Her Empire Builder
host: Tina Tower
importance of perspective, life transitions and changes, success and money
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Transcript:
Tina
Welcome Derek Sivers.
Derek Sivers
See, we’re beginning just like that. No intro. Hello.
Tina
I’m doing a little bit of a happy dance. I’m going to intro you later. So you don’t know why I first asked you to come on the show today. So I want to share that with you first, because I kind of alluded to it just before, is one of the things that I did when I started my podcast five years ago was I made a dream 100 list of like 100 guests that I would love to have on my show. And they’re people that I’m like, you can’t just pick up the phone and say, “Oh, hi, Derek Sivers, I’m Tina Tower from nowhere. Will you come and talk to me?” And so I’ve been waiting to go, I’ve got to, like, have some invisible line that I need to make it to before I am worthy enough of emailing and asking to come on the show. And this year, when it clicked over, I was like, this is the year I’m just going to start and ask the people on my dream 100 list to come on. And you are my first one. And you said yes, which I’m so happy for.
Derek Sivers
You want me to help with the rest?
Tina
Sure. I mean, some of them you might know. I mean, Celine Dion is on there.
Derek Sivers
I’ll ask her. She’s having a little trouble these days, but you know.
Tina
Yes, I have some very obscure ones of just people that I’m like, I want to ask all of the questions and have interesting conversations with. So thank you for being the first one.
Derek Sivers
You know what’s really cute? My kid, who’s 12, asked me just last week. He said, “You know, famous people, right?” And I said, “Yeah.” And he goes, “I mean, but do you know, like everybody?” And I said, “Well, depends who.” And he goes, “I mean, you don’t know Bill gates, right?” I said, “Actually, I met him twice.” I said “once in the men’s bathroom at the Ted conference, as you do. And another time at a bar in LA.” And he’s like, “You’re serious? You met Bill gates.” And so because that was the first one, he asked. Now he has the impression I really know everybody.
Tina
Yeah you know everybody. What was Bill gates like?
Derek Sivers
Oh, just.
Tina
Yeah, yeah. And on with it.
Derek Sivers
We’re not friends.
Derek Sivers
Okay, so caveat, the reason why you made it to my dream 100 list was the books that we have here. I love them. Well, I’d say I love them all, but the fourth one, I haven’t read it because it’s not aimed at me. But you’ve said read it now, so I will definitely read it later today. But I love that they’re digestible like that. “Anything You Want” is my absolute favorite. “How to Live” is probably the most frustrating book that I have ever read. But most interesting in going there, but with with all of the books that you have written and all of the different things that you’ve said. I’m not going to quote, I said I should have bought my original book because it’s got so many underlines and post-it notes in it. It looks bordering on ridiculous. And I stopped highlighting when I got to the third one because I’m like, it’s all just so good that I’m not going to quote any of it except one time, just this one thing. So you wrote in “Anything You “Want, “Most people don’t know why they’re doing what they’re doing. They imitate others, go with the flow and follow paths without making their own. They spend decades in pursuit of something that someone convinced them they should want, without realizing it won’t make them happy.” I read that and was like, so the reason I started reading that was I was at a really pivotal moment in my life where I was going, “I don’t even know what I want anymore.” When people say, what do you want? I’m like, “I don’t know.” What is your advice on breaking life’s rules and living on your own terms? If you’re going, you know this direction I want to change.
Derek Sivers
Talking with friends. I think when you realize that the way that things are going now are not working for you in some way, whether you’re just feeling lost or it’s like that feeling of like every door you try to open is locked, you know, metaphorically. I think, like, “How else could I be thinking about this? What’s another perspective I could take?” And even if I need to like put on an alter ego or ask myself, “What would this other person think? What would my hero think? What would this fictional character Samurai Jack do?” What would-- I don’t know, pick whatever your fictional hero might be, whatever it takes for you to think of your situation from another perspective. But then when you find one that you think like, “Ooh, I like that, that’s a new angle I hadn’t thought of. I could think this way.” Then it’s talking to friends for me. As I call up a friend and I’ll say, “Hey, what do you think about this?” Like, what if instead of thinking of what I’m doing this way, what if I looked at the whole thing that way? And then a friend will help echo this back to you, making it like a social reality.
Derek Sivers
You know what I mean? So friends do this all the time. Let’s just go down to like, the most basic, like teenage level. Like you meet a boy and your friends as a teenager would like, “Oh my God, that’s so good. He is great. You two are perfect together. Oh my God, you look so good together. You’re so happy.” And then two years later, or two months later, you break up and your friends are like, “Yeah, he’s awful. You were so much better without him.” And so friends already do this. They help echo back a way of looking at something and it takes the faint idea and starts to make it feel real when you get the social like echolocation. And then you talk to another friend and you say, “Hey, I’m thinking of taking this new approach to what I’m doing.” And your friend says, “Yeah, and if you do it that way, that means that this.” And then you go, “Yeah, I hadn’t thought about that.” Yeah and pretty soon these all start to feel like realities instead of an idea.
Tina
And like sitting in which one you think feels the most comfortable.
Derek Sivers
Yeah. Not comfortable.
Tina
Exciting?
Derek Sivers
I mean, I guess it depends on your value system. For some people. Yeah, it would be comfortable. For somebody else it might be exciting. For somebody else it might be like, I need to make a real change in my life, what’s the viewpoint that feels like the biggest change from how I currently do things? That’s that’s what I did after I sold my company.
Tina
I was going to ask you, like, have you had the existential crisis at different points in your life where you’re like I mentioned before, what got me here won’t get me there. When you get there and you go, I want to completely throw out every rule that I’ve lived to by now and let’s write a new set.
Derek Sivers
All the time. I don’t talk about it publicly much, but in short, I got into a really bad relationship. And then we had a kid together. So a lot of my philosophical deep dives have come around, like how to deal with my situation and my restrictions in life. I would like to be doing this. I am doing this. How can I be okay with it.
Tina
How did you get yourself into that?
Derek Sivers
Oh, come on.
Tina
The way it normally happens.
Derek Sivers
Yeah, she was hot. That was distracting.
Tina
Sorry.
Derek Sivers
But, you know, it’s so many times whether it’s like financially or it’s something in your personal life takes a major change or you’re feeling like done or stuck and you think, “All right, I need to make a real change.” So, okay, let’s pick a better example. So when I sold my company, you could say that it was like a success moment, but for me, it felt like a failure moment because the only reason I sold the company is that things had gotten so bad that I sold. I was such a bad manager.
Tina
That’s the same reason I sold my company.
Derek Sivers
You’re the only person I’ve heard say that.
Derek Sivers
Really?
Tina
Yeah.
Tina
Really?
Derek Sivers
Yeah.
Tina
Yeah, by the time I sold my company, I couldn’t remember a day where I didn’t feel nauseous or had a headache. And I probably didn’t have a week without crying for a year beforehand. Yeah. I built a beast. That was wrong way, go back and I couldn’t go back.
Derek Sivers
Wow. And that’s why you sold?
Tina
And that’s why I sold. Yeah.
Derek Sivers
And then people say congratulations, and you go, “Oh. I guess.”
Tina
I’m like, yes. But I mean, it’s helped now. I’ve built a beautiful company now that doesn’t have all of those things. But this is not about me. This is about you. So.
Derek Sivers
Well, no, this is nice to hear.
Tina
When you sold CD Baby.
Derek Sivers
Well, so. Literally the day after I had a deal to sell the company. It was my sister’s birthday, so January 18th was the day that we had this handshake deal, and I went to bed with like an empty head and a smile that night like, “Whoa! Done.” Like I am no longer Derek@cdbaby.com. Wow. How nice. The next morning I woke up, I was like, “Oh my God, my next company. I know what I want to do.” And I like dove into it. I started programming it right away, called the person I wanted to work for me. I was like, “You want to be the manager of this thing?” He said, “Yes, let’s do it.” So for three months I started this new thing. It was called Muckwork and I believed in it, completely, sketched it all out. We got three months into it and then I went, “Wait a minute, hold on. If I do this, I’m going to be following the same trajectory I’ve been on for ten years already. I want to make a real change in my life.” So, sorry, this has been a long answer to your original question.
Tina
That’s why we’re here
Derek Sivers
I started deliberately saying no to everything I used to say yes to. Saying yes to everything I used to say no to. Like deliberately going against my instincts over and over, like sometimes multiple times a day. So like, at every turn.
Tina
To just see how it felt?
Derek Sivers
Uhuh. So honestly, when you asked your question. I guess I’m answering two questions at once. You said, “How did you get into that relationship?” Yeah, exactly like this. I was passing through New York City and we had been dating for a few months. She said, “Oh, well, my parents said that we have to be married. If I were to come travel with you.” And everything in me said no. So I said yes. And you know, it was a good way to shake life up. To break your habits.
Tina
And when you went traveling, did you go wide traveling then, or was that when you went to New Zealand?
Derek Sivers
No. Went by traveling first. Yeah. And then, New Zealand wasn’t until a couple of years later. My son was born when I was living in Singapore and then I just wanted him to grow up in New Zealand.
Tina
So why New Zealand?
Derek Sivers
Nature.
Tina
Isn’t it beautiful? I really do think it’s one of the most beautiful countries in the world. Probably the most beautiful country in the world. We’ve got the rain pouring down here, which is lovely.
Derek Sivers
Yeah. It’s great.
Derek Sivers
So all the clicking you hear on the recording is the rain. So I think that’s what I do. So sometimes the new values you need can just be anything to scramble your old habits. The opposite of whatever you did before sometimes your value system might be like, “All right, you know what? I’ve been running too ragged. I want to take it easy. I’ve been pushing myself too hard. I need to go for a value system or a lifestyle design change, that’s going to be easy and comfortable.” But whatever it is. Yeah, I do highly recommend, as you can tell journaling a lot works for me. I spend hours in my journal just kind of turning ideas into reality in my head. And then calling friends, getting that kind of echolocation back from friends helps make things real.
Tina
Yeah I love that. How much internal conflict happens for you when you adopt that new belief system that is so different from something that you’ve carried for a really long time that you no longer want to carry?
Derek Sivers
For me personally when something feels unnatural, I feel like I’m on the right track. Yeah, but that’s just my weird personal beliefs, because it’s like, one of my favorite joys in life is changing my mind. So when I’m reading a book, what I’m hoping the book is going to do, obviously, is change my mind. That’s why I’d be reading the book, is because I want you to-- don’t tell me what I already know. I mean.
Tina
I mean that’s what “How to Live” definitely does.
Derek Sivers
Thank you. Like, change my mind on something. That’s what I’m here for. Like, that’s what I want. And so I feel that in life too, that I want to try on a new way of thinking. Yeah, that’s my greatest joy.
Tina
So before we hit record, we were talking about changing and people changing because I pointed out that my Enneagram had changed. And you said, do people fundamentally change? So would you say you change through each of those times?
Derek Sivers
Yeah, yeah. Yeah. When somebody asks why I don’t make music anymore. It’s like, oh, that was previously me. Yeah. Same name, same bones, but very different soul.
Tina
Because I would say--. I mean, I’ve been with my husband since I was 18. We have our 20th wedding anniversary next year, which I’m very happy with, but I go, I think it’s nothing but luck because I would say he’s a wildly different person than when we met. I’d say I’m a wildly different person. But it’s like each evolution we’ve really liked and that’s been nothing but luck in there. But we talk about it sometimes and go like, “If ten years ago could see what I do, like she would have been going, ‘No way. Like that’s not what we do.’” I’ve become a lot more introverted as I’ve gotten older, which I think I always was, but masked quite a lot. And I think that’s a lot of what we do in our 20s and 30s, that we mask a lot of our natural tendencies to try and fit in with everybody. But did you do that as well, like when you ran CD Baby and you were going like more and more, I want to conquer the world. Was that innate? Like, was that innate?
Derek Sivers
No. I think that actually the want to conquer the world thing, that was more my musician years. I was trying to be a successful, famous musician. Then when I started CD Baby, I felt more like the metaphor of the athlete that used to be in the spotlight and is now on the side of the court just being a coach. No CD Baby. To me, I was very unambitious.
Tina
Even though the success you had, there was probably way more than 99.9% of musicians.
Derek Sivers
Yeah. Well, no, I’m saying that like my drive was like from the very start, like literally, three months into starting it, I realized, like, “Oops, I’ve started this thing.” And so I said, “Okay, well, since I’ve started this thing by accident, which I didn’t want to distract me from my music career. As long as I’m going to do it--.” Sorry I haven’t read the book in a while, but it’s in there. But I kind of set this criteria. It’s like, well, in a perfect world, the perfect music distribution company would look like this, you know? Give me the full name and address of everybody who buys my music. Never allow a paid placement. It’s not fair to those who can’t afford it. Never kick me out for not selling enough. And I want to get paid every week. That would be my dream come true as a musician. And I knew that by doing this utopian ideal that I would be limiting the growth of the company. Because if I allowed paid placement, “Yeah, bring it on. Just pay me if you want to be in this thing.” You know, then that would have grown the company bigger. People later came to me and say, “Hey, as long as you’ve got this infrastructure in place, you could be selling porn and you could make a ton of money.” I was like, “I don’t want to make a ton of money.” What do you mean? Wait, what? Yeah. Hold on. I think I might have heard you wrong. I said, “No, look, I’m not doing this for the money. I’m doing this because I’m making this utopian ideal of a thing that should exist.” So no, I think my CD Baby years were very unambitious. I was trying to limit the growth.
Tina
I find that so interesting. You know, I used to hear people say things like that, and I used to think they were lying. If I ever heard someone say, “I’m not doing it for the money.” I’d go, “Yeah, right.” And now I don’t work for the money but I wouldn’t have believed me before. Was that always like when you say you wanted to be a musician and you wanted to be successful and famous, did it have anything to do with the money then?
Derek Sivers
No, not the money, no.
Tina
You never had the financial goals?
Derek Sivers
No, I don’t think so. I think at one point, ever. In one early little brainstorming session, probably when I was like 21, I think I might have written, you know, $1 million by the time I’m 30 or something like that, but it was just one of you know, 100 things I wrote down when thinking, it was nothing I took very seriously. To me, the dream was always to to be great. It was always what I wanted to be, in fact, oh, okay. So did you ever read Tony Robbins “Awaken the Giant Within”?
Tina
Yeah, I was like Tony Robbins. When I was 18, I thought I would be the next Tony Robbins. Yeah. I was a damaged teenager. I found Tony Robbins like, people find religion. And I was like in. So yeah,
Derek Sivers
Yeah. Me too. So the thing that bothered me the most about his message was where he goes on and on about the things you want to have, where it’s like, “Don’t you want to have a castle? Don’t you want to have a helicopter? Have your own private plane?” And with everything, I was just like, “Oh, God. No. That sounds awful.” Even as, like, 17 years old, I was like, no.
Tina
See, I thought I did when I read that, I was like, “Yeah, you’re right. Yeah, I do need that.” Even this morning I went onto Facebook and I read in-- I used Kajabi as the software for my courses, and I read in their Facebook group someone that had just made $10 million and was sharing their tips, and one of their tips was, “Buy the Ferrari, not the Hyundai, because of the respect you get from people and the people you meet. It doesn’t matter if you go into debt. Because you can pay it off over 40 years.” And I was like, “Oh, no. No.” But there’ll be a lot of people that read that that go, “All right. That’s what I have to do.” And that is one of the main reasons I wanted to talk to you. I’m like, that needs to be amplified more as multiple ways of success that doesn’t only look like a private-- I mean, why would you want a plane really? If you’re Taylor Swift, I understand she’s flying everywhere for her job. Totally get that. But for most people, I don’t think that’s--.
