Young and Profiting with Hala Taha - Daniel Pink: Turn Your Biggest Regrets Into the Ultimate Self-Improvement Tool | Human Behavior | YAPClassic

Episode Date: August 7, 2026

Regret is an emotion deeply rooted in human nature, but it may be your greatest tool for personal development. After his daughter’s college graduation prompted him to reflect on his own missed opportunities, Daniel Pink spent two and a half years studying what thousands of people around the world regret most. In this episode, Daniel explains the psychology of regret and how entrepreneurs can use it to make better decisions, take bolder action, and build a life with fewer “what-ifs.”  In this episode, Hala and Daniel will discuss:  (00:00) Introduction (00:30) What Sparked Daniel's Regret Research  (03:31) The Psychology Behind Regret (09:33) Regret as a Self-Improvement Tool (12:53) The Problem With the "No Regrets" Mindset (24:07) The Four Universal Types of Regret (32:40) Action vs. Inaction Regrets (34:59) Life Lessons From Studying Regret (40:15) The Right Way to Process Regret (47:03) How Regret Fuels Personal Development Daniel Pink is the author of seven bestselling nonfiction books about business, work, motivation, creativity, and human behavior. His books include The Power of Regret, When, A Whole New Mind, Drive, and To Sell Is Human, and his work has sold more than five million copies and been translated into 46 languages. He previously served as chief speechwriter to Vice President Al Gore and hosted the National Geographic series Crowd Control. Sponsored By: Indeed - Get a $75 sponsored job credit to boost your job's visibility at Indeed.com/profiting Shopify - Start your $1/month trial at Shopify.com/profiting. Northwest Registered Agent - Get a complete business identity with Northwest. Visit northwestregisteredagent.com/YAPFree and start using free resources to build something amazing.  Mindstone - Master practical AI skills without the complexity with Mindstone’s AI Competency Programme. Head to experience.mindstone.com/yap and get 10% off.  AT&T Business - Stay connected with reliable, secure internet built for entrepreneurs. Switch to AT&T Business at business.att.com.  HoneyLove - Treat yourself to the most advanced bras and shapewear on the market. Save 20% off Honeylove by going to honeylove.com/PROFITING! #honeylovepod ElevenLabs - ElevenAgents by ElevenLabs helps businesses deliver better customer experiences. Start with a demo at ElevenLabs.io/profiting Quo - Bring your calls, texts, and contacts together in one place. Try Quo for free, plus get 20% off your first 6 months when you go to quo.com/profiting.  Resources Mentioned: Daniel’s Website: danpink.com  Daniel’s Book, The Power of Regret: bit.ly/-Regret  YAP E50 with Daniel Pink: youngandprofiting.co/E50  Active Deals - youngandprofiting.com/deals  Key YAP Links Reviews - ratethispodcast.com/yap YouTube - youtube.com/c/YoungandProfiting Newsletter - youngandprofiting.co/newsletter  LinkedIn - linkedin.com/in/htaha/ Instagram - instagram.com/yapwithhala/ Social + Podcast Services: yapmedia.com Transcripts - youngandprofiting.com/episodes-new  Entrepreneurship, Entrepreneurship Podcast, Business, Business Podcast, Self Improvement, Self-Improvement, Personal Development, Starting a Business, Strategy, Investing, Sales, Selling, Psychology, Productivity, Entrepreneurs, AI, Artificial Intelligence, Technology, Marketing, Negotiation, Money, Finance, Side Hustle, Startup, Mental Health, Career, Leadership, Mindset, Health, Growth Mindset, Habits, Positivity, Human Psychology, Critical Thinking, Robert Greene, Chris Voss, Robert Cialdini 

Hey, Yap, fam, you know that voice in your head that says, oh, I wish I did this differently, that voice that most of us just ignore. Well, today's guest says that voice is actually trying to help you. Daniel Pink is the bestselling author of multiple books. And today he's going to be talking about regret and teaching us how regret can make us better, bolder, and more intentional. So listen in, Yapam. It's time to stop running from regret and start learning from it with Daniel Pink.

Welcome back to Young and Profiting Podcast, Daniel. Hey, it's great to be here, Holla. Thanks for having me. Yes, I'm super excited for this conversation. So last time you're on the show, it was back in December of 2019. It was for episode number 50. It was called The Science of Perfect Timing. And that episode was actually one of my all-time favorite episodes on Yap.

Everybody who listened to it loved it. And I have a feeling this conversation is going to be equally as good because, in my opinion, you are the epitome of what a great podcast guest is. You're so knowledgeable. There's no fluff when you talk. Everything is backed up by science and research. And so you are the ideal Yap guest for that reason. And here at Yap, we love to go super deep on a specific topic.

Today's focus is going to be on regret. You are the author of seven books. And your latest book is called The Power of Regret, how looking backward moves us forward. So let's jump right into this topic of regret. Last time you're on the show, we covered your career journey extensively. So anybody who's tuning in and interested in that can go back to episode number 50. highly recommend that episode. And so, Daniel, I'm pretty familiar with your work. And usually you write a book because you're very curious about the topic yourself. And you start to research that topic. You call this MeSearch. So let's start there. What was the genesis of this book, The Power of Regret? And what initially got you curious about this topic. Well, once again, I've fallen down the trap of me search because that's what this is again.

So here's what happened. So in 2019, I had one of those moments in life that you get to when you get to be my age. I'm in my 50s. And I had a kid graduate from college. So that's kind of a jarring experience because you wonder, like, how do that kid grow up so fast? And how am I possibly old enough to have a kid who's graduating from college? And in the course of this college graduation, which is very long and lengthy, and my daughter's last name starts with P. It was a lot of waiting around.

