#127 - The Power of Failure with Kevin Kelly, Publisher and Founding Editor of Wired
E127

#127 - The Power of Failure with Kevin Kelly, Publisher and Founding Editor of Wired

Erin - 00:00:26: Hello, everybody, and welcome back to Awkward Silences. Today, we're going to be here in a minute, you'll see, with Kevin Kelly, who is the Founding Editor of Wired. He describes himself as the Senior Maverick of Wired. Fun fact about JH and I, we did this, you know those personality tests you do at work, we did one of those and it plots you on a thing and gives you a name, and we both got Maverick. So we've got three Mavericks here, but maybe we're Junior Mavericks. Mavericks in training. So this should be a fun one, no rules.

JH - 00:01:07: Yes, and I think everyone knows the name of the podcast is Awkward Silences, today, we'll have a bit of an awkward transition. Unfortunately, we did lose the first couple of minutes of our recording with Kevin somehow, which was a bit of a bummer. But as Erin called out, it was a really special guest for us to get on. It was really cool to read an advanced copy of his book, I think we both had a lot of great takeaways from it. The majority of the conversation is still here, we'll jump right into it, but we are going to just, kind of, recap a little bit of how we kicked the conversation off to provide some context, and then we'll jump right in with Kevin.

Erin - 00:01:35: Yeah, so from Awkward Silences to Awkward Transitions, we'll get there. But the name of the book is “Excellent Advice for Living”, and it's a great coffee table book to revisit over the years, full of, what it sounds like, excellent advice for living from someone who has done some living himself. There's general advice about life, of course, but a lot of it is actually really applicable to research, to careers, to integrating your life and your career. So basically, we went through and we chatted about all of those things.

JH - 00:02:07: Yeah, totally. So, we highlighted our favorite passages and we pulled them out and we spoke to Kevin about them to get some more context about where they came from and how he thinks about them, and then the first one that we started discussing is the one that we lost. So, Erin, do you want to just recap that and we’ll jump in?

Erin - 00:02:19: Yeah, sure. So the Rule of 7 in research, which is that you can find out anything if you're willing to go through 7 levels. So he describes it as, “if the first source you ask for information doesn't know you can ask them who you should ask next”. This also applies to sales, you say, “Oh, could you refer me to the right person to talk to?” But if you're willing to go to the seventh source, you'll always get your answer. So that was the first one we kind of chatted about.

JH - 00:02:48: Yeah, I think we both liked this one just because you hear about the 5 Whys all the time in user research, and this was just like a nice twist on it. It's not just asking why, it's also finding the source and keep finding the next source and, kind of, really get to the person who's going to be an expert on it or the original material that will give you some new insights. So I thought that was a cool way to kick off the conversation.

Erin - 00:03:08: Yeah. So that's the main thing you missed and we're going to our editors here, we always say we'll fix it in post, but this episode truly was a “fix it in post”. So we're going to transition into the bulk of the episode where Kevin is back, and it should be a good one. A little departure from the usual scheduled programming, but a fun one that we hope you enjoy.

JH - 00:03:29: Yeah, really cool guy to have on as a guest and I’ve been a big fan of his for a long time, so I hope you enjoy the conversation as much as we did.

Erin - 00:03:35: We're back here with Kevin Kelly, so excited to have you here. JH, you were just saying something about failing. Can you start where you left off?

JH - 00:03:45: Yeah. So I've seen this one, I think, in a newsletter or Twitter somewhere from you, but, “if it fails where you thought it would fail, that is not a failure,” and I was curious just how you think about this one, because something we do on the product side often, when we experiment, we try to think of the risks and assumptions and how it might win, how it might lose, and you are trying to predict maybe how it doesn't work in your favor. Just curious, why is that not a failure in your eyes? What does this one mean if you can unpack it a little?

