I had an honor of chatting with Kevin Kelly, Senior Maverick of Wired magazine, which he co-founded in 1993, and served as its Executive Editor for its first seven years. He has also been a writer, photographer, conservationist, and student of Asian and digital culture. If up to this point you thought Kelly is wearing a lot of hats, wait until I add more to the list of things he’s involved with.

He co-founded the All Species Foundation, a non-profit aimed at cataloging and identifying every living species on earth, as well as, The Rosetta Project, which is building an archive of ALL documented human languages. Kelly is also on the board of the Long Now Foundation, which hopes to provide a counterpoint to today’s accelerating culture and help make long-term thinking more common.

It’s no wonder Tim Ferriss called Kevin Kelly the Most Interesting Man In The World. In fact, he has so much depth and insight, that I had to divide our conversation into two parts. 

Lesya:   Thank you so much for this interview. This means really a lot to me. I’ve read a lot of your interviews and I’ve been just blown away by the amount of knowledge and the interesting ideas you have. I wanted to talk to you about it for my blog and help my readers a little bit. My first question is, being the Co-Founder of Wired, you probably love technology. Do you live and breathe it and, if so, when did that fascination begin? Do you have a point in time when you knew that that was what you really wanted to do in life?

Kevin:   I don’t think there was a moment when I decided to do what I’m doing now. I think it was a very slow evolution. I started off as a photographer. I’m a college dropout and I went to Asia to photograph the disappearing cultures of Asia. I was really focused on a very visual record. I wasn’t doing any writing.

I came back and started to write about my travels. As part of that, I got invited onto one of the very earliest online services in 1981. I started to write about that as if it was another foreign country. As if I was a tourist visiting a place.

When I was online, I became very interested in what I was seeing and, I think, maybe that was the beginning of paying attention to what we would now call technology. I was hired at a magazine and I started to write more about the online and the magazine itself. Started early online venue called The WELL. It became more and more technological in that sense.

Lesya:   What was it on the internet that really attracted you and you decided that that’s the thing you need to do and get involved with?

Kevin:   The initial marvel was: you had people who could gather together with shared interest who were living in very distant parts of the world. Who would probably very unlikely ever get together in real life because there weren’t that many of them in the same spot. There was this meeting of mine that was made possible by this technology that was very thrilling to me. It was like being at a coffee house in Europe when people just kind of drop in and it was a very intellectual conversation. It’s really sort of like that; like you actually could recreate a hangout place, a bar for writers or something that just would be too difficult to do in real life today. The attraction was the other people. The attraction was, again, the quality of the shared mind and the shared interest. Of course, this is an experience that is rediscovered again and again by people who have very peculiar and specific interest and they need the two other or the ten other people in the world just like them online. They fall in love with the technology because it allows them to do that.

Lesya:   With the level of social media, the level of connectivity we have today, do you think that quality of the human interaction actually increased? Did it decrease and it became way too noisy and lost its original meaning?

Kevin:   No, I think it increases. It gets better. People can be distracted. They can certainly overshare and get exhausted but we still have the option of the other face to face meetings. It’s an additive. It’s another option that did not exist before that’s added to our old ways of meeting. I think, it is a positive and people will go online, and they’ll meet online in different ways. If one way gets too tiring or not productive enough, people will retreat from it but they usually will return later on, and try again, maybe with different parameters. I mean, there are very few people that actually live completely offline. It’s very, very rare. People take vacation from it, which is fine and good. Maybe they alter how they use it, which is fine and good. Overall, I think, it’s an additional way to be social.

Lesya:   Since my blog is all about millennials and entrepreneurs, I’ve got to ask you about being a college dropout, and you’ve already mentioned that too. I’ve also read in your other interviews that you got your first real job at the age of 35. Clearly, it worked out in your favor and you were able to achieve success. Can you speak and share some ideas on how to recognize the feeling of, “I don’t need a degree to succeed” versus “I don’t want to go to school because I’m not interested in succeeding?” I think there’s a really thin line and people feel strongly about it on both sides of the coin, especially these days. If you look at Mark Zuckerberg or Bill Gates, a lot of people decide that maybe college is not for them. Can you speak to that a little bit? How do you recognize whether it’s just being slackish or is it, you’re so focused on something else that college will not give you the tools you need for it?

Kevin:   I don’t know if I have a test for someone to determine whether or not they should go to college. I can tell you what I told our own three kids, which is they have the options of going to college or doing a project. If they’re going to do a project, we would support them in doing the project, but they have to have a structured alternative. They couldn’t just sit around and play video games or whatever. If they couldn’t think of something good and productive to do, then they would have to go to college. All three of them went to college, because they didn’t have really something else that they wanted to do.

