Dig Deeper
host: Digby Scott
New Zealand vs Australia, ignoring the news, talking with friends, journaling, and the cone inside the cube.
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Transcript:
Digby Scott
My guest today is Derek Sivers. There are some people whom you can define easily, but Derek's not one of them. He's a true explorer who's journeyed from musician and circus performer, to the founder of the groundbreaking CD Baby, to TED speaker, to dad and thinker and author, and I reckon fascinating conversationalist. and he's a self-described slow thinker. I love that, and I want to explore that a bit more. And he's known for his love of different points of view. And I reckon this truly shines through in how he chooses to live his life. And like me, he's an immigrant living in New Zealand right now, and I am so excited to explore, perhaps even starting there, Derek. Welcome to the show.
Derek Sivers
Thank you.
Digby Scott
We both have chosen to make New Zealand our home. Me from Australia. You from, well, actually, where was it from before you came here?
Derek Sivers
I'd say a combination of California and New York.
Digby Scott
You wrote a little bit about it on your your website, about why you came here. So people can go and read that. But tell us a little bit about having come here, perhaps what were you hoping for New Zealand to do for you and how has that played out.
Derek Sivers
Ooh. I think of different places having different purposes. You don't move to Dubai to enjoy nature and you don't move to Tasmania to be a party animal.
Derek Sivers
So moving to New Zealand to me was right when my kid was born. I just wanted to be somewhere away from all people where I knew nobody so that I could give my kid my full attention for age zero to six. I just wanted to be a full time dad, give him all my free time without any distractions, no social meetups. I just wanted to be with him all the time when I wasn't working. Or just be working when I'm not with him. And ideally in nature. I really wanted my kid to have a connection to the real physical world, not just screens. I wanted him to deeply know the experience of having his feet in a river and hands in the mud and growing up climbing trees and feeling the long grass blowing in the wind and all those things that to me are the quintessential physical world experience that I wanted him to know. So that was a big idea. I was only planning on living here for six or seven years to raise him from age zero to seven and then as a nice side effect, get citizenship because I really liked how New Zealand will make you a citizen if you're a resident here for six years. So that was it.
Digby Scott
And from what I read, that sounds like that's all played out. Your intent for your kid is really, you know, that's paid off.
Derek Sivers
Mostly OK. I'm being completely honest here. This is going to be really nerdy. When he was born, I thought what would be the ideal upbringing for a kid would be the first six or seven years of their life in just nature paradise. And then as their brain is developing further, you go somewhere with more cultural inputs, say somewhere in Europe, you could live somewhere in the middle of Europe where they would hear a lot of different languages, get to know a lot of different human ways of living, the Mediterranean lifestyle, the Nordic lifestyle, seeing how there are other ways to live. And then when he's a teenager, I thought it would be great to live in a place where it's culturally cool to be studious and smart. Instead of most of the world where it's culturally not cool to be studious and smart. So places like Singapore, Taiwan, culturally cool to be studious and smart. That's where I wanted him to be a teenager. But alas, it was not only up to me. He also has a mother. His mother got a job in the government here in Wellington, New Zealand, and that was that.
Digby Scott
You know what? I think Wellington is a place to be studious and smart, actually, because it's a government and disproportionately there's a lot of smart people here. We were just talking about Perth before we came on, and that's where I'm from originally. One of the things I noticed that's different about here is that it's not really about how big your house is or what car you own or any of that sort of stuff. It's more there's an intellectual conversation that happens here more regularly. So maybe it's not "are you studying?" but I think there's an interest in world affairs and things that I find probably dialed up more than I'd find in a lot of other places.
Derek Sivers
I wonder if that's just in our age range, though. I get the feeling like the teenager culture here, unless I'm wrong, I might be wrong, but I get the feeling that it's not cool to be smart as a teenager in New Zealand anywhere.
Digby Scott
All my three kids are down in Dunedin at Otago and University. Yeah, I think that's very true down there. It's like, yeah, do your study, but that's not what we're really here for. I'm curious about coming back to the New Zealand experience, though.
Digby Scott
So you talked a lot about your experience as a dad and raising him. How do you think it's shaped you? Because you've lived here twice now, right? How is it?
Derek Sivers
Well, I've really been here for almost the entire 13 years since I moved here in 2012, except we went to England for what turned out to just be a year and four months. I thought it was going to move there for 12 years, but then COVID hit and sent us back. So I've really been here for 13 years in Wellington, except for that one year away.
Derek Sivers
So how has New Zealand shaped me? The best thing is the connection to the real physical world that I spend most of my time when I'm not just writing. I spend out in the forest, on the coast, in fields and rivers and just out with the real physical world.
Derek Sivers
And that is so good for the soul when everybody else is freaking out about something they've seen on the news or "the state of the world" and they're in an absolute panic and and full of anxiety and saying, "How can you rest with what's going on in the world today?" And I'll look around and say, "Have you been looking at screens? Hold on a second. Just turn off the screen. Like, seriously, just power down the phone, hold down those two buttons, power down. Okay, now step outside for a second. Let me take you on a walk. Look around. Do you see panic in the streets? Do you see everyone freaking out? Do you see a horrible world about to implode? No, that was just in your screen. If you just turn off your screen, the world's not so bad."
Derek Sivers
I mean, depends where you are. If you're in Kiev or Novi Sad Serbia right now, then yeah, there's crap going on. But most parts of the world are doing okay. It's just the screens that make people panic, mostly through the businesses that have a financial incentive to make you panic, and they will do everything in their power to make you freak out because it makes them more money. And then the appeal of outrage, people who just want to go be outraged, see outrage, feel outrage. There's kind of some dopamine around that. So being here in New Zealand is to be quite far from all of that. Not quite Fiji far, but almost.
Digby Scott
Yeah, you know, it's getting me thinking a couple of things. One is, there's this metaphor I often use about red wine versus champagne. And you know, champagne's got the fizz and it's exciting and, you know, it represents energy. Whereas red wine represents more of a stillness and a groundedness, right? I think it's a bit more red wine here, right? And getting into nature easily is a bit of a red wine vibe, which slows, I don't know if it slows the heart rate, but there's something about learning to just get your red wine moments, you know, as opposed to if you jump on any social media, any news channel, whatever, it's all champagne, right? It's all the froth and bubble. And idea that you don't need to read the news or watch the news. Just read a couple of good books a year on world affairs and you'll know everything you need to know. And I experimented with that a month or two ago where I just decided not to watch any news and take the apps off my phone, all of that stuff. And then when I jumped on again, you know, a little time later, I was like, "Oh, it's the same stuff. It's the same bubbles, you know? It's just different words, but it's the same stuff, right? And so there's something about perspective that you get.
