Derek Sivers

Seekers Mindtalks

host: Akshay Raj

musical career, self-help, concepts of truth, nature, worldview, mastery

episode web page

listen: (download)

watch: (download)

Transcript:

Raj

Your whole life. You’ve switched careers. You’ve skipped so many dogmas. You challenged a lot of things. And I feel in that sense, your psychology is a whole lot different. Tell us about your story, man, from the start to where you’re at right now.

Derek Sivers

Sure. And by the way, audience, Raj and I started talking about India, and then we realized that we, you know, it was time to begin recording. So we can kind of carry on. My background is, I was really just an American kid that wanted to be a musician when I was 14 years old. I just loved playing heavy metal guitar, and I just decided, this is what I want. I want to be a musician. So I think if some things seem weird about me, it’s because I formed my worldview based on who I needed to be to be a successful musician. So for example, there’s a precedent in music for always pushing forward and not doing what other people are doing, right. If you’re an artist and you want to make a name for yourself, you don’t imitate what everybody else is doing. You find a way to have a new sound, to do something different. And so conformity has never been a problem for me. Because from the early years, I was always trying to find a way to do things differently. There’s also another precedent in music that great musicians tend to push forward and not repeat their past. So if you look at careers of musicians from Stravinsky to David Bowie to Miles Davis, they will have a period where they did one kind of music and they get well known for it, and then they leave it behind and they push themselves to do something different. And they do that for a while. They get known for it, and then they leave it behind and they push themselves to do something different. So I think I’ve made career decisions based on these initial archetypes of my early role models as a musician.

Raj

Why is the rest of the world different from that sort of thinking?

Derek Sivers

Oh, because they don’t want to be musicians. I don’t know. We’re all just influenced by the worldview that our parents give us at first, and the worldview that our friends echo back at us. We’re kind of like bats. Bats use echolocation, right? I think from what I understand, they don’t see very well. So they put out sounds, and then they hear the sounds echoing back from around them to know their location. And I think humans do that too. We’re social, we talk to people and our friends echo back opinions and worldviews to us, and then we shape our view of the world based on that. Our parents and our friends and the media, what we see in movies and song lyrics and whatnot, tell us how things are.

Raj

But you’re different and but you’re still social, right?

Derek Sivers

Well, I surrounded myself with different people than most. So from the age of 14, I was just like, absolutely focused to be a successful musician. I wasn’t trying to make money. I wasn’t trying to go to college. I wasn’t trying to pursue anything that most teenagers my age were. I was just completely focused on this one single goal. And then I went to an all music school. I didn’t go to a regular university. I went to Berklee College of Music. So I did nothing but music from the age of 14 to 29. Even the only job I had at the time, I joined a circus at the age of 18. So then the people around me were like magicians and jugglers and performers like that. So, again, we were a weird bunch. These are the people that I was surrounded by. And I moved to New York City. I got into the music business, these were my role models. And at the same time, I was reading a lot of self-help books because I thought understanding these books will help me get to where I want to be. So I was very influenced by the thoughts of people like Dale Carnegie, Tony Robbins, and whatever I could get my hands on.

Raj

On the one side, you were exposed to all these artists and other side, you had this nonfiction that you were feeding yourself.

Derek Sivers

Well, they’re very similar. Both are very self driven.

Raj

Interesting.

Derek Sivers

Both self-help books and artists are making their own way in the world. They’re not trying to impress a boss. It’s about self-reliance. Artists are self-reliant. Artists are their own boss. It was alienating for me after I sold my company, and people treated me like an entrepreneur, I was constantly asked this question, “How did you get the courage to quit your job and do a business?” And I just kind of went, “I never had a job. I never I’ve never had insurance. I’ve never had a paycheck. I’ve never had a boss. I don’t understand the question. I can’t relate to this idea of getting the courage to quit your job.” You know what I mean? That was just not where I came from.

Raj

Because that’s that’s a different perspective. What I think is, like nonfiction or self-help. Sometimes it acts in your head as kind of rules or guidelines for your life. Whereas an artist, they think more freely, they are not subjected to boundaries. But still you say they’re the same that’s why I was intrigued.

Derek Sivers

Give your ears to anyone but your mind to no one. Even when reading self-help books, I just took it as tools, recipes. You can open a cookbook and get inspiration, but it doesn’t mean the cookbook is now your boss. I don’t think of it as rules. Maybe the cookbook is the wrong metaphor. The toolbox is the better one. Yeah. It’s like going to the tool shop, right? To look at some different tools and go, “Hmm, maybe I could use that. Yeah. Okay, I’m going to get this tool. I’m going to use this tool.” It’s not a rule. I never thought of it as something I had to do. It was just other builders of their own life were sharing with me the tools that they had used for building, and I was using their tools. If I wanted to.

Raj

Right, right. Like I was reading on your website, the books that you read. And I came across this book, “The Listening Book” forgot the author’s name. And it kind of resonates the same kind of philosophy, I guess. Right? Like, talk to me more about The Listening Book.

Derek Sivers

Well, for one, it’s beautifully written. It’s hard for me to read books that are poorly written, even if they have a good message. It’s such a struggle.

Derek Sivers

It’s like listening to somebody with a really bad voice. You can listen really hard and maybe hear what they’re saying, but man, it’s hard.

Derek Sivers

So when a book is poorly written, it’s like, ah, I’m struggling through this writing. I’m trying to hear what you’re saying, but “The Listening Book” is beautifully written and it calls your attention to sounds around you. The author is a musician, and sorry, I don’t remember it very well off the top of my head. I’ve read it many times and loved it. But it’s not at the top of my head.

Raj

When I read it, what it showed was that it’s sort of a meditative like practice. Instead of visually looking at the world, you slowly look at what’s happening. So you are more grounded, basically. That’s what I got.

