Leap Academy with Ilana Golan - The Power of Regret: Daniel Pink on The Unexpected Tool to Unlock Your Greatest Success | E101

Episode Date: May 1, 2025

After studying law, Daniel Pink transitioned into politics, serving as the chief speechwriter for Vice President Al Gore. However, he soon felt unfulfilled and realized his true calling wasn’t in a structured career with defined rules, but in writing. Despite the uncertainty, he made the leap, leaving politics behind to pursue writing full-time. This decision led to multiple bestselling books, including his latest, The Power of Regret. In this episode, Daniel joins Ilana to discuss how embracing regret, rather than avoiding it, leads to profound growth and how we can turn our past decisions into catalysts for a better future. Daniel Pink is a bestselling author and speaker known for his work on business, work, and human behavior. His books have been translated into 46 languages and have sold millions of copies worldwide. In this episode, Ilana and Daniel will discuss: (00:00) Introduction  (01:51) Growing Up with a Love for Books (06:13) Transitioning from Law School to Politics (09:49) Becoming a Speechwriter for Vice President Al Gore (12:24) Why He Chose a Career in Writing Over Politics (16:07) From Struggling Writer to Bestselling Author (18:06) Uncovering the Key to Human Motivation (21:55) The Science of Timing and the Midpoint Slump (26:43) Embracing Regret as a Catalyst for Growth (30:21) The Four Types of Regret and Their Impact (34:59) Turning Regret Into Action and Growth (40:08) Daniel’s Motivation for Writing Books (42:04) The Power of Ignoring What Others Think Daniel Pink is a bestselling author and speaker known for his work on business, work, and human behavior. Before becoming a full-time author, he held several positions in politics and government, including serving as the chief speechwriter for Vice President Al Gore. Daniel has since written seven New York Times bestsellers, including Drive, When, and his latest, The Power of Regret. His books have been translated into 46 languages and have sold millions of copies worldwide. Connect with Daniel: Daniel’s Website: danpink.com  Daniel’s LinkedIn: linkedin.com/in/danielpink  Resources Mentioned: Daniel’s Book, The Power of Regret: How Looking Backward Moves Us Forward: https://www.amazon.com/Power-Regret-Looking-Backward-Forward/dp/B098VRLZ2H  Daniel’s Book, A Whole New Mind: Why Right-Brainers Will Rule the Future: https://www.amazon.com/Whole-New-Mind-Right-Brainers-Future/dp/1594481717 Daniel’s Book, When: The Scientific Secrets of Perfect Timing: https://www.amazon.com/When-Scientific-Secrets-Perfect-Timing/dp/B076MBR89W Daniel’s Book, Drive: The Surprising Truth About What Motivates Us: https://www.amazon.com/Drive-Surprising-Truth-About-Motivates/dp/B0032COUMC Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Wow, this show is going to be incredible. So buckle up and I'm sure you're going to enjoy it. But before we get started, I want to ask you for a favor. See, it's really, really important for me to help millions of people elevate their career, fast-track to leadership, land dream roles, jump to entrepreneurship or create portfolio careers. And this podcast is all about enabling this for millions of people to see a map of what it actually takes for big leaders to reach success.

So subscribe and download so you never miss it. Plus, it really, really helps me continue to bring amazing guests. Okay? So let's dive in. Everybody has regrets. It's one of the most common emotions that people have. Give me any regret that any of your listeners have. I'll find it in 15 seconds in the database.

Daniel Pink is the author of five New York Times bestsellers, including the latest, The Power of Regret. Daniel's books have won multiple awards, have been translated to 46 languages, and have sold millions of copies around the world. If you hit age 50, you likely have more of your life behind you than you have ahead of you. We have this database now of

26,000 regrets from people in 134 countries. These four regrets are incredibly common around the world. There are foundation regrets, which are decisions that people make, they're not devastating upfront, but that accumulate to bad consequences. There's regrets of butt-boldness, there's moral regret, and then there are, in the architecture of regret,

there can be two kinds of regrets. There are regrets of action and regrets of inaction. As we age, there are more inaction regrets than action regrets. So once you find that regret, what do you do? First of all, treat yourself with kindness. Number two. Okay, today we have a really special episode and you'll see why Daniel Pink is the author of five New York Times bestsellers, including the latest The Power of Regret.

Daniel's books have won multiple awards, have been translated to 46 languages, oh my god, and have sold millions of copies around the world. Daniel's books are exactly what you, Leapers, need to hear. And that's incredible because if you're looking to reinvent yourself or reinvent your reputation or your career and take yourself to the next level, that is exactly what the books are about. So let's dive in. Daniel, I'm so excited to have you. I'm so glad to be here, Alana. Thanks for having me. Amazing. So I am going to take you back in time. I want to hear a little bit of Daniel the Kid. What sparked that love for writing, for books? What planted that seed?

Well, I think the love of books preceded the love of writing. When I was growing up, I didn't say, oh, I want to grow up and be a writer. I don't think that was my main goal. A lot of life, as all of us know, is about circumstance. When I was six, early in first grade, my father got a new job and we moved from Wilmington, Delaware,

where I was born, to Columbus, Ohio, where I grew up. It just so happens that Ohio in general and Central Ohio, in particular, have an amazing public library system. As a consequence, I grew up a short walk away from an excellent local public library, and a very easy bus ride away from a massive and majestic Carnegie funded, massive public library.

