Daniel Pink is one of the most successful nonfiction writers of the past 30 years. You've probably seen his books: Drive, The Power of Regret, or To Sell Is Human. Maybe you've even seen his viral TED Talk about the science of motivation.
In this conversation, we started by talking about his writing process, which he's been doing consistently for so many years. I wanted to know when, where, and how often he writes. I wanted to know all about it.
At the very end, Dan goes: "I've got one more thing to share with you." And what he shares is the most important question that any writer can ask before they take on a new project.
Transcript
00:01:54 Writing routine
00:06:41 Building a book structure
00:09:14 The benefits of taking breaks
00:14:12 How to choose your next book
00:17:46 Book proposals
00:21:51 Regrets
00:25:06 Why he became a writer
00:28:21 Research techniques
00:32:09 Writing plays
00:38:47 Writing lessons
00:43:38 What he got from Law School
00:46:36 Collecting great sentences
00:49:31 "What are you promising your reader?"
David (01:54-02:00):
Well, I think the place to begin is I just want to hear about when you sit down to write.
Daniel (02:00-02:00):
Yeah.
David (02:00-02:05):
There’s a certain sense of consistency, routine, ritual, that seems absolutely core to your process.
Daniel (02:06-02:34):
No question. When I have something to write, like when I’m working on a book or a long article, I have a structure, and I’m pretty rigid. I show up in my office at a certain time, I give myself a word count, and I don’t do anything until I reach that word count. I do it the next day, and the next day, and the next day. Otherwise, there’s no way I would have been able to. I came to that the hard way, struggling to write stuff, and certainly struggling to write my first book.
David (02:35-02:38):
So walk me through that. It’s like 800 words. You wake up.
Daniel (02:38-02:58):
It depends. Here are the details. I wake up, I have a cup of coffee, maybe a little breakfast, and maybe look at the newspaper. I actually still get print newspapers. I’m going to be the last person to give them up.
David (02:58-03:00):
Daniel Pink, Washington Post.
Daniel (03:00-03:55):
I don’t get the Washington Post anymore because I’m annoyed with them. But I get the New York Times and the Wall Street Journal. I look at those, and then I go to my office. My office is the garage behind my house. I go out my back door, 22 steps to the refurbished garage behind my house, and I sit at my desk. I have a certain word count for that day.
For me, because I’m a pretty slow writer, it’s often not a very high word count. Sometimes it’s 500 words, sometimes it’s 700 words, 800 words is hard for me. Writing is still really hard for me, even though I’ve been doing it my whole life.
I have that word count, and I don’t bring my phone with me into the office. I don’t open up email. I don’t do anything like that. I just crank until I hit that word count. Then there’s a moment of liberation where I’m like, “Oh, I’ve done it.” Then I can watch some sports highlights, check my email, or do other things. Then I do it the next day, and the next day, and the next.
David (03:55-04:04):
Next day, and the next day. You would do that for a certain number of days until you reach, say, 80,000 words. Then what do you do? You begin the editing phase. How does that work?
Daniel (04:04-04:35):
For a book, I work on a chapter at a time to make sure that I get the chapter right. I do that for several weeks to get the chapter done. Then I spend another week editing and rewriting.
For me, and I think for a lot of writers, the routine and the rigidity is actually really important. The structure itself is liberating.
David (04:35-04:49):
Right. I feel like there’s two kinds of writers. There are writers who are like, “No, I never talk about my writing before I publish it,” and then there are people who are like, “Yeah, I’ll talk about it because talking about it helps me structure the ideas and form the ideas.” You seem to be in the second camp, huh?
Daniel (04:49-05:41):
I am the executive vice president of the second camp. I want to be president, but I’m waiting for the president to leave.
Absolutely. For me, it’s really important to socialize ideas. When I have something that I’m working on, I like to talk about it because I want to see how people react. Are they dead in the eyes? Are they asking me questions? Are they intrigued? If I say something, do they say, “Oh, that’s interesting?” Do they say, “That’s interesting? Have you thought about this?” Do they say, “That’s interesting? I disagree with you?” That’s really helpful to me.
I also find that I work things out sometimes by talking about it, which is nothing new.
David (05:41-05:42):
It’s kind of a weird thing, right?
Daniel (05:42-05:43):
You’ll be blocked when you’re trying to.
David (05:43-05:52):
Think about it on your own, and then, all of a sudden, you explain it to somebody else. It’s like your brain automatically structures it and makes sense of things. It’s like, “Okay, I need to do more of this, less of that.”
