The Retirement Wisdom Podcast

Take charge of your future. Our next group proram starts in September and is limited to 10 people.

The Very Early Registration discount (45%) ends on June 21. Learn more here.

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Dan Pontefract spent two decades building leadership, culture, and engagement inside high-tech and telecom organizations, and never once thought seriously about age. Then, in his early fifties, he had a wake-up call. It sent him to look under a rock he’d never lifted, where he found “an absolute cavern of issues.” The result is his sixth book, The Future is Grey: The Untapped Value of Age in the Workforce.

Dan lays out the coming “bell to bulb” demographic inversion and the risks for organizations ignoring it. For individuals, he reframes the whole arc of a working life, from the language of generations (which he rejects as an ageist cognitive bias) to three universal career eras: Rivers, Rocks, and Rubies. That demographic inversion means experience will become more scarce and valuable. The through-line is don’t retire,  rewire instead. He shares stories of people who kept working or returned to work in a different way, which brings his concept of the “experience dividend” to life.

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Bio

Dan Pontefract is a renowned leadership and culture strategist, author, and keynote speaker with over two decades of experience in senior executive roles at companies such as SAP, TELUS, and Business Objects. Since then, he has worked with organizations globally, including Salesforce, Amgen, State of Tennessee, Nestlé, Canada Post, Autodesk, BMO, Government of Canada, Manulife, Nutrien, UBC, McGill University, Virgin Media O2, City of Toronto, among others. Dan has firsthand experience in turning leaders and corporate cultures into a competitive advantage.

In addition to The Future of Work Is Grey, Dan has written five other books: WORK-LIFE BLOOM, LEAD. CARE. WIN., OPEN TO THINK, THE PURPOSE EFFECT, and FLAT ARMY garnering multiple awards including the Thinkers50 Top New Management Book and the Axiom Business Book Awards Gold Medal. Dan has also written for Forbes, Harvard Business Review, Leader to Leader, The Globe and Mail, Inc., among other outlets. Dan is a renowned keynote speaker who has presented at four TED events and delivered over 600 keynotes. He is an adjunct professor at the University of Victoria and has received over 25 personal awards. Dan’s career is interwoven with corporate and academic experience, coupled with an MBA, B.Ed, and multiple distinctions. Notably, Dan is listed on the Thinkers50 Radar, HR Weekly’s 100 Most Influential People in HR, PeopleHum’s Top 200 Thought Leaders to Follow, and Inc. Magazine’s Top 100 Leadership Speakers.

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The Future is Grey: The Untapped Value of Age in the Workforce

Website

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Other Retirement Podcast Conversations You’ll Love

The Second Curve of Life – Arthur C. Brooks

Design a Phased Retirement – Anna Rappaport

Rewirement – Helen Dennis

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Wise Quotes

On Wisdom

“Wisdom is to the experience dividend what oxygen is to fire.”

On Retiring Retirement

“Instead of using the word retire, I very much encourage people to use the word rewire.”

On Demographic Shifts

“We’re shifting from a bell-shaped society to a bulb-shaped society, and it’s going to change the talent makeup of your organization very, very soon.”

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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.

Be intentional. Design Your New Life in Retirement. Our next groups start in September.

The very early registration discount ends June 21st. Learn more.

What if everything you’ve been told about retirement is quietly working against you? John Coleman has spent his career around money and purpose, which makes his message all the more striking: money is a tool, not the point. In his new book, Good Money: Six Steps to Building a Financial Life with Purpose, he rethinks personal finance around human flourishing, and one of his steps reframes retirement itself: save for freedom, not retirement.

We explore why the conventional retirement script, a withdrawl into pure leisure, carries real costs to meaning, community, and health; how continued, self-directed work changes both the math and the meaning of your plan; why your worth is never your net worth; and how to design your next chapter deliberately. It’s a conversation that bridges the financial and non-financial sides of retirement, looks at retirement and purpose, and gives you a fresh way to think about what comes next.

John Coleman joins us from Atlanta.

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Bio

John Coleman is the author of Good Money: Six Steps to Building a Financial Life with Purpose and The HBR Guide to Crafting Your Purpose. He is Co-CEO of Sovereign’s Capital. He has prior professional experience at McKinsey Company, Invesco, and Bridgewater Associates, among others.

He’s active in his community, with current or prior experience on the boards of Teneo, the Heritage Foundation, Berry College, the DeKalb County School System, the Georgia Student Finance Commission, the Georgia Charter Schools Association, and the Georgia Independent College Association. He’s been recognized as a Term Member at the Council on Foreign Relations, a Presidential Leadership Scholar, and as one of both Georgia Trend’s and the Atlanta Business Chronicle’s “40 Under 40.”

