#149: Daniel Pink – How to write like a New York Times bestselling author

May 23, 2023

#149: Daniel Pink – How to write like a New York Times bestselling author
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Dan Pink is the author of five New York Times bestsellers, including his latest, The Power of Regret: How Looking Backward Moves Us Forward.

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Dan is the author of five New York Times bestsellers, including his latest, The Power of Regret: How Looking Backward Moves Us Forward. As part of the research for this book, Dan analyzed 16,000 regrets from more than 100 countries. It’s a great book and I highly recommend it. 

His other books include the New York Times bestsellers When and A Whole New Mind — as well as the #1 New York Times bestsellers Drive and To Sell is Human. Dan’s books have won multiple awards, have been translated into 42 languages, and have sold millions of copies around the world.

Before he was an author, Dan worked in several positions in politics and government, including serving from 1995 to 1997 as chief speechwriter to Vice President Al Gore. You may also know Dan from of his TED talk, the puzzle of motivation which has received more than 10 million views.

In this episode, you’ll learn:

  • Why following your passion can be bad advice
  • When to maximize vs when to satisfice
  • Dan’s rules for writing that allow him to be so prolific as an author
  • And why Dan doesn’t write about the same subject in all of his books

Full transcript and show notes

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Jay Clouse 00:00

Hello, my friend. Before we get into this episode, I want to let you know that I've been playing around with SMS. And I've been learning a lot lately, and I built something pretty cool to test here on the podcast. So if you will indulge me, if you love the show, and you don't yet receive my newsletter, just text creator 266866 I'll say that one more time text the word creator 266866. And you can very quickly very easily be added to that list, I want to see how well this works. I've been looking for a long time for a tool that allows listeners to very quickly and easily opt in to my newsletter. So again, that's creator text that 266866 I'm going to be playing around even more with SMS over the coming weeks. So stay tuned. Thanks for being an early adopter. Now something else that I've been batting around for a long time is writing a book I would love to be an author. So as part of that learning process, I'm speaking with more authors. And today we're very fortunate to hear from Dan Pink. Dan is the author of five New York Times bestsellers, including his latest book, The Power of regret, how looking backward, moves us forward. As part of the research for this book, Dan analyzed 16,000 Different regrets submitted from individuals from more than 100 countries. It's a great book, and I really highly recommend it. His other books include the New York Times best sellers when and a whole new mine, as well as the number one New York Times bestsellers, drive and to Sell Is Human. Dan's books have won multiple awards. They've been translated into 43 languages, and they've sold millions of copies around the world. This interview is full of very interesting, candid stories and anecdotes about writing books, including this one. I realized, like this book proposal I'd written and I was like, you know, I've written 35 pages. I don't think this is a book.


Dan Pink 01:55

And I'd rather find that out now than when I had a contract for it. And I think that a lot of books that you see the lot of the weaker books out, there are books where that would have benefited from people doing that vetting process.


Jay Clouse 02:08

Before he was an author, Dan worked in several positions in politics and government, including serving as chief speechwriter to Vice President Al Gore. You may also know Dan, from his TED talk, the puzzle of motivation, which has received more than 10 million views.


Dan Pink 02:23

The good news about all this is that the scientists who've been studying motivation have given us this new approach. It's an approach built much more around intrinsic motivation around the desire to do things because they matter because we like it because they're interesting, because they're part of something important.


Jay Clouse 02:37

So in this episode, you'll learn why follow your passion can be bad advice, when to maximize versus when to satisfies Dan's rules for writing that allow him to be so prolific as an author, and why Dan doesn't write about the same subject in all of his books. I'd love to hear your thoughts on this episode. As you listen, you can find me on Twitter or Instagram at Jay Clouse, tag me say, Hello, let me know that you're listening. And now let's talk with Dan.


Jay Clouse 03:17

I've heard you say in the past that you don't like the advice, follow your passion. And I'd love to dig in more on that. And hear your your stance on why following your passion is not your favorite. Yeah, okay,


Dan Pink 03:29

so so so so here's the thing. So I don't I, I'm gonna offer a slight amendment to that. So I'm not necessarily deeply opposed to following your passion. What I am deeply opposed to is that if you are a young person, or if you are at a juncture in your life, trying to figure out what to do, I am deeply opposed to asking yourself the question, what's your passion? I think that's a terrible and even insidious question. And the reason for that, Jay, is that? Well, there are a lot of reasons for it. But among the reasons for it, are one, it's a hard question to answer. I don't know if I could ever give you a good answer to that question. There's a lot of pressure when somebody asks you that question. And when you ask yourself that answer, you have to come up with a really, really good answer. All right. So I think that it actually freezes people. The second thing is that it is a little bit too much directed internally rather than externally. I think there are two better questions in that one of them I have got from my friend Tom Rath, the other one I got from my, my own experience. And so the question I got from my own experience is this. What do you do? What do you do? What do you do when nobody's watching? What do you do? Because you can't help yourself? What do you do because it's part of who you are. And and I became a writer in part by asking myself realizing I should ask myself that question, which is not asking himself what my passion is because I've been a writer for a long time. I mean, I don't know if writing is my passion. I'm not sure because writing is a giant pain in the ass a lot of the time. And but if you if you ask if I discovered at some point in my life, maybe in my 20s, even my early 30s, that's what I did that I would say, That's what I was doing. That's what I was thinking about. And I think that's a better question, then what's your passion? Because in order to do good work, it requires a degree of pain, a large degree of pain, or some of the stuff you have to do to create good work is boring. Some of the stuff you have to do to create good work is really, really difficult. It's uncertain, you're living in ambiguity. It's not in the moment, extremely fun. But you do it, because that's what you do. Now. Tom Rath has another beautiful question that you can ask yourself, which is this? Not? What's your passion? But where can I make my biggest contribution? Where can I make my biggest contribution? And when Tom told me that question, I find that really powerful too. And I think that's a really helpful question to ask, because that also is externally focused, it's the question of what do you do is focus more on our behavior rather than our effect? So it's something external in the world? And then what the question about your contribution is focused on your impact of those actions. So I think those are


