The Paul Dermody Podcast
host: Paul Dermody
entrepreneurship, writing process, pragmatism, travel and cultural immersion
listen: (download)
watch: (download)
Transcript:
Paul
Derek Sivers. Welcome to the show.
Derek Sivers
Thanks, Paul.
Paul
In a minute or less, how do you want people who haven’t heard about you to know you?
Derek Sivers
I’ve done a bunch of things. I was a full time musician for many years. I joined a circus. I was the ringleader of a circus for ten years of my life. Did over a thousand shows around the US. I was a full time musician then, selling my own music online. And I started a little store just to sell my CD. But then other musicians asked if I could sell their CD too. So I started a little store called CD Baby that grew to be the largest seller of independent music on the web, and I did that for ten years. Until I just got felt done with it, and I sold the company in 2008, gave all the money to charity, and have just been traveling the world since, writing books of pop philosophy.
Paul
Brilliant. I actually read-- I was saying to you before we went on, I read your is it the most recent one, How to Live?
Derek Sivers
It is. Yeah.
Paul
And I loved how succinct that book was before I even talk about the book writing process. As someone who is starting his journey writing, I don’t relate to most productivity hacks online. I don’t relate to much success stuff, gurus telling you how to win the day and win business. You’re one of the few people that comes along and and talks to my soul a little bit. The way you talk about how your book writing process, but also I heard you say in another podcast, someone tried to invest in your big business CD Baby before, right. They tried to inject a fortune of money into it and you were not motivated. You said, no, I don’t want I’m good for money. I don’t want this extra workload. I don’t care about the money. And honestly, that was so refreshing to me to hear like a successful, acclaimed business person say, no thanks, I’m going to chase soul rather than cash.
Derek Sivers
Yeah. I mean, it’s the-- God, what’s that term? Like the devil’s bargain, no such thing as a free lunch. Whatever those sayings are. That I saw friends in New York City, I was living in New York City when I was running this business. So I had other friends in New York City during that first .com boom that did take a lot of venture capital money, and I saw what it did to them. It messed up their focus. Suddenly their business that used to be about pleasing customers now became about pleasing investors. And they were spending stupid amounts of money on things like ping pong tables and decorations in their office, when that stuff doesn’t benefit the customer at all, it was just to stroke their own ego to say, “Hey, look at us, we’ve made it.” And because they had the extra money that was given to them by investors that they didn’t really need and all of that, I just felt it was really unhealthy. And also, I don’t like having a boss, who does? Like once you have investors, you kind of have a boss, you have somebody you have to report to. Fuck that. No way. I’d rather just owe nobody nothing and just be independent. So no, I said no to all investors. I started the company with $500 and by the second month it was profitable. So I never needed investors.
Paul
And when you sold it, it was extremely profitable. It was lucrative. And it made you seven figures, right?
Derek Sivers
Yeah. 7 1,2,3,4,5,7,8
Paul
In the millions
Derek Sivers
So CD Baby was profitable. Yeah. I mean, it was profitable since the second month. And by the time I sold it, it was making 4 or 5 million a year net profit. And I was the sole owner. So, yeah, I had enough money. I had more money than I’ll be able to spend in my life. So when I sold the company, the selling price was $22 million. And I was talking with my lawyer who had a background in tax law, and he said, “Well, congratulations. So you’re going to have $22 million by the end of this year. What are you going to do with it?” And I said, “Oh, I’m just going to give it all away.” And he said, “Are you serious?” I said, “Yeah.” He said, “How serious?” I said, “Completely serious.” He said, “Like irrevocably, irreversibly serious. Like you’re absolutely sure you’re going to give it all away?” I said, “Yeah, I’m going to give it all to charity. I don’t need it.” And he said, “Well, if you’re just going to give it to charity, let’s do this.” And he structured the sale of the company in such a way so that I created a charitable trust first, transferred the company into a charitable trust, and then the charitable trust sold the company to the buyer. So that way, all $22 million from the sale of the company, all of it went directly to charity without touching my hands that way. Yeah, the whole $22 million went to charity instead of having $22 million come to me, $10 million going to the tax man. And then having only $12 million left for charity, we structured it in a way so that all $22 million went to charity and never touched my hands, which made me feel a lot better because then I could avoid feelings of regret.
Paul
Wow. It’s quite the story. I mean, parting with that kind of money is a hell of a life decision. Did you at any point have regret thinking, what am I doing with this money?
Derek Sivers
No. I mean, we all have a self image of who we want to be, right? Anybody listening to this like, I’m not going to tell you how you should be. If you want to live in a mansion with six Ferraris, good for you. But I just didn’t want that life. You know, I had already paid off all my debts. I’d paid off my mortgage, I paid off my mom’s mortgage, you know, like I’d already done all the things you do with money. And I’d already kind of had that feeling of like, “Well, that’s it. Like, is this all there is?” Right. There was nothing else I wanted to buy. So to me, that $22 million just felt unnecessary. And it was just a no brainer that this should go to people who really need it. So it was not a tough decision. No.
Paul
Well, I think that’s even more relevant as to why relate to your content so much. You clearly have a definition of enough. You’re clearly able to define what you need to live a happy life. Unlike the cliché unhappy millionaire who hasn’t defined enough, who continues to strive, who’s clearly trying to close the gap on external insecurities, it comes across very much in your personality. When I’ve seen you online and when I’ve read your work. Thanks.
Derek Sivers
Thanks. Yeah, there were times in my life where the only thing I had was my confidence, you know. So I guess that might have had something to do with it. Yeah. I never felt like I had to prove anything to anybody.
Paul
When you only had your confidence. I’m assuming that’s right back when you were beginning to be a musician and you were full of maybe hope and not so full of cash.
Derek Sivers
Yeah, and there were some other times too. On my website, there’s a blog post called loss. So you go to my URL is sive.rs/loss. Loss is the blog post where I wrote about this year that was like the hardest year of my life, where just like everything went wrong, my company went nuts, I got divorced, they were renovating my home, so I was like homeless for a year, you know, not really homeless, but it’s like I was sleeping on the floor in the warehouse and it’s just like everything went wrong. And I think when I think, like, all I have is my confidence. That was a year I kind of apply that too. But yeah, you’re right. Also like the early days as a musician when being an independent musician is always an uphill struggle. You know that nobody makes it easy for you.
Paul
Yeah, I can imagine. I heard you say it. I think it was on the Tim Ferriss Show where you were basically making about 75 bucks a night, but you had spend the majority of that on transport anyway. So you were doing it with the hope that it was going to lead to somewhere else.
Derek Sivers
And it did. You know, it was totally worth it. It’s funny. You know, whenever-- I was actually just talking with a friend about this yesterday. That she has a job offer that she’s not excited about, and we’re talking about how it’s kind of cool that whatever she’s not excited about, somebody else is excited about that. So the way I joined the circus was I knew this bass player and the gig had been offered to him first they said, “Hey, how’d you like to play guitar at this pig show? It pays $75.” He’s like, “What? 75 bucks? No way. That’s not worth it.” And he’s like 18 years old, maybe even 17. And he’s like, “Hey, Derek, do you want this gig?” I was like, “Oh hell yeah. My first paying gig.” I was like, “This is awesome.” I didn’t care that it was $75. And like you said, I had to spend a $50 bus ticket to go round trip to go do the gig. But it was a paying gig. I was excited, and this is nice to remember that whatever doesn’t excite you, there’s somebody somewhere that is excited about that. It’s a good argument in favor of delegation. You know, whatever tasks you’re doing that you’re not into, see if you can find somebody else to do it, who would be excited to do it.