Daniel (05:52-06:41):
That’s important to me. The way I approach things is 360, almost literally in the way my body is in my office. Especially for books, the structure is really important. I can’t write a book unless I see at least the skeleton of it.
I’ll spend months doing research and reporting to try to find the structure. I will often put either a whiteboard or big Post-its with my first kind of scratchings about what that structure might be. I will literally turn in my swivel chair—here’s my desk—and behind me, I’ll have Post-its. I’ll sit there and just look at that to try to get the structure because I can’t really write anything until I see the structure of the building.
David (06:41-06:49):
Walk me through a specific book where the amorphous lack of structure began and then where you ended up.
Daniel (06:49-08:28):
Okay, let’s take the book about the science of timing. I had all this research. I went through something like 600 studies because I realized that what was happening with timing is that you had these different disciplines that were all asking similar questions.
They were asking similar questions in economics, neuroscience, and even medicine: How do we make different decisions at different times of day? How do beginnings affect us? How do midpoints affect us? I had this whole melange of studies. Initially, I started organizing it like day, week, month, year. That was going to be the organizing principle, but it just didn’t work. I would stare at it and stare at it and say, “I have nothing to say.”
Then I started thinking about it in domains: timing at school, timing at work, timing in health, timing in leadership. I tried that, stared at that on the wall, but that didn’t work either. Finally, through some conversations, I said, “Well, maybe I just need to do it more conceptually.” I thought, “Okay, what if I do timing in a day?” Then I started thinking about something about beginnings, midpoints, and endings, that the domain itself was less important than the fact that beginnings operate on us one way and midpoints operate on us another way. It wasn’t so much the week that was significant there, but the midpoint.
David (08:28-08:29):
Right?
Daniel (08:29-09:05):
Over time, in this tortured, unpleasant way, I kind of came to that way of organizing it, put it there, and said, “Okay, now I can begin writing.”
The structure doesn’t always stay the same. You have to stress test it with what you’re writing. For instance, I started writing a chapter about the day, and I realized I was going to have a little section about breaks, the importance of breaks. I had this whole pile of research about breaks. I started writing and I thought, “Whoa, there’s a lot to say about breaks. There’s a shitload to say about breaks.” Suddenly I discovered, “Oh, I have a chapter on breaks.”
David (09:05-09:06):
So that.
Daniel (09:06-09:14):
That’s what it is. I’m not sure how interesting it is to anybody else, but it’s sort of the tortured process that I go through.
David (09:14-09:17):
What’s important to know about breaks for writers?
Daniel (09:17-10:00):
Oh, lots of stuff. Well, for writers and for everybody. Writers and others need to think about breaks the way that athletes think about breaks, which is that they’re part of our performance, not a deviation from the performance.
A lot of times we say, “Oh, I’m taking a break. God, I’m kind of wimping out here. I need a break. I’m overworked,” when in fact, breaks and recovery are fundamental to our performance. We know a lot about effective breaks, and there’s a kind of platonic ideal of effective breaks. We know from the science that breaks when you’re in motion are more restorative than breaks when you’re sedentary.
David (10:01-10:04):
So a break when you’re in motion, like going for a walk rather than sitting down.
Daniel (10:04-10:04):
Absolutely.
David (10:04-10:05):
Got it.
Daniel (10:06-10:42):
Being in motion is better than being sedentary. Being outside is better than being inside. There’s some incredible stuff on the importance of being in nature, just in general, but for breaks, being outside is more effective than being inside.
For writers, a little bit counterintuitive, but breaks with other people are more restorative than breaks on your own. This is true even for introverts. It’s important that breaks are fully detached. If you go off for your walk and stare at your phone, that’s not a break. We know a lot about how to take effective breaks, and we have to start thinking about breaks in a fundamentally different way.
David (10:42-10:57):
It’s funny that you’re talking about how you like talking ideas out, and you like seeing people’s reactions. It seems to be how you learned to give good speeches by looking at the audience, not the presenter.
Daniel (10:58-11:36):
Oh, yeah. When you’re giving a speech, you see the audience, you’re getting feedback in real time. Are they laughing at the joke? Are they not laughing at the joke? Are they staring at their phone? Are they talking to their neighbor? Are they spacing out?
When I watch other people give speeches, I will position myself in a way that I can see both. I want to see what the speaker is doing, but I also want to see how the audience is doing. This is especially true if I’m speaking at an event at 3:00, and I’m there at 11:00. I want to gauge the audience. What kind of audience is this? How receptive are they? What are they into?
