Daniel Pink and Susan Cain on the Art of Writing
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Daniel Pink and Susan Cain on the Art of Writing

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Daniel Pink and Susan Cain on the Art of Writing

What do we lose when we avoid sorrow and chase empty delights, when we mask our pain and feign cheerfulness, when we profess to have no regrets and insist on turning every frown upside down? Those questions are at the heart of two new books by Next Big Idea Club curators Susan Cain (Bittersweet) and Daniel Pink (The Power of Regret). Today on the show, they sit down with Rufus to swap notes on the writing process, share what they’ve learned from each other, and imagine what the world might look like if we all learned how to embrace negative emotions.

Listen to their appearance on the Next Big Idea podcast below, or read a few key highlights. And follow host Rufus Griscom on LinkedIn for behind-the-scenes looks into the show.

Where book ideas come from.

Rufus Griscom: You both have wonderful new books out in recent months. From Dan, we have The Power of Regret: How Looking Backward Moves Us Forward. From Susan, we have Bittersweet: How Sorrow and Longing Make Us Whole. Let’s start with the topic of how you came up with the ideas for these books. Let’s start with you, Susan. You wrote the legendary book Quiet: The Power of Introverts in a World That Can’t Stop Talking. You and I met a few years after you published Quiet, and I remember you telling me that you had no plans to write another book. What changed your mind? 

Susan Cain: The way that I come up with topics for books is, like, I’m looking for something that has felt incredibly important and moving [to me] over time. When I look at both books, [Quiet and Bittersweet], I think of moments that stand out in my memory that I can’t let go for some reason.

Most of life you don’t actually remember. The moments that really stand out are the ones where you’re actually onto something. With Bittersweet, there’s the moment that I wrote about where all the way back in law school, when I was in my twenties, I was in my dorm room, and some friends were coming to pick me up so we could all go to class together. I was blasting out my usual minor-key music, mnd my friends thought that was hilarious. Why would anybody be listening to this on full blast? It was really just a nothing moment, except it stayed in my memory for years.

That experience—wondering what it was about that music that mattered so much, and what in our culture made that such a funny subject of a joke—I thought about it for decades after, and then it became this book. 

Daniel Pink: Did you have books post Quiet that you were contemplating, that you didn’t write, that you discarded, that you thought about doing but didn’t pursue? I’m always curious about that.

I’ve discarded so many book ideas over the years. I have a scrap heap of discarded book ideas.”

Susan: Oh, that’s a good question. I don’t know. I have a bunch of book ideas that are still sitting in a file that I might get to you one day. I didn’t have a book that I started working on and then discarded. Did that happen for you? 

Daniel: I’ve discarded so many book ideas over the years. I have a scrap heap of discarded book ideas. The reason I ask is that I’ve seen writers get trapped in this. Writing a book is such a gargantuan pain in the ass. I’ve seen writers get trapped in that they get seduced by something—a topic, an idea—early, and then they find themselves committed to writing a book, and then they realize, This is a colossal mistake. And so I’m always curious: How do writers figure out what makes the cut and what doesn’t make the cut?

Susan: Do I remember correctly that with The Power of Regret you were actually pretty far into another book and then you came across the idea of regret?

Daniel: I wasn’t very far along, but I was under contract. 

Before I do a book, I do a very long proposal. Even though it’s possible that you can get a decent contract, sometimes a very good contract, with two pages, I usually write 30- or 40-page proposals, partly as a test of my own interest in a topic, because for me a big fear that I have is being on the hook for writing a book I don’t want to write.

So what happened in this case, to answer Susan’s question, is that I had what I thought was a pretty good idea for a book, and I was working on it, and then I had a moment where I realized that I started thinking about this topic of regret. The catalyst was that my elder daughter graduated from college, and that marker in life was a wake-up. I looked back and realized that I had regrets. And when I started talking to people about my own regrets, I found that people reacted very robustly. That got me curious. So I put aside this other project and wrote an entirely new proposal.

