Tim Ferriss speaker headshot

Tim @ 1:21

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Hello ladies and gentlemen, this is Tim Ferriss, and welcome to another episode of The Tim Ferriss Show. And to start off, as I often do, with a quote. This is from one of my favorite writers of all-time, Kurt Vonnegut, and it goes as follows: “Here is a lesson in creative writing. First rule, do not use semicolons. They are transvestite hermaphrodites representing absolutely nothing. All they do is show that you’ve been to college.” I have the habit of using dashes in the same way, so I like to read this to remind me not to use that crutch. Also “pretty”, the adverb, I overuse that. In any case, Kurt Vonnegut, lots of lessons, lots of amazing books. If you need one to start with, go with Cat’s Cradle.

Today’s guest is Kevin Kelly. Kevin Kelly is one of the most interesting human beings I have ever met. He’s a dear friend. As for the bio, Kevin Kelly is senior maverick at Wired Magazine which he co-founded in 1993. He also co-founded the All Species Foundation, a non-profit aimed at cataloging and identifying every living species on Earth. In all his spare time, he writes best-selling books, he co-founded the Rosetta Project, which is building an archive of all documented human languages, and he serves on the board of the Long Now Foundation, which I’ve been honored to join as a speaker on one occasion. As part of the Long Now Foundation, he’s looking into, among other things, how to revive and restore endangered or extinct species, including the woolly mammoth. I’m not making this stuff up, Kevin is amazing.

This is going to be a multi-part episode, so there’ll be a number of different podcast episodes, because we went quite long. I hope you enjoy it. You can find all links, show notes, and so on, once we complete the entire series, at fourhourworkweek.com/podcast. You can also find all previous episodes I’ve done in this podcast. Fourhourworkweek.com/podcast, all spelled out. Without further ado, please enjoy, and thank you for listening.

Tim Ferriss speaker headshot

Tim @ 3:44

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Kevin, thank you so much for being on the show.

Kevin Kelly speaker headshot

Kevin @ 3:46

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It’s my honor.

Tim Ferriss speaker headshot

Tim @ 3:47

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I am endlessly fascinated by all of the varied projects that you constantly have going on. But that leads me to the first question, which is, when you meet someone who is not familiar with your background and they ask you the age-old “what do you do?” question, how do you even begin to answer that? What is your stock answer to that?

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Kevin @ 4:07

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These days, my stock answer is that I package ideas into books and magazines and websites, and I make ideas interesting and pretty.

Tim Ferriss speaker headshot

Tim @ 4:19

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Ooh, I like the “pretty”. We’ll come back to the aesthetic aspect, I think that’s a really neglected piece of the entire puzzle.

You do have, of course, a background … a lot of people are familiar with your background with Wired, but perhaps you could give folks a bit of background on yourself. Is it true that you dropped out of college after one year?

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Kevin @ 4:40

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Yeah, I’m a college drop-out. Actually, my one regret in life is that one year that I came. (laughs)

Tim Ferriss speaker headshot

Tim @ 4:56

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Oh, no kidding?

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Kevin @ 4:57

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Yeah, I wish I had just even skipped that. But I do understand how college can be useful to people. My own children have gone through … But for me, it was just not the right thing, and I went to Asia instead. I like to tell myself that I gave my own self a PhD in East Asian studies, by traveling around and photographing very remote parts of Asia at a time when it was in a transition from the ancient world to the modern world. I did many other things as well, and for me, it was a very formative time, because I did enough things that when I finally got my first real job at the age of 35 …

Tim Ferriss speaker headshot

Tim @ 5:33

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(laughs) Wow. Which job was that?

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Kevin @ 5:36

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I worked for a non-profit at 10 dollars an hour, which was the Whole Earth Catalog. Which had been a life-long dream. I said if I’m going to have a job, that was the job I want. It took me a long time to get it. But in between that, I did many things, including starting businesses and selling businesses, and doing other kinds of things, more adventures. And I highly recommend it. I got involved in starting Wired and running Wired for a while, and hired a lot of people who were coming right out of college. They were internists and they would do the intern thing, and then they were good and we would hire them. Which meant that, basically, after 10 years, whatever it was … this was their first and only job, and I kept telling them, “Why are you here? What are you doing? You should be fooling around, wasting time, trying something crazy. Why are you working a real job? I don’t understand it.” I just really recommend slack. I’m a big believer in this thing of kind of doing something that’s not productive. Productive is for your middle ages. When you’re young, you want to be prolific and make and do things, but you don’t want to measure them in terms of productivity. You want to measure them in terms of extreme performance, you want to measure them in extreme satisfaction. It’s a time to try stuff, and I think …

Tim Ferriss speaker headshot

Tim @ 7:06

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Explore the extremes.

