PodcastsEducationThe Retirement Wisdom Podcast

The Retirement Wisdom Podcast

Retirement Wisdom
The Retirement Wisdom Podcast
Latest episode

148 episodes

  • The Retirement Wisdom Podcast

    What Can Make or Break Your Retirement – Rod Yancy

    2026-03-05 | 23 mins.
    What’s next?

    Don’t drift. Design.

    Our next small group coaching program starts in April.

    Learn more here.

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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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  • The Retirement Wisdom Podcast

    Retiring Soon? What No One Tells You – Michael Kay

    2026-03-02 | 35 mins.
    What’s next?

    Don’t drift. Design.

    Our next small group coaching program starts in April.

    Learn more here.

    _________________________

    Who are you when you’re no longer your title? For many high-performing professionals, that question can feel destabilizing — even frightening.

    Michael Kay is a CFP, a financial life planner, the author of the new book How To Craft Your Chapter X: A Guide For High-Performing Men to Discover Meaning (and Joy) In Retirement. He’s been through it himself—the excitement of the new chapter, and then, six months in, the wall he didn’t see coming.

    Today he shares what he’s learned about reopening the aperture, grieving what you’ve left behind, and finding out who you were before you were your job. This is a conversation every high-achieving man—and the people who love them—needs to hear.

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    Bio

    Michael F. Kay is a coach, teacher, author and retired CFP(R). Through his books, workshops, speeches, and the Chapter X community, he’s helped thousands of women, men, and families master their financial lives—and navigate the transition from full-time work to what comes next.

    He’s written three books: How to Craft Your Chapter X, The Feel Rich Project, and The Business of Life. His insights have been featured in The New York Times, The Wall Street Journal, Fox Business, Forbes, and Psychology Today. Today, he publishes weekly essays for the Chapter X newsletter, hosts the Chapter X podcast, and shares his thoughts on LinkedIn. He is the former president of Financial Life Focus, a fee-only multi-advisor financial life planning firm.

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    For More on Michael Kay

    How To Craft Your Chapter X: A Guide For High-Performing Men to Discover Meaning (and Joy) In Retirement

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    Podcast Conversations You May Like

    The Inspired Retirement – Nathalie Martin

    How to Prepare Mentally for Life After Work – Joseph Maugeri

    Art Cure: The Science of How the Arts Save Lives – Daisy Fancourt

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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 Saying No in Retirement

    “If it’s not joyful, I’m not going to do it.”

    On Perspective

    “As we get older and we start focusing towards career, that aperture narrows. And so when we get ready to step into this next chapter, whether it’s our choice or not, we are at our narrowest. So we need to, mindfully and intentionally—I think that’s the right word—look to reopen that aperture.”

    On Returning to Music – For Fun

    “I got the trumpet out and had it cleaned, and I found a teacher, and I started playing again, and I put up on my music stand, ‘fun’—the word fun—to remind me. Because if you miss a note, I was like, ‘You suck.’ All these things that come back. And so I had to keep reminding myself: this is for fun. I am never going to be a touring professional musician. I’m never going to play with Blood, Sweat and Tears or Chicago. This is for fun. And it just takes the discipline to keep reminding yourself—have joy in the music, have joy in the doing. The joy is in the journey, not in the destination. Because the destination is the journey.”
  • The Retirement Wisdom Podcast

    The ‘One More Year’ Trap – Zach Morris, CFP

    2026-02-26 | 25 mins.
    Don’t plan for just one side of retirement.

    Design Your Life in Retirement.

    Join our small group coaching program beginning in April.

    Learn more here.

    Very Early Registration Discount ends on March 1st. Sign up here.

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    What if the biggest risk in retirement isn’t the market — but misunderstanding your own goals?

    As you approach retirement, the questions shift. It’s no longer just “How much have I saved?” It becomes, “When do I want the freedom to retire?” “How much risk do I really need to take?” And perhaps most importantly — “What is my money for?”

    Today, I’m joined by financial planner Zach Morris for a candid conversation about risk tolerance versus risk capacity, sequence of return risk, working one more year, helping family, and why having a 100% probability of financial success might actually mean you’re leaving life on the table.

    If you’re within five years of retirement — or wondering whether you’re truly ready — this episode will help you think differently about risk, purpose, and pulling the trigger.

    Zach Morris, CFP joins us from Atlanta.

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    Bio

    Having traveled to over 35 countries, Zach is a believer in Ralph Waldo Emerson’s statement that Life is about the journey, not the destination. Being a CERTIFIED FINANCIAL PLANNER® provides Zach the opportunity to help clients define and realize their journey, and co-founding Paces Ferry Wealth Advisors, an independent firm, allows the freedom to define the client experience along the way.

