Regrets of the Aging with Chip Conley, Dan Pink & Steven Morris

Video replay of Regrets of the Aging with Chip Conley, Dan Pink, and Steven Morris

I was thrilled to have this conversation with Dan Pink and Chip Conley. We embarked upon an adventure into and through the complex, daunting, often confusing worlds of midlife and regret.

Two titans of wisdom, New York Times bestselling authors Dan Pink and Chip Conley, joined us as guides.

Dan’s books have illuminated secrets of human potential, reminding us that we can be more than just a paycheck.

Chip is on a personal odyssey of reinvention in midlife, where he challenges us to break free from conventions and embrace the possibilities of transformation.

Quotes, Takeaways, and Questions:

Here are some key quotes and takeaways from the conversation between Steven Morris, Dan Pink, and Chip Conley, discussing the themes of midlife, regret, and the societal narratives that surround aging:

Key Quotes:

  1. Chip Conley on Midlife:
    • “Midlife is the most derided, least appreciated life stage that exists.”
    • “Midlife became a thing. But all it ever got… was a brand of the midlife crisis in 1965.”
    • “Midlife is… less of an age… it’s more of a stage and it’s really the stage between early adulthood and later adulthood.”
  2. Dan Pink on Regret and Decision Making:
    • “Most of our decisions don’t matter that much. It’s okay to be good enough.”
    • “Knowing which decision matter and which decisions don’t is powerful.”
    • “(Regret) is one of the most, arguably the most common negative emotions that human beings have. And so you have to ask yourself, why does it exist? And the reason it exists is because it’s adaptive. It’s useful if we treat it right, and we haven’t been treating it right.
  3. Steven Morris on Midlife, Risktaking, and MEA:
    • “For those of us in midlife, we have an increased propensity to lessen the risks that we take in our world. And I would say midlife is the time to take some beautiful risks, especially in those things you may regret not doing.”
    • “My experience at MEA … was that I found a group of kindred people through a system and a process that helped me come to ground with embracing midlife.”
  4. Chip Conley on the Midlife Narrative:
    • “The popular sort of pop culture myth of midlife is Kevin Spacey in American Beauty… It’s the idea that… you’re trying to go back to adolescence.”
    • “What if midlife is not a crisis, but instead it’s a chrysalis?”


  • Midlife is Misunderstood: The conversation highlights that midlife is often misunderstood and underappreciated, with many people feeling stuck due to societal expectations and accumulated obligations.
  • Regret and Decision Making: Dan Pink suggests that while many decisions in life are not critical, recognizing the ones that truly matter is essential. He also touches on the universality of experiences across different demographics.
  • The Power of Regret: The discussion explores how regret can be a powerful tool for learning and growth, especially during midlife.
  • Need for New Narratives: There is a call to shift the narrative around midlife from one of crisis to one of transformation, akin to a chrysalis stage where significant personal growth can occur1.
  • Community and Support: Steven Morris shares his experience at the Modern Elder Academy (MEA), emphasizing the importance of community and support systems for those navigating midlife challenges.
  • Language and Identity: The conversation also touches on the need for new language and concepts to describe and navigate the midlife stage, moving away from the idea of being a “human doing” to a “human being.”

Some Questions for You:

  • From Chip: What do you know or have done now that you wish you’d known or done ten years ago? So lock that into your brain. And then here’s the really powerful question: moving forward, ten years from now, what will you regret if you don’t learn it or do it now?
  • From Dan: Regret is arguably the most common negative emotion that human beings have — And so you have to ask yourself, why does it exist? And what can you do about it? (Hint)
  • From Steven: When you look back on your life and career, what are the moments that make you truly proud, the moments where you felt you were truly making a difference? In other words, What do you least regret doing as you rewind the game tape of your life?

In summary, I was thrilled to host this deep-dive conversation into the complexities of midlife and the societal constructs that shape our understanding of this life stage. Chp and Dan both challenged the notion of the midlife crisis, promoted the idea of midlife as a transformative period, and underscored the importance of community, new language, and the power of regret in shaping a more positive and proactive approach to aging.

About the speakers

Chip Conley

Chip Conley is on a mission. After disrupting the hospitality industry twice, first as the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and then as Airbnb’s Head of Global Hospitality and Strategy, leading a worldwide revolution in travel, Conley co-founded MEA (Modern Elder Academy) in January 2018.

Inspired by his experience of intergenerational mentoring as a ‘modern elder’ at Airbnb, where his guidance was instrumental to the company’s extraordinary transformation from fast-growing start-up to the world’s most valuable hospitality brand, MEA is the world’s first ‘midlife wisdom school.’

Dedicated to reframing the concept of aging, MEA supports students to navigate midlife with a renewed sense of purpose and possibility.

A New York Times bestselling author, Conley’s 7th book Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age is about rebranding midlife to help people understand the upside of this often-misunderstood life stage and he was asked to give a 2023 TED talk on the “midlife chrysalis.”

Dan Pink

Daniel H. Pink is the author of five New York Times bestsellers, including his latest, The Power of Regret: How Looking Backward Moves Us Forward. His other books include the New York Times bestsellers When and A Whole New Mind — as well as the #1 New York Times bestsellers Drive and To Sell is Human. Dan’s books have won multiple awards, have been translated into 44 languages, and have sold millions of copies around the world. He lives in Washington, DC, with his family. 

Steven Morris

Steven Morris is an expert brand and culture builder, advisor, author, and speaker. He has worked with 300+ brands, including Google, Sony, Habitat for Humanity, Amazon, International Trademark Association, NFL, and MLB. Over his 29 years as an entrepreneur, he’s served more than 3,000 global business leaders.

His most recent entitled The Beautiful Business: An Actionable Manifesto to Create an Unignorable Business with Love at the Core, has been dubbed “The Artist’s Way for Business Leaders.”

He reaches 25,000+ readers through his blog and writes about branding, culture, leadership, and the intersection between work and life as a contributing writer for Retail Observer, Wisdom Well, Business Week, Brand Week, Conscious Company Magazine, Communication Arts, HOW Magazine and MarketingProfs.

When he is not supporting leaders in building beautiful brands and businesses, Steven explores his wholehearted participation in life as a husband, father, artist, surfer, motorcyclist, and beekeeper.

Regrets of the Aging — Transcript

Steven Morris
Welcome to Regrets of the Aging. Today we’re going to embark upon an adventure into and through the complex, daunting, often confusing worlds of midlife and regret. Two titans of wisdom. New York Times bestselling authors Dan Pink and Chip Conley join us as guides.

Dan, your books have illuminated secrets of human potential, reminding us that we can be more than just a paycheck.

Chip, Your personal odyssey of reinvention in midlife challenges us to break free from conventions and embrace the possibilities of transformation.

For those of you who don’t know me, I’m a brand and culture advisor. I run a company called Matter Consulting. My passionate work is guiding organizations globally to fuse their brand, culture, and business strategies together into a tapestry of success.

Today, I’ll be donning a very different hat. I’ll just be playing the cajoler — your friendly neighbor of cajoler, your questioner, or your guide for this particular conversation called, “Regrets of the Aging,” and it’s inspired by Bonnie Ware’s famous blog and book called “Regrets of the Dying.” In that Bonnie writes that there are five regrets that she heard people consistently profess from their deathbeds.

I won’t go into what those regrets are. I encourage you to read that. But the good news is that as far as I can tell anyhow, none of us are sending postcards from the afterlife just yet. That means it’s perfect timing to explore the intersection of midlife and regret. While we can still do something about it. So I wonder.

I wonder aloud; is midlife a when? Is it a how? Is it a what? Is it a why? And is regret a friend or foe? And I wonder what the power of regret can teach us about learning to love midlife. So let’s get into foundations.

Chip, what the heck is this mysterious, wondrous thing called midlife? And why does it matter now?

