February 10, 2020

Derek Sivers | Introversion, World Travel, Writing, Learning, and Retirement

Derek Sivers (@sivers) is a writer, musician, programmer and entrepreneur best known for being the founder of CD Baby, an online CD store for independent musicians. A professional musician (and circus clown) since 1987, Sivers started CD Baby by accident in 1997 when he was selling his own CD on his website, and friends asked if he could sell theirs, too. CD Baby went on to become the largest seller of independent music on the web, with over $100M in sales for over 150,000 musician clients.

In 2008, Sivers sold CD Baby. His current projects and writings are all at sivers.org.

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My guest today is Derek Sivers. Derek is a writer, musician, programmer and entrepreneur, best known for being the founder of CD Baby, an online CD store for independent musicians. A professional musician and circus clown since 1987, Sivers started CD Baby by accident in 1997 when he was selling his own CD on his website, and friends asked if he could sell theirs too.

CD Baby went on to become the largest seller of independent music on the web with over $100 million in sales for over 150,000 musician clients. In 2008, he sold CD Baby to focus on his new ventures to benefit musicians.

His current projects and writings are all at sivers.org, and I know he’s going to hate this right now because he’s not about that self-promotion stuff, but I’ve just got to plug it right now.

If you go to sivers.org/about, his ‘About’ page of just plain text – that’s all it is, no gimmicks, no fancy stuff there – his self-written ‘About’ page is really fascinating. I guarantee you that if you read through sivers.org/about, you’re going to start to think about things differently.

His perspectives of the world and life are hard to explain, but you’ll see when you go to sivers.org/about.

And we’re not going to talk about anything business today, so if you want to learn all about Derek Sivers and business and his business philosophies, I highly recommend his book, “Anything You Want”. I listened to it on Audible. It was an hour and a half I think, and really enjoyed it

So, if you want to learn about that stuff, which I highly recommend you do, read “Anything You Want”. And he’s also got some new stuff coming in too, I’m not going to say anything about that either. So, good person to follow right now. Sorry I had to plug you, Derek, [laughter] but welcome.


I’ll manage [laughter]. Thank you.


And also, it’s worth mentioning, I’ve long thought you’d be one of the world’s greatest thinkers. I’ve listened to your appearance on the Tim Ferriss Show. I listen to it every year on a long car ride. I can remember these specific car rides too, but I’ve listened to it every year for the past however many years since it came out.

And one of my favorite quotes of yours is, “If more information was the answer, then we’d all be billionaires with perfect abs.”

So I’ve got to ask you the question, as someone who says no to a lot of things and is really good at saying no, why are you here?


Oh, I liked your questions.

I don’t have anything to promote. Usually people go do podcasts when they want you to buy their book or sign up for their company. I have nothing to promote, and even if I did, I just don’t like that kind of relationship where you can just tell that the person is here to pitch some agenda.

So, instead, I only decide to do interviews if I think that the interviewer has some really interesting questions, and you sent me some really interesting questions. And I’ve listened to some of your past podcasts and I said, okay.


Oh gosh, Derek, I really hope they’re not old, old ones.


Mark Manson’s a friend of mine, so I had to listen to that one.


Great. I’m glad you heard that.


I like your style, I like your questions, and here we go.


Ditto, here we go.

If I were to ask you, who is Derek Sivers, what would you say?


Have you noticed by the way that if you use somebody’s full name, you’re referring to their public persona? [Laughter]

We just mentioned Mark Manson, and he’s famous. So, if you’re hanging out with Mark, then you say something about Mark, but if you say, I’m here with Mark Manson, then you’re referring to the public persona.


Let me rephrase the question. [Laughter] Who is Derek?


I’ve learned to distinguish between the past, present and future tense of identity.

Past tense, I was that stuff you said in the intro - professional musician, ringleader of a circus music producer, entrepreneur, public speaker, even nomad. I had to realize recently that that doesn’t apply anymore.

So, present tense, I’m just an author. That’s really all I’m doing. All those other titles don’t apply to my present self. Future tense, who knows? But I’m really careful now which tense to use because I realized recently that we can’t keep stating our past achievements as if they’re still who we are.

Someone who played football in high school can’t just keep calling himself an athlete forever. At some point, that status expires. So, I think it’s healthy to expire it as soon as possible. Define yourself only by what you’re doing now, not by what you did even last year or what you plan to do.


I’ve always gotten a feeling of humility from you, and perhaps that comes from this philosophy. You don’t wear your achievements on your sleeve all day, every day.