Both my parents were readers as a kid, I went to the library a lot, not because I had to, not because somebody is forcing me, because it was good, I liked it. Also, truly in the summer, the library had air conditioning and my house did not have air conditioning. And it was cooler in there. And so I grew up going to the library a lot. And as a consequence, I grew up reading a lot. And being a reader was actually a big part of who I was as a kid.

And I think that had I not grown up in a place where I had such immediate access to fantastic public libraries, I don't think I would be a writer today. I really don't. I think I would have done something else. Interesting why they have such a beautiful library system. I don't want to have all your listeners completely click out of here. It has to do with the unique way that Ohio, unlike other states, funds public libraries.

Ohio is essentially a dedicated fund for public libraries, which means that the Ohio libraries are among the best in the country. Incredible. I did not know that. But then you actually went to something very, very different, a study in college. You graduated in North Carolina University in linguistics and then you went to Yale Law School. First of all, why law? But I think at really early age, you realize that this is not it, right? This

is not the thing. So tell us a little bit. So just to take a step back, when I was maybe like nine or 10, what I really wanted to do, I did have a career aspiration. I mean, my original career aspiration was to play both Major League Baseball and the NBA. By the time I was 10, it seemed like that dream was not going to come true. The other thing that I would do when I was much younger is, when I was actually in elementary school and even in junior high,

what we now call middle school, I was actually in a lot of plays and actually wrote a lot of plays, curiously enough. When I was maybe like 10 or 11 or 12, you had asked me what I wanted to do. I would say, I think I want to write and direct movies. But then I abandoned that. Not kind of, I did abandon that in part

because I was also pretty good in school, because school was actually really easy. When I went to school, basically, all you had to do was be compliant and give the authority figure what they wanted on time neatly, and you were suddenly, quote, a good student. So for whatever bizarre reasons of personality and insecurity,

I was a good student and the good students typically didn't participate in the arts. Those are two different worlds. So I went that way and I was a good student and the good students typically didn't participate in the arts. Those are two different worlds. So I went that way and I was a good student because it was so easy because the system was so stupid. So I went to college and college is different because college I can actually learn something and pursue what I wanted to pursue. And I ended up pursuing linguistics just because I was sort of the perfect combination for

me and that it was obviously about language. I would simultaneously be in classes with linguistics classes literally like from one to another with computer science majors, the early computer science majors. There's certain kinds of syntactical courses in linguistics that are also the core of computer science. And then I would also be in classes with poetry students because there was other aspects of linguistics that were very literary. And so the combination of sort of the math and the literary was fantastic for me. I loved it. And then I went to law school largely because I grew up in Columbus, Ohio, and I was a middle

class kid who went to college on financial aid and was concerned that I needed to make a living. And that was the way to do it. And I didn't want to be a doctor and I didn't want to be an engineer. That was my life. I had three choices. It was two and then engineering came. want to be a doctor and I didn't want to be an engineer. That was my life. I had three choices. It was two and then engineering came. I could be a doctor or a lawyer or then if you know. It's a very common pattern among American middle class people, zero to one generations removed from coming to this country without any money or you know anybody who wants to try to get a stronger foothold into the middle class.

I did that and I was also deeply interested in politics at the time. I went to law school and once I figured out what lawyers did, I was like, I'm not doing this. It's too boring. I was like, I'm not doing this. Even if it makes a lot of money, I'm not going to do this. I happened to be fortunate in that my law school had

a program where if you went to work upon graduation and you earned below a certain salary, no matter what you did, they would help subsidize the repayment of your student loans. Again, circumstantial. But for that, I maybe would have gone to practice law to pay off my student loans. But that allowed me not to do that. So I started working on political campaigns

because that's actually what I was deeply interested in doing. That took me to some early work in politics. Before that, what sparked that love for politics? Was there a specific moment? I don't know. That's a good question. Part of it is that it was exciting. I was a big sports fan, so it's like sports. It was about something that mattered. It was a big sports fan, so it sort of liked sports.

It was about something that mattered. You know, it was about how we're gonna run things, and so the stakes were high. I thought that the issues were pretty substantive, so I found politics super, super interesting when I was probably starting in high school. So all throughout college. Yeah, but I didn't major in political science

or anything like that. I just, I was deeply interested in politics, and I felt that it was substantively interesting and also important because there were things happening then that I thought were messed up and I didn't want them to happen. Right. I won't talk about today.

But yes, but was there like a specific moment in practicing law or starting to understand that this is gonna be your life? Was there a specific moment that practicing law or starting to understand that this is going to be your life, was there a specific moment that you said, okay, this is not going to be my future? Is there something specific? You know, I'm a writer and I like to craft a narrative around big moments. And I think that makes for a good story. It's just not the reality of my life. I haven't had any like epiphanies or big moments or come to Jesus encounters.

It's usually these things, they're slower. It's more like a crock pot rather than a microwave. Right, but you're basically seeing what you're gonna need to do as an intern or whatever, and you're like, this is just not gonna be it in law school. Oh God, no, I mean, yeah, no, I would go to work for a law firm in the summer to make some money. And I was like, oh my God, this is so boring.