You know, inevitably, your mind wanders. And as my mind was wandering, my thoughts turned to my own college experience. And I started thinking about what I regret it. There were a lot of things I regretted. I wish I had worked harder. I wish I had been kinder. I wish I had been a little gutsier, you know, taking more risks. So these thoughts were kind of, you know, tiptoeing through my head when I came back.

And I wanted to discuss them with other people. But I knew that nobody wanted to talk about regret because it's taboo. So against my better judgment, I very, very, very, very, very sheepishly mentioned a few of these regrets to a few people. And I discovered that everybody wanted to talk about regret, that it was a kind of topic that there was this kind of damn breaking that people said, oh my God, you have that regret. I have that regret too. And they wanted to talk about it. And I think what's interesting from a writer's perspective is that sometimes I'll raise an idea or concept. And people like, OK, that's nice.

All right, whatever. You know, what are we having for dinner? And that happens a lot. And that's cool. But this is one where people like literally, and I mean this literally, I mean the literal definition of literal. Okay. They leaned in. That is, their bodies move forward in wanting to discuss this.

And that's a very good sign. And so that took me on this two year, two and a half year journey to try to make sense of this emotion. which I think that we've misunderstood profoundly, and that also gives us hints about how to lead a better life. Yeah. And I feel like I learned so much in this book. Like you said, regret is this like kind of misunderstood emotion. And to my surprise, it's very complex,

and it actually springs from an internal cognitive process. And so in the book, you talk about how humans are kind of like time travelers, because our brains have the ability to revisit the past and invent these alternative narratives and scenarios. And so I thought that was really fascinating. Can you explain that to us? So when we think about what regret is, I mean, it's certainly an emotion,

and it's an emotion that makes us feel bad. But it's also a process that is, and we should kind of be in awe of our ability to process regret. When you think about it exactly, as you said, when you think about it cognitively, you think about what you're doing with regret. Let's use my example.

So I say, you know, if only I had taken more risks when I was in college. What I do is I go back in time to when I was in college, all right? I negate what really happened, which was kind of being a little bit of a wimp. I think about something, and I replace that truth with a counterfactual. So let's say that I was playing a club-level sport, all right, rather than just wimp out, right? Instead of phoning it, I'm going to try to become like a very skilled basketball player and risk the injuries and risk the feelings of stupidity and not being good.

good enough and whatnot, rather than just retreat. All right. So I go back and negate that. Not only that, but I come back to the present. Now my present is reconfigured because I've changed the past. And now suddenly, I don't know, I'm like, you know, coaching a basketball team or I'm a better leader because I had more experience with a team sport or something like that. And so it's really this incredible process that we go through where we get in the time machine, we go backward, we negate what happened, we get back in our time machine, we go forward to

the present, and the present magically looks different because of what we done in the past. This is one reason why regret is a milestone in our development. That is, little kids can't do this. Five-year-olds don't experience regret because they can't think counterfactually. It's also why people with certain kinds of brain damage and brain lesions can't reason counterfactually. The more I think about what our brains can do, the more I'm kind of in awe of this lump in our head and how powerful it is. Yeah, and I want to dig deeper on counterfactuals because you brought it up, and it was a term that I've never heard of until I started reading your book. and it's super interesting.

So talk to us about counterfactuals and the main ones and maybe give us some examples. So basically what it means is that our brains allow us to imagine a scenario that runs counter to the actual facts. So, you know, you can go backward

and say, if I only had married Fred instead of Bob, all right? And so, wow, how would my life be different? There are two kinds of counterfactuals here. Okay, so I know you guys like to go deep. So there are two kinds of counterfactuals that are really important. One of them is what I call a,

what you can call a, downward counterfactual. Okay. So you imagine how things could have been worse. All right? So you say, oh, I regret that I married Bob, but at least I have these two great kids. Okay. So you find the silver lining. Okay. It could have been worse. I could have married Bob and not had any kids. All right. So at least, so at least make us feel better. Now, there's another kind of counterfactual, if onlys. All right? That's an upward counterfactual. factual or you can imagine how things could have gotten better. It could have been better. So you say, oh, if only I had married Fred instead of Bob, I would be living in a nicer community. I would have a

happy marriage. I would be financially secure, et cetera, et cetera. You imagine how things could have been better. Now, if onlys make us feel worse. But here's the dirty little secret. If onlys make us feel worse, but they also help us do better in the future. And they make us help us do better in the future because they make us feel worse. And regret is an if only feeling. Totally. Right. Regret is the quintessential if only. It makes us feel worse. This is why it's paradoxical, Holla. This is why people don't like it. This is why people like to proclaim, I don't have any regrets. I never look backward. I'm always positive. And the reason for that is that regret is unpleasant. But what we also know from, again, you know, if you look at 50 or 60 years of research,

in neuroscience, in cognitive science, in developmental psychology, which I mentioned before, in social psychology, a lot of experiments in social psychology as well. What it tells us is that regret is ubiquitous. It is everywhere. Everybody experiences regret. It's one of the most common emotions that human beings have. I can't emphasize that enough. Everybody has regrets.

If you don't have any regrets, it's a warning. It's a bad sign. It means that you could be five years old, which I guess that's not a bad sign. Like, you've got to grow up. It could mean that you have brain damage or lesions on the orbital frontal cortex of your brain or early onset Huntington's or Parkinson's.