Paul
A hundred percent. My personal training business. I love the people side of things, but I really dislike the technology side of things, I’m just not very good at it. So my girlfriend is the polar opposite. Somehow we function and it works, and now she’s working with me and it’s the perfect compliment. So I can definitely echo that sentiment that what stresses me out is her bread and butter and vice versa. Cool. Yeah.
Derek Sivers
Cool. I love that.
Paul
Yeah, absolutely. So have you always been somebody then who just followed his curiosity and was able to follow his passion? The reason I ask Derek, is because something I noticed throughout life. People, all of us unintentionally project a concern for people that can manifest as doubt, that can dampen confidence. You might say to me, “I’m going to be a musician.” And I say, oh, Derek, be careful, but I mean it from love. Have you always been someone who could just follow his heart rather than maybe voices of doubt, externally, internal or otherwise?
Derek Sivers
Yeah, I think it wasn’t passion so much as knowing that I wanted it more than most. So like when I was 14 years old and I got really into playing music. I would just like 6 to 8 hours a day, be doing finger exercises on the guitar and practicing things and arpeggios and scales and chord progressions and you couldn’t get me to stop practicing. I was so into it. And that just applied to everything else. You know, once I decided to start playing bass, you know, I would just practice bass for hours. And once I started to get into arranging to put together all the pieces, I could learn how to make good drum beats and keyboard arrangements and such. I would just spend hours on this stuff, and I just kind of found that I was always the hardest worker, that other people would approach music in a kind of like, “You know, yeah, man. You know, maybe we’ll make some tunes later, you know, here, take a hit of this.” And it was just like this casual thing. Whereas to me it was like I was very type A and focused.
Derek Sivers
So I think I knew that I could do this thing. I think I knew that I had the temperament, the composition to really pursue this. And I did. So, you know, then I went off to Berklee College of Music. Deeply head down, being the best musician I could be. 20 years old, I moved to New York City. I was very strategic, so it wasn’t like dreamy. It wasn’t like I’m going to follow my passion and dream. It was just this feeling of like, all right, this is what I’m going to do. I can do this. I can be one of the ones that makes this happen. And in a way, I did, you know, not in the way I expected. I was hoping to be the next Prince, but instead I became more of like a record producer. And then I accidentally started CD Baby. And that’s where it turns out that was my surprise unique contribution in the end, was to have done music for ten years, enough to understand what it was like to be a musician and then provide this service to a quarter million other musicians.
Paul
Are you sick of talking about CD Baby with people? Does it ever get on your nerves the more people probe about it?
Derek Sivers
I wouldn’t say on my nerves, but I’ll admit a lot of what I’m saying right now, I’ve said a hundred times before, and it’s a little old hat. I try to put a new twist on it and not just use exact word for word, as I’ve said it, but yeah, I’d love to talk about anything else.
Paul
Okay, cool. That’s the reason I was asking it because--
Derek Sivers
It seems like you wanted to talk about it. So, you know, when I give up time to go on a podcast like this, I block out the time and it’s all yours however you want it to be. You know, if you said, “Hey, Derek, could you do a little dance for us? Sing a song?” I’d say, Well, all right, I gave you the hour. Paul.”
Paul
I admire the radical honesty. I want to find that balance between not making this an interview style, plus the fact that people will be hearing you for the first time today. But okay, let’s segue entirely your latest, your latest book, “How to Live”. Your Line “You’re not supposed to be easy to explain.” Tell me a little bit about that.
Derek Sivers
Ooh. Do you have the paragraph in front of you or just the line?
Paul
I took note of the line, but you were talking about the idea of reinventing yourself and and how if you keep continuing to define yourself, I’m going to give you an example. I’m going to throw one at you. Yeah.
Derek Sivers
Yeah. Great. Thanks.
Paul
All right. Let’s say I’m trying to break a diet cycle and I continue to identify myself as an emotional eater. I’m an emotional eater. Therefore I behave in such and such a way or I’m an introvert. Therefore I have no friends.
Paul
Yes. So I’ve actually taken a couple of highlights from the book that I have in my Kindle in front of me, but that was the one that stood out to me the most by a long way, is you’re not supposed to be easy to explain. I want you to expand a little bit on that. I hope that’s a good enough segue for you.
Derek Sivers
Perfect example.
Derek Sivers
Yeah, nobody’s asked about that line before. I really love that. So by the way, anybody listening to this the “How to Live” book it’s kind of halfway in between prose and poetry. It’s written almost like poetry, where it’s like every single line that’s in there used to be a whole page, like my rough draft of the book was 1300 pages, and then I edited it down to only 115 pages. So now really, almost every sentence that’s in there represents what used to be a whole page. So the idea of you’re not supposed to be easy to explain. You just picked two perfect examples. People tend to overgeneralize in order to explain themselves to others, to say, well, I’m an emotional eater or I’m an introvert. Both of those things have way more nuance than they let on. That there’s, “Yes I have eaten when emotional in the past, but actually only in these situations and for me it’s only sadness and then only if it’s available, but only when I’m in this place where I really like the food.” But then to overgeneralize and say I am an emotional eater. It’s conversationally considerate to not go into the boring details when talking to somebody, but it’s not the most accurate.
Derek Sivers
So I think people sometimes overgeneralize themselves. They oversimplify themselves, which ends up pulling themselves farther away from the truth. Right. The truth, unfortunately, is not succinct enough to put on a bumper sticker or a rule of thumb, or an Instagram jpeg. The truth is always more nuanced than that. And we make these simple slogans as like a rule of thumb. But they’re deliberately contradicting. Because the truth is, we need this slogan for this exact situation. But on the other hand, if we’re feeling low in energy and it’s early in the morning and we just did such and such yesterday, well then, now that doesn’t apply. This one applies. But on the other hand, not if my family is staying with me right now. Then it’s a whole different situation. But my kid is sick and therefore this one doesn’t apply anymore. You know, it’s like the truth is always more nuanced like that. But that’s boring to explain to other people. So we oversimplify in order to make ourselves easy to explain. Yeah, that’s where that idea came from.
Paul
You put it almost in a sense to where there’s that ego identity that if I define as something, it justifies this as well. It justifies this behavior. Yeah.
Derek Sivers
Yeah. Well, okay. You’ve seen in your field people who adopt a new practice and then upon doing that, they adopt a new persona. Like so suddenly people who get into yoga, for example, it’s not just that they do yoga. No, no, no, they need the whole thing, the namaste and this and they start putting different kinds of decoration in their room. They want to adopt this persona. Or if somebody wants to be a certain person that suddenly now they’re wearing the black leather jacket and they need to drive a Harley-Davidson, not a motorcycle, not any motorcycle. It needs to be a Harley-Davidson because they want to buy into this persona. It gives a sense of certainty or no, that’s not it, not certainty, belonging. It gives a sense of belonging and self-identity to say, this is who I am. I am a yoga person, you know, I am a Harley-Davidson biker, whatever it may be. I think it gives a sense of certainty and peace inside to know what category you fall into. But yeah, I think these things are really oversimplifications.
Paul
You’re a multifaceted guy, so have you had to analyze and observe that about yourself? Have you had to break from I’m music, I’m writing, I’m such a person.
Derek Sivers
Yeah. Really just once Oh, no. Okay, I’ll do twice. Yeah, I was just a musician. I mean, nothing but a musician for 15 years from the age of 14 to 29. You couldn’t get me to do anything but music. I didn’t even read books. I had no interest in anything but making music. I was very narrow. And then when I started CD Baby, it was fascinating. But it was confusing for me because, oh my God, I’m a musician. What am I doing? But this is fascinating me. I was having so much fun building the website. I did all the programming myself. So I’m learning databases and I’m doing HTML and it was fun. It was intellectually challenging in a way that getting in the van and doing yet another gig was not intellectually challenging, so it was confusing for me for a while to say that like, “But I’m a musician, but this is fascinating me. And that is not.” So that took a while to adjust myself in. But it was easy because all these musicians were saying thank you. Like people are like, “Oh my God, thank you so much for doing this.” So I was getting all of this social reward for making this identity change.