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Kevin @ 7:07

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Exactly. Explore the possibilities, and there are so many possibilities, and there’s more every day. You don’t want- it’s called “premature optimization”. You really want to use this time to continue to do things. And by the way, premature optimization is a problem of success, too. It’s not just the problem of the young, it’s the problem of the successful more than even of the young. But we’ll get to that. That’s a long answer, too. (laughs)

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Tim @ 7:33

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That might turn into a therapy session for me at this precise moment in time, in fact.

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Kevin @ 7:37

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(laughs) Yes, exactly.

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Tim @ 7:38

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But when you are exploring that slack, I would imagine many people feel pressure, whether it’s internal pressure or societal, familial pressure, to get a real job, to support themselves. A lot of the decisions are made out of fear. They worry about being out on the streets, or it’s a nebulous, terror, anxiety. How did you support yourself, for instance, while you were traveling through Asia when you left school?

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Kevin @ 8:03

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I totally understand this anxiety and fear and stuff. But here’s the thing, I think one of the many life skills that you want to actually learn at a fairly young age is the skill of being, like, ultra-thrifty, minimal, kind of this little wisp that’s traveling through time … in the sense of learning how little you actually need to live, not just in a survival mode, but in a contented mode. I learned that pretty early, by backpacking and doing other things, especially in Asia … was I could be very happy with very, very little. You can go onto websites and stuff, and look at the minimum amount of stuff- food, say, that you need to live, your basic protein, carbohydrates, and vitamins, and actually, if you bought them in bulk, how much it would cost. I mean, you build your own house, live in a shelter, a tiny house. You don’t need very much.

I think trying that out, building your house on the pond, like Thoreau, who was a hero of mine in high school, is not just a simple exercise, it’s a profound exercise, because it allows you to get over the anxiety. Even if you aren’t living like that, you know that if the worse came to worst, you could keep going at a very low rate and be content. That gives you the confidence to take a risk, because you say, “What’s the worst that can happen? Well, the worst that can happen is that I’d have a backpack and a sleeping bag, and I’d be eating oatmeal. And I’d be fine.” I think if you do that once or twice … you don’t necessarily have to live like that, but knowing that you can be content is tremendously empowering.

Tim Ferriss speaker headshot

Tim @ 9:51

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Definitely.

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Kevin @ 9:52

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That’s what I did, that’s basically what I did. Was living in Asia where the people around me had less than I did and they were pretty content. You realize, “Oh my gosh, I don’t really need very much to be happy.”

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Tim @ 10:04

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Did you save up money beforehand with odd jobs, or did you do odd jobs while on the road? A bit of both?

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Kevin @ 10:11

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I did odd jobs before I left. I was traveling in Asia at a time when the price differential was so great, that it actually made sense for me to fly back on a charter flight to the US, and work for four or five months. I worked, basically, odd jobs. I worked from working at a warehouse packaging athletic shoes, working in a technical sense of a … it’s really just hard to describe, but it was a photography-related job where we’re reducing printed circuit boards down to little sizes to be shipped off to be printed … and driving cars, to whatever else I could find. That, at that time, made more money- I could live off of- I could live probably two years from those couple months of work.

I didn’t really work while I was traveling until I got to Iran in the late ’70s, and there was a very high-paying job which was teaching English to the Iranian pilots who worked for the Shah. But I had sworn I was never going to teach English, so I actually got a job in Bell Helicopter, who was teaching English to the pilots. But my job was running a little newsletter for the American community there. I worked there until I was thrown out by the coup. That was another story.

Tim Ferriss speaker headshot

Tim @ 11:38

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Now, just a couple of comments. Number one, for those people listening who are saying to themselves, already perhaps creating reasons why they can’t do what you did now, due to different economic climate or whatnot … it is entirely possible to replicate what you did. You just have to choose your locations wisely, for that type of …

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Kevin @ 11:56

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Yeah, absolutely.

