Retire With Purpose - The Retirement Podcast - podcast cover

Retire With Purpose - The Retirement Podcast

Casey Weaderetirewithpurpose.com
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 make better financial decisions so you can live the lifestyle you've always imagined and deserve. Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations. ©2024 HOWARD BAILEY FINANCIAL, INC.
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Episodes

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 Freedom After 50: Why Change Feels So Hard and How WiseWealth Helps You Face It . Listen in as Founder and...

Aug 08, 202541 minEp. 514

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 seniors Social Security misconceptions New "below-the-line" deductions Today's article is from the Kitces...

Aug 01, 202549 minEp. 513

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 what might be holding you back—and, more importantly, how to move forward. In this episode, we discuss...

Jul 25, 202527 minEp. 512

511: Sequence Risk Meets RMDs: The Retirement Trap No One Talks About

Are 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 withdrawal timing and asset allocation matters The power of Roth conversions Today's article is from the Best Interest blog titled, RMDs + Sequence Risk...

Jul 18, 202528 minEp. 511

510: Managing Investment Risk When You've Already Won The Game with William Bernstein

Today, 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 Asset Allocator . With a unique background in neurology and finance, Bill brings a practical and evidence-based perspective to long-term investing, risk...

Jul 14, 202554 minEp. 510

509: Freedom After 50: 7 Practices to Help You Stop Hiding and Start Growing

What 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 life. In this episode, we discuss: How unresolved emotional patterns can impact health, relationships, and joy Why it's important to take inventory of ...

Jul 11, 202540 minEp. 509

508: More Control, Less Surprise: A Real Retirement Tax Wake-Up Call

What 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 conversation is for anyone who wants to stay in the driver's seat—no surprises, no backseat driving from Uncle Sam—just thoughtful, purpose-driven plan...

Jul 04, 202523 minEp. 508

507: Freedom After 50: You're Not Looking for Advice—You're Looking for Alignment, Part 2

Casey Weade and Les McDaniel delve into the concept of seeking alignment over mere advice in financial and life planning, emphasizing that true peace comes from aligning financial decisions with personal values. They explore practical strategies like asking better questions, cultivating emotional awareness, and identifying the deeper meaning behind financial goals. The discussion highlights the importance of introspection and collaboration to create a truly purposeful retirement.

Jun 27, 202543 minEp. 507

506: The Surplus Bucket Strategy: A Way to Spend More Confidently in Retirement

If 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 "Surplus Bucket" to your income plan Pros and cons of leveraging this strategy A refresher of the "Funded Ratio" How to find an income strategy that aligns...

Jun 20, 202523 minEp. 506

505: Freedom After 50: You're Not Looking for Advice—You're Looking for Alignment, Part 1

Casey Weade and Les McDaniel discuss why generic advice often falls short, highlighting the problem of incomplete context and advice overload. They propose a three-step framework for seeking advice that prioritizes understanding your own life story and values, helping individuals resist societal pressures for "more" and achieve peaceful resilience. The conversation extends beyond financial gains to define true wealth through health, relationships, and purposeful living.

Jun 13, 202528 minEp. 505

504: How to Stay Sharp and Prevent Cognitive Decline in Retirement with Dr. Ross Andel

Today, 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 factors for age-related cognitive decline for Alzheimer's disease and other types of dementia. Dr. Andel explains how daily routines and purpose dire...

Jun 09, 202548 minEp. 504

503: Investing at the Sleeping Point: Finding Peace in Your Portfolio

After 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 to embrace proactive planning The danger of over-investing How (and when) to stress test your portfolio Today's article is from Pearl's Prime Cuts bl...

Jun 06, 202517 minEp. 503

502: Freedom After 50: The Hidden Cost of Delayed Gratification in Retirement

You'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 Journal titled, The Downside of Delayed Gratification. Listen in as Founder and CEO of Howard Bailey Financial , Casey Weade is joined by Les McDaniel to ...

May 30, 202528 minEp. 502

501: The Four Futures of Retirement: Which Path Are You On?

What 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 Lifequakes vs. Deep Risk The PESTLE framework for strategic thinking Today's article is from Kiplinger titled, The 'Rule of Four Futures' in Retireme...

May 23, 202524 minEp. 501

500: Freedom After 50: 6 Crucial Signs You're Ready for a New Direction

Do 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 purpose How negativity impacts you physically The importance of recognizing simple joys Today's article is from our very own blog post titled, When Li...

May 16, 202539 minEp. 500

499: Retirement Income Strategies to Quell Inflation Fears and Spend Comfortably with David Blanchett

Today, 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 research has earned accolades from nearly every major financial planning organization. In our conversation, we picked up where we left off back in Episode 5...

May 12, 202557 minEp. 499

498: 4 Ways to Cultivate Character Amid Market Chaos

How 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 Forbes titled, Waiting Wisely: Cultivating Character Amid Market Chaos . Listen in as Founder and CEO of Howard Bailey Financial , Casey Weade, breaks...

May 09, 202525 minEp. 498

497: Freedom After 50: 5 Numbers Stealing Your Time, Wealth, and Joy

True 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 vs. meaningless time in retirement The Satisfaction Ratio and how it can help you live a more joyful life Today's article is from Mr-Stingy titled, Th...