Paul
How so? Why were they thanking you?
Derek Sivers
Oh, for making city baby like. I mean, sorry if this lacks context, but we’re talking about 1997. Like Amazon was just a bookstore. If you were a musician in 1997 trying to sell your music on the internet, the only way to do it was a guy named Derek in New York. That was it. I was it. I was the only one that would sell your music in the world. So a lot of musicians were really, really thankful that I was doing this thing. I mean, you know, nine months later, a lot of other competitors came along. But there was this wonderful time when people were so thankful that I was doing this thing because nobody else was. And so that felt really good and definitely helped my transition from being a musician to being a musician’s helper. So I said I was going to give you two examples. Now imagine this. So I’m a musician’s helper. I didn’t even really think of myself as an entrepreneur. I thought of myself as somebody helping musicians. But once I sold my company for all that money, people put me into this category of entrepreneur. And they thought, “Oh, you’ve sold a company for millions, so you’re an entrepreneur.”
Derek Sivers
And they asked me to come speak at universities to business school students and other entrepreneurs wanted to meet me, and people wanted to talk about entrepreneurship. And I fell on myself like, I don’t like these people I’m around mostly they’re talking about investment. Like, how do we get investors? I need investing, I need angel financing, we’re getting a second round of our series B, something I don’t know. And they talk about Q3 results and shit that I just couldn’t relate to, I had no interest in. And so that felt weird to realize that I had been categorized into an identity that I didn’t want so it took me a couple of years to, like, deliberately sluff that one off. I ended up writing a book called “Anything You Want”. That’s just here’s my story of starting, growing and selling CD Baby. That’s it. That’s my story. I don’t want to talk about it anymore. It helped me put that in the past. And so now I just write these books on life and not business.
Paul
Reading Anything You Want was my introduction to you. It was after that then I found you on other work like podcasts and stuff like that. So just so you know, I wanted to share that. Did you always know you wanted to be a writer, even when you were a musician? Was the book something you always had in you?
Derek Sivers
No, never. Quite the opposite. For years, people asked me if I’m going to write a book, and I said, “No, no way. I don’t want to write a book. I’m just going to put my blog posts out.” It’s kind of like the thing about investors, like a book felt like responsibility, whereas just posting blog posts just felt light and easy. So no, I thought of myself as a-- I don’t know. I thought of myself as an entrepreneur for a while, programmer, maker. And sometimes I’ll share what I’ve learned on my blog. But then one of my heroes called me one day. So Seth Godin, who I always admired, like literally called me, like my phone rang and it’s this number I don’t recognize. I said hello and he said, “Derek, Seth Godin, how are you?” I said, “Hi, Seth. Wow.” And he said, “I’m starting a new publishing company and I want you to be my first author.” So I said, “Okay.” So it’s like, who could say no to that? So no, it was only because Seth Godin asked that I wrote that first book. But then the reason I did it some more is that I noticed who my heroes were. And this is kind of interesting maybe for your listeners. Because sometimes you’re not sure what direction to head in life. You’ve got a few different paths you could take. You know. And it helps to ask yourself, who are your heroes. Like who do you admire the most? Because I think that helps show you which way you’re facing and which way you should be going. So for me, I felt kind of equally like a programmer, maybe an entrepreneur by my own definition. I liked writing, but I thought of it as like a side effect of everything else I was doing. But then I realized that all of my heroes were authors. That I loved these books I was reading so much that these were the people I looked up most to in the world. So I realized I should be an author.
Paul
Similar to me. The people I look up to are the most all have a book or some written piece of work under their belt. Absolutely. And that’s what’s gotten me so curious in the last while. It’s been something I’ve talked about. I’m the typical cliche, someone who’s talked about it for a long time, but only recently have I sat down and developed a consistent writing habit. And similar to you, I think about it slightly different to you, but I’m sure it’s the same thing. I don’t think about so much my heroes, but I think about the outcome I admire. Or people who people who get outcomes I admire, even if I don’t like the whole of them, or if I don’t aspire to be the whole of them in one narrow domain. How do they do that? And I’m always curious. It’s why I wanted to talk to you today. It’s why I wanted to to pick your brain about writing. Because I think I heard you say something before, and it was a one of those moments where I to kind of stop what I was doing and pay attention to the podcast. You say that a book isn’t actually like a crazy process. You can write a book relatively quickly. It doesn’t have to be some big, massive Churchillian speech that you spend years and years and all this kind of stuff doing. And I heard that, and I thought that was the first time it had been broken down so simple to me. You’re the first person to make me think a book can be written, and it can be written by somebody who’s not necessarily established, esteemed author yet.
Derek Sivers
Wow. Yeah, thanks. That’s nice to hear. I mean, that first book for Seth Godin, I did it in ten days.
Paul
Yeah, I think that’s the exact line that you wrote for Godin in a very short period of time, which really intrigued me because I imagine just your mindset, your psychology would have been, “Fuck, this is Seth Godin. I cannot mess this up.”
Derek Sivers
Well, it was more like once he said he wanted me to write it about the CD Baby stories. I thought like, “Oh, that’s easy. I got plenty of stories about CD Baby.” And so all I had to do was just think to myself of the stories that I had been trading in conversation with friends or at conferences or whatever. The things that I would talk with other people about that people seem to find interesting. I thought, “Okay, well, I’ve never really written all those down. I’ve written some of them down on my blog, so I’ll just put together some more of those.” And they were already in there. They were really-- you could say, like the tip of my tongue, right. It was right there. It was easy. But there’s another kind of book that can be hard is where if you’re writing a book to explore a subject you don’t know anything about, that can be much harder. So that’s what my next book is going to be. I’m exploring the subject of what I’ve just found out is called pragmatism as a philosophy. But it’s something I don’t really know much about. I only found out, like two weeks ago that there’s a branch of philosophy called pragmatism that matches with something I find fascinating. So now I’m going to go read five books about pragmatism and learn more about it and talk with people about it. And that might take longer. But if the kind of book that you-- especially because you said that you’ve had this in you for a long time. You might just be able to hit record on a voice recorder and just just dump it all out, even have somebody else transcribe it, and then you can just read it back to yourself and you go, “Okay, it’s missing a bit of this, missing a bit, missing a bit of that.” Then you hand it to an editor. You could be done in a week.
Paul
And that would be the dream to get it out there. But I actually really enjoy the sitting down and writing process. I think it’s obviously just an element of there’s that. You talked about identity, there’s the ego when you sit down, it’s like, “You’re not a writer. What the hell are you doing? You’re a personal trainer.” And I can feel that little bit of doubt every time I do it. But I think that doubt is telling you something, Derek. For me, there’s too much word vomit. There’s too much waffle. Your book. Okay. Passively challenges me when I read your work. You’re so succinct. Like I have your book in front of me. I just happen to have it open. You know, even one line, “When you know what you’re doing, you won’t care what anyone else is doing.” You have that on the How to Live chapter about being independent. If that was me, I would have 40,000 extra words in there and I’d be trying to trim through the weeds thinking, why isn’t this coming out? You know, that kind of way. But I actually want to ask you because I’m intrigued. What your understanding, by the way complete segue should I say. What’s your understanding of pragmatism as an actual philosophy? I mean, it’s probably somewhat self-explanatory, but the fact that there’s a book in you suggests that there’s a context to it.