Who would want to do this? That was not like some kind of traumatic wrestling. That was just like, oh man, if I was smarter, a little less risk averse when I was younger, I probably would have waited to go to law school and might not have gone at all. If I was one of those people who had gone to law school when they were 30 or something like that, first of all, I might not have gone. If I had waited, and might not have gone at all. If I was one of those people who had gone to law school when they were 30 or something like that,

first of all, I might not have gone. If I had waited, I might not have gone, which could be a great decision. And if I had gone, I think I would have gotten a lot more out of it and enjoyed it a lot more if I had waited. But the idea of going when you're that young and you don't know anything and you're just kind of

a cork bobbing along on the surface of the ocean. I love that metaphor. So you decide to go to politics and somehow you land a dream opportunity to be speechwriter for Vice President El Gore. Like how the heck did that happen, Daniel? It happens in a nonlinear half-assed kind of way, as many things do. One of the things about politics, which I really like, the mechanics of politics, is that things move fast and it's not entirely, but it's kind of a meritocracy internally, especially in campaigns because

there's winners and losers. And it's also very low paid. So the people in it tend to be younger than you would ever expect. And so I went in younger than I would doing things at an age that I would never have expected. And basically I became a speechwriter because at some point, I don't even remember when I don't even remember this as a moment, somebody turned to me and said, can you write a speech? And one of the things that I intuited, but which I now specifically instruct my own kids and others is that when somebody asks you that question, the answer is yes, whether you can do it or not.

The answer is yes. And then you freaking figure it out. So I was at intuitive sense that the answer to that question, the answer is yes. Whether you can do it or not, the answer is yes and then you freaking figure it out. I was at intuitive sense that the answer to that question should be yes. I said yes and I wrote a speech. It was probably okay. Then they said, can you do it again? I was like, yeah. Can you do it again? Yeah. Suddenly, that was my job.

Because again, it's low-paid and fast movie. I started doing that and then there aren't that many people who write speeches. And so when there's turnover, there's a limited supply of people who are eligible for that kind of job. And it turned out that was actually, I mean, again, I don't want to toot my own horn here,

even though I'm about to. It's like, I was actually a pretty good speechwriter. Like I was pretty good at it. I'm sure you were. I'm not bullshitting. I was actually pretty good at it. You know, I was, to my surprise, like it wasn't something I set out to do,

but it's like, oh, I get this. I think that's another lesson for leapers out there is that there are certain things that we are good at and certain things that we're not. You can get better at almost anything, but there are certain things that feel like a native language in a way.

There are other kinds of things that for me, I could learn how to do it, but I would do it in a clumsy way. And it just turned out that speed writing was something that I sort of had a feel for in the way that some people have a feel for physics, which I do not, or some people have a feel for tennis, which I do not. I agree a thousand percent.

We call it the zone of genius. And I think it's exactly it. Like somehow that power of words, storytelling, persuasion, impact that creates somehow that gelled with you. And it almost looks like all those pieces, like the linguistics, the libraries, like everything came together to create that magic, essentially.

So you're writing these speeches, but at some point you decide that politics is not your thing. It's not gonna be the thing. It's not going to be the thing. Tell us a little bit about that time. Basically what happened was this, is that I really liked the people I worked with and I was very fortunate, especially later in when I was working in politics,

to work for big bosses who were good. I worked for the then Labor Secretary Robert Reich, I worked for Vice President Gore. Those are two good guys, and those are two good people to work for. That was not it at all. Actually, my colleagues were outstanding. I really liked my colleagues.

What I didn't like were some other things. Number one was that I did get a sense that politics, this is a long time ago now, that it was all about tactical short-term advantage. It's like a doctor who goes in and says, I became a doctor to take care of people and she spends all of her life dealing with like electronic medical records

and insurance paperwork, you know what I mean? It was sort of analogous to that. It's like, oh my gosh, all we're doing here is we're seeing about this far out. We're seeing one new cycle out and there isn't really a great strategy or vision because of the nature of the system. So that was one thing that really was kind of discouraging.

The second thing that was discouraging, not discouraging, but the second thing was sort of a discovering about oneself is that I don't like having a boss. My bosses were okay. They were not like, they were good people. I didn't have any, you know, generally, but it's like, I don't want someone telling me what I was gonna work on

and what I was not gonna work on. I don't wanna do telling me what I was going to work on and what I was not going to work on. I don't want to do that. Another thing is that I had, especially true because when I was working for the VP, my wife and I had our first kid and that changed my life. And so it's like, wait a second, I'm like killing myself for this short term thing and not having any autonomy. And I don't get to see my little girl, I don't like this. And then even worse is that I would look sort of prospectively and say, what is the me 10 years from now going to do if he stays on this trajectory? And I was like, oh my God, I don't want to do that. That was in some ways a come to Jesus moment. And I quit. Now, again, it's not, I don't want

to sound like too much of a renegade because my wife kept her job, she kept her health insurance. We had a plan because I wasn't bringing in that much money. We had a plan and the plan was that we'll try it for, I wanted to go out and do my own writing, and we'll go out and try it for a couple of years and see if it works. If it didn't work, I'd go back and get a job. But she's not giving up her job, she's not giving up her health insurance.