I had something else that I wanted to do and so maybe that is the test. Is there something that you feel compelled that you need to do right now or not? If you don’t know, if you don’t have something, you don’t know what to do, then college, if you can afford it, seems like a good thing to do. These days, the affordability is a huge thing. I think, going into debt to go to college really changes the equation. I think that if you need to go on a debt to go to college, then my recommendation is that you take some gap years and you try working. You try some things first so that you have a very clear idea about why you’re in school.

It doesn’t mean that you have to be there to just get a career but you should have a clear vision. If you’re going into debt, you really have to have a clear idea about why you’re going to college. That’s all I would say. The thing is, it’s a serious thing to take on that kind of debt.

Lesya:   I see, but I feel like for a lot of people, going to college and taking on that debt still feels like a much safer option than going out and pursuing your dreams and working on your own ideas. I think there’s still a huge fear associated with just, “What if this doesn’t work out and it fails and then I also missed out on college?” Do you have any tips on how to overcome that fear?

Kevin:   I don’t think college is the safest option. I think the time to try things that are high-risk is really in your early 20s. I think taking time off after high school or before college is a great idea. If you spend some time trying to travel, maybe earning your way while you travel, is really huge. If I had my way, I think the U.S. should institute a two-year mandatory national service. You could complete that national service for everybody without exception. Either in the military, or in the PeaceCorp, or in some kind of volunteer organization overseas, and the country would support you for two years. I think nothing would transform the youth of this world and our own country so much as if everybody had a chance to serve or to travel. I think even without that national program, spending a couple of years on your own just exploring is probably better than college in many ways. Not as expensive and would really help prepare someone to go onto college. If you are forced to put yourself on the line, if you do that and it’s a small risk but potentially high long-term yields.

Lesya:   Can you specify what kinds of yields do you think people get from traveling and exploring?

Kevin:   It’s a very long list. One of which is, keeping your mind nimble. Confronting otherness. Learning how to trust strangers. Seeing how the world really works. Understanding that there’s other way to do things. Encountering oppositions. Seeing your own origins in your own country in a different way. I mean, it’s a university into itself.

Lesya:   I definitely agree. I want to switch gears back a little bit to the Wired. You’ve built probably the most rad and the most influential magazine in this business, in technology space especially. How did you make it happen? Share your secrets with us. How did Wired grow to where it is today?

Kevin:   First of all, I have to be very, very clear that I was a part of the team Wired. The actual origin of the magazine is due to two people, Jane Metcalfe and Louis Rossetto, who worked for easily a full year on the prototype before I arrived, before they hired me. The journey from the original first ideas to now is full of many twists and turns, and many near-death experiences (like with many startups) and so there were probably three or four times when we were convinced that it was going to die the next day.

These kinds of things only look like they were inevitable in retrospect but, at the time that it was happening, it was a very unlikely success. My involvement came when I saw the prototype. They were looking for an editor, and I had earlier known about them and encouraged them to start a magazine. I didn’t think it was very likely to succeed, but I’d changed my mind when I saw the prototype.

I think that it succeeded for a couple of reasons. One was because Louis is incredibly stubborn. He’s the right kind of entrepreneur who basically would almost die in order to make this thing work, who would never give up. Then the second reason is because we were lucky, because we started this thing exactly the right moment. If it had started two years earlier, it would have been too early. Two years later, it might have been too late. It was the right thing at the right time. Then the third reason, I think, is because the five or six people who were starting the magazine, we were all basically unemployable. We were basically a lot of –  I don’t know what you call it –  renegades who had avoided working for big companies. Who were not somewhat in the magazine industry and so we could take a very fresh look at it. We could do something that was necessarily very different from anything else at the time in part because we came from outside of the established magazine world. There was this convergence of a bunch of talented people who would not have been hired by any other magazines except their own magazine. In fact, I’m not even sure if we would have been hired by Wired today. We would probably not make the cut.

Lesya:   That’s funny. Just that you mentioned that you were unemployable but also, in some interviews, I’ve read about the quality of your personality that is really rare today. That you will only do things you like and the things you want to do that will make you happy. In Tim Ferriss’ interview, I read that you did not want to teach English in China because that was not something you were liking. Can you speak on the importance of doing what you like and what makes you happy instead of trying to jump on anything that will pay? Because, I think, that’s a huge problem for a lot of people these days. To get the job just for the fear of failure. Fear of bills and all of that stuff. Can you speak on the importance of it on how to make sure that that skill or the personality quality stays with you through your whole life?