Derek Sivers

You know, I’ve been wondering about the effect that being in nature in New Zealand has on my lack of conventional thinking. I remember during the 2016 US elections, all of my friends were screaming with rage and upset about the presidential election where Trump versus Clinton, Hillary Clinton and screaming about just the urgency of the media message, or the shocking horror of the day or whatever it was. And I was here in New Zealand with a young child, almost a baby. He was kind of a baby still, and we were just spending all of our time in the forest or down at the beach or in the park, in the grass and the playground. And my life was very physical and real. I was not spending a lot of time looking at a screen or paying any attention to the media, and it felt like a huge gap between the real world, where waves are crashing on rocks and wind is blowing in the trees. And this is what’s real. And the media world, which is the product of minds and commercial interests are both amplifying each other to kind of scream that their worldview is true and right. And you must be upset about this, and you need to be angry about this, and you should pay attention to this. And I just thought, well, none of that’s real. It’s just in people’s minds. Thoughts aren’t real. Thoughts are just passing imagination things. So that to me made a huge distinction. I’ve been living in New Zealand for 12 years now, and I think spending a lot of time in the natural world helps remind you the difference between what’s actually real and what’s just in people’s heads.

Raj

Yeah, I was reading your blog post and I saw the recent one about the Harry Potter mirror. Right?

Derek Sivers

Yeah.

Raj

Talk to me about that. Let’s talk about that. Do you remember?

Derek Sivers

Sure. The idea is in Harry Potter, there’s the mirror that shows people their deepest desires. And so when Harry Potter looks in it, he sees his parents. Dumbledore sees his old friend Ron sees himself as the captain of the Quidditch team. But they don’t argue about what’s in the mirror because they know the deal. They know this is a magic mirror that’s showing them what they need to see. So I said, “Imagine if there was something like that that shows us what we need to believe in order to be who we want to be or do what we want to do in life.” And so somebody that maybe has a terminal illness and knows they’re going to die soon would look in that glass and they would see proof that there is a beautiful afterlife waiting for them, and all their loved ones are going to greet them on the other side of death. That person might or should find great tranquility and comfort from that idea. But somebody else would look in the mirror and see something completely different. You know, there are some people that are out to challenge death right now, saying like Aubrey de Grey saying, if we do science right, maybe we’d never need to die. So he would see something very different in that looking glass. But the problem is that people argue about their worldview. Somebody says, “This is true.” And somebody else says, “No, no, no, that’s false, and this is true.” And then the two of them fight. But I think they’re just comparing thoughts in their head saying, “But that’s not what I need to believe. Yeah, well, this is what I need to believe. Yeah, but that’s not what I need to believe.” But they’re arguing, saying it’s real. Whereas I think it would be better if everybody understood that we believe what we need to believe.

Raj

We all need different things, right?

Derek Sivers

Yeah.

Raj

We all need the different things coming to let’s come to your book now “Useful Not True”. Is it out yet?

Derek Sivers

No, I’m still writing it. No, I’m still--

Raj

Talk about that.

Derek Sivers

Yeah, I’m still 80% done. Sure, but no, I’m still writing it. In fact, I was writing it up until five minutes before we hit record, and I’ll go back to writing it five minutes after we hit stop.

Raj

What’s the whole idea behind that?

Derek Sivers

I should get ready to think of a succinct way to say it. The big idea is, almost nothing people say is true. Basically nothing you think, your thoughts are not true and ideas themself are never true. But they are can be useful. So you should judge ideas not by whether they’re true or not, but whether they’re useful to you. Because ideas create emotions in you and emotions are what create action in you. Motivation is driven by emotion, so you should choose ideas based on how they affect your emotions. For the real point of taking action. Action is what it’s all about. All that really matters is action, and the whole point of ideas is to affect your actions for the better. That’s the core of the book. And then lastly, once you stop thinking of so many things as necessarily true. Then you can detach the frame so that you can reframe. And then you can think of many.

Derek Sivers

Yeah. You live in Toronto. Somebody would say it’s a great place to live, and therefore you should stay there. And if you get a job opportunity in Iowa, somebody would say, “Oh, you should not take that. Iowa is boring, Toronto is exciting.” And you might hold that up as just true.

Raj

Can you give an example?

Derek Sivers

Like, yeah, that’s true. Iowa is boring and Toronto is exciting. But you need to challenge it. You need to find out when you’re thinking of something is just a true fact versus something that’s in your head. And judging a place as boring or exciting that’s just in your head. That’s not true. Somebody else could feel the exact opposite and think that Iowa is exciting in Toronto is boring, so you need to detach from thinking of things as true. The problem with true is when you think of something as true, you stop questioning it. It’s done. It’s that’s that and that’s a fact. It’s just true. Your brain doesn’t question it anymore. As soon as you think of something as not necessarily true. Now it invites you to challenge it. It’s not necessarily true. Therefore, how else could I think of this? What would be another viewpoint? How else could I think about this? What’s another perspective? And then you can open it up, because now you can just brainstorm and keep coming up with different ways to think about it until you find one that works for you. And by works for you, I mean one that affects your actions for the better.

Derek Sivers

Because in the end, all that really matters are your actions. Unless all you’re seeking is to feel tranquility about the past. So in fact, I’ll give a better example instead of saying Toronto versus Iowa. Maybe you feel that there’s somebody in your past that wronged you, that you’re still angry at somebody in your past for what they did to you, “That evil bastard can’t believe he did that to me.” And you’re still mad. But if you think, “Okay, wait, that’s not necessarily true, that he wronged me, how else could I think about it?” You might come up with 1 or 2 other ways, but then don’t stop there. Come up with like 10 or 20 different ways to think about it, and eventually you’ll find one that might give you the inner peace, the tranquility to feel, “Actually, you know, it’s fine. I’m actually glad that that happened. I didn’t want to be there anyway. I’m glad that’s done. Yeah, I actually feel totally okay about it now.” And that’s what you had to do. Maybe that was perspective number 17 that made you finally feel that what happened in the past was actually okay, and you’re no longer mad about it and that can be enough.