Kevin - 00:04:09: It's sort of like there's two kinds of problems in the world in general, Tractable and Intractable. So the tractable are problems that we know that we have, and we actually, kind of, know what the solutions are, and then there are problems that we know we have, but we don't even know how they're solved. So tractable problems are a class 1 kind of problem. I think failures are, kind of, the same way. If there's a known failure mode, then that's a different class than the unknown failure mode because, in theory, you might have some idea how you can fix the known failure mode. I just had an unknown failure mode, but the other one, the failure mode where the sound doesn't work, okay, that's, kind of, known. That's not a failure. That's like an interruption or whatever, and so we'll have to work around that. So the real place to put your energies is into the unknown failures, the kinds of failures where they're unexpected, they're new, they're different, you don't know how to solve them.

Erin - 00:05:14: Yeah, and for that do you recommend, sort of, trying to anticipate those ahead of time or, rather, learn from them as they inevitably happen?

Kevin - 00:05:24: Well, there's different ways of anticipating. I don't know if you can predict them, but you can have a backup, you can have your plan B, you can have redundancies, you can have your troubleshooting system in place. So there are ways to, kind of, work with that, but I think they're inherently unpredictable. But you can still be, I would say, prepared for them.

Erin - 00:05:49: You had another one here that, to me, is almost the essence of user research in a way, which is, “You can reduce the annoyance of someone's stupid belief by increasing your understanding of why they believe it”. I love this. I think this has served me pretty well when I can remember it in life.

Kevin - 00:06:07: Right. And it's very allied with another one, which is that you can't reason someone out of an opinion that they didn't reason themselves into.

Erin - 00:06:18: Sure.

Kevin - 00:06:19: What that means is that people have opinions for emotional reasons, things that they inherit, cultural reasons, all kinds of stuff, and you want to operate at that level. Operating at that level, even just having a discussion, is far more likely to change their mind than operating at the intellectual logical level because that's not where it was formed. Empathy and things like that are actually as effective in changing people's minds as logic. Maybe more so.

Erin - 00:06:46: Yeah, 100%. And you see this in product teams a lot, “but this is so easy to use,” right. That open-mindedness of why might it not be? What might they believe about how this is supposed to work? It's not right or wrong, but it's just useful to have that frame.

Kevin - 00:07:05: Yeah, and with new things in particular, new things have some points against them. There's some strikes against them from the beginning, but often what we need to do is, kind of, forget. There's a certain amount of forgetting that we need to do to learn something new. We have to, kind of, forget how the old way works, forget our assumptions. And that's not easy to forget because we see something and we immediately associate it with all the things that we know, and we project onto it all kinds of assumptions which may or may not be true. Sometimes they are, but sometimes they aren't, and it's like we're having to educate ourselves that this is something different that may work differently, that may have different assumptions. So there's a benefit in couching things that are familiar to us, similar to what we know. But there's also a danger in that, in that sense, you're also going to get all the other things that we assume about it, and I think a little bit happening with AI right now of unlearning things that we know of other technologies and trying to forget them in some ways to then approach it on its own terms.

JH - 00:08:07: Yeah, that's actually a good segue to another one I had flagged in here about the need to question your beliefs harshly because you probably don't believe what you think you believed. I'm curious, how do you do that for yourself? I agree with this on the surface, but it seems like a hard thing to actually do.

Kevin - 00:08:21: It is and part of it is-, this goes back to, kind of, the very first piece of advice in the book, which I probably just read because it's easier to remember, that's why I wrote them, which is how to learn from those who you disagree with or even offend you. It's because I try to listen to other people whose opinions I don't agree with, always reminding myself that I may be wrong about something. I don't do it on a daily basis, but every now and then I'll come back and, you know, I'll try to hear what that other side is and keep up with it, because I am, for certain, wrong about a lot of things, and I like to not be wrong, and I'm testing myself by looking into those things I disagree with on, kind of, a basis, like looking at publications that I think have an incorrect view of the world. But nonetheless, I'm sure there's parts of it that are true and I want to hear what that is and so that one thing of looking outside my bubble, looking at things I disagree with, that's one way. The second way is to try to explain my beliefs, and this is where it gets hard because I find whenever I try to write something I immediately encounter my own ignorance, and I write in order to figure out what I think. There are lots of things I think I know and believe, but if I have to write them down to really explain them, then I realize I actually don't know about this and maybe I don't believe it. The thing when I'm writing, there’s a question I ask all the time, and I think this is another bit of advice to be interesting, just be really honest in your story, I ask myself when I'm writing something, do I really believe this sentence or is it just because it sounds good or sounds like something that I've heard? Is this really my sentence? And that kind of questioning things, even at the sentence level, I find also useful when, again, trying to not believe everything I think I believe, so the second one of, kind of, explaining it to people is where that shows up.

