The Retirement Wisdom Podcast

Valerie Tiberius, a philosophy professor and author who studies wellbeing and reflective living, guides a values-first rethinking of retirement. She explains values versus goals and how priorities shift with age. She introduces the “chuck it” list for letting go, explores hidden emotional goals, and warns about mistaking AI for true friendship.

Janice McCabe, a Dartmouth sociologist who studies how friendships form and fade. She talks about why proximity and similarity drive connections. She explains how identity shifts in retirement open new social opportunities. Practical ideas include recurring activities and intentional habits to build and maintain meaningful ties.

Jennifer Breheny Wallace, award-winning journalist and author who studies how people find meaning, discusses why the need to matter persists after work ends. She describes building a “mattering portfolio,” daily practices to restore purpose, the SED framework (Significance, Appreciation, Investment, Dependence), and practical places and actions that recreate visible, valued roles in retirement.

Sonja Lyubomirsky, a psychology professor and bestselling happiness researcher, explores why feeling loved fuels well-being. She discusses connection, curiosity, and high-quality listening. Learn about going first to spark reciprocity, the vulnerability paradox in life transitions, and simple conversational moves like “Tell me more.”

Rod Yancy, entrepreneur and attorney who founded Oath Planning to blend mindset and money. He argues emotional health, identity, and purposeful time use matter more than portfolio size. They cover healthcare worries, physical-health regrets, arts and longevity, avoiding drift, and how passions and social rituals shape thriving retirements.

Michael Kay, coach, teacher, author and retired CFP who helps people craft life after work. He explores identity beyond titles, why retirement narrows your perspective, and how to reopen curiosity. He talks about grieving what’s lost, relearning to be a beginner, and choosing joy over habit. Practical reframes and small experiments are highlighted to help design a meaningful next chapter.

Zach Morris, CFP, co-founder of Paces Ferry Wealth Advisors who helps clients design retirement and life plans. He talks about updating your retirement timeline and income picture. He explains risk tolerance versus risk capacity and sequence of returns risk. He warns about the “one more year” trap, planning for family surprises, and building an identity beyond work.

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. _______________________ 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. _________________________ 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?” ___________________________ For More on Darrow Kirkpatrick Two Sticks, One Path: A Journey Beyond Fear on the Colorado Trail Can I Retire Yet? ___________________________ 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. ___________________________ 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.”

César Aguirre, a seasoned HR executive and author turned active retiree who mentors and consults. He reframes retirement as an identity shift, not withdrawal. He describes emotional surprises, the power of language to shape mindset, and a ten-step roadmap for designing a joyful, purposeful post-career life. Practical signs to watch for and ways to stay curious and engaged are highlighted.

Sign up for our next Designing Your Life small group coaching program starting in April here __________________________ What happens when you’ve done everything “right” — built a successful career, made a difference, checked the boxes — and yet something still is missing? Today I’m joined by Dave Evans, co-author of How to Live a Meaningful Life: Using Design Thinking to Unlock Purpose, Joy, and Flow Every Day and the #1 New York Times Bestseller Designing Your Life, and a longtime Stanford educator, to explore a question many people quietly wrestle with in the second half of life: Why doesn’t impact bring lasting meaning — and what actually does? Dave shares insights from his newest work with Bill Burnett on meaning, presence, and what he calls the shift from role to soul. We talk about why chasing fulfillment often backfires, why the most meaningful moments are often small and fleeting, and how many of us live almost entirely in what he calls the “transactional world” — often missing the richness of the present moment that’s available right now. This conversation is especially relevant if you’re nearing retirement, newly retired, or simply sensing that achievement alone isn’t enough anymore. Dave offers practical reframes, deeply human stories, and a powerful idea he calls the scandal of particularity — a concept that may completely change how you think about what a well-lived life really looks like. Dave Evans joins us from California to discuss How to Live a Meaningful Life. ___________________________ Bio Dave Evans is the co-author of How to Live a Meaningful Life: Using Design Thinking to Unlock Purpose, Joy, and Flow Every Day. Dave has worked in alternative energy, telecommunications, and high tech. As an early member of the advanced systems group that built the technology that became the Macintosh, he led the first computer mouse team and laser-printing projects, before leaving to co-found the software giant Electronic Arts. After more than thirty years of executive leadership and management consulting in the high tech world, Evans realized that what he really wanted and needed to do was help people rediscover purpose in their jobs and lives. He joined Stanford’s Design Program, teaching the incredibly popular Designing Your Life course. In their book Designing Your Life, Dave Evans and co-author Bill Burnett, brought these principles to a larger audience, proving it’s never too late to design a life you love through innovation, creative problem-solving, and a growth mindset. Evans teaches audiences of all ages that the same principles used to create amazing technology and products can also be used to design and build a life filled with purpose and joy that is constantly creative and productive. Dave Evans earned a Bachelors of Science and Masters of Science in Mechanical Engineering from Stanford and a graduate diploma in Contemplative Spirituality from San Francisco Theological Seminary. He lives in Santa Cruz. _________________________ For More on Dave Evans How to Live a Meaningful Life: Using Design Thinking to Unlock Purpose, Joy, and Flow Every Day  Design Your Life and Get Unstuck – Dave Evans (2020 Podcast) _________________________ Podcast Conversatons You May Like The Good Life – Marc Schulz, PhD Resurface – Cassidy Krug The Purpose Code – Dr. Jordan Grumet __________________________ 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 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 1.9 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 Becoming “The most essential definition of a human person is you’re a becoming. You’re constantly evolving into hopefully your more and more authentic self – never your complete self, by the way… there’s no way you’re ever going to get done.” On Shifting from Role to Soul “I think, particularly in that second half transition, you’re really looking at what we call the shift from role to soul. And by role, I am primarily identifying who I am as a person, my sense of what makes me who I am, is what I do in the roles and I have in the world, mostly in institutions called, you know, companies or employment or families. And I get this feedback loop from being the Dad, from being the General Manager, from being the mailman, or from whatever it is that says I’m doing the right thing, I’m getting paid for it, and the world’s a better place. And that’s the achievement feedback loop, which for most people that’s what we mostly hear from people is the primary thing. And as life moves along, even if you’re still achieving, I still have four part time jobs. But my relationship with that achieving role is very different than it used to be. And you start moving more and more where your life is really simply about expressing as authentically as you can in the world, who it is that you actually are.” On the Scandal of Particularity “The scandal of particularity is the recognition that all wonderful things only come in these small bite-sized pieces that are temporary, incomplete, partial, but reflections of the true thing. So if you radically accept you’re never going to get all of it, then you go, Oh, so what I really want to do is when the opportunity for some beauty or some truth shows up at all is dive all in, fully celebrate and enjoy it.”