The Retirement Wisdom Podcast

Don’t miss out on a great life in retirement because you fail to prepare for it.

Join our next Design Your New Life in Retirement small group program in September.

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Walter Green has spent nearly three decades doing what most of us postpone: telling the people who shaped him exactly why they mattered, while they can still hear it. The founder of the Say It Now movement joins us to share his journey, his new book The Gratitude Express, a deceptively simple question that replaces “What should I do?” in retirement, and why he decided to reimagine rather than retire.

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Bio

Walter Green’s father died when he was a teenager and it left an indelible impression on him that life is short, precious, and unpredictable. Walter decided it was never too early and not too late to express his profound appreciation for those who had impacted his life. That is when he began his journey of seeking out those people who made a significant impact. It was the moment to share his gratitude with them.

Walter Green was Chairman of the Board and CEO of Harrison Conference Services for 25 years, during which time it grew into the leading conference center management company in the U.S. He has lectured at the Wharton Graduate School of Business and Hofstra and Long Island universities, as well as being featured as an expert on the topic of effective meetings in numerous national publications. Associated for years with the Young Presidents’ Organization and the World Presidents’ Organization, he’s a member of the Chief Executives Organization and the L3 Organization (Leadership, Legacy, Life). Since selling his company, he has mentored young adults and is actively involved in several non-profit organizations. He lives with his wife, Lola, in San Diego, California.

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For More on Walter Green

The Say It Now Movement

The Gratitude Express

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Retirement Podcast Conversations You’ll Also Love

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

The Best Day of My Life So Far – Benita Cooper

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Wise Quotes

On Retirement Planning

“I never asked, ‘What should I do?’ I asked: if I were ideally successful at this stage of my life, how would I know it? …Look toward the things you were doing while you were doing the other stuff. Look for the patterns… I don’t even like the word ‘retirement.’ Reimagining is where I am.” 

On Why You’ll Want to Say It Now

“Put a flashlight on a relationship, illuminate it, and really look at why it was so important…You’ll think it’s for the other person — but in reality it’s just as much for yourself…We’re the only ones who can give this gift. You can’t delegate it to somebody else.” 

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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.

There’a a whole half a year to go!

Start the second half strong with new habits.

Free 1 hour workshop July 1 | 12 noon ET

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You’re preparing for retirement. For many of us, there’s another transition nestled within that one. It comes with joy and little instruction – becoming a grandparent. Celia Dodd, a journalist of 30+ years and grandmother of six, has written the book many grandparents wish they had: one that celebrates the delight and makes room for the honest, complicated feelings nobody admits out loud: Grand Expectations: The Joys and Dilemmas of Being a Grandparent.

This conversation is about permission. Permission to feel torn between the grandchildren you adore and the next chapter you’ve spent years planning. Permission to be your own version of a grandparent rather than the one in your head. Permission to support without interfering, to say no without guilt, and to design these special years deliberately instead of drifting into them.

Celia Dodd joins us from London.

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Bio

Celia Dodd is a journalist and author who wrote regularly for The Times of London, the Independent and other national newspapers and magazines, focussing on relationships, family life, health and education. She also wrote profiles of interesting people, including Gordon Ramsay, Lou Reed and actress Juliet Stevenson. 

After thirty years as a journalist she turned to writing books about parenting and major transitions in life, such as the empty nest and retirement. They are subjects close to her heart as well as her own stage in life. 

Her new book is Grand Expectations: The Joys and Dilemmas of Being a Grandparent.  She’s also written All Grown Up: Nurturing relationships with adult children,  Not Fade Away: How to thrive in retirement, The Empty Nest: Your changing family, your new direction  and Conversations with Mothers and Daughters.

Celia has two adult sons and a daughter, and six grandchildren.

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For More on Celia Dodd

Grand Expectations: The Joys and Dilemmas of Being a Grandparent

Celia Dodd’s first visit with us: All Grown Up (on relationships with adult children, and thriving in retirement)

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Retirement Podcast Conversations You’ll Also Love

The Grandparenting Blueprint – Linda & Richard Eyre (Part One)

The Mindful Grandparent – Dr. Shirley Showalter’

Grandparents’ Day – Kerry Byrne & Ted Page

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Wise Quotes

On Grandparenting & Purpose

“Grandparenting has been life-enhancing in so many different ways. It’s brought me a new purpose.”

On Being a Grandparent & Being Yourself

“It’s about being your own version of a grandparent.”

On Relationships with Adult Children

“There’s a fine line is between being supportive and interfering…Don’t give advice unless they ask for it.”

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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 first half of 2026 is ending. But there’s another whole half of the year ahead. Remember your New Year’s resolutions? A fading memory, but there are aspirations in them that you can bring to life in the second half.

Join me for a free 60-minute FREE small group workshop on how to apply Stanford’s BJ Fogg’s 3-step habits process to three things you’d like to start in the second half of 2026.

