This retirement podcast covers the changing nature of retirement today. Our guests offer useful insights on how to retire as well as the non-financial aspects of a successful retirement transition including retiring early, working longer and making a career shift in pre-retirement.
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This retirement podcast covers the changing nature of retirement today. Our guests offer useful insights on how to retire as well as the non-financial aspects of a successful retirement transition including retiring early, working longer and making a career shift in pre-retirement.
Spring Training (for the Rest of Your Life) – John Kaag
The Retirement Wisdom Podcast
25 minutes 8 seconds
4 months ago
Spring Training (for the Rest of Your Life) – John Kaag
In today's complex, fast-paced world, what can we learn from philosophers? John Kaag thinks we can learn a lot. He's created an audiobook Spring Training (for the Rest of Your Life), discussing his ideas highlighting Thoreau, Emerson and William James. He's also the co-founder of Rebind, an AI company transforming classic literature into interactive, guided experiences. Rebind pairs books with original interactive commentary from some of today's greatest thinkers who serve as expert guides, featuring conversations, personal anecdotes, historical context, and reflections. Rebind was named to Fast Company’s prestigious list of the World’s Most Innovative Companies of 2025 and was a TIME Magazine "Best Invention of 2024."
John Kaag joins us from Massachusetts.
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Bio
John Kaag is a distinguished philosopher and author, widely recognized for his deep knowledge of Henry David Thoreau’s classic Walden. He has authored several books, including American Philosophy: A Love Story and Hiking with Nietzsche, both of which were New York Times and NPR Best Books of the Year. In 2023, he published Henry at Work, a thorough examination of Thoreau’s philosophy as it relates to post-pandemic work habits. Kaag has contributed to The New York Times, The Wall Street Journal, and Harper’s Magazine, bringing timeless philosophical insights to a wider audience.
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For More on John Kaag
Spring Training (for the Rest of Your Life)
Rebind
Try Rebind - Discount offer
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Podcast Episodes You May Like
Living for Pleasure – Emily Austin, PhD
The Art of the Interesting – Lorraine Besser, PhD
An Artful Life – John P. Weiss
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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 also 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 twenty-six-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking. Today, in addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, which thanks to his guests and loyal listeners, ranks in the top 1 % globally in popularity by Listen Notes, with over 1.6 million downloads. Business Insider has 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 Philosophers - and AI
"I think it's interesting. I think that when it comes to the perennial questions of philosophy, like why am I here? What is the good life? Why is life worth living? These questions typically are answered in very personal settings, between friends, between family members, between, I teach at UMass Lowell,
The Retirement Wisdom Podcast
This retirement podcast covers the changing nature of retirement today. Our guests offer useful insights on how to retire as well as the non-financial aspects of a successful retirement transition including retiring early, working longer and making a career shift in pre-retirement.