David (11:36-12:02):
We were talking about David Zucker earlier and how, when he was developing movies like Airplane and Naked Gun, he would host screenings and pay attention to when there were laughs.
If there were more than 25 or 30 seconds of no laughter, they would say, “Hey, we need to focus on minute 47.” That’s why their movies are joke after joke after joke.
Daniel (12:04-14:11):
I do that. I don’t do that many speeches that are written out. A commencement speech is something that I will write out entirely. But when I do a speech like that, I will go through afterward and put an “L” circle for when there are laughs, just to see the pace of laughs.
In certain kinds of speeches, you don’t want it to be too concentrated in one place because then it’s like, “Wait, is this guy doing a stand-up routine or is he telling us something?” Also, if there are long patches without a laugh, that can sometimes feel dutiful to people.
I’ve started writing plays, and I’m discovering they’re comedies. I thought they were dramas at first, but when we did a table read with actors, they were like, “You moron, this is a comedy. Why are you calling this a drama?”
So I actually went through and did an analysis of the laugh density of the plays to see if they’re moving. In one of the plays, there was a long stretch where there was so much plot unfolding that there weren’t any laughs. I said, “Okay, wait a second, the audience is going to get confused here. They’ve been laughing at a regular pace for the first four scenes, and suddenly, the fifth scene has no laughs. I gotta up that.”
My view is that writing is engineering. It’s an act of engineering in the sense that you’re building something that has to work. It’s less a classically artistic thing. You’re building something that has to work, and you’re testing it and stress-testing it, seeing if the walls are strong enough to support the roof.
David (14:12-14:27):
Walk me through how you go from, “I got an inclination here,” to, “I’m going to do this book. I’m going to spend the next few years committing to it.”
Daniel (14:27-17:00):
It’s a big commitment, and I think a mistake that some authors make is they become enamored with something, or something they write becomes very popular, and the world starts pushing them in this direction, and it might not be a good idea for them.
I start with a massive list of ideas that I keep in my very sophisticated knowledge management software called Word. I revisit those periodically just to see. Sometimes I come back four months later and say, “Oh my God, that’s so stupid.” Other times, certain ideas will stick.
Then I’ll start collecting some articles about it and reading some things about it. For instance, I’ve been contemplating writing a book about wisdom. That’s an idea I’ve had for a while, and it’s stuck around, so I might end up doing that.
If I were to pursue that, I would then start reading some more about it, talking to people about it, socializing the idea. I always write very long book proposals, maybe 30 or 40 pages. The reason I write them is that it’s a test of the idea. If this idea can’t withstand a 30-page proposal, it’s not going to be able to withstand a 300-page book. It also forces me to think about whether there is a there there.
It’s a test of me as well. Do I like writing this 30-page proposal? If I hate writing a 30-page proposal, I’m going to really hate writing a 300-page book.
I have book proposals that I’ve never submitted. Years ago, I had this idea for a book that I thought was so freaking brilliant. The title was “The Invisible Present,” basically things out there in the world that are happening right now that nobody can see. It was a list of like 10 things kind of like in the tradition of megatrends. There was a play on words because the present is also like a gift.
David (17:00-17:02):
Yeah, that’s a little too clever by half.
Daniel (17:02-17:46):
But I wasn’t getting any attraction on it at the time. My wife and I had little kids, so I sent them away to visit my in-laws. I was going to go into my office and hole up and just crank out this proposal.
A week goes by, and I’m cranking on this. Ten days in, they were going to go for two weeks, I call my wife and say, “You guys can come home now because this is not a book. This is just not going to work.”
I’d much rather find that out after 10 days than after signing a contract.
David (17:46-17:56):
Can you walk me through the structure of a book proposal? What is my outline?
Daniel (17:56-19:54):
It depends. The most important thing in a book proposal is being able to clearly articulate what the idea is and why it is totally fresh, but also totally familiar. What you want is that combination.
Basically, the great pitch for the timing book was: “We have lots of ‘how-to’ books. We need a ‘when-to’ book.” That’s fresh, but it’s also familiar.
The idea itself is really important. I think establishing why you are the best person to write it—first of all, establishing why no one else has written it and why you are not only the best person to write it, but the only human being on God’s green earth who could possibly write it. Ah, the anointed one.
Then figuring out who the audience is. This is actually really important, being able to clearly articulate who the audience is. Many writers delude themselves into thinking their audience is everybody, and it’s never everybody.
Being able to articulate that and then giving a sense of what the structure of the book might be and also kind of what it contributes to the world. There’s a reason why nobody has written this and why you need it now. The “nowness” is really important. Why does this book meet the moment? Why is it the right book for the right time? There are plenty of good books that are in the wrong time.