Perhaps you wake up every day as if you’ve accomplished nothing and you have the beginner’s mind. Would I be correct in assuming that?


I’m usually lost in whatever I’m doing at the moment. I learned a word three days ago, “monomaniacal”, and I read the definitions and I thought, “Oh, that fits me.”

I get really into one thing at a time. And I will wake up at 5:30 in the morning and do that one thing until midnight, stopping for 20 minutes to get something to eat. But I’m that sit down and work for 17 hours kind of guy.

Even when I look back at my 10 years running CD Baby, that was one single thing I did for 10 years, pretty much seven days a week, 12 hours a day for 10 years. I hardly took a break.

You couldn’t get me to hang out. I didn’t watch any TV, I didn’t go to restaurants, I just worked 12 hours a day for 10 years. And so, I’m monomaniacal, I get really into one thing. I don’t know if it’s humility as much as just honesty.


I’m very similar with working on something all day, every day for years on end and not really watching TV, not going out, not hanging out.

I kind of tucked myself away to do this work, but I also get the sense that perhaps the terms ‘work’ and ‘play’ are kind of interchangeable for you.

But does it get to a point where doing that, throwing yourself away, is unhealthy?


No. I think because it’s play.

I call it work because that’s the socially acceptable term that we all understand, but I think the more accurate term would be to call it “me time” – doing whatever the hell I want to do, which might be learning a new programming language, or working on my book, or editing audio files, or answering a few hundred emails if I’m in the mood to do that.

It’s just “me time.” So, who could ever say that too much “me time” or too much doing what you want is a bad thing? So, no, I don’t think it’s a bad thing.


Playing devil’s advocate, I’m very similar. We’re both introverts, but as human beings, we need other people.

In isolation, people don’t do too well. For example, there’s solitary confinement as punishment because that isolation is just so terrible for human beings. We wither.

Do you ever feel lonely?


Well, we’re not mentioning something. . . I have a kid, and so despite everything, the time I spend with him just in our regular weekly routine is about 30 hours a week. It’s just one-on-one, me and him.

I shut off myself and just exist for him for about 30 hours a week. He leads the way; I get lost in his world. I’m with him a lot.

And I do have other friends.


What about 20s and 30s though?


I was much more social then because I think you can mix it with other goals. There was a lot of time in my 20s when I was trying to get famous. I would go to conferences and meet everybody and keep in touch with everybody.

I was much more social in my 20s and even 30s because I was still trying to get famous. Even though it had this ulterior goal of making music or working on CDBaby, it still meant that I was super, super social.

Also, I’ve had phases in my when I’m more interested in the people around me. When I moved to Singapore about 10 years ago, I was fascinated.

I was like, “Oh my gosh, I’m living in Singapore. This is amazing. I’m a permanent resident of Singapore now. I want to get to know my new neighborhood.”

So, I met with everybody. For two and a half years, I said yes to every invitation. I had one-on-one meetups with about two to three people a day, about 15 people a week. I’d go to every event, say yes to every invitation to everything, so I met probably 500, 600 people in that time in Singapore.

Then I moved to New Zealand, and I was completely anti-social. So, I have phases where I’m more social than others.


Because I’m an introvert, I feel people’d out after being around people for these extended periods of times.

Do you ever feel that way?



But I get huge benefits out of going to conferences and parties. A lot of my dear friends now are people that I initially met at a conference.

I think the lesson I’ve learned is you wouldn’t avoid museums just because you don’t want to look at every single painting inside of them.

So don’t avoid conferences or parties because they have 500 people there. You don’t have to talk to 500 people.

In fact, my old art history teacher in college said, when you go to a restaurant, do you order everything on the menu? No, of course not. That’s why when you go to a museum, you pick one painting you want to see, and you just look at that one. If you want to look at another one then you come back on another day. But do not get “indigestion” from trying to overeat at a museum.

We could go two blocks down the road to the Museum of Fine Art and walk in as a class, look at one painting, and that was it. We would sit in front of one painting for an hour. You wouldn’t get “indigestion”.

The same thing applies to crowds. You can attend a conference for two hours and speak with two people. Just because the conference is three days long of 17-hour days, it doesn’t mean you have to attend all of that. Quite a few times, I’ve attended a conference, even the stupid expensive ones, like TED, and not go to the entire thing. I’ll spend $7,000, plus airfare, plus hotels, go all the way across the world, and I’ll just spend a day and a half there.

