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Aug 1, 2016

How Wired Magazine’s Senior Maverick Kevin Kelly Writes: Part Two

New York Times bestselling author and co-founder of Wired magazine, Kevin Kelly, stopped by the show to chat with me about his journey from travel journalist to famed futurist.

Mr. Kelly’s storied and winding career has taken him around the world in search of visions of the new digital frontier.

Kevin is a renowned TED speaker and author of multiple bestsellers including his latest, The Inevitable: Understanding the 12 Technological Forces That Will Shape Our Future, a title that offers an optimistic roadmap of how new technologies will shape humanity.

Dubbed “the Most Interesting Man in the World” by Tim Ferris, Mr. Kelly began writing on the internet near its inception and never looked back. He has taken gigs including Editor for the Whole Earth Review, and presently Senior Maverick at Wired magazine, a magazine he co-founded in 1993, and where he served as Executive Editor until 1999.

Join us for this two-part interview, and if you’re a fan of the show, please click “subscribe” to automatically see new interviews, and help other writers find us.

If you missed the first half you can find it right here.

In Part Two of the file Kevin Kelly and I discuss:

  • Why the Author Can’t Write on the Road
  • The Importance of Delegation as a Writer
  • The Cool Tools Kevin Kelly Uses to Get Words on the Page
  • A Futurist’s Expansive Definition of Creativity
  • How Lateral Thinking Can Improve Your Writing
  • Why Steven Spielberg Asked Mr. Kelly to Predict the Future

Listen to The Writer Files: Writing, Productivity, Creativity, and Neuroscience below ...

The Show Notes

The Transcript

How Wired Magazine’s Senior Maverick Kevin Kelly Writes: Part Two

Jerod Morris: Hey, Jerod Morris here. If you know anything about Rainmaker Digital and Copyblogger, you may know that we produce incredible live events. Some would say that we produce incredible live events as an excuse to throw great parties, but that’s another story. We’ve got another one coming up this October in Denver. It’s called Digital Commerce Summit and it is entirely focused on giving you the smartest ways to create and sell digital products and services.

You can find out more at Rainmaker.FM/summit. That’s Rainmaker.FM/summit. We’ll be talking about Digital Commerce Summit in more detail as it gets closer, but for now I’d like to let a few attendees from our past events speak for us.

Attendee 1: For me, it’s just hearing from the experts. This is my first industry event, so it’s awesome to learn new stuff and also get confirmation that we’re not doing it completely wrong where I work.

Attendee 2: The best part of the conference, for me, is being able to mingle with people and realize that you have connections with everyone here. It feels like LinkedIn live. I also love the parties after each day, being able to talk to the speakers, talk to other people who are here for the first time, people who have been here before.

Attendee 3: I think the best part of the conference, for me, is understanding how I can service my customers a little more easily. Seeing all the different facets and components of various enterprises then helps me pick the best tools.

Jerod Morris: Hey, we agree. One of the biggest reasons we host the conference every year is so that we can learn how to service our customers — people like you — more easily. Here are just a few more words from folks who have come to our past live events.

Attendee 4: It’s really fun. I think it’s a great mix of beginner information and advanced information. I’m really learning a lot and having a lot of fun.

Attendee 5: The conference is great, especially because it’s a single-track conference where you don’t get distracted by “Which session should I go to?” And, “Am I missing something?”

Attendee 6: The training and everything — the speakers have been awesome — but I think the coolest aspect for me has been connecting with those people who are putting it on and the other attendees.

Jerod Morris: That’s it for now. There’s a lot more to come on Digital Commerce Summit. I really hope to see you there in October. Again, to get all the details and the very best deal on tickets, head over to Rainmaker.FM/summit. That’s Rainmaker.FM/summit.

Kelton Reid: These are The Writer Files, a tour of the habits, habitats, and brains of working writers from online content creators to fictionists, journalists, entrepreneurs, then beyond. I’m your host, Kelton Reid, writer, podcaster, and mediaphile. Each week we’ll discover how great writers keep the ink flowing, the cursor moving, and avoid writer’s block. New York Times best-selling author and co-founder of Wired Magazine, Kevin Kelly, stopped by the show this week and chatted with me about his journey from travel journalist to famed futurist.