It could mean that you're a sociopath. Those are truly the only people who don't have regrets. The rest of us have regrets. It's one of the most common emotions that human beings have. And this is sort of a puzzle, right? It's like you have this thing that is widespread, but it makes us feel crap. So you have to ask the question, well, why does it exist then?

Exactly. So we obviously evolved to have regret for good reason, right? It's kind of a survival instinct, I imagine. It makes our lives better in the end. We're not perfect organisms at all. We're not perfectly efficient, but there are adaptations that we've had. So you have to figure like, why does something that make us feel bad? Why is it everywhere?

Okay. It must do something. It must have some benefit to us, right? And you got it exactly right. The benefit that it has is that if we treat our regrets properly, it helps us do better. And not only a little bit and not only in a few things, but a lot of bit, on many things. And here's the key. If we reckon with our regrets properly, we don't ignore them.

We don't put our, when we feel a regret, we don't put our fingers in our ears and say, blah, blah, blah, blah, blah, blah, blah. I don't hear anything. That's a bad idea. But also, and this is also important, Hala, we don't wallow in them. We don't ruminate on them. We don't stew over them. We confront them, all right?

We use them as signal, as information, as evidence, as data. When we do that, again, we have the research showing that it can help us become better negotiators. So there's a lot of experiments where you put somebody in a negotiating session. then they do in their negotiation. They come out. The experimenters say, okay, I want you to think about what do you regret doing

or not doing into that negotiation? So they encourage people to invite this negative feeling, right? What happens next? They do better in the next negotiation. It helps us become better problem solvers. It helps us avoid cognitive biases like confirmation bias

and escalation of commitment to a failing course of action. There's some interesting research among executives, showing that executives who actually sort of embrace and acknowledge their regrets are better strategists than those who simply try to skate past them. It helps us find greater meaning in life. And so what we have here, again, just to distill this, make it a little bit simpler, is this. Regret makes us human and regret makes us better. Everybody has regrets, and the reason everybody has regrets is that if we treat them properly, they're incredibly useful.

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growing a business and still managing customer communication from your personal phone, it's probably time for an upgrade. Money's on the line. Always say hello with Quo. Try Quo for free plus get 20% off your first six months when you go to Quo.com slash profiting. That's QUO.com slash profiting. Quo.com slash profiting. When I was studying you, I heard that one of the main reasons why you went on this journey is because you heard this like no regrets kind of philosophy and culture that was going on. How everybody just wanted to be positive. You know, you're supposed to just accept your journey for what it is and never look back about the mistakes you made and just everything happens for a reason type mentality. So let's talk about that before we go even deeper on regrets and how to like, you know,

evaluate them right or wrong ways to do that. But let's talk about that first. What's wrong with the no regrets worldview? Okay. There's a lot wrong with it. But I'm going to try to be kinder and gentler in how I and how I bash it. The problem is that it is a woeful, fully misguided philosophy for a life well lived. And the reason for that is this. I'll give you an example of it. All right. So I have the people who I wrote about, you know from the book, who get these tattoos that say no regrets. So they believe in this philosophy that you should always be positive, never be negative, always look forward, never look back. They believe in this credo, this philosophy so ferociously, they have the message.

enshrined on their bodies. That's a commitment, man, all right? Like, you know, like, you got to believe in something to have a tattooed on your body, right? So, but here's the thing. If you say no regrets, you say, I never look backward. You might as well get a tattoo that says no growth, no learning, no progress. Nobody's getting tattoos like that. And so it's really, really misguided.

The key here is what we do with our regrets. And this is, I think, a bigger problem that we have, Hala, which is this. We, and I think it's an American problem more than others, we Americans have a problem with negative emotions. We don't know what to do with them. Here's the thing. Just go back and just again, positive emotions are great. I want to have a lot of positive emotions. I want you to have a lot of positive emotions.

I want all the app listeners to have lots of positive emotions. Okay, positive emotions are great. Gratitude and joy and elation and they're great, okay? They're part of what makes life worth living. But here's the thing. People shouldn't have only positive emotions. That's not healthy. All right, it goes back to what you were saying before.

We have adapted to the world. Negative emotions are adaptations. So if you think about this, I'll give you an example. All right, let's take fear. Fear is a negative emotion. Do I want to go, if somebody knocks at my office door, some weird person knocks at my office door, hey, Dan, I'll give you an operation. Hey, we're going to open up your head, but it's going to be completely no pain.

We're going to seal it back up perfectly. And what we're going to do is we're going to do a little tweak in your brain to ensure that you never experience fear again in your life. Do you want that, do I want that operation? Absolutely. Of course not. Of course not. because I don't, because when I'm in a burning building, I want to experience fear so I get the hell out, right?

Like, it's helpful. Again, I don't want to be burdened by fear. I don't want to experience fear all the time. That's debilitating. I don't want to experience, you know, think about an emotion like grief. The reason we experience grief is because we experience love. Okay, so I don't want to banish grief. I don't want to banish negative emotion.

I want to actually reckon with them. And I like what you said at the top of the show, Hala, is that there's evidence here, okay? This is not some kind of philosophy of mine. We have 50 or 60 years of evidence telling us that when you line up the emotions, all right, when you line up our negative emotions, you know, we're going to do a little police lineup. Fear, guilt, shame, you know, that regret ends up being the most common and the most useful. If we treat it right. if we treat it right. And again, we haven't been treating it right because what's happened is we're

totally over index and positivity. We think we have to be positive all the time. And when we, and when we're not, when we're not, especially younger people, when they say, when they feel negative, they feel regret, they feel bad, they say, wait a second, I'm feeling regret, I'm feeling bad. That's, that's terrible because not only is it make me, is it inherently, like, unpleasant, but I look around and everybody else is perfect. There must be something wrong with me and they get brought down by that. Rather than saying a negative emotion is a knock at the door.

