The Tim Ferriss Show - Ep 25: Kevin Kelly - WIRED Co-Founder, Polymath, Most Interesting Man In The World

Episode Date: August 25, 2014

Kevin Kelly is amazing. He is a co-founder of WIRED Magazine, diverse polymath, and my nominee for the real "Most Interesting Man In The World." This is a multi-part interview. Read all about him at kk.org.Show notes and links coming soon to www.fourhourworkweek.com/podcast***If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!For show notes and past guests, please visit tim.blog/podcast.Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Interested in sponsoring the podcast? Visit tim.blog/sponsor and fill out the form.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissFacebook: facebook.com/timferriss YouTube: youtube.com/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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the number one, drinkag1.com slash Tim. Last time, drinkag1.com slash Tim. Check it out. Hello, ladies and gentlemen, this is Tim Ferriss, and welcome to another episode of The Tim Ferriss Show. I'm going 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. Quote, 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.

End quote. I have a 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. So 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. And 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 nonprofit aimed at cataloging and identifying every living species on earth. And in all his spare time,

he writes bestselling 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. This is part one. I hope you enjoy it. You can find all links, show notes, and so on. Once we complete the entire series at fourhourworkweek.com forward slash podcast.

You can also find all previous episodes I've done in this podcast, fourhourworkweek.com forward slash podcast, all spelled out. And without further ado, please enjoy. And thank you for listening. At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question? Now would seem an appropriate time. What if I did the opposite?

I'm a cybernetic organism, living tissue over metal endoskeleton. The Tim Ferriss Show. Kevin, thank you so much for being on the show. It's my honor. And 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? These days, my stock answer is that I package ideas into books and magazines and websites. And I make ideas interesting and pretty.

Well, 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. And is it true that you dropped out of college after one year? Yeah, I'm a college dropout. And actually, my one regret in life is that one year that I gave. Oh, no kidding. No kidding. Yeah, I wish I had just even skipped that. But I do understand how college can be useful to people. And my own children have gone through.

But for me, it was just not the right thing. And I went to Asia instead. And 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. And 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. Wow. Which job was that? I worked for a non-profit at $10 an hour, which was the whole worth catalog, which had been kind of a lifelong dream. If I said, if I'm going to have a job, that was the job I want. It took me a long time to kind of 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 I hired a lot of people who were coming right out of college. They were internets and they would do the intern thing and then they were good and we would hire them, which meant that basically, you know, after 10 years, whatever it was, they were, 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 and i just really i really recommend slack i'm a big believer in in this

thing of kind of doing something that's not productive you know 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 kind of extreme satisfaction. It's a time to kind of try stuff. Explore the extremes exactly explore the possibilities and there are so many possibilities and there's more every day and and you don't want it's called premature optimization you you know you really 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. Yeah, that might turn into a therapy session for me at this precise moment in time, in fact. Yes, exactly. But when you are

exploring that slack, I would imagine many people feel pressured, whether it's internal pressure or societal familial pressure, to get a real job, to support themselves. And a lot of the decisions are made out of fear. They worry about being out on the streets or it's a nebulous terror or anxiety. How did you support yourself, for instance, while you were traveling through Asia when you left school? I totally understand this anxiety and fear and stuff. But here's the thing. I think one of the many kind of 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 is traveling through time in the sense of learning how little you actually need to live, not just in kind of survival mode, but kind of in a contented mode. And I learned that pretty early by backpacking and doing other things, and especially in Asia,

was I could be very happy with very, very little. And you could go onto websites and stuff and look at sort of like the minimum amount of stuff, food, say, that you need to live, your basic protein and carbohydrates and vitamins, and how much you 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. And 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 worst came to worst, you could keep going at a very low rate and be content. And so that gives you the sort of confidence to take a risk because you say,