I think publishers tend to like the story of how it came to you. For timing, it was like, “I realized that I was making all kinds of timing decisions myself.” For the book about sales, “To Sell Is Human,” it was me coming to this idea. “God dang it, I am just selling all the time.”
David (19:54-19:54):
Right?
Daniel (19:54-19:56):
Like, and I don’t know what I’m doing.
David (19:56-19:56):
Right.
Daniel (19:56-21:03):
For the book about regret, I was actually working on an entirely different book at the time. I went to my daughter’s college graduation and basically had a kind of crisis of sorts—a mild crisis—where I had an out-of-body experience. I just couldn’t believe this kid was graduating from college because she was just born. And I couldn’t believe I was old enough to have a kid graduating from college. I started thinking about my own regrets about college, which were not many, but there were some. I wish I had worked harder; I wish I had been kinder. It really stuck with me.
There’s a marker in your life when you have a kid graduates from college. Because, to your earlier point, I like socializing ideas. I told some of my friends, “Something about my regrets sort of bums me out.” I did it with some trepidation because I knew nobody wanted to talk about regret. I mentioned it very sheepishly and then I discovered that everybody wanted to talk about it. Once I divulged it, other people divulged it.
David (21:03-21:16):
Well, also, in the way that you frame the book, a lot of people are interested in this. Regret is a topic that a lot of people want to talk about, but we talk about it like that, and there’s an opportunity to talk about it like this. That’s an important part.
Daniel (21:16-21:50):
That was it. I was working on book A, and my publisher had no idea that I was going through this dull midlife crisis about regret. I started looking at the research on regret and saying, “Wow, there’s actually a fair amount here. It’s actually pretty interesting. It’s multidisciplinary, which I like.”
I wrote an entirely new proposal. This editor, who thought they were going to get a couple of chapters, gets an email from me with a proposal for an entirely different book.
David (21:51-21:52):
Well, what’d you learn about regret?
Daniel (21:52-21:54):
Like, what sticks out to you now?
Daniel (21:54-22:00):
Everybody has regrets. It’s one of the most common emotions that human beings have.
David (22:00-22:01):
Yeah, people are like, no regrets.
Daniel (22:01-23:16):
I definitely have a few regrets. The first chapter of the book is called “The Life-Changing Nonsense of No Regrets.” It’s an act.
It’s one of the most ubiquitous experiences that humans have, and it can also be one of the most useful if we treat it right. We have piles of evidence showing that it’s a transformative emotion for everything from negotiation to problem-solving to finding meaning in life.
The problem, the mistake that we’ve made—and it’s an American mistake—is that we have been taught and kind of indoctrinated to think that we should always be positive and never be negative, to always look forward and never look back. That’s just bad advice.
We should be positive most of the time. Positive emotions are great, but we want some negative emotions because they’re instructive. We should look backwards sometimes because we can learn from looking backward.
We’ve been taught to ignore your regrets. Terrible idea. When that doesn’t work, people end up wallowing in their regrets, which is a worse idea. What we should be doing is confronting our regrets, looking them in the eye, using them as information, using as data. When we do that, we have piles of evidence showing that it’s a very helpful emotion.
David (23:16-23:24):
You had just said that you like when the source material for a book is interdisciplinary. Why is that?
Daniel (23:25-24:48):
The advantage of being a generalist is that you have different domains of research often asking very similar questions that never talk to each other. There’s no consilience. What they’re finding is, in some ways, very consistent with each other. It’s in harmony with each other, but there isn’t a place in the academy that puts it all together.
It relies on generalists to come in and say, “Hey, you realize that what the chronobiologists are finding about wakefulness cycles is also what the judgment and decision-making scholars are finding about choices, and also what the sports psychologists are finding about athletic performance?” You know, it’s like, “You guys should really meet,” but they don’t because they’re all in their world. Developmental psychologists don’t talk to cognitive psychologists. They don’t talk to social psychologists, let alone economists, let alone people doing research in anesthesiology. Someone who can come in unearths things that are true and meaningful to people.
David (24:49-24:52):
Well, yeah. You describe yourself as a translator.
Daniel (24:52-25:06):
Academics are often speaking to highly specialized audiences, and they often speak in their own coded vernacular. If you can be bilingual, that can be helpful.
David (25:06-25:08):
Why did you choose to become a writer?