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Tim @ 11:57

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I should also just mention to people that part of the reason I’m so attracted to stoic philosophy, whether that be Seneca or Marcus Aurelius, is exactly because of the practice of poverty. Not because you want to be poor, but so that you recognize not only that you can subsist, but then you can potentially be content or even, in some cases, be more content with a bare minimum. For people who are more interested in that, I highly recommend a lot of the stoic writings, and you can search for those on my blog and elsewhere. But-

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Kevin @ 12:29

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Let me just add to that. There’s actually a new-age version of that that was sort of popular a generation ago, and the search term there is “volunteer simplicity”.

Tim Ferriss speaker headshot

Tim @ 12:38

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“Volunteer simplicity”?

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Kevin @ 12:39

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Right. The idea is, poverty is terrible when it’s mandatory, when you have no choice, but the voluntary version of that is very, very powerful. I think attaching names sometimes to things makes it more legitimate, but imagine yourself practicing voluntary simplicity. That, I think, is part of that stoic philosophy, but there’s a whole movement … a lot of the hippie drop-outs were kind of practicing a similar thing, and there was a whole “best practices” that resolved around that. You can make up your own. But I think it’s, to me, an essential life skill that people should acquire. I mean, when you go backpacking and stuff like that, that’s part of it. That’s the beginnings of trying to understand what it is that you need to live as a being, and you can fill that out in any way you want, but that’s a good way to experiment.

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Tim @ 13:32

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Now, you have become certainly a world-class packager of ideas, but also at synthesizing and expressing these ideas. I love your writing, I’ve consumed vast quantities of it. (laughs) In fact, I’m here right now on Long Island where I grew up, and I used to sneak into my parent’s shed to read old editions of the Whole Earth Catalog for inspiration. It was, I suppose, the equivalent of my internet at the time. (laughs) And from that, all the way to 1000 True Fans, which of course you know I shout from the rooftops for people to read. How did you develop that skill of writing and communicating? A lot of people associate that with schooling, but it doesn’t appear to be the source for you.

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Kevin @ 14:18

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Yeah. In high school, I would call myself a very late bloomer. I don’t recall myself having a lot of ideas. There were a lot of other people and kids in my high school that I was very impressed with, because they seemed to know what they thought and were very glib and articulate, and I wasn’t. I was a little bit more visual in that sense. I was trying to decide whether to go to art school or to MIT, because I was really interested in science.

I set off to Asia as a photographer, so it was basically no words at all, it was just images. And as I was traveling and seeing these amazing things … I mean, again, I want to emphasize that this was sort of a … for me, I grew up in New Jersey, I had never left New Jersey, we never took vacations. It’s hard to describe how parochial New Jersey was back in the 1960s. I never ate Chinese food, I never had … I mean, I never saw Chinese. It was a different world. And then I was thrown into Asia and it was like, “Oh my gosh,” everything I knew was wrong. So that education was extremely, extremely powerful. I think that that gave me something to say, and I started writing letters home, trying to describe what I was seeing. I had a reason to try to communicate. That was the beginning of it, but even then, I don’t think I really had much to say.

It wasn’t really until the internet came along, and I had a chance to go onto one of the first online communities in the early ’80s, and for some reason …

Tim Ferriss speaker headshot

Tim @ 16:01

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The early ’80s? That is definitely … early days.

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Kevin @ 16:04

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Yeah, it was in 1981. These were private, it wasn’t the wide-open internet. These were little experiment- in fact, it was New Jersey Institute of Technology in Rutgers that had this experimental online community that I got invited on … We can talk about how that happened, but it was just luck and a friend. And I found that there was something about the direct attempt to just communicate with someone else in real time, just sending them a message or something, that crystallized my thinking. What it turned out, is-

Tim Ferriss speaker headshot

Tim @ 16:38

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How did it crystallize your thinking? Not to interrupt, but was it the immediate feedback loop?

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Kevin @ 16:43

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It was the idea that … teachers have since done a lot of studies where they had kids write an essay on something, an assignment, and then they would also be instructed to write some e-mail to a friend or something. Then they would grade both of the compositions, and they would find that, inevitably, the e-mail that the kids were writing was much better writing. Because when you’re trying to write a composition, we have all these attitudes, or expectations, or there’s kind of this “writer-ly sense”. There’s all this other garbage and luggage and baggage on top of that. But when we’re just trying to send an e-mail, we’re just directly trying to communicate something. We’re not fooling around, we’re not trying to make it …

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Tim @ 17:30

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Literary.