Derek Sivers
You said that your audience is about our age. So in the US, in the early 90s, O.J. Simpson had this thing where he suddenly his wife was killed and he was running away in a Ford Bronco. And it was big news. And it was in the newspapers every day. Now, this before the internet. But newspapers would carry big giant headlines like "O.J. Won't Eat in Jail." "O.J. Said This." It would be as if it like the size font that we used to reserve for declaring war, you know, World War Two. Now that was like "O.J. Won't Eat." And it was at that time when I was living in New York City, regrettably seeing these giant headlines every day that I did a sabbatical, retreat, whatever you want to call it. I went off to the Oregon coast to a cabin in a town with a population of two, and I brought my musical instruments with me, and I sat there making music for eight months of solitude, by myself, just doing nothing but making music for eight months. No media, no connection to the outside world, no TV. There were really no newspapers in this town of the population of two. I would see friends for a couple hours every few weeks when I'd drive into the city of Portland and then come back. But other than that, for eight months, completely cut off from everything. After eight months, I moved back to New York City. Having been transformed by this experience. I wrote 50 songs, I recorded it, I read 30 books. My life had changed. I go back to New York City and the day I get back, the headline says, "O.J. Says the Glove Won't Fit." And I went and met up with some friends in New York that said, "Oh, wow. I hadn't seen you in a bit. You went away?" And they were just right there living their same lives in New York. And like nothing had changed. Everything was exactly the same. The same media headlines were there. And I thought, God, could you imagine if I would have been here for the last eight months seeing the same daily headlines about O.J. Simpson? Yeah, I guess there's a comparison there to be made about social media.
Digby Scott
There's definitely a, there's a, what are you putting into your diet? Because the, this whole idea of getting away and being in nature, but we can't always do that. And you don't live in a cabin with that in a place with two people anymore. You live in a city for various reasons. I'm thinking about people listening and having that opportunity to go away for eight months and write for a lot of people would feel like a distant dream or maybe a nightmare for some people to do that but how do you how do you think about life design?
Derek Sivers
Well, let's keep it on this subject. You said, well, somebody couldn't do that, or somebody listening would say, well, I can't do that. But you can do your own version. The woman who distributes my books, her name is Saeah Lee Wood, and she lives in Asheville, North Carolina. She distributes my paper books and the books for about 50 other independent authors. She has a company called OtterPine. Otter like the animal, pine like the pine tree. And Saeah is so wonderfully cut off. Here she is online all the time, but just helping her clients all the time, producing these books, doing these layouts, contacting She's in the midst of things. She's made this own business herself. She's kicking ass. If you ask her anything about world events, like, I don't even think she necessarily knew who won the election or whatever, because anything to do with world events, she goes, "Oh, I don't even look at it. I have no idea. I don't look at any media. I have no social media. I go to no websites. I read no news. I have no idea what's going on out there." And it's amazing that she just deliberately just won't go there. She just doesn't care, doesn't want to know, doesn't want that noise in her brain. By the way, she is not some cut off hippie. She was in the US Navy for actually she was a US Navy, like some kind of ranking person, like a captain or something like that in the US Navy for many years. She went to military school. Super smart. In the US Navy for 15 years and then just like her dad died in Alabama. She went back to the US and started this business and then just said like, no, I don't need to know any of that stuff. So you can be in the midst of things, have lots of friends and activity without falling into the hole of negative noise.
Digby Scott
Yeah, and I think it's about the choice, right? Because when you're swimming around in a habitat that the norm is the news, then to make that choice can often feel harder, because it's like breaking away from whatever else is doing, and doing it your way, and the risk of not being informed, and particularly not appearing to be informed.
Derek Sivers
Although I think you should wear that with a badge of pride, because I think everybody over the age of three can see that if you're deliberately choosing to not tune into the pointless noise, that's really kind of cool and wise of you. I think everybody feels the same thing we're feeling. And it's kind of, I'm almost feeling bad that we're nerding out on such an obvious point. That I think anybody, if you say like, "Oh, I don't read the news. I know nothing of what's going on." I think almost everybody around you would say, "Whoa, that's really cool."
Digby Scott
Good for you! Go you! I agree. Yeah. I go up to the northwest of Western Australia every October to get off the grid and I go windsurfing and surfing 150km from the closest town, just with some mates. There's no internet and I love it. And yeah, it's interesting the responses I get about that. It's like, oh wow, I'd love to do that, to something like that. And this is only for two weeks, right? And it is definitely an inspiration for people. And I don't do it for that reason. I do it because I love it. And it is a unhooking from the day to day. It's interesting though, it is such an obvious point, but why don't people do it? That's probably my question. Yeah.
Derek Sivers
It takes a little effort, yeah. Unhooking. Yuval Noah Harari is the Israeli author that wrote the book Sapiens. So many people recommended that book to me when it first came out. Everybody asked me if I had read it over and over again. "Derek, you should read this." And I ignored it until one day I saw an interview with him where he said that every year he goes away for two months of meditation retreat, where he's completely cut off for two months. And he said every day he spends one to three hours in meditation. And that's when I got interested in hearing his thoughts. Because I want to hear the thoughts of somebody who's not caught up in the swirl, who's not in the same crowd as everyone else. It's the voices that are outside of it that you want to hear from, because they're going to have something different to say. They're going to have a different insight. Being cut off from the zeitgeist is a competitive advantage.
Digby Scott
The fresh perspective. Yeah. 100%.