Clunk, clunk, clunk, clunk, clunk, clunk. Someone's trying to tell me something. Let me listen, not drown it out, not get freaked out by it, but listen to it, learn from it and do better in the future. Yeah, and like you said, regret is so common and it's universal and it's normal, right? It's a normal feeling to have. It's just about how you manage it, how you profit. and what you do with that information.

Amen. So in this book, you did a lot of research yourself, but there was also years of research prior to that about regrets and the common regrets that people have. So can you talk to us about the research that was available before you started, and then maybe why you ended up doing more research and what you found?

Yeah. So I was also curious about what people regretted. I was really curious about that. And the reason I was curious is that when you looked at the existing evidence, most of it in social psychology. Initially, researchers said, oh, this is American sample, that Americans, oh, they have education regrets. Education is the biggest regret that Americans have. Scientists believe that for 20 years. And then somebody finally realized, like,

wait a second, all these studies showing that education is the biggest regret were done on college campuses with college students. And so, you know, if you had done all these research in hospitals, or maybe health would be the greatest regret. If you'd done it in banks, maybe, you know, whatever. So it's like, huh, maybe there's not something there. And so actually not that long ago, 16, 17 years ago, researchers started doing more systematic looks at what people regretted. And they found that people regret a lot of stuff.

It was all over the place. They have career regrets. They have romance regrets. They have finance regrets. They have health regrets. They have family regrets. It's all over the place. So that's the lay of the land.

So I said, I'm going to try to crack the code here. And so I did something called the American Regret Project, which is the largest public opinion survey of American attitudes about regret ever conducted. We did a brilliant, gorgeous survey of over 4,500 Americans modeling the sample, sort of configuring the sample so that it reflected the glorious diversity of the United States of America. And so I asked these people, tell me one of your big regrets. and then I had them put it into those categories, career, finance, romance, whatever, because I said, I'm going to figure this out. And I found, after careful deliberation and data analysis, that people regret a lot of stuff. It was all over the place, all right?

So now, that's the bad news. The good news is that I also did another piece of my own research, something called the World Regret Survey, where I simply set up a website, worldregretteurvey.com. where I gathered regrets from around the globe. And we now have a database of over 21,000 regrets from people in 109 countries. It's incredible. And once I looked at those, okay, basically just people offering their regrets, but by the thousands all over the world. And I didn't ask them to categorize it.

I just wanted to know their age, their gender identity, and their location. when I started reading through those regrets, I didn't read through all 21,000, but I did read through the first 15,000 of them. What I discovered is that there's something else going on, that trying to understand what people regret by those categories that I initially had thought is not the way to look at it,

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That's experience. com slash yap. Young improfitors, a few weeks ago, my main video editor put in his notice due to health concerns. Now, because it was an emergency and I wish him well, I was in a pickle. He was gone and there was nothing I could do about it. And so I was in full panic mode. The podcast still goes on. I still need promotional clips. I still have sponsors. I can't do this without a video editor. And so I was

stressed, but I did what I always do. And we found an amazing replacement who's just as good as my previous editor, if not more talented. And I do what I always do. I want to Indeed sponsor jobs to find my candidate. Indeed, sponsor jobs makes finding qualified candidate. it's so much easier because sponsored jobs boost your job post in the search results, helping you reach candidates who match the skills, certifications, or location that you're looking for. And if you're hiring too, you can join the 3.3 million employers worldwide that use Indeed to connect with quality talent that fits their needs. Spend less time searching and more time actually interviewing candidates who check all of your boxes. Less stress, less time, more results.

When you need the right person to cut through the chaos, this is a job for Indeed sponsored jobs. And listeners of this show, Young and Profiting, will get a 70, $25 sponsored job credit to help give your job the premium status it deserves at Indeed.com slash podcast. Just go to Indeed.com slash podcast right now and support a show by saying you heard about Indeed on this podcast. Indeed.com slash podcast, terms and conditions apply. Need a hiring hero?

This is a job for Indeed sponsored jobs. Gap fam, I am a perfectionist. I always want to make sure that I'm putting out the best offer possible to the world. So when I launched my LinkedIn masterclass and mastermind, I put a lot. poured my heart and soul into the content and I knew that this was going to be transformative for all of my students. But I didn't know how to launch a website. I didn't know how to handle payments. I didn't know how to launch a payment plan, a subscription. I didn't know how to answer their questions in the middle of the night when they're trying to check out. But I left at all to

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at shopfi.com slash profiting. That's shopify.com slash profiting. You say that you discovered regret has both a surface structure and a deep structure, right? So one is really easy to see, easy to describe, and the other one is not so so easy. So talk about that. Okay, perfect. You got it exactly right.

So we're looking at these regrets that are coming in from all over the world. I'm reading them one by one, trying to make sense of them. It's fascinating to hear people all over the world disclose a big regret. So let me give you an example. I mean, here's a weird one.

It's like from American college graduates, I am stunned by the number of regrets that American college graduates have about not studying abroad when they were in college. I couldn't believe it. Like even if you Google, not Google, but if you go into the database and search a phrase like study abroad, you get like hundreds of hits. I couldn't, it's crazy.