Derek Sivers
Yeah. And most people listening to this probably aren’t trying to decide whether to get a plane or not. No, but it can come down to-- God anything. Yesterday I was sitting with a group of people at this event I’m at, which are a bunch of, like, millionaire coaches. Okay, so I’m sitting with this group of five guys, and one of them sitting next to me says, “Hey, do you have a watch?” And I went like this. I pulled out my phone. I said, “It’s a 12.” And he goes, “I know what time it is. I was asking if you have a watch.” And then I looked around because he said, “You’re the only one here without a watch.”
Tina
Like a fancy watch?
Derek Sivers
Yeah. And I looked around and sure enough, all five guys had fancy ass watches. I just never really looked at men’s wrists. Yeah. And I was like--
Tina
As for you never looked at men’s wrists.
Derek Sivers
I was like, “Do you not have phones?” And he’s like, “Oh, it’s not about that, mate.” And he gave me his thing.
Derek Sivers
He said, “Oh, it’s something, you get yourself to say that you’ve arrived. You know that once I make this much money, I’m going to get myself a nice watch” He said “it’s like a status, like I’ve made it. I got this watch.” And I was just sitting there feeling so alienated. I was like, “I’ve never owned a watch. I can’t even imagine why--”
Tina
What was it about?
Tina
Do you have any jewelry?
Derek Sivers
No
Tina
None.
Derek Sivers
But because I get too philosophical about anything. It’s like, why would I need a watch? Like I would never just go get a watch. I think, what would I need that for? Or okay, no, it’s not about telling the time. It’s a piece of artwork. It’s like, well, are there different kinds of artwork I could wear on my body if I wanted to wear artwork? Like, why would I want to wear artwork? You know, because it will communicate status. Why would I want to communicate status? Would somebody do something for me because I’m communicating status that they would not if I did not?
Tina
Probably.
Derek Sivers
But are those the kind of people that I would want to work with? I’m like, who am I trying to attract, somebody that would be impressed by a watch? I don’t like those people. And s to me, I get too--
Tina
I’m feeling judged by my watch right now.
Derek Sivers
No, but see, that’s that’s a functional.
Tina
You know I wear this watch purely because I’ve just decided to hike Mount Kilimanjaro in October with my friends as part of our work for wellness. This ass is currently not getting itself up mount Kilimanjaro, so I’m really trying to increase my steps. I’m data driven and I like the data. It’s my defense of my watch.
Derek Sivers
Look if for maybe the other five guys that were standing there with their fancy ass. Yeah. Philip Patek, whatever that was called.
Tina
I don’t know her. I only know old school, like Rolex.
Derek Sivers
Yeah. Yeah. Same.
Tina
Mind you, I did see an ad in the airport, and I took a photo of it because I thought it was one of the most beautiful ads I’d seen. That was a watch ad not long ago. That was I can’t even remember the words now that I’ve brought it up, but it was like a father and a son, and it was the watch. And it said, “What will you pass on to him?” And it was like that sort of rhetoric. I was like, “Clever. Clever.”
Derek Sivers
Clever lie.
Tina
Yeah.
Derek Sivers
Yeah, yeah. Nice try.
Tina
But I could see how it worked. I was like, I can see men seeing that and going, “Yeah, I want to pass my watch on to my son.”
Derek Sivers
Okay. On that note, since we’ve totally taken a fun tangent.
Tina
I know, I’m totally off my questions.
Derek Sivers
We can come back to the track anytime we want. I thought, oh, God, I’m about to reveal something a little embarrassing. So I thought it would be good for my kid to have an EU passport. Just open up opportunities for him. So there are a few ways to do it. So starting in 2012, when he was born, I tried the first way, which was to become a legal resident of Belgium by incorporating a company in Belgium, spending enough time in Belgium and paying your taxes there for enough time that Belgium will make you a citizen if you’ve been doing that enough. I did that, but my immigration lawyer didn’t tell me that I had to file a certain form and suddenly, poof, my Belgium visa was gone. I was like, “Damn it, I would have had to start all over again.” So I looked for other options. Portugal came up and so in 2014, I became a legal resident of Portugal. The deal in Portugal is show up for two weeks per year for six years in a row, and after six years, you’re eligible for citizenship.
Tina
Yeah I’d go to Portugal every year for six years. Yeah. For sure.
Derek Sivers
You would? I thought you said okay.
Tina
Yeah good deal
Derek Sivers
So 2014 plus six is.
Tina
Oh 2020. Oh, no.
Derek Sivers
So New Zealand with its closed borders. I couldn’t go back to renew. So on my sixth year when I was finally eligible, that’s exactly when Covid began and New Zealand borders were closed for two and a half years. So I could have left, but I couldn’t have come back. And so after six years, my Portugal thing disappeared. So then there’s one other option that somebody said in Malta you can--
Tina
Another beautiful place.
Derek Sivers
You can pay €800,000. So basically $1 million.
Tina
It sounds like a green card in America.
Derek Sivers
And they will essentially, if you have a good background and you’re a good person, they will make you a citizen of Malta, and then that will pass down automatically, not only to your kids, but to their kids, whatever. So for a minute I considered it. And I was talking with a friend of mine. See, I like to do this echolocation thing a lot. So I was like, “Hey, what would you think if I did this for my kid?” And he goes, “Well, your kid might enjoy having an EU passport.” And he said, “I think he would definitely enjoy having $1 million.” And I was like, “Enough said.” Ding ding ding ding ding. The winning answer has been reached. So as for the fancy ass Rolex to pass down to your son. I was like, “Yeah, how about the $40,000 that you would spend on the watch. I think your kid would like $40,000 better than your fucking watch that he did not choose himself.” So, you know anyway, this is why I don’t have nice things.
Tina
Yeah, I have a question about that later, but I’m going to try and stay on track. It’s very interesting. Likee you know, I am off track already, but that’s okay.
Derek Sivers
We can follow whatever tangents you want.
Tina
Everything you say, I’m like, but what about this? So what does your daily life look like now? Because you’re still working. You’re working on what you feel like. You’ve got your “Useful Not True”.
Derek Sivers
Yeah. Like, right now I’m just writing. I mean, I answer emails. But that’s just like, you know, half an hour a day.
Tina
So let me ask about the email thing, because you put your email address in your books and you say, email me.
Derek Sivers
And I love it. My email box is so wonderful.
Tina
How do you keep up with that?
Derek Sivers
It’s manageable. You know, I’m not a Hollywood star.
Tina
Like you’re getting hundreds of emails a day.
Derek Sivers
No, I get maybe 50 a day, 50 to 100 a day.
Tina
Still a lot of emails.
Derek Sivers
Yeah, but most of them are just sweet compliments.
Tina
Yeah. And you write back to everybody.
Derek Sivers
Yeah.
Tina
Wow. That’s cool.
Derek Sivers
But God, sometimes, I mean I don’t do social media. So a lot of the hit that people get from swiping things and scrolling things, it’s all in my email inbox. So, I just yesterday got an email from a musician in Turkey that we were having this, like, interesting philosophical conversation about beliefs and choosing beliefs and whatnot. And then the next email was from a writer in Gaza, born and raised in Gaza, and he had just told me last week he introduced himself and said, he’s a fan of my writing and told me more about his life. And then I asked something about, “Oh my God, did you grow up in Gaza? And how is it now?” And he said, “Well, my two cousins, my like, childhood friends were both killed in the war, so far. And I said, “Oh, my God, I’m so sorry. That must have been so devastating”. And he replied back, saying, “Actually my home had already been destroyed and a lot of my friends were killed. So honestly, by the time I got the news that my two cousins had died, I was already pretty numb.” And like, we were talking about that.
Tina
What do you say to that?
Derek Sivers
We talked about it. I don’t remember what I said, but like, it was, I was just sitting there going, “God, I love my inbox.” Like, this is amazing. And oh, I know, because in that same email he said, “Let me tell you the better ways to enter now. Go to Jordan first and come in over. If you’re going to the West Bank, come in from Jordan or if you want to come see me in Gaza, come in through Egypt.” He said, “come to my home. We will take care of you for as long. I’m the only one that speaks English in the family. But I’ve told my mother about you, and she can’t wait to make you the best hummus you’ve ever tasted. You come stay with my family.” And I’m like, oh man, I love this. Yeah, I love my inbox.
Tina
That must feel incredible to have reach globally.
Derek Sivers
Yeah. I mean it’s one of my favorite things. I think it’s the reason I’m always giving my email address saying, everybody email me. I really love meeting these people. Okay. The Gaza guy, that’s extreme. But even just meeting like, you know, “Hey, I’m a swimming instructor in Vietnam.” I’m like, cool. I know a swimming instructor in Vietnam. That’s so cool. And then what I love is that when I go traveling, I contact these people and I’m like, “Hey, I’m in Bangalore, let’s meet.” I’m like, cool. I get to meet up with a bunch of people in Bangalore, India, and now I’ve got friends in Bangalore. It’s a wonderful feeling. I impulsively when I lived in England a few years ago, I impulsively, I was like, “I’ve always wanted to go to Finland. I’ve never been to Finland. Going to Finland tomorrow night.” And because, you know, it was like $30 and one hour.
Tina
It’s amazing.
Derek Sivers
And so I popped over to Finland and arrived at midnight, sent out six emails to six people I know in Finland. And the next day I’m sitting naked in a sauna with a dude from Finland that brought me to his favorite sauna on the coast.
Derek Sivers
Right? Yeah. I was just like, I love this. So yes, that’s why. Yeah. Anybody listening to this email me.
Tina
I mean, it’s what you do in Finland
Tina
Yeah. We’ll put it in there. I’m just having all the Finland flashbacks coming through. Magic magic place. So no social media. Why no social media?
Derek Sivers
I just don’t like it. It’s like, why no reality TV? It’s like once or twice I would pass by a one of those reality TV shows are like flash flash flash flash flash flash. So I kind of feel the same way about social media. I just don’t like it.
Tina
Interesting. Have you ever felt like you should, or that you needed it for something and it wasn’t there, or you just totally switched off from it?
Derek Sivers
It was invented after I was successful.
Tina
I didn’t need social media.
Derek Sivers
I mean, every now and then, okay.
Tina
Such a good line, it was invented after I was successful, I was already there.
Derek Sivers
This event that I’m at with these coaches, people like the humble dude sitting next to me makes $20 million a year advising Australian e-commerce businesses on how to optimize their Facebook ads. That’s all he does and makes 20 million a year doing it, which means they’re making more than 20 million a year doing it. And I’m listening to this going like, “I think I need to adjust my beliefs sometimes.” If your beliefs are too far from reality you know. Like, I don’t know, I was about to try to. I mean, it’s like.
Tina
I mean it’s like a dream to drop off the grid. I did 90 days without social media like that was it when we traveled around the world for a year. I did 90 days and switched everything off and like it felt wonderful was one thing that I was like, I would love to live without social media, but there is so much that I think that I would miss business wise, connection wise, relationship wise. So many friends that I have met have been through social media that we’ve started out like mutual fans and then become friends from there as well, that I would miss that part of it. But yeah, the constant connection, wouldn’t miss that at all.
Derek Sivers
So that’s why it seems like, well, if you feel it’s important for your business, maybe it would be good for like an assistant to do that instead of you. But on the other hand, like you said, if you’ve got some pleasure out of it. Especially like personally if you’re not just saying, “Well I have to do this for my business.”
Tina
Yes, so you do and maybe social media does have a little bit to do with this too. You do keep your head in the clouds somewhat, being able to think the big thoughts and do all your philosophizing.
Derek Sivers
Sure.
Tina
What’s the word?
Derek Sivers
Sure. Yeah why not philosophizing? Sure.
Tina
I don’t think so. But doing that, how do you keep your head in the clouds? And do you succumb to the daily stresses of life?
Derek Sivers
That’s right. I didn’t answer your question, but what I do all day.
Tina
Oh, yeah. Yeah.
Derek Sivers
I mean, it’s the same kind of question. Yeah, I wake up and I write. So I mean, actually, I wake up with my son most of the time that you know, either he’ll jump into my bed at 6 a.m. or yell for me to jump in his. So we always kind of like cuddle and talk first thing in the morning and just kind of like talk about life or whatever. And then he goes off to school.
Tina
And is he a big thinker too?
Derek Sivers
Yeah. Yeah. I mean, in his own way. Yeah. It’s really sweet. He will be out playing and he’ll be like, “Hey, dad, can we just sit down here and talk about life?” Like it’ll be wonderful. But yeah, he goes off to school, and then right now I’m just trying to write the new book that’s like monomaniacal focus is like, okay, every now and then I want to, like, lift my head up and go, “Oh, what else could I do?” I’m like, “No, shut up, shut up, shut up, shut up. Gotta finish this thing.”
Tina
Are you on a timeline for it or you just want it done?
Derek Sivers
I just want it done. Yeah. I feel like ten months pregnant. It’s my metaphor of just, like, get it out. Yeah. I’m done. But there are other times. Okay, so say like once the book’s done, then I can imagine throwing myself into another thing, like saying, I’m going to make my sivers.com bookstore be multi warehouse. So I’m going to have a warehouse in Germany. I mean it’s already ready to go, but I’m going to have to make it so when you buy my books it’s going to ask you where do you want it from. And so now I’ve got to do the coding that’s going to manage inventory in multiple locations. It currently doesn’t do that. And so I know I’m going to be programming for a couple of weeks. I’m going to be programming a thing for the--.
Tina
You still want to do all of that yourself?
Derek Sivers
I enjoy it, yeah, I have actually a few times I considered outsourcing it, but I really enjoy it. As I said, no, this is the thing that I love. It makes me happy. So then I’ll just throw myself into that for a while and then that’ll be done. The thing I don’t like doing is like, “I’m going to do this for an hour and this for an hour. And this for two hours and then 30 minutes of this.” And when I have a day like that, I just feel like today sucked. And the days that I’m happiest are when it’s like I wake up at 6 a.m. and I do one thing all the way till midnight, and I go to sleep and I’m like, “Oh my God, that was amazing.” And it was sweet that like that I’ve got good friends that I’ve known for so many years, and a few of them have said back to me, like, “You know, in all the years I’ve known you, you always do this. The days when you do one thing from like 6 a.m. to midnight are the days that you tell me you were the happiest. That’s been really consistent through the years.” So now I know that’s like, it’s a good reminder to steer my life that way. So one of your questions we kind of hinted at but haven’t dove into yet is like making these life decisions. Like how do you know what to do? It’s like sometimes you just look at your past and you notice things about yourself. You’re like, “I could do this or this or this, but then it’s like, you know what? Every time I do this, I’m really happy.” And so, yeah, follow that path. Learn that about yourself. Yeah.
Tina
Are you a daily habits person? Like, you’ve got to wake up and do this and then this and then this. I used to think-- so I read Robin Sharma’s “5 a.m. club” book like many, many moons ago and was like, “Okay, successful people get up at 5 a.m.” So I did that, and then I worked out and did meditation and journaling and all of these things. And I did it for about six months and I was miserable. I had a headache every day. I was cranky, and I was like, “I can’t be successful because I can’t do the daily habits.”
Derek Sivers
You’ll never be a success.
Tina
I’m never gonna make it. And then realized, actually, I can wake up really slow and I can hug my kids in the morning and lay there and chat in bed, and then sit on the back deck and just slowly drink my coffee. And that’s totally fine. So I was curious if you had habits.
Derek Sivers
Not at all. Really. None. No. I think it’s interesting--.
Derek Sivers
None. None. None.
Tina
None?
Tina
Wow.