I got an interesting little tip from Seth Godin. I already knew him, but I saw him at the snack bar at TED and I said, “Oh man, did you just see that talk by Elizabeth Gilbert?”

He said, “No, I don’t go to any of the talks.”

I said, “Wait, what?”

He said, “No, no, no. You’re still an amateur at this. Those of us who have been doing this a while realized that all the benefit comes from hanging out here in the snack bar. Don’t waste your time on the talks. If a talk is good, you’ll hear about it later, and they’ll post the video online for free. Don’t sit in that chair, you’re at TED. Talk to the other people around you.”

It was very interesting. He went all the way to TED and hung out at the snack bar for a couple of days. That’s it. So, you can do events any way you want.


I’m just imagining Derek and Seth at the snack bar having that conversation. It’s a funny little picture in my head. Seth’s a funny guy. I don’t know him personally.


Oh, he’s just like that in person. He’s the same. He’s such a guru, such a sage.


But he would never say that about himself, of course.


No, but he’s changing culture.

I think my other thing about getting ‘people’d out’ is also that you should get used to saying goodbye early.

Very often, I will go to a party and I’ll hang out for an hour. It’ll be 21:00 or 20:00 and I’m said, “I’m going to go.”

People say, “What, you’re leaving?” I’m like, “Yeah.” That was good for me.


I think about that all the time. When I’m there, the thought will creep in my head that this should be the time that I say goodbye.

But for the next 23 minutes, I will be thinking about how to perfectly do it. Oh, is this my moment? My heart starts racing, “Oh, I’m going to say it.”


As if anybody cares.


As if anyone cares, right. I think – don’t flatter yourself here, thinking that I’m so important.

Do you do just do it?


I often don’t even say goodbye. I think “that’s enough,” and I slip out.


We were talking about choosing who you want to interact with. And you said that this can extend to a party, right?




When we were in college, one of my best friends and I would go to the bar or a party. As an introvert, I always wanted to be near him. He’s super social, knows everyone, and it was a good comfort zone for me to be near him.

I really just wanted to interact with him, but he is the polar opposite of me – the epitome of an extrovert. No matter who he goes to a bar or party with, he wants to break off, be on his own, make his rounds and just do his thing by himself.

So, it wouldn’t really work. Some people don’t like that. I find a lot of people my age – I’m 22 – don’t really like that. They call it clingy if you go to a bar or a party and you just hang around them all night.

Do you have an antidote to that?


Yes. I highly recommend if you’ve said yes to some event – big or small – to find one of those books about people skills and read it just a couple of hours before the event because then you can go and specifically try techniques that you’ve learned, just to see what happens.

Then, you’re suddenly more interested in other people if it has a bit of a challenge or if you’re applying something you’ve learned to it.

The very first time I attended TED, I didn’t talk to anybody and nobody talked to me. I was kind of terrified. I was overwhelmed.

There were all these famous rocket scientists around me. I mean, what do you say to a rocket scientist? “You like rockets?”

So, the next time I went, I said, “OK, I’m not going to do that again. It’s too fucking expensive to go all this way and not talk to anybody.”

Because last time I wished somebody would have come up to me and talked to me, I’m going to be the guy that breaks the ice. Everybody wants somebody else to break the ice.

It’s the opening dinner. I walked in and there’s a woman sitting alone at a table looking a little lost, so I’m like, “OK, here we go.” I walked up, and I said, “Hi, where are you from?”

She said, “Oh, I’m Maria, I’m here from Bulgaria.”

I said, “Whoa, Bulgaria, I’ve never met somebody from Bulgaria. Have you ever heard the Bulgarian Women’s Choir? It’s some of my favorite music in the world.”

And she goes, “Oh my gosh, how do you know that?” Then, she told me the story about how she got a scholarship to attend the event, and that’s Maria Popova from Brain Pickings. Do you know that site, Brain Pickings?


I’ve heard of it.


She went on to become quite successful and she’s one of my favorite people that I admire the hell out of. And it’s just because I was the one that walked up and broke the ice and said hello to her.

So, I did that once or twice a day for the next few days. I just found one or two people that looked like they were standing alone and needed somebody else to say hello, and I said, okay. Even though I don’t necessarily feel like it, let’s just see what happens. I’d go up to a stranger and say, “Hi, what do you do?”


That’s funny because of the way you mentioned reading that people skills book before you go to X, Y, Z event.

Some of my favorite things to learn are human behavior, communication, people skills, and the book I would study specifically is – I don’t know if you’ve ever heard of “Vanessa van Edwards?”