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Kevin @ 17:31

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Literary, all that. Just direct stuff. So the writing there was always much more direct and concrete. That’s the usual thing that happens when you’re trying to write, is you’re not concrete enough. But when you e-mail, it’s all concrete.

So it was getting out of the whole writer-ly stuff and just pure, concrete communication, that really made it for me. What I discovered, which is what many writers discover, is that I write in order to think. It was like, “I think I have an idea,” but when I begin to write it, I realize, “I have no idea,” and I don’t actually know what I think until I try and write it. Writing is a way for me to find out what I think. It’s like, I don’t have any ideas, it’s true, but when I write, I get the ideas. That was the revelation.

So by being forced to communicate online, there was none of this expectation. It was just like, “OK, just write an e-mail. I can do that. I don’t have to write an essay, I don’t have to write something nice. I’m just going to write 140 characters. I can do that.” But while I was doing that, I had an idea that I didn’t have before. It was like, “Oh my gosh, this is an idea-generation machine, it’s by writing. It’s not that I have these ideas and I’m going to write them down. No, no. I don’t even have them until I write them.”

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Tim @ 18:42

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I’m so glad you brought that up, because I was just recently- a few things related to that. I was reading an interview with Kurt Vonnegut, who’s one of my favorite authors. For people who aren’t familiar, check out Cat’s Cradle perhaps, as a starting point. Hilarious guy, and he, at various points in his career, taught writing to make ends meet. And he would, number one, not look for good writers, he would look for people who are passionate about specific things.

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Kevin @ 19:07

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Yep, right.

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Tim @ 19:08

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That’s something I want to reiterate to people who don’t feel “writer-ly”, is that … go out and have the experiences and find the subjects, the things that excite you. As long as you’re true to your voice, which is related to the e-mail point … I threw out my first two drafts of, I’d say, a third of the four-hour work week, because they were either too pompous and ivy-league-sounding …

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Kevin @ 19:30

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(laughs)

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Tim @ 19:31

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Way, way, way too much. I mean, horrible. Or too slapstick, because I felt like I had to go to the other extreme. And then I sat down and I wrote as if I were composing an e-mail to a friend after two glasses of wine, and that’s how I found my “voice” so to speak.

As a side note, why - and I think this might be related - but why did you promise yourself not to teach English? I’m so curious. Because that can be very lucrative, it’s readily available … when you were traveling, why did you commit to yourself not to teach English?

Kevin Kelly speaker headshot

Kevin @ 19:58

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Yeah, it’s a good question, because there was lots of opportunities all around the world. By the way, I recommend it as a way for people to travel cheaply, if you want to support yourself, because it is a very desirable “skill”, we call it, for the moment.

I think the reason why was I felt that … I didn’t feel like I was a very good teacher, and I also felt that it was maybe a little easy? But I think the main reason was that I was having trouble imagining myself enjoying it. I just felt that I would rather try to find something else. Now, I think I did, one time in Taiwan - which as you know, has a whole cram school system - I think I substituted for a friend once. And I think that maybe confirmed my idea (laughter), that while there was sort of … you know, all I have to do is just talk, I mean, there was really not much skill involved at all. It was fun, but I didn’t feel like I was … I don’t know, I didn’t feel like I was maybe adding value or something. I came away thinking, “You know, I guess I could do this for money, but I’m not going to be happy.”

I think it was just a personality thing. I don’t think of myself as a teacher, I don’t do many workshops or classes. I think a different person might thoroughly enjoy it and I know they do and they have a great time doing it. For me, it was just … not for me.

Tim Ferriss speaker headshot

Tim @ 21:26

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Mm-hmm, got it.

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Kevin @ 21:27

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No big deal. I think this is an important thing, is that it takes a long time to figure out what you’re good for. Part of where I’m at right now and where I got eventually, was really trying to spend time on doing things that only I can do. Even when I can do something well but someone else could do it, I would try and let that go. That’s a discipline that I’m still working on, which is not just things that I’m good at, but things that only I’m good at. That was something I was sort of trying to start early on, which is like, “You know, a lot of other people can do this, and they’re happy doing it. So I want to go somewhere where it requires more of me to do, and then I’ll be happier and they’ll be happier.”