Derek Sivers
Yeah, not a single one. I mean, there’s some things that I generally do. I generally like to make a cup of tea in the morning. How’s that for success? “The key to success generally make a cup of tea” Says Derek Sivers. So in the music business, yeah, there’s a beautiful metaphor that or comparison that they would say for years, you can’t be a success in music unless you go on tour. But then hip hop artists would just, like, release a single with no tour and it would be like instant smash hit. And okay, well, you know, they say, “Well, you can’t be a hit unless you’re on radio.” And then these heavy metal bands would, like, sell out arenas all the time. They’ve never been on radio in their entire history, you know, Iron Maiden or Judas Priest or whatever. And so anytime somebody tells you “No, no, no, here’s what you need to do.” It’s like, all right, that’s one way. It’s not the way. But the person saying it believes it’s the way usually out of self-interest. You know, somebody who’s involved in the in video editing will tell you what you need to have a well-edited videos. You cannot be a success without well-edited videos. And somebody else will say, “No, no. the key is self publishing books. That’s the key to success.” You know. Anyway.
Tina
It’s probably the most difficult thing that I find about being a coach, and I think probably the most frustrating thing about people that work with the people that work with me would find is I don’t have the one way. I don’t think there’s ever one way. I think it’s different for different stages and how you want to live and what you want to do and what your natural tendencies are, which can be really frustrating for people. So like, just tell me exactly what to do. But there is no exactly what to do. And I think it changes all the time and it should change all the time.
Derek Sivers
Although okay, so but I also get this desire, the just tell me what to do. I often want that for things that I don’t care about that much. If I really want to nerd out on a subject, then I don’t want you to just tell me what to do. I want to explore this. But for some things. So for me, it was like, let’s take diet. I don’t care to read a 900 page book about the science of protein. I’m not going to read that, just tell me what I’m supposed to be eating. Just tell me what to do.
Tina
Yeah. That’s true.
Derek Sivers
And, I don’t need a custom diet. Just tell me. Wake up, make black beans with a chicken breast like this.
Derek Sivers
No, no, no, I’m just saying, if somebody were to tell mw.
Tina
That’s your breakfast?
Tina
Inside into Derek Sivers.
Derek Sivers
No no no no no no, I’m just quickly like say, for example, if somebody would say the, the optimum diet is for you to just wake and eat this and this and that and twice a week do this, I’d say, “Okay, thank you.” I don’t even need to hear your rationale. I see your PhD, okay just tell me what to do. So I understand that I did that technology wise when I wrote this page on my website that was dozens of hours of my life making this thing called “Tech Independence”. And I very deliberately did the just tell me what to do approach, because there are unlimited numbers of articles saying, “Well, you know, there are 15 different hosting companies you could use. There’s many different options you can use for software.” I’m like, “Okay, here’s a path for this. Go here. Type this at this site. Do that. Voila. Look, you now have a working email server. Web server, DNS, calendars.” I’m like there. And people say, “Well, why did you choose that one company to recommend?” I’m like--.
Tina
It was just the one.
Derek Sivers
I mean, I’ve used them, they work. And the whole point was to just pick one. So I do think it’s really handy to just tell people what to do.
Tina
Yeah. For things like that. I was having the conversation with Dan, who’s videoing us right now, before and saying, “I need to set up this sort of setup at home. And I was going, I have everything. I have my tripod, my cameras, my screens, the mics. Like, I’ve got it all. I don’t know how to put it together and I don’t know how to make it all work.” Like the camera store saw me coming and I was just going, “Yeah, I need everything for the setup.” And then was like, “Whoa, you should like do the process going, this is exactly what you need, how to set it all together, how to do it.” And I just follow it step by step. And then you’d be done.
Derek Sivers
Yes. Perfect example. Yeah.
Tina
Yeah. So we need that way. But how to live? Probably not.
Derek Sivers
Although Brian Eno, who’s a wonderful music record producer, said that the job of being a producer is to having strong opinions, so a band like U2 or Coldplay will hire him to come into the studio. And have strong opinions, he’ll say “No, I think we need to completely delete the drums from the middle section.” And they’ll say, “What? No, the drums are important for the middle section. No. It’s crucial.” He’ll say, “Okay, great, glad I could help. Now you know that the drums are crucial. The fact that you disagreed with me so strongly, I’ve just done my job.” Yeah. So if you could just come in and say, “All right, here’s what you need to do. 5 a.m.” And if somebody says, like, “I can’t do it, I want to die.” It’s like, great. Okay, now we know that’s not for you.
Tina
I knew I was never a morning person again.
Derek Sivers
But you know, at least we started with strong opinions. And now you know that won’t work for you. But I guess that it takes some self-awareness to know that that’s not working for you.
Tina
Yeah, totally. So self-awareness segways beautifully into self-discipline, which you have a lot of. No?
Derek Sivers
Sorry, I mean, didn’t mean to interrupt.
Tina
Well I would think I mean, from reading I mean, I have gone down the Derek Sivers rabbit hole pretty far, and you do seem to say yes to the things that are important to you and say no to everything else so that you can leave that time to create the things that are important to you. How do you stay in service to that highest priority? And not because-- I imagine you would get invitations to do different things and different opportunities, and partner with people for different companies and all sorts of things that are spread everywhere. How do you keep it true to what you want to do?
Derek Sivers
Mostly it’s the same answer when you asked why I’m not on social media.
Derek Sivers
I just don’t like it. I don’t want to live that way. Like I said, I don’t like those days where I do a little of this, a little of that. I like to throw myself completely into one thing at a time. So if--.
Tina
You just don’t want to?
Tina
But even though, like, I just don’t want to. And I mean, maybe this is a character flaw of my own as well. But there’s plenty of things that I do that I don’t want to do.
Derek Sivers
Why?
Tina
Why? Obligation.
Derek Sivers
Okay. Wait. Social, personal obligation?
Tina
Yeah. Personal. Like I said, I’ve become more introverted as I’ve gotten older. Like I say, say yes to a lot of things because I know it’s good for business. I know it’s good for relationships, when really I just love to sit at home with my kids and my dogs and do nothing and write romance novels.
Derek Sivers
You can.
Tina
I was having this conversation with a friend of mine the other day, he’s like, “What if you did, though?” I’m like, “Well, that’s easier said than done.” Like, there goes our home, our school, like the school the kids. Like so much of our life as we know it would have to change. Yeah.
Derek Sivers
And?
Tina
Yeah. I know, so you sit there and you go like you actually if you feel like you’re like, “Well, do I want to do this? Maybe not.” You just go, “No.” And not worry about any of the follow on consequences. That’s so cool.
Tina
I think not many people would do that. I think it’s a nice thought that most people would want to do, but I don’t think many people in practice would actually live like that.
Derek Sivers
I think it does require the self introspection to know what works for you and what doesn’t. So I think I’ve tried lots of ways of being. Yeah, I tried starting a record label to help other musicians. I tried running a booking agency. I tried doing this, I tried doing that. I tried lots of things. And I just noticed in myself, like, I don’t like this.
Tina
And you never feel selfish?
Derek Sivers
Oh, often. Being selfish is not a bad--. Okay, wait. Let’s talk about this in a second. Yeah. So there’s a chapter in my new book called, oh, damn. Sorry never mind. I’ll get back to that in a second, “Needy, stubborn, inappropriate flirt”. And I think selfish would be in that list, too. The adjectives that we act as if they are facts, as if they are traits of someone. You know, that person is blonde and selfish. This guy has red hair and he’s needy. But if you dig into those words for a second, you find that they have hidden judgments inside them. I once had to pick apart the word needy because somebody said needy, and I kind of stopped. I was like, “Wait a second. What does that really mean?” We looked at it. And what needy means is they act like it’s a trait of the other person. Yeah, needy just means somebody wanted something from me that I didn’t feel like giving. So now I’m calling them needy.
Tina
I’m super needy.
Derek Sivers
Are you saying, you’re saying--
Tina
I’m super needy.
Derek Sivers
Okay, well, but see, you’re making this judgment.
Tina
You’re saying when people call someone else.
Derek Sivers
Yeah. When you say the judgment is needy. But what they’re really saying is, I couldn’t give that person what they wanted. And so I’m going to call them needy to make it their problem, not mine. I’m righteous and perfect. They’re needy because they want something from me. But, okay, so selfish to me is like that, it’s secretly passing a judgment that you shouldn’t be looking out for yourself. You should be beneath others. How dare you not be beneath others? Yeah. I’m like, I don’t know, selfish to me sounds like a pretty positive adjective. Yeah. So is smug. Smug, I know it’s meant to be negative, but I think you smug is--
Tina
When you said the word smug. Then I could just imagine, like a meme of you, like.
Derek Sivers
Yeah, yeah, that is the smug, isn’t it? But it’s smug means that you’re living in alignment with your values. Like I’m walking the talk.
Tina
Yeah, here I’m happy with my life.
Derek Sivers
I’m happy with my life. I’m proud of my actions. I’m making choices that I feel good about. And then smug is the result of being happy with your actions. So why should that be a bad thing? I don’t know, it’s odd that we have these, uh.
Tina
So cohabitating. Can you do that? So when you’re cohabitating with someone.
Derek Sivers
That means living, right?
Tina
Yeah.
Tina
Yeah. Like you’ve got a kid. Do you live with a partner at the moment or?
Derek Sivers
Right now? No, no.
Tina
So you’ve got a kid there though, so you can’t be making selfish decisions all the time.
Derek Sivers
Right. So a friend and I were talking about parenting last night.
Tina
Yeah, like, say your head deep in the in the book and you’re like, halfway through the chapter and you’re in flow and it’s your jam and you’re thriving. And then your kid’s like, “Dad, we want to go here and explore this thing.” And you want to do both.
Derek Sivers
So right now my value system for parenting is, I’ve done this since he was born. Like I said he’s 12 now so for 12 years I always just do the right thing whether I want to or not. So I catch myself for a second. I know because a friend of mine is pregnant and we were talking about what’s to come. And because it will be her first. And she was saying that, you know, everybody’s scaring her.
Tina
Oh, really? It’s the most wonderful thing ever.
Derek Sivers
Yeah. So I said, “Look, there’s this moment--”
Tina
Can’t believe people scare pregnant women.
Derek Sivers
There’s this whingeing, do we use that word here whingeing?
Tina
Yeah.
Derek Sivers
Okay. That’s a good word. So people I think, like to kind of complain to get the little sympathy. Oh, you know, just wait till they’re two years old. That’s going to be hard. Oh, we’ll just wait till they’re six.
Tina
You know that I’m the parent that parents hate because I love it. And always I raved about me and they were like, “You know, just wait till they hit the terrible twos. You’ll see.” And then the twos came and they were like cute little puppies. And I loved it.
Derek Sivers
Yeah.
Tina
And then they were like, “You know, just wait until they start school and they’ll get all bratty.” And they were wonderful. And then they were like, “Wait until they’re teenagers. Teenagers are a nightmare.” My teenagers are freaking awesome. And it’s only now that they’re old enough that I feel like I can say we did good. Because you always live in fear that maybe, like, we’re not done yet, this could turn. Yeah.
Derek Sivers
You know, and then the heroin.
Tina
I feel like I’m far enough to go. No, no. We did okay.
Derek Sivers
Yeah. I’m the same. And that exact same thing you said too. That when the terrible twos didn’t come, they said, “Well, just wait till he’s six, then you’ll see.” Okay.
Tina
See we shouldn’t do that to each other.
Derek Sivers
So yeah, my approach to parenting is when he’s like, “Dad, come crawl on the floor with me” or whatever. My head is like, “Oh, I fucking don’t want to.” And I just take a second. I’m like, “Okay.” Cause I know it’s the right thing to do.
Tina
Yes.
Derek Sivers
So, you’re right. That is not selfish. Okay, maybe I wasn’t--
Tina
Because the value becomes higher when it comes to your kid.
Derek Sivers
Right. So maybe I’m not saying, you know, everyone should always be selfish all the time. I’m just saying it shouldn’t necessarily be a bad thing. I feel like we have, like, three open tangents right now.
Tina
No. I’m good.
Derek Sivers
No, wait, but hold on. You were asking about.
Tina
I was asking.
Derek Sivers
What was the context of that last one?
Tina
The context of it was, how do you hold yourself to your priorities when it’s so noisy?
Derek Sivers
So I moved to New Zealand so that my kid could grow up in nature, but maybe even more importantly. I’m sure there’s a place in Northern California that has a lot of nature that I could have lived. I deliberately put myself on a Pacific island far from everybody to help me say no to everything. So I knew that I wanted to create an environment where people wouldn’t be inviting me to things anymore. Because, “He’s in New Zealand. He’s gone.” And sure enough, I’m glad I don’t have the FOMO thing much because yeah really some dear, very well connected, successful friends stopped calling when I moved to New Zealand because I used to be in the game, and suddenly I wasn’t in the game. I had dropped out and moved to a Pacific island and had a newborn, and they stopped calling and stopped inviting me to events. Yeah, and I had to be totally okay with that. But I created the environment that I knew would work for me. So we can do that with our own homes, with where you keep your phone. I mean, can you imagine if, like, how by the front door, how sometimes there’s like a little bucket where you drop your keys. Could you imagine if we just dropped our phone there? Like no, a mobile phone is something you need when you’re not home. And just like that’s it. And in the home, we don’t have phones. You know, like some people leave their shoes at the door. It could be like we leave our phones at the door.
Tina
Should definitely do that more.
Derek Sivers
But it’s like you could choose to do that if you knew that that’s the environment you needed to fit your value system. Yeah, because some people don’t value that. They say, “No, no, it’s important to me that I’m connected and available to my team all the time.” But, you know, I mean, some people that works for them, you know, and I forgot to finish the people with the Rolex watch. It doesn’t work for me, but for some of them, it works for them. You know, they might have even asked those philosophical questions about like, what is it for? And and they like, well, to me--
Tina
Maybe it can improve their perception of self, which then gets them to perform.
Derek Sivers
Right. Or they could say, “Whenever I was a kid, I dreamed that someday I would look like this. And now I’m being my highest self, wearing the best watch. That’s a piece of art and and it reminds me to be my best.” Whatever. You know, if that works for you. I must say, when.
Tina
I must say when my last company got towards its end in the last couple of years, I got a BMW like a fancy, sexy car. And I did love it. And then I wondered what that meant about me, that I loved it so much and I’d walk up to her and go, damn, it’s a sexy car. And I loved driving it, would never buy one again. Don’t need it in my life. But it was fun. So I kind of get it. Kind of get it. What does a meaningful life look like to you?
Derek Sivers
I don’t think in those terms at all. I just do whatever is interesting me most right now.
Tina
Really?
Derek Sivers
I think to say meaningful is to ascribe a plot. And again, for some people feeling like their life is an epic tale that has great meaning and started here and is currently here. But it’s going there and it’s going to circle around. For some people that story helps guide their actions and means a lot to them. And I’ve considered it. But no, for me, I’ve just found what drives me best is to follow whatever interests me most. And I don’t think of it.
Tina
So that next little bit.
Derek Sivers
Yeah, I don’t think of it in terms of meaning at all.
Tina
That’s so interesting. Yeah, a lot of these questions I’m not asking for a friend also they’re for me. But that’s a big one that I have the Anthony Robbins days I always had like life plan, life purpose, ten year plan, broken into five year plans, broken into one year plans, broken into 90 day action steps, weekly KPIs, and then daily tasks like ninja level planning. So it’s no wonder that I hit like the wall right with that. But since I’ve let that go. Like the reason I wanted to ask that question was I have gone well in the absence of that. Like, do we really just go, “All right, what’s next?” And just do the next thing? Like it feels almost free fully without having that plan in place.