Derek Sivers
This is a big tangent, but I’ve been fascinated for years with this idea of choosing to believe things that are useful not true. So a quick example is just imagine that you go on a daily run in the forest and you start to lose a little motivation after a while. So you start imagining that there’s a pot of gold at the end, and if you get tired halfway through, like just that image in your head helps you get to the end. But then one day you imagine that there’s a tiger right behind you, and like that helps you get to the end much better. So you’re like, okay, are you going to replace the pot of gold with a tiger? So now I’m going to imagine there’s a tiger behind me. This works for me. Then you might imagine that doing this every day is going to lead to greatness, that if you do this every day, you might become one of the best runners in the world. You might end up winning a race. And what would that do for your identity. And even though, like everything in the future is just your imagination anyway, so you can’t say that it’s true, but these different beliefs that you’re adopting change your actions in a very concrete way.
Derek Sivers
And to me, that’s all that matters, is does this improve your actions? So if I believe that I’m really smart, that might give me the confidence to do something that I might ordinarily be scared to do. But it might make me start to feel like a know it all where I don’t learn as well. So if I choose to believe that I’m stupid, I might lose some confidence, but it might make me work harder to learn more if I believe that I’m no good. So somebody could challenge each one of these beliefs and go, “But that’s not true. You’re actually very smart.” Or, “That’s not true, you’re actually very stupid. Or, “That’s not true. There’s not actually a tiger behind you. Don’t do that.” And I’m saying it doesn’t matter what’s true or not. You don’t have to try to debunk anything. It doesn’t matter. All that matters is what works for you. And I choose to adopt beliefs that lead to the actions that I want, because ultimately, that’s all that matters, is the actions. So as I was describing this to somebody who is a philosophy professor, she said, “Oh, you’re talking about pragmatism.” And I went, “Oh, I didn’t know that.” So that’s all.
Paul
And that’s what stemmed your curiosity to even think about writing a book then the idea that somebody just pointed out that this is an actual branch of philosophy, you had no intention of writing a book?
Derek Sivers
Oh, no. No. I’ve been considering writing a book on this subject for a couple of years. I only found out last week it’s called pragmatism. But this idea of useful not true. That’s my shorthand for it. Like, useful not true. Like whatever works for you. I just find it a fascinating subject. That I’ve never heard anybody else talk about. So I feel like learning more about that subject and diving into it.
Paul
Where’s the line, then, between being useful, not necessarily true in your mind and possibly getting you good results, but then maybe not necessarily being a truism for the world and therefore having clash. Like you might choose to believe one thing. It might not be objectively true, and it might clash with the greater context, does that makes sense?
Derek Sivers
Yeah, because that’s why the real idea is like, whatever works for you now, because it may also be that like. Kind of rewinding where we talked about oversimplifying your persona. Situations are way more nuanced than we give them credit for. So this idea of a tiger on your tail might only work for me, but only in this certain situation. And it didn’t work for me yesterday, and it might not work for me tomorrow. But today, on this rainy day, that’s what I needed. And if somebody were to come along and say, “No, you should be running like you’re on hot coals. That is the proper way to run.” I’d think, “Well, says you. Says you for now.” Like, if that works for you, good for you. But for me, for now, I need to imagine the pot of gold or whatever it may be. We’re just using this as a big metaphor. But yeah, I think that we’re all so different and we have different scenarios, and even those scenarios are nuanced. You know, there might be that day that you get up to train that you just saw a Bruce Lee movie last night. And if maybe what gets you to train harder today is imagining Bruce Lee, and you’re just like, “I’m going to be Bruce Lee.” And you start acting like Bruce Lee, and that gives you some kind of like, alter ego boost of energy that you needed today. Or maybe it’s that you woke up this morning and you looked like hell in the mirror, and you just saw this belly, and you’re just like, “I’m going to get rid of that belly.” And it’s like, every day might be different motivation. So again, I just think the questioning whether something is true or not is moot. All that matters is how it works for you. Today. Now.
Paul
No, it’s a very interesting concept, I have to say. It reminds me of say, because I work with people who might have problems with crash dieting. In their mind, the catastrophe has already happened. They haven’t parted yet enough with the identity of crash dieter or yo yo dieter. So they set these really strict rules where they’re walking on eggshells. You know, “I must do that. I must do that.” No flexibility. And then the first thing that interrupts the plan means that they failed. It’s completely broken. It reinforces the identity that they’re a failure, that they’re a bad person, etcetera. And then that belief self fulfills but it stemmed from one thought. So I like what you’re saying in the context of trying to pick up a more useful belief there on how to improve the trajectory of your life going forward by by adopting beliefs that you mightn’t have evidence are true yet, like I’m a successful diet or I’m a successful person, and then start acting in a way that actually fulfills that until maybe it becomes a little bit more autopilot, or until you actually start to believe it and increase your confidence. So I like that idea. I have to say, it sounds like--
Derek Sivers
Part of the reason I feel a little defensive on the subject. Like I have something that needs to be addressed is because I see people debunk good wisdom through like a straw man argument on the author, for example. So you know, let’s just say that there is an author or a media personality who is sharing a lot of wisdom, and maybe you take it in through whatever medium at some point. And you try on this mindset and it works for you. It makes you take better actions. But then somebody says, “Oh, did you hear that person didn’t pay their taxes, or they’re cheating on their wife or whatever.” And they use that to say, “Yeah. So might as well just burn that book. It’s all moot.” Or even Daniel Kahneman wrote this masterpiece of a tome called Thinking Fast and Slow and absolute expert in his field, even a Nobel Prize winner, I think. And a few years after the book was published, somebody tried to repeat some of the experiments he’d done and found that they they couldn’t be repeated. And people want to like burn the book now going, “I might as well throw out that whole book. You know, some of those experiments couldn’t be repeated.” I think well none of that matters. Did the wisdom from that experiment, when applied to your life, did it work for you? And if it did, that’s all that matters here. I don’t understand this idea of trying to treat everything like a mathematical proof where it’s clearly right or wrong. Because especially these things in the field of psychology and philosophy. There’s really no such thing as true. It’s just what works for you. And that’s all that should matter. So I don’t like this idea of trying to debunk authors through attacking them as a persona.
Paul
It’s somewhat contradictory in a sense, because if people are somewhat scientific minded, they respect the kind of the premise of nothing inherently true, just closer to true falsifiability, but to contradict it, then you’re talking there about attacking the character or strawmanning an argument. And arguments are so littered with logical fallacies it’s actually crazy where, well, Derek is wrong because I saw him do this in his personal life and it doesn’t say anything about the merit of the point you’ve just made, about how it might impact the behavior of the people you’re talking to. Because we’re all imperfect humans doing our best in the world. And so I think it’s a big contradiction to the real merit of the scientific mindset.
Derek Sivers
And, hey, you know, you’re a personal trainer. I’m going to use something related to that. Well, in theory, there could be a great personal trainer who’s incredibly unfit themselves, but they give you the right tools and motivation and techniques you use to improve. So for a couple of years I worked with a-- kind of a life coach, and a few people have asked. I mentioned him a couple of times in that book. He’s the one that helped me decide to sell my company. So in the book, Anything You Want, I mentioned him a couple of times. And so some people have asked me like, “So tell me about this life coach, you know, so how did you find him? Because I’m trying to find a really good life coach, but I only want somebody who’s like, as successful as Jeff Bezos, you know, nobody less than that.” And what’s funny is I worked with this guy for a couple of years before I met him in person. We would just have phone calls and I met him in person. He’s five years younger than me and he’s not successful. But it didn’t matter, he was a great coach. And again, so I think like even like a drunk in the gutter can mutter a phrase that can change the way you think for the better. Like where the wisdom comes from doesn’t matter. It could come from something spray painted on a wall or, you know, muttered by somebody right before they kill themselves. But if that wisdom works for you, that’s what really matters. I took that to a bad extreme there. Sorry. That was just-- I was experimenting.