If there's a superpower that I have, it is frugality, so I don't spend a lot of money. We just stumbled our way into figuring out how to make it work. Incredible. Was it scary, Daniel? Do you remember? I didn't actually find it very scary. I should have probably. I made me because I was clueless. Here's the thing, Alana, I'm not joking about this.

When I went to work for myself, basically leaving a job and then going to work in the attic of our house, I had a negative net worth. Now the good news is that at the time, I don't think I knew what a net worth was. I didn't know that, all right? I just know retrospectively, it's like, holy crap, you did this with a negative net worth?

Because I owed more than I was worth. And I did, it actually didn't feel especially scary, honestly. Well, sometimes when we're young, we do these things and we don't even realize that it should have been scary. Or maybe sometimes we don't even realize how hard it's going to be. That's a different thing. That is, discovering that something is harder than you

expect is a reality. And I think I definitely did encounter that. But being frightened beforehand wasn't a big thing in part because I planned it out You know and it basically I looked at it very very rationally again. We still had an income coming in We still had health insurance. We were not big spenders and Also, there was a plan B in the sense that I knew I could always go find another job I was not worried that I was gonna be unemployable So take me there for a second. So a book takes time.

God, I'm still, you know, I'm just now finishing my first, so I have so much respect. Meanwhile, like, is there like a nagging like, oh my God, should I get a regular job? Or is it just a passion? Because I think you came with the free agent nation in 2001. And then, you know, a whole new mind in 2004, and I might not be completely accurate, but that's kind of right. But is there like, oh my God, can I do this? Any dilemmas or no? You're like, oh my God, I'm living a dream. It's neither one of those.

It's neither dark nights of the soul where I'm wondering whether I can do this, nor is it this kind of blissful thing. It's neither one of those. I have a job to do, I have something I care about, so get to work and then do it the next day. Do it the next day. I didn't spend a lot of time on either of those polls because I didn't spend a lot of time pondering it.

I just was doing shit. So that's what it was for me. Now, again, just to be very clear about this, when I first started out, I couldn't make enough money as a writer. And so I actually took on some corporate speech writing, which I hated, but paid for diapers. That was a side gig for about a year or so

until I found my footing as a writer and then also managed to get a book deal that paid in advance that covered us partially, kind of, sorta. I was in my early 30s. We had one baby, then we had another baby. I'm working for myself. My wife is litigating on behalf of the United States Department of Justice.

You're just trying to get through each day. You know? I mean it. I mean, you're just not thinking about, oh my God, is this a source of meaning? Oh my God, I'm living the dream. Oh my God, I'm so scared. You're saying, what is the mess in front of me

that I need professionally or personally that I need to clean up right now? That is very true. Okay, so then at some point, you're starting to research your writing for Drive and you uncover really what motivates people, right? And that becomes this game changer. First of all, did you realize that it's going to become a game changer

or was it just something that you were passionate about and you understood that sticks and carrots and you have a beautiful TED Talk about it, but this is not the right way to do it? At that point, so I wrote Free Aging Nation and so I got that out of me. I wrote a book and I learned how to write a book. That's really important.

I showed myself and I showed the world that I can do this. Then I wrote A Whole New Mind. And A Whole New Mind did very well commercially, knock wood. I mean, I always believe the wolf is at the door, but that mitigated that fear for a little bit. And then I wrote a graphic novel in 2007. I got a fellowship because our kids were little.

They were very portable. And I said, let's go to Japan. We got a fellowship to go to Japan and I studied the manga industry, the comic industry because I was very interested in that. Then came back and wrote this graphic novel career guide, which was a hoot. Then after a whole new mind, I got a lot of questions from readers about if you're right that we're moving from a world that prizes logical linear skills to one that prizes artistic empathic skills and how do

you lead people, how do you motivate people to do it. I didn't know the answer to that. I started looking at the research and the research said some things that were shocking to me about the limits of some of these if-then rewards and about how rewards can sometimes backfire and how there are other things that actually lead to sustained enduring high performance. I thought it was fascinating. It is fascinating. As you know from writing a book yourself, it's a giant pain in the ass to write a book.

You have to pick something that you're genuinely interested in. I was genuinely interested in this and I wanted to figure it out, and that's what I did. So I wrote that book. Again, the goal is to, for me at least until recently, is as I think about making a different kind of leap myself, the goal is in writing books is to be able to write another one. That's the main goal. That's what was firing me on that one.

And that becomes this kind of a phenomenal people are coming to you and saying how it's reshaped organizations. And your TED Talk is one of the most, I don't know, seen talks of all times or whatever, with many, many millions of views. Why do you think it resonated so much? And did you realize that it's gonna make such a big impact? I think that it resonated because it gave language

and relatively simple and straightforward language and an explanation to a phenomenon that people felt intuitively. They had a sense, they knew deep down that they were not motivated only by carrots and sticks and they had a sense that a system constructed so heavily on that was somehow off, but they didn't have the language quite to describe it. And so I think it was a combination of giving people language to describe these inchoate feelings and also giving evidence for this claim that shouldn't be counterintuitive, but that is.

