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It’s time for another edition of our FREAK-quently Asked Questions – that’s when we run a set of fixed questions past some noteworthy guest. The first time out, we talked to Boris Johnson, the Mayor of London:

Boris JOHNSON: I collect old cheese boxes.

Today, we’re putting the questions to Kevin Kelly, one of the founders of Wired magazine. He’s also a technology writer. His books include What Technology Wants and New Rules for the New Economy. He’ll tell us how he got started in publishing …

Kevin KELLY: I think I was the first person in the world to be hired online in 1983.

Why he’s dying to travel into the future …

KELLY: I would give so much just to get a sense of the trajectory of the cosmos, because I think we’re really blinded and shortsighted, and particularly swayed by the last 100 years …

And then there’s this:

Stephen J. DUBNER: When’s the last time you dropped acid, Kevin?

KELLY: I tell you, there’s nothing more boring than hearing someone’s acid trip.

*      *      *

DUBNER: O.K., so let’s start. Tell us who you are and what you do.

KELLY: My name is Kevin Kelly. I’m “senior maverick” at Wired magazine, a magazine that I co-founded about 20 years ago. And what I do is write books about the consequences of technology; the impact of technology on our lives, which is really what Wired was about: the culture around technology, rather than technology, itself.

DUBNER: And Kevin, tell me in 60 seconds or so what you actually do in a given day?

KELLY: I spend most of my day reading. I read magazine, and books, and then I  try and write a little about what I learned. Of course, I also write emails. Then I take a hike or a bike, and I also try to take one photograph a day. So I mostly spend my time reading.

DUBNER: Now, Kevin, what would you say would be the best investment you’ve made, any kind of investment, financial, emotional, educational, whatever, that’s got you to where you are today?

KELLY: I spent almost a decade traveling in Asia with very little money, and that transformed my life, and it gave me insights into how things are actually done. And I also caught a really bad case of optimism there because I saw with my own eyes nations bootstrapping themselves from poverty into prosperity.

DUBNER: This was after you went to college but did not graduate from college, correct?

KELLY: Right. I did one year of college and then dropped out. And instead I awarded myself a graduate degree in Asian studies by backpacking through Asia at a time when it was in transition.

DUBNER: And what is your advice to people today who are thinking about not going to college or dropping out of college?

KELLY: I think you don’t need college if you have a project that you want to throw yourself into, if you have the gumption and the discipline, if you have a really good alternative. And I’ve told my kids if you don’t have that, then you’ve got to go to college.

DUBNER: Your kids are how old?

KELLY: 26, 24, and 18.

DUBNER: And what’s their college status?

KELLY: They all went because they didn’t have something as an alternative.

DUBNER: Kevin, who’s been the biggest influence on your life or work and why?

KELLY: A man called Stewart Brand who taught me how to think honestly. He was the first publisher and creator of the Whole Earth Catalog, which I read in high school. And the message of that kind of “hippie bible” was you can invent your life to do whatever you want and that you don’t need to ask permission.

DUBNER: And you went on then to be an editor at the Whole Earth Catalog, yes?

KELLY: I did. The only job I ever want to have was to work for the Whole Earth Catalog because I felt that it was speaking to me directly. I was hired in a kind of a curious way. I was hired online. I think I was the first person in the world to be hired online, in 1983.

DUBNER: Wow, what was the portal that allowed you to do that?

KELLY: It was an experimental online network called EIES, E-I-E-S, run by the New Jersey Institute of Technology. And I finagled my way into it by — I’d become a travel writer at that time, and I was writing about this network nation as if it was a new territory. And I apparently had the right voice for online. And we recognize that voice these days as the voice of a blogger.

DUBNER: And that I guess, directly or indirectly, led to you belonging to a group of people who ended up starting Wired magazine, yes? I mean, it’s kind of a continuous thread?

KELLY: Yes, it was. But I mean before that, I launched the first hackers’ conference with Stewart. We also launched The Well, which was the first public access to the Internet in ’84 or ’85.

DUBNER: Given the modern face of cutting-edge technology, let’s invite everybody out there to summon the image of a person who represents that. And it might be a Steve Jobs-like character. It might be someone a generation or two generations younger than that. But you guys were a bunch of hippies that really kick-started what we now know as the digital revolution. I think most people don’t think of the digital revolution today as being affiliated with hippiedom at all.