Raj

So we should be deeply looking into our natural intuitions that pop up when we are subjected to conditions.

Derek Sivers

Your natural intuitions are an obstacle. You should not honor them like an Indian first born son. You should have low regard for your intuition. Your first thought is an obstacle. You need to get past it. Your second and third thoughts are a start, and ideally those are the starting point to then come up with many other ways of looking at something. So like a toolbox, you have more tools to choose from and you can choose a better way think.

Raj

I think that is a big obstacle to creativity and a blockage for the world to move forward because that keeps you stuck in a certain bracket throughout your lifetime if you’re not aware of it.

Derek Sivers

Yeah, I agree. Correct.

Raj

I’ve read on your website that you love to work. You do 12 plus hours of work every day, day in, day out. Most people don’t want that. But you love your work. And what people mean by that time is most people just want to run out of that, and they don’t find enjoyment in playing with your work. I want to hear your ethics on that.

Derek Sivers

I use the word work to really mean “me time”. I don’t know how a better translation for “me time”, but me time just means doing whatever I want to do the most. And so I call it work so that people leave me alone. You know, I need to work. But really, what I mean is it’s me time. And for me, I just enjoy writing and programming more than I enjoy playing video games or whatever the hell people, do watching screens. I just enjoy this more. So this is what I love to do most, writing this book, for example “Useful Not True”. I’ve been working on this for two years, I’m almost done. And I have learned so much from doing this. A lot of it I’ve learned from reading other people’s books around the subject, reading other philosophers and reading a lot about religion and other things like that, and understanding why people believe what they believe. But then a lot of it was just sitting for hours at the computer like offline, just a text file, just asking myself questions like, “What’s the real point of that and why? Why would that be? Or what’s another way to think of this? Or how can I explain this better? What’s a good metaphor for that?” And through the process of just sitting with this for so many hours and working on it. I feel like I’ve gotten so much wiser from doing it. And that to me, is a deeper joy than playing a video game or watching TV.

Raj

But what happens to most people is that they get frustrated. Like you said, that you you found joy in just sitting down, just playing with your mind, just being patient enough. And you get a really high level of discomfort when you just sit with yourself. You might not experience this, but that’s why I want to know this from you. Do you get discomfort when you sit for long hours and how do you deal with it?

Derek Sivers

I do, it’s hard. I do things I’m not fully proud of. I drink a lot of caffeine. I take naps. I go on walks, I call friends, I do things like that. So when I say that I work for 12 hours, yeah, usually an average day I wake up at 5:30. It’s a typical time I wake up. I don’t set any alarm. That’s just when my body wakes up and within five minutes I’m at the keyboard writing, and then I do that for a couple of hours. Then I stop to eat breakfast, and I’m happy when a friend calls to interrupt me. Or if they don’t call, then I stop to call them. I drink many, many, many cups of tea. When I’m really frustrated, I will drink a Diet Coke. When I get exhausted, I’ll just go lay down and I actually have the eye mask, and I’ll just lay down on the couch or a bed and put the eye mask on, since it’s the middle of the day, and maybe I’ll fall asleep for 20 minutes or 2 hours and get up and do it again. I’ll go on a long walk. I kick and I scream and I make sounds, but then I just keep doing it because I really, really, really want to make a great book. So it’s the same process, has been for decades. If I was working on even like recording my album when I was a musician in my 20s, I was sitting alone in a recording studio with the same process, and then years later, I was running my business and I was sitting alone at a programming terminal, trying to figure out why the database wasn’t connecting the orders with the shipments or whatever, or trying to get a Linux server up and running and hit the same frustration. I just pushed through it because I really want the end result.

Raj

I guess the better question there is how do you stay intrinsically motivated?

Derek Sivers

Because I just really want that end result. I have this idea for how good this thing could be. And I really want to see that happen. I want that so badly that I push through the discomfort.

Raj

Is being an entrepreneur everybody’s piece of cake or what did how did your life change when you become an entrepreneur? I know that you’ve never done a so-called job.

Derek Sivers

I mean, I did have a couple jobs, but i was always in the mindset. I think it’s a mindset shift. Like I said, I was already in this mindset that says that everything’s up to me. I will never have a paycheck. I will never have a pension or insurance or stability. Nothing will come to me automatically without me making it happen, if it’s going to be, it’s up to me. So that’s the core mindset.

Raj

What made you come to that sort of a mindset?

Derek Sivers

Wanting to be a musician. Deciding at the age of 14, which is a very formative age, saying I want to be a successful musician and therefore, yeah, there won’t be a paycheck, there won’t be a salary, it’s all up to me. So that’s first.

Raj

That creator mindset.

Derek Sivers

Yeah, yeah. You can’t expect stability. Everything’s up to you. And for some people, if you say everything’s up to me. For some people, that thought is deflating. It’s depressing. It’s disempowering. You think, “Oh God, that sounds awful.” For some people, that thought is empowering and that fills you full of energy to go, “Yeah, everything’s up to me. This is great because now I’m not at the mercy of someone else.” Right? Like, you said in one of your earlier podcasts, I listen, you say like, “Please subscribe to please the algorithm.” So even that I have a real problem with trying to please platforms. That’s why I’m not on any social media, because I still have this, like fuck you Amazon. Fuck you, Google. Like, I’m not going to do what you want. You’re not my boss. So I’m not going to please your stupid algorithm. I’m going to set up my life in such a way where I don’t need you at all. So I don’t even put my books on Amazon until a year later, when everybody’s bought it through me directly. And then as, like a little afterthought, I very quietly put it on to Amazon with no announcement because fuck Amazon and I don’t do any SEO.