No? She wrote this book called, “Captivate the Science of Succeeding with People,” and that is my “bible” of people, the science of people that I always refer to.

I would get psyched up and pull out my notes from that before going out. So, I’m on board with that. Then I’d just focus on one or two things to work on this time, not trying to tackle every little thing in the book,

Then next time, you’ve got those and you’ll add a couple of new things to your references.


It’s all artificial, but I think that real friendship can come after.

The techniques are just there for the first two minutes, and then it’s a regular conversation.

But I’ve got to say, man, the fact that you say yes to an event, but then you go sit next to your friend, I think you should start to be more honest with yourself to start.

Just say, no, I don’t want to go. Its four hours that instead of going out to this event to sit by your friend, you could be doing something you really want to do.


I agree. I can’t remember a bar or party that I’ve gone to for the past two years. It was really the two years prior to that. It just got to the point where it’s was like what would I rather do here? And by going out here, what am I passing up? What’s the opportunity cost?

It’s hard for me as an introvert when I go out to these events. Even though it might not look like that on the surface, my brain below the surface is definitely freaking out.

It would also cost me the time and a quiet night, which I so enjoy.

Speaking of quiet, I know you’re a fan of silence after reading your ‘About page.’ Did you find that the noise levels at some of these events bothers you?


Of course. I have a hard time picking up voices in a crowd, like shouting in a bar thing. I just don’t participate.

If I’m in a noisy bar and somebody’s shouting at me, I lift up my hand, and I walk out the door.


Absolutely. I feel that.

You say you’re a writer, but you’re also podcaster are now too.


Well, in some definition.


In some definition. You started in September, and put one out every single day.


No. I did for a little while, but now it’s every few days.

I’m using the medium of the podcast to just do an audio version of my blog. Each episode is one or two minutes because each one of my blog posts is around 20 sentences.

I think that’s just related to my minimalism. People who visit my house are shocked that it looks so empty. A few people that come over will say, “Do you live here?” “Yep.”

They’re like, “You don’t have any stuff?”

I’ll say, “Nope.” But it’s the same if you look inside my closet, there is my one pair of pants and my three shirts. That’s all I got.


So, with one pair of pants I’ve got to ask the question, do you do laundry every other day? How many times do you wear them? I’m serious.

James Altucher does the same thing too. In fact, he would buy three plain shirts every week instead of doing laundry because it would cost $14. Wear them through the week, and then he’d get the three for the weekend and then throw them out and get new ones.


You know what’s funny? It’s how we have different definitions of words like nomad or minimalist.

My friend, Tynan, came over, and he has a book called “Life Nomadic,” and that’s how I met him. He travels the world constantly. So, his version of nomad is that everything fits into his one tiny little backpack.

He came to visit me in New Zealand, and he comes to my house and he sees my clunky old laptop and he’s like, “What the hell? Why do you have this ancient, old laptop?” Because yeah, it’s 10 years old. It’s giant and clunky and it’s broken a few times and I repaired the parts. I refuse to get a new one because my definition of minimalism is stepping out of the consumer rat race.

I don’t like to buy anything because I hate waste, and whenever you buy something, it creates waste. It’s like the waste of manufacturing, waste of trash. So, I have a big bulky laptop because it still works from 10 years ago.

But anyway, how I wear my pants? Glad you asked. I treat jeans like a jacket. I’ll wear a pair of jeans for a few weeks without washing them, and then after a few weeks if they get muddy or start to smell, then I’ll wash them. And I have a pair of shorts, so I’ll wear my shorts while I’m washing my jeans, then I’ll put the jeans back on.

I have never been asked that before.


[Laughter] Yeah, I’m just curious.

I’ve so often wondered that whenever James talks about it and I really should just be asking James because he’s my friend, but you said it and I was like, alright, now’s my time to ask that question.


That shocks me, about buying and throwing away three shirts so often. That’s the opposite of what I want to in life. That horrifies me, but I just like having the minimum necessary. It’s the common theme.

If you go to my site, sivers.org, it’s the most bare bones I could make it. It’s just the text. There’s no graphics. There’s no sidebar. There’s no navigation. There’s no ads. I don’t even do any tracking. There’s no cookies. There’s no JavaScript. There’s nothing. Here’s the plain text. I edit and I make it myself by hand,

I don’t use WordPress or any site making thing. I wrote every line of that myself, so I don’t write a single line unless it’s necessary.