Jay Clouse 06:19

better questions. Something I'd love to get your take on along these lines. I see this all over the place, because now that we're all walking, talking micro media companies, a lot of young ambitious people feel almost like directionless with their ambition. They're like, I know, I want to leave a dent. I know I want to make an imprint on the world. I know I want to contribute something and I have so much energy, but I'm just not sure what to do. I'd love to hear your advice on first steps people in that circumstance should take to start answer this question of what do I do?


Dan Pink 06:54

Start small? Do one thing? Don't Don't answer that question on a 10 year time horizon. Answer that question only one day time horizon, ask yourself, What's if I could do anything today? What would I do? And what would be my biggest contribution today? And then do it again the next day? And do it again the next day and do it again, the next day? A lot of times those those, those those mega questions that people are asking, understandably, sometimes, you they make sense only in retrospect, that's that's one thing. The other thing is that is that in some level, we've gotten the sequence wrong. We think that the way we move through the world is that we figure stuff out, and then we act. And I discovered, in some ways, the hard way, Jay, that that sequence has reversed, that the way to figure things out is to act, that doing stuff, and acting is a form of figuring out and in some ways, it's a little indulgent, to sort of say, I'm going to, I'm going to operate only in my own head and try to understand how things are going. And then I'm going to have this carefully architected plan that I'm simply going to execute. That's not how the world works.


Jay Clouse 08:07

Something that I see paralyzing a lot of people is, there's almost a dogma now, that since there's so much information out there, and we're all, you know, pushed in a direction of maximizing everything we create, like, we feel like we need to take the perfect next step. Because if we're not doing this all in perfect sequence towards this perfect outcome, we're wasting our time. And I think that's a real disservice to people because it feels like there's not the safe space to play. Yeah, yeah, just act for acting sake. I wonder if that's like uniquely, this time period we're in because I think about your career, starting with your first book free agent nation in 2001. And you weren't pressured to like write on Twitter about the process of writing this book? Do you think that the times have changed for writers who ultimately want to write books but feel like they have to be publicly publishing constantly?


Dan Pink 09:07

I'm not sure. I really, I'm really not. You know, part of me says, yeah, it is a different landscape. And you do need to be out there more and more often, and that a lot of this social media is very much a volume game. So you have to just keep at it and keep at it and keep at it. And, and that can be I think there's some, some dark sides of that. On the other side, I think there's something to be said for just, you know, doing your work and trying to do as great a job as you possibly can and not stressing about about everything. I mean, we you use a very important word there J which is maximizing. That's a very important word. And we have, you know, Barry Schwartz about 20 years ago, who Barry Schwartz is a social psychologist, was at Swarthmore for a long time now he's at the University of California Berkeley. And he wrote a very with thought his collaborator, his name is escaping right now a very interesting paper, but 20 years ago, maybe even a little bit more about the difference in decision making between what he called maximizers and Satisficers. maximizers try to get the best out of every decision I'm going to have not only I'm going to write the best blog posts today I possibly can, I'm going to order the finest hamburger in the city of Washington DC. I need to get my roof fixed. I'm going to Find the Best Roofer In the Delmarva area, alright, so they maximise on everything. Satisficers say, I'm just going to write a good enough blog post, I'm going to write a good enough eat a good enough hamburger. And what's interesting is that what Schwartz found is that is it maximizers do achieve more sometimes, but they're miserable. And to me, one of the questions of life is how do we decide what to maximise on and what to satisfice on. And the older I get, the more I realized that a lot of the stuff we just want to frickin satisfice on. And we want to save our energy for maximizing on a few things that are incredibly important. And most things are not incredibly important. And so I think figuring out that balance between where do I satisfice? Where do I say good enough? is good enough? And where do I maximize is extremely important. And I deal with this literally every day. So you know, I mean, this morning, I was writing an email, and I was like Reek, I was recrafting the email. And ultimately, it didn't matter whether I had the most brilliantly crafted email today and what it was going to do because the person reading it was probably going to take 14 seconds and then never thinking about it again. So what was I doing on that one, I should have been satisficing. And what I should have been maximizing on was, you know, spending some time this morning, which I did not do in developing new projects. So so all of us fall prey to that. And I think it's a really important question, where do I satisfice? And where do I maximize and in my view, many people maximise on too many things, and satisfice on too few things.


Jay Clouse 12:07

I love that I recently heard the idea that the young man knows the rules, and the old man knows the rules so that he can break them. Or this idea that mastery is knowing what to ignore. I love these these concepts of deciding where to compromise on effort or focus for the benefit of other things. Because you know, the the more time that I spend this content creation world, the more that I realized time allocation is like everything is the question that drives every day. Where am I putting this time right now? What am I deciding on, on spending time on and I know that historically, you've kept your business as a creator? really lean? I think the last time I heard you or your company is you and your wife, correct? Yeah,