Derek Sivers

And I just I realized that I could be more successful if I did. But I don’t want to, I don’t. That would feel like selling my soul in a way where, you know, the cliché of selling your soul to the devil, right? Like it might get you more external reward, but it would make you feel terrible about yourself inside. That’s how I would feel if I was trying to please the algorithm. So that’s me. But the point is, maybe that’s not how you feel. Maybe I mean, some of my best friends really like the stability of a paycheck. They don’t want life to be up to them every day. They want to just find a job and then like, cruise, so they can just know that that’s taken care of and they can relax and they can focus on their family and dinner and the garden because they know they have a steady paycheck. And for some people, that’s what they want. And that’s there’s nothing wrong with that. You just have to be self-aware enough to know your own motivations.

Raj

I think I remember reading a quote was like, “Become so free that your whole life becomes an act of rebellion.”

Derek Sivers

Yes. Albert Camus, I think that’s his name. Yeah. I like that one. Although rebellion is a funny, it’s a funny subject because I’m not fully proud of it because it’s still reacting against someone, right. Like, ideally, you would be so independent that you don’t even react. So rebellion is a reaction against somebody, I think. And let’s maybe, hold on. Yeah. Isn’t it rebel? Isn’t that like the word repel? Rebel? Whereas to be fully independent means you’re not even rebelling. You’re just disregarding.

Raj

I guess a better answer would be to use your brains to pick what’s right and what’s wrong. To see what’s wrong, to say that’s wrong, and then figure your way out from there. So like Amazon might be right or Facebook might be right if I feel it’s right. Remember this--- have you read this philosophy of Nietzsche called Zarathustra? I love it so much. I love it so much to the core.

Derek Sivers

What do you love about it? I’m curious.

Raj

Because it makes you become the independent thinker that you are. So what I love about this is it doesn’t reject any dogmas or beliefs, right. So what it does is it asks you to find out. So I’ll tell you the story. I really love this. So there’s this guy called Zarathustra. He was a wise sage, right. And people used to go to get ideas from him, to learn from him, because he’s really wise, right. And the only thing that he said is like, “Don’t follow me.” People were like, “What? You are really wise, man. Why should we not follow you?” So his whole idea was that if you follow me, you will not grow bigger than me. You will be stuck in my thought bracket or where my mind has reached, right. So what I want you to do is learn from me and see using your brain, see if what I’m saying is true. If it’s true, join with me. Let’s grow together. If it’s false, then completely reject it and find your truths. So I find that liberating because you’re not completely rejecting any idea if it’s true, that’s fine. We can be friends. You’re not under anybody. You’re not over anybody. You are becoming friends with somebody, and then you’re finding out more of the world. Right? So a lot of our belief systems doesn’t support this kind of idea. It portrays a sort of authoritative nature.

Raj

And you’re below it. But this idea I found liberating because if your idea is good, you become friends with it and you grow together and you look for the next thing, so you’re not stuck there. We are all growing together, right. And if it’s not true, use your consensus. You have your brains, you know, to deduce what is right and what is wrong. And if you believe that, if you see that’s wrong, tell it to my face. That way we are correcting ourselves and we are growing together as a community, as a world. So I found that liberating.

Derek Sivers

Right.

Derek Sivers

It would be interesting to try replacing every instance you just said of the word true to replace it with useful and instead of wrong, replace it with not useful. Because again, when you think of something as true, that’s a heavy word. Like I said earlier, like that, that means like that’s it, it’s just a fact. I am never questioning this again. It’s just true. You know, squares have four sides. That’s just true. The Earth revolves around the sun. That’s just true. But if somebody says like,”Yyou must honor your parents, that’s just true.” It’s like, is it? I mean, maybe that’s useful for you now, but will not be useful for you in ten years or was not useful ten years ago. But maybe it’s useful for this person, but not for that person. So I think true means like absolutely true for everyone in the universe, like non-human entities, ants and aliens and worms. If it’s true, that means it’s absolutely true for everything in all situations, past and future. Therefore, I think it’s best to think of as little as possible as being true, but instead just ask for useful because it’s also then honoring the changes of time that a belief might be useful for you now and no longer be useful for you tomorrow. But if you called it true, you might feel some kind of loyalty to your past decision that that was true. But a day or a year or a decade later, that belief might be working against you. But because you’ve declared it as true, you might feel loyal to it, like you’ve already decided. I’ve decided that that’s true. But if that belief is working against you, you’ll have a hard time letting go of it. Whereas if instead you had from the start declare that belief to be useful. It it indicates that this is for you and for now.

Raj

That is a more refined perspective. But the caveat there might be useful for me is not useful for another person.

Derek Sivers

Right, exactly. That’s what it’s all about. Never mind other people. Focus on what’s useful for you. That if you just pick any belief. I’m great at what I do. You believing that people out there want to hear this podcast that might be really useful for you to believe right now, to give you the motivation to email me and super impressive people like Robin Hanson and invite him to get on an interview with you. And like the confidence that it took to contact him and the research it took to do that interview with him. You have to believe that the world wants this and that was a useful belief for you. It doesn’t matter whether it’s true or not. It was necessary for you to believe that, to take the actions you needed to take to make it happen, that might or might not.

Raj

That’s Harry Potter’s mirror.

Derek Sivers

Yeah, exactly. So calling something true would be like Harry Potter and Ron arguing about what’s in the mirror. You know, “Harry, it shows me as the president of the Quidditch team.” “No, it doesn’t. It’s showing me my parents.” “Well, yeah. You’re wrong.” No, they don’t fight about that because they know that they’re just seeing what they need to see. I don’t think we should fight about what’s true or not.