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Tim @ 22:10

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I am currently having - and I seem to have these periodically - a crisis-of-meaning phase.

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Kevin @ 22:17

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(laughs)

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Tim @ 22:18

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And I’m wrestling with this exact issue. Trying to figure out what to abandon, what to say “no” to, to refine my focus, so I can really focus on the intersection of my unique capability or capabilities, whatever that is, and a need of some type.

How did you figure that out … and maybe we could approach it from a different direction. What do you feel is your skill set or your unique skill, and how did you figure that out?

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Kevin @ 22:47

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Well, let me tell you the story of how this realization actually came to me in a very concrete way, was while I was editing Wired Magazine. Part of what Wired Magazine is about is that we would come up with ideas and make assignments to writers. Now, some of the articles in Wired would come from the writers themselves, they would approach us if they have an idea. But a lot of the articles would be assigned from editors. We’d have editorial meetings where we’d imagine this great article, and then we’d go and try and find someone to write it. And in that conversation of trying to persuade writers to write an idea that I had … it would go through a very typical sequence, where I would have this great idea, and then I would try to persuade, like, one writer, two writers, three writers, and they just didn’t think it was a very good idea. They didn’t like it, they didn’t want to do it, whatever it was. I’d kind of forget about it, but then, like, six months later it would come back and I’d say, “Oh, that was such a great idea, I really think we should do that.” And I would go again for another round of trying to persuade people, and then I’d get no takers. And then I kind of- “Oh, forget about that, it must have been a bad idea.” But then, like, six months later or a year later, it might come back, “You know, that’s still a great idea. Nobody has done that.” Then I would realize, “Oh my gosh, I need to do that!” (laughter) It was like, “I’m the only one who can see this. I’ve tried to give it away, I’ve tried really hard to give it away, I’ve tried to kill it … “

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Tim @ 24:16

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(laughs) It just keeps on coming back!

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Kevin @ 23:17

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Keeps coming back! And then I would do it and it would be one of my best pieces. So I became really an important proponent of trying to give things away first. Tell everybody what you’re doing … basically you try to give these ideas away, and people are happy because they love great ideas. You can- “Hey, do it, it’s a great idea. You should do it.” I’d try to give everything away first, and then I’d try to kill everything, like, “No, that’s a bad idea,” and then it’s the ones that keep coming back that I can’t kill and I can’t give away, that I think, “Hmm, maybe that’s the one I’m supposed to do.” Because no one else is going to do it. I mean, I’ve been actively trying to get … and then of course, if someone else is doing it, you see someone else competing or trying to do it, it was like, “Oh yeah, go ahead, do it. I’m not going to race against you. That’s crazy because there’s two of us. No, you do it.” So that generosity is actually part of this thing-

Tim Ferriss speaker headshot

Tim @ 25:15

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Your vetting process.

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Kevin @ 25:16

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Exactly. That’s when I kind of realized it.

But that doesn’t answer the question of, “Well, how do you find out what it is?” All I can say is … and I don’t want to fib, but all I can say is, it’s going to take all your life to figure that out. That is fact. Here’s what it is - figuring out is what your life is about. (laughter) I mean, that’s what life is for. Life is to figure it out, so every part of your life, every day, is actually this attempt to figure this out. You’ll have different answers as you go along, and sometimes there may be directions in that. But that’s basically what it is.

You were very transparent about confessing this, but I have to tell you that even from hanging around a lot of very accomplished people, a lot of successful people, that we would be on the covers of magazines … they also go through exactly the same questioning. No matter how big of a billion-dollar company they have, they come up to the same thing - what’s my role in all this? Why am I here, what am I useful- what am I doing that nobody else can? It’s a continuous … In fact, as we’ll come back to, being successful makes that even more difficult.

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Tim @ 26:29

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Why is that?

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Kevin @ 26:30

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Because of what I call the “creator’s dilemma”, which is very much the same thing as the “innovator’s dilemma”. It’s a true dilemma, in the sense that there’s no right answer. But the question is: is it better to optimize your strengths or to invest into the unknown, into places where you’re weak?

