Leap Academy with Ilana Golan
The Power of Regret: Daniel Pink on The Unexpected Tool to Unlock Your Greatest Success | E101
Thu, 01 May 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
Chapter 1: Who is Daniel Pink and What Is His Journey to Becoming a Writer?
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 you know, as all of us know, is about circumstance. And I happened to, 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. And It just so happens that Ohio in general and central Ohio in particular have an amazing public library system. And 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 library.
Carnegie-funded, massive public library. And so both my parents were readers as a kid. I went to the library a lot, not because I had to, not because somebody was forcing me, because it was good. I liked it. And 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 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 to study in college. You graduated Northern 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.
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Chapter 2: Why Did Daniel Pink Transition from Law to Politics and Then to Writing?
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 Al Gore. Like, how the heck did that happen, Daniel?
It happens in a non-linear half-assed kind of way, as many things do. One of the things about politics, which I really liked, 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 should be yes. And I said, yes. And I wrote a speech. It was probably okay.
And then they said, can you do it again? And I was like, yeah. Can you do it again? Yeah. And suddenly that was my job. And because, again, it's low paid and fast movie. So I started doing that. And then, you know, 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. 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. You know, and 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. And you can get better at almost anything, but there are certain things that feel like,
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Chapter 3: How Did Daniel Become the Speechwriter for Vice President Al Gore?
If there's a superpower that I have, it is frugality. So I don't spend a lot of money. So we just sort of 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 mean, I should have probably. Maybe because I was clueless. You know, I mean, here's the thing, Alana. I mean, 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, you know, 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 like discovering that something is harder than you expect is a reality. And I think I definitely did encounter that. But the being frightened beforehand wasn't a big thing, in part because I planned it out. You know, and 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 going to 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.
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Chapter 4: What Motivated Daniel to Leave Politics and Pursue Writing Full-Time?
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One question about your book, When, for my audience, this is really relevant because you're exploring basically the science of timing, right? You keep looking for different topics. I love that. Like, it's so fascinating. And this book is more about timing. And sometimes it's timing of a day. Sometimes it's timing throughout a project. And you elaborate really beautifully there.
But one thing I do want to talk about is the tricky middle, right? 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 is Human. And that was basically about the science of selling because I was interested in that. And then after that, I said, I'll just give you the genesis of the book when, and 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?
So I was making all these questions about timing and I was doing it in a completely blind, intuitive, half-assed way. And I said, someone's written a book about this. And so I started looking around for the book and no one had written a book about it. And 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.
And so what I did is I looked at a very large number of studies on timing, asking these timing questions. And 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.
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Chapter 5: What Challenges Did Daniel Face When Starting as a Writer?
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 normalizing regret is a really interesting thing. And I love how you're talking about looking backwards takes us forward. We see a lot of regret in those people when they're trying to recap their career and trying to think where they made different decisions. Can we 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, Ilana, to sort of talk about how all of this evolved. But this is not a book that I would have written in my 30s. I would not have written a book about regret in my 30s. But in my 50s, it felt in some ways inevitable because, you know, if you hit age 50, you likely have more of your life behind you than ahead 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, you know, I'm in this graduation ceremony and, you know, I see this kid, not kid, this young woman and... How did that happen?
Exactly.
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 like then they're writing Free Asian Nation. It's like crawling up the stairs of my attic office. And suddenly she's walking across the stage in a college graduation. I blinked and that happened.
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Chapter 6: What Insights Did Daniel Discover About Human Motivation?
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, they're more inaction, regrets, inaction, regrets. 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. 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?
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, it 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.
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Chapter 7: What Does Daniel Say About the Science of Timing and the Midpoint Slump?
Chapter 8: How Can Embracing Regret Lead to Personal Growth and Success?
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 Agent 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. And so we got a fellowship to go to Japan and I studied the manga industry, the comic industry. Because I was very interested in that and then came back and wrote this graphic novel career guide, which was a hoot.
And 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 provides 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. And so you have to pick something that you're genuinely interested in. And I was genuinely interested in this and I wanted to figure it out. And that's what I did. So I wrote that book. And then, again, the goal is to...
for me, at least until recently is, you know, 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 going to make such a big impact?
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