KELLY: They don’t, and that is actually one of the untold stories. Actually, it was told by The New York Times technology writer, John Markoff, who wrote a kind of overlooked book called What the Dormouse Said, which was telling the hippie origins of the personal computer and how basically from Doug Engelbart and Steve Jobs and Stewart Brand, they were all dropping acid; they were trying to augment human cognition, not trying to make a new industry. And a lot of the earliest entrepreneurs in Silicon Valley in the computer world were former hippies who were living on communes and learned some small business skills making candles or macramé, or whatever it was, and transferred that into this ethic of the entrepreneur, which is now kind of all fancy and hip. And that is definitely a thread of Silicon Valley that’s not widely appreciated.

DUBNER: Yeah. When’s the last time you dropped acid, Kevin?

KELLY: I have only dropped acid once in my life. And I was 50-years-old, on my birthday.

DUBNER: Which was how long ago? You’re how old?

KELLY: I’m sixty-two. So I took no drugs at all, even though I was a hippie. I was one of those weird ones that didn’t do drugs. But I decided to make it a sacrament and on my 50th birthday, I dropped three tabs of acid and saw God.

DUBNER: What did God look like? What did she say?

KELLY: I tell you, there’s nothing more boring than hearing someone’s acid trip.

DUBNER: I don’t know, I’ve never done acid. Was it positive at least?

KELLY: It was a positive experience. And I did a lot of research on trying to find out how you do this well, and it turns out that that was actually kind of hard to find, but you do it with a guide and in the right setting. So I did it outdoors. I had a very experienced person who was sitting by me, and taking care of me and leading me through. And I also had a source for the drug that was very pure. However, I have to say that I was given four tabs and I threw the last one into the ocean when I was done saying, you know, I don’t need to do that again.

DUBNER: What do you collect and why?

KELLY: You know, I don’t have that collector gene. I have a couple little things that I collected on my travels in Asia, and one was Coke bottles. And I collected the Coke bottles because the different countries in Asia, they had different scripts.

DUBNER: Coke is bottled locally everywhere in the world, isn’t it?

KELLY: Right, and so that was the interest to me was this universal symbol that had these local variations. And I thought that was really cool. You know, the Chinese and the Japanese and the Thai. They were all different, and yet they were all the same in some ways too, the same shape.

DUBNER: Kevin, what can you tell us about your strategy for creating and managing computer passwords?

KELLY:  I use a mnemonic formula to generate passwords that are kind of specific to each site that I go to. So it’s a formula that uses part of the site’s name in the password.

DUBNER: So yours is algorithm-ish that’s adaptable to any site then, yes?

KELLY: Exactly, so my assistant could generate it if needed, and we’d all agree on what it was, and yet it’s unique to that site.

DUBNER: What’s your net worth compared to that of your parents when you were, let’s say, 16?

KELLY: I didn’t know what my parents’ net worth was. I still don’t know. We never talked about it.

DUBNER: What’d your folks do for a living?

KELLY: My father actually worked for Time-Life. He was not in the editorial side. He was in something that was called operations research at the time, that we would now call, like, I.T. He was one of the people who brought computers to the magazine world. And then later on he was involved in this really kind of weird startup that you might have heard of, called HBO. And so he was involved with the guys who were taking cable TV and trying to put it on a satellite.

DUBNER: So did you grow up in New York then?

KELLY: I grew up in New Jersey, in Westfield, New Jersey. My dad worked in New York. And my parents never talked politics. I have no idea if they ever voted. I don’t even know what they were making. And so I don’t have any idea.

DUBNER: O.K., but how about your life and your family and consumption patterns and so on, would you say you’re financially better off or worse off than your parents?

KELLY: Well, I’m sure we’re as well off, and we might be better off. But it’s all relative. For instance, when I grew up, I never ate out in a restaurant. My entire life, every meal, my mom cooked. I don’t know whether we couldn’t afford it, it’s just that we didn’t do it. Now, that’s not obviously true of my own life, but I don’t know if that was more about money, or more just about the culture at the time.

DUBNER: What was your favorite meal that your mom made?

KELLY: Tuna fish salad. And we were raised Catholic, so we had it on Friday. And that’s something I always looked forward to.

DUBNER: Is your mom still alive?

KELLY: Yeah, she is. She’s 86 or 87 and sharp as ever.

DUBNER: When you go home does she still make you the tuna fish?

KELLY: Yes, she will.

