PodcastsEducationThe Retirement Wisdom Podcast

The Retirement Wisdom Podcast

Retirement Wisdom
The Retirement Wisdom Podcast
Latest episode

160 episodes

  • The Retirement Wisdom Podcast

    Two Grannies on the Road – Beth Sobiloff & Marcia Rothwell

    18/05/2026 | 29 mins.
    What’s in your backyard that you haven’t explored yet? And what if you decided to treat your own state like a foreign country? Beth Sobiloff and Marcia Rothwell, the co-hosts of Two Grannies on the Road, have set out to visit all 351 cities and towns in Massachusetts. They’re 121 towns in. Along the way, they’ve met second-act bakers, retired leaders turned magicians, mayors, alpaca farmers, and a man with the world’s largest collection of Back to the Future memorabilia.

    In this conversation, Beth and Marcia talk about why their world hasn’t shrunk in retirement, why trying and not liking something is still a win, how to spot the second act that’s already running quietly in the background of your own life, and what a real retirement curriculum might look like.

    If you’ve ever caught yourself drifting toward a smaller version of your life, this episode is a friendly nudge in the other direction.

    In this episode you’ll learn:

    How to discern a second act that’s right for you.

    How Beth turned an empty-nest into a 15-year creative project.

    Why abandoned hobbies offer clues for new pursuits.

    A template for novelty, social connection, and learning that costs almost nothing.

    Why presenting what you learn matters as much as learning it.

    And here’s are all 351 towns and cities in Massachusetts in minutes

                                                                     (by two Mass natives and one NY interloper)

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    For More on Beth Sobiloff  & Marcia Rothman

    Two Grannies on the Road – You Tube

    Website

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    Wise Quotes

    On Experimenting

    “If you try something and you don’t like it, it’s not a failure. It’s okay. You eliminated one of the things you don’t like as much.”

    On the Curricuulm  for Retirement

    “Go out, experience something, then come back and present it. That’s the curriculum.”

    On Inspiring Others

     “If you have a relative or a friend who is staying at home and not getting out, make an effort to help them do that.”

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    Retirement Podcast Conversations You May Also Love

    Make Your Next Years Your Best Years – Harry Agress, MD

    Grandmapreneur – Connie Inukai

    Grace in Motion – Susan Hartzler

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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 2 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.
  • The Retirement Wisdom Podcast

    Letting Go to Become Who You Truly Are – Deborah Santana

    11/05/2026 | 31 mins.
    There’s a challenge that comes with being known for what you do. When you move on you now have to figure out who you truly are. Deborah Santana spent more than three decades inside one of the most recognizable partnerships in American music as COO of the New Santana Band, co-architect of the Milagro Foundation, and the steady, contemplative presence behind a global touring life with her ex-husband, the legendary musician Carlos Santana.

    At an age when most people are quietly winding down, she did the opposite: she walked away from a 34-year marriage, dismantled the identity she had built around someone else’s career, and started over. She earned a master’s degree in her 60s, founded a new nonprofit (Do A Little), wrote a second memoir (Loving the Fire: Choosing Me, Finding Freedom), and became a trustee of major cultural institutions.

    But this is not a celebrity interview. It’s an exploration of transitions and later-life reinvention. You’ll hear about her experience and the lessons she learned that may help you. She shares the foundational daily contemplative practice she built, the calendar block for herself disguised as “a meeting” she used to jump start her writing, and the people audit she did to illuminate who is toxic and who is the light in her life. Deborah describes how liberating it can be to be a beginner again, if you’re willing.

    I often say “You don’t stop growing just because you retire.” But, it’s not just a saying and Deborah’s story is an case study. If you’re ready to let go of your past and discover who you truly are now, this conversation is for you.

     

    “When you have everything stripped away that you were known as, it is a wonderful opportunity to create exactly who you are.”

