Retire With Purpose - The Retirement Podcast

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 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.

Episodes

October 3, 2025 39 mins

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 perfection and irrelevance traps in ...
Mark as Played

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, bonds, pensions, Social Security, ...
Mark as Played

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 hierarchy is often misundersto...
Mark as Played

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 benefits of sauna and cold plunging—...

Mark as Played

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 dependence
  • Generosity in retirement: ...
Mark as Played

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.

Prior to that, he served as the Ch...

Mark as Played

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 blog post titled, Freedom A...

Mark as Played

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 “buffering”
  • The Retirement Red Zone
  • ...

Mark as Played

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 retirement traps
  • The “good enough” p...
Mark as Played

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 a hedge
  • Why equities still mat...
Mark as Played

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 Meaning. He’s been recognized by AARP and...

Mark as Played

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 ...

Mark as Played

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 misconcepti...
Mark as Played

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 ...

Mark as Played

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
Mark as Played

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 prac...

Mark as Played

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...
Mark as Played

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 bac...

Mark as Played

In 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 decisions with your life’s purpose.  

In this episode, we discuss: 

  • How to ask be...
Mark as Played

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...
Mark as Played

Popular Podcasts

    I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

    Cardiac Cowboys

    The heart was always off-limits to surgeons. Cutting into it spelled instant death for the patient. That is, until a ragtag group of doctors scattered across the Midwest and Texas decided to throw out the rule book. Working in makeshift laboratories and home garages, using medical devices made from scavenged machine parts and beer tubes, these men and women invented the field of open heart surgery. Odds are, someone you know is alive because of them. So why has history left them behind? Presented by Chris Pine, CARDIAC COWBOYS tells the gripping true story behind the birth of heart surgery, and the young, Greatest Generation doctors who made it happen. For years, they competed and feuded, racing to be the first, the best, and the most prolific. Some appeared on the cover of Time Magazine, operated on kings and advised presidents. Others ended up disgraced, penniless, and convicted of felonies. Together, they ignited a revolution in medicine, and changed the world.

    Crime Junkie

    Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

    The Breakfast Club

    The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

    Stuff You Should Know

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.