DUBNER: Can you make it now as well as her? Is there a recipe or … ?

KELLY: No, I can’t. I don’t know … You know it’s funny because I’ve never asked her for the recipe.

DUBNER: Yeah, why not? I mean, you’re helping invent the Internet and you can’t figure out the tuna fish?

KELLY: Yeah, I guess, I like the idea that she can do something that I can’t.

Coming up on Freakonomics Radio: why Kevin Kelly, who is sometimes mistaken for Amish, is not Amish:

KELLY: I’m Amish-ish, in the sense that I am, in minimizing the number in my life. But the Amish are not interested in maximizing the number of options in the world and I am.

And, his coolest book yet. It’s called Cool Tools.

KELLY: And tool is in the broadest sense of something that’s useful to you.

*      *      *

Kevin Kelly is a technology writer and a founder of Wired magazine. He lives and works in northern California, “in a rambling house at the end of a road just a mile from the Pacific Ocean,” as he puts it. Usually when we record an interview like this one, we either make someone go to a studio or we send an engineer to them with a portable recording. But Kelly, being Kelly, offered to record himself. So what you’re hearing is me asking him questions from a radio studio in New York, and Kelly responding from his writing studio in California, recording himself on a small digital recorder with two built-in microphones. It’s called a Zoom H2 Handy. Later he uploaded the file to Dropbox. We downloaded it, and, to borrow Kelly’s words, we “zippered it into the half” of the conversation that we recorded in New York. So that’s what you’re hearing, as Kevin Kelly answers our FREAK-quently Asked Questions.

DUBNER: Kevin, what do you worry about now when you go to sleep at night?

KELLY: I don’t worry about anything when I got to sleep at night. I am kind of a machine that can just be turned off and turned on. I have constructed my life to try and have very few regrets and no worries. And so while I may worry about like whether this is really recording or not. I am not worrying about things at night.

DUBNER: So you’re an in-the-moment worrier. You’re not a retrospective worrier.

KELLY: Yeah, exactly.

DUBNER: What is one thing throughout your life maybe that you’ve spent too much on, but do not regret?

KELLY: My library. I have a two-story library filled with lots of books. You know, I’ve read, maybe two-thirds of them. So there’s lots of books that I haven’t read. They take up a lot of space, but I just love it. I just would not give it up for anything.

DUBNER: These days do you typically buy a book on paper, or an e-version?

KELLY: I’m buying both. So I can have multiple versions of books. And that’s certainly an indulgence.

DUBNER: When someone comes over to your house and they’re in your library and they see a book that they’re interested in, what do you do? Do you give it to them?

KELLY: You know, I wish I was freer with my books in giving them away. But, no, I don’t give them the book. Anyone who visits my library gets a book from me. But it’s usually a book that I have made, and I produce two or three books a year, little things that I print on Blurb or Lulu. So I’m a kind of recovering photographer. And they can range from photo books, or I have other little private booksa book on drawings that I’ve done over the years. So I have a little stash of private editions. And that’s what I give away.

DUBNER: So one of the books that you’ve made, but that’s on a much bigger scale than the ones you’re talking about here, is this amazingly interesting book, Cool Tools. Tell us about that a little bit.

KELLY: So Cool Tools is a book on paper, and it’s only available on paper, that’s a little bit oversized.

DUBNER: It’s a lot oversized. Come on.

KELLY: Yeah, if you open it up it’s kind of like a small towel, the size of dish  towel. And it is about 1,500 recommendations for cool tools, and tool is in the broadest sense of something that’s useful to you. So it could be a hand tool, like a really good pair of pliers. Or it could be the best glue gun in the world. Or it could be something like a piece of software, or software app. Or it could be something even like a service like eLance, which is this global market for freelancers. And they’re collected and  arranged into this book that does something that your phone doesn’t do or that the Web doesn’t do, which is all of these things arranged on a page, and the design of them being adjacent to one another, there’s something unconscious that provokes in your mind connections between them. So there’s a kind of a buzz, an exhilaration you get, because your brain is making associations between all of these tools.