JH - 00:10:39: To play it back, it's like you can take an external stimulus and bring it in and question your beliefs that way or you can take an internal thought and try to externalize it and you'll, kind of, question yourself that way as well. There's a couple different ways you can do it.

Erin - 00:10:52: Having kids is really good for this, by the way, because they ask you why about absolutely everything.

Kevin - 00:10:56: That's right, yeah. That reminds me of another piece of advice from the book, which is, when your kids are asking you this endless, perpetual series of why, you can turn it off by asking them, “I don't know, what do you think?”

Erin - 00:11:12: Yeah, 100%, and their answer will be more interesting than the one you would have given too.

JH - 00:11:18: My kid the other day was asking me about where wind comes from, and I was like, I actually don't know where wind comes from, I should probably figure that out, that’s an issue.

Erin - 00:11:24: Yeah, it's like, do we believe in God? I don't know what is going on with this wind situation? Can of worms. So on that note, you said, kind of, checking each of your sentences, do I really believe this? I know it's hard to pick your favorites, but do you have one from the book that is the one you most believe in?

Kevin - 00:11:44: So let me think about, like, other, kind of, research-oriented ones. I don't know if this is pertinent, but this is true, “when someone tells you that something is wrong, they're usually right, but when they tell you how to fix it, they're usually wrong”.

JH - 00:11:59: Yes.

Erin - 00:12:00: That's super germane.

JH - 00:12:02: Yeah. I feel like there's a lot of versions of that that you hear in the product world, for sure.

Kevin - 00:12:07: What's the version of that that you might hear?

JH - 00:12:09: That users and your customers are very good at explaining their pain points and the problems they're facing. They're very bad at usually telling you what solutions that you should build. So if you're asking them what features they'd like to see in your product, you're probably going to get misdirected. If you're trying to actually understand what they need help with, then you can, kind of, come up with a good way to solve it.

Kevin - 00:12:26: Yeah, and that's because it's much easier to understand and see how things get broken and don't work than it is to imagine what the solution is, how things work. So this is something I learned from many scenario workshops and things that we did. When brainstorming or improvising or jamming with others, you'll go much further and deeper if you build upon each contribution with a playful “yes and” instead of the deflating “no but”. That's really important when you're in the creative mode of trying to start something you want to do, “yes and yes and yes and”, you want to separate that other judgmental and necessary phase of evaluation of “no, it doesn't”. The crucial editing. So I talk about separating that process of the creative genesis from the editorial judgmental, and you have to keep the editor away from the genesis of the creation itself. You need to protect that. That's part of what happens in brainstorming, you want to protect that genesis, the generosity, the non-judgmental portion of it, and then you need the judgmental later on. But that's the second phase.

JH - 00:13:43: Yeah. I think you have one in there that's specifically about that right? About separating the process of creating from improving. You need to be able to just get stuff out at some point before you edit.

Kevin - 00:13:51: Yeah. Then there's also something about prototyping your life instead of having grand plans. That's something that I came to very late in life and a long time before I could, kind of, absorb the necessity of prototyping things, and now it's a habit. So for this book, I made a prototype book that actually had drawings in it originally, just to see about the format, to see if it worked, to help sell it, to make sure that it was working, check out the design. All the books I do, I make prototype versions of them as I go along. And that's true for things that I build. When we do kitchen remodels, I make a full-scale cardboard prototype of calipers and everything. We just learn so much by doing prototypes, and prototypes can exist to the point of, like, a rough draft of a story or a book where you actually are going to make something complete and then throw it away. You're going to, as they say in the building world, make one to throw away. That's not a sign of amateurism. That's actually a sign of professionalism. That's how professionals do it. The professionals write something knowing that whatever they complete is not going to be used, it's going to be exceeded and superseded by the next version. This was just a draft. And when I was beginning, the idea of, kind of, making something all the way and finishing it was like, that was enough. The idea of redoing it again, that was a kind of failure to me. But now I see, no, this is the essential process of what you want to do.