    Previously, Zach was a partner in The Diamond Morris Group and a Financial Advisor with J.P. Morgan Securities, a wealth management division of J.P. Morgan. Before becoming a Financial Advisor, Zach started as an Associate with the firm in 2011, where he developed skills for building lasting relationships with clients. Later, Zach developed and oversaw a training and mentorship program for J.P. Morgan Associates.

    Zach supports a number of organizations including Alzheimer’s Association, Georgia Chapter, The Shepherd Center, Crohn’s & Colitis Foundation of America, and NewStory.

    Zach received a B.S. in finance, with a minor in economics, from Elon University in North Carolina. He was a member of The Kappa Alpha Order and has served on the board of the Elon Alumni Association’s Atlanta chapter. Zach speaks Spanish and is an Atlanta native. He and his wife live in West Midtown’s Underwood Hills neighborhood and his parents and two of his three sisters and their families live nearby. In his spare time, Zach golfs, plays tennis, rides his mountain bike and travels.

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    For More on Zach Morris, CFP

    Paces Ferry Wealth Advisors

    Zach Morris, CFP® You Tube channel

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    Podcast Conversations You May Like

    How to Live a Meaningful Life – Dave Evans

    Re-Visioning Retirement – Susan Reid, PhD

    Retire with Purpose – Cesar Aguirre

    ______________________________

    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.

    ______________________________

    Wise Quotes

    On The One More Year Trap

    “Sometimes it’s just one more year because they don’t know what the next step is…If somebody is working one more year and they have 100% probability of success — they’re not just leaving money on the table, they’re leaving life on the table.”

    On Risk

    “Risk is invisible… you can have a risk tolerance today, but once you hit that maximum threshold, it can very quickly become uncomfortable.”

    On Retirement Planning

    “You don’t want to go into retirement with unfulfilled expectations. You want to go into retirement knowing what to expect.”

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  • The Retirement Wisdom Podcast

    Can I Retire Yet? – Darrow Kirkpatrick

    2026-02-23 | 25 mins.
    Don’t drift into retirement. Design yours.

    Learn more about our next small group coaching program starting in April here.

    Sign up here. Very Early Registration Discount ends on March 1st.

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    What happens when you finally get everything you worked for…and realize something is missing?

    In this powerful and deeply honest conversation, Darrow Kirkpatrick shares what early retirement can really feel like — beyond the spreadsheets and freedom headlines. After leaving his software engineering career, he found himself confronting something he didn’t expect: the loss of identity and clout that work had quietly provided. He discovered that early retirement wasn’t just about having time—it was about creating meaning. Instead of retreating, Darrow leaned into challenges. From launching a successful retirement blog Can I Retire Yet? to spending nights alone above 12,000 feet, to confronting his lifelong struggles with fear and panic, Darrow’s journey, chronicled in his new book Two Sticks, One Path, reveals the surprising truth about what can make retirement fulfilling.

    If you’re within a few years of retirement — or already there — this conversation will make you think differently about what comes next –  and why the challenges we choose to take on may matter more than the comfort we think we want.

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    Bio

    Darrow Kirkpatrick is the author of the new book Two Sticks, One Path: A Journey Beyond Fear on the Colorado Trail. Darrow is an early-retired civil and software engineer with five decades of hiking, biking, and technical rock-climbing experience, including first ascents in the Shawangunks of New York and the sandstone belt of Tennessee. He climbed three big walls in Yosemite Valley, California: The Shield and The Nose on El Capitan, and The Regular Northwest Face of Half Dome. In 2011 he founded “Can I Retire Yet?” — winner of the 2019 Plutus award for Best Retirement Blog. His personal finance books include “Retiring Sooner” and “Can I Retire Yet?”

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    For More on Darrow Kirkpatrick

    Two Sticks, One Path: A Journey Beyond Fear on the Colorado Trail

    Can I Retire Yet?

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    Podcast Conversations You May Like

    How to Prepare Mentally for Life After Work – Joseph Maugeri

    The Inspired Retirement – Nathalie Martin

    Lessons Learned in Early Retirement – Chris Mamula

    _____________________________

    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 the Value of Challenge in Retirement

    “I find 100% of the meaning that I found in early retirement has come from the challenges I’ve tackled.”

    On Meaningful Pursuits

    “The things I did pay attention to starting Can I Retire Yet, a successful personal finance blog, a bucket list item hiking the Colorado Trail, even though I had to do most of it on crutches, those things are incredibly meaningful to me, writing a memoir about it. I think I would have really regretted if I had stayed at my corporate desk through all those years instead of reaching for those bucket list items.”