And I think that's part of why your TED talk also did so well, right? Because it was so simple to follow. And on the other hand, it's like, how did we get it all wrong, right? Because our instinct is always like, let's give you accolades and pay for it, but that's actually not what motivates people, which I found fascinating as well. Right, right, right.

I mean, rewards do motivate people. It's just that, and if you're in an organization, you wanna pay people really well, but the idea that you're gonna get better performance by dangling a high stakes reward in front of somebody all the time is just not true. And sometimes it actually kills creativity. Yeah, sometimes it hurts.

If you're feeling stuck, underpaid or unappreciated, or you're simply ready to take your career and life to the next level, I have the perfect solution for you. We have a program that helps you fast track and leap your reputation and career. Become the best version of yourself. Get the dream role you deserve, move up to leadership, jump to entrepreneurship, or even build a portfolio career. This program helps hundreds a year, and it will help you gain the income, influence, and impact that will transform the second part of your life. Watch our free training today at leapacademy.com slash free hyphen training. The link is in the show notes.

Now back to the show. One question about your book, when for my audience this is really relevant because you're exploring basically the science of timing. You keep looking for different topics. I love that. Like it's so fascinating. And this book is more about timing. And sometimes the timing of a day is sometimes the timing to other projects.

And you elaborate really beautifully there. But one thing I do want to talk about is the tricky middle. I think this is really, really interesting because everybody will deal with midpoint slumps. How do you motivate yourself when you really feel like, you know what, that's it, I'm done? And sometimes these are really, really hard. I think a lot of people are talking about the start, but not necessarily the hard middle. And I love that you did that. So talk to me a little bit about that book and also how do you recover through these

midpoints? So, I mean, I had another book that came out before that called To Sell As Human. That was basically about the science of selling because I was interested in that. Then after that, I said, I'll just give you the genesis of the book When. It was again like the genesis of the other stuff, it's just something that I was curious about.

I realized in writing before I wrote that book that I was making all kinds of decisions about timing in a given day, like when do I start my work? When do I quit for the day? When do I start a project? What do I do in the middle of a project when I'm not sure it's going to work? Do I quit? Do I go forward? How do I summon the motivation to do

something when I'm in that messy middle, as you say? I was making all these questions about timing and I was doing it in a completely blind, intuitive, half-assed way. I said, someone's written a book about this. I started looking around for the book and no one had written a book about it. I was like, oh man, you know what? I need to read this book and the only way I can read this book is if I write this book. What I did is I looked at

a very large number of studies on timing, asking these timing questions. The thing about these timing questions is that they were spread across many, many, many disciplines. They were in psychology, they were in economics, but they were also in neuroscience, they were in anesthesiology, but they were also often asking very similar questions.

How did our behavior and our mood change over the course of a day? How do breaks affect us? How do beginnings affect us? How do midpoints affect us? How do endings affect us? How do people synchronize? And so I wrote that book largely so I could read it because I was interested in it. us, how do beginnings affect us, how do midpoints affect us, how do endings affect us, how do people synchronize?

So I wrote that book largely so I could read it because I was interested in it. So on your question of midpoints, yeah, one of the things is that our lives are episodic in a way. So much of what we do has a beginning, a middle, and an end. This interview has a beginning,

a middle, and an end. Any kind of project has a beginning, a middle, and an end. Those kind of project has a beginning, a middle, and an end. And those episodic moments change us in a way. And so for midpoints, midpoints can drag us down. There's no question about it. There can be kind of a droop at the midpoint. We saw that until recently,

a sort of a U-shaped curve of wellbeing over time, where people in the middle of their lives were the most unhappy. Some of that data has changed recently, not because people in the middle have gotten happier, but because people who are younger have gotten way less happy. That's sad. No, I mean it. That's a sad research.

So instead of it looking like a you, it looks like just a decline. Everybody's unhappy until you get old. Let me answer the question you actually asked, which is, what do you do at midpoint? So there are a few things that you can do. I think there's some pretty good research showing that the way you frame it can be really important. And I use it sometimes for running. Let's say I'm going to go run five miles.

During the first two and a half miles until you get to the midpoint, you motivate yourself better by thinking about how far you've come. So, oh my gosh, I've already gone a mile, I've already gone two miles. And then when you're past the midpoint, you actually get more motivation by imagining how little you have to go.

That can be really useful. Another thing that you can do in the midpoint is actually create a set of smaller shorter moments. And so what you can do is you can say, let's say you're writing a book and you're not sure exactly what the midpoint is. Basically say, what I wanna do is I wanna get to the end of this section. I wanna get to the end of this chapter.

And that can give you the motivation, even if you're not at the end of the book itself. So slicing into smaller things. There's some interesting research from the NBA. Now about the NBA, done by Jonah Berger and Devin Pope, showing that teams that are ahead at halftime in the NBA are more likely to win the game, not surprisingly, but teams that are behind by one are actually behind by one are actually more likely to win the teams that are ahead by one because and there's other experimental evidence showing that if you feel like you're

slightly behind in the middle, you get some extra motivation. So if you feel like you're way behind, you give up. If you feel like you're way ahead, you can become complacent. But if you just feel like you're a little bit behind, and so having that thin edge of hunger and feeling a little bit behind in the middle can be helpful. So let's go to your recent book, The Power of Regret. I think you're normalizing regret is really interesting thing. And I love how you're talking about looking backwards takes us forward. We see a lot of regret in these people when they're trying to recap their career and trying to think where they made different decisions. Can you talk a little bit about that, Daniel?

