Friendship, AI, and Authentic Connection

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 life from your Financial Advisor – a way of thinking about your values, goals, and well-being in one of the most important transitions of your lifetime.

Valerie Tiberius joins us from Minnesota.

__________________________

Bio

Valerie Tiberius is the author of What Do You Want Out of Life? A Philosophical Guide to Figuring Out What Matters (Princeton University Press, 2023). She is the Paul W. Frenzel Chair in Liberal Arts and Professor of Philosophy at the University of Minnesota, where she has taught since 1998. Her work sits at the crossroads of philosophy and psychology — specifically, how both disciplines illuminate what it means to live well. She is the author of four additional  books, including The Reflective Life: Living Wisely with Our Limits, Well-Being as Value Fulfillment, and her widely acclaimed ). Her newest book, Artificially Yours: Real Friendship in a World of Chatbots, is forthcoming from Princeton University Press in May 2026. Valerie has received grants from the Templeton Foundation and the National Endowment for the Humanities, and her ideas have reached audiences through MPR News, numerous podcasts, and speaking engagements worldwide.

__________________________

For More on Valerie Tiberius

What Do You Want Out of Life? A Philosophical Guide to Figuring Out What Matters

Artificially Yours: Real Friendship in a World of Chatbots (availabkle for pre-order – coming in May)

Website

__________________________

Mentioned in This Episode

Why you should swap your bucket list with a chuck-it list

__________________________

Retirement Podcast Conversations You May Like

The Art of the Interesting – Lorraine Besser, PhD

The Good Life – Marc Schulz, PhD

Living for Pleasure – Emily Austin, PhD

Life in Three Dimensions – Dr. Shige Oishi

____________________________

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 1.6 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.

______________________________

Wise Quotes

On Values and Alignnment

“I think living in accordance with your values, living up to your values, doing the things you value, that just is what it is to live a good life. So the good life is the life in which you fulfill the best values for you… Life goes well to the extent that we pursue and fulfill our appropriate values over time — not the values society assigns us, but the ones that are emotionally authentic, reflectively endorsed, and capable of being sustained together.”

On Hidden Goals

“If you don’t acknowledge [a hidden goal] and it’s there, it will come up and haunt you at some point. It will come and hit you in the face.”

On Adding a Chuck It List to Your Bucket List

“Sometimes you have to give yourself permission to say, I’m never going to do that. I’m just not going to do it. And for my dad, it was learning Spanish. He really thought an educated person – my father has a PhD, he’s very educated – an educated person knows a foreign language. And then at some point in his 70s, he was like, it’s not happening now. I got better things to do.  And he does have other things to do. So I think the Chuck-it list is important for the specific goals we have. And sometimes there’s a whole big value that needs to be chucked. If your capacities change, there are things you just can’t do anymore.”

On Listening to Your Emotions

“I really think it’s worth spending some time reflecting on what matters to you and thinking about whether you’re tracking it – because I think people have a tendency to get caught up in trivial crap that doesn’t really matter. And then the second part is I think that, although I’m recommending being reflective and thinking about these things, that process has to be informed by our emotions. So you can’t just sit and think about what you believe. You also have to listen to your body, they would say if you were in a yoga class. But there’s something to that. Listen to what your emotions and motivations are yelling at you from the bullpen.”