Digby Scott
So the last time I went to this place in the northwest of Western Australia, I go with this group of guys and they're all... I'm the youngest, right, and I'm in my mid-50s. The oldest is 71, there's a 70 year old, then there's a 64 year old, a 63 year old, and I think then I'm the baby. And they all go really hard in the ways and it's inspiring to watch, right? But they also give less fucks about things because they, you know, not just because they're retired, I think it's just an age and stage thing. And where they're just like, "Yeah, we don't really care about what's going on in politics. It doesn't really matter." I think they just have got this sharper focus about what really matters and probably more importantly, what doesn't. And it inspired me. And I wrote about these guys and I shared it in a post and it got so much engagement about this idea of willing to go against the grain, and willing to just go. And I don't think that's why they do it. It's not like, "I give less fucks because I want us to be seen to be giving less fucks." It's because they're making choices that appear to be just different to what most other people are doing or thinking. And I'm really fascinated by, "Is that a natural process?"
Digby Scott
I look at you. Your path, if that's what we call it, isn't a mainstream path for what most people would call a career. I could say, "Derek gives less fucks." I don't think that's what it's about though. What is it about?
Derek Sivers
Led Zeppelin.
Digby Scott
Okay, let's go there. Of course, I thought you would say that.
Derek Sivers
Years ago, I read a little interview with Led Zeppelin, where they said "Our sound was so different at the time we came out, partially because we didn't live in London. We lived in Wales. We were out in the countryside, And listening to Middle Eastern music, trying to do our own thing, mixing microtonal scales with the blues cranked up to 11, and we just weren't in the scene in London, so we weren't influenced by the scene, and so we had a unique sound." And that always stuck with me, that their sound was unique because they were off in Wales.
Derek Sivers
And I think it can be the same for any of us, whether we're programmers or consultants or writers or whatever. You can have a unique perspective if you stay out of the zeitgeist.
Digby Scott
And I love that. That's a lovely thing for anyone to think about. What's my way of being that allows me to just discover me, and discover my voice, and discover my unique angle on the world? You wrote about you can be global or local. And for me, I'm global as well. But for years, it was like, "Oh no, no, I'm local. I'm from Western Australia, and this is how we do things here." And then I went backpacking, and I went, "Oh, there are other ways to do things." And now I'm at a point where it's like multiple ways of doing things. I don't know exactly what my way is, but I'm going to keep experimenting. And that's cool. As opposed to, "Oh, I'm deviating from my norm." And then eventually I'll come back, because that's what I do. I've just got back from Western Australia. You asked me, what's it like over in Perth? It's funny, isn't it? Because it's when you come back into a place that you used to hang out in and you see these shaping forces, I'm like, "Oh yeah, there's this way of being that's expected around this in this world." And to break that orbit is really healthy. And I'm thinking about anyone listening who feels like they're stuck in an orbit, they're stuck in London where they'd rather be in Wales writing music.
Digby Scott
What do you think about ways to break the out of that orbit?
Derek Sivers
Sorry, it's blunt, but I love moving. I love moving every time I have a breakup. I just want to get out of there and go somewhere new, just look forward, not back. I love moving just to shake things up. The world is our home and the place you currently are is like one room in your house. And if somebody spent all of their time in the kitchen and just never even went to the study, you'd say, "Well, why don't you go over there for a bit? Why don't you go out to the deck?" It's a different point of view. You don't always have to stand here in the kitchen. I feel that way with living around the world. Why aren't you living in Africa? It's huge. It's wonderful. There's such a different point of view to be had. Why aren't you living in the Nordics somewhere? Go get to know your home. I really want to keep moving for the rest of my life to constantly shift my point of view, like getting to know the different rooms of my house.
Digby Scott
I love that. You're building a new house right now and you haven't moved in yet, though, right? And for most people, that would be like, I'm building my dream home. And then I reckon the addition to that sentence is, and this is where I'll be for a long, long time. And I'm reading that's not the case for you.
Derek Sivers
No, no, no. We'll see how long I stay there. But I might just keep it as a backup retreat. My kid really loves it. I've got 10 hectares of forest with a creek running through it. My kid is just in love with it. There's a wild boar in that forest that he's tracking and he wants to have that place for the rest of his life. So I'm very likely to put it into his name when he's 18 or something.
Derek Sivers
But okay, so there's another interesting aspect about New Zealand is every now and then a rich friend is surprised that I spend no money on things, cars or items in the home that impress guests. And I have have to explain that here in Wellington, particularly for me, I don't have guests. If I were to get a Lamborghini, nobody would see it because I don't really drive very much. And I think if I had a mansion, nobody would see it because it's just me here. And so there's nobody to impress. I've made a lovely private life for myself here where I just spend all my time my kid and we're out in nature and all of my friends are spread around the world. And I'm really glad that I'm not living somewhere like Dubai or Manhattan, where I might be tempted subconsciously to impress other people. If I was being super social, I might think I should have a nice home to have people over to, or when I do have people over, I should have nice things to present or a nice view out my window so that they can be impressed. But instead, there's just nobody to impress here. With no audience, you don't perform.
Digby Scott
Exactly. That's fascinating, isn't it? The whole driver is what other people think. And you're like, "I don't care about that. That doesn't matter to me."
Derek Sivers
Right. Well, there aren't any people in my life. I know some people have super social lives that are in the same place I'm in, and they try to impress people. But in my life, my physical in-person life, there is no audience. It's wonderful.
Digby Scott
I do love that. It's interesting, right? So where I live, I've got an incredible view out over the water, and it's a stunning spot. And I've been here about three years, coming out of a marriage breakup and having in New Zealand this is great term in Maori, which I interpret to mean your place to stand where you can just right this is me and this is it nourishes me and it's done all of those things right it serves me so well. Yesterday my partner and I found a different place that we're going to rent for well at least a year, and it's miles from here. It doesn't have a view but it has all these other amazing things, and it's in a very different part of Wellington. And I'm in this sort of in-between space of really wanting to do that and create a new chapter, and at the same time loving this place and decided not to sell it, going to rent it out, and rent this other place and see how it all goes. And I'm noticing this tension between the old and the new and this sort of, how do I transition well? And I think this question, how do I transition well, is relevant in so many contexts, not just moving home or physical location. How do you think about that? Because what I observe from a distance Derek, is that it seems to be quite a quick decision and you move, right?