Chip Conley
Well, first of all, Steven, thanks for organizing this. And Dan, you know, you’re one of my heroes. We have a mutual admiration society. And of course, we just you know, we are we’re. I was just saying to Steven that I just maybe this language exists, and you would know better than I would, but I think what I’m experiencing today is post-publish depression, not postpartum depression.
And do you know have you heard that before? Is that a thing under the sun? Okay. Yeah, I felt it today. Interestingly enough. It’s only been ten days since the book came out. But it’s it is that sense of like, okay, now I can just, like, melt and so, we may talk today a little bit about what it means to be an author, too.

So let’s talk about midlife for a minute.

Dan Pink
D.C. statehood and what it means to be an author. So we’re just going to bring down the collective moon here to the floor. Man. So that’s going to be great. Friday afternoon, you’re going to enter the weekend feeling like crap. Thanks.

Chip Conley
Shabbat shalom. Yeah. So, you know, the bottom line is that midlife is the most derided, least appreciated life stage that exists. It’s the Rodney Dangerfield of life stages. I’ll be brief, but there are three life stages that sort of emerged in the 20th century. Adolescence did not exist as a word until 1904 in a popularized form. And after that, when a book came out called Adolescence, all of a sudden, we had child labor laws.

You’re not an adult at puberty. We’re going to have more public in junior high schools and high schools. And adolescence has gotten a lot of love in the last hundred years. Retirement really became a thing in the 1930s between pensions and Social Security. Ultimately, later, AARP retirement communities. Guess what? And especially in D.C. with AARP, retirement gets a lot of love.

Well, when it comes to midlife midlife. It was created in the 20th century because the average longevity in the U.S. was 47 in the year 1900, and it was 77 in the year 2000. So we added 30 years of of longevity in one century. So midlife became a thing. But all it ever got, and I am really honest here, the only thing I ever got was a brand of the midlife crisis in 1965 when a Canadian psychologist who studied 15 midlife men wrote a very innocuous routine.

Chip Conley
That’s it.

Steven Morris
15?, wow.

Dan Pink
It’s a terrible paper. Yeah. It’s just a terrible study. The guy’s name is Elliott Jaques. Just to name names. It’s an absolutely atrocious paper. The idea that the midlife crisis became this phenomenon based on such a thin and largely meaningless piece of work is astonishing. But, okay, you start.

Dan Pink
It’s already. Go, go, go, go, go.

Chip Conley
Go, go, go.

Dan Pink
I’m just. Yeah, I’ll be your amplifier for. For that.

Chip Conley
Yeah. So I think so. This life stage didn’t get much loud, didn’t get much study, and it’s gotten more study over time. But the bottom line is it is a period of the time that I would describe is less of an age like some people say it’s 35 to 75. That’s a long marathon. But it’s it’s more of a stage and it’s really the stage between early adulthood and later adulthood.

What a surprise midlife would be, that bridge. And the question is, how long does that bridge last? And the longer we’re on the earth, the longer midlife lasts. And so as we have the tech burrows and Silicon Valley biohacking their way to, you know, cheating, death, middle, middle age could last 50 or 100 years someday. I mean, so we better get a clue about this life stage.

And so I’ve really spent the last six years studying it, you know, starting the world’s first midlife wisdom school and the modern older academy and then writing this most recent book. So that’s those are my thoughts on midlife.

Steven Morris
Yeah. Very good. Dan, in your most recent book, The Power of Regret, you Offer, which I found very serendipitously interesting as, as Chip’s topic is, you know, hitting your Good Morning America and everything. You offer this the Golden Years fallacy, which challenges the notion that midlife is a period of decline settling down. Help us with some myth-busting there.

Dan Pink
Well, I mean, I think a lot of the missed but myth-busting done by Chip, both in word and deed. I mean, the deed is the modern elder, an academy that he started, which is actually taking, you know, affirmative steps to help people navigate the stage, which, as he’s saying very astutely, was never considered a stage before.

And that his book, which helped me as someone who is in that, you know, who is who is in that cohort. And I think there is a real need for sense-making here. You know, we just we don’t have the we don’t have the institutions right now to help people navigate this. And I don’t even think we have the terminology that I think one of the things that Chip was saying is that midlife is in some ways a kind of a meaningless, meaningless term.

So, you know, what we have is we have, let’s go back to Chip’s numbers, 1900. What do you say that longevity was? 47, 40, 46, …in 2000, it’s 77. Okay. So we added 30 years, but we didn’t change the structure. We basically had education for many work and then retirement. And then we added 30 years and we know what to do with that. And so and so I think that’s a hugely important question. It’s a question for our economy. It’s a question for our social health.

It’s a question for our our physical health. And it’s a question that, you know, again, making ultimately is something that I’m dealing with myself. And I think that, you know, one of the one of one of my principles as a writer is always extrapolating from your own experience because you’re not that special. And so I feel like if I’m grappling with this, then then lots of people are.

And that’s why I think that Chip’s book is so is so helpful in figuring out the language, figuring out some of the actions, figuring out some of the new rituals that we can do in this stage of life to just find effort to find our footing.

Steven Morris
Very good. You know, Chip, what are the you know, we have all these sort of negative connotations around, you know, what midlife is or isn’t or it, which mostly is laced with, in my opinion, confusion or lack of awareness. What are some of the notions about this? My midlife that you wish can be just stripped from the lexicon of our society from every day?
And what would you replace them with?

Chip Conley
So the popular sort of pop culture myth of midlife is Kevin Spacey in American Beauty, The Red Sports car and dating your daughter’s best friend in high school. It’s the idea that.

Steven Morris
Or, you’re smoking pot in the garage and working out.

Chip Conley
You know, smoking pot in the garage and working out. And it’s sort of like what it is in that in that form. And I’m not saying that form doesn’t exist, but it is really the minority that forms suggests that you’re not in middle essence, which is a gerontology world word that speaks to the idea of the transitions of midlife, which are hormonal, physical, emotional and identity transitions, just like you have them in adolescence.

But what it’s suggesting is that you’re trying to go back to adolescence. So. So and I’m not saying that that doesn’t happen, but it is it is not the majority the way the majority of people experience midlife. So if you’re privileged enough to be able do it that way, you can the general way that people experience midlife is they feel stuck and they feel stuck on all levels.
They feel stuck in the expectations they had of themselves that they’re not living up to. They just stuck in the obligations that they have put upon themselves. Because we spend the first half of our life accumulating obligations, resonates stuff, children stuff, physical stuff in our homes. And the second half of our life is supposed to be about anything.

But nobody told us. Nobody. Nobody gave us the memo and said, okay, I’m in midlife. It’s time for my great midlife edit. So we feel stuck that way as well. And we feel stuck in identities and roles, even archetypes. You know, my archetype I get stuck with is the hero. I got to go save the day. Someone else am I be the caregiver for someone else.

It might be the explorer, but there’s like, no matter where I am, I end up in that archetype because I haven’t done the good work to sort of see like, you know, the Carl Young, you know, which is in Joseph Campbell, sort of the underbelly of the hero’s journey, where you’re going to the shadow side. Midlife is when you actually get face to face with your shadow side.

And my book has one chapter. It’s as someone said to me at a book signing a couple of nights ago, Chip, that was your favorite chapter of the book? It was my least favorite chapter of the book. And that’s what she said. And she’s a longtime Academy MBA alum. And she just said, it’s that chapter. Which chapter? It is the chapter that is called.

I’ll just tell you what it is right here. So basically, the book has an introduction and an afterword, and then there’s the 12 reasons why life Gets Better with Age. And this particular chapter is called I Understand How My Story Serves Me. And it’s really if there’s an alternative way to describe that chapter is if I understand how my story serves me, it is creating your own hero’s journey and understanding it.

And so it’s pretty deep. I mean, you can frankly write a whole book on that, what’s in that chapter. But I think that we get stuck sometimes in our story, in our narrative, and in our archetype of how we show up in the world without realizing that that’s a that’s a costume that we can disrobe if we want to.