Dan Pink 12:50

absolutely. You know, that's a that's a decision that is partly a business decision and partly a lifestyle decision and partly a what you're good at decision. So I can I can parse those out. So the business decision is what I say to everybody. Listen, I have been I have been self employed for 25 years, I can't even believe that I've been self employed for 25 years. I can't even believe that, Jay, when I'm saying that. And I have never had an office outside of my home. Why? Because I don't want to pay rent to anybody. Okay, playing rent to anybody is taking money out of my pocket and putting it in someone else's pocket. And even though I don't have an MBA, I have an intuitive sense, that's not a great idea to do at scale. Okay, so so and the other thing is, and I see this people screw this up all the time is low overhead, man, you know, low overhead, we, you know, it's not only about it's not only about revenue, it's about the bottom line. And, and so keeping your keeping your costs minimum, and staying lean and mean is a way to continue doing the work that you want to do. That's one thing. Second thing is lifestyle. I have zero interest in waking up in the morning and running a company zero. I like to wake up in the morning. Well, what I like to do is wake up in the morning and have a cup of coffee and like read three newspapers and not actually do any work. But on the days that I push past that instinct, I instead want to go into my office and figure stuff out that other people haven't figured out and create stuff and put into the world that's it. I don't want to run so that's that's the lifestyle point. And the third point so what did I say? I said business lifestyle Oh yeah. And what you're good at? I'm not good at running stuff. I'm not good at managing people. So again, as we drop these life lesson bombs on all of your listeners hear Jay the other one get ready because it's about to detonate the other life lesson bomb is along with figuring out where to maximize and where to satisfice why should not ask, what's your passion, but instead ask, what do you do? And where can you make your largest contribution? You should also ask yourself this question, what am I not good at? And what I'm not what I'm not what the there's a whole universe of things that I'm like, but, but among the many items in that universe, is I am not good at running stuff at coordinating stuff at leading people at organizing people. That's not what I'm good at. So I shouldn't do that. What you


Jay Clouse 15:30

are good at is publishing best selling books. Love the power of a grant, I love the idea of turning this over in our mind and interrogating this belief of should regret be bad. I'd love to dig into what makes you great as an author. And in the process of writing a book. What are you thinking about maximizing? Because there's a world where you spend all day on Twitter, engaging with people who are saying, I love reading Dan Pink's book and feel all the dopamine hits all day. But to write a deep work of nonfiction probably requires your time to be doing something different. So how do you think about allocating your time?


Dan Pink 16:08

Don't waste don't fritter away your day on Twitter, number one, I mean, I mean, you know, I mean, seriously, I mean, you know, I don't I'm not like anti. So So I mean, among the things that you can do, I mean, I've done this myself. I mean, I will. I think you have to put in some, I think you have to put in some guardrails, because it's because you have to recognize that this these technologies are designed to addict you. They're designed to suck you in, they're designed to distract you from things that you want to focus on to the things that their advertisers want you to focus on. Okay? So you are you have to be you have to recognize that you are being manipulated, here. Now, that's not always a bad thing. When we watch a play, we're being manipulated by the playwright and the actors on the set designer. So it's not an inherently bad thing. But you are being manipulated. So I think you have to put in some guardrails there, give you some guardrails that I've used, I don't have this right now. But it's other points, I've just taken Twitter off of my phone. So I don't have the instinct to if I'm waiting for a bus or whatever, to check Twitter at that moment, okay, so take that off your phone, you can also do things at least on the iPhone, where if it is on your phone, you can put in a time limit. And so you can set you know, so you can say after and my time limit is the smallest increment that you can use there, which is five minutes, five minutes a day can be can be plenty, and then it's like, oh, you're up, you're out of time. That's that's the other thing. And the other. The other kind of guardrail that I've used, especially when I'm, when I'm writing is, it is an inviolable rule that I do not look at any social media of any kind, during my writing hours, or when I'm trying to make my word count, ever, that I treat that I try to treat that rule, I usually am fairly successful in treating that rule, I treat that rule in the same way that I don't. During my writing time, I don't have you know, three martinis either, because I know that would be destructive to my creativity and my productivity. So So I think you can put in, I think you can put in guardrails that way,


Jay Clouse 18:09

after a quick break, Dan, and I dig into his approach to writing and later we talked about how he chooses the subject of his next book. So stick around, and we'll be right back. And now back to my conversation with New York Times best selling author, Dan Pink, can you tell me more about your writing hours and your word count?


Dan Pink 18:30

Sure, when I'm working on, especially when I'm working on a book or a long article, you know, I tend to treat the I tend to treat the writing like a, like a job like a like, in some ways. You know, the the example, the analogy, I've used many, many, many, many, many, many, many, many, many times is a bricklayer. So I have a job to lay bricks into essentially to build some kind of structure with bricks. And my job is to come into my office every day and lay the bricks. And it doesn't matter whether I'm in the mood to lay the bricks or not. That's irrelevant. My job is to show up at 830 in the morning and lay the bricks and I find that if I have a specific time I need to be in the office. And a specific number of bricks, I need to lay that as a word count. What I do is I established that time of coming into the office, I established that word count, which for me, since I'm a very slow writer, it's not a massive word count. Sometimes it's 500 words, sometimes it's 700 words. And I don't do anything until he hit that number. I don't look at my email. I don't I don't even bring my phone with me into the office. But I don't look at my email. I don't do anything else. I don't have to schedule any kind of appointments. I don't do anything else until I hit that number. And then I'm liberated to do other things. But then I do it the next day and the next day and the next day and the next day. And that's how you get shit done.


Jay Clouse 19:53

When you've taken on other projects like working on the TV show with National Geographic, do you would take a hiatus from like the writing hours.