Derek Sivers
There's a movie called Big Fish starring Ewan McGregor where it's a man at the end of his life, like kind of in his deathbed, telling his story of his incredible, fantastical life. And he starts in a little town in the middle of nowhere in Mississippi. And he goes out on his big adventure. He decides, "I'm going to go see the world." And the very first place he stumbles across, he goes through this dark forest and accidentally comes out in paradise. And suddenly at the very beginning of his journey, he's in the most beautiful town ever where everybody's wonderful and everybody's sweet and everybody's happy and dancing and they're all, they love him and he loves them. And it's just, the weather's always perfect and everything's lovely. And everybody's saying, "Come stay! We all love it here! It's the best place in the whole world! Come on, you have to stay!" And he's tempted at first, but after sleeping there a night or two, he said, "I'm sorry, but I've got to go have my adventure." He said, "I'd be the luckiest man on earth if I end up here, but I can't stop now." And I love that. So he goes back out into the world, leaves paradise to have his amazing adventure. And I think at the very end of the movie, he does end up back in that little place.
Derek Sivers
And so that's how I feel whenever I find some place really nice, like you're describing. If I love it so much, I'm like, "Oh my God, I love this place. This is... I just feel great here. I could live here for the rest of my life." Then I think, "I gotta go have my adventure."
Digby Scott
That is awesome. You know, it's funny because you've named what I feel when I go back to Western Australia, which is pretty frequently, a lot of people there will say, "Oh, when are you coming back to live?" And I go, "I don't know if I ever will." When I moved here, which is a little after you actually, about 17 years ago now, I didn't want to come here. My wife's a Kiwi and she was keen to come here and come back and connect with her roots and I love Western Australia. But then I got my head around it, I went, "Yeah." And I remember going to see a counsellor and she just kept my head around moving so I wouldn't feel resentful. And I remember saying to her, "Oh, New Zealand, it's the ends of the earth, it's purgatory and all this stuff." And she's like, "What? How are you thinking that way? What is that about? You're talking like you're going to just be... it's a one-way alley that you'll never be able to reverse out of." And she said, "What about if you thought about a chapter of the book of your life that you get to pick up the pen and you write it, and that's the 'go have your adventure' spirit?" And that changed everything for me. And I'm finding myself channeling that with this house move now. It's like, "Yeah, what's the next adventure? Keep moving forward. It reminds me a bit of the idea of money. Money is something that isn't designed just to sit stagnantly. Money is useful when it's in motion. It's a bit like us, I think. We want to be in motion and we want to be adventuring, if that's our values. But I think there's something that I reckon about, yeah, it's It's the living the adventure, choosing what's next as opposed to holding on to what you have. Does that make sense?
Derek Sivers
Absolutely, yeah.
Digby Scott
Yeah, and I suspect you're the same.
Derek Sivers
My top value is learning and growing, constantly expanding my understanding of the world, expanding my comfort zone, expanding what I consider home. Ideally, what I'm shooting for is I want every corner of the world to feel like home. Every part. I want to feel at home in Saudi Arabia. I want to feel at home in Tanzania. In each of these places I want to have friends, I want to have comfort and a feeling of, "Ah, this is my place. I love it here." And that's what I'm shooting for.
Derek Sivers
In fact, that was the path I was on when I accidentally had a baby and his mother said, "I hate moving. I refuse to move. So we're staying here." And I was furious for a couple years. I felt supremely cheated by the universe, that the one thing I wanted, which was to keep moving always, was thwarted by this darling boy that is my top priority. And so instead, after a couple years, I just decided, all right, I'm taking a short little 18-year hiatus from that plan. Once he's 16, 17, 18, doesn't need me around anymore, I'm back on that plan for the rest of my life. I plan to just keep going until every part of the world feels like home.
Digby Scott
It's so it's a for now not a forever right it's yeah I love that.
Derek Sivers
It changes the perspective. If you think of sitting in a sauna as forever, you'll hate it. If you think of it as for a few minutes, you'll love it. I would not want to live forever treading water in the ocean, but jumping into the ocean for a few minutes and swimming and treading water feels really nice.
Digby Scott
That's awesome. Yeah, like how do you make it for now? This is great and for now won't last forever You know, that's a useful question, right?
Digby Scott
So I introduced you in part as a slow thinker, and I would love you to explain what that means to you and why it matters.
Derek Sivers
It's the context of what we've been talking about already. Your instant reaction is a knee-jerk reaction. It is impulse, it's reaction, it's often the unconscious reaction that you've already had stored in there from earlier. It's leftover stuff from the past. But when you take just a second to think, and it could be five seconds or five minutes, you connect with who you are now instead of just surfacing old stuff. You think of an alternate point of view instead of the first one that came to mind. And it's fun to think instead of just react. So for all these reasons, I find it better to stop and think for a minute instead of having a quick reaction to everything. Which then makes me annoying to try to have a debate with if somebody's on the edge of their seat frothing at the mouth and wanting to attack me and they say "yeah well what about this? Huh? Huh? What about that?" And I go "hmm good point I'll think about that." "Well yeah what do you have to say about that?" "Hmm, nothing. I'll think about it." Sometimes people want to fight, they want to debate, But I'm not there to debate, I'm there for my own sake to think about things. Those interesting thoughts usually come later.
Digby Scott
I love that. And just listening to the way you responded to that question, there was a lot of gaps between the words.
Derek Sivers
Guess what? I've started editing the transcripts of these live interviews. And I've learned that it makes way more sense to collect my thoughts for a few seconds first and then speak, instead of speaking in a bunch of ums and uhs and half-finished sentences and changing course mid-sentence. I've learned to collect my thoughts first to make an easier transcript to edit. Yes. Actually, it's also trying to get past the first answer for the sake of the audience. That if every time somebody asks me a question, like, "Tell me about yourself or how did you get your start? If I impulsively start spewing out the same answer I always give, it ends up being inconsiderate for somebody that might have heard me speak before. It would be more considerate if I think for a second and think of a different angle to answer that same question with.
Digby Scott
Let's just meta that. So I asked you, what does slow thinking mean to you? How do you think about that? So and then you slowed down, you had lots of gaps and you seem to be really considering the answer. What out of your answer was the freshest or maybe the newest? Given that that's the point to slow down and actually just not just have the right answer.
Derek Sivers
The considerate part, the part that ultimately I'm doing this for the entertainment of the audience.