Mr. Kelly’s storied and winding career has taken him around the world in search of visions of the new digital frontier. He’s a renowned TED speaker and author of multiple best-sellers, including his latest, at The Inevitable: Understanding the 12 Technological Forces That Will Shape Our Future, a title that offers an optimistic roadmap of how new technologies will shape humanity. Dubbed, “The Most Interesting Man in The World” by Tim Ferriss, Mr. Kelly began writing on the Internet near its inception and never looked back, taking gigs including editor for The Whole Earth Review and, presently, Senior Maverick at Wired Magazine, a magazine he co-founded in 1993 where he served as executive editor until 1999.

Join us for this two-part interview. If you are a fan of the show, please click “subscribe” to automatically see new interviews with your favorite authors and help other writers to find us. If you missed the first half of this show, you can find it at Writerfiles.FM in the show notes.

In part two of the file, Kevin and I discuss why the author can’t write on the road, the importance of delegation as a writer, the Cool Tools Kevin Kelly uses to get words onto the page, a futurist’s expansive definition of creativity, how lateral thinking can improve your writing, and the day Steven Spielberg asked Mr. Kelly to predict the future.

Why the Author Can’t Write on the Road

Kelton Reid: Do you have an office? Once you’ve traveled the world and gotten all the stuff you need — researched all the stuff — do you go back to the office then, or do you feel like you can write on the road?

Kevin Kelly: I cannot write on the road at all. I can’t even write on planes. I can’t even write in hotel rooms. I do all my writing here. I have this magnificent studio. I call it a studio, it’s two stories. It’s in California. It’s all white. It’s got a huge ceiling. There are two stories of books. I have all my toys — my Lego wall here. I have a Styro Bot. I built it for me and my way of working.

Camille’s just right over there. I have another assistant too, who does the website stuff. I have my big, huge whiteboard. I’ve got everything. I have a standing — and a ball, so I can move from standing to sitting within seconds. I need to be here to get my writing done, and I have the privilege of being able to control my time that way. I don’t know if I need to, but that’s how I choose to. That works for me.

You’re right about the travel. When I’m traveling there’s two kinds — there’s the traveling for doing talks … My livelihood is basically giving talks in China. Most of my fans are in China. I have 20 times the number of fans in China than I do in the U.S., so I go to China to do talks. Because I have this obsession with Asia, I usually will piggyback other trips either in China or elsewhere around Asia when I go because I’m photographing the disappearing Asia. When I’m in photograph mode I can do nothing else. It’s really weird, but I become totally a camera.

I’m just a camera. I’m a walking camera. I started off in the 1970s doing that. That’s what my first thing was. Instead of going to college, I went to Asia as a photographer and I was photographing the stuff. I was a camera. I worked from the beginning of daylight to the end of daylight as a camera.

Still when I go to Asia — the same thing, I am just there. Then, when I’m in the hotel, I’m downloading, backing up all my stuff. Doing the minimum amount of e-mail that I need to do. Then I’m in bed. Then the next day, I’m just a camera. I find it really hard to — I’m happy if I can do my e-mail. I can’t write then. When I come back, then I can shift. I’ll leave the camera off to the side and then I can try and write.

Kelton Reid: That sounds cool. It sounds like you’ve got these processes in place that help you to process, crunch all the information you see and then you get back to the designated writing space to get into the flow.

The Importance of Delegation as a Writer

Kevin Kelly: The other thing that I learned to do at Wired, working through the magazine, was delegate and hire. For 10 years I did Cool Tools myself. Five days a week, I was editing. I wasn’t writing all those reviews, but I was soliciting, getting them in, editing everybody, sending it back, going rounds of approval, posting it and finding the pictures, and doing the access information. At some point — it made money from the very beginning. “Okay, so I’m going to hire editors to do this.” I was overseeing a publisher, but they were doing the work.

That’s the other thing that I have learned to do, is to hire out. That’s the one thing I wish I’d learned earlier in life, to hire people better than yourself as a way of extending your reach. Cool Tools — Marcus is running that, basically. Silver Cord — my partner in that is running that. I don’t have a partner yet in True Films, but Claudia — who is here — is helping me now. That’s the idea. The way that I found to leverage my ideas and perspective is to hire whenever I can.