what's the worst that could happen? Well, the worst that could happen is that I'd have a backpack and a sleeping bag and I'd be eating oatmeal and whatever, and I'd be fine. And 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 definitely i did that's basically what i did it was you know 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 and did you save up money beforehand with odd jobs or did you do odd jobs while on the road, a bit of both? 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 U.S. and work for four or five months. And I worked basically odd jobs. I worked from working in a warehouse, packaging athletic shoes, working in a kind of technical sense of a – it's really just hard to describe, but it was kind of a photography-related job where we were reducing printed circuit boards down to little sizes to be shipped off to be printed and driving cars to whatever else I could find. And that, at that time, made more money. I could live off of, I could live off probably two years from those couple months of

work. So I didn't really work while I was traveling until i got to iran in the late 70s and there there was a very high paying job which was teaching english to the iranian pilots who worked for the shah but i had sworn there was never going to teach english so i actually got a job in bella helicopter who was teaching english to the pilots. But my job was running a little newsletter for the American community there. And I worked there until I was thrown out by the coup. That was another story. Why did that? Now, just a couple of comments. So 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 differential. And 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. So 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 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. Volunteer simplicity. Right. And so the idea is poverty is terrible when it's mandatory, when you have no choice, but a volunteer version of that is very, very powerful. And I think attaching names sometimes to things, it makes it more legitimate, but imagine yourself practicing voluntary simplicity. And that I think is part of that stoic philosophy, but there was a whole kind of a movement. A lot of the hippie dropouts 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 skill that

life skill that people should acquire. And 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, you know, as a being. And you can fill that out in any way you want, but that's a good way to experiment. 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. In fact, I'm here right now on Long Island where I grew up, and I used to sneak into my parents' shed to read old editions of the Whole Earth Catalog for inspiration. It was the, I suppose, the equivalent of my internet at the time. And from that all the way to 1,000

True Fans, which of course, you know, I sort of 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. Yeah. So 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. So 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'd 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 saw Chinese. It was a different world. And then I was thrown into Asia, and it was like, extremely powerful. And I think that that gave me something to say. And I started writing letters home and trying to describe what I was seeing. And so I had a reason to try to communicate. And 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 into one of the first online communities in the early 80s. And for some reason... The early 80s, that is definitely early days. Yeah, in 1981. And so these were private. It wasn't the kind of wide open internet. These were a little experimental.

In fact, it was New Jersey Institute of Technology in Rutgers that had this experimental online community that I got invited on. And 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. So what it turned out is- How did it crystallize your thinking? Just not to interrupt, but was it the immediate feedback loop?

It was the idea that they have since, 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 email to a friend or something. And then they would grade both of the compositions. And they would find that inevitably the email that the kids were writing was much better writing because when you're trying to write a composition there's all these you know we have all these attitudes or expectations or there's there's kind of a writerly sense there's there's all this other garbage and luggage and baggage on top of that but when we're just trying to send the email we're just we're directly trying to communicate something we're not fooling around we're not trying to be something. We're not fooling around. We're not trying to make it – Literary.

Literary. We're just direct stuff. And 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're email, it's like all concrete. And so it was getting out of the whole kind of writerly stuff and just pure concrete communication that really made it for me. And 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 to write it. So writing is a way for me to define out what I think. It's like, I don't have any ideas. That's true. But when I write, I get the ideas. And that was the revelation. And so by being forced to communicate online and there was none of this expectation, it was just like, okay, just write an email. 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. And so 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 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. So that's, that's something I want to reiterate to people who don't feel writerly is that go out and have the experiences and find the subjects, the things that excite you. And as long as you're true to your voice, which is related to the email 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, 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 email 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? Yeah, it's a good question because there's lots of opportunities all around the world. And 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. And 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 a friend i substituted for a friend once. And I think that maybe confirmed my idea that while it was sort of like, you know, all I have to do is just talk. I mean, there's 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. So 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 the personality thing. I don't think of myself as a teacher. I don't do many workshops or classes.