DUBNER: You know, when I first got Cool Tools, I guess it came out in 2013. And I loved it. And I loved looking through it. And my kids loved looking through it. And we like to give it away as a present for high-school graduation, or even bar mitzvahs and bat mitzvahs, because it’s like there’s a world out there. And there’s you here. And you are going into that world. And it’s very easy to hear about the 10 things that everybody is talking about at the same time in media, social media, mass media, whatever. But then here’s another 1,000 things that you may not know about that are often better, cheaper, easier, and will kind of help you make your way through the world. And when I first got it and started looking at it, I thought it was just weird that you, the guy that we, or I at least, associate with Wired magazine, has put out this book, which is on paper, with everything from modern and cutting-edge tools to a lot of things about beekeeping, and homesteading, and keeping chickens, and so and so. And I thought it was just the greatest contradiction that the Wired guy would also be the super hippie guy, even if he’s the modern hippie guy. But now that we’re talking, I see no contradiction whatsoever. And I guess what I’m saying is I like that talking to you has made me, and I hope other people, see the connection between, you know, going low, low-fi and D.I.Y. and all of that, with the highest of the high-tech, that they really are connected, aren’t they?

KELLY: Yes, I think of myself as a minimalist in the sense that I am looking for the minimum amount of technology that will maximize my options. So while I am, in my role at Wired, a cheerleader for the benefits of technology, I’m trying to maximize the number of choices that we have in the world, I’m trying to actually minimize the number of things in my own life at the same time. That’s sort of why I’m not Amish. The Amish are minimized in the sense that they are really very selectively choosing …

DUBNER: Although you look Amish with the beard. People mistake you for Amish?

KELLY: I do. People say that I’m Amish, but I’m not Amish.

DUBNER: You’re Amish-ish.

KELLY: I’m Amish-ish, in the sense that I am in minimizing the number in my life. But the Amish are not interested in maximizing the number of options in the world and I am. So Cool Tools I subtitle as A Catalog of Possibilities, because I’m not encouraging people to buy all the tools in there. I mean, you kind of page through it and say, “Oh, I want this, I want that.” It’s more important that you know that these exist rather than that you purchase them because a tool is really just an opportunity with a handle. It’s just a way of thinking about something differently that we make real. And so you can use this as a resource of getting ideas about what is possible to do. And that’s why I think it’s really great for young people is to say look, you’ve been through school, you’ve been through college, but here is a whole realm of things that are possible for an individual to do these things. You can rent a bulldozer if you want to. You can design your own home and build your own home if you want to. It’s not that difficult. And so just knowing that can give you confidence to do other things that haven’t been done yet.

DUBNER:  Let me ask you a series of “favorite” questions that are, honestly these are the kind of questions that if you were asking me I’d hate them.

DUBNER: So what’s a favorite book or author?

KELLY: Favorite author is Annie Dillard.

DUBNER: Oh, no kidding.

KELLY: And her book Pilgrim at Tinker Creek was something that just made me want to write. And I can read that any time of day or night and just be filled with excitement. And I read anything by her. And to me she’s just genius.

DUBNER: Favorite music?

KELLY: Arabic pop.

DUBNER: Name some names.

KELLY: I don’t even know what the names are. They’re just compilations, and they play, and I don’t even know who the artists are, and they’re probably not even well known. It’s kind of like folk music.

DUBNER: Let me ask you this, when it comes to regret, and you’ve already told us that you are pretty good at not hanging on to regret at least at the end of a day, do you tend to have stronger regrets for things you did that worked out poorly or things that you didn’t do?

KELLY: Probably for things I didn’t do, just because they’re kind of opportunities lost.

DUBNER: Do you have list of those things that you had a chance at …

KELLY: No, I don’t …I have very, very few of them. One of the ones that, had we done it a little differently, and we do have a regret, is we didn’t have a fourth child.

DUBNER: Why? What would four do that the first three didn’t?

KELLY: You know, our last son was a little bit younger than, was a little bit separated from the older two. So it would have been a little bit funner for him. And just, you know, as we went along, we just realized how incredibly fantastic it was to have a household of kids around. And so, but things in terms of timing, and jobs, and biology, it just didn’t work out.

DUBNER: Here’s a big one. There are few people I can think of that I would rather ask this question of than you, Kevin Kelly. What’s the best possible future discovery or invention?

KELLY: I think nuclear fusion would be … not the best of all possible, but in terms of the near future, of something that we’re close to, I think this is one of the most promising technologies that we have. If we can have economic, synthetic solar, which is basically what it is, so you get a lot more energy out than you put in. That would be huge.

DUBNER: So that would mean theoretically coal as an electricity source goes away. Hydro, if you can’t build it, not a problem. Why is that such a game-changer in your view?