Daniel (25:11-26:33):
In my never-ending quest to hand out life lessons to the youngsters out there, what happened to me was this. I’ll try to be brief. I went to law school, not thinking that I would be a writer, although I had some inklings. I never set out to be a writer. I went to law school because it was something to fall back on and because I was interested in politics.
What I found in working in politics is that I was writing articles on the side. I had some pretty demanding jobs, and yet I would be writing articles on the side. In law school, I was writing op-eds for the Hartford Courant about things unrelated to law. When I was in college, I was a linguistics major, a quasi-cognitive science major, and yet I was also writing short stories sort of like a hobby. Like some people play golf, this is this thing that I do that’s kind of fun. I realized as I got older that this thing I was doing on the side was actually what I should be doing.
David (26:33-26:34):
That’s the main event.
Daniel (26:34-27:55):
Yeah, it was telling me what I should be doing. I think you’re constituted to be a writer. If you are working in these demanding jobs in politics and you are at 11:30 at midnight writing an article for George magazine, which was John F. Kennedy Jr’s political magazine in the 1990s, for free because you can’t take any money because you’re a government employee, that’s a pretty strong signal about what it is you do.
I’m not saying I’m going to be a writer. It’s like, “Wow, step outside yourself and watch what you do. Dude, I think that you’re a writer. I don’t think you’re a political person; I think that you’re a writer.” Working in politics, it was pretty clear to me after several years that that was not what I wanted to do with the rest of my life, and I was more inclined to do what I was doing on the side, which is come up with my own ideas, work by myself, and work for myself. I discovered that that’s who I was rather than having a clear intention and a goal and setting out to execute against that.
David (27:55-28:03):
It seems like when I think of your process, when I think of your approach, one of the core things to understand is you say, “Read slowly, you write slowly.”
Daniel (28:03-28:04):
I’m very slow.
David (28:04-28:08):
So then there’s a certain consistency rather than intensity that’s demanded from this.
Daniel (28:11-28:13):
The tortoise won, let’s just put it that way.
David (28:13-28:14):
Uhhuh.
Daniel (28:14-28:15):
Okay.
David (28:15-28:16):
Right.
Daniel (28:16-28:20):
I’m a tortoise, not a hare. It takes me a long time to do stuff.
David (28:21-28:31):
Okay, so talk me through the research. How do you research in a way that’s rigorous without getting distracted and lost in it?
Daniel (28:31-29:42):
You can get distracted and lost in it; there’s no question about that. There’s a moment, especially when you’re looking at academic research, where you feel like, “Okay, I’ve heard this before.” And that’s when you stop.
In the Regret book, you also have to be rigorous about what you include. I spent probably three or four weeks looking at the research on how regret develops in children: when do children learn what regret is and when do children learn counterfactual thinking? I had piles of that research, and I learned a lot about the child development of how children’s brains change in order to experience regrets. The audience needed a paragraph on that; they didn’t need any more.
David (29:42-29:43):
This time on this.
Daniel (29:43-30:07):
You have to know what to include and what not to include. You also have to triangulate about what’s credible. If I see one paper from an obscure journal that says that wearing green socks makes you more creative, that’s awesome. What a great takeaway! But if it’s the only paper on green socks and creativity, then I’m a little bit more skeptical about it.
David (30:07-30:09):
We all know it’s yellow socks, right?
Daniel (30:09-30:54):
When you look at the research about the importance of being in nature and what that does for well-being, there’s something there. Even the research on walking is unbelievable.
There’s a famous study where they put people in a chair and people on a treadmill in a laboratory. They used the alternative uses for object tests, where you give somebody something mundane, like a brick, and ask how many different uses they can come up with for it. It’s a test of creativity. You can use it as a doorstop, a step ladder to reach something, or a paperweight.
David (30:54-30:55):
You can’t.
Daniel (30:55-31:07):
You can’t reach something. So you generate alternatives. It’s a measure of creativity. The people who were walking on a treadmill generated three times as many ideas as the people sitting in a chair.
David (31:07-31:07):
Wow.
Daniel (31:07-31:19):
It’s unbelievable that they were just on a treadmill in a laboratory. All of which is to say that there are some things where the evidence is coming from different disciplines, saying something that rhymes with each other, and you end up using that.
Daniel (31:20-31:22):
The biggest lie that writers will tell.
David (31:22-31:24):
Themselves is, I’ll remember that later.
Daniel (31:24-32:08):
There are so many times when I’m listening to a podcast and want to save something, but I never end up saving it because typing it into the phone is too much work. I found a great solution to that problem called Podcast Magic, the sponsor of this episode.
