Profession: Author, most recently The Inevitable

Favorite tools: Evernote, Scrivener, Gregorian chants

Writing time: After dark

Workspace: studio in Pacifica, California

You’ve always been a cataloguer of useful tools — from The Whole Earth Catalog to Cool Tools to Recommendo. What tools are you using now to research and write?

A lot of my reading these days is on the Web, and I use Evernote as a tool to capture that, so I can go back and it’s basically a smaller search pool to look through. For larger projects I use Scrivener to organize; I’m a very organic person — I’m not the sort of person who can outline books before they start. I’m somebody who doesn’t know what the book is about until the book is done. And so I’m constantly changing, and moving stuff around, so having that flexibility is key.

I’m finding now with some of my books — like the one I’m writing now — that there are so many parts that I’m constantly shifting around, that I just can’t keep it straight in my head, so that outline view in Scrivener is really essential. I just couldn’t do it in Word.

No, you can’t. And by the way, structure is the main thing in writing, and in editing. You want it to be invisible to the reader, but it should be felt by the reader. So anything that can make that structure visible while you’re writing is helpful.

Do you have routines that you follow when you write?

With writing, there’s a point for me that’s really hard. That usually comes for me on the first draft. I’m not a natural writer. I’ve worked with natural writers — they’re people who have to write every day; they love the act of writing; they’re happiest when they’re writing. I’m not. I’m a grumpy writer. I do it under duress. I don’t enjoy writing; I enjoy having written. So that first draft for me is the hardest because the kind of writing I do — it’s a kind of thinking. I write primarily to find out what I’ve been thinking, and I don’t know until I write it. And so it’s a very difficult process. And in those periods, which are messy and horrible, one of the things I do is I play the same song on loop, again and again. And it turns out from Tim Ferris’ crowd, this is not unusual for a number of different writers.

Really? And it’s a different song on loop each time?

No, it’s the same song!

Is it like a mantra? Can you not tell us what it is?

It is like a manta, but I can tell you what it is. It’s some Soviet-men’s choir doing a Gregorian chant. And there’s something about it that just settles me. It is like a mantra. The vibrations just settle me in, and I zone everything out. And I play it on loop. It just goes around for hours — the same song. (Laughs)

Surely you could get Eno to do a version for you that would just vary a little bit.

And this thing of playing on a loop, or having a playlist, is very common: Ernest Cline, Rob Reid both do this. Sometime they’ll have a new playlist for each book. And it then becomes a kind of white noise theme song for that book. And the other thing about it is when you hear that music, you start to write. You come to associate it with writing, and so when you hear it, you go into that state.

So it’s really bad for you when you’re on the highway and those Gregorian chants come on.

Yes! But that would be impossible, because they’d never play that on the radio.

Something I’ve done a little, but not a lot, but that Stewart Brand has done a lot of: when you get to the end, the final thing, you read it out loud. That’s a level of polish that you may or may not want to do — because it really reveals a lot of cracks. And the cracks come from overcomplications. If you’re having trouble reading it, you know something’s wrong. It’s kind of like the [Liz Phair] example of changing guitars. We have our own interior instrument, and you can play it on a different instrument by saying it out loud.

Are there times of day that you tend to write?

I mostly write at night. During the day I’ll do research, do interviews, do reading. I just find the psychological interruptions [during the day] difficult. I can write if it’s a very, very specific task. If I know what I need to write, I can write during the day. If I don’t know…

… then it’s a nocturnal thing.

Exactly. What usually happens is that I’m writing along, and I’ll start to explain something, and I’ll realize “I have no idea; I thought I knew this thing, I thought I had total command.” So my writing is constantly interrupted by my own ignorance. I’ll realize, say, that I don’t really know what a neural net is; I can’t go any further until I master some degree of understanding what a neural net is.

I think this is a really important idea: that willingness to start writing even though there are big gaps in your knowledge. I think there are a lot of folks who feel as though they need to have total mastery of their subject before they start writing — and those turn out to be the people who never start writing…

Sometimes, I’ll skip ahead — I’ll put in a note and just figure that I’ll come back to it, and I’ll keep writing. But sometimes, I’ll punt a little bit by trying my best to guess what it is, and then I’ll have to go back. But that first draft is very helpful, because it illuminates what I need to learn. And then of course my last couple of books were written in public, because I posted a lot of it online — which I highly recommend, because I got feedback. I learned things I got wrong, things that weren’t clear, things that were stupid, things I didn’t even know about.

Can you share an example of how a specific piece or section of a book came about?

I just published an essay on the myth of the superhuman AI. That began as a letter to Sam Harris. He’d been talking about the Elon Musk/Stephen Hawking argument about why we should be scared about AI, but in this interview he’d done with Kate Darling, I could tell that he was open to hearing different perspectives. So I decided to write a little note to him, and as I was writing, it started getting longer, and I started to have to do reporting to defend my case… And then I started to think: “I feel strong enough about this that this would be useful for more than just one person.” So then I began to fill it out — and I did send it to Sam — but then re-worked it into something public.

How long was the email you eventually sent?

Maybe 4,000 words?

And you just sent it out of the blue? Like, “Hey man, I’m just going to drop this 4,000-word email on you…” (Laughs)

Right!

I’ve actually found that I am trying semi-consciously to get back to what we used to do in the early days of email, which was to write long, thought letter-like argumentative missives to each other. I’ve had five or six of those in the past few months. It’s really nice. There’s something about the letter format that helps you get past the blank page problem.

Exactly. I tell my kids and every writing student I’ve ever encountered: if you’re stuck, just write an email to me. And that works. Just write it to a particular person. And in fact I learned how to write on email. I’d never written before, with school, it was a struggle — but when I started to do email, you’re writing to a very specific person, you’re concrete, and you’re really trying hard to communicate. You’re not trying to impress anyone else. And teachers have discovered this. They actually did a study on it — having kids write in class and then email. And they evaluated the writing quality of the kids writing essays vs. email — and invariably, they were writing better in email.

There’s a connection there to something we have in common in a way. The first real writing that I did in public, in the early 1990s before I started writing professionals, was on early bulletin boards — a little on the Well, but mostly on ECHO in New York. It was really an important threshold for me: the first time I was willing to go in front of an audience and say something like, “Hey, I’ve got this theory about how the media is working,” or whatever. I mean, it was just an audience of like thirteen people…

But those were the right thirteen people! That’s how my first book started. I went to the first and second Articial Life conferences, and I basically blogged every single talk on the WELL. And that got passed around in the very embryonic Internet at the time — that enthusiasm was actually the genesis of Out Of Control. Having that feedback from a very small group of people — it was that support that made me think, okay, this should be a book. So I think writing in public has been a fantastic way to learn.