Erin - 00:15:30: So many of our customers deal in digital prototypes, it's refreshing to hear about your real life paper, you can touch them, prototypes. When you showed the first book, did you actually get people to interact with it and get their feedback or what did you do with it?

Kevin - 00:15:46: There's a few of them and they're now collector items. But, yeah, I sent it around for some feedback. I did a big book of Asian photographs, 50 Years of Photography in Asia. It's a huge book, and I made a prototype of that book, and I learned that it was just too big. It was physically too big to sit on your lap. I did an earlier version or smaller version, and then it went bigger, another prototype, and the consequence of that was I divided the book into three volumes just to be able to hold it. That's what I learned from doing that because otherwise it would have been, kind of, like a disaster if it had been one volume.

JH - 00:16:27: Yeah, and in life too, you can prototype experiences as well. Right. If you're obsessed with a tiny house or something, you can just go live in one for a few weeks and see if you like it and decide from there, right?

Kevin - 00:16:37: Yeah, exactly. Rent something, that's a thing, and also the advice for people starting a business is, well, don't quit your day job. You can prototype it, do it on the side hustle, try it for some set period of time, even if it's full time, I'm going to try this for six months or five months, whatever. See if it works. So rather than commit to it as a lifelong thing, you can, again, prototype experiences, prototype businesses, prototype all kinds of things. And that kind of iterative approach I think is really valuable for whatever it is that you're doing.

JH - 00:17:12: I know you talked about which of these are germane to user research. When I was reading it and prepping for this, I think we probably highlighted, like, half the book, so I would encourage people to check it out. I know there's a couple in here that Erin, you had flagged as more, like, general career advice type things that I think you probably resonated with quite a bit. So I don't know if you want to jump on a few of those just to hit some other areas.

Erin - 00:17:30: Yeah, there's so many good ones. Here's one that jumped out, let's see. “If you desperately need a job, you're just another problem for a boss. If you can solve many of the problems the boss has right now, you're hired. To be hired, think like your boss”.

Kevin - 00:17:43: Exactly. Yeah, that kind of flipping and thinking like your boss is just a really useful perspective if you're working for a company, to pretend you're an owner and anticipate problems that need to be solved. Star employees are people who are figuring out what's going to be the next problem rather than waiting to be told. So I think, even in hiring, this is really hard for people looking for a job, to understand that so many employers are just desperate for really great employees. They're really looking for them, and if you can come to them and basically say, look, I can solve your problems, I know what your problems are and I can solve your problems, you're hired. Okay?

Erin - 00:18:29: You can just ask too. I love when people ask us in interviews, like, what can I take off your plate? What's stressing you out? It's like, oh my gosh, yes, let’s talk about it.

Kevin - 00:18:37: If you can solve your problems, you're hired. And so you have to kind of think like, well, what are the problems that they may have that I might be able to solve. And that flip is, I think, really essential in terms of working in the corporate world. I don't know if you're going to mention this one, but one of my favorite pieces of advice to 20-year olds, there's two bits. One is if you are able to, if you have enough resources, if you are privileged enough, basically, to take a chunk of time, like a year or more maybe, and do things that look nothing like success. They're crazy, they'll be odd, off-kilter, unproductive, unprofitable, a waste of time, kinky, weird, unbelievable, stupid, dangerous.

Erin – 00:19:32: No obvious why.

Kevin – 00:19:34: Nothing that looks like success. And that experience will become the touchstone for most of your life and even success later on.

Erin - 00:19:43: Not the opposite of prototyping, but it's, sort of, just collecting lots of inputs, right?