It’s super easy. Say you’re listening on Apple or Spotify. If you find a bit in this conversation that you really like, just take a screenshot of it and email it to podcastmagic@ublime.app. A minute later, you’ll get an email back with the transcript, the context, and all the information that you need. That way, you don’t need to write down all the information. So if you find something in the conversation that you really like, check out Podcast Magic. All right, let’s get to the interview.
David (32:09-32:11):
What’s drawn you to plays?
Daniel (32:12-32:32):
I’ve always been a huge fan of going to plays. There’s something about live theater, especially now, where it’s one of the only places where people turn off their phones. Even in movie theaters, people still have their phones.
David (32:32-32:36):
I was at the movies the other night, and a woman was texting on her own half the play or half the theater.
Daniel (32:36-32:43):
Yeah, and in plays, that is absolutely verboten. These theater people will come and kick your ass.
David (32:43-32:47):
They come in with flashlights and shame you.
Daniel (32:47-33:43):
So, there’s a social norm of no phones, which is incredibly important. You are having an experience watching actual people up there. Not only do you not have your phone, but you’re also not watching a screen. So much of our lives are spent looking at screens. A stage is not a screen. A stage is real people up there.
You have this experience where you are with other human beings, looking at other human beings in a particular moment that’s not going to last for very long. That is transcendent. It always has been. That’s why theater has been around for so long. To me, it is urgent in this moment. And I also wanted a new creative challenge. Writing plays is very different from writing books.
David (33:43-33:46):
Do you feel like you operate with the same engineering mindset?
Daniel (33:48-34:28):
Yes, but I’m engineering a different product.
Plays, you know, someone who writes plays is a playwright. So there’s already built into that is the idea that you are making something.
Writing a book is like building a house. It has to stand up. There are different kinds of rooms that have to have some flow to them. You can build a beautiful house and then look at it afterward and say...
David (34:28-34:29):
Ah.
Daniel (34:31-35:15):
The powder room probably should have been here, but it’s still a great house. People want to buy it. It’s a great house to live in. You see a few things here and there that you might want to change. That’s building a house.
Writing a play is like building a watch. If the gears don’t click, it just isn’t going to work. There’s very little margin for error because you’re dealing with such a compression of narrative, storytelling, and character. If the gears don’t mesh perfectly, it’s not going to tell time.
So, yes, it’s engineering, but you’re engineering something very different.
David (35:16-35:21):
What kind of plays do you like to watch? And how has that made its way into the kind of play that?
Daniel (35:21-36:47):
You’re right. I write the kind of books that I would want to read. One of my criteria for writing a book is: if someone else had written this book, would I want to read it the first week? If the answer is no, then it’s probably not a book I should write.
With plays, I like musicals, but I don’t write musicals. I like plays about contemporary people, or mostly contemporary people, in challenging situations that give us something about what it means to be a human being on this planet.
What I like about plays is the compression. Often there are just a couple of people on stage, and the whole audience is locked in on that. You have to make that moment work. There’s no breathing room. You can’t pan out. You can’t change the set, or do some of the things that you can do in a book. You’re stuck with those two people on stage doing things. It has to have versimilitude. It has to sound like people really talk. But if you listen to a transcript of people actually talking, that’s totally boring.
David (36:48-37:03):
So is the process of writing the play the same because it’s a narrative? I’ll throw something at you that’s intentionally provocative: It’s a narrative; you need more space to get into the narrative. So the writing sessions need to be longer because of that?
Daniel (37:04-37:04):
Yes and no.
David (37:04-37:05):
Yes.
Daniel (37:05-38:47):
I’ve tried it both ways. Even novelists have different ways. Some novelists outline everything; some just go with the flow.
I’ve tried going with the flow, and I’ve tried outlining everything. With the books, I’ve settled in the middle where I need a sense of where things are going. I’m absolutely ready to go off on a detour and arrive at a different destination, but I need to know what that destination is.
The other thing about plays is that it’s a collaborative medium. Books are much less collaborative. With a book, the idea in my head hits the paper, and then it goes into your head. That’s the transmission process.
With a play, the idea in my head goes on paper, then it gets handed to a bunch of other people who do stuff with it, and then it goes into your head. How you cast a play, how talented the actors are, what an actor will bring to it… I’ve learned so much from actors. We’ve done table reads of two of my plays, and I learned so much from actors saying, “Hey, this doesn’t make sense to me. Why is this person doing this now?” I don’t know.
It just comes alive in a different way. Inevitably, it sounds different when actors are performing it than it sounded in your head. Ideally, it sounds better, because they’re actually elevating it.