The popularized myth around midlife crisis is that you lose your mind trying to be an adolescent again. The reality, having had over 4000 people from 47 countries come to me and me being kid, you know, almost every one of them. The reality is that it’s not so glamorized. It’s really more people feeling stuck.

And often part of the reason why we have, you know, a doubling of the suicide rate of people in midlife in the last 20 years is because sometimes people feel like when they’re that stuck, there’s no way to unstick. And therefore, my only solution is to escape and I lost five male friends to suicide between 2008 and 2010, ages 42 to 52, all of them unrelated.

So it wasn’t like there was a group suicide or anything like that. All of them individuals who are going through the Great Recession and they were stuck in one way or another. So this is a public health crisis, you know, and on some level. And last, because you get me started on this stuff, I’ll just go forever is Becca Levy.

I wanted to create a living laboratory for her work. She’s a Yale academic, really well-respected in two different departments at Yale. And she’s been able to show in her research that when you shift your mindset on aging and again, midlife is when you start to realize you’re aging. It’s not that it’s not that you’re not aging earlier. You’re aging from the day you’re born, but in your teens, in your twenties and thirties growing, and then you have midlife like, I’m not going anywhere, I’m aging.

And the fact that you’re aging means you need anti-aging creams. It means you need to start thinking about death. And I don’t want to think about that. But Becca Levy has shown that when you get midlife offers to shift your mindset on aging from a negative to a positive, you gain seven and a half years of additional life, which is more additional life than if you actually stop smoking at 50.

That’s four years of additional life or you started exercising at 50. That’s three years of additional life. So it’s actually more than those two combined. But we have all kinds of pieces, public service announcements about stopping smoking and starting exercising. We have no pieces that have a pro-aging message. And that’s why I wanted to write the book, and that’s why I wanted to create MEA, to create a pro-aging product that helps people to reframe their relationship with aging.

Steven Morris
And part of what I hear you talking about there, Chip, is, you know, in this stuckness is that part of the stuckness is, you know, we had this previous identity of ourselves typically that in well, I speak from my personal, you know, the narrative here. It comes from primarily vocation and family. Right. So, I’m the CEO of a company that I built, founded, grew, and sold.

And then I ran into this crisis thereafter, which was often not the CEO of that company. Who the heck am I? And that was in my fifties when I did that. And so that part of that stuckness is as I begin to age or recognize that I actually am aging and maybe even embrace that I’m here in midlife who am I now and what does that actually mean and who do I turn to for support, help, guidance, direction, and even conversations around these things?

Steven Morris
It seems like MEA is an island. A safety net for those types of conversations for those who haven’t been there. I can speak to it firsthand.

Chip Conley
Yeah. To what was your experience? Because you did actually go,, Steven,,? You were there during the time I was not there if I’m not mistaken. And what do you know? What was the kind of conversation that was going on?

Steven Morris
Yeah, there was a lot there. I attended a week hosted by Lori Schwanbeck, who was a wonderful facilitator. So, I primarily went down (to MEA) because she was running it. And she’s wonderful. And that had to do with Leadership in Uncertain Times, which of course, we’re living in right now. But you can also say leadership of the self in uncertain times is midlife, right?

So for me, the richness of the conversations in a community setting that, you know, you guys have put so much thought into the curriculum and the journey that you go through at any particular week. It allowed for creating a sense of psychological safety, first and foremost.

One of the things you do at MEA is when you “introduce yourself,” you’re not introducing your resume. You’re introducing the you “if you really knew me, you know this and this and this about me,” right? And I found that that humanity or the human perspective was utterly refreshing and somewhat daunting because we’re just not used to introducing ourselves in that type of way, especially in a circle of, you know, 20 or 30 people. So my experience was through the journey of that week. It was absolutely eye-opening. And I went the week after, I think it was the week after my 60th birthday.

And yeah, and Chip, I contributed a blog post that had to do with the reflection around that, which was really more, and if anybody read that, but it was more confusion around, well, you know, I have this narrative in my mind about the past. How much of that is actually true, and how much of that is just, you know, personalized or my, and or am I rethinking what I thought actually happened?

Right. So but my experience to your question about MEA was that it I found a group of kindred people through a system and a process through the curriculum that helped me come to ground with, frankly, for the first time at 60, embracing midlife.

Chip Conley
Yeah, yeah, I think. Go ahead. Go ahead, then.

Dan Pink
no. I just think I mean, one of the one of the things I like about this this this book is that it gives a language to realms where I feel like we’ve had sort of gaps in our lexicon. And one end when you were talking, Steven, what we might when you talk about that circle and you’re talking about it, we say like, who are you?

And you immediately say what you do rather than who you are. And so Chip talks in the book about going from human. Most of our era, parts of our lives, you’re a human doing.

Chip Conley

Dan Pink
To a human being. And I think that this idea also of accumulating because that in some ways I think it’s very similar to doing I’m going to I’m going to. You think it’s almost like we’re all these the military figures and what we’re trying to do is going to rack up as many medals as we can to adorn our chests.

All right. We’re going to accumulate we’re going accumulate all of those. So when you look at me, you see that’s who I am. And then at a certain point in our lives, if we want to be, then this is not really who I am. Maybe one of these things is that here is who I am. And there is I’m going to teach you guys what the 50 cent word here, Right.

You ready? Yes. Now, you know, if you’re anybody in an automobile, I encourage you to buckle your seatbelts because I’ve been using a word. All right, It’s coming your way right now. And that word is, I think that what was happening with Stuck is actually liminality. All right. You’re in a liminal state. You’re you’re you’re you’re moving from one thing to another in the same way that adolescence is that way.

And the more we have a way to say, this is what’s going on, the more we can we get, we can make peace with that. So I guess just just for the for the folks listening here. So if you’re in this midlife, one of the things that helped me was thinking of it, okay, I was an accumulator.

Now I’m moving toward more. I was like mostly accumulation, some editing. Now the balance has shifted. I was mostly a human doing. Now I’m moving more toward a human being. And even you don’t use this as explicitly, but my goal was to be smart. Now my goal is to be wise. And I think that that way of thinking is actually really helpful.

And giving people the language to describe these their own sort of inchoate feelings is actually really powerful.

Chip Conley
But let me give you some more similar language here. And so, yes, buckle up again, guys.

Dan Pink

Chip Conley
Liminality., you know, is a great word.

Dan Pink
Word of the day. Yes. I have a little calendar for the word of the day, and liminality happened to be today’s word.

Chip Conley
It’s a good one. It’s completely appropriate here. And you throw out three or four more. And then, I really want to go into regret. I really want to I want to personally, I’d love to hear Dan talk about why he decided to write that book of regret. And but I will say, here are some other words to consider, because we do need to change the language.

This idea of being pro-aging. Well, I think anti-aging. There’s an anti-aging industrial complex. Yes. And it’s a $500 billion. You’re business is actually mostly an anti-women business because it’s about actually making you feel bad about your face and making you feel bad about the things that a plastic surgeon or creams could do for you. And so a pro-Beijing message is, I think, needed.

And so there’s that. There’s also a piece of language that I’ve been through in the book that I’m saying on stage a lot more. And that’s to be age-fluid. So we know about gender fluid, but age fluid is sort of similar in the sense that when you’re age fluid, you are in all the ages you’ve ever been or will ever be.

You are not specific to a chronological age or a generation. In the past you would have called that ageless. Ageless because age, if you say someone’s ageless, is suggesting that age is a bad thing, like, you’re ageless, which, like, you don’t have the affection of age. Well, no, ages can be a good thing. There’s a lot of reasons that age is a good thing.

So I like age fluid because I think it’s something all of us can own. Just age fluid. Okay, fine. You know, it’s sort of cool to middle, middle lessons. I mentioned earlier about adolescence and middlescence. We’re going through the kind of liminal adolescence of adulthood. And yet when we were doing that as kids, we were doing it with a peer group and a support network network and a system and a roadmap.