Kevin - 00:19:49: You could be doing things. You could be doing a project. I think what it helps you do is what we want people-, those that are more successful have done this, it’s, kind of, making your own definition of success. So you want to define success in your own way. This helps you because when you're young, you're most likely to define your success by other people around you. You're basically going to be extras in their movies, instead of being the main character in your own movie, and so, this gives you a chance to, kind of, duck out of that definition of success, and it will generally help your success, because it's going to be more you. It's going to allow you to not just be the best, but be the only one to, kind of, pursue something that's different from everybody else. Because to, kind of, do this improbable thing, you have to become more improbable yourself, and so that tends to favor a different unique path. Normally, when we think of success, you're thinking of what people have already succeeded at and you're tending to follow that, and that's already occupied by those people. Somebody's already sitting in that slot. You want to go where there aren't any slots, and that's the second piece of advice that's related to that, which is at all possible, work on something that doesn't have a name for what it is that you do.

JH – 00:21:13: All right, a quick, awkward interruption here. It’s fun to talk about user research, but you know what’s really fun is doing user research, and we want to help you with that.

Erin – 00:21:22: We want to help you so much that we have created a special place, it’s called userinterviews.com/awkward, for you to get your first three participants free.

JH – 00:21:33: We all know we should be talking to users more, so we went ahead and removed as many barriers as possible. It’s going to be easy, it’s going to be quick, you’re going to love it. So get over there and check it out.

Erin – 00:21:42: And then when you’re done with that, go on over to your favorite podcasting app and leave us a review, please.

Erin - 00:21:50: Someone gave me the advice when I was younger that the worst thing you can do is race to the top of the wrong ladder, right? So open your world to other ladders before you start racing to the top of one.

Kevin - 00:22:00: Right, yeah. So if you're working on something that no one has names for what it is, or language, then you're more likely, one, to be at the place where the breakthroughs are happening, two, you're going to be somewhere where there isn't much competition, and three, you're more likely to be able to land somewhere that's more distinctly you, your own ladder. If maybe ten years ago or 15 years ago, somebody might say, well, I'm doing something that's kind of like radio or it's like a documentary and audio, but it's kind of like doing interviews on TV, it's podcasting. So it would take a long time to explain to your mother what it is that you're doing, and that's a good sign.

JH - 00:22:43: I like that as a rule of thumb. If you can't explain it to your parents, you're probably on the right track. One, you had in here that I really liked was half the skill of being educated is learning what you can ignore, and I think for researchers in general, a lot of what they do is go out and generate a ton of data and a lot of noise, you're doing these long interviews, you have all these transcripts and stuff. Are there any skills or tricks for how you actually do that?

Kevin - 00:23:05: Oh, my gosh, that's a great question. Let me think about that. Because when I write articles, I generate huge amounts of what they used to call tape, huge amounts of transcripts from interviews. And I would say 98% of the time, I don't use anything from it. I'm looking for just these one or two little unexpected phrases. No, I guess the only thing I would say is that you should absolutely feel free or maybe even compelled to disregard most of it, to not even try and process it. But how do you filter out that noise? Well, maybe the one thing I have learned over time is trying to direct the conversations and things. It's kind of like forcing more signals, trying to cut it off at the source.

JH - 00:24:02: As you're gathering.

Kevin - 00:24:03: As I'm gathering. So to not gather it to begin with and to interrupt or steer the conversation. Part of the point of asking questions that they haven't been asked before is that you can get more honest answers and things like that. So that would be one trick. But if you have a bunch of it, yeah, I don't know, other than to say, maybe you should expect that you're going to throw away 98% of it without even touching it.

JH - 00:24:29: Yeah, I think that's freeing, right? Like letting people know that it's okay to discard stuff as you're going back through it.

Erin - 00:24:35: That reminds me of a sort of similar one, which is, “shorten your to-do list by asking yourself, what is the worst that will happen if this does not get done? Eliminate all but the disasters” which is another really freeing concept, like, what really matters here and what is just on a list I've decided that I arbitrarily need to do all of these things.