Dan Pink 20:03

Yes. And here's the thing. Okay, get ready, put on your Flak Jacket, listeners, because we got another knowledge bomb that's about to go off. All right, I mean, another life lesson bomb that's about to go off. I think you also have to understand how you work. Okay? And there are people who are I mean, this is an old fashioned way of thinking about it. But there are people who are very effective serial processors, they do they do something in sequence, I do this. And I do that, then you do that. And there are other people who are more powerful parallel processors, they can do things in parallel. I'm a serial processor, I'm not saying one is better than the other. I wish I were a parallel processor. But I'm not. I'm a serial processor. So I tend to do things I like to work on basically one thing. Again, that's not saying that everybody should do that. In fact, I don't think everybody should do that. But I do that, for better or worse. And so so I will so. So when I'm in the really, when I'm in the throes of writing a book, I close my calendar entirely to anything, I don't do anything else. And certainly when I take out a big when I take out a big project like that, that you just mentioned, I close my calendar entirely, so I can focus on that. And, and only that Now occasionally things will infiltrate. But that's that's that again, that's your mileage may vary listener, but that's how I do it.


Jay Clouse 21:32

One thing I really admire about your, your career as an author is, it's very clear, like you said earlier, you've you followed your interests, you know, you went free agent nation talking about the future of working for yourself, you have A Whole New Mind, which is about right brainers versus left brainers. Then you have a career guide, The Adventures of Johnnie Bunco, which I've heard you say is one of your favorite books that you've written. And these things are tangentially related. But it's not as if you've written like free agent nation, and then six follow ups in that same DIRECT cannon. Right. So I would love to hear how you think about the sequence of your books and how you choose an idea to dive deep into because you do such a deep research since these things aren't necessarily perfectly sequential.


Dan Pink 22:17

Yeah, I mean, the truth is, I actually don't think that that much about it. Like to me, that's not the question. That's not, again, the ones your mileage may vary. That's not how I think about it. What I think about is, what is an idea, a concept that I want to wake up and grapple with every day, intensely for the next few years, and will end up wanting to end up talking about for the next 1020 years. And the truth is, that's not most things. And so you have to have a very high bar for that. And it doesn't matter much whether the second book I work on or the third book I work on is a somehow perceived as a natural outgrowth of the first or second book I've worked on. Now. I mean, if I started writing Gothic romances, right now, I think that that might be far afield, and people would say, What the hell are you know, like, it would make no sense at all. But But I have no I have no I have no interest in doing that. I think that you have to find something that you care deeply about. And you're willing to spend all of your time and energy over both that concentrated period in the shortish run couple years. But then also, you know, talking about you know, for the rest of your for the for the rest of your your life, I mean, I got a I just gotta I gotta press inquiry this morning about a the book on timing I wrote, that was only four years ago, but I've gotten print, and I'll get present worries on, on, on stuff I wrote 10 years ago, or 15 years ago. And that's cool. Because I care about this. I care about those ideas, but But most things I don't you don't care about. So I think it's really important to find something that you are deeply interested in. And here's the thing. I really believe that if I'm deeply interested in something other people are going to be deeply interested in it. It's not like I have some kind of exalted preferences or taste or I'm such a unique individual, that if I'm deeply interested in how to be more effective in influencing and persuading and selling that I'm the only one who's going to be interested in that.


Jay Clouse 24:42

I asked because it's, it almost gives people permission. A lot of creators starting today. Again, they feel this pressure Yeah, to maximize the path they're taking. And the advice is typically like you've got a corner yourself as the blank. Got Yeah, you know the future of work guy though, right? Alright, guy. Yeah. And it's, it sucks. Well,


Dan Pink 25:05

I mean, I think you know, again, again, I'm not saying that my experience is necessarily what everybody else should do. I'm just telling you what I do and why I do it. Now, I think that there is there is something to be said for, you know, cornering the market conceptually in some ways, so that so that people always think of people, you know, people always think of you, I think I can see that there is something to be said for that, in the shortest run, in the longest run, I'm not sure. Because I've seen this too many times, where people essentially, like, you're not doing readers any good writing the same book three times, although lots of people do that. I mean, I, there are authors, I know who, basically, who really can't give me a good explanation about why Book Three is different from Book Two is different from book one. Because they're essentially just rehashing the same thing. You know, so, and the thing is, is like, first of all, I think that's boring. Second of all, I think it doesn't do a service to readers. Third, I think for 99% of people, it's a terrible commercial strategy.


Jay Clouse 26:11

Can you say more about that?


Dan Pink 26:13

I mean, you said something, you said something original, and people liked it. So to pretend that you're saying something new about that idea, when you're really not. People can see through that, again, they're charlatans and posers and so forth, who end up doing well, that's true in every field of any kind that has nothing to do you know, like, you know, there's like, I mean, any this is like, this is like, another thing that I think younger creators have to deal with is that what happens in a world of when you're dealing with anything that is about art, ideas, concepts, stories, media, anything like that, when you're putting stuff out there in the world, and you're getting evaluated by large numbers of people, and some things are hits, and some things are misses. And some things succeed. And some things don't, that you're going to look around. And you're going to say, that person succeeded. And that person sticks. That person is putting crap out there. And it's incredibly annoying. I'm with you on that. 100%. But you know what that happens. What also happens is that somebody else puts out something that is great, and it doesn't get the doesn't get attention or doesn't get the attention it deserves. That happens a lot too. That stinks too. I hate that. I hate when I see people doing great work, and doesn't go anywhere. That is a that is frustrating. I mean, obviously it's frustrating, deeply frustrating and vexing to them. But it's frustrating to me too. And you know what, there's nothing you can do about that. What you have to try to do is create the best stuff that you possibly can push it and share it with the world as robustly as you possibly can with with a degree of intensity, that I think that is often underestimated in order to make and then recognize that there's an enormous amount of luck and fickleness in the market out there. But I do think, again, when we're talking short term and long term over time, that's generally good strategy. Doing stuff you care about doing a great job, caring deeply about quality, being relentless about sharing it with the world over time. I think that works more often than it doesn't. But people don't like this overtime part. Unless the time span that I'm talking about here is three months. And when I say you know what it might take five years, or eight years, or 12 years, they don't like that at all. Yeah, that's the way that's the way that is. And it's completely annoying to me, I sometimes will look at like the list of books that have sold well, and there'll be other books, I think, okay, great. That's a great book that deserves to do really well. And other times, we'll see Oh, my God, what is wrong with you people out there, this, this person is a charlatan? And what they're saying is ridiculous.