On sharing your ideas with other people.

Rufus: To what extent do talk to friends and Uber drivers and cashiers? To what extent do you test these ideas when they emerge?

Susan: I actually don’t really talk to anybody about it because I don’t know if people always give the right feedback. If you’re moved by something that you feel very deeply, then you kind of know it. With the introversion book, a lot of people said to me at the time, “Well, that’s kind of like an odd-ball topic.” Before that, I had been spending all these years teaching negotiation skills to women, and people were like, “That’s the book you should do. You should write a book about negotiation. That’s a saleable topic.” And I was like, Oh, I don’t want to do that at all. So for me, it’s more like once I’m in the book, then I want to interview a thousand people about it and talk to people that way, but not so much as feedback about whether to do that book in the first place.

Daniel: I have a social view of writing. I actually am happy to talk about stuff I’m working on in advance. That’s in part because sometimes people give you useful reactions. It’s also important because talking about it is another way of figuring it out. Talking about it is different from figuring it out on the keyboard, and that’s a helpful exercise. 

I love getting feedback from readers afterward because I ended up thinking about things that I never thought about before. And I’m always surprised by what takes and what doesn’t. If I were to chart my predictions about what people would respond to deeply and what they would ignore in each book, I would be wrong every single time.

Talking about it is different from figuring it out on the keyboard, and that’s a helpful exercise.

One of the things that I do—it’s kind of interesting for prospective writers out there—is I always look at the Kindle versions of my books at the most underlined passages. That’s a way to see what is actually working. And when I look at that, I’m always surprised. Language and ideas that I spent months crafting? No one cares. A sentence that I wrote hung over one Tuesday morning in July? Everybody underlines.

The pleasures and perils of research.

Susan: Once I’m actually writing a book, I think I overdo it really [in terms of] how many people I talk to and how much research I do. It’s fantastic, and at the same time, it makes it really hard to figure out what goes in the book and what gets left on the cutting room floor, and then also how to structure it. How do you decide how many interviews to do, how much research to do? Do you feel that you end up with much more of a surplus than you needed? 

Daniel: Well, I think you have to have a surplus. I don’t think there’s a single heuristic to figure that out. You have to be willing to do way more than you need, and you have to be willing to do what you do in the service of readers, not in the service of yourself. Case in point: Two Julys ago, I spent the entire month reading 70 papers on how regret develops in the brain, especially among kids. And then, when I got to writing, I realized that I could pay basically describe it in—I think it ended up being like one and a half paragraphs. That’s annoying because I just squandered a month of my time now. So I face a choice. Do I try to somehow retrieve those sunk costs and say, “You know what, reader? I spent a frickin’ month on this. It was challenging, and it was hard, and time-consuming, and not that enjoyable. Therefore you are going to sit here and read seven pages about this”? Or I can say, “You know what, reader? I want to serve you. So the truth of the matter is that what you need to know in this context from this month of reading is really just one paragraph”? Do I want to inflict pain on the reader over seven pages, or do I want to inflict pain on myself for [wasting] an entire month? And I flipped a coin and said, “I’ll punish myself.”

Rufus: Very generous of you, Dan. Thank you for that.

Remember the wow.

Susan: I was going to share one thing for prospective writers. One thing that I do in sifting through all the material that I end up gathering—whether it’s interviews or people’s stories or research or whatever—is try to include the bits that I felt had emotional salience when I first discovered them. There are certain stories that I come across and I remember the emotion that I felt when I first heard the story. You might not feel that emotion after you’ve read it in your notes 17 times, but if I can remember that the first time I heard it, it blew me away, or that when I first heard a new piece of research, it was like, Wow! I didn’t know that was true. Later on you forget the wow, but you can remember that you first felt it. So I make a point of including those things. 

Daniel: That’s a great lesson. Remember the wow. I hadn’t thought about it that way. It’s super useful because you find this remarkable thing, and you’ve lived with it for a few months, and it’s like, Ah, whatever. Everybody knows that. Remember the wow.

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