A frequent contributor to Harvard Business Review, John and his work has been featured in Forbes, the Washington Post, the New York Times, the Financial Times, and the LA Times among other publications. He’s previously published Passion & Purpose and How to Argue Like Jesus.

John is an MBA graduate with High Distinction from the Harvard Business School, where he was Class Day Speaker and a Dean’s Award Winner for leadership and service. And he’s an MPA graduate of the Harvard Kennedy School, where he was a George Fellow and a Zuckerman Fellow.

John lives in Atlanta with his wife Jackie, their four young children.

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For More on John Coleman

Good Money: Six Steps to Building a Financial Life with Purpose

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Retirement Podcast Conversations You’ll Also Love

How to Flourish…in Retirement – Daniel Coyle

Mattering…in Retirement – Jennifer Breheny Wallace

The Good Life – Marc Schulz, PhD

How to Live a Meaningful Life – Dave Evans

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Wise Quotes

On Retirement

“In general, I’m opposed to the idea of retirement…People are made for meaning, they’re made to deploy their talents in productive ways…The frame I encourage people to take is that they’re saving, not so that they have enough that they can withdraw from the world, but saving so that they have the buffer to engage the world in the way that they want to at the pace that they want to.”

On Money

“Breaking the hold that money has on us, making sure it’s a tool, not a totem, is one of the very first mindsets that people need to adopt…Money isn’t intrinsically good. Money is good only in so much as you use it for things that build flourishing in your lives and the lives of others.”

 On Identity

“Too often we fall into making our identity the things that are easiest to measure rather than things that are most important.”

On Purpose

“I believe purpose is a thing that’s built, not found. It’s crafted, it’s not found.”

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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.

 

A retirement is a terrible thing to waste.

Don’t just retire. Design your new phase of life – with intention.

Our next groups start in September.

The very early registration discount ends June 21st.

Learn more.

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Retirement rarely unfolds exactly as planned.

For Jerry Goodstein, retirement began with a clear sense of direction and a meaningful endeavor. But unexpected challenges, a deeply emotional experience helping his daughter move across the country, and an encounter with the world of ADHD coaching changed everything.

In this conversation, Jerry shares how his retirement story became less about executing a blueprint and more about learning how to “turn into the swerve”  by staying open to reinvention, purpose, lifelong learning, and becoming someone new later in life.

This is a thoughtful conversation about identity, letting go, service, and the surprising ways purpose can evolve, over time and in ways you may not expect, after retirement.

In This Conversation, You’ll Learn

Why God laughs at your retirement plans

How unexpected “swerves” can open new directions in life

The opportunities to repurpose your skills in retirement

Why letting go of identity is often difficult for high achievers

How lifelong learning can reignite energy, curiosity and engagement

What coaching taught Jerry about listening and presence

Why service became more important than living a life of leisure

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Bio

Jerry Goodstein is Professor Emeritus, Carson College of Business, Department of Management, Information Systems, and Entrepreneurship at Washington State University. Dr. Goodstein received his Ph.D. in Business Administration from the University of California, Berkeley, and his MBA and BA in Economics and Geography from the University of California, Los Angeles.

He conducted research and taught business ethics, leadership, and strategy at the undergraduate and graduate levels for over three decades at Washington State University and the University of Illinois. His research on restorative justice in organizations, corporate and stakeholder responsibility, and second chance hiring has been published in leading management and business ethics journals. He is co-editor, along with Dr. Mary Gentile, of Giving Voice to Values: An Innovation and Impact Agenda, published in 2021.

After retiring from Washington State University in May 2020, Dr. Goodstein continued work he had begun in 2019 to bring together businesses, criminal justice partners, and community-based organizations to develop employment-based opportunities for formerly incarcerated men and women. In January 2023 Dr. Goodstein made a major retirement/life shift to become a Certified ADHD Life Coach. He founded Where You Are ADHD after completing his ADHD life coaching program in December 2023. Since then, he has been coaching youth (teens and tweens) with ADHD. Dr. Goodstein partners with public and community-based organizations, especially those working with at-risk youth, to support both youth and their families in meeting the ADHD-related challenges they are facing in their lives.