Derek Sivers
Want to hear a big idea?
Tina
Yeah.
Derek Sivers
I haven’t dove into this yet. Long term plans are who you were. Today’s plans are who you are.
Tina
100%.
Derek Sivers
Isn’t that badass? Yeah, I didn’t come up with that. I just heard a version of that today, and I’ve just been thinking about that. Like that’s right. Long term plans are usually what you thought before and then today’s reality can be different. So if you follow today’s reality 100%. So even in a business even like we’re making our long term plans for a business. Okay, but our clients are asking for this today or things have happened in such and such in this way. And this is what our business needs today. Really, business should be short term focused because it keeps it more like practical and really attuned to the current reality of your clients.
Tina
Yeah, this is very true. So the other day I was cleaning out a cupboard, as you do, and found I wrote this book, like 101 dreams book that I had that was like a stationery thing that had it all written out. And I had the 101 goals. So talking about, like, your plans are who you are then, not who you want to be in the future. And there was a ton that I have achieved and a ton that I have no interest in achieving anymore. And it was a really nice. I filled it in, probably I hadn’t given birth yet, so I was 22 maybe and I was looking at that and going like the chapters, everything that I wanted then is so different to what I want now. Like one of them was, you know, I wanted five investment properties and I wanted to be worth $10 million. And I had like, all of these set things that were so important at that time of what I thought we needed to have. And I was really looking at that and going, “How much the chapters of life that we lead.” And that was really written from the point of view of, you know, I was newly married, didn’t have any kids. The whole life was stretching before me. I was a new adult. And then looking at the chapter where I had babies. And that was a very different, limiting sort of existence there. And now I have man children, which is wild to me. And then soon they’re going to be gone. And like and it’s only now I’ve started thinking, “Well, what next?” Like life as I know it is not going to exist anymore. Do you you live in in a chapter sort of way? Because, I mean, you’re in New Zealand right now too.
Derek Sivers
Yeah, just I mean, you nailed it. Same as you just said. Yeah, it’s definitely there’s these eras in your life.
Tina
Yeah. Do you know what the chapter will be once your son grows up and moves out?
Derek Sivers
Yeah. Despite what I just said about long term plans. I make hundreds. I’m sitting there in my--
Tina
Isn’t that fun though? Having so many different realities and going, “We could do this, we could do that. We could be this, we could be that.” And then be like, “I want to be it all.”
Derek Sivers
Yeah, yeah, it is. I don’t know if you’ve done this. I used to dive into one at a time, I’d be like, “Oh my God, I know what I want to do.” Yeah, I’ll just make up one. I’ll sail around the world. And I’ll just get in and let’s just say, imagine like I dive down the rabbit hole and this kind of boat and this and the planet. You start to this, and then do this. And I might even go tell friends. “Guess what? I’ve decided that this is what I’m going to do.” And then say, like it’s two months later and you’re like, “I want to have investment properties.” Something that conflicts with sailing around the world, right. And then that sailing around the world idea kind of fades and you go into the new you know, “I’m going to be a dog trainer.” See that would conflict with sailing around the world and be a dog trainer. And then you kind of feel bad, like, “Oh, I’m an idiot. I changed my mind too much.” So my solution is I made a folder on my computer called “Possible Futures”.
Derek Sivers
And now every time I have one of those, I fully realize like, I open a new text file and in the possible futures folder, “I’ll make sailing around the world”. And in that file, I will dump all of my plans, my detailed sketches exactly. You know what boat I’m going to buy, by the way it actually helps me that I’m sailing around the world has never been one of my actual ones. It helps me to detach. Like if I were to talk about what I really wanted to do, I wouldn’t be able to talk with such detachment. But then, in that moment it feels like, “Oh my God, I’m going to do this.” But yet just the fact that it’s in a possible futures folder helps me either dive in or detach guilt free. Because it’s like, “All right, this might happen.” Because now there’s like 120 things in there. And then when I get to a certain point in life when, say, like I finish a project, I finish a book, I wrap something up, then I’m like, so what next? I’m like, “All right, possible futures.” And I’ll open the folder and I’ll,
Tina
What is one that’s in there that’s really exciting.
Derek Sivers
I mean, top my head right now, would be to move to either Bangalore or Dubai.
Tina
Wow. Two very different places.
Derek Sivers
For two different reasons. I already have a lot of friends in Bangalore, and I just went to Dubai for my first time last year, and I’m currently fascinated with it. Yeah, it is the bar in Star Wars.
Derek Sivers
Yeah.
Tina
Star Wars?
Tina
And it couldn’t be more far removed from where you currently live. Is that the purpose? Let’s just go crazy here and go from one extreme to another. I mean, it’s like--
Derek Sivers
Right? New Zealand.
Tina
Yachts and the bougie--
Derek Sivers
Oh, no no no. Okay. No, you’re you’re talking about, okay. Just like the state of Nevada has the Las Vegas Strip and but then there’s also--
Tina
Okay. That’s the only Dubai I’ve seen.
Derek Sivers
Have you been?
Tina
Yes.
Tina
Okay.
Tina
I’ve only seen the bougie.
Derek Sivers
Okay I will not look that direction. The only Dubai I’m interested in--. Okay my good friend there, his grandfather built the first building in Dubai ever. He’s an Emirati guy that his great grandfather came up with that original tribe. Like 150 years ago from Abu Dhabi because they were having clashes between the Bedu tribes. And they came up there to this little fishing village. It was like, you know, huts and decided to make it their new place. And he’s been teaching me about Emirati cultures and traditions. And I was like, “That’s the side I’m interested in.” And I think it’s interesting that, you know, I’ll stick with the bar in Star Wars metaphor, that these strange creatures from around the galaxy come to Dubai and you’ll have the Nigerians with their green robes and then the Russians with their bellies hanging out, and then the sunburned Brits and then the Indians and the Pakistanis all together in one place. I guess, to conduct some trade and then get on their spaceship, you know, back to somewhere else. And I just find it so culturally fascinating to talk with everybody there. So one of the best days of my life was at the Dubai Mall, sitting at the second level, where there’s an escalator going up to the second level and escalator to the third level. And I sat in a little tea shop there at the second level and just like sat there for hours just watching these people in their different garb and their traditional robes and all that, like just going by just like, oh my God. And for every Muslim woman that was like completely covered where you can just see her eyes. And then the next one comes by with, like, boobs out to here with the lips, and they’re like, the horrifying plastic surgery. And I was like, “This is fascinating.”
Tina
But to live there?
Derek Sivers
Just because of that, like, I would let people know that I lived there, and I would try to meet all the people passing through. So that’s what I did in Singapore for two and a half years. I was very public, like, “I live in Singapore now.” And I got to meet everybody that was passing through Singapore. Even like the the founder of stripe was passing through Singapore. I was the only person he knew in Singapore at that time. So like I spent the afternoon with Patrick Collison and then Kevin Kelly, one of my heroes, was passing through. I was the only person he knew in Singapore, so I got to spend the day with Kevin Kelly. I spent his 60th birthday with him. So that’s the.
Tina
So that’s the strategy. Just position yourself at like a layover space.
Derek Sivers
Yes, you get to meet so many people. And then but just the mix of cultures, like when you’re in Dubai, you can just literally turn to anybody and say, “Where are you from?” And it’s like, “I’m from Cameroon.”
Tina
Yeah it’s a different story.
Derek Sivers
It’s amazing. Yeah. So anyway, sorry, that’s one of my possible futures. I might not do it, but yeah, I mean, it’s still six years until my boy is done with school in New Zealand. So see how I feel in six years.
Tina
It goes very fast. It’s not very far away.
Derek Sivers
I’ll keep that in possible futures. I don’t know if did answer your question you asked about? What was the actual question?
Tina
The question was meaningful life.
Derek Sivers
Oh,
Tina
That’s how we got there. Yeah. Which was really good. In what to do next with chapters. That’s what we were looking at.
Derek Sivers
Chapters, right. Yeah, I would highly recommend that. There are very few things that I will say, everybody, you should do this. Yeah. I think keeping a possible futures folder.
Tina
I love that idea.
Derek Sivers
I think everybody should do that. Let yourself dive in. I have too.
Tina
I have too many that I want to do.
Derek Sivers
But that’s okay. But that’s what I mean. It is the solution to having too many. To keep them all in a place and then actually like let’s say I’ll just pick another, you know, the dog trainer and say like three years ago, you thought it would be a great idea to be a dog trainer, and then suddenly in 2024, you’re just like, now you get to go back to that file, add on to it some more, add to what you’ve learned. And then maybe you leave it and suddenly in 2027 you’re just like, you know, “Now that we’re living off in this rural space, I’m going to do it. I’ve been thinking about this for years. This idea won’t go away. I really want to be a dog trainer now.” And now you can refer to years of notes on it. And the other 112 things that you’re not doing you can feel okay about. This is the one for now.
Tina
So I was talking to my coach the other day and he’s wonderful. And he was telling me though I struggle with this not taking it slow, but going too fast all the time. He’s like, “You’ve got to look at your time just even in a weekly view.” Not even in how many possible futures you want, but even just like in a micro level and only do the things that you value the most. And I’m like, “I value all of it. I love all of it. There’s none of it I want to say no to.” And you’re super into stuff too. Like you get really excited about what you’re doing, which I love. I am overly enthusiastic about all the things that I’m doing. So when I look at my schedule and look at what I want to say yes to, there’s usually too much in there for like the actual logistical time and energy available. So when you want to do more things and to talk with more people and to get into life, how do you discern when enough is enough?
Derek Sivers
I’m not sure if I’m understanding the question correctly. Again, the possible futures thing is, that was my way of managing the idea of wanting to do too much. Yeah, it’s like bye bye, knowing that I’ve saved all my thoughts about it--
Tina
So then you can park it there, and then you’re like--
Derek Sivers
Park. Good metaphor. It’s parked there, I can go, I’ve got the keys to that car. Yeah, I can go pick it up any time. It helps me get peace and closure to say, “All right, I’m going to come back to that.” It’s not that it’s gone. So it’s not like choosing one thing doesn’t mean that the rest will never happen. It’s just, “I need to do this one now to completion. I’ll come back to that one later.” Somehow that gives me peace of mind to throw myself into one. Because I’m just choosing it for now. Yeah. Because it’s for now I want to I want to do things to completion, right. Like when I have an idea for a book, I’m like, head down. I’m just doing this and it’s like, oh, Tina, there’s so many other things I’d like to be doing right now, but I’m like, I just have to finish. I’m like typing. I don’t actually type like that.
Tina
It’d take a while.
Derek Sivers
It’s cute. I feel like Linus at the piano, you know? I’ll just throw myself into one thing knowing like, okay, this is for now, and I want to finish it, and then I’ll lift my head up, look at the other things and pick another one.
Tina
Okay, so that’s with time. With things, the minimalist thing I have to ask you about the minimalist thing. Do you really only have like two cups and like a few outfits of clothes? You do like actually. And you never go, “I wish I had more variety.”
Derek Sivers
How many times have you moved house?
Tina
Many.
Derek Sivers
Really?
Tina
Yeah, we moved 11 times in 17 years, and now we’ve been in the one place for three years, and we won’t move until our kids are done.
Derek Sivers
Okay. But despite that, I mean, each time you pack up all your stuff and you don’t resent it?
Tina
Well, I don’t, and this is--. So, you know, I had a really interesting thing. We redid our wills or our estate planning and everything, like a couple months ago, and one of my best mates is moving house, and he moved and left everything, sold all his furniture and just moved into the new house with like, a suitcase and no moving trucks, no nothing. Anyway, the moment that I had when we were estate planning was I was going through and I was looking around my office, just my office, for example. There are beautiful trinkets everywhere. It is like from my travels, I’ll usually buy one thing that means something to me, and I put it there and I love it. And I’m looking around and going, “So when I die, what will happen to all of this?” And so I asked my kids. I was like, “Is there anything here that you would want?” And they both said one thing, neither of which was the thing that I would have ever thought that they cared about. And I’m like, “What would you do with the rest?” And they’re like, “Oh, give it away to someone that would like it, I guess, maybe take it to the nursing home.” And I was like, all of these treasures that I have collected mean nothing. But then I was looking at it going, “No, I still love my things, love my things.” So I’m intrigued.
Derek Sivers
It’s proven to have a powerful effect on your mind to have certain things around that even in like academic situations, they did like very subtle, like almost subliminal things around the room then. Asked people a question there and their answers were predictable based on the subtle things. Like they would hide like subtle little dollar signs done in an ambiguous way, and then ask them questions. Their answers were more selfish than if they had showed photos of like nature or whatever. Then their answers were more like--. And so the stuff that’s around us affects how we think. And so that can be a beautiful reason to have these trinkets that mean a lot to you, because it’s like helping you.
Tina
And you don’t have that?
Derek Sivers
I don’t know. But sometimes I think I should. Like, oh, okay I hear it’s good for me to have trinkets around or even, I went to a--.
Tina
So sentimentality is, like, not a thing?
Derek Sivers
It’s mental, not physical. I’m very sentimental with many thoughts and people and all that, but, like the physical stuff, I just moved house so many times, I just, just.
Tina
Yeah. Let’s get a bigger truck.
Derek Sivers
Well, no, every time I move, I do it like your friend. I always bring nothing with me. Oh, I was in a hotel once that recently had a the big bookshelf with like 200 books on the wall. And I went, “Oh God, that’s nice.” Like, right now I just do ebooks. I have no---
Tina
You have no books?
Derek Sivers
I don’t have any books.
Tina
You have no books even?
Derek Sivers
No.
Tina
Derek. Yeah, wow.
Derek Sivers
So I actually thought of, like, maybe going to a used bookstore and like, or basically presenting a list of my favorite 200 books to a used bookstore and just saying. Here, if you find these, I’ll buy them from you. But I would only do it as visual props because I’ve already read the book. I already have my notes, so I would do them as the visual props, like somebody putting pictures of nature around them to, you know.
Tina
Wow, I have that in my office, like books, and they’re color coded in a rainbow.
Derek Sivers
All right.
Tina
You’re not surprised,
Derek Sivers
You nerd.
Derek Sivers
Yeah. But I will go back like I have the notes from your books, for example. But I will go back and I will read it again. The whole book.
Derek Sivers
Okay.
Tina
Because I don’t just want the cliff notes. Sometimes I want. And what I find is there’s another book that I just read that I hadn’t read in ages, “One Minute Millionaire” by Mark Victor Hansen. Love that book, but I read it and I haven’t read it for ages. And when I read it, it like means something different or I pick different things up that I wouldn’t have read and took note of before.
Derek Sivers
I have reread like 3 or 4 of my favorite books ever. It was weird rereading “Awaken The Giant Within” last year.
Tina
I might do that too.
Derek Sivers
Oh, it’s so dated. It’s so weird. I read it in 1989 or 90 when it first came out. It’s referencing OJ Simpson as a role model. Michael Jackson, all these like 80s business role models, like the old president of Chrysler or something like that. I’m like, wow, these references, like nobody under 50 would know who these people are anymore. But there’s such a good message in the book. I feel like his team should rewrite it for him. Strip out all the old references. Yes.
Tina
Yes. Okay, I’ll try and stay on track here. So “Useful Not True” it’s coming out soon, which is yay!
Derek Sivers
I’m still writing it.
Tina
Do you know when it will be released? Oh, there’s no date, so you can’t say. And you self publish too, right?
Derek Sivers
Yeah.
Tina
Because you like the control over distribution or why do you go self publish? That was one of my questions but I’m curious.
Derek Sivers
Is it, are you self published?