Kevin:   I want to be clear that I’m not advocating the idea of, follow your passion, because, I think that, when you’re setting out in the beginning, most people including maybe even myself, don’t really know exactly what we’re good at. Maybe we may not even know what we’re passionate about. I certainly did not think that I would ever end up writing for a magazine or becoming a writer for instance. That was not ever my dream. That was not my passion. I think there’s two other ways to frame this, which is what I think the best approach is to become master of something. To become really, really good at something and almost anything. You use that mastery to move yourself in a direction of constantly doing things that you enjoy more. Through that mastery, you’ll eventually come to master a passion. The other way to frame the same thing is that you start to do something you become really good at and you bring your passion to it.

I think it’s too much of a demand to ask young people to divulge a life to passion because most people, including myself, don’t really know what you’re really, really ultimately good at. That paralyzes people. It’s not that you should necessarily do anything that comes up and just kind of trudge along and put your head down and just do boring stuff.

What you want to do is you want to pick something that you can get better at every day. Something that you can tolerate enough to keep improving day, after day, after day, until you really become so good at it. Then you feel you’ve mastered it and can use that as a platform to try and move as you are rewarded for that mastery. Move it in the direction of doing more of the work that you like to do, that you have mastered. Eventually, if you keep mastering, keep getting better, you’ll be able to move yourself into an area where you master something that you have passion for. It’s a way of finding your passion because I think if you just wait around, you’re just not gonna get that passion just by hoping that it comes.

Lesya:   On that note, how do you figure out what that skill is that you should pursue? How do you focus and truly zero in? Because I think a lot of people have okay talents in a lot of areas and then they get pulled into different directions because they’re not sure what they like, what they’re passionate about, what their good at.

Kevin:   Interesting. Don’t try to worry about it. You don’t have to worry, you just take something. Anything. It doesn’t matter what it is. Something that you can master. Again, you’re not trying to find out in the beginning what it is that you like. That’s not the question you’re trying to answer. It’s what can I become master of? What can I do on a world class level? Your job is simply to pick anything and say, “I’m going to just become better at this every day and I will use that thing to figure out what I like.” You don’t have to love it in the beginning. All you want to know is, “Am I capable of getting better at this tomorrow?”

Lesya:   My other question from this is that, these days especially, who people want fast results, grow more and more impatient. They want to achieve success fast, or lose weight fast, or be the best in the industry really fast. What do you tell those people who are growing really impatient? Even with themselves, if they don’t succeed right away.

Kevin:   Patience is a virtue. I think the wisdom of age is that you just have to be patient and keep getting better. See if you can find the joy in improving what you’re doing.

I mean, I think, losing weight, I have to say is a very different thing than when we’re talking about in terms of career advice. If you’re just talking about ways to improve yourself, that’s really different than the question of how do you find meaningful work. I want to separate those two tasks.

Lesya:   What I mean is that by looking at people, for example, in blogging industry, there is a lot of six-figure bloggers that seem they just became an overnight success. There are those startups, like Airbnb or Uber, that have been around for ten years  prior to their big moment and their big breakthrough, but for outsiders, it just looks like these startups became an overnight success. I think, people these days are really getting tired and really tough on themselves if they are not feeling like they’re an overnight success. Do you know what I mean?

Kevin:   Yeah, I think I do understand that. I think part of that is shifting or modifying or using your ideas of success. I have to say that six-figure income, to me, is never been a measure of success. The first thing I would counsel is try not to frame your success in terms of money because that’s very, very distracting. I will also say, from own experience, I’m very suspicious of numbers like that.

I think the first thing I would counsel is, frame your success in a different way. Secondly, for a long time, your success has to be measured by the work itself in some capacity. If your job is to become a world class at it then your success should be, “Well, am I world class?” World class does not necessarily mean, you have a million followers.

I mean, I wrote this piece about the 1,000 true fans which is that you don’t actually need a million followers. You need some true fans and you may not need that many of them. There’s also, by the way, a difference between making a living versus making a fortune. That’s another thing about success. There are some people who, their definition of success is a fortune. I think that’s also, when you’re young especially, a total misguided definition. I think making a living is a much more long-term sustainable and rewardable definition of success. Part of my counseling would, aside from being patient, is that, “Well, let’s talk about your definition of success.”

Lesya:   Do you think it’s better to define success in terms of skills and accomplishments?

Kevin:   Right. There have been a lot of studies about what drives people to do things and I think, again and again, for your success to be lifelong, your drive has not to be money. It has to be other intangible motivations that sustain you. If you begin early with running on those motivations then, as they say, the money will come. At least enough money for a life, not necessarily a fortune.

Find Kevin Kelly on Facebook and Twitter.

Also get his latest book The Inevitable: Understanding the 12 Technological Forces That Will Shape Our Future.

Loved this interview? Sign up to receive new episodes!