Paul
With the personal trainer example?
Derek Sivers
Yeah. No suicide. Like, why did I have to bring that example in there? I don’t know, it’s just--
Paul
No, I get you. But you are absolutely right. Like my dad, for example, has never picked up a book in his entire life. And then he’ll say these one liners about life and about wisdom and about philosophy. And I’m thinking that is brilliant. And it shapes a lot of my outlook on life, and it shapes who I’ve become. And you couldn’t test the merit of my father’s argument. There would be nothing to test. It’s just wisdom he’s picked up through 70 years of life. So I always think it’s fascinating on the test of the merit of the argument itself and see how it applies to your life and how it works for you, rather than trying to dissect everything and say, “Oh, that’s not theoretically true, and that’s not scientifically provable.”
Derek Sivers
Exactly.
Paul
Yeah. So, I’m going to take it back as well to your goal setting mindset, right. Actually before I do that, when you were working with a life coach, if you don’t mind me asking, what was the catalyst to decide you need a life coach. Were you a bit lost? Were you feeling like you needed a kick in the backside for motivation? Or was it actually to build upon where you were going? The reason I ask is, I suspect, and maybe this is completely flawed logic, that hiring somebody might be at a transition when you’re not so certain you don’t tend to hire people when you’re going really well, or is that not how you see it?
Derek Sivers
No, I was not at all lost. I was just needing more-- I knew in theory what I should be doing, but I wasn’t doing it. I was actually right in the midst of running CD Baby. The business was going really well. I had two things I wanted to get better at programming in the Ruby programming language and I wanted to lose weight. Surprise, surprise. So I really reached out on these two specific missions. I said, “I don’t need any help with the business, but I need help with these two things. Like, I know what I should do, but I don’t know why I’m not doing it.” So we just focused on that. You might like this one. He gave me one tiny little hack that made a big difference. He said, “Okay, so when do you exercise?” And I said, “Well, if it’s a nice day and I’ve finished my work. And I haven’t just eaten. And I’ve slept enough or something like that. Then I go on a run.” And he goes, “Oh, okay.” He said, “Try this. Do you remember those four things you just told me?” I said, “Yeah.” He said, “Okay. Now instead of saying and between them say or.” I went, “Okay.” He said, “Now say it. Say this out loud.” I said, “Okay, I go running when it’s a nice day or I’ve finished my work or I haven’t just eaten or I’ve slept enough.”
Derek Sivers
He said, “Yeah, just try changing those and’s to or’s next time, instead of stacking up a list of criteria that need to happen, just make it so that if any one of those criteria happen, you go exercise.” And that one little change made a big difference for me. I was like, “Oh, that’s really good.” And so like that became a little rule of thumb. I’d just catch myself going like, “Ah, but I haven’t finished my work yet but it’s a nice day, here I go.” I’ll just quickly put on my shoes and go. He also pointed out that if you ask somebody who loves running, “How do you how do you run?’ They’ll say, “Oh, you just put on your shoes and go.” And if you ask somebody who hates running, how do you run? They’re like, “Uh, first you got to get dressed, then you got to put on the first shoe and tie your laces. Then you got to and you got to tie the sack. Then you’ve got to stretch. You’ve got to warm up. You go on a run and then you have to like come back. You have to cool down. You have to get unchanged.” He said, “People who don’t like doing something break it into many awful steps, whereas people who like things have one simple step.” He said, “The things you need to do, you should start thinking of them as one simple step.” And that little hack helped too.
Paul
There’s so much gold in a reframe, any reframe that takes you closer to the identity. It’s what you say about the runner example is fantastic, because often when I’m talking to people who are very rigid dieters and they don’t have the results they want because they’re too busy worrying about every micro decision, they’ll say something like, “I can’t eat this, I can’t eat this, I can’t eat this.” And the day is just littered in what they can’t do. And how exhausting that must be. But when I talk to successful dieters and successful dieters being they don’t actually think about it, ironically, they know they can eat anything they want, but within that permission comes the restraint. It’s like I can, but that’s why I don’t. Because I can always have it any time I want, and I can actually savor it and enjoy it. So similar to what you’re saying about the runner, one is just exhausted thinking about it, and then the other person gets a bit, this is just what you do. Because you’ve obviously said you wanted to lose a little bit of weight, I’d be intrigued to hear your experience. If you’re comfortable to share, if you’re comfortable to talk about it.
Paul
Well, it’s more so that I’m always interested that the information is is there, but I consider it more behavioral. Unless you want to engage in the process itself for life, it’s going to be very difficult. You’re going to be battling yourself. I don’t even need to hear about the process of the weight loss itself, but more what was your come to Jesus moment? Yeah.
Derek Sivers
Twice in my life I’ve lost weight very deliberately and successfully. Both times I just bumped it up my values hierarchy in a way that the night before something is due, it’s suddenly the most important thing. You know, we all know that sense of changing our priorities, right? Like something that was fourth, fifth, sixth priority, “Oh my God, it needs to be done tonight or I won’t be able to fly to Japan tomorrow on my trip. I have to get this passport thing sorted. Oh my God, I’ve been putting it off.” Suddenly it’s first priority, right. So twice in my life that’s happened with my weight in particular. Yeah, there are different times that I got into weightlifting and strength training or running and stuff like that, but specifically like losing weight. There was just twice in my life that I was like, “All right, this is now my top priority.” One was when I was living in London and I was going to have a custom tailored suit, so I was like, I definitely want to lose weight before I get very accurately measured for a custom fitting suit. So that was once. And the other was when I was dating a professional acrobat who, you know, every little half kilo counts on an acrobat. And she just got me into this mindset. And because, you know, we were we were dating, we were physical. And that woman was built like an iron bar. That just inspired me. I was like, “Okay, this is now my top priority.” So that was it. It’s like the techniques didn’t even matter because once you’ve made it your top priority, everything else just falls into place, you know, just eat less. I would go on long walks for two hours a day and voila. People went, “Oh my God, you lost so much weight.” I’m going, “Oh did I? Oh yeah. Whatever.”
Paul
That’s why I asked you. I knew you wouldn’t go to the place where you said immediately, you know, change my nutrition and change my activity, because you probably always knew that.
Derek Sivers
Everybody knows exactly. Everybody knows what you’re supposed to do. It’s just a matter of making it your priority.
Paul
And that’s why I asked you, in a sense. Because, I mean, do you have advice? Or is it the kind of thing you don’t dare to touch on, on how to increase, say, an active lifestyle or any important goal up the values hierarchy? For me, for example, I’ve set a writing habit, so I set off a block of time in the morning. Not rigid. There’s just in the morning. I sit with my computer and I write about what comes to mind. It’s a very loose system, but it’s been working for me so far, and I’m really looking back, cringing at the first ten articles I wrote a hundred articles ago. So that’s a good sign, I think. But in terms of bumping something up a value hierarchy, how do you advise other people to go about it, or do you consider it something that can’t be advised? It just happens when you’re ready?