Kevin - 00:24:56: Well, this actually maybe goes back a little bit to the data thing, which is like, what is the essential data? How much data can I throw away and not have it affect things? Or it's like having a graph, what's the minimum number of points I could put on the graph? Not the maximum. What's the minimum amount of information that can convey it? It's not like I'm trying to say everything I know, put it all into it. It's like what's the littlest amount that I can communicate to get the idea across? And that is another kind of minimalist approach, which is to say, that was the genius of Twitter in the beginning, 120-140 characters, you can say an awful lot in that. That goes to Jeff Bezos in these six-page PowerPoints. So I think you could do things like that kind of editorial constriction of, “You have three slides, no more than three slides”. I'm making something up, but whatever it is, and you have to fit it in, and so you are trying to force some of that triage.

JH - 00:26:07: It reminds me of that Drucker quote of, “There's nothing so useless as doing efficiently that which should not be done at all”. That sort of thing. It's like productivity for the sake of productivity is not always a great thing.

Kevin - 00:26:18: In fact, I don't know if it's in the edition you have, because we did do some changes to it, but there's this idea that rather than try and focus your day to minimize the amount of time you spend on different tasks, you want to change it so you can pick tasks that you want to spend as much time on as possible, which is what I'm trying to do. I don't necessarily want to care about minimizing time on tasks. I want to have tasks where I just want to keep going forever.

JH - 00:26:49: Can I do a random fun, personal one real quick? Because this is one I'm concerned about, there's one in here, “avoid wearing a hat that has more character than you do”? I have a tendency to acquire weird hats when I travel, and I'm worried that I might be guilty of this one.

Erin - 00:27:03 We'll put that in the show notes.

JH - 00:27:05: Yes. How do I know if a hat has more character than I do?

Kevin - 00:27:08: I think people might tell you.

JH - 00:27:10: It's one of those that if you have to ask, you're probably already in danger of it, I suppose.

Kevin - 00:27:14: Yeah, if the conversation is about your hat, then okay, it’s probably that.

JH - 00:27:19: I'll be on the lookout for this one.

Erin - 00:27:20: I was going to go in a totally different direction to JH which is, I love this one, you talk a lot about, sort of, minimalism and essentialism and really focusing on this, which is what matters. “Experiences are fun, and having influence is rewarding, but only mattering makes us happy. Do stuff that matters.”

Kevin - 00:27:37: Yeah, and that's, again, a high bar. That's a very high bar to do that, and people have different definitions of what matters, which is fine and good, but you really, kind of, want to focus on making that difference, and that's actually, after all, why we're here in our bodies, rather than in a VR intangible world, because bodies have impact, they have consequences. The physical is real, and it bites back, and it hurts us. So this brief ride we have in our flesh is because this has the ultimate impact in mattering, it can matter what we do and matters what we do. So that's, I think, our focus, if we can get there. And it's just not a matter of experiences are better than acquisitions, than possessions. I guess it's, kind of, like a hierarchy. I've never thought about that. Maybe that's a little chart. Okay, so there's, like, possessions at the bottom, and then there's experiences, and then there's maybe influence, and then there's the top. It’s this, sort of, Maslow’s Hierarchy of Mattering and Purpose.

Erin - 00:28:44: Self-actualization.

Kevin - 00:28:46: Yeah, but it's purpose. It's mattering and purpose. And if you have an idea of what your purpose is, then that is incredibly powerful.

Erin - 00:28:55: I like to think, I don't think “it's the journey, not the destination” made it into the book, but that idea of that is sort of why we're here, is to figure that out on an ongoing basis.

Kevin - 00:29:07: There is a paradox. There is a paradox in that our purpose is not a destination, it's more of a direction, as you say, it's a journey. It's never done. I know people who are incredibly famous, incredibly accomplished, and great billionaires and beyond, and they're still figuring it out. A billion dollars does not answer the question of what you should do next and how you should become and what your journey is. A lot of them are asking the same question of what am I going to do when I grow up? And actually having a billion dollars at that point, or many billions, is incredibly distracting, warping, a burden. It, kind of, saddles them with another job. I mean, it's imprisoning. It's quite the opposite of what we think. It's like fame. That's one bit of advice, you really don't want to be famous and have a billion dollars and so my advice to everybody listening is try as you will, do not earn a billion dollars.

Erin - 00:30:14: Work on it.