Derek Sivers

And we shouldn’t think in those terms. We just think even for the things that feel really true to you, that the beliefs that we think of as religious beliefs, whether it’s actually like a religion or just something about, you know, this is the way that that chicken should be cooked. You know, whether we should be eating chicken at all. You might have something close to a religious belief about that, and it might feel like, absolutely true, like everyone on Earth needs to believe what I believe about chicken. But you need to realize that that belief is just, it works for you. You don’t need to go apply that to everybody else. Somebody else on the other side of the world has another belief that’s opposite of yours and works for them. What you were saying about entrepreneurship. Sorry. I think that’s where I was trying to get at, is the whole mindset of it’s all up to me really worked for me, but for somebody else, that might be depressing and awful and that’s not what they want. So you shouldn’t say that this is for everyone, of course. And therefore, like having a job is not for everyone. Having security is not for everyone. Doing one thing for ten years is not for everyone.

Raj

I was talking with Robin Hanson along the same terms. The elephant in our brains something like this. We are socially cooperative creatures, and sometimes having this sort of a mindset right will pick you off from the herd. Did you have that sort of battles?

Derek Sivers

Oh, well, I’m happy to leave the herd. You know, like I said at the beginning about being a musician, I don’t want to be in the herd. I think if I was in the herd, I would feel that something was wrong. That maybe, if I think the same as everybody else maybe I’m not thinking.

Raj

Yeah, because that I believe, is the core idea of being human, because you’re conscious and you can make conscious decisions. And when the world kind of flows in certain ideologies, right. Like the intuitions we talked about the first intuitive thought that comes and that you never question. You are losing the core idea of being human.

Derek Sivers

See even you saying that you’re losing the core idea of you being human, I think well, that’s one way to look at it. It’s not necessarily true.

Raj

We’re just two dudes talking.

Derek Sivers

Yeah. But, you know, if that works for you. Skepticism. I want to learn more about skepticism. This book would take forever for me to write if I kept learning more about everything related to it. So I think I’ve already drawn the line like I’m just going to finish the book first and keep learning more right after. But there’s a branch of skepticism I don’t even know how to pronounce, because I’ve never heard anybody say it. But phyrronian, I think it’s like p-h-y-r-r-o was the name of the Greek man that was like alongside skepticism and stoicism and Epicureanism that Pyrrho, however you say his name, advocated a kind of radical skepticism. That says, “All I know is I know nothing and I’m not even sure of that.” Like, that might not even be true. That I know nothing. And when I heard this, I went, “Ah, there, this is this works for me.” Like, this is how I’ve already been thinking. I didn’t know it had a name. I didn’t know there was a school of thought around it, but I love the feeling of doubting everything so that anytime somebody says this means that I think, “Well, maybe, what else could it be?” Because it’s just so creative.

Derek Sivers

It just opens you up to make your own meaning and ask yourself, what else could it mean and then what’s the point of it meaning something else. For me, I think the only point is if it changes your actions or brings that tranquility, I was describing earlier about like feeling at peace with the past. If it’s something that’s truly out of your control, maybe you just need to feel at peace with it, but other times maybe feeling a lack of peace is what you want. Say if you need to improve your health, if you’ve been too sedentary, eating too much fatty crap and you do need to improve your health and you don’t want tranquillity to be okay with it, what you really want is dissatisfaction. It will make you jump into action. And the appropriate or the most useful belief is the one that makes you jump into action. So anyway, I really like doubting everything.

Raj

Yeah, but my thinking is that you’re still looking for peace there, right? Because you can’t sit calmly or rooted without doing the thing. It’s driving you. And just like writing your book.

Derek Sivers

Okay. Nice angle, I like that.

Raj

Have you heard the story of--

Derek Sivers

By peace, you want to solve your dissatisfaction? Is that what you mean? Yeah,

Raj

Right.

Derek Sivers

You want to feel at peace with your fitness? Well, that’s a good one, I like that.

Raj

Have you heard the story of Sisyphus?

Derek Sivers

Of course. Yes.

Raj

So maybe it’s like that. You must imagine. So for all those listening, the story of Sisyphus is I think it was a Greek god. And Sisyphus cheated death 3 or 4 times. And the gods gave him a punishment to roll a rock up a hill. And the caveat being, every time he rolled the rock up to the top of the hill, it will bounce back to the bottom, and he can only escape or do other things once the task is done, which goes about to infinity. And I think it is Albert Camus itself. I don’t know, I don’t remember exactly, but human life is compared to that hedonic treadmill of the never ending desire. And you find happiness in that, or your peace or solace in that.

Derek Sivers

Right. And I think maybe Nietzsche with his, amor fati, said, like, “Imagine Sisyphus smiling and loving this curse.”

Raj

Yes. Right. We’re still looking for that solace somewhere, right. Was looking through your website and I found this word, xenophile. What are the perks of being a xenophile? What is a xenophile? And what are the perks of being a xenophile?

Derek Sivers

I only learned this word recently. So it’s spelled x-e-n-o-p-h-i-l-e. I had heard xenophobe, which are people that are scared of foreigners, so I believe the word root xeno means foreign. And so xenophobe like a phobia. Somebody who’s scared of foreigners. There’s a whole series of cute books on foreign cultures called the Xenophobe’s Guide to Belgium, the Xenophobe’s Guide to Russia. And they’re wonderful little culture books. Actually, they’re funny but true. You know, like a comedian. The best jokes are the ones where they have actually an astute observation about the way people act or the way things are. And that’s what’s funny about it. So the Xenophobe’s guides are a great series of books, and I’d never considered the opposite. And then one day I just kind of out of the blue, I went, “Wait, is that a real word? Xenophile?” And I looked it up in the dictionary and it is. So it means somebody who loves foreigners. And I just thought, “Yeah, I am.” I almost irrationally prejudiced in favor of anything foreign because it’s the surprise. It’s the mind expanding. It’s the learning a different worldview. I spent time this past year in the Middle East and learned a lot about Arab culture, something that was completely off my radar. Not even one year ago today.