Derek Sivers
Yeah, I think it just happens when you’re ready. Or rather, maybe there’s just nothing more to say about it. At a certain point in your life, you just decide this is what’s most important. Kind of like those people. I just got an email yesterday from a stranger who had some kind of death scare. Like, I forget what they had, like some kind of crazy cancer, leukemia or something that they they actually beat it. They battled it. They did the chemotherapy or whatever. It’s actually gone. But they said, wow, did that change my life for the better. They said like, my life is definitely like before and after the cancer. Like that changed everything for me because somebody who’s gone through that suddenly is going to put healthy eating and healthy living and say like a maybe a peace of mind with how they spend their time, not wasting time on celebrity gossip, for example. Because an event like that changes your priorities, changes your values hierarchy. Maybe priority is the better way to put it changes your priorities. But it could be anything. You don’t have to get cancer. It can be wanting to fit into your wedding dress. It can be wanting to get ready for a photoshoot you booked in three months, or whatever it may be. It’s just doing it.
Paul
I was at a party recently, and a friend of mine who overcame a life threatening illness overheard another couple of my friends debating something very-- it was weird. It was political, and they were coming at it from such different angles, but they almost concluded the same thing, if that makes any sense. People are more aligned than they realize. Maybe if they don’t express that, they are in a sense, but they are debating something. I think that Jordan Peterson said, and how inflammatory it was. And my friend who had just had that scare and has come out the right end, just went, “Lads, trust me, that doesn’t matter. Trust me, you’ll realize how much time you’re wasting on stupid crap when you’re ready. But forget about it. That doesn’t matter.” And it’s fascinating because the two people I know in my immediate friend’s circle who have either beaten cancer or a life threatening disease, have both come back with this real sense of what truly matters in life. There’s a calmness, there’s a purpose, there’s a peace. Even daily coffee seems to represent more to them than the crap that we worry about when we’re not faced with our own mortality every day. You know, that kind of way. So I just thought that was--
Derek Sivers
You know what’s funny, the money stuff that we talked about at the beginning of the call. That was like that too, in the way that you might pity somebody who spends a lot of time on watching a soap opera and getting really into it. You’d think, “God, you’re just wasting your life. You could be doing so much more.” I feel that with a lot of rich people who get really into buying things, they get this huge home full of crap with so much stuff. And look at my home theater and they pull down the this and the this with the projector and the big surround speakers with the bar underneath with the subwoofer and that and oh, let me take you out on my boat and, you know, check out this or I only fly private now and I’ve met a few of these people and I have that same feeling as people who, you know, waste their lives in front of soap operas. I think, “God, you’re you’re putting so much of your life energy on this stuff, it’s just ridiculous. And it just doesn’t matter.” It’s just it’s sad.
Paul
I totally agree, I think you touch on that in your book, too, because I told you I highlighted some things because I want to come back to them and sit with them. But the idea of the more luxurious your life becomes, the more you lose the joy in those things and then the little things. So therefore you’re just adapting yourself to a more shit existence.
Derek Sivers
Yeah, yeah. The hedonic treadmill, the adapting to your comfort. Yeah. God, there’s this beautiful moment in the book Stumbling on Happiness by Daniel Gilbert, where he explains, he said, “Try to imagine the moment where you have a pair of sunglasses, for example, but you see a better pair that you really want.” And he said, “In that moment, the happiness is coming from the comparison, the sunglasses in your hand versus the new ones. You compare them and you think, ’Oh, these new ones are better.’ So you spend the money, you buy them, you put on the new ones and for a brief moment you go, ’Ah, I love my new sunglasses.’” And he said, “Well, guess what? In a couple days, those are just your sunglasses. Those aren’t the new ones anymore. Those are just your sunglasses. There’s no more comparative moment. And what we’ve found, it’s the comparative moment that gives you joy.” Then you just become acclimated to them. Yeah, these are my sunglasses. Whatever. And so we go looking for a new thing to upgrade or replace in our lives. But I think once you have had that explained to you. I’m so glad that I read that book a year before I sold CD Baby. It was probably a big influence on me giving away the money, was realizing, like I had just read Stumbling on Happiness, and I just knew that what am I going to do, buy a Ferrari. It’s stupid, a mansion? What do I need six rooms for? I’m just me. I don’t have six kids, so yeah. Sorry. I forget how--
Paul
No, I love it. I love it because that’s the mindset I absolutely aspire to. As my business started to go a little bit better, one of the things I was grateful for as I observed my own behavior was like, “Oh my.” Like I’ve gone from nothing and starting at zero to having a business now that sustains my lifestyle and, you know, in a good way. And I want for nothing and I want very little. Now, I’m lucky because my parents have always drilled that value into me. So I’d love to pretend this is some wisdom I’ve acquired. It’s not at all. It’s my parents giving it down, but it’s something that I’m grateful that I haven’t had to learn the hard way. I haven’t had to be the cliche, self-employed person who buys the shiny car to impress, to realize that’s not how you get your happiness. Did you do anything frivolous that you look back and think, “Oh my God, what a jerk!”
Derek Sivers
No. Let me think.
Paul
I mean, the fact you think is a great sign.
Derek Sivers
No. I don’t think so. There were a couple of things that were like-- actually, those of you watching the video. I’m in a recording booth right now and this was a bit of an indulgence. So is this microphone. This is a really nice microphone and a really nice recording booth, a soundproof recording booth, so that even if my neighbor is building a new deck on her house, I could record my audiobooks. That was really important to me because as I started to record my audiobooks, there was this neighbor that seemed to just mow his lawn every day for four hours, or if it was a dog barking, suddenly I felt like, “Well, fuck me, I can’t record my audiobook today because the neighbor’s dog is barking.” And so I looked at the price of going into a recording studio, and it just turned out to be the same price as just buying a recording booth. So it was expensive. I think it was like. €10,000 and I think this mic was like 3000. Those are probably the two of the biggest indulgences in my life. This recording booth and microphone. But I can justify it because it’s for my audio book, so I don’t feel like too guilty about it. So no, I don’t think I’ve ever done anything stupid with money.
Paul
Man, that sounds like a proper investment. Which is actually a nice segue way onto the book. I’ve obviously touched on it while we’ve been talking. I mentioned before we started recording how much I enjoyed the book “How to Live”. Obviously I highly recommend it, I loved it. I’m not just saying that because I’m on the air talking to you. As soon as I picked it up, I said to my girlfriend, going, “I can’t put this book down.” What was the motivation for it? Where did you get the idea? It’s a very intriguing concept if you want to share with listeners.
Derek Sivers
Did you see on the opening page it says, This is an homage to the book Sum by David Eagleman.”
Paul
Possibly not, because I skip everything and always go straight, straight in.
Derek Sivers
Okay. So yeah, the first page, it says that this book is a straight up homage to another book. So there is a book called Sum spelled s-u-m by David Eagleman that is one of my favorite books of all time because of the format. The subtitle is “40 Tales from the afterlives” and it’s 40 little short stories, like just 2 or 3 pages long each about what happens when you die. But what I love is that it sounds like it was written by 40 different authors, because every story is completely different, yet it’s all answering the same question. So it’s like the book asks what happens when you die? And one chapter says, “When you die, you get to turn into any other creature. So you choose to be a horse.” And such and such. And another chapter says, “When you die, you find out that you were an artificial intelligence program.” And another chapter says, “When you die, you sit in a waiting room forever until the last person that knows your name is gone. And what a curse this is for people who have a statue made of them, because they have to sit in this waiting room for hundreds of years.” And there’s so many brilliant ideas in this. But I love the format of how every chapter disagrees with the rest. And probably like you, like any of us listening to this podcast, I’ve heard a lot of different people with a lot of different answers on how they think we should live.
