Retiring from a job vs. retiring from work

What’s next?

Don’t drift. Design.

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Most retirement planning conversations start and end with money. Rod Yancy, founder of Oath Planning, challenges that assumption head-on — arguing that mindset, emotional health, and identity matter more than any portfolio balance when it comes to actually thriving in retirement. In this conversation, Rod shares data from Oath’s latest client survey, their Q1 2026 Money and Meaning Institute survey of over 500 retirees and near-retirees, and some the findings may surprise you. For example, the biggest regrets aren’t about money. The financial advisory industry is structurally incentivized to keep money at the center of retirement planning — even when that leaves clients less than fully prepared for what they’ll face in planning for life in retirement. He offers a candid, practitioner-level view of what he actually sees working (and failing) in retirement transitions.

Rod Yancy joins us from Tulsa, Oklahoma.

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Bio

Rod Yancy is a multifaceted entrepreneur, writer, attorney, and leader. His personal mission to empower others to live their lives to the fullest is woven into both his business ventures and creative projects.

After graduating from the University of Oklahoma in 2002 with a double major in philosophy and political science, Rod made adventure his top priority, traveling in search of new experiences, inspiration, and deeper meaning. He began writing about his journeys while immersing himself in diverse fields, from mindfulness to literature to software development.

Recognizing the importance of legal expertise for his entrepreneurial goals, Rod pursued a J.D. at the University of Oklahoma College of Law, graduating in 2006. He quickly put his education to use by founding two app-based software companies in fantasy sports and photo sharing, before shifting his focus to creating what became one of his life’s major undertakings – Oath.

Since its inception in 2010, Oath Law has been guided by Rod’s belief that life is short and everyone should embrace their unique journey to achieve their full potential. With this perspective, Rod utilized estate planning as a means to help people recognize life is short and organize their affairs, allowing them to focus on what truly matters: enjoying life.

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For More on Rod Yancy

Oath Planning

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Retirement Podcast Conversations You May Like

Retire with Purpose – Cesar Aguirre

Design a Phased Retirement – Anna Rappaport

Coming of Age in Retirement – Tom Marks

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About The Retirement Wisdom Podcast

There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time.

About Retirement Wisdom

I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident.

Schedule a call today to discuss how the Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one — on your own terms.

About Your Podcast Host

Joe Casey is an executive coach who helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a 26-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking.

Joe has earned Master’s degrees from the University of Southern California in Gerontology (at age 60), the University of Pennsylvania, and Middlesex University (UK), a BA in Psychology from the University of Massachusetts at Amherst, and his coaching certification from Columbia University.

In addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, ranked in the top 1% globally in popularity by Listen Notes, with over 1.6 million downloads. Business Insider recognized Joe as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy.

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Wise Quotes

On Mindfulness 

“I remember hearing when I was young, about a farmer whose crops had failed. And when they asked him what he would have done different, he said I would have cared for the soil sooner. And that that really is the thing. Oftentimes, we really don’t care for what matters until after it’s too late to fix it. And I think that when it comes to emotional well being and mindfulness, people sometimes don’t even know what they were missing. But when we sit down with our clients who are retirees, we see clearly that their mindset does shape their experience in retirement even more than money.”

On Resilience

“Oftentimes, resilience determines whether the change going into retirement feels like freedom, or feels like a loss of identity. And their purpose or what they what they mean to do with their life can make their calendar either feel very empty or open for for better things for them to do.  I don’t know if it’s counterintuitive, but I just keep seeing it time and time again, that people really need to pay attention to who they are before retirement.”

On Taking Aim in Retirement

“A man without an aim or a woman without an aim…is just that drifting. Taking aim at something is really important even in retirement. I think that is where you find the peace and that’s where you find that purpose.”

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