Tina
I did my first book self published because I couldn’t get a publisher because I was a no one. But then I did my second one published, and there’s for and against for both of them that I found, like I was mentioning that my first book is the one that you can see the screen of, not the other one, because that’s the cover I designed my second book, “Million Dollar Micro Business”, the publisher designed, and it’s cream. And I don’t like cream. Yeah.
Derek Sivers
Right. Yeah, it feels weird to like something--.
Tina
It has brown writing. And I’m like, really?
Tina
And it’s about like, online business. And the icon on the front is a mouse with a cord. Anyway, so that’s why I didn’t love the publisher. But next time I will get a deal to say that I have creative control.
Derek Sivers
Yeah. I just found that. I mean, you know, my little nerdy reasons don’t matter. You know, I built cdbaby.com. It’s like I can build a little store.
Tina
Distribution wise, do you put it in all major bookstores or you mainly sell online?
Derek Sivers
Actually for the first year or so, it’s only on my sivers.com website. I don’t even put it in Amazon.
Tina
Really?
Derek Sivers
Yep. I’m like, no, screw Amazon. Yeah, I don’t need to give Jeff any more money.
Tina
That’s because you’re famous. You can.
Derek Sivers
Right. But I mean, we all can. I mean okay. It’s easy to dismiss it and say like, okay, but that’s because you’re famous. But no, even me deciding to do that, I’m sure I’m cutting my sales in half by doing it, but it makes me happier. I’ve just noticed I am happier selling half as many books, but entirely through my store. I mean, hell, even if it’s a 10th, maybe I could sell ten times more books if I put it on Amazon from day one and did the whole thing people do, like, “Hey, let’s get the lead up to the first week of sales so I can be on the charts so people can discover it.” I’m letting go of all of that. I will not be number one ever. And it’s okay because it makes me happier to do it this way.
Tina
What is your number one goal when you put the book out?
Derek Sivers
To be done with it. Yeah, yeah, that’s another one. Okay. What’s number two?
Tina
What is the number one goal when you write a book?
Derek Sivers
Oh, it’s different every time. All right. Well, okay, so check this out, “Your Music and People” I actually wrote first, and that was written from 1999 to 2005. It was my ongoing advice to musicians, like when musicians would say something like, “Hey, how should I price my music?” And I’d write something to address that. And then musicians would say--, I don’t know. Let’s just say whatever questions would come up. I’d write an article addressing that it in a way that wasn’t timely, but more like philosophical. And then later I put all of those together. I think there were like 88 of them or something like that into a book called Your Music and People. That was just collecting something I’ve already done. Then Seth Godin called and said, “I’m starting a new publishing company, and I want you to be my first author.” And what can you say to that? But okay. So, “Anything You Want” was written in 11 days because Seth asked me to.
Tina
You wrote that in 11 days?
Derek Sivers
Because those are stories I had already been telling to friends and at conferences. I’d been on stage. Some of them were already written on my blog. About half of them were already were. The other half had just been telling anecdotally at dinners and whatnot. And so when Seth said, put it into a book, I’m like, oh, all right. It’s just telling my story. That’s easy. So there was no self-discovery or learning in the writing of that book. It was just telling my story of what’s happened in the past and the lessons I learned from it. Hell Yeah or No” was a--.
Tina
Crazy book. Oh no, this one. “How to Live” the crazy book.
Derek Sivers
Oh, no sorry. We’re talking “Hell Yeah or No” was again, just collecting up, people had been asking my advice about, general kind of how do I make decisions in life. So again, I just collected together articles I’d already written and I just wanted to put it into one, like, there we go, it’s done. Okay. So then “How to Live” it’s more of an art piece. Did you read “Sum” by David Eagleman?
Tina
No.
Derek Sivers
No. Okay. So it helps to know on the first page of the book it says, “This is an homage to Sum by David Eagleman.” So David Eagleman is a neuroscientist that wrote a beautiful little fiction book with a weird format. That’s called Sum, spelled s-u-m. And the subtitle is “40 Tales from the afterlives.” And it’s 40 little 2 to 3 page long short stories that say what happens when you die and each one disagrees with the rest. So it’s like, “When you die you awaken to find out that in the last life you chose to be a human, but you could have chosen any animal. And now it’s your turn to choose again, to choose to be any animal you want. So you decide to be a horse.”
Derek Sivers
And then it’s a fascinating little story. But then the next chapter, it’ll say, “When you die, you find out that you are an artificial intelligence program that what you knew of as your life was actually the running of a program that is you. And now the program has ceased running. And the little caveman type creatures that created you want to know the meaning of life. But everything you try to explain to them, they’re too dumb to understand.” Then the next chapter will be like, “When you die, you’re in a giant mansion that is uninhabited, and you walk around for days and days like there’s nobody there until you finally find somebody else and you say, ‘Excuse me, what’s going on?’ And they said, ‘Oh, well, turns out that God is a creator, not a manager. He created life billions of years ago and forgot we exist and everybody’s waiting for him to come back. But he’s not a manager. He’s not here.’”
Tina
So that inspired you to write?
Derek Sivers
So yes. So this format of like, oh my God, I love this. Like every chapter disagrees with every other chapter. What a fun way to spin your head around and what a beautiful format. Because it’s also like-- there’s a piece of artwork in Wellington, New Zealand, where I live. Right downtown, across from the New World supermarket, where there are like 100 sharks drawn by 100 different artists on a giant mural. And so every shark is completely different, like a different artistic rendering of a shark. But they gave them a certain like it has to be maybe one meter by a half meter, and it has to be facing left, go. And I just love that format of like, having 40 different artists give the same challenge. So to me the book “Sum” was like 40 different answers to one question, “What happens when you die?” I love that book so much. I read it twice and one day I was like driving down the highway in South Island, New Zealand and I went, “Oh my God, I want to write a book called How to Live in that format. Oh, my God, this is brilliant.’ I was like, “And then every chapter is going to disagree with every chapter. Every chapter is going to say that it has the answer on how to live. And it’s going to disagree with all the other chapters.” It’s like, and I just started, you know, just typing furiously.
Tina
Isn’t that the best feeling ever?
Derek Sivers
Love it when you get.
Tina
When you get that feeling that “This is what I’m going to do.”
Derek Sivers
But then it ended up being this, like, I want to put everything I’ve ever learned in my life into this book. And so I like, reviewed every all of my notes from every book I’ve ever read, all of my diaries, everything I ever wanted my kid to know in case I die before he’s older. I poured everything into the book, and the rough draft was 1300 pages, and then I spent two years editing it down to 112 pages because I like short books.
Tina
Yeah. So incredible that you wrote the others so fast. But then that one, did you care more about that one or was that-- yeah.
Derek Sivers
Yeah, because it’s more like poetry.
Tina
It was such mind fuckery to read it.
Tina
It was-- because I was telling you this before we hit record. But the others I read like like reading them, not guru esque, but like that “Yes, you tell me, Derek, I’m ready, I’m ready.” And I was highlighting and I was like “Yes, I agree, this is amazing.” And then I had that when I got that book out and I read it and I’d read some and I’d go, “This is fantastic.” And then I’d read some and I’d go, “Oh, I think we’ve taken a bit of a left turn here. This sounds a little bit different. I’m not quite sure on this one.” And then you read it and then it would completely disagree with that. And I’m like, “Oh, I see what you’re doing here.” But it was really good to see it. I have never read a short book so slow as that book. When I read each chapter and then sat there going, just staring off into space like.
Derek Sivers
Thank you.
Derek Sivers
Good, good.
Tina
Huh? What do I actually think? And do I agree or do I disagree? And what? And it was beautiful for that.
Derek Sivers
Thank you. What did you take from the the last two pages with the two images?
Tina
Oh I can’t remember the last two pages.
Derek Sivers
So to me it was the punchline. So that’s what I was also stuck with for like two years.
Tina
Now I feel awful that I’m like, what? I don’t know, the last two pages.
Derek Sivers
How do I finish a book of this format?
Tina
Oh yeah, the orchestra.
Derek Sivers
The orchestra. So to me, the orchestra.
Tina
So that is like I’m going to put a picture of that in the notes below so that, so that you can see it. But I was like, that went right over my head. I was like, I don’t think I’m--, I’m not smart enough to get that.
Derek Sivers
It’s okay. So to me like the most beautiful---
Tina
You’ll have to explain it.
Derek Sivers
Yeah I’m about to. So to me the most beautiful movies are the ones that when it’s done, you kind of go, “Huh?” And it sits with you because you’re like, “Wait, so does that, did he die or not die? Wait, what does that mean?” And I like when you kind of walk out of a movie with a question. And ideally a book could do that to you too. But the thing is unfortunately no non-fiction books do that these days. They’re all just like, “Well, here’s the answer cut and dry. Here’s the seven step program, and that’s what you should be doing. I know everything now. You know, go get em there.” You know, it’s like there’s no artistry to it. It’s just like fucking business. And I was like, I don’t want to write fiction, but like---
Tina
You want it to be a bit whimsical?
Derek Sivers
Yeah. Or like, like song lyrics that when you read like the Leonard Cohen song lyrics. It makes you go like, “Huh? I wonder, what do you mean? That’s an interesting metaphor. Why that? The tortured King. What does that referring to?” I miss that artistry. So it was actually a songwriter friend of mine that gave me a little encouragement to do this when I said, “What if I just left it open?” And she’s like, you know. Okay, so the whole point of the duck and bunny.
Tina
Yeah. It’s both, right?
Derek Sivers
The question that the optical illusion asks you is, “Is this a duck or a bunny?” And you’re supposed to kind of like either pick or you’re like, “Oh, well, at first I saw the bunny, but now I see the duck.” But then to me, I looked at this for a while and I was like, “Wait a minute, it’s not or you don’t switch from duck to bunny. It is a picture of a duck and a bunny, both at the same time.” I was like, “That’s like how to live.” We don’t say---
Tina
Okay. I did get it then.
Derek Sivers
Okay. It’s like we don’t say---
Tina
I think it meant more than what I--. But yeah.
Derek Sivers
We don’t say is selfishness good or is it bad? It’s like, well yes depends in some situations and this and that. Should I be following my dreams or should I put my dreams on hold to serve others? Yes, both. In different times in your life, different situations. So the orchestra seating chart is the metaphor for the different times because music is time and combining. So if you were to ask an orchestra conductor or a composer what is the best instrument in the orchestra, it’s a moot question. What do you mean the best instrument? It’s sometimes I need the violas, sometimes I want the timpani. Sometimes I need all the brass. Sometimes I’m going to combine the piano and the cellos. So there are 27 instruments here, 27---
Tina
So glad that I’ve got you to explain that because I didn’t get any of that from that. So that’s so good
Derek Sivers
So it’s like there are times in your life when you need your trumpets to be playing. You know there are times in your life where you need to go get famous and and try to get success. There are times in your life when you need to mute everything and go to the slow, steady pulse of a predictable, comfortable life. There are times when you want the entire orchestra to play at once, and sometimes it can even just be in the course of a day. You can wake up and have a very selfish hour to yourself before the rest of the family.
Tina
I had a very selfish day yesterday. I loved every second of it.
Derek Sivers
Oh that’s right, you indulged here in Noosa.
Tina
It was so good. I had a day of nothing in Noosa and I’m like, I should do that more often. Okay, going to go over to money.
Derek Sivers
Oh wait, there’s one last, sorry, I accidentally nerded out on my books themselves, but you asked what are my goals when I’m trying to write. I was really trying to say in the big picture that every book has had a different goal. And so my next book, “Useful Not True”, I didn’t start out knowing what I wanted to say already. I said, “I want to learn more about this subject.” So I’ve spent the last two years learning more about the subject. So the purpose of writing this book has been for my own self.
Tina
How long have you been writing this book?
Derek Sivers
For two years. Two and a half.
Tina
Oh yeah, a long time. Yeah. And so staying on “Useful Not True” for a second because I do think it is intriguing, and I think it will be another similar to that in that it will mess with our minds a little bit. What is the belief that you have had that you challenged or changed through the process of writing it? Was there one?
Derek Sivers
Oh, always. I mean, ideally my dream life would be to have a belief changed and challenged daily or weekly. Okay, let’s just pick- because we mentioned it earlier, Dubai. If you would have asked me a year ago today, Dubai would have been in my top ten shit list of places I hoped to never go in my life. Fuck that place. Shallow. Would you call it the glitz? Bougie? The bougie glitz, hashtag Instagram influencer bullshit. Millionaire pandering. Fuck that. And then I had an airplane layover. And instead of just, you know, two hours, I decided to make it two days. Then I read two books about United Arab Emirates, and then one book that was fascinating about the history of Dubai itself, called “City of Gold”. It was really well written and like it’s like a page turner had me up all night. I was like, “Oh my God, this place is fascinating.” Then I went there, then I met this Emirati guy that was teaching me more about the Arab culture. Got me to go to the Al Shindagha Cultural Museum, where I went to the perfume house, and that, like, changed my life. And---
Tina
Did you buy a perfume?
Derek Sivers
Perfume has different meaning there. Homes are perfume. Every home has a unique scent, and it’s a big part of the character. And then when you have guests over, whether it’s for hours or days when you’re ready for them to leave, you put on a different scent, which subtly kind of says, like, it’s time to go. It’s kind of the equivalent of--. So and since I read like three more books about Arab culture and I took something that I was prejudiced against a year ago and am now straight up prejudiced in favour of. And that’s one of my favourite things. We take something that used to know nothing about, or used to even be against, and you suddenly are---
Tina
The world would be a much better place if more people did that, I think.
Derek Sivers
Yeah. Once again, something we can wholeheartedly prescribe to everybody should do that. You should all, not do my a particular bit. Like we should all steer towards the things that we feel an aversion towards. If you hate opera, you should get to know opera better. If you hate sports, you should get to know sports better. Yeah. Go drive into your blind spots.
Tina
Yeah. I mean, I have a pretty much in Spotify. Had my same Spotify wrapped every year for the last three years. Same songs, same things. Very boring. Same with like, you’re like, movies should end open ended. I watch hallmark romantic comedies. I don’t know what that says about me. But I love them.
Derek Sivers
Time to switch it up. Make yourself-- did you see Poor Things yet?
Tina
No. Oh, that’s Emma Stone’s movie. Yeah.
Derek Sivers
It’s one of my favorite movies in years.
Tina
Okay, I’ll have to watch it.
Derek Sivers
It takes repeated watchings to like, especially if you can rent it. Yeah, it’s the first time you see it, it’s like, whoa, what the--. And then you watch it again. It starts to make more sense. See, I love these things.
Tina
See, my youngest son is into jazz and the distinguishment between like, New York jazz and New Orleans jazz. And so he’s been making these playlists. And now I’m listening to all of his music and love it. And would have thought never. Anyway, so little things that can work as well. Question with “Useful Not True” and my favorite interview I think I listened to of yours was the one you did with Mark Manson. It was great. But with and reading a lot of the chapters that you’ve published on your blog as well, do you ever get tired of thinking about thinking?
Derek Sivers
No, no, no.
Tina
You never, like, wish you could just shut it off and go, enough of the examining. You just want to just chill ignorantly.
Derek Sivers
No, it’s just my favorite thing. Yeah, I just love thinking of different perspectives. Yeah. It’s one of my greatest joys in life.
Tina
And it never switches off in your brain?
Derek Sivers
No. Not really.
Tina
And that doesn’t get exhausting?
Derek Sivers
No, because it’s just my favorite thing, you know, it’s like. Yeah, it’s the thing I love most in life is thinking.
Tina
That’s interesting. Yeah, I’ve been doing a lot of work on it in the last few years, but one thing that I said to my coach is, “Some days I just want to stop thinking about thinking.” I’m now thinking so much about thinking and what I’m thinking and questioning what I’m thinking that I’m like, “Oh my gosh, enough.”