Digby Scott
Let's just sit with that for a minute. It's beautiful.
Digby Scott
I write a lot about this idea I call "unhurried productivity". It's kind of like Cal Newport put that book out, "Slow Productivity", a year or two ago. I've been thinking about it for a while before that came out. And this idea of, well there's two words there, right? Unhurried and productivity. And I think productivity is a loaded term. The idea of the benefits of unhurried because what I see is productivity being equated with being hurried and being busy and being rushed and that's how we produce more because we just cram more into an hour or a day or a year whatever. So when I say unhurried productivity unhurried productivity as an idea. What comes up for you?
Derek Sivers
Probably more effective because you're giving yourself time to ask whether this is worth doing. Whereas if you're just quickly reacting to everything, you're just doing it, let me just clear off my plate, then you're often not stopping to ask if this is worth doing at all. Whereas if you're saying unhurried by definition, you're taking time to think if this is worth doing. That's a huge one. So many people are busy doing things that They shouldn't bother doing it all. They could just say no to all of it.
Digby Scott
I've noticed our conversation has got more spaces in it just in this last five minutes. We're deliberately making a choice to slow down. What thoughts have you got about how you do that? Anyone can do that. Make that choice to be responsive rather than reactive, I suppose. What's the practical there?
Derek Sivers
A key moment happened for me in my life when I was feeling completely overwhelmed with my company and called a friend saying that I have to do this, I have to do that, I have so many things, I'm overwhelmed. And he said, you don't have to do any of that. I said, yes, I do. I have to pay my employees. I have to ship the items that people paid for. And he said, no, you really don't. You're choosing to do it, but you don't have to do it. He said, it's really important that you understand this distinction. You could, right now, just get up and walk away. And I said, "No, I can't. I'm the owner of the company." He said, "It doesn't matter. You can still just walk away. Right now, you can hang up the phone with me, change your phone number, go to Hawaii, go fishing, and never come back." He said, "Eventually, courts would work themselves out. They'd take some money out of your account to pay the people that sued you for it, and it's done. But you don't have to do any of this. You're choosing to do it. You really need to understand this." That hit me in a really profound way 17 years ago. And that's why I sold my company. I realized I was not enjoying it, that I could just walk away.
Derek Sivers
And it came up again last week when I was feeling really overwhelmed with work, even though it's all just self-created stuff. And I was calling a friend to complain about feeling overwhelmed again. And my sweet friend, she's a brilliant author from Romania, said, "No, you don't have to do any of that, Derek. Why are you acting like you have to do this stuff? You could just choose not to." Oh, right. Thank you. I needed that reminder. So I think all of us can remember when you're feeling overwhelmed with whatever it is. Cleaning the kitchen. Doing the tasks you're paid to do. You don't have to do it. You could just say, "I'm not doing this. I'm handing this to somebody else. I'm going to let this go undone and see who complains. Maybe nobody It's a nice reminder that no matter what it is, no matter what your job or your life situation, you don't have to do it.
Digby Scott
There's always a choice. It reminds me of the Viktor Frankl quote from Man's Search for Meaning, that we've always come back to the choice that we have to respond to anything.
Digby Scott
And it's an interesting one that with this house move, right? My partner texted me this morning saying, "So should we move it on this date?" and I'm like, it's like a month away. I'm like, "Oh my god!" and then I did exactly that. I said, "Well, we could choose that or we could choose a different one or maybe we could do an 'and' rather than an 'or'." You know, like we could have to have a whole three weeks to move in sort of thing, right? And as soon as I remembered to respond, not react, and go, "What choices have we actually got. And then I remember that, "Man, it's all invented. We just make all this shit up."
Digby Scott
And I love working with leaders where they're like, "It's all about, we have to do this, and this is the way we do things, and we've done it all this way, all the time." And then I love to go, "So how much of that's immutable versus invented?" And that's a lovely circuit breaker question. So what's unchangeable and will forever be this way and what's invented?
Derek Sivers
My new book called Useful Not True, I think is perhaps too subtle because to me, this point was so profound.
Derek Sivers
What you were saying - that boss saying this is how it has to be - Useful Not True is about pointing out that basically nothing people say is true. If you define true as the only possible answer, if it's not the only possible answer, well then it's not true. It's just one way of looking at it. So when the boss says it has to be this way and it has to be done by then and this is how we're going to do it, think, well, that's not true. Not that it's necessarily false, but it's not the only answer. You have to open up your mind to other possibilities that this is not the only one.
Derek Sivers
That can be applied in every aspect of life. It helps so much even to your own thoughts. Like when you said, "What? Moving to New Zealand, it's the end of the earth. It's purgatory." That's not true. It's only one way of looking at it. Anything you can say, any belief, anything that feels like a social fact to you is just One way of looking at it.
Digby Scott
That's awesome. Have you heard of the cone in the box exercise?
Derek Sivers
Not at all.
Digby Scott
II draw a circle, and I'll ask a group, what's this? Well, this is a circle. And then I draw a triangle. So what's this? A triangle! And then I'll draw a 3D cube on piece of paper, and I'll say this this box you can't open it you don't know what's in it but you want to find out what's in it so I'm going to tell you what's in it there's a cone resting inside the box in in the middle of the box. And then I give you a little pin and you can poke a hole right in the top of the box and you look in and then you see this shape. Which shape would you see? Would you see, if you're looking down on top of the cone, would you see a circle or a triangle? And most people would say, well I see a circle, something circular. And And I said, "What shape would you see then?" He said, "Well, it's something triangular." And then I'll say, "Well, which one's right?"
Digby Scott
And then it's like, "Well, huh, that's the wrong question."
Derek Sivers
Nice.
Digby Scott
And it's a lovely way into a conversation about what you're talking about. It's not true, it's just your view. You know, and I love, so "Useful, Not True" to me, incredibly powerful set of ideas around that.
Digby Scott
And it makes me wonder about where's an example maybe that, and maybe if you can think of one, that you're bumping up against a truth that you might be holding, because I'm imagining this is an ever-learning process, right? It's like, "Ah, that's another thing I thought was true, but maybe it's not. I'm wondering if there's something that you're living or experiencing now around that. Ah, here's one for me to challenge. Actually, I thought it was a triangle, but it's more nuanced than that.