Jay Clouse 28:58

How do you deal with that? Because a lot of times, let's say you recently released the book, and you're you're shooting for the New York Times bestseller list. Timing plays such a factor because do you even have awareness of what other books are releasing on the similar timescale?


Dan Pink 29:12

Barely, barely, that's something that you have no control over. And also those best seller lists. I mean, again, I don't want to be glib here, those best seller lists are kind of there, they've lost a lot of their meaning over time. What they used to be a somewhat important kind of gatekeeper now when people have access to all this kind of stuff doesn't really matter that much. Also, just there's there's some analytic problems there and that basically, best seller lists measure sales over a seven day period that is, like completely meaningless, you know, so so people who make the best seller list you know, for one week, it's like, okay, you had very you had very high velocity for one week, but you didn't ultimately go anywhere. So So that's, that's, I think that's a it's a distraction. We have a lot of distractions like that in our midst like US News. and will report rankings which a lot of colleges are obsessed with and a lot of parents and students are obsessed with. That's nonsense as well. I mean, I think it'll be even bigger nonsense of the bestseller lists. But what the publishing industry doesn't want us to actually publish the actual sales of books, because they can, because the dirty little secret isn't most books don't sell very many copies at all. And the books that publishers are proud of sell very few, which is why like things like the New York Times bestseller list, you know, has has basically a segregation policy where on the fiction list, they don't allow romance books, they don't allow juvenile books. They only allow adult books that they consider that the New York Times editors consider adult books on the nonfiction list. They don't allow advice how to miscellaneous because those books sell a lot.


Jay Clouse 30:51

So as you're approaching the release of a book that you just spent years writing, you feel very strongly about, how do you set a goal for what success looks like, for the release of that book was I mean, you


Dan Pink 31:03

focus very much on process rather than outcome, which I think is another important thing in general in life, because I can't control I can't control the outcome. What I can control is the process. What I can control is being willing to do as many interviews as I possibly can about the book, being willing to talk about it to as many people as I possibly can, being willing to think through what does this mean for people in this profession? What does it mean for educators? What does it mean for people in the creative professions? What does it mean for this kind of industry? And thinking hard about, you know, what is the payoff to these groups to hear from me to talk about this, this stuff, and actually, again, as I was talking about earlier, J, really going all in and not saying, Oh, I'll do this for 10 days and see what happens. But basically saying, I'm going to do this for six months, and see what happens, and not get freaked out if things don't pop immediately. But also not get too pumped if things pop early, because that's meaningless to is basically go in it for the go in for the long run. I had a


Jay Clouse 32:01

previous episode of the show with Nathan Berry, the CEO of ConvertKit. And he had a statement where he said,


Dan Pink 32:07

have you given this every possible chance to succeed? Because if yes, if you have, you really want it, you've given every possible chance to succeed your best effort, and it hasn't worked. Like it's time to shut it down and move on. Maybe you're not the right person for it. Maybe the timing isn't right. The idea isn't right, like any of these things, and you in good conscience can move on. For me, the answer was no.


Jay Clouse 32:32

And so there was a disconnect between what I said I really wanted, and the effort that I was putting in. And that question just like haunts me, because how often do we actually do everything in our power to make this thing that we spent so much time on be successful? It's also hard question to answer to like, no, like, did I do that? No, it anytime I've asked. It's been like, No, I haven't.


Dan Pink 32:52

Yeah, yeah. And I think that's the question. I think that's I think that's the baseline answer to that question. But you know, the other thing that I would say is also to listen to, you have to listen to the feedback, you have to listen to what people are saying, how are people reacting, I listened very carefully to that I read every reader email that comes in because it gives me a sense of who's reading and what they and what they and what they care about. And also equally important, what they don't care about. When you start talking about your set of ideas. If you think about a set of ideas in a book, or at least a decent book, there are multiple ideas in there. They're multiple, they're multiple things that you can share with readers. And when you go out and talk about it with audiences from the very getgo, you begin understanding whoa, wait a second, people are really responding to that. I never thought they do respond to that. People don't care. Oh, what about that? Wait a second, that's awesome. What's wrong with these people? And you know, when you start getting that feedback on things like that, I always look in my books at what is what is most in the Kindle versions, like what are the most underlined passages. And I'm always surprised by that, of what the most underlined passages are, that tells me something. And so So my advice is, you know, focus on the process. Focus on you know, doing everything you possibly can recognize, and you can't do everything. But then also be alert to feedback, be willing to change be willing to change course, if you say, like I wrote a book called A Whole New Mind, I think you mentioned it earlier. And I wrote it as a very much as a business book. And in literally from the first few days, it was out, I started hearing from educators and I was like, it's weird. I didn't think educators would read this book. And an educators ended up being, you know, an audience for that book in a way that I never anticipated. So I could have ignored that and said, What are these teachers emailing me for? This is a business book, but I get to listen to that very carefully.