Same thing with my articles. First I write a long one, saying everything I want to say, then I go through and I chop and I edit my chops and I cut it down until it’s the shortest I can possibly make it – the fewest words, the least code, nothing more. No bloat.

It’s same thing with my book. Nobody likes those books that take 300 pages to say what you could say in three pages. People complain about those, and especially in non-fiction, there are a lot of those. Somebody has one idea and the publisher signs them to a publishing deal and says, “Okay, now turn that one idea into 300 pages”, and you can tell. Nobody likes that.


Would you say then that truth is succinct, and it doesn’t really need to be a 600-page book. That it can be a very bare bones minimalist, plain, short blog post?


Well, truth and stylistic preference are two different things. So, no, I wouldn’t say that truth is succinct because very often, I think people say untrue things because they’re trying to be quippy. They’re trying to fit some wisdom into a sound bite, and so they say something that isn’t actually true.

If you were to try to get to the truth, you’d have to include some nuances like how that applies in some situations, but not others. But now you’re no longer making a nice sound bite or aphorism.

So, very often I think the truth is not succinct.


Now, your stylistic preference is, of course, short minimalist. Your podcasts are very short, which are similar to the blog posts, which are relatively short.

And then in 2010, when you gave those three,TED talks, they were about two, three minutes each?




And then on your ‘About Page’ you say, I want to make lots of stuff. Why do you want to make lots of stuff?


I don’t know what else to call it yet. When I find a better word, I’ll use a better word. Until then, I’m calling it stuff. I just mean ideas, sounds, words.

I feel best when I’m being productive. Have you ever done this thing where no matter what you’re doing, you can ask yourself, why are you doing that? What is the ultimate goal behind that?

Then you can answer that question, and then you can ask, why is that important to you? What’s the ultimate outcome behind that?

Then you can answer that question, and keep drilling down and down and down. You can call it the five why’s or whatever you want to call it, but the idea is to keep going until you get down to your ultimate core, most important value.

You have to stop before saying, “Just be happy.”

That’s the reason everybody does everything in life. Just be happy. Go one layer up from that where it’s still interesting.

I felt like I couldn’t decide between creating or learning. When it really came down to it, creating and learning are my two ultimate principles. This life coach was pressing me to decide which one is more important, learning or creating.

I thought about it for a bit and I said, “No, you know what, can we call it a false dichotomy? Maybe we’re only saying these are two different things because in English, we have two different words for them. But there might be a language somewhere on Earth where learning for the sake of creating, for the sake of learning, for the sake of creating is one long word.

And that thing would be my ultimate value, which is creating things because creating helps me learn and I like to learn things to help me create, and create to help me learn, and learn to help me create.

That thing is my favorite thing in life. That makes me happier than anything else. So, that’s what I want to do more of.


So, you’re writing for three hours a day or so I hear, you mentioned that it seems like most of your learning comes in those hours writing.

First, how do you write three hours per day?


Oh dude, it’s worse than that now. Was that on my ‘About page’ or something?


It was.


Okay. I wrote the ‘About page’ last year, it’s gotten worse since then.


Or better.


That depends. So, it’s only really in this past year that I’ve slowly realized that I’m a writer – that that’s really what I want to be. Up until last year, I really felt a programmer/entrepreneur/student of life who sometimes writes to share what I learn.

But last year, I did a little mental exercise where I asked myself, who are my heroes? Who are my idols, my role models? I listed them all out, and when I was done, I realized that every single one of them were authors.

My heroes are not entrepreneurs, they’re not musicians, they’re not billionaires, they’re not investors – they’re all authors. I thought, “This is giving me a clue here. I think who I really am and what I want to be is an author.”

Once I realized that, I really started letting go of all the other things I was doing. I just focused on being a writer.

A typical day for me now is I wake up at about 05:30. I don’t know why. There’s no alarm clock. I just naturally wake up at 05:30 every day, and I go to the kitchen, put on a pot of tea and within three minutes, my hands are on the keyboard and I’m typing.

I do this offline. To rewind to the night before, a few hours before bed, I turn off the broadband modem completely. I turn off the phone. There is no connection to the outside world. It’s just me and the offline computer.

I’ll write for a couple hours before bed. Then, I wake up at 05:30 in the morning, and I write for usually five or six hours before I turn on the internet.

Then I’ll turn on the internet, go let myself get a little distracted while I eat something – answer some emails, read a couple of little things on Hacker News or whatever like that, and then I shut it all down again.