We have no fucking roadmap. Excuse me, We have no fucking roadmap for middle lessons in midlife. And yeah, that’s what we need. And then finally, I would say midlife and I gave a TED talk last year that, you know, that was three and a half minutes long. I mean, God, like the shortest TED talk ever given about the midlife crisis, because it’s not so much a crisis.

It is, Yes. The future of happiness research is pretty conclusive. 45 to 50 is the low point of adult satisfaction in one’s lifetime. It declines from our early twenties, bottoms out at 45, 50, and then with each decade after that, we get happier. So what if midlife is not a crisis, but instead, it’s a chrysalis? It’s that time between Caterpillar and Butterfly, where it’s dark and gooey and solitary, but it’s also where the transformation happens.

And what if we can shift that narrative? Because if the future of happiness is true, we’re getting happier after 50. So why don’t we actually have that message out there more? So those are some of the pieces of language. I hope you enjoy them.

Steven Morris
I’m curious about the midlife crisis language, if you know, in sort of the stuckness perspective, if people have any hesitancy to embrace that term? You know, people have been through a true crisis in midlife, you know, losing a job, you know, getting laid off from a career, having to shift or, you know, some other health crisis.

For folks who maybe have faced that type of perspective or a set of experiences, do you get the sense that they’re having a hard time embracing this crystal mindset?

Chip Conley
I had one person create a bumper sticker for me saying we’re not all butterflies but that there’s truth to that. We’re not we’re not all butterflies and all parts of our life. Actually, there may be certain parts of our life where we’re stuck in that fucking chrysalis the rest of our lives, and we never get out of it.

But what I see over and over again and I and this is where there’s I have some hope. First of all, people think that what’s going on for them is not normal, and they’re the only ones going, yeah, not true. And secondly, sometimes the people who have the most terrible external circumstances happening to them are the ones who are able to break free from the habits and the mindsets and the ways of being that have been holding them back.

And, you know, our Jewish shaman, who did you get to know Sela while you were there? Stephen Yes.

Steven Morris
Yeah, we spent some wonderful time together.

Chip Conley

Steven Morris
So often to any, you know.

Chip Conley
Yeah, yeah, yes. Saul Kuperstein, he’s our shaman. He also is our construction manager. And he cuts my hair, which is a pretty easy job. Wow. And it and so several so lost everything at age 50, everything in his life. You know, is he lost his parents, he lost his money. He became he had to go bankrupt.

And then, all of a sudden, he realized inside of himself that he’d always had this voice. He had these premonitions when he was a kid. And then he realized and he loved going to Baja. He was from Pueblo, Mexico, And he’s like, I went to this place that feels very ripe for me because when you’ve lost it all, you have nothing to lose.

And he became a shaman and a really great one. And so sometimes we get to that place and, you know, it’s not easy. And yet the more we have going on, the more we can get through the unraveling. And that’s what Brene Brown calls it. Brene says, Chip, have you ever looked in the dictionary and the word ravel?

Because I said when I heard her say midlife unraveling, nobody wants to unravel. That sounds like you’re losing your mind. And she says, when you look at the dictionary under Ravel, it means something so tightly wound you can’t get it undone. A ravel. And that’s how someone that’s the stuckness that sometimes people feel is the Ravel of stuckness.

And so sometimes you have to be hit over the head a bunch to say like, okay, surrender, I’m ready for, you know, the next chapter is pretty different than the last one. So but it’s not easy. And that’s part of the reason that I write books about this and create, you know, MEAA, because when you’re going through all of that, you know, a coach could be helpful.

A therapist can have a spouse or best friend can be helpful. But if you have a program that specializes in navigating midlife transitions, cultivating purpose, reframing your relationship with aging, and figuring out how to cultivate your own wisdom, then that’s worth something. So, I want to hear about regret. Why did you write? Why did you write that book?

Chip Conley

Dan Pink
Because I was having a midlife crisis. No, I’m sorry. It’s I mean, it’s very it’s very tightly connected here, you guys, because this is not a book that I would have written in my thirties. And it’s a book that in my fifties seemed kind of inevitable because I was at a point in my life, which is, you know, the jarring realization that some of us have where we say, you know, even if I am age fluid and healthy and exercising and, you know, eating well, I still have more of my life behind me than ahead.

And that’s a jarring thing. I mean, you get over it after a while, but when you first realize it, you sort of go through the stage where you’re like, no, that can’t be true. And then you’re like, my God, this is terrible. And it’s like, Gosh, I got to do something about this. And so and so, as a consequence, I had more of my life to look backward.

Then I had to look forward. And when I look backward, like everybody, there were things I wish I had done. There were things I wished I hadn’t done, and, you know, I knew that nobody wanted to talk about regret. And so when I very sheepishly, after an experience at my elder daughter’s college graduation, came back and started talking to people about regret, I, you know, mentioning my own regrets, I discovered that everybody would want to talk about it then for the same reasons, the same reasons that Chip is talking about, that we’re looking for navigational help, we’re looking for a cohort, we’re looking for the realization that we’re not alone.

And so that took me on to this long exploration of the science, of this emotion, and this emotion is revealing. It’s not an emotion entirely or that for people in their midlife, but it’s it’s a prominent midlife emotion. It’s a prominent human emotion. And if we treat it right, it can be a force for good.

Steven Morris
Why is it that we don’t that people don’t want to talk about regret? You know, it feels like it’s sort of this, you know, taboo type of thing that, you know, what what is is that it?

Dan Pink
It’s because we’ve been sold a bill of goods. We’ve been sold a bill of goods about positivity. We’ve been told that we should always be positive, never be negative, that we should always be, always look forward to never look back. And that is terrible advice. What is the actual science? There are 60 years of research on this, and what it tells us is that we should be positive most of the time.

Positivity and positive emotions are very good for us. Positive emotions are, as Chip was saying earlier, actually extremely useful for healthy aging. But we don’t want to have only positive emotions because negative emotions are functional. And the problem is, is that we’re never taught how to deal with negative emotions, particularly what social scientists have told us revealed the most common negative emotion that human beings have, which is that sinking, gut-wrenching feeling when you look backward and said, “If only I had done that, if only I hadn’t done that.”

It is one of the most common emotions that human beings have. It’s one of the most it’s arguably the most common negative emotion that human beings have. And so you have to ask yourself, why does it exist? And the reason it exists is because it’s adaptive. It’s useful if we treat it right, and we haven’t been treating it right.

So we’ve gone in two directions. We either ignore them because we’ve been sold a bill of goods on positivity, so we put our fingers in our ears and say, No regrets. No regrets. Always, always be positive. Never always look forward or we get captured by them. We wallow in that we. We stew in what they get. They bring us down.

And what we should be doing is looking at them. We should be thinking about them, analyzing them, using them as a signal, using this data. And when we do that, as I said, we have 60 years of evidence that it can help us in a range of things. So, so, so so regret is adaptive if we treat it right.

No one’s ever taught us how to treat it right. And it could be that one reason for the stuckness, one reason for the analogy is that people have regrets and they don’t know what to do with them.

Chip Conley
Yeah, so what should you do with them? And I have two questions. What can we do with them too? And then secondly, there’s the regret is the thing you didn’t do, and then there’s the regret, the thing that you did that you wish you hadn’t done. Talk about the difference between those two, because I know the research on that.

You know, I’m giving you a pinata here so that you can break open.

Dan Pink
Yeah, but I’ll throw Chip a pinata here because it affirms a lot of what you’re in. So let me let me talk about that, Chip, and then we’ll talk about the remedy. This is one. Okay, so let me let me I want to I just want to. I just want to show my work here.

So once again, for this book, as I said, there are five or six decades of research in social psychology, cognitive psychology, personality psychology, and neuroscience. There’s actually some economics about this emotion, so we know a lot about it. The second thing that I did myself is I conducted the largest public opinion survey ever conducted on American attitudes about regret.

The American Regret Project has some very important insight there, which I’ll get to in a moment. And then I also have collected regrets from people all over the world. So we now have a database of over 25,000 regrets from people in more than 100 countries. And that is very revealing to know the chips pinata. I did a pretty sophisticated public opinion survey because I was interested in demographic differences in regret.