KELLY: Well, as far as we know, it wouldn’t contribute to global warming. And it would also take the same trends that we’ve had all along, which is we built civilization on the fact that we could find cheap energy. I mean if this planet didn’t have oil reserves or coal reserves, it’s really hard to imagine how we would have gotten this far.

DUBNER: Yeah, how far do you think we would have gotten?

KELLY: That’s a really interesting question. Like if you imagine that we only had wood, how far along could we have gotten? Because we could probably know enough now that we could maybe change the wood in some way. But whether we would have gotten as far as we had with wood only, I don’t know. I haven’t really kind of played it out, but that would be a wonderful counterfactual science fiction story if we replayed the earth’s history without the coal and oil reserves.

DUBNER: Here’s a hard one, Kevin: What do you think will eventually lead to humankind’s demise, if in fact there is such a thing?

KELLY: I don’t believe there’ll be a demise of any sort.  It’d be very, very difficult to eradicate all human life, even if you really wanted to. I mean even asteroids would do a good job of killing most of the people, but not all the people. I think what will happen is we’ll evolve until we’re unrecognizable, that the way humanity disappears basically is we become something so different from what we are that we want to give it a different name. I also think that that’s a plural. So I think that our destiny is to be many species. And there will be people who will say, under my dead body will my genes or the genes of my offspring ever be changed. And then there will be other people who will say, sign me up today.

DUBNER: What were you studying at college when you dropped out?

KELLY: Geology.

DUBNER: Geology. All right, so let’s imagine that instead of dropping out and traveling around the Asia, and then becoming this dude that you became, that you’d been a different kind of guy, and you’d stayed in college and gotten your geology degree. What do you think you’d be doing today had you not taken that alternate path?

KELLY: I might have made a good doctor because I think I’m really good at diagnosing things.

DUBNER: Medical diagnosis is so friggin’ hard, isn’t it?

KELLY: Yes, it’s hard. My wife actually runs a lab at Genentech, she’s a biochemist and genetic engineer. So I hear how hard it is to unravel even the smallest bit of what’s actually going on. And we still really — I mean, the brain we don’t know. The cell — you know, people’s image of the cell …Well, the cell is almost a solid. We think of it as kind of filled with water, but it’s really, it’s packed so much that there’s almost no room for things to happen. And we don’t even know how they happen actually.

DUBNER: It’s humbling too, isn’t it? Because you think as good as we humans have gotten at building systems — I mean, we can do air conditioning, and even some nuclear power and this and that — in terms of the most basic system, which we all own, we don’t really know how it’s put together and how it got that way.

KELLY: And to make matters more complicated, I think we are making our technology, like the Internet and robots and things like that, almost as complex as biological systems. And so my books have been about how we need to bring in biological thinking into our technology. We have to understand that they’re related, that they’re cousins, or if not brothers and sisters. And that our technology will become more biological as it progresses. And so this requires a different approach to what we make.

DUBNER: Last question, Kevin. What was the question that I should have asked you but failed to?

KELLY: You didn’t asked me if I was on a time machine where I would go.

DUBNER: O.K., Kevin, if you were on a time machine where would you go?

KELLY: I would go into the future. And I would go about 200 years. I think further than that I would just be lost.

DUBNER: And what would you want to see 200 years out?

KELLY: I would give so much just to get a sense of the trajectory of the cosmos, because I think we’re really blinded and shortsighted, and particularly swayed by the last 100 years. And so the question is, is there really a trajectory to our development and our progress? And I think 200 years would give me enough time for a second data point.

DUBNER: Would you make it a point to seek out your own great-great-great-grandchildren? Or would you avoid them?

KELLY: I probably wouldn’t do that, but I would Google myself.

DUBNER: See how well you held up?

KELLY: Because the honest truth is that even in 200 years, not one single one of us here is going to be remembered.

DUBNER: All right, I’ll make you this promise, if I somehow get frozen, boiled whatever and make it that long, I’m going to tell people about you.

KELLY: O.K. Well, thank you.

DUBNER: Kevin, nice talking to you. Thank you very much.

KELLY: It was great.

DUBNER: Bye, bye.

Thanks for listening, thanks to Kevin Kelly — for talking to us and for recording his end of the conversation — and thanks today and every day to our underwriters: those are the people who buy the ads on this program, that make it possible.

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