July 1st | 12:00 Eastern | Zoom Sign up here

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Let’s face it. We spend years preparing for a career and almost no time preparing for the decades that follow. In this episode, investor advocate Pam Krueger, founder and CEO of Wealthramp and creator of PBS’s MoneyTrack, rejoins us to reframe what retirement readiness really means. The conversation moves from the money (why diversification is a verb; why the sequence of your returns matter; and why the saving habit that built your wealth has to be unlearned to spend it) to the life side of the equation (the “dimmer switch” alternative to the on/off switch of a traditional retirement,  and the conversation couples should not skip).

The big idea Pam shared today is optionality: instead of planning toward a single date or a magic number to hit, build a plan that’s resilient enough to flex as life changes, because it will. It’s a practical, candid look at designing the kind of next chapter you’ll love to get to live.

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Bio

Pam Krueger is an investor advocate, personal finance journalist, and author with over 25 years of industry experience. She’s the founder and CEO of Wealthramp, a fee-only financial advisor referral service built on a foundation of trust, transparency, and consumer protection. Since 2019, Wealthramp has connected nearly 30,000 people to right-fit advisors and coaches.

Pam is also the creator and co-host of the award-winning MoneyTrack series on PBS and the Friends Talk Money podcast. She’s a two-time Gracie Award winner and earned the NAPFA Special Achievement Award for championing fiduciary financial advice. Her work is widely respected for its transparency and focus on helping people achieve financial confidence.

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For More on Pam Krueger 

Wealthramp

Pam’s first visit with us is here

(She describes her approach to vetting financial advisors in the second half of the conversation)

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Other Retirement Podcast Conversations You’ll Love

What If Retirement Is the Wrong Goal? – John Coleman

Design a Phased Retirement – Anna Rappaport

The Second Curve of Life – Arthur C. Brooks

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Retiring Soon?

Do Your Due Dilligence:

Best Books for Retirement

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Wise Quotes

On a Balanced Aproach to Retirement Planning

“Financial plans are going to fail when life plans were never discussed.”

On a Gradual Shift to Retirement

“Retirement planning can be put on a dimmer switch. That’s why we have dimmer switches. When you let go of that on-off switch, you’re letting go of so much more than the grueling workday…If optionality is your goal, you’re going to be in a heck of a better position.”

On Shifting from Saving to Spending

“The very habit that helped you build wealth suddenly changes to a whole new strategy.”

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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.

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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The views and opinions expressed by guests on The Retirement Wisdom Podcast are solely those of the guests and do not reflect the opinion of the host or Retirement Wisdom, LLC. The Retirement Wisdom Podcast primarily covers the non-financial aspects of retirement. From time to time we may invite guests who discuss other aspects of retirement planning, solely for educational purposes. Listeners are advised to consult qualified financial and/or medical professionals on those matters.________________________

Retirement. You could wing it. Why not design it?

Our next group proram starts in September and is limited to 10 people.

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

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In our last conversation, Dan Pontefract gave us a demographic wake-up call. The future of work is aging, and longer lives will require new thinking about careers, retirement, and contribution.

Today, Scott Siff brings that to the practical level: how do we create better pathways for people who want to keep contributing, but not necessarily in the same way? And what are employers missing when they overlook experienced talent?

His story begins with his father’s frustrating search for a new job in his 70s, and builds into a larger conversation about age bias, unretirement, labor shortages, and the need to redesign work for longer lives.

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Bio

Scott Siff is the founder and CEO of Pivoters, a job-matching platform focused on helping people 55+ connect with employers seeking experienced talent. His story begins with his father’s frustrating search for a new job in his 70s, and builds into a larger conversation about age bias, unretirement, labor shortages, and the need to redesign work for longer lives.

Siff is also a founder and Managing Partner at Quadrant Strategies, a Washington, D.C.-based strategy research and communications firm. His background includes advising senior leaders, Fortune 50 companies, and high-profile political figures on public affairs, brand, reputation, crisis, competitive positioning, and strategic communications.

Earlier in his career, Siff served as CEO of BAV Consulting, Vice Chair of the global research firm PSB, and worked at the U.S. Department of Justice as a prosecutor and later as counsel in the Environment Division. He earned a B.A. from Harvard University, Phi Beta Kappa, and a J.D. from Harvard Law School, where he was an editor of the Harvard Law Review.

Scott Siff joins us from Washington, DC.

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For More on Scott Siff 

Pivoters

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Other Retirement Podcast Conversations You May Like

The Portfolio Life – Christina Wallace

The Unretirement Life – Richard Eisenberg

Working Identity – Herminia Ibarra

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Best Books on Retirement

Our reccomendations and summaries are here

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Mentioned in This Episode

The Future of Work is Grey – Dan Pontefract

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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.

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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Wise Quotes
On Rethinking Work“At 55, you may well have 30 years of work life left, but you probably have 25 really good years, which is the same length of career as from the ages 25 to 50.”On What Employers Are Missing “There’s a pool of 40 million unused workers ready to go, better workers, and they’re sitting there on the sidelines, begging to get in the game.”On Reframing Aging

“A 65-year-old today is like a 45-year-old 20 years ago. And I’m not saying that theoretically, that’s what the science is finding.”

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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.