Do men have different regrets than women do people of color have different regrets from white people? Do people with high degrees of formal education have different regrets and people in low degree? So I did this pretty sophisticated and very expensive public opinion survey with a very large sample to try to find those demographic differences. And there weren’t that many.

I said that which is sort of interesting in and of itself, however, and this is the punch line, the big the most, the clearest demographic difference had to do with age. And here’s what it was when the people in their twenties tended to have equal numbers of regrets, of action and inaction. Equal numbers of regrets about what they did and what they didn’t do.

But as people age and the early to the lower side of middle age, 35, but certainly when you get to 45, 55, 65, game over, it’s a technical knockout. Overwhelmingly, people regret as they age what they didn’t do more than what they did. Regrets of. When you get to be my age, and I’m in my late fifties, regrets of inaction outnumber regrets of action nearly 3 to 1.

Yeah. Yeah. And that tells us that tells us a lot. So that’s, I think, a really important thing when people in this midlife crisis, people’s regrets are predominantly things they didn’t do, in part because other kinds of changes are increasingly acute emotional intelligence. Our move toward wisdom is allowing us to make sense and reconcile with certain kinds of action.

Regrets that I hurt somebody. You know what? Now that I’m wiser, I’m going to go back and make amends for things that I did that might have gone awry. I can repair them in some way. But when I didn’t do something, yeah, you can’t really do anything. And that’s what sticks with people that that in that universalism that stuck in this there are regrets of inaction that people that that somehow people feel singular only them and they don’t know what to do with them.

Chip Conley
I want to I want to bring one thing up and then let Dan go back to the remedy piece. Because I’ll tell you one of the ways we address this. Is that okay, Steven?

Steven Morris
Yeah, Yeah, please go ahead.

Chip Conley
I wanted to say that one of my favorite questions so MEA is dedicated to really creating a safe crucible for having life-changing conversations. And so one of my favorite questions we ask is the following: What is it that you know now or have done now that you wish you’d known or done ten years ago? So lock that into your brain.

And then here’s the really powerful question moving forward. Ten years from now, what will you regret if you don’t learn it or do it now? And at age 57, I’m 63 now. At age 57, that’s how I started to learn how to surf. I was living in Mexico, not too far from the surf break. Never had learned to surf.

Okay, it’s getting harder at 67 than 57. I mean, to. Similarly, I started learning Spanish at 57, even though there is a bumper sticker mantra in my head saying I’m too old to learn a foreign language. The fact is it would be easier. At 57, the 67 and I was living in Mexico part time, so I got to learn the language.

So anticipated regret is a form of wisdom. Being able to imagine the regret you will have is, I think, the is the definition or not. The only definition, but a partial definition of someone who’s wise. Because actually when we’re younger, we don’t we’re not able to anticipate regret so much. We’re sort of more focused on what’s in front of us.

And so those are just, you know, that’s part of my remedy. But I want to hear that. How would you.

Steven Morris
Both go as far as to say that anticipating regret is the antidote to experiencing regret in the future?

Chip Conley
It it could be. I mean, I don’t think the only one.

Dan Pink
Yes. Yeah, I think that it depends. I think it’s powerful, but it depends. And to I this is not this is not the remedy, but it’s it’s responsive to Chip’s question and it goes back to what I was saying before, which is always extrapolate from your own experience because you’re not that special. I think based on my research, again, this database of 25,000 regrets from people around the world, I think we can easily anticipate, we can easily predict the kinds of things that people will ten years from now very easily, because I have because what I found in this database of 25,000 regrets, these are not this is not a it’s not a dozen people on their deathbed. These are 25,000 people from over 100 countries sharing a big regret. And what we found is that there are four key regrets that people have. One of them is that is is if only I’d done the work. So small decisions early that accumulate to terrible consequences later. I spent too much and saved too little. I didn’t treat myself, I didn’t eat well and didn’t exercise, and now I’m out of shape or I have a health problem.

One of them huge one. Bonus regrets You’re at a juncture in your life and you can play it safe or take the chance. And when people don’t take the chance, not always. Most of the time they regret it. So bonus regrets. If only I’d taken the chance. Moral regrets. You’re at a juncture. You can do the right thing.

You can do the wrong thing. You do the wrong thing. Most of us, most of the time regret it because most of us are good. And then finally, connection regrets. If only I had reached out. You have a relationship that was intact or should have been intact. It comes apart. You want to reach out. You’re you feel awkward about reaching out.

You don’t reach out. And then it’s too late. And so and so. All of these and so all so. So to answer your question, Stephen, there is a lot of research on anticipating regret. And the thing is, we can drive results crazy with that. All right? If we try to minimize our regret about every decision we make, we will go nuts.

All right? Because even today, I had to make all kinds of decisions, even today, Friday after Friday in Washington, D.C., I had to make what I had to. What do I have for breakfast? my God. Well, I regret having cereal or I regret having a yogurt. Should what shirt should I wear? Should I wear a long sleeve shirt?

Should I wear well, what time should I have lunch? When should I go for my make all kinds of decisions? All right. The me of ten years from now is not going to give a shit about 99.9% of the decisions I make today and every day. But the me of ten years from now is going to care a lot, as Chip is saying, because he’s talking about some boldness regrets the me or the Chip or the Steven of ten years from now.

If you have meet that person and you do not and and you spent the last ten years and you haven’t built a stable foundation for yourself or your family, the people you care about, you have ten years from now is going to be pissed if you haven’t taken that shot. What do you mean? You are ten years to learn surfing and you didn’t do it and you live in frickin Baja and you’re not studying Spanish either.

What the hell is wrong with you, man? I’m doing the right thing. If. If if you. Here’s the thing. Most of us are good. Most of us want to be good. So if I take the low road in something the me of ten years from now is going to remember that and have some words with me. If I don’t reach out to people who I care about, the me of ten years from now is going to have some words.

So so we have so we can make very strong predictions about what we will regret in ten years. And the truth of the matter is, is that here’s the thing that’s hard to get our minds around. Most of our decisions don’t matter very much, but they really don’t. But some of them matter a lot, you know? And so what we need to do is we need to like, anticipate the really, really big regrets and just chill out about like what shirt you’re going to wear or whether, you know, it’s like I like, you know, it’s like, I have to get a roofer for my house.

I want the very best roofer in Washington, DC. You know, if I get the second-best roofer in Washington, DC, my house is going to be fine. Yeah, You know, in ten years. And I’m not going to you know, I’m not going to you know, I’m not going to care. So maximize on and anticipate regrets about stable foundation, about boldness, learning, and growth.

The Chip is saying about morality and about love, and everything else doesn’t matter that much.

Steven Morris

Chip Conley
And I’m that love when you know, just a quick and still like you to take us to death for a second. Frank Ostaseski, who you know is a very famous guy, wrote a book called The Five Invitations. He was an MEA Faculty member, and he started the San Francisco Zen Center, Zen Hospice. And there were thousands of people through they’re dying days. And he said that the question that often comes up in not in exactly this form as someone’s getting toward death is, ‘Did I love well?’ and ‘Was I well loved?,’ and it’s that connection piece and that’s the thing that people are ruminating in at the end.

No, Bonnie’s work is somewhat different than that. I mean, she has her five regrets. Do you want actually do you have those?

Steven Morris
I’ll see if I do.

Chip Conley
If you don’t, then don’t worry about it. But yeah, her’s are often a lot of hers that relate to things that they wish they’d done. Or yeah, I think one of them is very much about the person I could have been there, you know, it’s not just my doing, but my the person I could have been like in terms of who I showed up in the world.

Chip Conley
But I actually think the connection piece of it, the fourth one that you cite, makes a lot of sense. Back to you, Steven.

Steven Morris
Dan, in your in your book, you have this this photographic negative thought process that you that you walk people through in order to figure out what the good life is. Can you shed some light on that?