    — Deborah Santana

     

    You’ll walk away with:

    A vocabulary for the identity work that retirement requires. And not just for the “what’s next” part, but also the words for the “who am I now” part.

    A useful framework (the Four C’s) for organizing life after a major transition.

    A replicable practice for protecting time for the work of “becoming” even when the people around you don’t quite yet understand what you’re doing.

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    Bio

    Deborah Santana is the author of Loving the Fire: Choosing Me, Finding Freedom, Space Between the Stars: My Journey to An Open Heart and the editor of the acclaimed anthology All the Women in My Family Sing. Her work has been featured by Vogue, Oprah, and NPR, among other national and literary outlets. She is the founder of the Do A Little Foundation, which supports women and girls in the areas of health, education, and happiness. Her work explores identity, social justice, spirituality, and the power of collective voice. She is mother to three artists: Salvador Santana, Stella Santana and Angelica Santana. She holds a Master of Arts in Philosophy and Religion with a Concentration in Women’s Spirituality. She is a leadership donor of the Smithsonian National Museum of African American History and Culture and a Lead Investor to the Courage Museum in San Francisco.

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    For More on Deborah Santana

    Loving the Fire: Choosing Me, Finding Freedom

    Website

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    Do You Know What You’ll Be Retiring To?

    It’s graduation season. Will you be graduatiing from full-time work soon?

    Join our 10-person Design Your New Life in Retirement Group starting in September.

    The Very Early Registration discount ends soon.

    Learn more and sign up today.

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    Retirement Podcast Conversations You May Also Love

    Mattering…in Retirement – Jennifer Breheny Wallace

    Navigating the In-Between – Monique Rhodes

    What Matters Most – Diane Button

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    Wise Quotes

    On Loving the Fire

    “When there is fire, when there is struggle, if I continue to walk through and find courage and bravery, then I’m going to get to the other side and realize how much I’ve learned, how much I’ve grown.”

    On Expectations

    “I expect a miracle. I expect to see someone, meet them with a smile.”

    On Finding Your Self

    “There is a special reason why you’re here. So please find your authentic self, find your voice, know who you are, and go out and change the world.”

    ___________________________

    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 2 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.
  • The Retirement Wisdom Podcast

    How to Flourish…in Retirement – Daniel Coyle

    04/05/2026 | 31 mins.
    Most of us were trained to win at the game of life, deliver the results and get the promotion. Then one day, we arrive at retirement and discover that the game we were trained for isn’t the one that actually produces a flourishing life.

    New York Times best-selling author Daniel Coyle, joins us to discuss his new book Flourish: The Art of Building Meaning, Joy, and Fulfillment. He unpacks what five years of studying thriving communities (a Michigan deli, a major league baseball team, and a Vermont town that keeps producing Olympians) revealed about how good lives are actually built.

    We discuss:

    Why flourishing is a team sport in an age of individualism

    The difference between task attention and relational attention, and why the switch matters

    Why visioning may be the most useful tool for people approaching retirement

    Why we should probe for retirement rather than plan for it

    Yellow doors, the rule of surprise, and the two questions Dan uses as a personal compass

    If you’re approaching a transition, or you’re in the bewildering middle of one, this is a conversation worth your time and reflection.

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    Bio

    Daniel Coyle is the New York Times best-selling author of nine books, including Flourish: The Art of Building Meaning, Joy, and Fulfillment, The Culture Code (which was named Best Business Book of the Year by Bloomberg & Business Insider), and the Talent Code. He is a contributing editor for Outside magazine, and has seved an advisor to many high-performing organizations including the Navy SEALS, Microsoft, Google and he also works as a special advisor to the Cleveland Guardians.

    Dan lives in Cleveland, Ohio during the school year and in Homer, Alaska, during the summer with his wife Jen, and their four daughters.

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    For More on Daniel Coyle

    Flourish: The Art of Building Meaning, Joy, and Fulfillment

    Website

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    Wise Quotes

    On Games versus Gardens

    “Life isn’t a game to win. It’s a garden to grow.”