Jay Clouse 34:45

When we come back, Dan, and I talk about how he selects the subject for his next book, right after this. Okay, now let's get back to my conversation with Dan Pink. One of the things I've heard you say about your your time as a As a political speechwriter, was that one thing you liked about the work was the project based nature of some of it. And I liked that about the idea of books as well, because it feels like yeah, a project or podcast, yeah, or podcast. But on the same side, I feel like I have to publish this thing weekly into perpetuity. And there's like, pretty tight confines of what an episode of this show is. Yeah. Now that you're on the other side of publishing the power of regret, what do you how do you approach the next project, when you know that you've decided what that project will be?


Dan Pink 35:32

A couple of things. Usually, when I, you know, I think it begins with when I can't get out of my head. And also when, when not only get it into my head, but when I went, you know, when I want to keep talking about it with people, that's often a sign. But what I also do for any book, for instance, is I write a, you know, reasonably substantial book proposal for every book that I write longer than I might necessarily need to book proposals, you know, sort of functionally are really marketing documents. I mean, you can usually get by with, you know, something relatively short and straightforward and concise, talking about what this book is, what what is about why no one has written it, why you're the perfect person to write it, what the what the, you know, what your credentials are for writing it, giving some examples of how you would execute it, giving some examples of the substance that would appear in the pages and being clear who the audience is for that book, that doesn't necessarily have to be a very, very long document. I ended up you know, I ended up writing book proposals for longish book reveals for every book that I do. And the reason I do that is that the act of writing the book proposal is a test of the concept. Number one doesn't hang together. Number two, do I want to work on this? So I've written several book proposals that never went anywhere. Why? Because in writing the book proposal, I discovered, either this isn't a book that's happened before. Or this is the book I want to write. i Okay, this is kind of interesting. But I don't want to get married to this idea. I'll go out on a few dates with this idea. But I don't want to get married to this idea at all. I didn't want to go steady with this idea. And, and so and that's, and that's, and that's really important. You know, I think that in some ways, I think both of are really important. I mean, there was one example from two years ago that, that I realized, like, this book proposal I'd written and I was like, I've written 35 pages, it's like, I don't think this is a book. And I'd rather find that out now than when I had a contract for it. And I think that a lot of books that you see the lot of the weaker books out, there are books where that would have benefited from people doing that vetting process.


Jay Clouse 37:43

I love that as a filter, because so often, I mean, any creative could do a foe proposal for any project that they want to take on to themselves actually, right. Jack has so easy to get really excited about something exactly announce to the world, you're going to do it now you're committed now you get oh my gosh, I love that as an exercise.


Dan Pink 38:02

But I mean, your analysis of it is your is sharper and better than mine. Because it's like, you can you can, you can come up with it. And you can feel good about that. But you haven't done the you haven't done the hard work of trying to make it work and make it hang together, which you're going to have to do eventually. So it's, you know, you can pay me now or pay me later. And I want to know that stuff early rather than late because if you discover it late, it's miserable.


Jay Clouse 38:30

Something about your work that I think a lot of people can learn from and benefit from, is you take a research backed approach to all of your writing. And I feel like any piece of content can be made more interesting, more valuable, if you have more proprietary research backing it up. And it's not just opinion, we're so incentivized just to throw polarizing opinions out there because they get a reaction. And it's easy to put together when you don't have to back it up and research. So I'd love to hear your process of research because it sounds like an intimidating thing to capture 16,000 Regrets before writing the book or running this, this research process. But you've said today, you can do that with one or two people from your garage. So can you can you talk about how you go about research?


Dan Pink 39:16

Yeah, you can do that. The thing is, here's the thing. It's like, it's a lot of work. That's all that it is it's not a matter of brainpower, it's a matter of putting in the time of you know, going back and laying those bricks. You don't have to be a genius to do a lot of stuff. But you know, you know what you do have to do and a lot of people aren't willing to do that. So they Oh, I'm gonna do a summary. I'm gonna do some research. And it's like, you know, it's like, Do you Do you want to read? You know, this? Oh, I read a paper. Okay, that's nice. Are you willing to read 25 papers as a start? And 200 papers and most people aren't. You know, are you just are you are you willing to do that work? And most people aren't because it is difficult and it's unglamorous. And a lot of it is kind of boring. And it takes a very, very, very, very, very, very long time.


Jay Clouse 40:08

And what does that look like? Does it literally look like? Do you? Have you had to go to just like libraries and read books on the subject and papers? Or has the internet given you enough firepower to do most of the research from your computer? Now?


Dan Pink 40:20

I don't have to go to libraries that often. I mean, you know, in the old day, the pre pandemic days, I would, I would have to, you know, I would go out and, you know, report things and interview people in person. But I mean, here's what it looks like J. What does it look like? It looks like this. Okay, this is like, one. But that's like, let's this like, 1/50. All right. It, you know, you have to be willing to, you have to be willing to turn, you know, to turn every page. And that's and that's hard. And it's unglamorous and it's sometimes boring, and most people don't want to do it.


Jay Clouse 40:56

How do you know when you've done enough?