So, okay, so that's an education regret. Okay, people say, oh, I wish I'd studied abroad. I was a little bit too scared to go. go away and, you know, I thought I would miss people and da-da-da-da-da-da-da-da. And now I wish I had taken that. You know, now I wish I had studied abroad. I've heard that so many times, too, which is just so random that I've heard that. But you know what? It's a big deal, man. You know, I have to say, I was blown away by that. I actually think that there is a, and this is, you know, for the entrepreneurial Yap listeners out there. I think there's a business, a travel agency

serving basically 30-somethings and 40-somethings, 20-somethings, 30-somethings, 40-somethings, who wish they had studied abroad and didn't and now have a little money in their pocket. I really think there's a viable business in there. But that's an education regret. Okay, so then I have a lot of regrets. Okay, let's go back to entrepreneurship. I got lots of regrets, again, all over the world where basically say this. I really regret staying in this lackluster job.

I always wanted to start a business, but I never had the gumption to do it. Okay, that's a career. regret. Then I have, and this is again, volume, volume, volume, hundreds, and I'm not kidding around, hundreds, they basically go like this. X years ago, there was a man slash woman who I really liked. I wanted to ask him or her out on a date, but I was too chicken to do that. And now I've regretted it 10 years later, 20 years later, 30 years later, okay, that's a romance regret. So we got an education regret. We've got a career regret. We've got a romance regret. But here's the point I'm making in this little diatribe here.

Those are all the same regret. Those regrets on the surface, they're in different categories, but they're the same regret. You're at a juncture in your life and you have a choice. You can play it safe or you can take the chance. And overwhelmingly, when people don't take the chance, they regret it. And that's what I call a boldness regret. So on the surface, it's career is different from romance, is different from education. But one layer down, it's the same regret, if only I've taken the chance.

And what I found is that that is one of boldest regrets or one of four of these deep structure, core regrets that people all over the world seem to have. Yeah, and I feel like it makes sense to go through all four of them. And then I have some other questions about them. Okay, so we got the boldest regrets. One category of what I call foundation regrets. Foundation regrets are if only, because remember regrets, as you said earlier, regrets are if only's, all right?

So foundation regret is if only I done the work. If only I done the work. So these are regrets that people have. Okay, a lot of regrets about I spent too much and saved too little. And now I don't have enough money and now I'm broke. A surprising number of regrets about people who didn't work hard enough in school. If only I'd listen to my parents and worked harder in school, I'd have a little bit more of a stable footing in the job market. A lot of regrets about health in this way, too. If only I had eaten better. If only had

exercise, I wouldn't be out of shape and unhealthy today. So it's small decisions early in life that accumulate to really nasty consequences later in life. Again, these small decisions, like no single one is cataclysmic. It's like, oh, I ate, you know, I ate a whole bag of Cheetos once. That's like, people don't regret that. They regret eating unhealthily for a year, two years, five years, ten years. And it adds up. And it's hard to to undo. So foundation regrets, if only I'd done the work. Third category, we got boldness too. We got moral regrets. Moral regrets are, if only I'd done the right thing. Again, you're at a juncture. You can do the right thing. You can do the wrong thing. When we do the wrong thing,

most of us regret it. Because I think most of us are good and want to be good. And when we're not good, we feel crappy about it. And so these are regrets that people have about, oh my gosh, The two bigger ones here, marital infidelity. Woo! I had a lot of people, like, basically confessing on this world regret survey. It was like an online confessional. And then also a shocking number, shocking to me, number of people who regretted bullying other people when they were younger.

So bullying and marital infidelity, if only I'd done the right thing. Finally, fourth category, connection regrets. Connection regrets are about relationships and not only romantic relationships. and really not even mostly romantic relationships, just the full suite of relationships in our lives. And what happens is that you have a relationship that was intact or should have been intact with a parent, with a sibling,

with a relative, with friends, with colleagues. It was intact and it comes apart. Or should have been intact, was intact, and it comes apart. And I think what's interesting is that, again, if you read story after story, The way a lot of these relationships come apart is not dramatic at all. There's no big fight. There's no screaming or yelling.

It's just like this drift that takes place over time. And here's what happens. Somebody wants to reach out. They say, I was such good friends with Hala 10 years ago. I haven't talked to her for so long. Yeah, I should really reach out to her. And then I say, oh, man, no. But if I just reach out to her now, it's going to be so awkward because I haven't

talked to her for 10 years. It's going to be so awkward. I don't want to do that. And besides, she won't care. So I don't do anything. And then two years from now, I say, oh, man, I was such good friends with Holla 12 years ago. I really should reach out to her. But oh, my God, it's even more awkward now and she's going to care even less. And so we don't do anything and sometimes it's too late. And so, and that's a big mistake. Let me just double click on that for a moment. That's a huge mistake. We have piles of evidence showing that when people do reach out, it's way less awkward than they think, like way less awkward than we think we're completely over-indexed on awkwardness. My view in general in life, reading the research,

is that if you're feeling awkward about something, just freaking push through it. Don't let awkwardness, feelings of awkwardness be that barrier. Awkwardness is not a strong enough signal to stop you from doing something. Second thing is that we say people, but Halla's not going to care. people are almost always welcome it we're completely wrong on both fronts we're like it's going to be awkward and they're not going to care and when we do it it's not awkward and they always care so connection regrets are if only had reached out so let me quickly summarize those um we've got foundation regrets if only had done the work we've got boldness regrets if only had taken the chance we've got moral regrets if only had done the right thing and then we've got connection regrets if only had reached out

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Yeah. And, you know, if I remember correctly, connection requests are the most common regret. And I think especially in COVID, this is relevant. I think a lot of us, you know, weren't hanging out with our friends for a couple years. A lot of our friends moved away. I feel like this is your sign, guys. If you're thinking of an old friend that you haven't talked to in a while,

make sure you reach out to them, you know, don't have any regrets about that. So I'd love to hear about inaction and action and what we need to know about that in terms of regret. I'll give you a little bit of insight in how the sausage is made. So at one point, I had a chapter called, The rules of regret where I was going to say, unpack, here's how regret works. Like, we're basically pull up the hood. These are the rules of regret. This is how regret works.