    On Adaptation

    “I did have a series of chronic injuries in my lower body, which got worse. I had a bad hamstring injury, was in bed for a few months, one summer. And as part of the recovery from that, a doctor friend suggested I start using forearm crutches… I wound up realizing I needed to just keep using the crutches on the trail, because they would keep me safe. They reduce the impact on my body, they prevent falls. And if I had any hope of doing a trail as difficult as the Colorado Trail, I needed all the help I could get.”
  • The Retirement Wisdom Podcast

    Retire with Purpose – Cesar Aguirre

    2026-02-16 | 30 mins.
    Will you retire with purpose?

    Don’t leave it to chance.

    Design Your New Life after you leave full-time work.

    Learn more about our next small group coaching program starting in April here – and sign up here.

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    What if the word retirement is setting us up for the wrong life?

    After years in senior leadership roles, Cesar Aguirre discovered something most of us miss about retirement: the word itself matters more than we think. In English, we “retire” – we withdraw. In Portuguese, you become “aposentado” – left aside or left behind. But in Spanish-speaking cultures, retirement is called “jubilación” – which comes from the word for joy.

    That distinction changed everything for Cesar. Because when he stepped away from his career, it wasn’t the loss of work that shocked him – it was the jarring shock of losing an identity. He realized retirement isn’t just a life transition, it’s an identity transition, offering an opportunity to redefine who you want to become, and retire with purpose.

    Cesar joins us to share the framework he developed through his own transition – a ten-chapter roadmap for moving from “what I’m leaving” to “what I’m moving toward.” He’ll reveal why planning goes far beyond your finances, how to measure success when you’re no longer producing output, and the key warning signs that show up early when retirement first starts going wrong.

    This is a conversation about why approaching retirement with more intention might just create the most fulfilling chapters of your life. How will you retire with purpose?

    Cesar Aguirre joins us from Florida.

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    Bio

    César Aguirre is a seasoned HR executive with over 40 years of experience in global talent development. Now in active retirement, he embodies reinvention with passion as mentor, consultant, and author. In his book, Retirement with Purpose: The 10 Rs of Retirement, he shares his vibrant energy and insights to help readers rediscover purpose and embrace joyful living in their post-career lives. He currently resides in a lively 55+ community in Central Florida with his wife, inspiring others to design their authentic journeys for the second act of their lives.

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    For More on Cesar Aguirre

    Retirement with Purpose: The 10 Rs of Retirement

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    Podcast Conversations You May Like

    How to Prepare Mentally for Life After Work – Joseph Maugeri

    Re-Visioning Retirement – Susan Reid, PhD

    How to Retire – Christine Benz

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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.

    _________________________

    Wise Quotes

    On The Power of Language

    “Retirement becomes a celebration, not a retreat. I think the languages shape mindset. And mindsets shape behavior. So when retirement is framed as a joy, planning shifts from survival to flourishing become more natural.”

    On Measuring Success in Retirement

    “A good day is no longer about output, it’s no longer about how much you produce. It’s about action that is intended, an action that aligns with a master plan.”

    On What He’d Do Differently

    “I wish I had thought about it and prepared for my post-work identity a little sooner and more deliberately. In my job in HR, I helped many others plan careers, but I underestimated how much my own self-worth was tied to that job in that title. I think I did it humbly. I can say that I did a solid job planning financially, but probably not as good in preparing emotionally for the change. For a brief period of time, a few months, I underestimated that the identity shift that was occurring and the loss of a daily structure that I was so accustomed to.”

    On What He’s Gained in Retirement

    “Presence, the ability to not just having the time, but having the mindset of real presence, presence with my wife, which I neglected for a few years while I was traveling or working, presence with my kids, now with my grandkids, the rest of my friends, and new friends. I also gained a space and time for mastery, my hobbies. I enjoy cooking, well, time to do more and do a little better, exercising, riding the bike three or four times a week, playing pickleball. Retiring has given me time to go more in depth on my preferences instead of just speed, because in my working years, I was always rushing. Even when I was at home, I needed to accomplish, I needed to do things. I needed not to be idle. And retirement has now given me presence and bandwidth.”

    On Warning Signs

    “I think there are three main things that one needs to start paying attention to. Isolation. If you don’t have that network, social network, family network, and you become isolated. A loss of structure. Doing nothing without a structure or living in the past tense. When people stop connecting with others, when they drift through the days without an intentional plan, or when they only talk about what they used to be, that should be a warning, – a huge yellow flag for oneself and for loved ones that are looking after them.”

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About The Retirement Wisdom Podcast

Retire Smarter
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