Derek Sivers

Yeah, even a year ago today, I had never been to the Middle East. I had no interest in going. In fact, I would have put it in my top ten list of places I don’t want to go. And then about 11 months ago, something just came up, I think I had booked a flight that was going to have a layover in Dubai. And I went, “You know, I should get out of the airport, just go see.” And so I turned it into a three day layover. And then because I had this three day layover, I went and read a few books about United Arab Emirates and Dubai. And suddenly I was fascinated. And then I contacted some people I know that live there. And I asked them and they got me more interested in it. And then they introduced me to people that I had to meet and told me that the cultural museum I need to go to and who I should talk to there. And suddenly I was in with friends, Emirati friends in Dubai and Abu Dhabi and wow, I love it. And so I feel that every time I turn towards the xeno, towards the things that feel foreign to me, it’s expanding my horizons, which then kind of expand my self-identity to what I feel connected to.

Raj

That is a liberating worldview, right. Because our brain is naturally accustomed. It’s one of those intuitions to, even in interview processes, in psychology, there is this term called, silent racism, right. So you you might not be explicitly showing racism, but our brains are biased to like the things which look like us, talk like us, and we have a comfort, it’s it’s not your conscious mind. This is an unconscious thing that happens in your brain, right. And the xenophile is such a liberating idea to that. It’s going in against your own psychological, unconscious psychological biases.

Derek Sivers

We’re not all alike. And so, sorry anybody watching the video you might have seen me suddenly smile when Raj said this bias. Because I think I’m the opposite. I think I’m actually biased towards, even just subconsciously, even just like in my little minute reactions, I think I’m actually biased towards people that are not like me. And that’s where I first noticed this. I noticed that I was actually being prejudiced against anybody that was similar to me and prejudiced towards anybody that was dissimilar from me. I was like, “Ooh, tell me about that.” I wanted to know more or something was more interested in somebody the less they’re like me, the more interested I am. In fact, I got the first hint of this in 2008 when I tried moving to San Francisco. I just thought because of who I am and tech circles. And I was even born in San Francisco but we left when I was one year or two years old. And I thought going to San Francisco felt almost like destiny. It felt like this is my place. I was born here. My kind of people, techies, smart, thoughtful people. I’m going to San Francisco. And I went and I hated it because everybody was like me and suddenly I was like, rebelling against all of my surroundings, and I had to leave after six months. I was just like, “Ah, I hate this. Everybody’s like me.” But then you put me in a place like Dubai where very few people are like me, and I go, “Ah, there, this feels better.” I just like it better. You know, I loved living in Singapore. New Zealand I have a strange-- I feel very connected to the land of New Zealand, but not the people as much. So I’m not sure what to think about New Zealand through that lens. Yeah. Anyway xenophile. Thanks for asking about that. I hadn’t thought about that in a while.

Raj

Even when I talk to you right now, I can see how you think slowly. And. You. You’ve mentioned it in a couple of places to the art and the benefits of thinking slowly. How does that help? Or how has that shaped your life?

Derek Sivers

Well, first I should say that it’s not intentional. It’s not like I decided that I should think slowly and therefore I do. It’s more like, I noticed that when I was, say in a debate on something, or even just in a good conversation, that I’d have many more thoughts a day or two later about what I was talking about earlier.

Raj

You’re so right. Because I do these interviews. I do my podcasts, right? I do this thing right, and I talk to people, and two days later you think, “Oh my God, that’s a really good response. I could have talked about that.” One thing comes, another thing comes. Yeah.

Derek Sivers

What if it became normal that all podcasts were assumed to have part one and part two? Like, let’s just admit that a lot of us are slow thinkers, let me book you for 45 minutes this day, and let’s do another 45 minutes, you know, three days later. So I noticed this about myself. And at first I thought, “This is something wrong with me. I need to work on this. I need to get lightning fast. So as soon as somebody says something, I’ll have a quick reply.” But then the more I thought about it, I thought, “I don’t know, quick replies are initial reactions.” And, you know, we already said what I think about initial reactions. I think your first thought is an obstacle that you need to get past. And so I don’t honor the first thought. And so I don’t honor the quick thought. I like the thoughts that come later. I like them better. Years ago, Tim Ferriss and I did a podcast where he said, “When I say successful, who’s the first person that comes to mind?” I thought, well, I don’t care about the first person that comes to mind.

Derek Sivers

Let’s who’s the third person that comes? Let’s push past the first one, okay. First person comes. I don’t know Richard Branson. Who cares? Now let’s go a little further. Why? What is success? What do we mean success? Like successful according to who? According to me? So are you asking my definition of success? Is that the real question? What are we really talking about here? Like that’s a more interesting line of thinking. Instead of just giving, you know, the first thing that comes to mind. So eventually I posted an article on my site saying I’m a slow thinker. And it felt like a confession, like somebody saying, “I’m just bad at email or I’m addicted to coffee in the morning.” You know, whatever. Yeah. Just decided to admit my foible. And it’s been sweet that a lot of other people came out of the woodwork to say, “Oh my God, me too. Thanks for admitting this.” And then deciding instead to just roll with that nature, to use that nature of mine, instead of trying to deny it or work against it.

Raj

So let’s go to your book, “Hell Yeah or No”. So it’s not yes or no? It’s hell yeah. If you don’t feel that hell yeah. It’s no right. Let’s let’s go there. Let’s talk to the idea behind that.