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Tim @ 26:56

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Or places you haven’t explored.

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Kevin @ 26:57

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Yeah. Any accountant in any business would tell you that it absolutely makes more sense to take your dollar … You’ll get a higher return by investing into what you’re good at already, whatever it is. This is pursuit of excellence, this is Tom Peters and the whole entire movement, which is you move uphill, you keep optimizing what you know. That, by far, is the sanest, the most reasonable, the smartest thing to do.

But when you have a very fast-changing landscape like we live in right now, you get stuck on a local optima, you get stuck. The problem is, is that the only way you can get to a higher, more fit place, is you actually have to go down. You actually have to head into a place where you are less optimal, you have no expertise, there’s very low margins, there’s low profits, you’ll look foolish, there’ll be failures. And if you’ve been following a line of success, that is very, very difficult to do. It’s very difficult for an organization- it’s literally almost impossible for an organization who’s been excellent and successful to do, it really is.

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Tim @ 28:16

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Which presents a lot of opportunity for the … the start-ups.

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Kevin @ 28:20

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That’s why the start-ups all start there. The reason why start-ups start is because they’re operating in an environment that no sane, big corporation would want to be in. It’s a market with low margins, low profitability, unproven, high-failure. I mean, it’s like, who wants to operate there? Nobody! The only reason why start-ups operate is they have no choice!

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Tim @ 28:40

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Right. (laughs) Yeah, that’s the gift of few options, right?

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Kevin @ 28:46

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Right, exactly. So in terms of success biting, I think you have to be unsuccessful. Who is successful, wants to be unsuccessful? It’s very, very hard to let go of that success. That’s one of the things that works against someone really continuing on this life journey of finding out what they’re really good at it. Because here’s the thing - successful companies and successful people generally try to solve problems with money. You buy solutions. And we all know that money is not the full answer for innovation. Basically, if you could purchase innovations, all the big companies would just purchase them. It’s the fact that these innovations often have to be found out without money, through other means. Again, that’s the advantage to the start-up, and it’s a disadvantage to the successful companies because they got money and they just want to buy solutions. But most of these solutions you can’t buy, you have to kind of engineer in this very difficult environment of low margins, low success, low profits, that no one really wants to be in, but the start-ups are forced to be in.

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Tim @ 29:50

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That’s also an advantage, I would think, for beginners or novices compared to experts.

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Kevin @ 29:55

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Exactly.

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Tim @ 29:56

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They have less vested identify, less inertia, to have to reverse.

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Kevin @ 30:03

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And that’s back to my suggestion in the beginning, of why slack and fooling around when you’re young is so important. Because a lot of these innovations and things are found not by trying to solve a problem that can be monetized. It’s in exploring this area without money. I mean, money is so overrated. It really …

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Tim @ 30:24

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Could you elaborate on that? Because I feel like this is a sermon I need to receive on some level.

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Kevin @ 30:29

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(laughs) There’s several things to say about. One is, obviously, if you’re struggling to pay bills and mortgages and stuff … there’s a certain amount that’s needed. But here’s the thing, accumulating enough money to do things is really a by-product of other things. It’s kind of a lubricant in a certain sense rather than a goal.

Great wealth, extreme wealth, is definitely overrated. I’ve had meals with a dozen billionaires, and they’re no diff- I mean, their lives, lifestyles are no different. You don’t want to have a billion dollars, let me put it that way. You really don’t. There’s nothing that you can really do with it that you can’t do with a lot of less money. We’ll set that aside.

Even just wealth itself, in this world where there is more and more abundance … even the money for, say, middle class is less significant in a certain sense, in the sense that … maybe their status, which is really not needed, but … The things that you want to do, the things that will make you content, the things that will satisfy you, the things that will bring you meaning … can usually- got better than having money. I mean, if you have a lot of time or a lot of money, it’s always better to have a lot of time to do something. If you have a choice between having a lot of friends or a lot of money, you definitely want to have a lot of friends.

I think there’s a way even in which the technological progress that we’re having is actually diminishing the role of money. And I want to be clear that I’m talking about money beyond the amount that you need to survive, but even that reflects back to what we were saying earlier, which is probably less than you think it is, to survive.