And what made you, what made you even start this kind of a book? I had regrets. I mean, it's that simple. It's very therapeutic for me, Elana, to sort you even start this kind of a book? I had regrets. I mean, it's that simple. It's very therapeutic for me, Ilana, to sort of talk about how all of this evolved. But this is not a book that I would have written in my thirties. I would not have written a book about regret in my thirties, but in my fifties, it felt in some ways inevitable because, you know, if you hit age 50, you likely have more of your life behind you than you had of you. And so I had a lot of room to look back and I look back as people do and when I look back there were things

I wish I had done there were things I wish I hadn't done there were things I wish I had done differently and I was curious about that. Is there something specific that comes to mind when you think about it? Here there was a catalyst in that I really started thinking about this deeply at my elder daughter's college graduation because that kind of marker is very meaningful because I'm in this graduation ceremony and I see this kid, not a kid, this young woman and- How did that happen? Exactly.

Precisely the question I asked, how the hell did that happen? Like this kid used to be like an infant. This is the same kid we're talking about being born and then they're writing for Asian nation. It's like crawling up the stairs of my attic office. Suddenly she's walking across the stage in a college graduation.

I blinked and that happened. That's disorienting. Then also it's like, how can I have a kid? How can I have a daughter who's 22 years old when I'm like 25 myself? I started thinking about in particular, about my own college experience, which was generally quite positive, but I had some regrets about that.

When I came back home to Washington DC where I live, this is a moment where I was thinking a lot about regret. I realized, it's like, oh my God, I don't want to talk about this with anybody because nobody wants to talk about regret. I sheepishly mentioned my regrets to a few people, and I discovered that everybody wanted to talk about it. That once I brought up regrets,

it just uncorked this need that other people had. That's very interesting reaction when you're a writer. I decided that I would actually throw away a book that I was working on, and then wrote an entirely new proposal for a book about regret. This is the closest thing I have to a moment where I was going one way and I reached that moment and then went the other way.

Do you feel there's a difference between little regrets that you can just look back and learn from versus the scary regret of getting to the end of your life and having massive regret over your life? Like, is there a difference? I mean, I think so. There are differences among regrets on a number of different dimensions.

I do think that what you're talking about there is a difference between sort of retrospective regrets and prospective regrets. So, you know, if you look retrospectively, you shouldn't regret every mistake that you made. You'll drive yourself crazy. And I think one of the discoveries is that a lot of the decisions we make

don't really matter all that much. And then there's certain kinds of regrets that people have that are not massive, that are made, you'll drive yourself crazy. And I think one of the discoveries is that a lot of the decisions we make don't really matter all that much. And then there's certain kinds of regrets that people have that are not massive, that are small, they can make peace with them, and they don't really bug people. When you're thinking about the end of your life and getting there without deep regrets, I think that's a different kind of reasoning.

And I think it can be healthy, but it has to be done in the right way. So it depends on whether you look backward. If you're looking backward and scrutinizing your choices of what you did or didn't do, that's one thing. If you're going, if you're looking forward and trying to avoid future regrets, that's something else.

And you do talk about foundation, boldness, moral connection. Can you elaborate just a little bit? Because you're right, there's such different types of regrets. Let me just show my work just a little bit because you're right there's such different types of regrets. Let me just show my work here a little bit. So to write this book what I did was I looked at there's a lot of good research on regret in multidisciplinary research again a lot of it in social psychology actually started out in almost like political science, political economy,

national security studies. There's a lot in economics. There's a lot now in psychology and social psychology, but there's also a lot in neuroscience and cognitive science. So looked at what is 50 years of research tell us about this emotion of regret. Then I also did a very large quantitative survey, basically a very large public opinion poll, the largest public opinion poll ever. Well, I did two things. I did a quantitative poll of the largest public opinion survey ever conducted of American

attitudes about regret. And then I collected regrets from around the world. And that proved to be really revelatory because we have a database now of 26,000 regrets from people in 134 countries. And what it says, to answer your question again, in my typically roundabout way, is that yes, indeed, Elana, there are, we did find that around the world, there are four types of regret.

There are foundation regrets, which are decisions that people make, smallish decisions that people make early in life that accumulate. They're not devastating upfront, but that accumulate to bad consequences. I spent too much and saved too little, now I'm broke. There's regrets about boldness, which is a very big category where you are at a moment in your life and you say you could play it safe or take the chance. And overwhelmingly people

who don't take the chance regret it. Not always, but overwhelmingly there's moral regrets, which are if only I'd done the right thing. So once again, you have a choice. I can take the high road, I can take the low road, I can do the right thing, I can do the wrong thing overwhelmingly. Again, not all the time, but people regret taking the low road, doing the wrong thing, it sticks with them. And then finally, their regrets of connection, which are, if only I'd reached out. And these are regrets about relationships that come apart, and you want to do something, but you're too scared to do something and your forecasting is off about how other people are going to respond. And so these four regrets

are incredibly common around the world. I mean, the listeners will have all sorts of regrets, right? But I think that I made the wrong choices. I put myself in an industry that I can't remove myself from. I jumped into entrepreneurship and now I'm broke. It's interesting even, you know, if I look at it from the lens of Leap Academy is how many people have small regrets or big regrets around decisions that they made or lack of decision. I think this is also something beautiful that you say in the book. Actually, lack of decision almost is more

common than making a decision. Well, what we know from my quantitative research and what we also know from other research is exactly that distinction. So again, forgive me for getting in the weeds here, but I did something called the World Regret Survey, which was basically a giant collection of regrets from all over the world. That's what we were just talking about.