The Cool Tools Kevin Kelly Uses to Get Words on the Page

Kelton Reid: That’s cool. For scaling and probably peace of mind too. To harness your skills and your creativity. Speaking of Cool Tools, let’s talk a little bit about the Cool Tools that you use to actually get words onto the page, if you don’t mind. I’d love to know. I know you’ve got some organizational hacks in place, it sounds like, but are you a Mac guy or are you a PC guy? When you’re actually sitting down to get words onto the page, what are you using there?

Kevin Kelly: There’s a joke. I’ll actually just show you a picture of my — I have a beige, boring minivan, but the back window is covered with little white apples, like a million of them. I have been an Apple user from the Apple 2e. We did a famous Wired cover about praying for Apple because there was a brief spell before Jobs came back that I thought I was going to have to actually make the big switch to Windows. I was within two months of doing that, but he came back in time and saved the day.

Yeah, I’m a total Mac — we’re a Mac household. I have an iPhone. I work on a Mac — they call it a Mac Tower. It’s a behemoth machine that sits below me. I have two cinema screens: one at sitting height and one at standing height. I can just toggle between them. I have a little, tiny, 11-inch Mac Air that I take with me when I travel. It’s big enough just to do e-mail and primitive web. I have my PowerPoint speeches mounted, and that’s it.

I’m not a very mobile person, the first smart phone I had was Apple 6. I’m old-school in that sense. E-mail’s the best way to reach me. I work on a desktop. I’m not mobile. When I take pictures I have to process them. I use Lightroom, which I think is fantastic. I don’t even need Photoshop. I just use Lightroom for managing my gazillion …

By the way, I have them all backed up to not only Google, but I’m a insane, radical, extreme backer-upper. My photos are backed up on three clouds and three different hard disks beyond the cards that I have. I also have them backed up in three different places while I travel. Needless to say, I have never lost an image.

Kelton Reid: Is that known as RAID?

Kevin Kelly: Yeah, exactly. I have my own version of RAID. Right, exactly. The tools I use for writing — eventually I get into Microsoft Word. I don’t always start there. Believe it or not, I sometimes start writing in my e-mail because it’s so simple and I’m not going to lose it. I can keep it up. I used to mail it to myself as a backup. That was long before I had Time Machine.

Sometimes the first notes will be in all kinds of things. Sometimes it’ll be in Google Docs. Sometimes it’ll be in my e-mail. Sometimes it’ll be in Notes. Eventually it gets to Microsoft. When I’m writing a bigger piece I actually will move things, at some point, into Scrivener. Scrivener is this really cool software that’s used by people doing long-form writing, whether it be fiction or nonfiction, or sometimes screenplays. It’s a card-based organizing metaphor, so things have cards and you can move these cards around. The cards can have an indefinite amount of text in them, and you can put them in hierarchies or you can keep them flat, but the idea is that you can move all this stuff around.

It takes the place of the old way where we actually did cut and paste. Had things in piles and moved piles around on the floor, or index cards on your desktop. It does that. And it’s really good for organizing lots of things in lots of parts. I’ve used that for the last two books, and I would definitely use it again for any other book I did. I think that’s on both Mac and Windows.

I’m using Scrivener, but at some point it’ll make its way into a Word doc in the final form. That’s just because, in my experience working with magazines and book publishers, this is the universal format. It just has to reach there at some point.
Kelton Reid: The track changes and traditional publishing.

Kevin Kelly: Yeah, exactly.

Kelton Reid: I skipped over a big one, but here is one for you. You probably are rubbing elbows with writers — and you have been for much of your career — do you believe in writer’s block?

Kevin Kelly: I don’t. If you mean do I experience writer blocks, that’s all I can say. I’ve never really talked to the other writers about writer’s block, so I can’t say whether they have it or not. I have never had them volunteer conversation about it. I was just hanging out last week with all these science fiction authors — very published successes — and this never came up. I have not experienced it myself.

In talking to them about their work habits and stuff, some of them have pretty regular, “write every day” kind of things where they’ll write about something every day. Maybe it’s not about what their book is, but they’ll do something. It has not been an issue in my experience.

Kelton Reid: Cool. That’s good. Knock on wood.

Kevin Kelly: Yeah.