Kevin - 00:30:15: Work on not earning a billion dollars. A couple of hundred million, whatever it is, okay, that's fine. But you don't want a billion because it is really bad for your kids, if you can avoid it, don't earn a billion dollars.

JH – 00:30:30: I’m crushing that one right now.

Erin - 00:30:32: Doing so well. Did you want to finish with one of these Luke questions JH or where should we wrap things up?

JH - 00:30:40: Yeah, somebody on my team mentioned we were talking to you. He was a big fan of yours and threw a couple of questions over. So yeah, let me grab one here. At his previous job, The Inevitable was a required reading for all their new hires.

Kevin - 00:30:50: Wow.

JH - 00:30:51: And he was just curious if you would update any of the 12 forces in the book based on things over the last few years?

Kevin - 00:30:56: Really great question. I mean, I'm embarrassed to say, but probably not. I like having my mind change and changing my mind, but I think there was nothing there that I thought needed to shift. There were things that I didn't get to talk about, but that's not really that important. Those Durans, the principles, those kinds of forces, I think are still working. No, I'm pretty happy and I'm glad that it's still being printed and people are reading it. So in this case, no, I haven't changed my mind about anything.

Erin - 00:31:32: What's your next project?

Kevin - 00:31:34: So I'm working on a 100-Year Desirable Future. I'm an optimist. I'm temperamentally optimistic, trusting. And by the way, that's a piece of advice, is that you should assume and trust that people are their best themselves, and if you occasionally get cheated because of that, that's a small tax to pay for the huge benefit that you have of people treating you the best they can because you treat them their best. In my nature, I'm optimistic like that. But actually, you can teach and learn optimism, and I am teaching myself to be even more optimistic as I get older. Part of that is I truly believe in my version of protopia, which is not utopia, it's an incremental improvement that has lots of new problems, but it's a tiny, tiny bit better than it was last year. So tiny we can only see it in retrospect accumulating over years. But that vision of the future, it would help us to make a future that we wanted if we could see it and believe that it was possible, and I'm trying to describe a possible future that's full of high tech AI, VR, genetic engineering, monitoring all this stuff, and it's the world that I want to live in because most of those worlds that are described in the future are from Hollywood, and they're dystopias we don't want to live in. I think that's not really helpful. I mean, it's fine, it's good stories, great stories, but it's not going to help us make a good version. So I'm trying to work on a 100-Year Desirable Future that would have ten-year increments on the way there, that might be a world to conjure with, to play with. It's not really a prediction. I don't necessarily think that we are going to go that way, but it's more like what they call Normative. It's something that we could aim for.

JH - 00:33:36: I feel like this is one of those books that having in the physical form would be really cool. They'll flip through and see it. I'm usually a big Kindle fan because I like to highlight things and be able to go back to them and stuff. But like, the Austin Kleon books are kind of like that, where I like to flip through them and have the drawings and stuff, and this feels like it's kind of cut from that mold.

Kevin - 00:33:50: Yeah, it is like that. In fact, the prototype that I made actually had little doodles that I made for them that the Viking publishers didn't like. They said they were too homespun.

Erin - 00:34:02: I was going to say, the doodles sound nice to me.

JH-00:34:06: The collector’s edition is out there.

Kevin - 00:34:08: That's the whole point of it, they were homespun, they're little doodles. But they wanted to say, well, maybe we can have a professional artist. It's like, you don't get it. Come on. But yeah, so this is a little handy thing that actually I like to look at too. Again, I wrote them to remind myself of my own behaviors. For example, one of the first ones that I jotted down was, if you get invited to go talk somewhere, go visit somebody, go out for a walk, that's six months from now or more, ask yourself, would I do this if it was tomorrow morning? Because it will be tomorrow morning soon enough, and you'll have to answer the question. So if you say no, then you say no now, and that's one way to control your time. One last thing, the last piece of advice, the second to last, which was, “your goal in life: you should be able to say on the day before you die that you have fully become yourself”, and that's my goal is that I want to unleash the genius of everybody born and yet born by increasing the amount of technology and choices and opportunities in the world, so that, in addition to the existing technologies like clean water and education, et cetera, that everybody would be able to say on the day before the die, I've truly become myself, and that would be my goal. That's what matters to me.