Derek Sivers
They think that we should have atomic habits, or they think that we should do everything in four hours a week, or they think that we need the subtle art of not giving a fuck. Or, you know, we need to imitate the Stoics, you know, there’s like all these different approaches to life and they all disagree with each other. But yet we read all of these books and we glean bits of wisdom. And I thought, “Oh, wouldn’t it be fun to do it like the book Sum and put them all into one.” So every chapter disagrees with the rest. And it was also a way for me to put everything I’ve learned in my life into one book. So I put all of my thoughts on living independently and why you should into a chapter called, you know, “Be Independent”. But then all of my thoughts on why we should commit to a person, to a place, to a career, to a path. And into the next chapter called “Commit”. And those chapters completely contradict each other. But they’re all true, and we’re just not used to seeing one book deliberately contradict itself. So then the challenge was like, how do I end this thing? And you will see the the subtitle of the book is “27 Conflicting Answers and One Weird conclusion”. So I came to a very satisfying, weird conclusion at the end that you will see I guess.
Paul
So I’ve seen, but it’s a skill definitely in the book that you’d make a point about living independently. And obviously that’s my chosen field, nomadic lifestyle. So I’m like, “Yeah, confirmation bias, this is what I want.” And then you make an equally compelling argument about, you know, stability and career and stuff like that. And both arguments carry with it their merit. And you’re right, it’s not often you see a book presented in such a way where two conflicting arguments can be presented with the same calm, rational, compelling, thought provoking oomph, we’ll call it with the same oomph.
Derek Sivers
I haven’t heard that word ever in a long time. Yeah, it was fun writing it because I would get convinced with every chapter that, in fact, this was the one. You know, that every chapter I was writing, I was like, you know what? I know I have these 26 other chapters in here, but really, this is the one, this is the way we really should be living. And then I’d get to the next chapter. I’m like, “Yeah, no, never mind. This is it. I mean, God, this really is how to live.” With every chapter I felt that it was the one and that’s what I was aiming for. I wanted that the reader to have that feeling, too.
Paul
Yeah, absolutely. Obviously when you’re writing, it’s going to be a reflection of what’s stored in you. What has been some of the more enjoyable experiences in your life? Have you traveled a lot? Have you learned languages? What particular cultures have you enjoyed? Know it’s a bit of a loaded question, but it’s the kind of thing that genuinely intrigues me about people. I’m currently learning two languages myself as well, so it’s a bit fresh for me.
Paul
Well, I’m I was living in Spain for one year, so I got my Spanish to a decent level. I even was on a podcast in Spanish. And as soon as I got the email, will you do it? I thought, “Oh, now there’s no hiding place.” And I started learning Portuguese.
Derek Sivers
What are you learning right now?
Derek Sivers
Portuguese?
Paul
Yeah. Do you speak it.
Derek Sivers
A little bit? Were you in Portugal?
Paul
No, but I’m after Ho Chi Minh. I’ve been looking into potentially moving to Lisbon, so I started picking up a little bit of Portuguese as well, because I think there’s nothing more, I guess, attractive than going to a country and not assuming that they’re going to speak my language. Now, I can’t do that with every country I go to obviously, I’m in Vietnam, although I took ten Vietnamese lessons, I’m still not very good.
Derek Sivers
I’m flying to Japan tonight.
Paul
Are you?
Derek Sivers
Yeah.
Paul
That’s a good list.
Derek Sivers
They just opened yesterday.
Paul
So I heard. My girlfriend came straight in and said, “Babe, they opened Japan.” So now we’re deciding what to do between here and Christmas.
Derek Sivers
Portuguese. My tip, by the way, two things for you. Especially for Portugal Portuguese. European Portuguese. Look up the Michel Thomas method. It’s spelled M-i-c-h-e-l Thomas. The Michel Thomas Portuguese is the best gentle introduction to European Portuguese there is. It’s a British woman who just talks you through how the language works. It’s very gentle. It doesn’t just come straight at you and start dumping vocabulary words. It teaches you how the grammar works, how the language is put together, knowing that you’ll fill in the vocabulary later. So Vocabulario. So yeah, check out the Michel Thomas method. Michel Thomas Portuguese. And then there is a great website called practiceportuguese.com. And it’s run by two-- well, it’s a native Portuguese person and a Canadian that moved there and the two of them together host this website podcast audio course called practiceportuguese.com. That is so good because they know you’re learning. So they they’ll do things like read the news, like an article in today’s news. He’ll read it very slowly and clearly the first time in Portuguese. And then the second time he will read it again. Still, you know, clearly, but now not slowly, you know, and it really helps you, like, ease into it. Anyway, those guys are great. I highly recommend those two resources for learning Portuguese. I didn’t ever get fluent. I was going to move there. I started to move there. We lived there for one month, put my son into a school and then things happened and we chose to live in Oxford, England instead. So I didn’t live in Portugal after all. But that’s why I know these things.
Paul
What’s your comprehension like? Could you have a conversation if you went back?
Derek Sivers
No, no, no, I only really got like a couple months into it and then yeah, life threw me astray. And then Covid hit and sent me back to New Zealand, so. Oh well, yeah. I was a legal resident of Portugal until a few months ago, and in fact I would have been eligible for citizenship this year. But New Zealand closed their borders, so I couldn’t go back to Portugal to renew my visa, which is fine, I mean, whatever. So to answer your question though, I think travel can open your mind a bit, but I think that moving to a place and feeling at home there can change you a lot. I think it changes your sense of self-identity. I think you have to stop thinking in terms of them. You don’t think of the people here as them. You start to think of them as us and you start to say things like, “How do we tip here? How do we rent a motorbike?” And you just start to feel like, okay, you’re new here, but this is us. You belong here now. You live here now. They might have got here first, but you know, you are included in this category now. This is your home. And to really internalize everything is home, I think does amazing things for your self identity and lets you expand the way that you see things instead of feeling like the way you grew up with is right. And the way they do it here is weird. Instead, you just have to adopt it and take it on.
Paul
Oh, that’s so true, Derek. Even when I got to Ho Chi Minh, what three years ago, at this stage, I remember, like, I was so excited. But then you see the street food carts and you start to think, “Oh, we’re so much more hygienic back in Ireland.” And you have these immediate, conflicting thoughts, but you’re so right, the more you immerse yourself in the culture. Change it from a they to a we. And even I don’t know if you agree with this, represent your country with the values that you wish your country was seen more of to a degree as well, so that people think, “Oh, I met an Irish guy in Ho Chi Minh. Irish people seem friendly and welcoming and nice. And despite what the stereotype is, not drunk all the time.”
Derek Sivers
Right, I like that, yeah.
Paul
Yeah. So I’m with you 100%, I think moving to a place it certainly, in my experience is it changes you in a way I don’t think you could have changed had you stayed at home the whole time.
Derek Sivers
Yeah I agree, a Swedish friend taught me, I should say a Swedish friend in Singapore taught me an Icelandic word heimskr, h-e-i-m-s-k-r means idiot in Icelandic, but the literal translation of heimskr is one who has never traveled abroad.
Paul
Oh. That’s going to be a good one for me to know. What brings you to Japan? Is it just leisure and visiting?
Derek Sivers
Yeah, I’ve been to Japan five times. I used to play guitar for a Japanese pop star when I was 22 years old. But I have a ten year old boy who has never been to Japan and has been wanting to go for years. And so I promised him a couple of years ago. I said, “As soon as Covid is over, as soon as Japan opens their borders, we’ll go.” And literally last night I said, “I wonder when Japan is going to open.” I said, “Oh my God, they just opened today. Wow, 11th of October, Japan’s open.” I was like, “Huh, I wonder what flights cost?” I was like, “Oh my God, there’s a really cheap $700 round trip from New Zealand if we leave tomorrow night.” And so yeah, I asked his mom. She said, “Yeah, I’m really busy with work. Go.” So just me and my boy are going to Japan for two weeks tonight.