David (38:47-39:02):
If you were to go back to Yale, go back to school, and give a seminar on what you’ve learned about writing, how would you structure that curriculum, that semester? What are the things that you would tell people?
Daniel (39:04-39:17):
I would start with what you ingest. What do you take in? What do you read?
David (39:17-39:18):
It starts with consumption.
Daniel (39:18-43:36):
Absolutely. Are you consuming with quality, and are you consuming with breadth? I think that would be important.
The other thing is I would recommend starting with shorter form before going to longer form to get your reps. I could do the semester-long seminar in ten minutes by saying read a lot and get your reps; you’d basically cover 80% of it. I’m a big believer in getting reps in everything. The best thing you can do as a young writer is write a lot.
Write a lot and also get a sense of what quality is. Get a sense of how you form your taste. If you can have people give you good, hard, smart feedback, that’s difficult, I feel like that’s rare. So you have to begin over time developing your own taste, knowing what’s good and what’s not good.
I took some courses in college specifically about writing. They weren’t literature courses; they were about writing. I took three really fantastic courses. One was basically writing poetry, writing the essay, writing short stories. There were three seminar classes. There were probably eleven students and one instructor. In the writing poetry class, you would read poetry and then write it and present it to everybody.
The professor basically said I was pretty good at the analysis of poetry because I’m a good text reader, but he also said, “I’ll give you an A minus if you promise never to write poetry again.” You should write a poem in your play, though.
The short story class was really helpful in learning in an early way about showing rather than telling. There’s a tendency among people who are pretty good at school to get pretty good at telling people stuff and less good at showing people stuff.
But the transformative one for me was this course on writing the essay with a professor named Charlie Yarnoff. At one point, I had this essay, and I was struggling; I couldn’t get it right. I went in to talk to him about it because it was pretty hands-on. I came in with an engineering mindset of like thirteen fixes that I could do: move the section over here, do this over here. He said, “Dude, chill out for a second. You don’t know what you think.” He said to me, this is 40 years ago, “Sometimes you have to write to figure it out.”
It was different from everything else that I had learned in school at that point, which is basically, you have an idea, you have a thesis, you have an outline, and then you write. But for me, I often have to write to figure it out. It was like, oh, my God, you’re allowed to do that.
I had this one thing in college, out of all things, an ethics class. We had to write an essay, and I don’t know what happened. I waited until the last minute, and I ended up writing an essay saying the opposite of what I believed. Like, my, like, you got to take a stand on something.
But the thing is, what I probably believe was that in writing it, I figured out that I believe something different. I always felt sort of ashamed about that. It’s like, oh, my God, I can’t believe I just did this. I basically wrote something that I don’t agree with, but I actually did agree with it because I was writing to figure it out. The idea of writing to figure things out is one of the great joys of writing.
David (43:36-43:49):
Yeah, I was talking to Tyler Cowan once, and we were talking about how to think better. He said one of the best things that you can do is write the most compelling argument you can for something you vehemently disagree with.
Daniel (43:49-43:50):
Okay, that’s good.
David (43:50-43:51):
And that stuck with me.
Daniel (43:51-43:52):
You know what?
David (43:52-43:54):
I have to say, that’s a hell of an exercise.
Daniel (43:55-44:38):
You know what? As I mentioned, I did go to law school, and professionally, there’s not a huge amount that I got out of it except that one of the things that lawyers do and one of the things that law school teaches you to do is take both sides of an argument, and that is really important.
That might be the most useful thing I learned in law school: the skill of taking both sides of the argument. If you do something like a moot court on a constitutional issue, there’s a coin flip. You’re on this side, you’re on that side. It’s like, okay, I can make that argument. Also, if you’re anticipating the other side’s argument, I think that’s a really valuable skill.
David (44:38-45:40):
Yeah. We were talking about taste earlier on, and you had me thinking about how you develop taste. One of the best things I’ve learned is ones and tens.
Think about books you’ve read, movies that you’ve watched, art that you’ve seen. Art that you’ve seen is a really good example because when you walk into an art museum, you go to the Met, there’s this weird cultural idea that everything in the Met is incredible. This is the paragon of quality for Western civilization in this building.
All this is to say that what ends up happening is most people walk around with this sort of dulled sense of, “Oh, yeah, it’s pretty good. Oh, yeah, it’s pretty good,” like we’re some sort of French art connoisseur. Whereas, actually, I think the best thing you can do when you’re in an art museum is think about what you love, but also if there is anything that you despised, anything that you loathed. When you force yourself to reflect on not just what you love, but also what did you hate, the process of doing that consciously develops a sense of discernment. Discernment is the thing that’s upstream of taste.