Okay. And I's like, okay, should there be five rules or seven rules or whatever? And so I have this giant full, I'm fairly, I'm sort of a mix of like digital and analog. I still use a fair amount of paper because I prefer to read on paper. I use pencil and I, you know, do that kind of stuff. So I have this like these giant bulging folders of research. And I'm like, okay, I'm going to crack the. I'm going to figure out the rules of regret.

And I started going through the research and I'm like, oh, there's one rule. And the rule is there's a big difference between regrets of action and regrets of inaction. Everything comes back to that difference. And the architecture of regret, the difference between regrets of action, I regret what I did. And regrets of inaction, I regret what I didn't do is huge. All right. And here, there is a distinct difference in age. Okay. In my American regret project, which is the giant public opinion poll, I put together such a large sample in order to try to find demographic differences in what people regret it. So thinking that whites would have different regrets from people of color, people with lots of formal education would have different regrets from people with less education. Men would have different regrets from women. There were very few demographic differences. I was kind of shocked by that. But the one had to do with age, and it's this. People in their 20s,

tended to have equal numbers of regrets of action and inaction, equal numbers of regrets about what they did and regrets about what they didn't do. But by the time you hit basically your late 20s and certainly into your 30s and 40s and 40s and 50s and beyond, it's not even close. By the time you get literally to your late 20s, the inaction regrets take over. When you get to my age, okay, and I'm basically like double the age of somebody in their mid to late 20s,

When you get to my age, it's like three to one. Inaction regrets over action regrets. Unwemingly, over time, we regret what we didn't do. I regret that I didn't reach out. I regret that I didn't start that business. I regret that I didn't tell that person that I loved them. I regret that I didn't stand up to an injustice. That's what we regret, inaction over action as we get older.

And I'm curious to understand because you did all this research. you heard about so many different regrets. You really started to understand the science behind it and why we have regrets. What were some of the big life lessons that you learned about it that may not really be scientific or anything, but just life lessons that you're going to carry through? This is my philosophy now. Okay, so let's say you're at a juncture and you're wondering, ah, should I reach out to this person or should I not reach out to this person?

If you have arrived to that juncture, you have the answer to the question. Reach out. When in doubt, reach out. If you arrive at that juncture and you're wondering, the question is answered. Always reach out. I'm dead serious about that. There is, there is, I've seen too many, I've heard too many stories where it didn't happen and, and then something horrible arises and it ends up not being possible.

Somebody dies. I have so many stories like that. Always reach out. I'll give you another one. Andy, let's go back to inaction and action. I think that there's a lot to be said for, in general, having a slight bias for action. That is for, you know, so for just like for trying stuff. And again, it goes to the awkwardness.

So I think that awkwardness is a weak excuse, all right? I think fear is a stronger excuse. I think feelings of awkwardness. do what you can to push past those. Sort of a bias for action. I'm a happily married guy of 27 years, but I'll give everybody who's listening, all the Yap listeners, some romantic advice, okay?

Ask the person out. All right? I'm dead serious. If you're wondering whether he, she, or they, you should ask him, her, or them out. Do it. Do it. The worst thing that can have, happen is that the person says no. And you know what happens when the person says no? You're fine.

Life goes on. You're exactly where you were before you're asked. But here's the thing. Now you know. And you've taken your shot. So I think, you know, if there's one takeaway here is that ask the person out, just a slight bias, slight bias for action. Don't take awkwardness as a meaningful, as a meaningful signal. Always reach out. The other thing is, I'll give you one. I'll give you one more life lesson here, too, is that there's something to be said for, you know, when you're making a decision to consult your future self. So if you're stuck, you know, another thing to do would be, you know, call the you, you know, see if you can sort of send a text or make a phone call to the you of 10 years from now. So think about, think about, you know,

let's say that you're, let's say that you're 28 years old. All right. If you're at a juncture and you're saying, God, should I do this unethical thing or should I not? I guarantee you, Unless you're like, you know, 98% of us, 38-year-old you want you to do the right thing. So that's another, you know, if you're stuck, you know, think about what the you of 10 years from now wants you to want you to do. And the you of 10 years from now is really looking out for your best interest. And here's the thing. Well, the other thing is also we can make a pretty safe prediction about what the you of 10 years from now will care about. And it's not most things.

The me of 10 years from now isn't going to care what I have for dinner tonight. It isn't going to care what T-shirt I wore today. but it is going to care, did I do the work and build a stable foundation for myself, for my family, for my team? It is going to care of did I use my, you know, opportunity, this vanishingly short amount of time that I'm alive to like learn and grow and do something and contribute. It's going to care if I, 10 years or now, if I do the wrong thing, I have to confront the me of 2032 who's going to be wagging his finger at me saying, shame on you. Why did you do the wrong thing? and it's going to care if I don't reach out and build relationships of love and connection and

affinity and belonging. And again, it's not super complicated, but I think the cool thing is, is that this emotion that we often try to avoid is giving us this very, very clear window into what makes life worth living. Yeah. And I feel like for me, the big kind of takeaway that I'm getting from all this is having this bias for action. because like you said, the biggest regret is inaction. And we can't, most of the time, if we do something and we find out the answer, we're not looking back and saying, if only this, if only that, you just, that's what happened. And you just get over it and move on and you don't ruminate and think about it forever.