Dan Pink 40:58

That's a good question. I don't think you always do. For me, it's very instinctual. But I think it becomes when when I start hearing the same thing over and over again. That is you can almost chart it out. It's like you're let's say you're you're saying okay, so I need to I'm going to give you an example. What does the science say about the importance of feelings of belonging on academic performance? I'm totally making that up. Okay. And so you start out with a hunch, okay, about what it will say. And then if you were to chart it, you say, Oh, I'm learning more, I'm learning more, I'm learning more, I'm learning more. And then at a certain point, you say, Wait a second, I'm hearing the same thing over and over again. And you look at your notes, and it's like, okay, I already wrote that down. Oh, here's somebody else saying this same exact same thing. So you get this instinct, when you're when you're plateauing. And it goes back to what we're talking about earlier, which is basically at a certain point, you have to say, Okay, this is I got this down, more or less. Now, I'm not getting a PhD. in the, I'm not reading a PhD thesis in belonging in academic performance, what I want to do is I want to master the basics of this, get it right, lock it down, and, and move on. And so when you feel yourself, at least I do when I feel myself plateauing there, I basically have to, you know, as as as much as I would like to read for more things, because it's a lot easier than writing, you have to say, okay, stop there. And then there's also the test of, well, I've done the research, can I explain it in a way that is crisp and coherent? And sometimes you can. And so you start explaining, and you're like, oh, wait a second, I actually don't understand this, as well, as I thought, or, Oh, I never thought about this point, you have to go back and do some more research. So all of this is all of all of this, like, if you want to do this, right? You got to do a lot of work. That's you know, you don't have to be very smart, believe me, you just have to be able to you have to be willing to do a lot of work. I think it's true for I think it's true for anything you look at, like these works of you look at these works of history or biography that people write to take 578 years to write, you know, and you look at this, and it's like, wow, this is like, took so much work to do to find all this research to put it together in a coherent way. You know, this is I like my, my hat's off to you, and you're doing me a service as a you're doing me a service as a reader.


Jay Clouse 43:23

That's the opportunity, though, you know, this is the mindset shift I'm trying to have myself constantly is you have these narratives where you say, oh, but that sounds like a lot of work or That sounds hard. But that's exactly why that makes something valuable. That's why other people aren't doing it. That's the opportunity for you.


Dan Pink 43:38

Bingo. 100%, behind you on that one. On both. Okay, so so so on both dimensions of that, number one is that that's what makes it value sit perfectly. That's what makes it valuable. And also, that's what allows you to, you know, go back to the famous business strategy metaphor of red ocean versus blue ocean. All right, cranking out short term, hot takes on things, you know, is a red ocean, all right, but coming up with research based, interesting, relevant, useful things that they can't find anywhere else. That's blue ocean, you know, and so it's, it makes it more valuable, but also fewer people are doing it. So it's ultimately in the long run a better business.


Jay Clouse 44:26

I've even heard you say that when you're in the editing process, you will read your book manuscript to your wife and have her read it to you fresh sound when I heard you say that that sounded so painful to me. I'm like I can't imagine doing that.


Dan Pink 44:40

Painful that is so I mean, it's it's painful to me, but it's way more painful to her. Oh my God, that's how you do it the opportunity. That's how you do it. You know, and and again, like I just I'm sorry to sound like the old man on the porch here. But, you know, we this is I'm not saying anything new. I hear you talk to anybody who cares about how to play the violin well, and they'll talk about it this way. You talk to any athlete, about how do you get good at tennis? How do you get good at basketball? They'll talk about it this way. You know, and then I just, you know, it's just like, my experience has been, there's some people who are willing to put in the work, and some people and many people who aren't. And if you're somebody who is willing to put in the work, really willing to put in the work, not perform, putting in the work, but really putting in the work over time, you're going to be fine.


Jay Clouse 45:37

Let's play that forward. Let's say I'm listening to this, and I aspire to writing my first book, and I'm willing to put in the work. What do you see as the best strategy for for a first time author? To get the opportunity to write their first book?


Dan Pink 45:52

Make sure that what you're what you envision is a book. Okay, that's a big is it a blog post? Is it an article? Most things should not be books? And so make sure that it is that actually it's worth? It's worth buying a book? You know, ask yourself this question, Would someone who doesn't know you who's not related to you? Why would they be willing to spend nine hours reading this stuff and $25 on this, like the nine hours that they could have spent doing something else, the 25 bucks that they could have spent on something else? Someone who doesn't know you, who's not your relative who's not trying to do your solid? Why would they want to do that? And, and you have to be willing to answer that question. This is why like, a lot of books that come through into my office are that they don't they don't meet that test. Because they haven't so so. So my first thing is like, make sure that what you're writing is a book. And not simply something else, everything doesn't have to be a book, there's no magic, and there's no magic in a book, if you write an article that a lot of people read, that changes their behavior that is useful to them, that allows them to see the world in a new way. That is a powerful contribution to the world.


Jay Clouse 47:07

Okay, so I have an idea, I'm pretty sure it's a book, what should I do next?


Dan Pink 47:12

What you should do is that you should write a one page summary of that book, and share it with five people whose opinion you you respect and see what they say. Get see what they say and say, What advice do you have for me? And if they're good friends, they might say, this is interesting. But I don't want to read 300 pages about this. Or they might say, Hey, have you ever thought about this? Have you ever thought about that? Maybe you should tweak it this way? So think about that. Another thing that you should do is that you should ask yourself this question, if this book is such a freaking good idea, why hasn't someone written it already? Because in some cases, maybe they have. And you just don't know about it. All right, or there could be another reason why they haven't because it doesn't work or doesn't hang together or something like that. And so so so what I would do is I would start small, do a one page version of the book, get some feedback, maybe then do a two or three page version of it, get some more feedback, maybe write an article for public consumption about it, get some feedback on that. And then look hard at what is already out there. And trying to figure out why hasn't anybody written this? Or has somebody has somebody written this? And if not, why not? And in that case, you know, sometimes the answer to that is like, no one thought about it before no one was able to pull it off, or people have tried, but they failed for this reason. And I think that's I think that's the I think that's the way to go my view. Again, your mileage may vary. Often when I'm working on something, I like to talk about it with a small set of people. Not with everybody, I don't not not not super publicly, but I like to talk about it serve socialize the idea. I mentioned it to people see what they think. And so and have people say, Hey, have you ever thought about this? Have you ever thought of it that I don't believe you, you're wrong, that'll never work? You know, just whatever they have to say and really take that. I actually love hearing that stuff. And it to me, it doesn't matter whether it's positive or negative, it's just that I'm getting a reaction is what I care about.