Daniel (45:40-46:36):
I agree with you. The other thing about art and writing is that to appreciate visual art, you have to know something about art history. The picture on the wall didn’t just emerge; it stands on the shoulders of other things and was followed by other things. That helps you learn. People who are experts in their fields know a lot about the field.
A classic example is Mike Tyson, who is an encyclopedia of boxing history because he loves boxing. So, if you’re a writer, you should know a lot about writing and writers. I think that’s a way to develop taste: have respect for the profession you’re in.
David (46:36-47:25):
There really is a certain accumulation of quantity that you need in any field. Danny Meyer, before he started Union Square Cafe and Shake Shack, talks about how he would just travel and go to restaurants. A few things stuck out to me.
The first was I had this balsamic vinegar in Parma, Italy, and I didn’t know balsamic could taste like that. It wasn’t on my map of reality. I didn’t know that existed. I think there’s a sense of “Wow, I didn’t know it could be so good” in a lot of places. Also for writers, this sense of “Wow, I didn’t know that you could approach the craft that way. I didn’t know that you could structure it like that. I didn’t know that you could use that sentence format.”
Daniel (47:25-47:25):
Right.
David (47:25-47:26):
I’m gonna try that.
Daniel (47:26-47:35):
How do you collect examples of good writing as a writer and writing teacher? Do you have a systematic way to do that?
David (47:35-47:41):
I just dump them all in a giant sheet. I have fun paragraphs and good introductions, and I just put them in both of those places.
Daniel (47:41-47:44):
Exactly. Do you keep a commonplace book?
David (47:45-48:10):
Not in the technical definition, but I just have two notes, and I dump so many things in there. If my writing feels dull, I’ll read those and try to pattern-match one of those paragraphs, this style. It’s like a menu of different voices and things that I can do.
Daniel (48:10-49:24):
I’ve been keeping a commonplace book for eight years where every day I write down one kind of sentence, phrase, or paragraph that speaks to me. I write down words that I didn’t know the definition of.
I never heard the word “castocracy.” It’s ruled by the least competent, least desirable people, ruled by the worst. That’s a useful word for a moment.
The act of writing it is basically, if you have a mechanism like a commonplace book, the artifact is valuable because you’re collecting stuff. It also changes the way you see the world. It changes your attention.
I saw this play, the contemporary version of Oedipus, pronounced “Edipus.” He’s running for office and saying that the current situation is messed up. He says, “The water got poisoned, and we got used to the taste.”
David (49:24-49:25):
That’s a hell of a line.
Daniel (49:25-49:30):
Indeed. If you’ve got 3,000 of those and you’re paying attention to them...
David (49:31-49:44):
As we begin to close, when you’re thinking of your writing and how you’re going to frame it, what you’re going to focus on before you start writing, what do you really value?
Daniel (49:45-51:57):
One of the things I think about is a single question: What is the promise I’m making to the reader?
If you think about writing and reading as a transaction, if someone buys one of my books, that’s incredible because that’s $25 they haven’t spent on something else. There’s an opportunity cost.
Even more, if they spend nine hours reading my book, that’s nine hours they’re not spending exercising, being with loved ones, or cooking dinner. That’s an incredible gift to me, so I feel like I have to pay that off.
I want people to say at the end, “Wow, that was worth more than $25,” or, “That was nine hours incredibly well spent. I’m glad I didn’t hang out with my kids during those nine hours. I’m glad I didn’t go out for a walk with my loved ones during that time.”
I have to make a very clear promise to the reader that you’re going to get something entertaining, diverting, and useful, something that will allow you to see your world differently and do things in a different way.
As a nonfiction writer, I think one of the most important qualities is not only being interesting, smart, and entertaining, but also being useful. You win when people not only think differently but also do different things. That’s what I want to try to do. That’s what I’ve been trying to do for 20 years with my books.
Even in terms of playwriting, I want people to maybe think differently and say, “I’m going to approach my kids a little differently. I’m going to approach my coworkers a little differently.”
The promise I’m making in anything I write is that the precious time you’re giving me will be really valuable to you. I want you to know exactly what I’m promising, and I want to pay it off because you’re doing me this incredible honor of spending time inside my head.
David (51:57-52:00):
It’s great to meet you.
Daniel (52:00-52:00):
Yeah.
David (52:00-52:02):
Thanks for coming on the show.
