The Retirement Wisdom Podcast

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.

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.