A Futurist’s Expansive Definition of Creativity

Kelton Reid: All right. Let’s get into creativity a little bit. I know we’ve got a few more minutes here. I think creativity is probably inherent to a lot of what you do, but it might not be labeled as creativity when you’re getting into technology and looking to the future. Do you think that you could define creativity for us?

Kevin Kelly: My image of creativity is a diagram in a book called The Act of Creation by Koestler. It’s an old book. It was his attempt to try and figure out what creativity is. His diagram was very simple: take two index cards that are inserted into each other so they form — from the end — a profile of a cross. So there are two planes that are intersecting, you have a flat plane and a vertical plane. You have two planes that are intersecting. His idea was that all creativity is basically taking two unrelated planes and making them intersect. That’s the visual image that I have of creativity, which is you are making a connection, an intersection between things that have not intersected before.

Jokes are kind of like that. A joke is when you take two things that don’t seem to be related and you bring them together in some way that’s plausible and it’s funny. New ideas, new innovations are the same kind of thing where you recombine existing mechanisms in a way that haven’t been combined before. Brian Arthur’s and Paul Romer — two separate guys with two separate theories, but they’re both the same, which is that the fountain of all innovation is just a recombination. In fact, the origin of all wealth is actually recombination. You’re just recombining things.

This idea of intersecting things that had not intersected before is my definition of creativity. There are, of course, rules. You can’t just take any random thing, the new intersection has to work in some way. It has to be plausible, interesting, whatever — but fundamentally, that’s the act. When I see something creative, it’s usually because someone has — we talked about the other metaphor of a leap somewhere. They have stepped off something and they’re stepping somewhere else, but there are actually two legs. They actually have a leg in the departure point and a leg in the arrival point. Those two things have not been bridged before. That’s my image of an intersection of two unrelated ideas.

Kelton Reid: I like it. I like it a lot. I think that we’re getting close here. I have a couple of other questions for you, but —

Kevin Kelly: Let me just say one thing about the creativity.

Kelton Reid: Oh, I’m sorry.

How Lateral Thinking Can Improve Your Writing

Kevin Kelly: No, because I’ve gotten to work with many of what I would consider some of the most creative people working today, alive today. People who are technically geniuses like Danny Hillis, artistically genius like Brian Eno, and cultural genius like Stewart Brand. It’s really been interesting to watch them operate. I think they have trained their minds to do this. They’re doing the thing I’m saying with these unrelated planes intersecting, but they do them in different ways.

Brian Eno, he’s the most lateral thinker I know. Lateral meaning that he’s associating ideas coming from off to the side. We have a tendency to proceed in a linear way, or a way in which there’s the obvious things in front of you that you may want to combine. He has an ability to reach off to the side into something that is unexpected, trying to make that association that will work. He’s particularly good at reaching behind his back or off to the side — that’s what I meant by laterally — to bring something in. That ability to, in some senses, dismiss or ignore the obvious ones and to reach for the unobvious but yet still works, is something that I think actually they train.

Brian Eno has a famous set of cards called Oblique Strategies that he and a partner use to make music. These were prompts that they would pick up at random to force themselves to do this lateral thinking. They were prompts like, “Take the most obvious thing and ignore it,” or “What about the middle? Emphasize the middle.” They were almost random things. Often, that action would not be the thing that worked, but that would lead them to this other unobvious next step that would work. That’s one way.

Those cards are actually very valuable and useful for anything. I have a deck right here. I have my own internal ones of when you’re in a situation — say when you’re stuck, you use these things as prompts, exercises to force yourself to think about these other approaches. It’s very handy. I think, internally, that’s what Brian and other are doing, is actually have a set of little things that they’re running through, sometimes unconsciously, as they try and prompt themselves to take this lateral approach.

Then there are others like Marvin Minsky and Danny Hillis who are very technical. I think they do something very similar, particularly Marvin, which is pretend that they’re not human. They try to approach this as if they were seeing it for the first time, as if they were coming from another planet, as if they were pretending they were, often, a robot. “How would a robot do this?” To try and do the same thing of looking at it with fresh eyes, looking at it in a way that no ordinary human would look at it, not as a way an ordinary human would look at it.

Then Stuart Brand, who also has this ability, I think his little heuristic that he also trained himself to do was to force himself — each time he approached something he would force himself to try and find a different perspective on it, including using the words that he used to describe something. He would never, ever repeat himself. If he was talking about something he knew, he would require that he use different words when talking about it this time to this person, even though he’d been talking about it for a thousand times before. That constraint would require him — because of the new words — to see it differently. Then he would have an insight just because he forced himself to use different words.