That's a qualitative piece of research. I also did a pretty sophisticated public opinion survey of a sample of about 4,400 Americans, asking them a set of questions that you might get from Polster about attitudes to regret. That's a very large sample, 4,400, for this kind of research. And the reason that the sample is so large is that my main goal was to look for demographic differences in regret. So do women have different regrets than men? Do people with lots of formal education have different regrets than people with less formal education? I found very few demographic

differences except for one and that had to do with what you're talking about here. So in the architecture of regret there can be two kinds of regrets. There are regrets of action, I regret something I did, regrets of inaction, I regret something I didn't do, action inaction. People in their 20s had equal numbers of regrets of action and inaction. But as people age, in their 30s, there are more inaction regrets than action regrets. In 40s, even more inaction. By the time you get to your 40s, 50s, 60s, 70s, it's overwhelming. Overwhelmingly, as we age, there are more inaction regrets than action regrets. There is zero, I mean, I don't want to think about this as like akin to the law of gravity, but in the world of social science,

this is as close to a unshakable truth as you could possibly have, which is that over time, people are much more likely to regret their inactions over their actions. It's not even close. Inaction regrets are what stick with us. And it could be anything. It could be anything.

Yeah, if only I'd started a business, if only I'd asked that person out on. Yeah, if only I'd started a business. If only I'd asked that person out on a date. If only I traveled over here, which is a place that I wanted to travel to earlier. If only I had spoken up. The regrets about inaction. And what do you tell them?

Like, what do you tell them? So once you find that regret, because again, you say, you're first of all, just talking about or recognizing that it's something that you wish is the first step. But after that, what do you do? Friends, I mean, give me an example of something that somebody like a Leap Academy person might regret.

I had this amazing idea and I didn't go after it. Bingo, okay, there you go. So, and that's a very common regret. And it's actually much more common than people who regret trying stuff and failing. It's much more common than that. There were people in the database who regretted, tried something, let's say entrepreneurship, and went south on them. They regretted doing that.

But I also did a lot of interviews, and there are people who said, I tried it, it didn't work. I didn't like that, but I'm glad I tried. So let's say you have some, I had a great idea, but I never moved on it. All right. So we know from the science, there's a way to deal with that. So number one is how you treat yourself and that kind of thing. And our tendency, and probably you hear it in the sort of the leap Academy, people hear it in their own self-talk, which is I'm such an idiot. I'm so lazy. I'm such a weakling.

I'm such a wimp. I'm a failure. I can't. Yeah, exactly. Like the way we talk to ourselves, it's horrible. It's the worst. It's far harsher than we would ever talk to anybody else. Okay? So here's what the science says about that. Don't do that!

That's basically what the science concludes. And what it says, and the reason not to do that, is that it's not effective. I mean, this lacerating self-criticism doesn't, honestly, it doesn't improve performance. If it did, God bless America, let's go for self-criticism doesn't, honestly, it doesn't improve performance. If it did, God bless America, let's go for it. But it doesn't. It typically has no effect on performance. It has an effect on your mood. It makes you feel worse, but it has no effect on your performance.

And so don't do that. What does have an effect on your performance is something very different, something I didn't know about until I did this research, which is something called self-compassion, which essentially is treating yourself with kindness rather than contempt. Don't treat yourself better than anybody else, but don't treat yourself worse than anybody else. And so treat yourself with kindness rather than contempt. Recognize that regrets are part of the human condition.

Everybody has regrets. It's one of the most common emotions that people have. There's almost nobody who's not five years old or brain damage or a sociopath who doesn't have any regrets. So treat yourself with kindness. You're not that special. Give me any regret that you have. Any of your listeners have a regret? I'll find it in 15 seconds in the database. And so treat yourself with kindness rather than contempt. The second thing, which I think is really important, is writing about your regret,

talking about your regret. Not only is it a way to relieve the burden? But there's some interesting research that shows that when we take this kind of amorphous dread of a feeling, which is abstract and convert it to words, which are more concrete, they're actually less menacing. And so a lot of research about converting these blobby, amorphous kinds of feelings into actual words, which can be help us in sense making. And then finally, what you have to do is you have to stop and extract a lesson from it. So basically what it is for your person, it's this, first of all, you

regret like not starting of, you're not trying something on your own. All right. Trying something yourself. So first of all, treat yourself with kindness. You're not the only one like that. Okay. People make mistakes. That's how it works.