May 02, 202539 minEp. 497

496: Claiming Social Security Early: Is it the Right Strategy for You?

Conventional 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 into your Social Security strategy Today's article is from Vanguard titled, Social Security: For Some, Early Claiming is Better. Listen in as Founder and...

Apr 25, 202523 minEp. 496

495: Freedom After 50: The World is Ending… What's Next?

If 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 present Listen in as Founder and CEO of Howard Bailey Financial , Casey Weade is joined by Les McDaniel to run through 5 questions that will help you f...

Apr 18, 202535 min

494: Beyond the Headlines: How Retirees Can Navigate Investment Risks with Larry Swedroe

Today, 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 latest book, Enrich Your Future: The Keys to Successful Investing , he distills decades of financial wisdom into 40 powerful stories that make investing ...

Apr 14, 20251 hr 9 minEp. 494

493: Chaotic Markets: A 4-Point Checklist to Safeguard Your Retirement Savings

Are 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 market volatility Today's article is from Morningstar titled, What Now? An Investor's To-Do List for Chaotic Markets. Listen in as Founder and CEO of Ho...

Apr 11, 202528 minEp. 493

492: 3 Levels of Retirement Readiness: Where Do You Stand?

How 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 How to prepare for financial change in retirement Today's article is from The Retirement Manifesto titled, 3 Levels of Retirement Readiness: Where Do Y...

Apr 04, 202523 minEp. 492

491: Freedom After 50: 8 Reasons the Month You Retire Matters

Before 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 explore the common irrational fears about retiring. To receive your FREE WISE Wealth Assessment worksheet, text WISE to 888-599-4491 Show Notes: Howardba...

Mar 28, 202532 minEp. 491

490: Retirement Withdrawal Strategies in Down Markets: Should You Shift Yours?

Market volatility is inevitable. Whether you're 10 months or 10 years into retirement, it's vital to ask: is your investment strategy prepared? In this episode, we discuss: Why market volatility is necessary When down markets no longer become an opportunity How to avoid sequence of returns risk 4% withdrawal rule flaws Today's articles are from The Best Interest blog titled, Should I "Reset" Retirement Withdrawals in Bad Markets? and Are You Not Entertained?! Listen in as Founder and CEO of Howa...

Mar 21, 202527 minEp. 490

489: Freedom After 50: The 4 Myths of Security Keeping You Stuck Today and Fearful of Tomorrow

For decades, you've been told that security is the key to a successful life; Work hard, save wisely, and one day, you'll be able to retire with peace of mind. But what if the very idea of security is holding you back? In this episode, we discuss: The power of a decision-making framework Pitfalls of delayed gratification Financial security disillusions Listen in as Casey Weade is once again joined by Les McDaniel to discuss challenges to the traditional notion of security as the key to a successf...

Mar 14, 202527 minEp. 489

488: From Accumulating to Spending: 20 Lessons for a Happy & Successful Retirement with Christine Benz

Today, I'm very excited to welcome Christine Benz back to the podcast. Christine is the Director of Personal Finance and Retirement Planning at Morningstar. She has become a trusted voice in the industry and has been recognized as one of Barron's Top 100 Most Influential Women in Finance and one of the Ten Most Influential Women in Wealth Management. She's also the co-host of The Long View and How to Retire podcasts where she brings a wealth of expertise and real-world insight to every conversat...

Mar 10, 20251 hr 1 minEp. 488

487: Should You Pay Off Your Mortgage Before Retirement?

Is it OK for you to bring debt into retirement? More specifically, what about your mortgage? To gain clarity, you must approach this decision from a financial and emotional perspective. In this episode, we discuss: Historical vs. potential future of mortgage rates Why a mortgage can be a valuable asset How to determine your mortgage value Today's article is from A Wealth of Common Sense titled, Should You Pay Off Your Mortgage Before Retirement? Listen in as Founder and CEO of Howard Bailey Fina...

Mar 07, 202527 minEp. 487

486: Freedom After 50: How to Talk About the Tough Stuff—Money, Religion & Politics

In retirement and beyond, strong social connections are at the heart of human happiness and fulfillment. But to create those solid relationships, you often need to learn how to dig deeper with your conversations. In this episode, we discuss: Why quality of relationships is crucial for longevity and happiness How the "Coin's Edge" philosophy helps you understand other points of view The importance of curiosity for growth How to have deeper conversations with the TALK acronym Today's article is fr...

Feb 28, 202531 minEp. 486

485: Top 5 Retiree Regrets and How to Avoid Them

You want to ensure you have all your ducks in a row before entering retirement. Today, we're pulling back the curtain on the biggest retiree regrets so that they don't become yours too. In this episode, we discuss: Do you need to be a millionaire to retire? The Social Security "breakeven" number Pros and cons of bringing debt into retirement Preparing for a forced retirement Today's article is from The Retirement Manifesto titled, 5 Top Regrets of Retirees (and how to avoid them). Listen in as F...

Feb 21, 202526 minEp. 485
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