Dan Pink
Yeah. Yeah. And it’s, and we’ve been talking about it, I mean, and the other thing, just to echo what Chip is saying and deceiving, what you’re saying is that when we talk about love and connection, you know, Bob Waldinger at Harvard and Mark Shultz, who wrote a book called The Good Life based on Grant’s study of, you know, the largest longitudinal study of human flourishing ever conducted.

And they said many times that you summarize that’s that that decade-long study in basically a word love. Yeah, people know a lot.
Steven Morris
I’ve got Bonnie’s five regrets, by the way —

  1. I wish I had the courage to live the life true to myself and not the life others expected of me.
  2. I wish I hadn’t worked so hard.
  3. I wish I had the courage to express my feelings. You guys both talk about the feelings in both of your books.
  4. I wish I had stayed in touch with my friends.
  5. I wish I had been let myself be happier.

Chip Conley
Let myself be happier. Isn’t that interesting? The way the language is, Let myself be happier. It’s almost like happiness is a state, but I just wasn’t giving myself the license to experience it.

Steven Morris

Dan Pink
I mean, a lot of it. Or a lot of it. A lot of it comes down to. A lot of it comes down to. So certainly the connection, the connection to other people, you know, you know, Waldinger is in the Grant’s studies, basically happiness is love, full stop. And we see that a lot in the agent. We see that a lot in the research on aging.

What how do people how do people flourish when they’re when they’re aging they have decent physical health. But that’s actually not the most important thing. They have a purpose. They believe in something. They have people who they care about, who care about them, and they’re physically active, and they have a positive attitude. And that gets you most of the way that you don’t need metformin, you don’t need rapamycin, you don’t need that crap.

You just, you know, you need.

Chip Conley
Isn’t it interesting, Dan, that we have the tech rose of Silicon Valley with their biohacking and their psychedelics and these are the things that are going to make us live forever. And yet it’s the simple kinds of things of feeling, a sense of belonging.

Dan Pink
Exercise. Exercise. Yeah. Stay engaged. Have people you love and who and who love you have a purpose, believe in something and you’re good. Now again, you know I have to leave. I’ve got to leave in 2 minutes to get my blood transfusion. So I have like, a 17 year old whose blood gets transfused into mine. So I have no I mean, it’s like it’s not it’s really it’s really it’s really not that hard because it goes to it’s a really goes to these fundamental things.

What do we want out of life? And this is Stephen’s question. You know, here’s the thing that’s so interesting about regret that again, let’s go back to the point that that most of our decisions don’t matter and we don’t even remember them. Okay. So if we go back if I were to ask any of you to go through the decisions you made last Wednesday, truly most of them you don’t remember.

All right. Most decisions and actions you take, you do not remember one week later. But there are certain decisions and especially indecision, certain actions, certainly inactions that you remember from a year ago, five years ago, ten years ago, 25 years ago, 40 years ago. That’s a very strong signal, ladies and germs. That’s to go back to Rodney Dangerfield.

That’s a very strong signal that’s telling you something. And what it’s telling us, and this is my argument, is that when people tell what they regret the most, they’re telling you what they value the most. Yeah. And so if people say, I regret instability, you value stability. If they say I regret not being bold and taking a chance, it means they they value learning and growth.

If they say I regret taking the low road and cheating, they regret more. They value morality. If they say I regret losing connection, it means they value love and and that’s it. And so it ends up being that ends up being fairly similar. And I’m wondering, this is a question more for Chip is like whether this move toward editing away from accumulating to editing, from smarts to wisdom, from doing to being helps us see what really matters.

Dan Pink
And I think that it does.

Chip Conley
Well when you’re in the midst of being on the hill on a treadmill and you’re running fast in your pursuit of happiness, you don’t have time to reflect and you don’t have time to be curious. And so what what you know, first of all, time and space is good for asking deeper and bigger questions. Secondly, when you’re in your virtual mode and you’re living in your normal habitat, you stick with your habits.

And it’s when the the apple cart gets upset that you are forced to ask the question what really matters? You know, I had a flatlining speech, you know, just finished cancer cancer treatment two weeks ago. Three days afterwards, I was in on the Good Morning America show and then Today show that two days later, that was a lot to handle.

But the fact is, when I found out that my cancer diagnosis had gone to stage three, did I change how I was death or impending death or the prospect of death, an organizing principle for life? It absolutely is. And when I had a flatline experience from an allergic reaction to an antibiotic at age 47, it woke me up to the fact I’m not happy in my life right now.

I used to be happy. I’m not happy now. I’ve got a come because you out of these. I feel like a faker because I am running a company based on joy and I’m not feeling it. And I had to figure out how to sell that company at the bottom of the Great Recession. So it is true that pain can be a motivator and a catalyst for making change.

It’s unfortunate. And again, that’s part of the reason I create. I mean, because you can be going through these painful life lessons that are the future, that are the raw material for your future wisdom. But who’s helping you metabolize those and and see despair equals suffering minus meaning to to sort of create an emotional equation about Viktor Frankl’s work for men Search for meaning When you can try to find the meaning in the despair you actually have, feel less of the despair when you when you feel it, when you can have the meaning in the midst of the suffering, the despair declines.

Chip Conley
So it’s it’s making meaning, which is something that we get better at as we age based upon social science research. Again, one of the 12 reasons why we get better life gets better with age. These are things we get better at, but we some of these things have to be trained and there practices that people have to actually live up to.

Dan Pink
Exactly. And no one. And that’s the thing. This is the same thing with regret. Nobody teaches us how to do it. Yeah, yeah. No one ever, you know, like, it’s very clear to me that the solution is not to ignore your regrets, not to wallow in them, but to confront them. But no one ever tells us how to do that.

It’s it’s it seems pretty clear, I think, from from Kip’s work and from other kinds of things that that midlife is a stage of life that is under threat. It is undervalued underrecognized and that is very similar to adolescence and that it’s in some ways inevitable for a lot of people that we’re all going through it, and yet we don’t know how to do it.

No one ever taught, no one ever touches, no one ever tells you how to do it. And so and so when we offer some kind of assistance in sense making, which I think is what MBA is doing, I think which is what your book is doing, it’s it’s helpful because people will, with a little help find their way.

They don’t have to be led by the hand, but they need they need to have don’t know what the right metaphor is. They need to have someone who is maybe catching their back or they need to have someone who’s walking side by side or whatever. But the right people need that. They don’t. They don’t. There is there’s this tendency to feel alone, to feel singular, that you’re the only one.

And that is almost never the case.

Steven Morris
Yeah. Yeah. I wonder, you know, are you an advocate for regret circles, you know, sharing regrets or once one does, like, acknowledge that? Look, I’ve got some regrets. I feel like I want to process them. I don’t know how to do that. Like, how do you how would you advise people in terms of, you know, making, you know, either circles of connection or, you know, having conversations.

But, you know, people who you trust in order to process regrets.

Dan Pink
Or do all kinds of things that you can do, including including that. So so one of the most important things to do in processing your regrets is to practice self-compassion, to treat yourself with kindness rather than contempt. A lot of times, especially human doing, when we’re in the human doing stage of life, when we make a mistake, when we screw up our self-talk, the way we talk to ourselves is brutal.

Yeah, And and here’s the thing. There’s no evidence that’s effective. If it were effective, I could endorse it. I always believed it was effective. I am. I am. I am. The the the the king or the prince of vicious disparaging self-talk. And the thing is, there’s no evidence that it works. What works? It’s also there’s very little evidence of sort of patting yourself on the back works.

What works of self-compassion? Treat yourself with kindness rather than contempt. Don’t treat yourself better than anybody else, but don’t treat yourself worse than anybody else. So that’s one step. The second step is exactly as you’re saying, Stephen, which is there’s a very strong case to be made for disclosure. We tend to think it’s a form of sense making when we talk about our regrets.