    On Flourshing & Community

    “All flourishing is mutual. We only become our best selves through and with other people…Who do I feel most alive with? What am I helping to grow?”

    On the Value of No

    “If you can’t say no, your yes is worthless.”

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    Retirement Podcast Conversations You’ll Also Love

    The Good Life – Marc Schulz, PhD

    Making & Keeping Friends…in Retirement – Janice McCabe

    Will You Flourish or Languish? – Corey Keyes

    ____________________________

    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 2 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.
  • The Retirement Wisdom Podcast

    The Caregiving Trap…in Retirement – Pamela D. Wilson

    27/04/2026 | 22 mins.
    Registration for the September Designing Your New Life in Retirement is now open

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    Caregiving is one of the most common, and least discussed, forces that can completely reshape retirement.

    If you’re in your 50s or 60s, there’s a good chance you’ll either be a caregiver, or already are one. And yet, most people haven’t had the conversations, made the plans, or even considered what happens when a parent needs significant care.

    What starts as helping out… can quickly turn into something much bigger. And for many, it quietly begins to impact their time, their finances, their relationships—and ultimately, their own retirement plans.

    Today’s guest, Pamela D. Wilson, is a caregiving expert who has worked with families across the country navigating these exact challenges.

    In this conversation, we explore:

    Why caregiving situations become so complicated

    The early warning signs of burnout

    How family dynamics—especially among siblings—can make things harder

    And most importantly, how to approach caregiving in a way that protects both your parents—and your own future

    If you’ve ever wondered how to navigate this phase of life more thoughtfully, this is an essential conversation.

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    Wise Quotes

    On Family Relationships

    “Family relationships with aging parents and siblings are complicated… caregivers are thinking about what they’re giving up, while parents are dealing with their own losses and mortality…An elderly parent’s care needs can totally derail a child’s retirement… and most people never think about that until it happens.”

    On Warning Signs

    “When you get to the point where you don’t have time to take care of yourself—that is a warning sign that something is off.”

    On Planning for Caregiving

    “If you want to make decisions about how you live your life when you are older… you have to start planning today.”

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    For More on Pamela D. Wilson

    Website

    The Caregiving Trap: Solutions for Life’s Unexpected Changes

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    Bio

    PAMELA D. WILSON is a caregiving expert, advocate, and speaker offering support to family caregivers and professional caregivers through her business of the same name. Since 1999, Pamela has been a business owner providing direct service to families, individuals, caregivers, health and care providers, attorneys, and financial planners in the areas of care management, care navigation, caregiving services, caregiver support, elder care, legal and financial appointments and estate administration.

    Throughout her caregiving career, Pamela has provided education and training, advocacy, and support for family and professional caregivers. Today caregiving education, training, advocacy, speaking, and caregiver support are the main focus of her business. As the result of the aging population and increase in need for family caregivers—nearly 4 in 10 Americans are caring for a loved one—it is critical that family caregivers are knowledgeable about options, plan for care, and advocate for care needs. The increase in diagnoses of chronic disease, dementia, and Alzheimer’s disease strains the ability of family members—many who became caregivers as the result of an unexpected crises— to provide daily support, navigate the care system, and to plan for future needs.

    Professionals in healthcare, care agencies, care communities, and in the legal, and financial professions have a similar desire to be knowledgeable and to serve as a resource for family caregivers. Due to the specialization required in these industries and the day to day job demands, it is difficult for professionals to advise beyond the specialties in which they operate. Pamela’s expertise in the industry since 1999 provides the opportunity for professionals working in the industry to expand knowledge beyond their day to day specialties through training and education programs offered by Pamela.

    Information, education, and support is offered through The Caring Generation Library®, through Pamela’s book, The Caregiving Trap: Solutions for Life’s Unexpected Changes, articles, podcasts, webinars, online support groups, speaking and training. She produced and hosted a radio program on 630 KHOW-AM in Denver called The Caring Generation®. Pamela continues to develop programming and education on topics to support family and professional caregivers. Pamela is a member of professional associations focusing on estate planning and elder care, financial and estate planning, caregiving, aging, and healthcare.

