The Retirement Wisdom Podcast

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...

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 h...

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...

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 emotiona...

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 introduc...

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 t...

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 Carl...

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 c...

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 happe...

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 ...

Part Two is here

What does it mean to grandparent on purpose? For Richard and Linda Eyre, the answer has been decades in the making. The bestselling authors of Teaching Your Children Values have evolved with their family, from nine children to 34 grandchildren, and along the way have developed a philosophy of proactive grandparenting that mirrors what good leadership looks like at any stage of life. In this 1st of 2 conversations a...

The wellness industry has a problem, and Ezekiel Emanuel is one of the few people willing to call it out. In his new book, Eat Your Ice Cream: A Contrarian’s Guide to Living Longer, Healthier, and Happier, the bioethicist, oncologist, and former White House health advisor challenges both the influencers selling unproven supplements and the culture of wellness-as-self-punishment.

In this episode, Emanuel makes a compelling res...

What if cognitive decline in your 60s, 70s, and 80s is not inevitable — but largely a function of choices you’re making right now? What can you do to stay sharp in retirement?

Dr. Majid Fotuhi is a neurologist, who teaches at Johns Hopkins University, and the author of The Invincible Brain: The Clinically Proven Plan to Age-Proof Your Brain and Stay Sharp for Life. He has spent decades studying the most malleable struct...

Retirement triggers one of the most profound re-evaluations many people will ever face. A career ends. Structure disappears. Identity shifts. And suddenly a question that could be put off — What do I really want out of life? — becomes more urgent and unavoidable. Valerie Tiberius has spent her career building a useful framework for exactly that question. Her insights offer you something much more valuable than advice on...

Friendship is one of the most powerful forces shaping our lives—and our health. Friendships become harder to maintain as life evolves, especially during major transitions like retirement. Losing work friends is normal, yet few realize how new connections can be cultivated. Our guest today highlights why identity shifts can, perhaps counterintuitively, create oppotunities to build new friendships.

My guest today is Janice McCa...

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Get started in April on your most important project. Learn more here

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Retirement planning focuses heavily on finances — investments, Social Security, and risks.

But there’s another question tha...

Discern what you’ll retire to.

Join our group program starting in April.

Learn more here

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What if the secret to happiness isn’t success or achievement — but simply feeling loved?

What’s next?

Don’t drift. Design.

Our next small group coaching program starts in April.

Learn more here.

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Most retirement planning conversations start and end with money. Rod Yancy, founder of Oath Planning, challenges that assumption head-on — arguing that mindset, emotional health, and identity matter more than any portfolio balance when it comes to actually thriving in retirement. ...

What’s next?

Don’t drift. Design.

Our next small group coaching program starts in April.

Learn more here.

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Who are you when you’re no longer your title? For many high-performing professionals, that question can feel destabilizing — even frightening.

Michael Kay is a CFP, a financial life planner, the author of the new book