Tax and inflation protection opportunities brought by ma…
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492: 3 Levels of Retirement Readiness: Where Do You Stand?
23:07
23:07
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23:07How would you rate yourself on the retirement readiness scale? When you understand where you are and how to proceed, you are more likely to feel elevated confidence to and throughout retirement. In this episode, we discuss: Financial vs. non-financial retirement readiness Why your income strategy is key Considerations for long term care insurance H…
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491: Freedom After 50: 8 Reasons the Month You Retire Matters
32:28
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32:28Before you make your transition into retirement, it's important to dial in the ideal timing not just for your money, but your mind. In this episode, we discuss: Irrational reasons to not retire The "3 Cs" of retirement timing Family, health, and social considerations in retirement Listen in as Casey Weade is once again joined by Les McDaniel to exp…
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