So speaking about ruminating, there's right ways and wrong ways to deal with regret. And dealing with regret is critical for us, like, moving in a positive way forward in our lives. So talk to us about the right way and the wrong way to deal with regret. The wrong way is pretty obvious. The wrong way is to simply ignore it. That's a totally bad idea, and it doesn't work over the long term. Another bad idea is to wallow in it, is to stew over it. And so the right way to do it is to try to avoid, especially that second path. And the way I look at this process is inward, outward forward, because the first step is to look inward. So let's say you have a regret or even more broad, you make a mistake.

The way, in the face of regrets, in the face of mistakes and screw ups, the way we talk to ourselves is incredibly harsh. Like, if you listen to, like, people's self-talk, it's brutal. You listen to my self-talk, you'd think I was a lunatic. You know, the way I talk to myself is just, is just cruel. I would never talk to anybody else that way.

And what the science tells us is, don't do that. There's very little evidence that that's effective in enhancing your performance. A better technique than self-laceration is what's called self-compassion, which is work pioneered by Kristen Neff at the University of Texas about 20 years ago.

And the principle is pretty simple. Treat yourself with kindness rather than contempt. Don't treat yourself better than anybody else. There's no evidence, oh, I should treat myself special. I should, you know, but don't, that's not true. But don't treat yourself worse than anybody else. treat yourself with kindness rather than contempt. Recognize that regrets are part of the human condition. Any app listener out there who has a regret, I'll find almost the identical regret in my database in 90 seconds.

It's part of the human condition. And you also think that I think is really important is that a regret is a moment in your life. It's not the full measure of your life. We sometimes will make these broad assessments of our entirety, based on a single thing in a single moment, and that's unhealthy. So that's inward. So you reframe inward. Second thing is outward. There's a strong argument to be made for disclosure.

Disclosure is a form of unburdening. It's not accidental that 21,000 people around the world told a complete stranger their big regret because I wanted to talk about it. It's just like what I was saying at the top of the show hall. It's like I mentioned my regrets very sheepishly and suddenly like this, you know, sort of uncorked this bottle where people want to talk about it.

And but the other thing I think is actually really important is that has to goes goes back to emotions and how we deal with emotions. Actions by their very nature are abstract. They're they're vaporous. They're blobby. That's what makes positive emotions feel good. But it's what makes negative emotions feel bad. And so when we talk about our negative emotions, when we, even when we, we don't have to

even tell anybody else. when you write about them privately, we take this abstraction and make it concrete, that we turn it from these blobby thing into concrete words, which are less menacing. And it helps us make the sense making, begin the sense making process.

It's inward, outward forward. And then the other thing that's really important, though, so we reframe inward, we express outward, but we also have to move forward. And the way we do that is we have to extract a lesson from that regret. And we tend to be pretty bad at solving our own problems. We're good at solving other people's problems.

Terrible at solving our own problems. So a really good technique is essentially to, it's what's called self-distencing. It's basically get some distance from yourself. So you can do things like talk to yourself in the second person. What should you do or even better, your third person? What should, you know, if yourself talk should be, what should Holly do? not what should I do, what should holly do.

I got to say the single best decision-making tool that I know of when you're stuck is to ask yourself, what would I tell my best friend to do? Whenever we do that, I have people come to me saying, Dan, I should you do this or should I do that? I'm just so torn. I don't know what to do. And I said, what would you tell your best friend to do? And they say, oh, well, I tell her, babbidi-bob-di-bib-ba-b.

And it's like, all right, you've kind of answered the question there. So for the business people in your audience, Andy Grobe, the former CEO of Intel has a brilliant, had a brilliant technique where he said he was when he was stuck on a business decision as an executive, he would say, okay, if I were replaced tomorrow, what would my successor do? And he always knew. And so again, so if we reframe inward, express outward, and then move forward by self-distance we begin to sort of develop that as a habit. And then we can then, you know, instead of trying to bat away this negative emotion or getting brought down by it, we basically, you know, hop on it at like a surfboard and ride it, ride it in to better health, higher productivity, more meaning in life and more

effectiveness, especially at work. Yeah. I'm curious, why is it so much easier to give advice to other people and to like kind of pretend that you're giving advice to your best friend? Like, why is it so hard to give advice to yourself? We're too caught up in the details of our life. At some level, we know too much, and that blinds us from the big picture. You know, it's like, it's like trying to understand, okay, I want to study the ocean. And what I'm going to do is I'm going to be, I'm going to scuba dive, all right, to try to understand the ocean. It's like, well, now I'm a memory. It's like, well, now I'm immersed in everything. If you really want to understand, like, what does the ocean look like? What are its boundaries? How's it configured? You want to be an oceanographer. You want to get up

like in a helicopter and go above there. And that's a better, often a better problem with solving technique. We just know too much about ourselves. We're too caught up in the gory details. Where with other people, we see, we see the big picture. We see what's really going on. We can bring those techniques to bear on our own problems, but we have to be deliberate and intentional about that. Even that thing that I suggested before about talking to yourself 10 years from now, that's a, that's a form of self distancing. Two takeaways from this, all right, for your listeners. One, ask them out. Two, if you're stuck on a decision, ask yourself, what would I tell my best friend to do? And then do that. Yeah, I think that's really good advice. And so regret is a very negative emotion.

