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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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

Rebind

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Podcast Episodes You May Like

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The Art of the Interesting – Lorraine Besser, PhD

An Artful Life – John P. Weiss

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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, so my classes are relatively small within a classroom setting. But I think what’s interesting is that when like lots of readers and lots of thinkers don’t have the chance to interact with others in a sort of active way. My mother was one of these individuals. She retired when she was 68, and she lived until she was 76. And during that time, she spent quite a bit of time online, reading online, but she really missed human companionship. And what’s interesting with this time of AI and artificial intelligence is that we have the ability to scale one-on-one tutoring interactions. Many people have talked about the use of Chat GPT and asking Chat GPT questions and getting responses. But what I find really interesting is that we have the chance to use AI to dynamically distribute original human comments and commentary into conversation.”

On William James, Action and Emotion

“William James…was the founder of empirical psychology at Harvard, the founder of American Pragmatism, which is one of the two major philosophies that was born in the United States in the 19th century. William James, in his empirical studies of psychology, discovered that there’s a real relationship between action and emotion. And we often times think that we’re happy and therefore we smile. But William James, and it’s it’s termed the James-Lange theory of emotions instead of saying that we smile because we’re happy. James said the other way around. He said, we are happy because we smile. So anybody who’s been down in the dumps and gone for a walk and felt better or anyone who’s even tried a little bit of yoga, sort of the beginning sun salutation, where you point your hands up to the ceiling and point your chin up to the ceiling. Looking up has this transformative power on our emotional landscape. And James was the first to discover this. It’s going back to my mother. She declined very precipitously when she could no longer walk and her emotional state sort of declined very rapidly as well.”

On Habits

“William James was pretty smart about habits. He said, following the ancient Greek Aristotle, that habits form ourselves. So if you think about who you are as a person, you are sort of defined by what you do in a habitual way, and your body actually takes the shape of the habits that we participate in. James, however, unlike Aristotle, was interested more in our ability to break habits, to unfix the beliefs that might have been given to us by our conventions, our society, our histories, and trying to overcome those. For James that was the task of life. If we think about cases where we reach our limits, or our habitual limits in life, and then overcome them and explore possibility, risk, uncertainty, what philosophers call indeterminacy, the sort of shakiness where the universe is not what we just expect, those are chances for us to both risk and lose something in some cases, but also to test ourselves and to discover who we are beyond the sort of normal constraints of everyday life. And James was interested in both thinking about life as a risk, but also as a reward, and both of those are equally ours when we explore them at the limits. And and I found that to be pretty instructive when I was reading James or rereading James for the umpteenth time and thinking about my mom being like, oh, man, I wish she could still get around. And what is interesting is that James suggests that even when our mobility and our actions are inhibited, we still have the ability to do small actions. And those small actions do matter for our emotions and for how we’re feeling. So I take that as pretty interesting.”

On Rebind

“[On Rebind] you get to go read Walden with me or you’ll be able to read The Tale of Two Cities with Margaret Atwood or Salman Rushdie doing Candide. And you’re basically getting a one-on-one masterclass with an expert about a classic book. And you get to ask any questions that you want and you’ll get pretty good answers. And thankfully, they’re originally and authentically sourced from the commentary that we’ve gotten.  There are 13 books up on the site. There’ll be 27 by the fall. Well, I’ve learned that it takes that AI has this. a very, very bad rap that it is not particularly popular and people are very suspicious. And people don’t mind interacting with a generic AI bot if they’re dealing in insurance, if they’re insurance agencies or maybe they’re pharmaceutical companies, they just wanna get answers about their drugs or something. But they don’t want to hear a generic AI bot wax eloquent about great books or poetry or things that we really care about. And that’s where the authenticity really matters. And I had to convince these authors, John Banville who won the Booker Prize, Marlon James who won the Booker Prize, Atwood, Rushdie, Elaine Pagels who gave us the gospel or gave us commentary on the Gospels.I really had to convince these participants and commentators that we weren’t pirating anything and that we were distributing their words know, useful in authentic ways. So that was one thing. The second thing is that people like to talk about books. There are 50 million people involved in Bible study, and we’re going to put out the Bible this spring in this form. There are five million people in book clubs, and people like to hear other people’s thoughts about reading. And that’s something that I’m hopeful about in terms of turning this into a genuine group reading experience.”