Derek Sivers
Hmm. I don't have any good answers right now. To me, it's constant every day, even little tiny things.
Derek Sivers
There was a certain way I was programming my database functions and I've been doing it that way for 12 years and it's worked really well for me. And for the first time, just a few days ago, I looked at it with fresh eyes and went, "Oh my God, I don't have to do it that way. And this way I've been doing it for 12 years, there's a whole chunk of unused cruft there that I've, it's actually, it was like, I was custom crafting error messages to be returned from my PostgreSQL database functions. And I'd put how many hundreds of hours into making these functions with these custom error messages. And then I went and looked at the rest of my code to see, have I ever once in 12 years used one of those error messages and realized, "No, I had never used one." So, wow. This changes everything.
Digby Scott
So you do have a good answer.
Derek Sivers
Well that was just like my nerdy programming answer. I don't know if anybody else can relate to that. But I just mean, that was just a little one. That was Wednesday's answer. And then Thursday's answer was something else. And Friday's answer would be something around parenting. And Saturday would be something around eating. Sunday would be something around exercise. I feel like almost every day I'm looking at the way I live my life and saying, "Well, how else could it be?"
Digby Scott
That's it. And I think that's it, right? It's the question like that. So your question about, have I ever used this block of code or whatever, or how else could it be? Knowing to ask the question is the trick, right? And I think I'm inspired that you seem to be able to do that for yourself, and you've also had your Romanian friend and your old boss as people. How do you switch?
Derek Sivers
I just thought of one more funny example. I'm really embarrassed to tell you, if you were to come over to my house right now, you would see a disgusting jungle. A year ago, I started asking myself why I'm mowing the lawn. For who? I asked my kid, "Do you prefer the lawn mowed or jungle?" He said, "I like it when it gets long and jungly." I said, "So do I. Then who am I mowing this for?" So I stopped. And now my yard here is just completely overgrown like some really sad, scary jungle that you'd expect a deranged person to be living here. But the point is, realizing like those error messages, who am I doing this for? There's nobody I'm trying to impress. I don't have guests over. When I meet up with friends locally, we always go out to meet up on the beach or in the hills or whatever. And I don't have people over and I don't feel like mowing the lawn, so I stopped.
Digby Scott
Yeah, that's a beautiful example. Who am I doing this for? Is there another way? How could be there another way? Do I have to do this? All those sorts of questions, they're great circuit breaker questions to go useful not true that that idea you've mentioned those couple of people all right so your friend in Lithuania and your old boss I'm I'm wondering about how you think about, I don't want to use the word "use" or "leverage", but how do you bring people in? Where do other people play a role for you in that way, and how deliberate are you about that?
Derek Sivers
I'm very deliberate in who I'm friends with. I have six or seven really dear friends that I talk with all the time. And they're spread around the world, but we talk by phone. And the reason they're my dear friends are because we have great conversations. We both learn something from each other, we have a feeling of safety and trust so we can speak completely unfiltered and say all the un-PC shit without having to give disclaimers. We get each other. She can say something completely rude and I don't judge her because I get it. We learn something from each other. Somebody stays in my inner circle by continuing to surprise me.
Digby Scott
Oh, well, what came up for me was a reflection I had over summer in the last few months. I went back to Perth, the previous trip before this, and I was there for a couple of weeks, and I noticed there was sort of two forms of conversations I was having. There were conversations where I would be, it would feel like this beautiful blend of what you've just described as some awesome learning going on between two people, me and the other person. And I think that was format by there's lots of listening and there's lots of really great questions and deep inquiry questions, like "So tell me how you think about that?" and "What's lighting you up at the moment?" All these lovely questions. And it would feel really balanced and exploratory. And then there was another set of questions where people would pretty much ask no questions at all. And I would feel like I was just being monologued. And the first type of conversation I walked away going, "I want more of that. I love that. And I'm nourished. And I'm growing." And the other type was kind of like, "Hmm, why do I choose to hang out with this person. And so this idea of keeping, well, where I'm going with that is, I think I'm in a bit of an editing stage of who I want to hang out with. And it's not just friends, it feels like it's a broader, what experience of conversations do I to have with anyone. And I'm curious about your take on, maybe there's your personal experience of how you've come to choose it's a smaller group of friends, is it something like that? I suspect it is. But also what do you think causes a person on the other side of that conversation to not do the first version of Ask Questions. What's going on? And I'm really interested in that. Let's take this somewhere together conversation, whereas the second version is the the monologue, let me talk at you about my world.
Derek Sivers
I have a lot of thought about this. I think a lot about friendships. Because all of my friends are phone friends, except one. I have one local friend in Wellington. And then there's my boy who's kind of my default best friend. He's the person I talk to most in the whole world. We spend 20 to 30 hours a week just talking and have since he was born, since he could talk.
Derek Sivers
But every other friend is spread around the world and we call each other and have a very intentional phone call, usually about an hour long or so. And it's the only time that we're talking that week, so it's very deliberate. You can sense what a good conversation that was because it's so bounded like that. It's a one-hour conversation and it feels great or it doesn't. So there are many times when a friend is going through a lot. They're overwhelmed. They're going through a big change. They've got a lot on their mind, they're stressed out, and they just need to vent. They're not feeling super curious. They're not feeling super patient. They're not feeling like a really good listener right now. They're overwhelmed. And in those moments, you just have to be empathetic and patient and just understand in the bigger arc of friendship, he's going through a lot right now, he needs to vent. And it might be for a whole year that this friend of yours really needs to vent and is not a very good listener. And then you just have to ask yourself if is this a permanent situation? Have we created a permanent rut here where my friend is never more going to listen ever again? Or am I just being a really good listener from my friend who's going through a lot right now?
Derek Sivers
One of my best friend's mom just died suddenly, totally unexpected, otherwise perfect health. They were super super close and used to talk like four times a day. It was one of those kinds of relationships where they just ping ping ping ping ping talk to each other all the time all the day. And then mom was out scuba diving, felt a little lightheaded, just instantly dropped dead at the age of 60. So unexpected. And my friend has been absolutely devastated by this of course. And we've been talking almost an hour a day for months now, with me mostly just listening. And that's because she's not feeling super curious about learning new things right now. It's just processing. And I've been in the same position when I went through a breakup a couple years ago. I was a hard friend to tolerate because I had a lot I just needed to vent and share and commiserate and hear a friendly voice acknowledge my side of things. It was some hard times. So this back and forth that is the ideal can happen And if you're both in a good place, you're both open, you've got your lives pretty okay managed and you're able to ask questions and listen to the answers.