And even there’s some evidence when we write about our regrets for just 15 minutes a day, for three days, what we do is we take this abstraction, this negative, amorphous feeling, and we make it concrete through our words, and that’s less menacing. We also have, you know, of the forecasting error where we say, if I reveal my regrets, people will think less of me when in fact we have other evidence showing that in general, not all the time, but a lot of most of the time people think more of us.

They admire courage, they admire vulnerability. And then finally, here’s the most important thing, though. It’s like this is not an exercise in sort of doing this. You have to draw a lesson from it. You have to, you know, you so you treat yourself with compassion rather than contempt you disclose to make sense of it. But then you have to say, what did I learn from this and what am I going to do about it?

Yeah, that’s really important. It has to be pragmatic and practical and actionable. And when people do that, we have again, a pile of evidence, you know, I mean, it’s very good for business leaders. We have evidence in social psychology that people who lean in to their regrets can become better negotiators, they become better think, they make fewer thinking errors.

We also have evidence that that people find more meaning in life when when when they do that. And so it’s a systematic forgive yourself, talk about it. Draw a lesson from it. Yeah. And when we do that, it’s a powerful emotion. It’s not a debilitating emotion. It’s a it’s a useful emotion. It’s an engine for forward progress.

Steven Morris
Would you also be an advocate for having accountability partners. So let’s say you’ve gone through that regret process and now you’ve made a proclamation or commitment to go out. I’m going to learn Spanish, I’m going to learn surfing. And you know, in that circle of communication that you’ve had. But to what degree does the science say around accountability partners to support that process?

Dan Pink
I’m not sure about the science on that. It seems intuitive, like a good idea. Are you I mean, do you like those, Steven? Are you a fan of those kinds of things?

Steven Morris
I think they can be depending on what it is. So something like Surfing or Spanish, it’s done out in the public, yes. But, if it’s something that has to do with a point in self-reflection, then maybe I wouldn’t want to have an accountability partner for that.

Dan Pink
I’ll tell you something that I do. And and, you know, your mileage out there in America may vary, but it’s something that I’ve done. And I did it. I did it in response to some of the things that Chip is writing about in response to this sort of liminal state. So so one of the things that we know, again, is that people, human beings are pretty good problem solvers, but we tend to stink at solving our own problems.

We’re much better we’re much better at solving other people’s problems than our own. And so there’s some good years in which someone like self distancing as a problem solving technique. What’s more is that you also see among men, especially middle aged men, that they’re not very good at making or maintaining friendships, and that that’s a very enriching part of lives.

Dan Pink
And so so I started this thing with six other middle age guys here in Washington, D.C. We call it an advice club, and we meet every basically every five or six weeks at somebody’s house. We have some food, we have some alcohol.

Steven Morris
Sometimes more than a bit.

Dan Pink
More a lot of our fair bit of alcohol and and what we do is we people come and they say, you know what, I’m having some people run companies. So it’s like, man, I got this employee, I don’t know what to do. And the rest of us will give some kind of advice. Some people have issues maybe with their kids, some people have issues with.

We have a lot of people in the kind of state, my God, I’m in this job and I’m not sure I want to stick with it. What do I do? And and one of the things that we first of all, it’s a great way to maintain and form friendships. So you have some people who didn’t know each other, who are now, I think, very good friends, which is a lovely thing to say.

And the other thing is that you you learn more about you learn quite a bit about yourself when you give advice. And people are pretty good at solving your problems. Yeah. And giving you like very sensible and very sensible things. And so this.

Chip Conley
Is what peer to peer networks like radio are very popular.

Dan Pink
Or vintage, whatever. It’s but this is this is basically a little bit more kind of. Yeah, but very, very like it’s very kind of friendship social oriented with it with the it’s basically a drinking club with these other features. No, it’s a no, but it’s, but it’s a very meaningful thing and it’s it’s one of the smartest things I’ve done in the last couple of years.

And, and what it suggests is that that need for connection and and I just want to say just one quick point here, because I think this exemplifies it, is that a lot of times this is this is one of my takeaways from I’ll give you two takeaways of my own life from from the research on especially connection regrets is number one is that we have a I think we have in the parlance, again, we have to narrow a notion of what love is.

We tend to think about love mostly as romantic love and romantic love is extremely important to people in people’s lives, their love. They have the romantic love, the sexual love they have for their partner and their spouse. Hugely important. But there’s other kinds of love people have, like incredible love for their friends and incredible love for other people in their life.

That isn’t romantic love, but it’s that is an incredibly powerful and meaningful part of their lives. And we don’t talk enough about that. And so and so a lot of the connection regrets were not about romantic love. They were about friendship, they were about siblings. And and I think that I think that tells so to me, it’s like a take away from me.

It’s like, whoa, I think about it made me think I have this circle of friends from from college. And it made me think in a way that I never had before. People I made friends with, you know, 30 plus years ago as a freshman in college, you know, and we stayed friends all these years, is that I love these people.

I mean, I don’t you know, again, I don’t really think about I never really thought about that explicitly. But of course, I love these people. And we have a love for each other. And that’s a powerful yeah, it’s a powerful kind of love. It’s a different kind of love than I have for my wife, but it’s also a form of love.

And so one of the things that I see with the Connection regrets is that and I changed my behavior is that if I’m ever at a juncture where I’m thinking of someone who I knew I was friends with at a certain point and I haven’t talked to them for a while, and I ask myself, should I reach out to Fred or Maria if I reach that juncture, I know the answer to the question.

Dan Pink
Always reach out.

Steven Morris
Always reach out!

Dan Pink
Absolutely, always reach out. If you’re if you’re at that juncture where you’re saying, should I reach out or not, you answer the question, always reach out. And I’m someone who is not very good at that. And I’ve completely changed my behavior on that.

Steven Morris
Yeah. In your book, the stories that are encapsulated within that to talk about these women and you bring them back multiple times, who they went to, they were like best friends and they went 20 years and you know, they’re both saying like, God, I love this person. I, I really wish I could reach out. They’re like a part of me read like a novel.

And I wanted to, like, you know, reach out, and say, just please do it right now.

Dan Pink
What what read as a novel unfolded in reality, because I basically lost it at one point. There’s a woman named Cheryl who’s talking about this old friend that she had. you’re such good friends. And I’m not sure I should reach out because it’s been 20 years and we sort of drifted apart and she’s going to thing. It’s really weird if I reach out and she’s not going to care and, you know, I’m trying to be sort of like, you know, a decent like sort of reporter writer, like not trying to intervene in people’s lives.

And so I interviewed her a couple of times. And finally, just lots of. Cheryl, what the hell? Yeah, of course you should reach out. What are you thinking? You know? And then she reaches out and then she reaches out, you know? So I get an email from her, like, two weeks later. Hey, hey. You’re not going to believe what I just did.

I’m like, What? And and she’s. I just reached out to Jen and and, and anyway, so this story kind of the story kind of unfolded. But again, the takeaway, I think, for all of us is that when in doubt, reach out.

Steven Morris
Yeah, you ask this beautiful pivot question of her that I thought, no doubt she’s going to reach out after this, which is how do you think she would feel if you reached out to her and she would be like, she’d be over the moon or I think you asked that the other way around, right?

Dan Pink
Yeah. Yeah, I would. How did you, Jen, reach out to you? How would you feel about it? I was like, my God, I’d be so touched. I would be. I would tears Well, in my eyes, it would be the greatest day of my life, you know? And then you sit there going.

Chip Conley
Yeah, exactly. That’s a beautiful question.

Steven Morris
All right, let’s pivot a little bit. So, Chip, your book just launched. You know, it’s my belief that when you create a piece of art like a book, it’s yours, until you send it out into the world and then it’s no longer yours. It’s up to society to determine what it is, but it also becomes a teacher for you.

So I wonder. I know that book has only been out for a week and you’ve been, you know, on the road show and all that kind of thing. What has launching the book taught you about the book and about yourself.