Derek Sivers
I mean, okay, look, every week I reliably spend 30 hours a week, one on one with me and my kid. And when I’m with him my own ambitions are on pause, parked. And he leads the way and I just follow. And if he wants to go surfing, then we’re going surfing. If he wants to play in the forest, we play in the forest. He last week decided he wanted to learn to sew. We started sewing last week. So in a way that kind of turns off my brain because I’m just there, fully engaged in whatever he’s doing. Yeah. That’s good.
Tina
Yeah, that’s good. When you think of successful, who’s the first person that comes to your mind?
Derek Sivers
Me.
Tina
Smug.
Derek Sivers
No, I mean sorry, that’s just ridiculously honest. I’m not saying I’m the epitome of success, but aren’t we all thinking of ourselves first with almost anything in life, you know?
Tina
No, I don’t think we are.
Derek Sivers
Okay, but if you say something like, “Who’s the first person that comes to mind when you think of watches.” Then wouldn’t you just going to think kind of consciously, your brain is thinking, “Well, my watch.” Because you’re thinking everything’s kind of filtered through my desires. So my honest answer with that is like, well, I think of myself first because I think, “Wait, successful compared to what or who? What is my definition of success? Oops. I’m thinking about me now.” So my brain didn’t just jump immediately to Richard Branson or something. My brain thought of myself first and then it’s like, well, wait what is my definition of success? And then there’s the answer to your question. I thought of myself first.
Tina
What is your definition of success?
Derek Sivers
Just achieving what you set out to achieve. That’s it. Yeah. If you set out to to write a great poem or bake a great cookie. And you did it, then that’s the success. That’s it.
Tina
I love that. Is there--- so probably not because you’ve got a different definition of success. But was there like a point that you felt like you made it, like you are living and you did achieve what you set out to achieve?
Derek Sivers
Ooh. Probably when CD Baby got momentum, meaning when it was clear that people really liked this thing because it was the first time in my life that I felt I was rolling downhill instead of uphill. And I mean that like as far as leads. Like all my years trying to be a musician. I mean, I was a musician trying to be a successful musician, it just felt like every door I tried to open was locked.
Tina
And in Australia, we say pushing shit uphill.
Derek Sivers
There you go. Yeah, I was just about to say. Yeah, it just felt like everything was uphill. Yeah, I was pushing shit uphill for years. And then at the age of, what, 28/29. Yeah, I started CD Baby when I was 28 or so and then just like people just started signing up for it and then more and more and then people telling their friends and suddenly everybody was like, banging down my door to do this thing that I did in three days as a hobby. And so I guess it took two weeks to set it up. But that was the first time I felt like maybe once that kept going past two weeks, and then it was like three months into it and people keep coming my way. I was like, “Well, it’s a fresh start. Well, I’ve really made something people love.”
Tina
And from that point on you’re like, “I’m my own version of success.”
Derek Sivers
Oh, I’m my own version of success. Yeah.
Tina
I love that.
Derek Sivers
Yeah, I guess a lot of my actions have been filtered through that. I mean, I’m being stupidly honest here. I know, like, I’m saying things that we’re not supposed to say.
Tina
You’re not? Why aren’t we supposed to say that?
Derek Sivers
You know, even when I heard myself say that thing earlier about, like, “Well, social media was invented after I was successful.” It’s like, fuck, that’s honest. But I guess that’s true. I mean, it’s a reality. I’d be doing some weird lie if I said otherwise.
Tina
I love that,
Derek Sivers
So I guess since then it’s like, well, I’ve got my own version of success that I know people are happy with. You know, ten years of running the company. I knew my clients were really happy. The fact that I didn’t drive a fancy car or have a fancy watch was a good thing. Maybe I even added to my brand or whatever, even though I didn’t think of it that way. But maybe people saw that. It just---
Tina
“May have added to my brand.”
Derek Sivers
You know what I mean? Like, I used to - I haven’t done it in years, but for most of my years at CD Baby, I had a really funky haircut. I had really long dreads in back.
Tina
I have not seen that picture
Derek Sivers
For 14 years. Yeah, there aren’t many pictures of it online, but there are a couple I had.
Tina
It’s because you don’t have pictures on your website.
Derek Sivers
No.
Tina
Why?
Derek Sivers
I don’t know, I’m not much, I don’t have pictures of my phone either.
Tina
What?
Derek Sivers
Yeah, I don’t take pictures. I’m just not into it.
Derek Sivers
Yeah. No.
Tina
Really?
Tina
I think I have maybe half a million pictures on my phone.
Derek Sivers
I’m sorry to hear that.
Tina
No, I love - so do you know, my kids were asking me about this the other day because they’re like, “Mom, always with the photos.” I picture my old age sitting in a really comfy chair, just reliving my life, watching my photos. I don’t have a great memory. And I love photos, I love them, I will watch, like every plane flight I go on. I sit there and I flick back through there, like through life. And I love it.
Derek Sivers
See, I do that with my diary. I’ve kept a diary every day.
Tina
You ever afraid of someone finding it and reading it?
Derek Sivers
No. It’s like super encrypted on my encrypted hard drive. And, you know.
Tina
Of course it is. Yeah. Okay.
Derek Sivers
So, it’s not---
Tina
You don’t like write it. You type it.
Derek Sivers
Yeah. It’s typed.
Tina
Lock it away.
Derek Sivers
Locked inside a OpenBSD.
Tina
What about when you die? Will it be made available or it’s going forever.
Derek Sivers
Maybe just my son. I would let him have it. You know.
Tina
You don’t write naughty stuff in there?
Derek Sivers
Even if I did, he’ll be old enough by then, hopefully. But I relive my past through my diaries. It’s really interesting to see my inner dialogue. Monologue, dialogue? Well, well, inner monologue would just be inner dialogue is talking to yourself. I know my mind’s on my monologue, my inner monologue, you know, dating back decades now. It’s fascinating to not just look, but to, like, see what I was thinking inside back then. so I do go through those things. Yeah.
Tina
And so with money.
Derek Sivers
Oh, right.
Tina
You kind of mentioned this a little bit before. One of my most disliked sayings is “Money doesn’t buy happiness.” Because I think that if you’ve been broke there’s a very big difference. Where do you stand on that. And is there a level, do you think that it’s easier for you now. I mean but you already said that you’re very disconnected from money and the financial gains before the success of CD Baby. But is it easier now to not worry about money now that you’ve got your trust set up? Or do you want to explain what you did with all the money when you sold CD Baby as well?
Derek Sivers
No. I think that we all have a set point where we’re happiest. Something that feels like, you know, these clothes fit me. And I mean that metaphorically. Like this amount of money feels like who I want to be. And for some people let’s say Richard Branson. I mentioned him earlier. I read, I think he’s got 2 or 3 autobiographies, like 1 or 2 that’s like him personally. And 1 or 2 that’s like the history of Virgin. So I read all three. And it’s interesting that over and over again, he seems to find great fun and sport into getting his back against the wall in some sort of desperation, like borrowing money from the bank and then getting it to the final hour, to having to quickly find a way to pay back the bank. And that’s what made some of the most amazing things in his career happen, was the desperation of needing to pay back the bank, and he seems to just be having fun with it. So to him, I think money just represents a kind of--
Tina
Scorecard?
Derek Sivers
No, I think it’s actually just he likes the action of doing things. And then if it’s making money, then it’s doing the thing he set out to do. But it seems to all be fun for him, right? But then there are other people I know that they’re just not, you know, even if they’ve got $1 million or whatever, it’s just not enough, man.
Derek Sivers
You know, I’m just really trying to get here. And they’re like unhappy with themselves until they get to this point. But then I don’t know many people this way, but I’ve read stories of the people who say, like, win the virtual lottery and they instantly blow it on this and this and that, and they come down to here and the argument is like, well, that person’s set point was probably more like, this is how they see themselves. And so if the world gives you this much, you knock yourself down to how you see yourself. So in my own case, I might be a little bit like one of those knock myself down types, but instead of blowing it on stupid things, just once I had enough and then way more than enough. I just reorganized my stuff so that, like, I haven’t made money. Last time I made money 2008 and were 2024 now.
Tina
Speaking and books?
Derek Sivers
No. So like all these books, I haven’t made a dollar off on any. It all goes straight into a charitable foundation I set up. And so I set up like my Sivers Inc publishing company is owned by the foundation. So it’s like not a single dollar ever comes to me. But that was my way of saying like, “Okay, I’m happiest with this set point.” So yes money did---
Tina
That’s fascinating.
Derek Sivers
Thank you. I mean, you know, I think too much. I’ve thought a lot about this stuff. So when it happened that--- say like the I remember the first so when CD Baby was happening for ten years, I wasn’t looking at the bank account. I was just head down, focused on my clients and trying to run things. And I’d look at the bank account and it’s like, whoa, I’ve got $100,000 now. Wow. Because before that I was like a broke musician for ten years, just like working hard to get another $500 to pay my cost of living.
Tina
I still remember when I had $10,000 in my bank account and went, “Oh my God.” I thought that was a dream.
Derek Sivers
Yeah, me too. And so I was just head down and working when the bank account said $100,000, and then it said $200,000 and then $300,000. I was like, wow. And I remember right around somewhere like around $200,000 to $300,000, I thought, “I think I’m set for life now.” Because that amount-- like, I know that I’ve lived on $20,000 before. So now with---
Tina
$20,000 a year?
Derek Sivers
Yeah, I’ve lived on $20,000 a year.
Tina
That wouldn’t cover my kids grocery bill.
Derek Sivers
Yeah. I lived very cheaply for years. Like, I had three roommates and I just ate peanut butter sandwiches, and I just never took a taxi. I just kind of live simply. But the point is that around that point, I thought, well, okay, so I could invest this money if I put it into ETFs or whatever, it would do about 8% per year. And now that it’s $250,000, that would be about $20,000 a year just in interest. I think I’m all set now. And so everything after that point, after 250,000 felt like just cherry on top, whatever. And so then the bank account became like $1 million, then $2 million then $3 million, then $4 million. And I was like, “Geez, oh man.” And I had about $4 million in the bank when I sold the company for $22 million. So that gives a little more context for what’s in the story. When I was like, “Wow, okay, so I’ve got $4 million. I’ve already paid off all my debts. I’ve even helped my parents pay off their debts.” You know no mortgage. Everything just paid off.
Derek Sivers
And I still have $4 million in the bank. So when the company buying my company said we had the price of $22 million, it’s like, “Wow, what the hell am I going to do with $22 million?” And I really spent hours and hours and hours in my diary asking myself, “What should I do? What could I do? What’s another way I could be thinking of this?” I thought, you know, I could buy many homes. And I was like, but I’m only in one at a time.
Tina
I could buy many homes,
Derek Sivers
You know, I could get a fancy car. Like you couldn’t pay me to own a Ferrari. So then I just really thought, like, yeah, the only rational thing to do is to give it to people that need it. If I’m sitting here trying hard to figure out how I can spend it, you know, take a hint like there are people that really need it. And if I’m trying to spend it, that’s just rationally stupid. I can’t rationally live that way.
Tina
But you live on more than $20,000 a year now?
Derek Sivers
I guess. So, it was lucky that my lawyer at the time that was putting together the whole deal to sell the company had a background in tax law. So he said basically, “All right, congratulations. You know, you’re going to have $22 million soon.” I went, “Yeah.” And he said, “What are you going to do with it?” I said, “I’m just going to give it away.” He said, “Are you serious?” I said, “Yeah, I’ve thought a lot about this. I’m just going to give it all away.” And he said, “How serious are you?” I said, “Completely serious.” He said, “Like irreversibly.” And I went, “Yeah.” And he said, “Because in US tax law, there’s a way that we could set this up so that instead of $22 million coming to you, you pay $7 million in taxes and give 15 million to charity. We can put the whole company into a charitable trust. Now, the entire $22 million will go to charity and never touch your hands.” I said, “That’s what I want. I don’t want it to never touch my hands.”
Tina
So you don’t live off that at all?
Derek Sivers
Okay. But then the whole $22 million went into a charitable trust that then pays me out a bit while I’m alive.
Tina
Interesting.
Derek Sivers
Which even then was more than, I only wanted 1%, but the US minimum was 5%. So then I just reinvest or whatever.
Tina
Do you travel economy or business class.
Derek Sivers
Economy.
Tina
Yeah. Like of course you do.
Derek Sivers
Yeah and I drive the cheapest electric car on the market.
Tina
So money’s definitely not a thing.
Derek Sivers
Well look, I don’t want to sound like--- I’m not trying to like, “Look at me. Look how minimalist I am.” It’s really more like---
Tina
It makes you happy?
Derek Sivers
Well. It did, you said, okay, the money can’t buy happiness. It absolutely did for me up to that point. So one time a dear friend of mine was, this is years and years ago we were in Portland. This is like back when I had like $2 million in the bank account. And she was somebody that was like 22 and ambitious and, like, wanted to get successful.
Tina
I remember that.
Derek Sivers
We were good friends and yeah, you know it. Well, she was a lot like you, I think. And she kind of looked at me and she’s like, but we weren’t talking money at all. We were just talking about life. And she asked me a question and I said something that she thought was like, wow, that’s a really good answer. And she goes, how are you, like, so happy all the time? And I went, “Well, first you get $1 million.” She just thought that was the funniest damn thing. She laughed so hard because, you know, money often has these loaded connotations. So it’s like, well, it’s honestly helped a lot. Like having $1 million in the bank gives me this crazy sense of security. I’m like, you know, it’s going to be all right no matter what happens. Like, I could have a major medical problem, I could---
Tina
That’s what it was to me, is the psychological advantage of not being desperate.
Derek Sivers
Yeah. To me, that’s still what it represents. Money represents status to some people. I have no association with status. To me, it’s all about protecting the downside. It’s all about like I just keep it there in a little account, doing nothing. I live as cheaply as I can. So that if something terrible happens, I can feel okay.
Tina
Yeah, but it’s also like my son at the moment, my oldest son, he has his sights set on being a professional golfer, which the odds are very small. There’s not many people that make it, but he’s very determined and planned and going for it, which I love him going for that dream. But it’s an expensive sport. You’ve got to like pay to play right with that, to get into the right places at the right time. And we have had massive discussions on both my kids had jobs as soon as they hit 14 so they could go and get their casual jobs, but he can’t play tournaments on the weekend with that, so he’s had to stop his job, which means we financially support him. And I’m going like the whole lessons around money and what it takes and how much you need to be able to do the different things. What do you think on that?
Derek Sivers
Oh, I mean, if that’s, that’s like one of those, I put that in with the downsides like well, you know, if I have a major medical problem or if I have a kid whose dreams is something expensive, well, then that’s---.
Tina
Because we’ve been they’re going, you know, we could make him do, like, get him to do night jobs and different things, like, really get his grit on, you know? But then is it not our job to try and open as many doors for him as possible? It’s a really difficult.
Derek Sivers
There’s no right answer.
Tina
Yeah, right.
Derek Sivers
And it has to do with a lot with his nature and disposition and your situation.
Tina
Yeah, totally. Anyway, I found that really interesting. So with people that are driven by money, do you see a point in their lives that it no longer becomes the thing? Is there like, or is everyone got that different set point or have you known people that--. So what I’m asking actually, I’ll rephrase the question. So I have my number. I know other people have their number. I know people that have got to their number and gone, “Done. Great. Safe.” And they then set about, you know, the whole do what you have to do until you can do what you want to do. And then they go and they live this beautiful life. And then I’ve known other people whose bar just keeps going up and up and up. What have you seen most? Nmhm.