Derek Sivers

Sure. The big idea is that you will have more impact on the world. You’ll be more rewarded, more well known for doing one great thing than you will a million little things. Nobody cares what you’re bad at, so you don’t even need to do those little things. It’s better to say no to them, because to do one big thing takes a lot of time and energy. But if you’re spreading yourself too widely, saying yes to too many things, then you won’t have the time and energy to throw yourself into the one big thing that really matters. So the big idea is to say no to almost everything, unless it’s a big giant hell yeah. Oh my God, that would be amazing. Absolutely, yes. And because you’ve said no to so many things, you actually have the time and energy to throw yourself into the big yes that comes along. Even if you don’t have a big thing yet, it can be useful to leave the space for it to arrive. Like by saying no to more things. Leaving that emptiness. Don’t fill every hour. Don’t even fill every day. Leave the emptiness in your life so that when a big thing comes along, you have the time and energy to throw yourself into it right away.

Raj

I think it’s even more applicable now because we are living in an age of distractions, right. Every day our phones are sucking our energy. We are not bored even for one second of our day. So your mind wandering is not happening and maybe you’ll be able to say that that all that creativity or your energy or whatever, when you are not distracted, you’re allowing more things to come in. Do you meditate?

Derek Sivers

No, no.

Raj

That’s another perspective that, I think you’re already meditating because you’re so focused. I read somewhere this about meditation, it’s not just sitting looking at your breath. So it’s having that one thing, so everything in your body, every cell in your body gets aligned to that one idea. Same as it might be your hell yes idea. And when you offer your life to that hell yes idea, you become the master at it.

Derek Sivers

Right.

Raj

And, you talk about mastery too.

Derek Sivers

I should give the caveat that “Hell Yeah or No” is just one tool in the toolbox. It should not be used for everything. So, for example, if you were just out of college and you’re looking to do something and you don’t know what it is, it can be a great strategy to go say yes to everything and go be everywhere at once, so that when the lightning of luck can strike you if you’re everywhere. You never know when luck is going to strike. So it can be a great strategy to say yes to everything up front. But then, once the world has started telling you what it wants from you once luck has struck you and now you’re overwhelmed with opportunities, that’s when you might need to go back into the toolbox and pull out the hell yeah or no tool and use that instead.

Raj

I remember reading a book I don’t explicitly remember, but it was saying, like, to find your thing, go to 20 things first, and when you do 20 things and if you still haven’t got, then maybe look for advice. Otherwise, how would you find what your thing is, right?

Derek Sivers

I like that.

Raj

I remember I read this quote from your website, M”astery is the best goal because the rich can’t buy it, the impatient can’t rush it, the privileged can’t inherit it, and nobody can’t can steal it.” Loved it.

Derek Sivers

Me too. I love that quote. It’s funny that I’ve asked my musician friends if when they write a song do they feel it’s like the best song ever written and all of my musician’s friends say yes. But so far, every author I’ve talked with when I say, “When you write a book, do you feel it’s like the best book ever written?” Every one of them has said no. But when I wrote “How to Live”. It really felt like this is the best book ever written. This is really the greatest achievement of humanities. This book right now. Okay. Wait, that’s an exaggeration. I really did feel it’s the best book ever written. Like, if I had not written it and I had found that book, that would just be like far and ahead ten times more than any other book that would be my favorite book of all. I wrote my favorite book, and that’s a wonderful feeling. So even now hearing you quote that at me, I’m like, “God, I love that quote.” It’s a weird thing to admit. I feel like it’s like we’re not supposed to say that but it’s honest.

Raj

That journey towards mastery is what I was asking, right? The ups, the downs.

Derek Sivers

You’re like, “Yeah, yeah, enough self-praise. Can we get back to mastery?”

Raj

No, no, I sincerely loved it, man. Like, that’s why I took it out. I loved that, I wanted to explore more on that.

Derek Sivers

Mastery is, I think of it as more fun than fun.

Raj

Okay.

Derek Sivers

That there’s shallow fun and then there’s deep fun. So shallow fun might be to just screw off and go hang out with friends or play a video game or do something stupid. Deep fun can be like diving deeper and deeper into one thing. And of course, it’s challenging and has its frustrating moments, but the deeper joy you get out of expertise. I think it’s way more fun than shallow fun.

Raj

Because I remember this story you telling. I saw a parts of the Tim Ferriss show that you had the talk with Tim Ferriss, and I remember you telling him the work you do to put a computer. You sit all night long assembling your computer, and in the morning it works, right? And that deep fun. That’s only yours. Nobody can take it from you.

Derek Sivers

Yeah, which might have some other emotions with it. Like that nice feeling of self-reliance. Like I built that. That’s a great feeling that you can’t buy that joy, right? Same as I said earlier about, like, not wanting to please the algorithms. That it’s much harder to build my own bookstore. It’d be easier to just go, oh well, and just put it on Amazon. But instead I built sivers.com, my own personal bookstore where I get to price things the way I want and I get to do things that Amazon can’t do. Like say, if you buy the paper book, you get all the digital formats included for free. You get the e-book, the audiobook one of my books even has a video book. The entire book was turned into an animated video. You get all of that included for free if you buy the paper book. Amazon never does that. They can’t do that. Their system won’t allow that. They can’t do that just for me. They can’t do it just for you. But I was like, “This is what I want. So I’m going to build my own store.” And it’s a deeper joy. We all get the joy from different things. Some people get the joy of just delegating work to somebody else and just having it done. Whereas some people get the joy out of doing it themselves. Some people get the joy of turning up first in a search result in Google, and some people get the joy of ignoring Google.

Raj

I read this book from Angela Duckworth. It’s called “Grit”. And that is a big motivator, I guess. Right. How do you mind that grit?