Paul
You don’t waste time because--
Derek Sivers
Well, to me, those are the best vacations, are going now because it always sucks when you like plan a vacation like five months in advance, you know? And then by the time five months comes around, you could be on to a whole new project doing something else. You could not be in the mood. You could be head down on your work like, “I don’t want to go. I want to keep working. Damn it. I scheduled this thing five months ago.” No, to me, the best vacations you go now when you’re in the mood to go. And now it’s just right. School holidays here in New Zealand. Perfect weather. Yeah. Time to go.
Paul
Yeah. I’ve heard nothing but good things about Japan. It’s been something that I’ve been dying to see. That’s why I’m back in Asia now. Had been living here for a few years, went home to Europe, and now we’re back here again and seeing Japan and other parts of Asia in a post Covid world, especially since it dented so many of our travel plans. I’m just so excited to see it. I’ve only ever heard wonderful things about Japan.
Derek Sivers
It is such a different world from Vietnam. I did it the opposite way around. I went to Japan like four times and then went to Vietnam. I was like, “Whoa, is this different. I thought I knew Asia.” No, like Vietnam and Japan are as different as you know, I don’t know, I was going to say as different as what Finland and Greece. Yeah. They may be kind of near each other, but man, they’re different.
Paul
The traffic and the culture and everything here is just so crazy. But absolutely, it’s madness. Look, dude, I appreciate your time. I am going to end up wrapping up soon, but I appreciate it. The book “How to Live” and your other books, I’ve read two of your books, Anything You Want and How to Live. I’m sure you’ve other books, which I haven’t actually gotten around to yet, but, thoroughly enjoyed them and I highly recommend them, dude. And look, I really appreciate your time today. Enjoyed conversing with you. I wanted to very much pick the brain of an author somebody who’s--. It’s your thought process I admire. I said it to you before, when I look at people and obviously imposter syndrome sets in where you have the I know all my own foibles from the inside, and I don’t know anybody from the inside. But the way, the way you pick ideas apart and the way you can put them onto paper, it’s something I very much aspire to. So I just want to put that out there and say, I appreciate your work, because it certainly gets me thinking in a very different way to how I would naturally think in terms of content distribution. So thank you for that.
Derek Sivers
And hey, for what it’s worth, like I said earlier though, that like every sentence there was like that came after deleting like ten paragraphs. So the process like the rough drafts are always just a bunch of nonsense. And then after you’ve blathered enough onto the page, then you just think, “Okay, what’s necessary, I’ve got a whole page of blather here, which are the core sentences that really represent all of this blather, or what’s the most interesting idea in this whole page.” And then you just publish that idea and leave out the blather. You save it for a conversation like this.
Paul
Do you really find that is the case? Do you trim away that much work in your own work? I mean.
Derek Sivers
Oh yeah. Yeah. In fact what I generally tend to do is I pour all my thoughts onto a page, I’ll write for hours, and then after a while I’m just sick of what a mess it is. And I almost always do this thing where I go to the top of the page and I say, okay, I need to write an outline. Like, what’s the real point I’m trying to say here? And I put it like, you know, a little outline, bullet format. And that I often end up just basically posting the outline. I say like, like really these are the eight sentences that get to the point of these, you know, five pages below these eight sentences summarize it. And so I’ll just post those eight sentences. It makes me sound profound.
Paul
Yeah, that’s for sure, because I’ve noticed that the closer you get to wisdom, the less you seem to have to say. And it seems to be a writing truism as well. Well, look. Thanks, man. I really appreciate your time today. Especially appreciate the book. Appreciate the wisdom. So thank you for that.
Derek Sivers
Yeah. And anybody listening to this go to my website and send me an email. Say hello.
Paul
Oh one thing before you go. I did mean to ask you and I was going to ask you, but I didn’t want to bore you with more questions. You’ve definitely been asked before from earlier on in the show, but when you did Ferriss, am I right in saying you got like 8-9000 emails the next day because you hadn’t prepared for how famous the whole situation would--
Derek Sivers
I’ve known Tim for a long time. I didn’t know his podcast was that famous. I was doing it as a favor to him. I was like, “All right, Tim, you’ve asked like five times. Fine, I’ll come on your little podcast.” I had no idea how famous it was. And so, yeah, I gave my email address on the show and in the end, I got 60,000 emails over the next few months, and I answered every single one of them.
Paul
Wow. Well, that is commitment. I’m not even anywhere near as busy as that, and I struggle to stay on top of emails.
Derek Sivers
It was worth it. I mean, in fact, like two of those emails became future girlfriends and three of them became future best friends. And, you know, I met some really interesting people in that big batch of emails. So it was worth it.
Paul
Yeah. You always seem very open to just everything, even the way you speak about people that contact you. You always just seem open to new things. I’ve heard you say before.
Derek Sivers
It’s so interesting. I mean, you know, even you and I talking right now, it’s because you emailed me out of the blue and I just checked out what you’re doing. I was like, “Wow, you’re really cool, dude. I really like what you’re doing. And how cool are you living in Ho Chi Minh City. Wow.” And I love that, you know, I’m sure there would be some people that I wouldn’t find as interesting. You know, a middle manager somewhere near Chicago, near where I grew up probably wouldn’t be as interesting to me as a guy who makes guitar pedals in Slovenia or a blacksmith in Austria or something like that. Yeah, I really like meeting the huge variety of people that email me out of the blue. So yeah, everybody send me an email, say hello.
Paul
Before I let you go. And I promise this is my last before I let you go. I’ve heard you say something before because I tend to share the same philosophy as you, in the sense that friendship involves that element of emotional safety. So when you’re when you get people reach out to you, is that an energy that you just feel through, through a text? Is it something that you are curious about initially and then you feel it as the relationship expands? Because I’m very like you, I pick up on the energy of safety and I mean can I say something really stupid and you not judge me as a stupid person?
Derek Sivers
Well, that’s a good friend. I love that thing where you can be completely vulnerable with your friends. Yeah, actually when Tim Ferriss and I first met, we like instantly we were like, “Oh my God, you’re like me.” You know, he had done The 4-Hour Work Week, but he wasn’t quite as famous yet. And we just realized we were like so similar and within like a couple of weeks, I think like he had to break up with a girlfriend. He’s like, “Dude, can you come over?” He said, “Let’s get a little drunk. I’m really bummed out.” And then sure enough, like a couple of months later, I was breaking up with my girlfriend. I was like, “Dude, I need you to babysit me. I’ve got to sit around and wait three hours for her to get home from work so we can have the breakup conversation.” And it’s really nice to to be vulnerable with somebody, have that level of trust where you can just kind of let your guard down. But yeah, but by email, I mean it’s mostly a different thing.
Derek Sivers
Mostly people just email. They tell me a little something about themselves. Usually they’ve like read my book. So they’ve just had my words in their head for a few hours. So now it’s kind of a reciprocal, like, “Hey, well, you’ve just shared yourself with me, so I’m going to share myself with you.” Yeah. I’m going to meet some people in Japan tomorrow, I mean, this week that I have never met in person, that I’ve emailed. And yeah, a couple of years ago, when I suddenly decided on a whim to go to Helsinki, Finland, I rang up the 12 people I know in Helsinki that had emailed me in the past. We met up and you know, a day later I’m sitting naked in some sauna with a Finnish guy that had emailed me a few months before and it’s really cool to just know people around the world, and you can never tell who’s going to turn into a friend, but usually it’s just kind of nice to have these loose connections and know that you’re in touch with somebody.
Paul
I love that man. I think it makes such a difference to be so open, and you never know what the universe is going to throw your way then. Well, appreciate it, man. I hope you have an absolute blast in Japan.
Derek Sivers
Thanks.