Derek Sivers
Wow, that’s a good question. Let’s just say that I’ve got a couple good friends that got rich and then just kept raising the bar. And it really frustrates me because I can’t relate at all. And they say it like, well, you know how it is. I mean, you just you just want to get to the next tier and like, no, I can’t relate at all. I mean, that to me is as foreign as if you hear some crazy belief like, well, you know, women in India, if their husband dies, they’ll throw themselves onto the burning fire. I’m like, “In what world would that ever happen?” Like, that’s how I feel about people who pursue more money than they need. I’m like, I do not understand that. I’m a thoughtful person. I try to understand this. I can’t imagine somebody who has $10 million thinking that they need $100 million. I just can’t fathom that. To me it’s like if you have $10 million, fucking stop. You’ve won the game. Quit playing. You know, put down the dice. You know you’ve done it. I mean, like, I’m actually thinking of, like, a board game, you know, it’s like, you know, as if you play monopoly.
Derek Sivers
It’s okay. You’ve won. It’s like, no, keep playing. You know? Seriously, go to sleep. You’ve already won. That that’s how I think about it. That I don’t rationally get it unless again unless somebody it’s like pure joy, like the Richard Branson just wants to keep making companies. Who knows if he’s looking at the bottom line, it seems like. But I have a few friends that keep want to keep wanting to raise that target. And again, I mean, I’m trying to understand it. I’m trying to understand that maybe, you know, we’ll put it in the frame of my “Useful Not True”. Like, maybe that’s a useful belief for them. Maybe to feel alive is to to have a pursuit. Yeah. And we all want to have a pursuit. And maybe there’s nothing more depressing to them than the thought of feeling done. They never want to arrive. They always want to have the the carrot, you know? And that’s where that metaphor comes from, right. On the stick that you never quite get to. Maybe they just like the feeling of continuing to go.
Tina
What do you think the commonality is between the people that set their bar of enough, reach it, and go to sleep. They’ve won the game.
Derek Sivers
Well, I’m the only person I know of my good friends that has done that.
Tina
Really?
Derek Sivers
But hold on. But then I have lots of friends that just, money is just not a thing like they’re pursuing other things. They’re trying to be a great musician, and as long as they’ve got a few.
Tina
One of my best mates just sold his company for a lot, and now he’s writing novels. And he would go in your camp.
Derek Sivers
Okay, cool. I haven’t met many like that. So Morgan Housel, who wrote “The Psychology of Money” he and I have been emailing. He’s one of those people that said, like, “Well, everybody knows the feeling of you always want more. It’s just human nature.” And I was just like, Morgan---
Tina
No, this is not true.
Derek Sivers
I was like, come on. And so he actually said, “Well then congratulations, Derek. You’re the only person I’ve met that hasn’t.” I was like, “No, come on, I can’t be the only one.” But okay, but I do have a lot of friends that are just they’re living their life. They’re being, one of my best friends is a therapist. Another one of my best friends is an illustrator. It’s fine. They’re earning enough to pay their cost of living, and they’ve got some savings. It’s fine. Like we never talk about money. But then I do have a couple other friends that are really, like, they’re really driven by money.
Tina
Okay. I want to ask my final chapter in our conversation. Entrepreneurship. Do you think entrepreneurship is for everyone? Do you think they’re born or made?
Derek Sivers
I mean, not for everyone.
Tina
Love that you say that.
Derek Sivers
Oh, good. I mean, I’ve never really understood the border made, it’s definitely not for everyone. I mean, everybody has different values, and that’s so wonderful that we don’t all value the same thing. And some people really just want to be, like you said, at home with the kids. And, or they just want to be comfortable, or they just want the security of a steady paycheck. They want this number to come in every Friday. Exactly as such, they want to know that that’s there. They want no risk. Yeah, everybody has their different values and it’s wonderful. So it’s definitely not for everyone.
Tina
I asked because I know recently, like probably in the last 5 to 10 years, entrepreneurship has been really glamorized in a way. And there’s so many people in our failure rates for businesses, starting and ending are so high. And I wonder if that’s because people think that they’re being told entrepreneurship is for everyone. Everyone’s got a business in and everyone can do it. And it’s just like a field of broken dreams everywhere. It’s that messaging is a bother for me and the messaging that, but you kind of have been this is that, you know, it just happens by accident and you can work for 15 minutes a day and become rich, of which I don’t think is true in any way, shape or form.
Derek Sivers
Yeah, everyone’s got their different nature that works best for them. Even the whole I mean, let’s use a famous example of Steve Jobs and Steve Wozniak. That’s like I know a lot of Steve Wozniak types, and I’m kind of one of them. I think if I would have been in that situation, I would have rather found a Steve Jobs. You go do the on stage salesy shit. I’m really enjoying being in my Unix terminal, nerding out on my PostgreSQL database. You know, like---
Tina
I don’t know what any of that means
Derek Sivers
Good. Like, I just, I really love the nerdy side of it. A few different times, I’ve tried to hire a programmer to hand off my programming, and just even in the act of preparing my project to be handed off to somebody, I’m like, “No, I love it too much. It gives me such joy.” Actually, that’s one of those other things when I said, my friends have told me that I’m happiest when I do one thing all day. My friends have also told me that they’ve heard me for years, being happiest when I’m programming all day. I love programming.
Tina
How do you reconcile that with, like, when you put a book out and you--. Well, maybe this is wrong also. So my question was going to be but correct me if I’m wrong, you’ve got to promote the book. And you’re doing many interviews and you’re doing speaking, putting your face out there. How do you reconcile that with the programmer, deep thinker that wants to be by yourself?
Derek Sivers
I like the balance. I think if I was only programming all the time, I’d get really lonely and I’d want to book a flight to Dubai and go meet a hundred strangers, you know. But if I had been in Dubai talking to 100 strangers every day for 100 days, I mean, there would be nothing I want more than to be alone in a forest in New Zealand with my Unix terminal.
Tina
Yeah, yeah, that makes sense. That makes sense.
Derek Sivers
BBut everybody has their own, that’s what---. Okay, my problem with some of this like advice giving like, “All right. What’s your morning routine. All right. You heard that everybody. This is what your morning routine should be.” It’s just everybody has such different natures. And you just got to be listening to yourself to notice when your heart is singing versus shrinking. And to look at your past behaviors. This is one of the biggest insights I’ve ever learned is, your actions reveal your values. So no matter what you say you value, just look at your past actions and it’ll tell you what you value. If you say, “I really want to start a business, I really want to start a business, I really want to start a business.” But you’ve been saying that for years without doing it.It would be the right thing for your friends to say, “No, you don’t. You do not want to start a business. Please stop saying that. If you wanted to start a business, you would have done it by now.” And same thing with anything, “I want to get fit. I really want to get fit. No, I really, really want to get fit.” No you don’t. That’s not really your value system.
Tina
Yeah. You know the result don’t want the work. That’s the situation I’ve been in for a lot of it. Yeah. Which is okay.
Derek Sivers
Right. Which is okay because some people like they hate a day without going to the gym. I’m not one of those people. You’re not one of those people. Great. The different values, you know. So I highly recommend to everybody, like, look at your past actions to see your values. Notice what you’ve done in the past that made you the happiest and remember that and use that. Or just notice what you’ve steered towards in a way that, obviously not the things where you’re, like, deeply embarrassed, incredibly, you know, “I used to keep grabbing the whiskey bottle.” Okay that doesn’t mean that’s what you should keep doing.
Tina
Good distinction.
Derek Sivers
Thank you. But, God, that’s been so helpful to me to know myself better through looking at my actions instead of my theoretical.
Tina
Yeah, I do think sometimes we’re too busy in daily life to notice all those times that our heart sings and sinks. I think that’s to take pause and notice, that is a really valuable skill. That would probably become come very naturally to you. Did it come naturally to you?
Derek Sivers
Me personally? Oh, no, I don’t think so. I think I overthink things. It was---.
Tina
In all the right ways?
Derek Sivers
No, in the wrong ways. An old, old, old friend, it’s actually my old boss at the circus. He knows me. I’ve known him since I was, you know, 17, 18. And he always would tease me when I start doing something new, he goes, “No, Derek, don’t overthink it. You always overthink things and wreck them. Just try not to overthink this.” And it’s something I’ve heard a few different people that know me well say. So no, I think I overthink to a fault.
Tina
Have you tried to change that or you can’t change that?
Derek Sivers
I mean, if I really wanted to, I guess I could, but I’m happy with it. And maybe it’s just enough correction, you know. But, no. So I don’t think I’m a natural at noticing what makes my heart sing. I think I have to almost stop and pay attention to that.
Tina
Yeah. When you reflect on the business that you built, what was your greatest moment of joy that you had? Is there one that stands out?
Derek Sivers
I think it was that thing I said where I stopped what did you say? Pushing shit uphill.
Tina
Yeah. Was that a moment or was that more an era?
Derek Sivers
It was almost a moment. It was like a certain month when suddenly just I went from getting two sign ups a week to getting ten sign ups a day or whatever. I was like, “Whoa, this is still rolling.” I was like, “People really like this thing I’ve made.” Yeah, that felt like the biggest moment in my entrepreneur history.
Tina
With you putting so much of your beautiful, overthinking thoughts out into the world, do you ever get worried about negative backlash.? Do you ever get any negative backlash or any sort of like I know for most people that I work with, it’s the fear of putting themselves out there that stops them from spreading their ideas. Do you ever feel that?
Derek Sivers
Yeah. I have an about page on my website. I don’t know if you saw it. It’s long and I say some stuff in there that felt almost too personal, and it was like an experiment to put that on a page. And I put it up there and nobody said anything. And then I started to get a few emails like, “Wow. This really meant a lot to me that you said this online, because I feel the same way, and I’ve felt so bad that I feel this way. And the fact that you said it on your about page, it was really like the most heartwarming thing to me.” I was like, wow, okay. So I guess, I just started getting rewarded. I was going to say rewards. Rewards, rewarded for the times when I said a little more than I thought I should have said. And so sorry to be meta here for a second, but like, even in moments like this, you asked me a couple questions today that I just it’s like my brain quickly went like, “I could say the thing I’m thinking, or dodge the thing I’m thinking. I was like, fuck it, let’s see what happens. I’m going to say the thing maybe somebody will get upset. We’ll find out.” But so far, every time I’ve said the thing that seemed too personal or too audacious, or too rude or too direct. And I had a couple of those today, people will later, like pull that out as like a funny pull quote. All right. Fuck it. If that made for a more interesting. If I could be a better entertainer that way, great. So, no, I’ve been rewarded for putting myself out there. I’ve tried it both ways. I’ve tried to be aloof, and I’ve tried to be too personal. I’ve experimented with both. And with that being a little too personal seems to work for people.
Tina
I mean, that’s what people want, right?
Tina
Yeah, totally. That is all my big questions. Now, I have a couple of quick questions to finish us off. What are the top two 2 to 3 books that you recommend?
Derek Sivers
Yeah.
Derek Sivers
Okay. Well, my real answer is to go to my book list on my website. And I don’t mean to just---
Tina
Do you know I love how you do that. A couple of the conversations that we’ve had and you’ve, like, pulled in the different articles that you’ve already written on your website. It’s like a systems manual for you.
Derek Sivers
Thank you.
Tina
Yeah. I’m like, I love this. I need to do this myself. This is great. Here’s an answer that I’ve already answered 100 times before. Take it. This is no new information.
Derek Sivers
My illustrator friend that I mentioned earlier often will ask me something and I’ll answer with one of my URLs. And that’s why, if you notice, like all my web articles have really short URLs, it’s because I memorize them. So I know that---.
Tina
So you remember everything that you’ve written in the past?
Derek Sivers
Mostly.
Tina
Really?
Derek Sivers
But I memorized the URLs of the one that especially mean the most to me, so I know that if she said something like if I’m talking about parenting, I know I type sive.rs/pa is my article on parenting. The pa I know is-- so I made it that way on purpose so that--. And so she laughs that like she’ll ask me some random question by text and I’ll answer with the URL and she’ll always reply with a little, you know, “Haha of course you have an article about that already.” So---
Tina
Book list?
Derek Sivers
Book list, it is the best answer to--- I could tell you two books right now, but it would be like---
Tina
I want to know your favorite. Do you have a favorite?
Derek Sivers
Well, the one that changed my life the most was “Awaken the Giant Within”. But that’s because I was 19. And I wouldn’t say it’s a great book. When I reread it last year, I was like, “Ooh, wow.” Incredibly verbose. It’s like 700 pages or something, but there’s a lot of good shit in it. But years ago, when I met Tim Ferriss for the first time. I told him I loved that book, and he went, “Huh?” He said, “I read that book. It did nothing for me.” He said, “The book I loved was The Magic of Thinking Big.”
Tina
Yeah, I love that book.
Derek Sivers
But I read “The Magic of Thinking Big”. I went, huh,
Tina
Oh, I love that book.
Derek Sivers
It did nothing for me, but I thought it was maybe it’s because I’ve already read enough books that were similar to it. And then so it’s really interesting that the order that you read and makes a big difference. So I read a fascinating book called “Stumbling on Happiness”. I loved it so much that I read another book about happiness called “The How of Happiness” by Sonja Lyubomirsky, and I loved that one. And then I read a third book on happiness that everybody was raving about, and I was like, “Huh?” And it’s because it was covering the same stuff I just read in the other. But if I had read them in the other order, then the book that I went “Huh?” to would have been my favorite. And the book that was my favorite would have been the--. So that’s why I feel weird about saying like, “Okay, everybody, here’s what you need to read.”
Tina
It’s totally at the time, I took a month off over Christmas, which was glorious, and I read, I’m going to get the title wrong, Benjamin Hardy. It’s like, be your future you now or future you now or be your future self now. It’s one of those titles. And I was like, “This is the best book I’ve read in a long time.” But after I was like, it is a brilliant book, but it was the brilliant book that I wanted to read right at that time. And had I read it when I was in like hectic day to day life, I don’t think it would have had the same. Same with your book. I picked up “Anything You Want”, a friend of mine had recommended it, and I picked it up on on the airplane and went on, read it on the plane and just read it and read it again and sat there staring out the window, looking at the clouds, going, “Huh, huh?” Thinking about all the things which I think would have been different had I not actually had my head up above the clouds.
Derek Sivers
Yeah. It’s different books for different chapters in your life. So I mean, my best advice for books, instead of having somebody say, “These are the two best books you should read.” My best advice is to get a collection, whether you just put them into like, an Amazon wishlist, or you just go buy the paper books and keep them stacked up. The book you need next can sometimes be like almost down to the hour that there can be a certain book that you need right now. That you’re hitting a real frustration, or you’re trying to make a big decision and you think, “You know what I need right now? I need to lay on the sofa for two hours with a book about decision making right now. That’s what I need right now.” Or, you know, you asked about the stopping thinking, yeah, I just want to lay down and read a book about Chinese culture right now, just to get my head out of the other thing I’ve been doing.
Tina
Do you read a lot of fiction?
Derek Sivers
No, no, I watch a lot of movies. So to me movies are my fiction format. Books are my only non-fiction format. I don’t like podcasts. I don’t---
Tina
Interesting.
Derek Sivers
Like videos because for both of those, I hear these brilliant ideas and then they just kind of like, keep going in the stream of time and going, oh my God, I’m on this walk in the forest. And I know I heard--.
Tina
I did that last weekend I was listening to a podcast episode, and it was so good that I had to sit down, and then I went across to the cafe and got some paper and a pencil, and then I just sat there and listened to the rest of it without walking. Because I was doing a walk.