People don't like to feel that way. Sometimes they wallow in their regret. And you talk about something called mental subtraction that can help us feel better in the moment when we're having a regret. Could you explain that to us? So I give you an education regret of mine, which is that I regret having gone to law school in general and probably gone to law school when I did. Okay. That's not a cataclysmic regret. It's not my biggest regret, but it's illustrative here.

Okay. But here's the thing. I met my wife in law school. So what I can do is I can say. well, let me mentally subtract that event. Imagine a word where I didn't go to law school. That's a world where I never would have met my wife. I don't want to live in that world.

All right. And so it's a way to find a silver lining, particularly in action regrets. And this goes back to this hidden architecture. With action regrets, we can find the silver lining. We can at least them. We can see a benefit in them, all right? which is why we can process them and make sense of them.

Some action regrets, we can also undo. So those people who I talk, all those people who have bullying regrets, more regrets, it's an action, I bullied somebody. Many of them go back 20 years later and apologize to the people they bullied. And so they're trying to undo that kind of regret. I have a guy in the book who has a no regrets tattoo, and he goes to get it removed. So with action regrets, we can mentally subtract certain positive elements of them.

We can at least them. We can undo them. And therefore, we can tamp down how much they bug us. That's why over time, action regrets recede and inaction regrets dominate. This is so interesting, Daniel. So let's wrap up the conversation. And I feel like a good way to round this out is to talk about the benefits of dealing with our regrets and the benefits of regrets in general. How can us, you know, doing what you just

mentioned, you know, self-distance, analyzing, trying to change our behaviors based on our regrets, how can that actually help us in life? On a number of different dimensions. Number one is that we know from these four regrets, if we know what people regret the most, we know what they value the most. So regrets are a negative, are like a reverse image of a life well-lived, of a good life. And what we know is what people want out of what people want out of life in general is, you know, foundation regrets are they want a degree of stability. A good life is not precarious. They want boldness is about the chance to learn and grow and do something and not like waste your time here and just do something.

Moral regrets are about goodness and connection regrets are ultimately about love. And so as you think through your, you know, your decisions, you can anticipate your future regrets. And the way to do that is to really maximize on things that, you know, if you're making a decision, it's like, is this going to build my foundation? Is this going to help me learn and grow? Is this the right thing to do? Is this going to help me build connections and affinity with people I care about?

Those kinds of things you should take, you should really like maximize on. But the other stuff, good enough is good enough. You know, like, I know we're not supposed to say good enough. is good enough, but good enough is good enough for a heck of a lot of things. So again, let's go back to Future You. Future You is not going to care this year whether you bought a blue car or a gray car. Future me, as I said earlier, is not going to care whether I wore that blue shirt today or I wore a yellow shirt today. There's so many decisions that we make that we don't even remember, we don't even care about. But there's some that stick with us. And we have a sense of the things

that matter most. And so if we really focus our efforts on our attention on these kinds of things, on building a solid foundation, on learning and growing, on being good and moral and truthful and doing the right thing, and on building relationships of, you know, love and belonging, I think that regret gives us this path to do things better. I give you one other tip here that I think is useful because it's, again, less, less abstract and more. One of the most useful things to do is to do what I did a couple of years ago, which is that push past the awkwardness. And if you have a team that you work with or a group of friends, tell people about one regret that you have. Tell them what you learned from it. Tell them what

you're going to do about it. And I can almost guarantee that you will have one of the richest, most interesting conversations you've had this year because I was wrong. I thought nobody wanted to talk about regret. And I discovered, as I said, at the very beginning of our conversation, that everybody wants to talk about regret. Because as you said, it's normal, it's universal. It's part of the human being. Yeah. And Young and Profiters, I loved his book, The Power of Regret. So make sure you guys go get that. There's lots of exercises that you can do to understand what your regrets are, how to deal with them. So I highly recommend that. I'll put that in the show notes. Daniel, I always ask the same two questions at the end of the show

for all of our guests. Then we do something fun at the end of the the year. So the first one is, what is one actionable thing that our young improfitors can do today to become more profiting tomorrow? Listen more and talk less. I feel like so much of the work that we do obviously involves groups and other people. And most of us are not very good listeners. We don't actually work hard at listening. No one has ever taught us how to listen. You know, when we're in elementary school, they teach us how to read and that, you know, they teach us how to write. but no one ever teaches how to listen. They think because we have ears, we know how to listen.

And most of us are not very good listeners. And so one way to listen better is to talk less and listen more. I love that. And what is your secret to profiting in life? And profiting does not need to be related to finances. It's going to sound strange, but I think it's to be generous to help other people, to use a Boy Scout thing, to leave the campsite better than, then you found it. I really think that that is the way to live a good life. It allows you to

profit in all senses of the word. I think it has a professional benefit over time, certainly not in the short term. Over time, it has a professional benefit. But more than anything else, it allows you to look at your life on a day, on a week, and say, I did something. I contributed. I made the world a little bit better. I love that. And where can our listeners go learn more about you and everything that you do. You can go to my website, which is danielpink.com, d-a-n-n-e-l-p-I-N-K.com. I've got a free newsletter. I've got free resources. I got all kinds of groovy stuff. Amazing. We're going to link all that in the show notes. Dan, thank you again for coming on Young and Profiting Podcast. Always a pleasure.