    Pamela’s work has been applauded within the caregiving community because she has walked in the same shoes, and experienced the same frustrations as the professional caregivers and family members she serves. When she was 35, Pamela lost her mother to cancer and her father died a few years later. Soon after her older brother passed away, and by the time she was 40—Pamela had lost fifty percent of her immediate family. Rather than view these challenging circumstances as a tragedy, Ms. Wilson viewed them as an inspiring catalyst to answer the call in her heart to serve and help other caregivers.

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    Retirement Podcast Conversations You May Love

    My Mother’s Money – Beth Pinsker

    Planning for Family Caregiving – Danielle Miura, CFP

    On My Way Back to You – Sarah Cart

    ___________________________

    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 2 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.
  • The Retirement Wisdom Podcast

    The Grandparenting Blueprint – Richard Eyre (Part Two)

    23/04/2026 | 27 mins.
    Part Two is a solo conversation with Richard Eyre about the most personal project of his grandparenting work: the body of distilled life wisdom he has spent years developing for his 34 grandchildren — now published in the second half of The Grandparenting Blueprint. This conversation moves from the framework to the practice of how to translate a lifetime of learning into something children can actually carry with them. (Part One is here).

    This second part of the conversation opens with Richard’s vulnerability, sitting on a beach, feeling like a “spare tire” next to Linda’s natural grandmothering, and asking what role he wanted to play. What emerged was a question every thoughtful grandparent eventually confronts: What do I actually want to pass on? Richard’s answer became a multi-year project of identifying, refining, and teaching age-appropriate life lessons,  first as “principles,” then as “tips,” and finally, when the branding breakthrough happened, as Secrets.

    Richard shares the Harvard Business School case study method he adapted for nine-year-olds, the silver-dollar memorization incentive (he calls it bribery; I’ll call it incentive compensation…), how his grandchildren became unedited co-authors earning royalties, and the moment he realized the one word he most wanted to embody as a grandfather was not teacher or advisor, but champion.

    For listeners who are approaching or are already in the grandparent years, particularly grandfathers, who Richard observes are often the ones quietly wrestling with questions of legacy, this conversation offers both a philosophical approach and a practical starting point.

    The closing challenge to write down 10 lessons from your own life is the kind of exercise that could reshape how you  show up as grandparent for the next generation.

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    For More on Richard Eyre

    The Grandparenting Blueprint:How to Teach Your Grandchildren Life’s Most Important Lessons (Amazon)

    Also available from the publisher at the author’s price (40% off)

    https://familius.com/book/the-grandparenting-blueprint/

    Use the coupon code EYREFRIEND at checkout

    Website

    Part One podcast conversation

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    Wise Quotes

    On Being a Champion

    “I think what the grandparent wants to do is champion them. I’m your biggest supporter. I’m your biggest fan. I want to know what you like to do. I want to understand what you’re good at and what you want to be good at. Every kid needs a champion — and that’s probably not going to be their parents. So maybe that should be their grandparent.”

    On the Case Study Method for Kids

    “Case studies are really just a story. Only you, and the grandchild in this case, are the main person in this story. And I’m not going to finish this story. You’re going to finish the story. So it’s just a great way to teach.”

    On Rebranding Principles as Secrets

    “They came across like lectures and the kids were like enduring them rather than embracing them. And so I retooled them. I rebranded them as secrets. And suddenly I had their attention and they really started to matter.”

    _______________________

    Retirement Podcast Conversations You’ll Love

    Good Grandpa – Ted Page

    The Long Distance Grandparent – Kerry Byrne PhD

    All Grown Up – Celia Dodd

    _______________________

    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 2 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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About The Retirement Wisdom Podcast
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