Digby Scott
There's a lot of empathy in the way you answered that, you know, and it's really helped me think about, yeah maybe I'm being a bit too selfish right around, you know, what do I need in a conversation? Because sometimes giving someone an ear is the best gift and giving is a powerful way of feeling good too, right?
Derek Sivers
And ideally, long term, it gets reciprocated. There are years when you're the needy one and years when they are the needy one.
Digby Scott
Yeah, that's awesome. Yeah, and I love your time-bounded hour a week. I have that. I had that with this three of us every Friday at 11am. The other two were in Melbourne, one's now moved to the UK and it's a lot harder now that he's in the UK with time difference. And I miss it because we We had it for a couple of years and that's now, we're doing more one-on-one, but the three-way of us was absolutely brilliant because we all gave each other roughly 15 to 20 minutes of time for us to be the one that was in the center of the conversation. And it was, that word reciprocal I think is key and having friends that can be that for you is gold.
Digby Scott
I also wonder in the day-to-day hubbub of working life, I notice a lot of broadcasts as opposed to dialogue. There's a lot of "here's my view, you need to hear this". And so that question about what's going on when someone is on broadcast mode, that second version of a conversation and I wonder about, is it because they're not in good shape personally, or is it this is just the way that we operate around here, that my job is to tell you what's going on in here. Any thoughts about that?
Derek Sivers
I think everyone should journal.
Digby Scott
Oh, tell us more.
Derek Sivers
There are very few things in life that I think everyone should do. Maybe this is the only one. Everyone should journal. Ideally, every day. Not just when you're feeling stressed and in need of a diary to cry into, but to just write down what you did today, what's on your mind, how you're feeling. It's sending messages to your future self that you can look back on to see what's ever changing what stays constant in your life, to look back at times in your life, not through the lens of forgetting over time, but the word from the actual moment when you were in that time in your life. It's so useful for so many ways that I will try to talk about more later on my website. It's worth me figuring out how to express this more.
Derek Sivers
But for the situation that you just described, somebody that just wants to go blah, blah, blah, blah, blah, blah, blah, blah, blah, blah, and have everybody listen to them. I think that person should have done that in their journal first. They have a need to get their thoughts out of their brain. And they're using you as their journal when they should use their journal as a journal, get all of their thoughts out of their brain, and then think about what needs to be said to others.
Digby Scott
It links right back to the slow thinking, doesn't it? It's the slowing down your brain, processing before sharing, really is what you're saying.
Digby Scott
What's your way of doing that? Do you have like a daily hour or a half hour or how does it work?
Derek Sivers
By the way, I feel like saying for the record, I don't have a designated hour that my friends and I talk. It just turns out to be about that way. We call each other while eating a meal or while running an errand or while driving from to another and usually after about an hour or so it's like, well, gotta go back to work, back to life. Thanks for calling. And it's not some set scheduled thing. It's just when my friend has a minute, we call.
Derek Sivers
Same thing with journaling. There's not a set schedule. Sometimes I wake up and journal right away because I've already got a bunch of things on my mind that I want to get out. Sometimes it's in the middle of the day. If something just happened, I just had a really profound conversation or a huge insight. Oh my God, I'm going to turn to my diary right away and start trying to capture this, record it for my future self. Usually it's at the end of the day, right before bed, when I'm winding down, about to turn off the computer, I've shut off all the devices and things, I will spend 15 minutes, 30 minutes just saying what I did today. It's all for the benefit of my future self to look back at.
Derek Sivers
That was the big inspiration. At the age of 42, I wished that I would have had a daily journal I could have looked back at to know what I was doing in my 20s. I have a few memories, but was I happy? Was I elated? Was I terrified? I don't really remember. I just have a few little snippets of memories. Damn, that would be precious to have a daily diary from my adventurous 20s. And well, I wish I would have had that, but the second best time to plant a tree is now.
Derek Sivers
So at the age of 42, I started keeping a daily journal and I never miss a day. And it has been so useful to help me look back at times in my life that were different than the current times.
Digby Scott
How often or what's the trigger for you to look back? Like when you go, "I'm going to open this and just flick through it."
Derek Sivers
It's rarely just a random walk. It's usually a specific question about how was I feeling at that time in my life? When I met my ex, did we click right away? I don't remember. I think we did. And then I'll read my diary and find out that no, we didn't. It was really difficult at the beginning. It took a long time. I will look back at a time I took a trip eight years ago. Was I happy on that trip? Should I take a trip like that again? That was a pretty extreme thing to do. What was I thinking at that time? Oh, it's actually better than I remembered. I think it had a bad ending, so I remembered it not so well, but actually, despite that last day, the rest of the trip was brilliant. I should do that again. Endings taint stories. Stories taint stories. And yeah, looking back at your actual recount of the day's events is a much more trustable source than your poor tainted memory.
Digby Scott
Yeah, yes, yes, memories taint stories. And it's a way of seeing a triangle versus you might be thinking about a circle, right? It's like, what's that perspective from 20 years ago, rather than my perspective now? Right? It's the same idea.
Derek Sivers
Actually, I'll use your cone in the cube metaphor. The journal is the point of view of the cone itself. It is the cone that is journaling. No need for the pinholes to look from different directions. The cone itself has a detailed journal.
Digby Scott
That is it. That's awesome. It's interesting that you use it for that purpose because I did morning pages for a long time, which I found had a different purpose. In fact, I think the rules or the guidelines were never look back at what you wrote down. It's not for that purpose. It was almost like a clearinghouse for your thoughts. Just get all the noise out of your head, not write non-stop for three pages and then shut the book and do it all again the next day. And I found that, I haven't done it for a little while, but I found that process really good to set me up for the day. It was like mental clutter, what's in there, let's just dial it down. And then what came through was, ah, here's what matters for me now, you know, as opposed to all the champagne-y stuff. It was more like settling to the red wine. And very different reason, but I think if we came back to the original point of this, which was everyone should journal so they can kind of think about what they want to share, both of those can be useful, both of those processes.