Those are some of the ways that I’ve seen some of the most creative people I know use this on a daily basis. They have trained themselves to be better at this on an ongoing basis — not just when they’re sitting down, but as a habit.

Kelton Reid: For sure. Yeah, I know screenwriter John August has a similar set of prompts like the Oblique Strategies that he uses for screenwriters which has proven to be very helpful. I think writers can use that in whatever way they think to kick-start their writing for sure.

Side note, I love Brian Eno’s Music for Airports. I actually listen to it while I’m writing. I find that it helps because it’s kind of meandering and ambient, of course.

I’ve got to slip this one in here. I know that in The Inevitable and Understanding the Technological Forces That Will Shape Our World, you’ve talked about VR quite a bit. I heard you say you were reading Ready Player One, which is Ernie Cline’s journey into VR. What is it? The OASIS?

Kevin Kelly: Correct.

Kelton Reid: Interesting intersection there. I think you’ve worked with Steven Spielberg in the past, and he is adapting that book into a movie. Have you heard anything about that?

Kevin Kelly: I have not heard — either from Ernie or elsewhere — about what state the Spielberg Ready Player One is in. I’ve heard different rumors about whether it’s actually going to be in VR or not. I think there is likely to be some VR component, probably a VR game version. But no, I don’t know anything more about it other than what has been published. I think that it’s an ideal Spielberg movie for many reasons, not the least of all the references to the seventies and eighties that I’m sure he’d be very good at.

Kelton Reid: Right. I thought it was interesting that it takes place in 2044 and he actually tapped you to help him predict 2054 in Minority Report.

Why Steven Spielberg Asked Mr. Kelly to Predict the Future

Kevin Kelly: Right, yeah.

Kelton Reid: I thought maybe he had tapped you again.

Kevin Kelly: No. It was just not me, it was a group of us, and as far as I know he hasn’t reached out in that sense to do that — which was a very amazing experience. There was a set of people, including the people I just mentioned, except I don’t think Brian was there. Doug Copeland and some other — Jaron Lanier — were present, and our job was to make this world comprehensive. It was really interesting because we did a lot of arm waving about these things.

Spielberg is sitting in the room and he’s there with his little pencil and pad. He says, “Okay, what are people sleeping on? What do the beds look like? How about for breakfast, what are people having for breakfast?” That requirement to be that specific was very galvanizing because you couldn’t just talk about general things. He wanted to know what the beds looked like. So you began to think, “What do they look like? Are they any different? The same? Are they waterbeds?” That was so profound for me, because that really changed how I try to think about the future now.

Kelton Reid: How cool. I really appreciate you taking time out to chat with us about your process. The Inevitable: Understanding the 12 Technological Forces That Will Shape Our World, a very optimistic roadmap of the future. Really cool stuff. It’s out now and we can find it out there. You link to it at and it’s on Amazon. I’ll link to your Google Plus Page as well and your Twitter handle. Is there any other sign-offs for writers you want to drop on us before you go to the next interview?

Kevin Kelly: No, other than I do suggest that you look at the Cool Tools book that I did, which was self published. It’s this huge, oversized, thick, heavy, five pound, massive catalog of possibilities. There are some good writer tools besides Scrivener. There are some other resources for people making things and being creative — tools not just like the wrenches and pipes, but things like Elance, or what they would call Upwork these days. How to hire someone for help. Where to get a logo or book cover done. Check out that, that’s available on Amazon as well.

Kelton Reid: Mr. Kelly, thank you so much. We really appreciate it. Best of luck with all of your press rounds, and hopefully you’ll come back and talk to us again another time.

Kevin Kelly: Sure thing. Thanks for the attention. Appreciate it.

Kelton Reid: Thank you.

Thanks so much for joining me for this half of A Tour Through The Writer’s Process. If you enjoy The Writer Files Podcast, please subscribe to the show and leave us a rating or a review on iTunes to help other writers find us. For more episodes or to just leave a comment or a question, drop by WriterFiles.FM. You can always chat with me on Twitter @KeltonReid. Cheers. Talk to you next week.