So 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. Got it. No big deal. I think this is an important thing is that, you know, it takes a long time to kind of figure out what you're good for. And 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. And even when I could do something well, but someone else could do it, I would try and let that go that 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 so 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 don't want to go somewhere where it requires more of me to do and then i'll be happier and they'll be happier. 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? Well, let me tell you the story of how this realization actually came to me in a kind

of a very concrete way was while I was editing Wired Magazine. And so 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 and say, I have an idea. But a lot of the articles would be assigned from editors. We'd have editorial meetings where we'd kind of 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, they go through a kind of a very typical uh sequence

where you know i would have this great idea this is a great idea and and then i would try to persuade like one writer two or three writers and it just you know they didn't think it was a very good idea they didn't like it they didn't want to do it whatever it was and then i'd kind of forget about it but then like you know six months later he would come back and say 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'd go, oh, forget about that.

That must have been a bad idea. But then six months later or a year later, it might come back. That's still a great idea. Nobody has done that. And then I would realize, oh, my gosh. I need to do that. It's like I'm the only one who can see this. I've tried to give it away. I have tried really hard to give it away. I've tried to kill it. It just keeps on coming back.

Keep coming back. And it's like, okay. And then I would do it and it'd be one of my best pieces. And so it was this idea of like, 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. And you're like, hey, yeah, do it. It's a great idea.

You should do it. And so I try to give everything away first. And then I try to kill everything. It's like, no, that's a bad idea. And then it's the ones that keep coming back that i can't kill and they can't give away that think maybe that's the one i'm supposed to do because no one else is going to do it i mean i've been 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's like oh yeah you go ahead do it i'm not going to race against you yeah that's crazy because there's two of us you know you do it and so um so that that generosity is actually part of this your vetting

process exactly and so 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 and all i can say is you know and i don't want to be flip, but all I can say is it's going to take all your life to figure that out. In fact, here's what it is. Figuring out is what your life is about. I mean, that's what life is for. Life is to figure it out. And then so every part of your life, every day is actually this attempt to figure this out. And you'll have different answers as you go along. And sometimes there may be directions in that. But that's basically what it is.

And 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. I mean, no matter how big of a billion dollar company they have, they come up to the same thing. Well, what's my role in all this? Why am I here? What am I useful? What am I doing that nobody else can? And it's a continuous, in fact, as we'll come back to being successful makes that even more difficult why is that because of the uh what i call the creator's dilemma which is very much the same thing as the innovator's dilemma which is that it's a true dilemma in fact in the sense that there's no right answer but the question is is sort of is it better to optimize your strengths or to invest into the unknown, into places where you're weak? Or places you haven't explored.

Yeah. Any accountant in any business will tell you that it absolutely makes more sense to take your dollar because you'll get a higher return by investing into what you're good at already, whatever it is. It's the pursuit of excellence. This is Tom Peters and the whole entire movement, which is you move uphill, you keep optimizing what you know, and 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. And the problem 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 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. Which presents a lot of opportunity for the startups. The reason why startups start is because they're operating in an environment that no sane big corporation would want to be in. It's because they're operating in an environment that no sane big corporation would want to be in. It's a market. It's low margins, low profitability, unproven, high failure. I mean, it's like, who wants to operate there? Nobody. The only reason why startups operate is

they have no choice. Right. Yeah, it's the gift of few options, right? Right, exactly. So in terms of success binding, 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. And so 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. Because here's the thing is that 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 that these innovations often have to be found out without money through other means. Again, that's the advantage to the startup, and it's a disadvantage to the successful companies because they've 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 startups are forced to be in.

That's also an advantage, I would think, for beginners or novices compared to experts. They have less vested identity, less inertia to have to reverse. And back to my suggestion, the meaning 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 – Could you elaborate on that? Because I feel like this is a sermon I need to receive on some level. There's several things to say about it. 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 is that accumulating enough money to do things is really a byproduct of other things. It's a lubricant in

a certain sense rather than a goal. And great wealth or extreme wealth is definitely overrated. I've had meals with a dozen billionaires, and their lives, lifestyles are no different. Their billions, 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. I will set that aside.

But 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 there's 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. And so 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. And so 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 what we were saying earlier, which is probably less than you think it is that you need to survive.