Derek Sivers

I haven’t thought about it in a while. I also read that book, but it was a few years ago. Her thing was about the sticking with something, I think if you learn music, you can learn anything. Meaning like if you learn to play an instrument well. Those skills are applicable to learning anything. Including say, if you’ve got a big piece that’s complicated to play on your instrument, and you can play 80% of it well, but 20% is really hard. Or maybe let’s just say 1% of it is really hard. You learn that you just practice that 1% over and over again, slowly, then faster, then faster until your muscle memory gets it. And now you can do the thing that you couldn’t do earlier today. And then you zoom out and you put it in the context of the bigger piece. That’s how musicians practice. And I think it can be the same for other skills, like even entrepreneurship. There should be a way to practice entrepreneurship, practice communication. Practice making friends. If you have a hard time making friends and you want to make more friends, you should be able to practice the aspect of making friends that you find particularly hard. It’s taking that practice approach to anything.

Raj

In your book, How to Live. Use one chapter, as you say, to pursue pain. That’s so counterintuitive. Why is that?

Derek Sivers

Well, first, I think it’s the job of a writer, maybe even a speaker, maybe even anything you put out in the public to be surprising. Because if it’s not surprising and then you’re just telling people what they already know, you know, be good, work hard. So pursue the pain. I found was a common theme behind most rewarding things in life come from doing what’s not easy. Most people float downstream like a leaf on a creek, just doing whatever comes easy. Just go with the flow. I like the saying, “Only dead fish go with the flow.” That all the other fish swim against the current, that’s part of being alive is to swim upstream as well, and not only downstream, and to do what’s difficult because that’s more rewarding. That’s where you will grow and improve. There’s the obvious comparison of fitness and strength. You get stronger and fitter by lifting heavy things and doing what hurts. Relationships often what destroys or harms a relationship is when two people are not saying the thing that they need to say because it’s uncomfortable. Whereas so many things in relationships can be improved just by having that difficult conversation instead of avoiding it. So again, that’s another example of steering into the pain.

Raj

What I love about that is the dichotomy of life. Again, by the two examples you said if you go to the gym and it it requires hard work just to keep your body fit, but that’s rewarding. But if you don’t go to the gym, you’ll become unhealthy. And that’ll also give you a hard time. And in your relationship, if you’re communicating, it’s hard work. You have to learn how to communicate. You have to learn to tie down your instincts and your reactions. You have to learn it’s hard, but if you’re not communicating, you’ll have issues. It’s hard either way. But once more rewarding and once more fulfilling.

Derek Sivers

I like that, Raj. You’ve done that twice in this conversation where you pointed out the long term effects. I think when I said, oh, feeling at peace. You know, doing what you need to do or feeling at peace. And you said, actually, you know, doing what you need to do will help you feel at peace. That was a really good insight. And this one too.

Raj

Yeah. That’s something I noticed about life. Okay. Then let’s end it with the big question. What’s the meaning of it all? What’s the meaning of life?

Derek Sivers

I will tell you a fun little story that is a chapter in my next book called “Useful Not True” that I went to a workshop once where the presenter or the workshop leader. Whoops. Sorry. It’s my note that I need to go. The workshop leader wrote on the board. He wrote, “Life is” underscore blank line. And he said, “What word goes in that blank?” And he said, “It’s actually time to break for dinner right now. So everybody over dinner discuss what word goes in that blank. And when you come back from dinner, I will tell you the meaning of life.” And so over dinner, I was at a dinner with seven people and one of them said, “Life is learning.’ And somebody said, “No, no, no, life is love. Love is the ultimate emotion.” Somebody said, “No, life is time. Life is how we measure the time between when we’re born and when we die. Therefore, life is time.” And some nouveau Buddhist said, “No man, life is suffering.” Kind of repeating his recent lessons. Somebody said, “Life is teaching.” And I’m usually talk talkative, but I just sat there listening to everybody thinking, no one of these things can be the answer. Because everybody’s disagreeing. Therefore no one of them is necessarily true. And I thought, wait, if none of them is the answer, maybe that’s the answer. Maybe life is, you know, underscore.

Derek Sivers

Maybe that’s not a question. Maybe that is the answer. That life is a blank meaning. And I went, “Oh, I like that.” And yeah, sure enough, after dinner came back and found that that’s what the presenter had intended. That nothing has inherent meaning. It’s all just what you put into it. So he even asked the audience at one point he said, “What does it mean that you’re here at this event?” And somebody said, “It means that I’m trying to improve myself.” And somebody said, “It means that I’m holding to my commitment.” And somebody said, “It means that I’m open to learning.” And he said, “Nope. It doesn’t mean that.” He said, “You might be putting that meaning into it, but that came from you. That’s internal, not external.” So I really like that a lot. I love the idea that nothing has inherent meaning. Life itself has no inherent meaning. It is a blank slate that you can project whatever meaning you want onto it. And I think the best measure of that is whatever you find to be useful, that if you find it useful to think that life is giving and that’s the meaning of life. Then if that changes your actions for the better, then that’s a useful belief for you. But you shouldn’t think that any of these is necessarily true. It’s not external, like, you know, water is two hydrogen and one oxygen atoms.

Raj

That’s the objective definition.

Derek Sivers

Right. It’s you. It’s your whatever works for you.

Raj

Love it, love it, man. Like life is your blank canvas. And paint it whatever you like. It’s going to be hard if you paint it or just sit and see what painting comes out. And maybe it’s more rewarding if you decide to paint it.

Derek Sivers

Yeah. You just have to stay attuned to what works for you, your own necessity, your own needs, motivation is delicate. You got to really be careful and notice what’s working for you and what’s not. And on that note, hey, you know, everybody listening to this. I really like hearing from strangers around the world. As you can tell. So, I mean, that’s how Raj and I met is he just emailed me out of the blue a couple months ago with some really interesting questions. And that’s why I’m here. So, anybody please go to my website, go to sive.rs And send me an email and say hello.

Raj

Get more of Derek and his books and his ideas.