Tina
And I was like, just sitting there listening to it. I’m like, “I almost need this is like a classroom situation.” It was such a good episode.
Derek Sivers
Exactly.
Derek Sivers
Do you remember what it was?
Tina
Yeah. It was your friend Tim Ferriss interviewing the Netflix CTO. It’s amazing.
Derek Sivers
I haven’t heard that one, but that’s my problem with--
Tina
No no, no, no, I listened to Tim’s interviewing the Spotify person straight after. It was the Lenny podcast interviewing the Netflix CTO.
Derek Sivers
Okay. Lenny.
Tina
I’d never heard of it before. A friend of mine sent the episode, and I was like, because I’m trying to be a better leader at the moment, to learn to manage people. And she was amazing and I needed to take many notes.
Derek Sivers
You know, not that anybody needs to hear this from me, but. I think whatever format works best for people. You shouldn’t think that you should use some other format because other people are. If you just love short form videos and that’s how you learn. And if that works for you, then don’t think that you’re supposed to be reading books like, “Oh, I’m a bad person because I don’t read books.” It’s like, well, if it doesn’t work for you, talk about actions revealing your values. If you just don’t want to read books and you think like, “Oh, I should read a book.” Then just don’t just go with whatever is working for you.
Tina
You know, to me, laying down or sitting down and reading a book is like the most indulgent, decadent, delicious thing. That’s why I was so surprised you don’t have a bookshelf. To me, like a tablet is not the same as picking up a book and the smell of it and the feel of it, and writing notes in there and the back pages. I rattle my thoughts and I love them.
Derek Sivers
See, my system is in my e-book reader. I have a thing where every time I read an interesting idea, I hold my finger down on it, I drag over the idea I liked, and when I let go, it creates a highlight. When I’m done reading the book, I connect a USB cable. I have--
Tina
You have all the highlights.
Derek Sivers
It connects the highlights, and then I go through those highlights and I put them into my own words. And then now they’re in a system in text files that I review often. I come back to this often. They’re also searchable by word or phrase or date. So I can say show me all the books that mention commitment.
Tina
Oh, that would be cool.
Derek Sivers
That’s why I love digital, why I love my text files. Is that this idea of, like, I do that with my diary, too, “Show me, uh, show me all of my thoughts on Erika the week we met.” And there it is right away. I don’t have to flip, flip, flip, flip.
Tina
Erika is your ex-wife?
Derek Sivers
No, no.
Derek Sivers
Who’s Erika?
Derek Sivers
Okay. You actually want to know. One of my favorite people I’ve ever met. Maybe even my hero, Erika LeMay erikalemay.com. You could see her.
Tina
I will.
Derek Sivers
She is an aerial artist that I got to know in 2017. And it’s just one of my favorite people on earth. Yeah, she’s a superhero.
Tina
I love that.
Derek Sivers
She’s like a living superhero. She’s like the, Nietzsche talks about the Übermensch. Like she’s living it. She’s amazing.
Tina
Favorite show you’ve recently watched? We know it’s not reality TV. Do you watch TV? Just movies?
Derek Sivers
Just movies. I will translate your word show to mean movie or things.
Tina
Yeah. Poor Things?
Derek Sivers
Yeah. That’s my candidate. Different people take different things out of this movie.
Tina
Is it dark?
Derek Sivers
Yeah, yeah.
Tina
It’s probably not for me.
Derek Sivers
But Bella, the main character that Emma Stone plays, I saw as a wonderful role model of learning. The movie starts when she’s basically a day old and you watch her learn and become sophisticated and go from having a mentality of a one day old and to being really sophisticated. But it happens quickly. All right. No, no, I can’t wreck the spoiler. Okay. But other people say, Oh, yeah, Poor Things was a brilliant metaphor of how women are treated in the media and how they’re infantilized.--” Is that how we pronounce it?
Tina
Yeah.
Derek Sivers
“By some and respected by others. Until they prove themselves.” Like whoa, I didn’t get that reading. So it’s it’s one of those movies that can mean different things to different people. But I saw it in the cinema in New Zealand. I just walked out just like, “Whoa.” I like, thought about it for days, like I kind of want to have like a little like Bella action figure on my desk to just like, I just like, her character was really inspiring to me.
Tina
Okay, I might try the dark. Is there a question that you ask people to get to know them without too much small talk?
Derek Sivers
That was a good one.
Tina
Thanks. Because you don’t strike me as, like much of a small talky guy.
Tina
Really?
Derek Sivers
I can.
Derek Sivers
Yeah.
Tina
Okay. I’m not good at small talk.
Derek Sivers
Well. My friend Tynan came to visit from America. He came to visit me in Wellington. I think he was just passing through for a day or two and Tynan calls himself an extrovert, and I’ve always called myself an introvert. We hung out for like 3 or 4 hours where he met me at my apartment in central Wellington, and we walked around for a bit and met up somewhere and then, like, went back to my house. That’s it, we just kind of went out to get something to eat, and then we came back to my apartment and as we came back to my apartment, he goes “I think you just talked to more people in the last hour than I’ve talked with in weeks.” And I went, “Really?” And he goes, “Dude, you talk with everyone everywhere you go.” And huh, I guess so. Like, yeah, I think, I kind of make chit chat with people around me. I think, like, yeah, I talk to strangers with cute dogs. I talk to just people I meet. Yeah. So I might be more of an extrovert than I realized. So yeah, I’m okay with small talk. Oh. So your real question.
Tina
Do you have a question that you ask people or no?
Derek Sivers
No, not a set one, no. You know, this reminds me of is years ago a friend of mine who was dating said, “What is your sense of humor?” I said, “What?” She said, “Well, how would you categorize your sense of humor?” She says, “Because I met this guy that he asked me that question, wanted to get to know what my sense of humor was. And he said that his sense of humor is sarcastic, and he wanted to know which of the five categories my sense of humor was in.”
Tina
Was he being sarcastic when he said that?
Derek Sivers
No. He was trying to get to know her quickly on a first date, and I said, “I don’t like this question because it assumes that your sense of humor is the same no matter where you go or who you’re talking to.” But to me, the whole thing about humor is it’s kind of responsive. It plays off the scenario. If you just just barged your way through life with the same sense of humor, no matter what the scenario was in, you would not be very funny. And so I think it’s maybe the same thing with conversation. That there’s some people that asking a get to know you quick question would be a horrible way to get to know them. Like you’d have to---
Tina
Embarrassingly so, my sense of humor is, I laugh when I get videos of people hurting themselves.
Derek Sivers
All right, a lot. Did you ever watch jackass?
Tina
Not for a long time, I haven’t. But literally, like, I think my husband and I, our main form of communication is him sending me videos that he knows will make me crack up. And I try not to laugh because I know it’s awful.
Derek Sivers
People like accidentally getting hurt. Like slipping.
Tina
Like when they slip over, when they’re like, you’re walking down a street looking at something, playing on their phone, and then they hit their head on a post. I love it. Dogs, when dogs slip up. I have three dogs. I love dogs, but when dogs do funny things. Oh my gosh.
Derek Sivers
I think one of the funniest videos. I think I’ve laughed harder than I’ve ever laughed at one video was, it’s an old one that’s probably been around for like 15 or maybe even 20 years now of a guy that is so drunk. It’s like the security camera captured this. He’s in, like, a supermarket or whatever. And he’s so drunk that he can’t get himself to open the cabinet. He’s like trying to and then he, like, falls over backwards and it’s like, seriously. It’s like two minutes of him trying to get up and he can’t remember how to stand up, but he keeps trying.
Tina
That’s my sense of humour.
Derek Sivers
I was just like cheering and crying and laughing at this. And like a more sensitive friend of mine was standing there just going like, “This is horrible. How could you find this funny? That poor man.” I was like, it’s fucking hilarious. Because at one point he does stand up and he’s like, he’s like tries to get it together and he collapses into the bag of chips and oh God, yeah, I should just download that. There’s a great little script that you can, do you use Mac or Windows?
Tina
Mac, I told you I’m clichè. I didn’t say that when we were--.
Derek Sivers
You didn’t add that in your list of cliche items, but, there’s something called YT-DLP. I don’t even know what the DLP stands for, but the YT stands for YouTube YT-DLP. You can use it to download any YouTube video. So you can just keep a local copy. So if there’s something you’re going to watch again and again and again and again and again. You don’t have to keep watching all the ads every time. You can just own the little MP4 video file. So that’s what I do for like my favorite videos of all time. So I should go find that video again.
Tina
Yeah.
Derek Sivers
I hadn’t thought about it.
Tina
I’ll see if I can find it. Okay, last question. With such few things that you own as a minimalist, is there one product that you have that you can’t live without?
Derek Sivers
Okay, assuming you don’t mean can’t live without literally.
Tina
Not like an essential. Like your toothbrush. Like I mean something you don’t need. Like I’ll distinguish it with that. A product you don’t need for everyday life. Do you have one?
Derek Sivers
I have a really nice keyboard that I find makes a massive difference in my happiness. So I have two computers. I have a desktop and a laptop. So like when I’m out on a trip like this, I’ll bring my laptop with me. When I’m at home, everything else I do is on my desktop and for the desktop, I just a couple of years ago, got a mechanical keyboard from a Chinese company. I forget the name of it. It’s actually on my--. I have a users page, so it’s on my website somewhere. Of course I know the URL sive.rs/uses
Tina
Like Derek uses this.
Derek Sivers
That’s what Derek uses. It’s actually a common thing a lot of people with personal websites. It’s kind of like how many sites have a slash about.
Tina
Yeah mine’s tools but uses is way cooler.
Derek Sivers
Well I think uses-- I actually probably would have chosen tool’s too, but uses has become a bit of the norm. So in this case I just went for the norm. Do you have a now page?
Tina
Now page. No. What’s a now page?
Derek Sivers
It’s the page that says---
Tina
Like what I’m working on now?
Derek Sivers
Huh.
Tina
Oh, I like that.
Derek Sivers
Because social media doesn’t cover that. Like, if I were to tune in to your feeds right now, I might kind of see what’s kind of interesting, but it wouldn’t give me the gist.
Tina
Like what you’re reading and what you’re thinking about.
Derek Sivers
It’s what you would tell an old friend that you haven’t seen in too long. And if they were to say, like, ‘What’s been up with you, what’s you been doing?” It would be the like the one page it kind of says, like, “My kids are 15 and 16. This one’s really into golf. I’ve been working on this.” You know.
Tina
I like that. I’m gonna make a now page.
Derek Sivers
“We’ve been at this home for three years. We’re planning on staying.” So the slash now. And then, if you do that, then email it to me. And I have a website called nownownow.com where I collect all the now pages from. So they’re lik§ maybe 2500 personal pages where people have created a now page on their site. So I put that on nownownow.com.
Derek Sivers
So anyway, your.
Tina
Yoour product, your keyboard.
Derek Sivers
It’s called midnight silent switches. So it’s like oh it just feels so nice. I just noticed my fingers don’t want to stop typing when I’m typing on it. I’m just like keep, oh, it feels so good to keep writing.
Tina
Because it’s smooth or because it clicks?
Derek Sivers
No, because it doesn’t click so much. I used to have a clack clack clack clack clack clack clack clack clack clack that.
Derek Sivers
Yeah I used to have one of those and it physically felt nice, but I’m not a abrasive person. I don’t like to be loud. So I found that I was actually subconsciously typing less because I didn’t want to create a racket.
Derek Sivers
In the house. So that’s why I bought the silent switches and I just noticed, like, God, it’s like---. I mean, look, there are things like, I love good black tea when I drink good black tea. I’m like, “Oh God, oh man, this is good.” The way that people are with their morning coffee. That’s how I’m with like good black tea. But even not in the morning. Just always I love my wonderful black tea. But when I type on this keyboard, it’s a little bit like that like, God, I love this keyboard. God, it feels good. So I’d just give that as my weird item.
Tina
Yeah. Nice.
Tina
There’s things you’re attached to. If you moved, would you take it with you?
Derek Sivers
Yeah. See, there is a good question, “All right, Mr. Minimalist, if you were to move with one suitcase, what would you take?”
Tina
Yeah.
Derek Sivers
Then the other thing would be my Berkey water filter. I got it when I moved to England, you know. Have you spent time over there where they have the hard water?
Tina
Yeah, yeah--
Derek Sivers
If you try to make tea.
Derek Sivers
Not a long time, but. Yeah.
Derek Sivers
It has a film on top. So I got it because of that. So that would be on my short list.
Tina
I mean even America.
Derek Sivers
Really?
Tina
Yeah. Water that comes out of the tap there’s real weird. I mean, from New Zealand water to American water.
Derek Sivers
Right. I went one direction, I didn’t--
Tina
You haven’t been back?
Derek Sivers
Not really.
Tina
Really.
Derek Sivers
I left in 2010. I’ve been back a few days since.
Tina
Oh, wow. When’s your next trip back? Don’t have one planned?
Derek Sivers
Maybe never. Yeah.
Tina
Wow. Interesting.
Derek Sivers
There’s a burrito place that I would miss if I never went to America again. But, you know, other than that, I’d be all right.
Tina
Yeah. Amazing.
Derek Sivers
It’s just there’s so many other places I want to go on Earth. You know, it’s like if--
Tina
Do you keep track of how many countries you’ve visited?
Derek Sivers
I do. I haven’t counted, but I have a file. I thought I should start doing this before it gets too late. Starting about 15 years ago. My file is the year and the country that I’ve first entered on that year. So like if I go back to a country multiple times, it’s still only appears once in the list. But I try to remember the year that I first went to a country. And so like last year, I went to Cyprus for the very first time.
Tina
Yeah,
Derek Sivers
But I also went to Israel. But I had been there once before, in 2004, so Israel did not get added. So it’s still up there in 2004, but last year was Cyprus and United Arab Emirates and Oman for the first time.
Tina
I love them. Well, that is all of the questions that I have.
Tina
Oh that’s everything. You know, everything about me now.
Tina
I can there’s many more I could ask you for the rest of the day, but I am conscious that I’ve taken a lot of your time. I appreciate it so much. Thank you so, so much. I know that you get a lot of offers and this one you would have gone, “Who is this person?” And you said yes, which made my I was going to say made my day. It made more than my day.
Derek Sivers
It made my hour.
Tina
It made my hour, it made my day. It made my week. But it’s also, you know, it’s pivotal in that you were the first one on that dream 100 list. And now I will try and do more interesting conversations with interesting people, because I really appreciate it and sharing your thoughts and hopefully everyone being able to question some of the beliefs that we hold as well as, you know, me selfishly asking a lot of questions that I wanted to know.
Derek Sivers
Thank you. Well, I’ll get Celine in next. I think she’s waiting outside since we’ve got the nice studio set up so.
Tina
I love that so much.
Derek Sivers
But, yeah, I’ve never not--. I shouldn’t say never done this, but this thing with the lights and three cameras I.
Tina
I know cool, right?
Derek Sivers
I haven’t done this. This is really, really rare and wonderful to do this. So thank you for this fancy setup.
Tina
Well, I mean this was also Dan was asking me like, how how far through the podcast you are. And I’m like, this is episode 260 something ish. And he was like, “Oh wow. So you’re used to this?” I’m like, “This is the first time I’ve done this.”
Derek Sivers
Cool.
Tina
I have never done this, but you’re Derek Sivers. I’m like, I’m not going to bring my little Canon and set us off on our Rode mics and be like, “I hope the sound works.” This is why this. So thank you.
Derek Sivers
I’ve been standing in my sound booth in Wellington a lot, and so it’s really sweet to--
Tina
Yeah, it’s much better. Thank you.
Derek Sivers
Thanks everybody.