Number two, tell people about that regret, try to make sense of it, Talk about it, write about it. And then third, it's like, this is a pretty strong signal. All right. If you think about it. What are you going to do next? Right. Exactly. This is a strong signal. We make all kinds of decisions every single day. And most of them we don't remember, but here's an indecision that is haunting you. That's a strong signal. So the question is, basically what it says is that you value, what's the lesson? It's you value might value independence more than you think. You might value risk more than you think. You might value creation more than you think. Listen to that signal. And then the question is, what's the next thing that you can do? And so maybe what it is in this case is go meet with five entrepreneurs and get their advice. Give yourself a deadline in the next two

weeks, write a business plan for something you're interested in. Go take a course in entrepreneurship, like basically extract a lesson. The lesson is, this is something that's valuable to me and something that I wanna pursue, then do something about it. And what you don't wanna do is beat yourself up for not doing it until now, that doesn't do you any good.

And I love that you said that, right? Because the clarity will also come from action, right? So when you get into that momentum. I agree with that completely. I think that's a that right because the clarity will also come from action right so when you get I agree with that I think that's a great way to put it. I mean We get a lot of clarity from action And I think the other thing is just normalizing regret right being able to look in in the mirror Say it out loud the one thing that I thought when I was listening to that and again It depends how you look at regret and if it's a little more raw

I think it's easier to talk about things from the scars and from the wounds. So I think when something is like right now in the middle of hurting really really bad, sometimes it's really really hard to talk about it. So I think that was the one thing that I was like, oh how do I help somebody when it's like bleeding right now? But what do you do? Extend your metaphor. You stop the bleeding. You know that's what you do if it's like a right now. But what do you do? Extend your metaphor. You stop the bleeding. You know, that's what you do if it's like a physical wound

and you don't begin the sense making or the lesson extraction when someone has a gaping wound that's- This is not the right time. Not the right time. But when the scar tissue starts to emerge, that's when you can begin deriving lessons from it. Anyway, Daniel, I definitely want everybody

to listen to this book. Maybe just before we end, I do have a curiosity question. Now you have the book out, you're marketing the book. First of all, do you notice a difference between needing to market it now versus a decade ago? Marketing a book is always a ferocious battle. Doesn't matter when or who or where, it's always a battle. It's always, okay.

So how do you then, first of all, motivate yourself to then write another book? Like, does it ever get like, oh my God, not again? Or is it then you just fall in love with another idea and you're like, I can't wait to write about that? I would never write a book just to write a book. I would never say it's time for me to write another book. I would have to be it's something that I want to work on. And so that's why I haven't started working on a new book and instead have been trying to work on some other kinds of

projects that speak to me more clearly, you know, right now. That's what it is. And again, this is where and I'm totally not joking about this. This is where being frugal is helpful and not having very high carrying costs. I have never I'm talking to you today from my garage office. I have never paid rent. I've been working for myself for 25 years. I've never paid rent for an office to anybody else. You have to be very clear about what do you care about? And what I care about is doing stuff

that I find interesting, that's it. And so I'm not trying to build a giant enterprise. I don't care if I have people reporting to me or not. I just want to work on cool stuff. I want to make stuff, put it out in the world, that's it. That's a hard gig, so don't waste your money. Have low overhead. But it's a beautiful gig, Dan.

I love that, Dan. What would you want, and by the way, for people who are seeing us on YouTube, like it's really beautiful to see all those books and all the things, so you're in a really beautiful. It's just a refurbished garage. You can see here. You're in a really beautiful spot here.

So I wish everybody had a garage like this. But Daniel, what would be something that you wish somebody told you earlier in your career that would have helped you? It's a great question. And I think that when I was much younger, I don't know whether I would have listened and that bugs me, you know what I mean?

And I don't think I'm alone in that necessarily, but bypassing that, I think it would be like, no one is thinking about you. No one is watching you. No one is evaluating you. I think a lot of times in our early in our lives, we are concerned about what other people think of us. And I certainly did certainly was concerned about that.

And then eventually discovered what people were thinking about me, which is that they weren't thinking about me. Nobody was thinking about me. They were thinking about themselves. And so there's a liberation in that. Oh, my God. I think what you just said, Daniel, is actually so, so, so important to everybody listening because so many times they're not taking action

because of what society's saying, what people will think, what family will say, what their friends will say. And I think that's the biggest stopper that we see. I mean, first of all, most people aren't thinking about you. They really are not. And if they are, who cares? They don't know you.

They don't necessarily have your best interest in mind. So who cares? There's a danger in living someone else's life. There's a big danger in that. And I think people do it, and they do it in a unintentional way. If you say intentionally, I wanna live the life that my mother wants for me,

or my father wants from me, whatever. In some ways, I want to live the life that my mother wants for me or my father wants from me or whatever. In some ways, I'm okay with that. But I think what people do is they do that unintentionally. They do it kind of passively. They do it as a default. But that's when they wake up with regret. Bingo.

Ties into your book right up there. Daniel, thank you so much. I could probably talk to you for hours. So thank you for coming in the show. Well, thank you, Alana. I've enjoyed the conversation. As I said, it was very therapeutic for me. Ha ha ha.

I hope you enjoyed this as much as I did. If you did, please share it with friends. Now, also, if you're feeling stuck or simply want more from your own career, watch this 30-minute free training at leapacademy.com training. That's leapacademy.com training. See you in the next episode of the Leap Academy with Ilana Golanshchuk.