Jay Clouse 49:17

I love this focus on concept development, because I expect to really answer that question you would give me kind of a, a task list of okay, here's step by step the process for getting this into an agreement with a publisher, which was actually kind of what I was looking for. But I like this better, because this seems like a better this seems like a better, more practical approach to what am I even getting into and does it make sense to get into it?


Dan Pink 49:42

I would do that. Yeah, do I mean yeah, develop, develop that and then only then start looking around for interview. If you really want to write a book, you're gonna have to find a literary age and that's the way this world works. And so you know, but you're going to be you're going to be on stronger footing, firmer footing in reaching out to an Agent if you've done some of that due diligence and that vetting well in advance,


Jay Clouse 50:04

how much research do you think a first time author should do before approaching a literary agent? Versus after? You know, they're in the process of writing


Dan Pink 50:14

that depends on? That's, that's a hard one to answer because it depends on who the first time author is, and what and then what kind of research you're talking about. And so if if you want to write a book about the best kind of nutritional regimen for avoiding cancer, and you are a an oncologist at Johns Hopkins University Hospital, I think the publisher can trust that you more or less know what you're talking about. If you're a schmo like me trying to write a book like that, you better have a lot of research ready to go before you approach your approach. And so I think it depends on who you are, and what you're what you're writing about. But don't discount again, I'm happy to be tactical here, Jay, don't discount the importance of researching the market. You know, I think what you have to do is you have to look at the market and say like what books, I mean, think of it as like a map, alright, what books are out there in this more or less similar space. But why is your is going to go to the spot that is unoccupied right now. And so you need to know, you need to know the market via either you need to know the market very well, you need to know you'd be able to talk about basically every book that's been written or as adjacent to your topic. And you need to know inside, you need to know that insight, you need to know that inside and out.


Jay Clouse 51:38

You're basically describing the book as a business in and of itself.


Dan Pink 51:42

Totally, yeah, because a book proposal is two things. One, as I mentioned before, it's a marketing. It's think of it as a it's a business plan for writing a book. All right, but it's also internally, it's also a test of whether you want to do this thing. In the same way a business plan is that way too. If you say, oh, I want to start up, I want to start a vegan pizza restaurant in Washington DC. Okay, that sounds cool. It's probably a pretty good idea. But until you write a business plan, saying, Okay, where do I get the ingredients? What's my budget gonna be like? How many people do I need to to hire for this? How much money do I need to raise to start this business? What portion of people in the Washington DC metropolitan area are vegans? Are there other vegan restaurants in this in this area? Have there been vegan restaurants tried in this and you know, like, that's a different kettle of fish there.


Jay Clouse 52:27

I love these tastes, because a lot of times when I ask these questions, the kind of trite advice I started to get is all that matters is now you're coming to a literary agent and you already have an audience. That's all they care about,


Dan Pink 52:39

then that's not insignificant. Okay. So I think that if you go to if you go to a litter, I think that again, I don't I again, I'm not trying to be pollyannish here. I think that matters. You know, I think if you have a built in audience, that's helpful. If you have a platform, that's super helpful. But you know, it's, it might be necessary, but it's certainly not sufficient. And in all cases, it's not totally totally, totally necessary. I don't I just, I think that that you got to get the substantive, deeper stuff, right. First, the other stuff is, I think those are in some ways, second order issues. If you start saying, I have a big platform, I should write a book, you're going to write a crappy book. If you say, I've got an idea for a book, I'm the perfect person to write it. It's going to be a great book, how can I build a platform to launch it? That's a better way to go.


Jay Clouse 53:36

I love it. Well, I'd like to wrap this up with just a quick simple question that I love asking people inside the world of authors. Is there a hunch that you have about where things are heading, but you don't have any data yet to support that hunch?


Dan Pink 53:51

Data free hunches are my specialty. So I would I have a hunch that books will get a little shorter. Because I think that attention spans are shrinking. That's always I think that's been a permanent state. I think they're shrinking and shrinking and shrinking. I think a lot of books are too long. So I think we'll get that I also feel like there is an opportunity out there for book for a quote unquote, book, beyond an ebook, to integrate other elements, other kinds of interactive elements into it that hasn't been fully realized yet, I certainly haven't done it. What's more is that I think that the world of audiobooks we're gonna look back at I'm gonna look back at some of the audiobooks that I've done myself, where I'm basically sitting in a studio and reading my written text aloud, and calling that an audio book. I think we're going to look at that as like a joke. And what we're going to see, I mean, some places I've got Pushkin's and a really good job of some of these things, is actually creating things precisely for the audio medium, that are not simply printed stuff that's read allowed. Those are my data free hunches.


Jay Clouse 55:09

If you want to learn more about Dan, you can visit his website at Dan pink.com. Links to that and a whole lot more are in the show notes. Thanks to Dan for being on the show. Thank you to Emily Klaus for making artwork this episode. Thanks for making time 100 Remix in the show and Brian skill for creating our music. If you like this episode, you can tweet at Jay Clouse and let me know and if you really want to say thank you, please, please, please, please leave a review on Apple podcasts or Spotify. Thanks for listening, and I'll talk to you next week.