So in a certain sense, most people see money as a means to get these other things, but there are other routes to these other things that are deeper and more constant and more durable and more powerful. Money is a very small, one-dimensional thing, that if you focus on that, it kind of comes and goes. And if you … whatever it is that you’re trying to attain, you go to it more directly through other means, you’ll probably wind up with a more powerful experience or whatever it is that you’re after. And it’ll be deeper, more renewable, than coming at it with money.

Travel is one of the great examples. Many, many people who are working very hard, trying to save their money to retire so they can travel. Well, I decided to flip it around and travel when I was really young, when I had zero money. And I had experiences that basically even a billion dollars couldn’t have bought. And it’s not an uncommon sight, let me tell you, for young travelers who have very little money to be hanging out, doing something, and then there’ll be some very wealthy people on their one-week organized tour, looking at these young travelers, just saying, “I wish I had more time.” (laughs)

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Tim @ 33:33

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Yeah, I see it almost every time I go traveling. It reminds me of conversations I’ve had with Rolf Potts and also his book, Vagabonding, which I just absolutely love. It was that book and Walden that I took with me traveling when I had my own two-year or so walkabout. He points out, in the beginning of Vagabonding, that many people subscribe to the belief along the lines of Charlie Sheen’s in the movie Wall Street, when he’s asked what he’s going to do when he makes his millions and he says, “I’m going to get a motorcycle and ride across China.” (laughter) Rolf of course points out that you could clean toilets in the US and save enough money to ride a motorcycle across China. (laughs)

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Kevin @ 34:19

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Exactly.

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Tim @ 34:20

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Let me ask you, this is maybe tangentially related, but you mentioned earlier that your middle age … your middle ages- “middle ages” maybe sounds odd, but in your middle age, that’s when you optimize. And I find that horrifying on some level because I am so tired … I just turned 37 last week, and I’m really tired of certain types of optimizing, and the incremental slogging of making trains run slightly more efficiently on time. Even though, like you said, from a strictly financial standpoint, the advice that I would receive from many people and have received when I’ve asked for advice is, “Here are one or two core areas you should focus on to optimize for income.” And on the flip side, I’m tempted to approach a kind of … not “scorched earth” but “burned bridges” approach, where I somehow use creative destruction to force me into another direction, to have these new experiences that I crave so much.

And you, just for people who aren’t aware, I want to give … I remember going to the first ever quantified self meet-up, you’re part of the Long Now Foundation. You’ve experimented in so many different arenas, and have looked so far into the future, and thought on such grand a scale, I aspire to do more of that … What would be your advice to someone? I know I have dozens of friends in the same position. They’re, say, in their early- or mid-30s, in my particular peer group, and they want to explore but they’re feeling pressured to optimize this thing that they’ve suddenly found their footing with, whatever it is. Maybe they’re a venture capitalist, maybe they’re in start-up, they feel they should start a new start-up, and they want to step out of that slipstream. What would be your advice to those people?

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Kevin @ 36:06

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Well, first of all, I have to commend your honesty for this, and I will repeat that it is very, very difficult to do. I mean, I think the realization comes to people in middle age and they realize, “Oh my gosh, there’s a little bit of a routine here and I’m not really happy with that.” I think that scorched earth, that kind of, you know, “We’ll just set fire to it and we’ll walk away,” I actually have … I think we probably have a mutual friend, I won’t use his name because I don’t know how public this is, but one of his solutions was the most radical one I’ve ever heard, to force himself, was that he gave up US citizenship.

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Tim @ 36:45

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Oh, wow. Yeah, that’ll do it. (laughs)

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Kevin @ 36:49

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He was saying, “I just feel so-“ I was like, “Oh my gosh, that is so radical.” He was telling me about what is involved in that, and it wasn’t for tax purposes, because actually before you can do it, the US actually requires that you square-up on all taxes. But that was so radical, and I don’t recommend that. (laughter) That’s all I’m saying. I mean, he’s doing fine, but I’m just saying that’s unnecessary.