And 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. So money is this sort of very small, one-dimensional thing that if you kind of 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.

And so travel is one of the great examples, which is many, many people who are working very hard trying to save their money to retire someday to 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 kind of travelers who had very little money to be hanging out doing something, and there would be some very wealthy people on their one-week organized tour looking at these young travelers just saying, I wish I had more time. Yeah, you see it every, well, I see it almost every time I go traveling. And it reminds me of conversations I've had with Rolf Potts and also his book Vagabonding, which I just absolutely love. And it was that book and Walden that I took with me traveling when I had my own

two year or so walkabout. And he points out in the beginning of Vagabonding that many people subscribe to the belief along the lines of Charlie Sheens 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. And Rolf, of course, points out that you could clean toilets in the US and save enough money to ride a motorcycle across China. Exactly. And let me ask you, this is maybe tangentially related, but you mentioned earlier that your middle age is, middle age 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 meetup. 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. You know, I aspire to do more of that. What would be your advice to someone? And 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 that maybe they're a venture capitalist, maybe they're in a startup, they feel they should start a new startup. And they want to step out of that slipstream. What would be your advice to those people? 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 that 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 kind of scorched earth, 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.

Oh, wow. That'll do it. He was saying, I just feel so,. citizenship. Oh, wow. That'll do it. It was like, he was like saying, I just feel so, you know, and it was like, oh my gosh,

that is so radical. And 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 U.S. actually requires that you square up on all taxes. Right.

It was like, but that was so radical. And I don't recommend that. That's what I'm saying. I mean he's doing fine, but I'm just saying that's unnecessary. But I think the advice is – I'll be taking a page from yourself. I don't think it's necessary to – I think you can experiment your way through this. I mean 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. And that's sort of the pattern of people who kind of, you 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 kind of 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 kind of things that they did as kids and really, really miss, you know, whether it's art or other things. And the truth is that 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, you know, bend in a certain direction. And I think the one bit of

advice is that you can't, you know, it's not going to happen overnight. It's going to be, it took you 37 years to get where you are. It may take you another 30 years to get where you want to go. And 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. Just to maybe redirect that, and this may or may not be accurate, but in the process of researching for this conversation, which is sort of an odd exercise in and of itself, given how much time we've spent together, but I came across in Wikipedia mention of your experience in Jerusalem and deciding to live as though you only had six months left. And 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. And 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. Yeah. So, yeah, one thing I would, of course,

warn people is that not everything on Wikipedia is correct. No, that's why I'm bringing it up. But it's 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 Lives, which I – an Ira Glass. And I told the story for the very first time. And 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 perfectly healthy and I knew that it was very improbable. But I decided to take the assignment seriously, and that's what I did. And my answer kind of surprised me because I thought that I would kind of 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 with them. 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 rode my bicycle across the U.S. from San Francisco to New York where I was going, New Jersey, where I was going to basically die. And 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 on Futurama about.

And 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. And I have that showing on my computer how many days. And 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, et cetera. But nonetheless, there is something that really,

you know, I have 6,000 something days. It's not very many days to do all the things I want to do. And so I think your exercise is really fantastic and commendable. And there's two questions. What would you do if you had six months of living? What would you do if you had a billion dollars? And interestingly, 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. 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 kind of a day-by-day basis.

I learned something from my friend Stuart 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 of hands for even if you're young. And so the sense of mortality of understanding that it's not just old people who don't have very many, you know, you're 20 years old, you don't have that many five-year projects to do. And 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 going to do if you have a year and what would you do with a billion dollars and what's the intersection of those two? If you want more of the Tim Ferriss show, you can subscribe to the podcast on iTunes or go to 4hourblog.com, where you'll find an award-winning blog, tons of audio and video interview stories with people like Warren Buffett and Mike Shinoda from Linkin Park, the books, plus much, much more. Follow Tim on Twitter at Twitter.com slash T Ferris. That's T-F-E-R-R-I-S-S.

Or on Facebook at Facebook.com slash Tim Ferris. Until next time, thanks for listening.