Derek Sivers
Yeah, I do use it 95% just for the present, like you described with morning pages. I use it just to sort out my thoughts, to get it out of the clutter of my brain into a slightly more structured format, which helps me think of it better. There's a therapeutic benefit to having to explain your jumbled thoughts to somebody else. I think a lot of the benefit of going to a shrink or whatever you want to call it, counselor, is that you have to explain this tangled knot of thoughts in your head, you have to get it out of your mouth to somebody else. And just doing that helps it straighten out.
Derek Sivers
By the way, anybody not watching on video, I'm doing that kind of action like the magicians that pull the ribbon out of their mouth. I just realized it is like that. It's like in your head, it's a tangled ball. And just trying to get the words out of your mouth turns it into a single stream it's less tangled, right?
Digby Scott
That's a great metaphor. Yes.
Derek Sivers
When you're in group therapy, I've never done this personally, but I've heard that when you're in group therapy, like AA type things, it has the further benefit in that you've only got a few minutes. You don't have a whole hour, and this isn't all about you. There's 10 of us here. If you wanna share something with a group, you've got a few minutes. You need to simplify your situation to explain it to the group in four minutes. And the very act of simplification helps you represent it to yourself in a simpler way, which then helps you feel better about the situation, going, "Oh, really? It's just that. It's not a giant tangled thing. It's as simple as this. Now I feel better about it."
Derek Sivers
Writing in the journal is a little bit like that. It takes some effort to write, to pull the tangled mess out of here, into here, and put it down. It simplifies things. It organizes them. It helps you go, "Ah, right. I can do this."
Digby Scott
I love that. It's a way of getting to simplicity on the other side of complexity, right? And to work through it. You know, there's a guy, Hal Gregersen, I think he's MIT and he came up with this technique called question burst which it takes I think it's like 15 minutes or something and you work in a group and you have two or three minutes to explain your problem or your challenge or your thing and that's it. I think it might even be two minutes. You have two minutes to explain it and then the group might be four or and you have someone writing down all the questions and you're not allowed to answer the questions at that time, you just have to listen. There's four minutes of questions, usually about 15 questions can come out, something like that. So there's all these questions and then you get to pick the one that might be most interesting to you to go down a rabbit hole on or explain or explore together and you might spend another five minutes doing that and then you go, "All right, where am I at now and what might I do next?" And that's it. And I've used this a lot in group settings, so it's not really therapy or counselling, it's more of a group problem-solving process, but I reckon it's exactly what you say. It's the first two minutes that makes all the difference. The questions can kind of give some colour and maybe some possible courses of action but it's the forcing of you to go what am i actually trying to say
Derek Sivers
Yes. What am I actually asking? What's the real problem? What's the real question? Try that before thinking that you need a mentor, before wishing that you had some genius mentor to tell you what to do. First, succinctly describe your context and your question and what's the actual problem. What is the one thing you don't know that you think somebody knows. And just formulating that into a succinct explanation of the context and the problem will probably solve the question for you.
Derek Sivers
I've even been using this with the AI LLM tools: ChatGPT, Claude.ai. Sometimes I go to them with a programming problem. But even to ask the question, I say, I've got this database table. I've got that database table. I need to join these two together. But just to ask the question, I don't give it the entire table with 27 fields and 13 fields here. I simplify it down to the two fields I have a question about. And I want to give it an example. So I create a little test John Doe Main Street ABC example to ask the question of. And once I've done that, I go, "Oh, I see the solution now."
Derek Sivers
That's always the winning approach, is to simplify the question, to define your actual question sharply usually will help you just see the answer clearly.
Digby Scott
I love that. You don't even have to press enter to ask.
Derek Sivers
Right. I end up deleting the whole question.
Digby Scott
Yeah, yeah. It's interesting actually, because the more I've done, I use Claude mostly, and and I find that I spend a lot of time defining my prompt, and because I know if it's a general broad thing, I'm just going to get wooliness back. And if I go really specific, I'll still press enter because I think maybe partly I just need some validation of what I think the answer is, but it's often "hmmm" and what else, right? So there's a learning piece to it. Yet the work again is in defining the prompt, defining the question, defining the request, so you can get really crisp feedback that is probably more i'm finding more and more it's about validation oh yeah i already knew that thanks awesome.
Digby Scott
Feels like we're coming into final approach coming into land here. There's a question actually before we get to the last question i want to ask you Is there anything that you would love to explore or share that we haven't or we've touched on?
Derek Sivers
No. I'm good.
Digby Scott
You're good. I'm good. So my last question is, I always ask this, is what have you learned through this conversation or been reminded of? Well maybe something that's become clearer as a result of us hanging out together for a bit.
Derek Sivers
I don't know. I love our exploratory conversations. You and I have met up twice in person, and now this conversation. And all three times we have a little random chit chat at the start and then we get into the good shit. I have such good memories of sitting with you at the Te Papa Museum in Central Wellington and talking about breakups and relationships and such good shit that I don't usually talk about with people. That was so fun to get into. And so today, I had a lot of fun getting into these subjects of slower thinking and pointed questions and the cone in the cube.
Digby Scott
Let's do it again. I mean, it's so long between drinks, metaphorically, right? Feels like it's been this, I don't know, all of this been waiting to come out in our conversations. I love to do it more often and I treasure this. It's been, it's such a rich exploration and talk about, you know, conversations that might be one way. It's felt like it's been an awesome learning conversation and a reminder that yeah, it's good to go deep, it's good to slow down. And so thank you for making the start of my day really rich and I hope for anyone listening it's just it feels like a get your glass of red wine....
Derek Sivers
You and that red wine!
Digby Scott
I'm actually not a big red wine drinker! But...
Derek Sivers
But in this conversation you are.
Digby Scott
So how can people get hold of you Derek?
Derek Sivers
Everybody should go to my website, sive.rs, and you should email me, because that is my connection to the world. I really like hearing from people.
Digby Scott
Thanks Derek, it's been awesome.
Derek Sivers
Thanks, Digby.
Digby Scott
See you soon.