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For More onn Jerry Goodstein

Where You Are ADHD

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Retirement Podcast Conversations You’ll Also Love

The Inspired Retirement – Nathalie Martin

The Best Day of My Life So Far – Benita Cooper

Changing the World One Small Act at a Time – Brad Aronson

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Wise Quotes

On Being Open to Reality

“There are just some unanticipated swerves that come up…Turn into the swerve…Don’t turn against it.”

On Becoming a Beginner Again

“It absolutely feels like a new beginning for me….“It’s never too late to learn. It’s never too late to evolve.”

On Purpose

“I don’t think of myself as retired anymore….I’ve repurposed my purpose.”

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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.

 

Most of us think of questions as something we ask other people. Dr. Marilee Adams has spent years showing the opposite: the most consequential questions we ask are the ones we ask ourselves. Adams, founder of the Inquiry Institute and author of the half-million-copy bestseller Change Your Questions, Change Your Life, (a new 5th edition has just been published) joins us to make us smarter about our internal questioning. She introduces us to two mindsets that live inside all of us  — Judger and Learner — and the Choice Map™ that helps you notice which one is driving the bus. The conversation takes her work directly into the world of retirement, where Judger questions (What do I regret?, What do I resent?) can quietly shape our moods, relationships, and the texture of later life. But Learner questions (What would be meaningful next?, What does my heart want me to do?, What can I contribute?) open up possibilities for a different future.

Along the way, Adams explains the physiology underpinning the two mindsets, and a single powerful question: Who do I choose to be in this moment? that she returns to again and again. She also introduces us to the five-to-seven-second “Stop, Breathe, Be” practice that can shift your nervous system anytime (from The 5 Resets: Rewire Your Brain and Body for Less Stress and More Resilience by Aditi Nerurkar, MD).

If you’re thinking about designing the non-financial side of your next chapter, or looking to enhance your life in retirement, this is an episode worth re-listening to with a notebook in hand.

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For More on Marilee Adams, PhD

Change Your Questions, Change Your Life, 5th Edition

Take the Survey & Download The Choice Map™

The Inquiry Institute

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Bio 

Dr. Marilee Adams is an award-winning author, executive coach, and leadership consultant whose work has shaped how leaders think, communicate, and make decisions for more than four decades.

She is Founder and CEO of the Inquiry Institute, a leadership development and organizational consulting firm dedicated to building inquiry-based cultures that accelerate results and deepen engagement. Its executive coaching, training, keynotes, and eLearning programs — all grounded in Question Thinking™ — are used by Fortune 500 companies, government agencies, healthcare systems, and universities worldwide.

Her book Change Your Questions, Change Your Life has sold more than half a million copies worldwide and been translated into 26 languages. Now in its 5th edition, it remains one of the most enduring frameworks for mindset shift, leadership development, and human performance — and its newest edition addresses one of the defining challenges of our moment: how to lead and think with wisdom, curiosity, and connection in an age of artificial intelligence.

At the heart of Dr. Adams’ work is a deceptively simple insight: the questions we ask — of ourselves and others — shape everything. They determine the quality of our thinking, our relationships, our decisions, and our cultures. In a world increasingly mediated by technology, the human capacity for inquiry is not just a leadership skill. It’s a competitive advantage — and an essential one.

Dr. Adams has coached senior leaders and advised organizations internationally and is a recognized pioneer in inquiry-based coaching and organizational transformation. She speaks and teaches worldwide, helping leaders use Question Thinking™ everywhere it matters most.

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Wise Quotes

On the Two Mindsets

“We’re always asking ourselves questions that affect our moods, that help with our decisions, and also make a difference in whether we have a positive quality mindset or the opposite. All of us human beings have two mindsets. We always will have them — which means they are normal…The more we accept our Judger, the more acceptance and forgiveness and empathy come online. That helps you open your heart to yourself and to others.”

On Questions 

“Typical Judger questions in later life are: How can I just fill up my time? What would keep me from being bored? What do I regret or resent about the past? Learner questions sound different: What would be meaningful and satisfying for me going forward? What does my heart want me to do next? What can I contribute? What would be fulfilling? People who are more in Learner mindset literally live longer and have better quality lives. People who are past-oriented, regretful, resentful, live not as long and not as fulfilling.

On Retirement

“When you think about retirement, what’s exciting is to be open to the future and not get stuck in the past. Now you’re talking about creating a future that is intentional, and fulfilling, and healing.”

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Retirement Podcast Conversations You’ll Also Love

The Second Fifty – Debra Whitman

Thinking Better to Live Better – Dr. Woo-kyoung Ahn

The Mindful Body – Ellen Langer

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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.

 

 

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.