Erin - 00:35:39: What do you think most holds people back from doing that? You seem to have a real abundance mindset that we're capable of so much, right?

Kevin - 00:35:51: I think it’s a lack of imagination. Actually more. I think that's the antidote to fear, it's not bravery, but imagination. To be able to imagine it differently, to be able to imagine that it's possible for things to work, to imagine how a good thing might happen. Because it's so easy to imagine all the problems and imagine all the ways that things break. If you can only imagine things breaking, of course, you're going to be afraid and worried and upset. But you have to exercise some imagination to believe in how it could work. The unintended benefits, not just unintended disasters. I think if we can encourage the imagination of people to imagine good, complicated things that may take more than our own lifetime to accomplish, and so the one thing that helps is maybe that, to answer your question. Another thing that helps is to change the horizon because we underestimate what can be accomplished over a decade, and some of these things require that kind of time. So bad things happen fast, good things always happen slow. We have to extend our imagination to a longer-term, kind of, raise our horizon a little bit. When you do that, then the inevitable current problems are more easily seen to be overcome because we have a longer track, and so the ups and downs, the volatility, the pluses and minuses that are just a natural part, they can be overwhelmed by the gains in the long-term. That's true investing. It means, like, if you're on a regular basis investing a small amount, the ups and downs of the market don't really concern you, you're just concerned about that long-term compounded interest rate.

Erin - 00:37:47: That's why I haven't looked in a year.

JH - 00:37:50: Yeah, I think people who check it all the time tend to do worse than the people who just leave it. Yeah, if you zoom in on the graph, everything looks spiky, if you zoom out, everything, kind of, looks a little smoother and upright.

Kevin - 00:37:59 That's something that I think can help people cultivate that kind of optimism for the future is to take a longer view.

Erin - 00:38:07: Yeah, love that. Courage to imagine things working out.

Kevin - 00:38:11: Right.

JH - 00:38:12: Yeah, a lot of the bad stuff you imagine never happens anyway, so it’s a lot of worry for nothing.

Erin - 00:38:15: Some other thing happens that you weren't worried about. A real failure. Well, this has been so much fun. Thank you so much for joining us, really appreciate it, and I think we're airing right around when the book comes out.

Kevin - 00:38:27: Great, thank you. Thank you for the great questions. I love hearing about a little different perspective, your own work, a bit about it that now I can appreciate it a little bit more.

JH- 00:38:37: Yes, it’s a pleasure. Thank you.

Erin – 00:38:39: Hey there, it’s me, Erin.

JH – 00:38:40: And me, JH.

Erin – 00:38:42: We are the hosts of Awkward Silences and today we would love to hear from you, our listeners.

JH – 00:38:46: So we’re running a quick survey to find out what you like about the show, which episodes you like best, which subjects you’d like to hear more about, which stuff you’re sick of, and more just about you, the fans that have kept us on the air for the past four years.

Erin - 00:38:57: Filling out the survey is just going to take you a couple of minutes and despite what we say about surveys almost always sucking, this one's going to be fantastic. So userinterviews.com/awkwardsurvey and thanks so much for doing that.

JH - 00:39:10: Thanks for listening.

Erin - 00:39:12: Thanks for listening to Awkward Silences, brought to you by User Interviews.

JH - 00:39:17: Theme music by Fragile Gang.

Creators and Guests

Erin May
Host
Erin May
Senior VP of Marketing & Growth at User Interviews
John-Henry Forster
Host
John-Henry Forster
Former SVP of Product at User Interviews and long-time co-host (now at Skedda)
Kevin Kelly
Guest
Kevin Kelly
Kevin Kelly is an accomplished author, speaker, and “evergreen optimist,” known for his work on technology, innovation, and the future. As the founding executive editor of Wired, Kevin has been instrumental in shaping discussions around technology and its implications on society. He has authored several influential books, including "The Inevitable," which delves into the technological forces that will impact our future. Currently, Kevin is working on a project envisioning a desirable 100-year future.