Chip Conley
That the experience of going through midlife is, well, not well, very personalized. There’s some universal truths that people are going through, and we need to elevate the voice of these, because when I get people the book’s actually a short read, which is nice. All my books sometimes, like I get very academic because I’m not an academic, and so I want to pretend that I’m an academic, have a chip on my shoulder, so to speak.

And this one I really abbreviated and people can read the book in 5 hours and you can fly across the country and read the book and yeah, you don’t have to go fly cross-country to read the book. That’s to be a very expensive book. But the bottom line is that people are reading it fast and that still and they’re saying you’ve you’ve spoken words and and pieces of language that reflect who I am.

I feel like you were studying my story and telling my story. And so that gives me a sense like, okay, we’re on a path here. It’s just that we have to do a better job of elevating these stories and helping to show the road map. And the road map is not the game of life roadmap, where there is just one path through life.

There are multiple paths, but there are great questions to ask that can help you to turn to determine at your midlife crossroads which path that you should be going on.

Steven Morris
Yeah, Beautiful. Dan, same question to you. What has the power of regret taught you about the book itself and launching it out into the world? What have you learned? And maybe what have you thought about regret since it’s come out?

Dan Pink
Well, I mean, I think one of the things that I’ve come back to is sort of what Chip is saying about the this almost thing that is like we all have these very idiosyncratic experiences, but within them is are some universal things. And there is there is much more universally, Steven, and I think we sometimes give credit for and universality in our experiences across race and gender and socioeconomic status.

I think that’s I think that’s of the things. The second thing is, as something I was saying before, is most of our decisions don’t matter that much. It’s okay to be good enough. And maybe that’s a form of midlife wisdom. Maybe that’s a form of my transition from editing. It’s form of editing in a way, and most decisions don’t matter, but edit down the ones to the ones that really matter.

So most of our decisions don’t matter, but a lot of a matter of law and knowing which decision matter and which decisions don’t is, is is powerful. So I think that that is those that’s to me that some of the big the big takeaways. The other thing about it is is that you know the that people that continue willingness that people have to to to talk about these things they start sheepishly almost whispering it and then that’s all they want to talk about.

Steven Morris
Just pivoting here the the opposite of regret. So if you look back in your life, your career, you play the game tape of your life. What are the things that you both least regret either doing or not doing? Chip I’ll ask you first.

Dan Pink
Besides this interview?

Steven Morris
Yeah, you could and you can include the interview. You can actually go on and on about this. Yeah. Thanks, Dan. Appreciate that.

Chip Conley
I think one of the things we need to teach kids at a younger age is how to trust their intuition, intuition and their gut instinct. And I when I look at the things in my life that are the opposite of regret, were I what is the what is the word for the opposite of regret? Dan, Do you ever rejoice?

Rejoice, Yeah, rejoice, rejoice doesn’t feel quite Rejoice is a good one and it doesn’t feel like it quite has the like. Yeah, yeah. You feel the self-satisfaction of it because you can rejoice about something in your self satisfaction. Regret is a word often that speaks disappointment. It could be someone else. Could you put that on you regret? Regret is very personal.

And so whatever that opposite is. I think that the decisions I’ve made along the way that especially where people have said that’s a really bad idea. Three of my chapters in my career starting a boutique hotel company at age 26 by buying a, you know, hey by the air, a motel in the Tenderloin, all my Stanford business school classmate, that’s like you’re just an idiot.

And then joining after like a long hotel career, joining Airbnb at a time when nobody had heard of it. Like, that’s a terrible idea, but that’s never going to go anywhere. In those days, youngsters, millennials are going to hate you as a boomer. Well, they’re wrong. And then starting in the air like chipper, you’re like retirement age.

Why are you doing this? It’s like, So I guess I would just say where I most admire my willingness to do something based on my instincts, that’s when I think I feel the best is because I did not succumb to the popular popular wisdom or the popular perspective, or people who are trying to protect me.

Steven Morris
Beautiful. It speaks to Bonnie’s first regret, which is I wish I had the courage to live the life true to myself and not that others expected of me.

Chip Conley
That’s exactly right.

Steven Morris
Yeah. You’re.

Dan Pink
And what the question is, what do I not have least regret? At least regret marrying my wife, leaving the traditional world of employment 25 plus years ago to do my own thing? Those are the two best decisions that I ever made. Bar none. Everything good in my life has flowed from that trip. Truly.

Steven Morris
Yeah. Somebody asked me to post the regrets.

Dan Pink
What about you, Steven?

Steven Morris
The number one answer is the same as yours. My wife and I have been married for 30 years. There is nothing as potent, as powerful, as beautiful as a mate that gets you, that you get them. That you can go through life together with raise children together. Certainly. It’s not always easy, but she has been my greatest friend, my greatest ally, my greatest supporter, my greatest challenger.

And I hope that I’ve been there for her as well. So that I mean, no question that has been my least regretful thing.

Chip Conley
Is the new piece of language you have to come up with, Guys.

Dan Pink
Yeah. No, I don’t know.

Chip Conley
Yeah, it’s it’s actually we need to go to the dictionary. Is it the antonym of of regret? That will be very interesting to see what comes up. I know we have to go soon. There. There’s somebody asked a question in the Q&A about.

Steven Morris
Yeah, there’s two I’ll read.

Chip Conley
Okay. Okay. Yeah.

Steven Morris
Do, do The midlife suicide numbers include females and what is the difference between genders?

Chip Conley
Yeah, they do. It used to be that men. So they sometimes the language this is crazy success. A successful suicide means someone actually dies as opposed to trying to trying to take your life but not dying in 20 years ago, five times as many men succeeded at suicide than women. Today it’s four times. So what that means is that the percentage and part of it’s because the percentage women who the number of women who are actually trying is actually growing.

But it it is. And it’s also partly because men tend to you to use guns more than women. And whereas women often use pills and so you can survive the pills can’t survive a gunshot to the head very easily. So that’s the unfortunate news on that one. I’m glad to have another question because I don’t want that to be the last one.

Steven Morris
Yeah. Yeah. There was the only one other question that we have right now is can we post Bonnie’s list of regrets?

Chip Conley
There we go I’ll get.

Steven Morris
I just shared it to everyone.

Chip Conley
That’s a good one to end with.

Steven Morris
Yeah, it is.

Chip Conley
But, you know, suicides are a big issue. And I think when we have to be very thoughtful about in terms of how we’re dealing with it, because it’s certainly a death and there’s lots of forms of suicide, death by despair, whether you’re drinking yourself to death or getting hooked on opioids, etc.. Are other forms of suicide, but they are not as quick parting wisdom.

Dan Pink
Dan, on, you know, you can you can learn from your lesson of your own life. You can learn from the lessons of other people’s lives. And one of the lessons of all the people who submitted their regrets from all over the world is take a shot, reach out to people you love, do the right thing. And you know, you that it’s like.

It’s like it’s like the it’s like the longevity thing. It’s like you want to be you know, you don’t you don’t need pills. The creams. Just take a shot, reach out the people you love and do the right thing. And your life satisfaction is probably gonna be pretty high on chip.

Chip Conley
Be the mirror, Be the mirror. If you want love in your life, be their love is going to be joy. And joy will be that joy. You want an ambition in your life, be their ambitions. You know you want to be the victim in life. Guess what they are. You know, that’s what? That’s what the mirror you’re going to have out there.

So we you know, we need to we need to learn how to be the mirror.

Steven Morris
Very good. Gentlemen, thank you so much. Yeah, that would be well, a couple of things here. First, reach out to your heroes like I’ve done here and appreciate the time and the wisdom that you guys both shared and. I think, you know, here, as those of us in midlife, we have an increased propensity to lessen the risks that we take in our world.

And I would say midlife is absolutely the time to take some beautiful risks, especially in those things that you regret not doing.

Dan Pink
Get everybody get a surfboard and a Spanish tutor and move into move out of your your chrysalis into this new, exciting stage of life.

Chip Conley
Beautiful. All right. Thank you, guys. Thank you. Thanks, Everybody!