I think the advice is … I’m probably taking a page from yourself. I don’t think it’s necessary to … I think you can experiment your way through this, you can do this incrementally. You can take small steps and do something, and then evaluate it, test how it’s going, whether you’re getting what you want out of it, whether it’s working, and then you continue in that direction. That’s sort of the pattern of people who have second careers or “reinvent themselves”, you hear that a lot. And you can do that in a disciplined, Tim Ferriss way. I don’t think that it requires you to walk out and leave a burning pile behind. I think it’s something that you’re going to … I’m a big believer in doing things deliberately, and I think that you begin by looking at those areas that you get satisfaction out of, and those areas where … I often find that people kind of retreat back to the things that they did as kids and really, really miss, whether it’s art or other things. The truth is, you’re not really going to be able to escape all the other things you have going. And that’s a good thing because that is part of you and part of what you do well. So you’ll probably just bend in a certain direction.

I think the one bit of advice is that you can’t … it’s not going to happen overnight. It took you 37 years to get where you are, it may take you another 30 years to get where you want to go. I don’t think you should feel impatient, maybe that’s the word I’m saying, is that I don’t think you should imagine that you’ll have another hat on with a new label next year.

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Tim @ 38:48

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Just to maybe redirect that - and this may or may not be accurate - but in the process of researching for this conversation, which is an odd exercise in and of itself, given how much time we’ve spent together. (laughs) But I came across, in Wikipedia, mention of your experience in Jerusalem and deciding to live as though you only had six months left. I want to touch on that, but one of the questions that came to my mind when I turned 37 last week is, “If I knew I were going to die at age 40, what would I do to have the greatest impact on the greatest number of people?” So I find that constraint helpful and I worry that if I aim at not being impatient in that way, that I won’t - because I could get hit by a bus - that I won’t do what I’m capable of doing. Maybe you could talk about … and I had no idea, I’m not sure if you would self-describe yourself as a “devout Christian”, but that’s certainly written here. Maybe you could talk a little bit about that experience.

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Kevin @ 39:49

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Yeah. One thing I would of course warn people is that, not everything on Wikipedia is correct. (laughs)

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Tim @ 39:50

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No, that’s why I’m bringing it up. (laughs)

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Kevin @ 39:52

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But it is true that I got this assignment in Jerusalem, which, by the way, if you want to hear the full version of it, listen to one of the very first “This American Life”, which Ira Glass and I told the story for the very first time. It’s a story about how I got this assignment to live as if I was going to die in six months, even though I was perfect healthy and I knew that it was very improbable. But I decided to take the assignment seriously and that’s what I did.

My answer kind of surprised me, because I thought that I would have this sort of mad, high-risk fling, do all these things, but actually what I wanted to do was to visit my brothers and sisters, go back to my parents, help out. My mom was not well at the time. But that lasted for three months before I decided I needed to do something big. So I actually road my bicycle across the US, from San Francisco to New Jersey, where I was going to basically die. I kept a journal of that.

And that question was something that I keep asking myself now. I actually have a countdown clock that Matt Groening at Futurama was inspired and they did a little episode of Futurama about. What I did was, I took the actuarial tables for the estimated age of my death, for someone born when I was born, and I worked back the number of days. I have that showing on my computer, how many days. I tell you, nothing concentrates your time like knowing how many days you have left. Now, of course, I’m likely, again, to live more than that. I’m in good health, etcetera. But nonetheless, there’s something that really … I have 6,000 something days, it’s not very many days to do all the things I want to do.

So I think your exercise is really fantastic and commendable, and there’s two questions - what would you do if you had six months to live, and what would you do if you had a billion dollars? And interestingly (laughs), it’s the convergence of those two questions. Because it turns out that you probably don’t need a billion dollars to do whatever it is that you’re going to do in six months. So I think you’re asking the right question. The way I answer it is, you want to keep asking yourself that question every six months and really try to answer it. I try to do that on a day-by-day basis.

I learned something from my friend, Stewart Brand, who organized his remaining days around five-year increments. He says any great idea that’s significant, that’s worth doing, for him, will last about five years, from the time he thinks of it, to the time he stops thinking about it. And if you think of it in terms of five-year projects, you can count those off on a couple hands, even if you’re young. So the sense of mortality, of understanding that it’s not just old people who don’t have very many … if you’re 20 years old, you don’t have that many five-year projects to do.

So I think it is … that’s maybe part of the philosophy of thinking about our time and whether … even if you believe in the extension of life, longevity, living to 120, you still have to think in these terms of, what are you going to do if you - because you don’t know if you’ll live to be 120 - what are you doing to do if you have a year, and what would you do with a billion dollars? And what’s the intersection of those two?

End @ 42:10