Sometimes I just unplug the ethernet cable. I don’t have any Wi-Fi on my laptop, and that’s intentional because I want my connection to the Internet to be deliberate. So, only the ethernet cable connects me to the internet.

Whenever it’s time to focus again I’m back to writing. This break I’m talking about is 20 or 30 minutes. I’ll take maybe one hour tops if I’m going to answer emails.

Then, it’s “OK, back to writing.” I’ll unplug again, and I’ll write for another six hours until dinner time. Then maybe I’ll go to the gym or call a friend and eat dinner. Then I sit down and write for another four hours until bed. I realized that my average writing these days is like 15, 16 hours.


And is that fun?


Fuck yeah. It’s like my dream. It’s amazing. This is why people quit their jobs so they can just do what they want to do all day. I’m living my dream.

I say no to everything else. There was even some like gorgeous girl that was kind of being like flirty. She said that she’s coming through Oxford and would love to meet up, and I just said, “Nope, sorry, I’m going to keep writing.”

The weather got cold, so I went down to Portugal for 10 days and just got a little hotel room. I don’t know anybody down there. I sat in my hotel room and wrote for 16 hours a day in the hotel room. It was wonderful.


That’s awesome. I’ve gone through the process of writing a book twice now, and I found that those were often my happiest days ever – when I’m writing all day, every day.

The funny thing is I enjoy it so much, and the opportunity cost of interrupting my flow state is so high, that getting up to get a snack or even eat at all isn’t worth it much of the time because I’m so immersed in what I’m doing.

I actually always end up losing weight when I go on this writing spree, and I don’t have much weight to lose. I’m right there with you.

I see how writing can be so fun and such a joyful process.

Of all your articles, your ideas, I can’t think of one that’s cliché.

Do you have a certain method that you use to find and seek out these different points of view, Derek?


Well, you have to push past your first, second and third ideas that come to mind. The first thing that comes to mind is usually your knee jerk reaction. It’s your old outdated thing. If you ask somebody to name a famous painting, they say Mona Lisa. If you ask famous composer - Mozart. There’s always that top thing that comes to mind too quickly, so you can discard that one. That’s too obvious.

The second and third ones usually are almost as obvious. So, first, just keep coming up with options until you find one that surprises even you.

That’s fun - when you surprise yourself with an idea and you make a face at it, like “Whoa, that’s interesting.” I also really love looking at the opposite of anything, but I’ve noticed that I like the 170 degree opposite better than the 180-degree opposite because then you can keep going, like a spirograph.

Do you ever see a spirograph where you put the pen in the dot, and you turn those little gears?


Oh, I know what you’re talking about, but I didn’t know what it was called.


Look up spirograph on YouTube. I like this concept of a spirograph where if you’re going for the exact opposite of something, well then you can’t flip it again because you’re back to where you started.

But if you get the almost opposite of something, you can keep flipping and keep flipping and keep flipping. For example, let’s pick music.

What’s the opposite of music? Not the exact opposite, but the 170-degree opposite. Let’s say the opposite of music is business, and the opposite of business is charity, and the opposite of charity is greed, and the opposite of greed is generosity, and the opposite of generosity is fear, the opposite of fear is love, the opposite of love is seduction.

You can keep going like a spirograph. You get almost the opposite, and it’s way more interesting to look at things.

I picture it in a physical way. You’ve got an idea, you’ve got a topic of conversation, or somebody asks you a question. Instead of giving that off the cuff kind of answer, you pick it up and you lift it up and you look at it from underneath You look at it from all these different sides.

We kind of mentioned this earlier when you asked me if the truth is succinct, but I think the most important thing when you’re looking for a different point of view is to not try to be correct.

Don’t seek the truth just seek an interesting way of looking at it, like using a toaster to catch fish.


You don’t care about being right?




That’s a very mature stance to take. . .


Or immature. [Laughter]

I think of it more as playful. I’m not trying to be a distinguished professor. I think that it’s probably a good thing that I was never in academia.

I went to music school, and I graduated when I was 20, so I’ve never been in academia. I’ve never tried to be accurate. I’ve never been seeking the truth. I’m just seeking an interesting way of looking at things.


So, instead of seeking the truth, you’re seeking an interesting way of looking at it.


Or useful.


Useful to what?


Useful to me right now.

Let’s say I’m having trouble writing. Then it would be useful for me to believe I’m going to die next year, and this is my last chance. That anything that doesn’t get said right now is going to disappear.

It’s probably, hopefully, not the truth that I’m going to die next year, but I can deliberately believe something not true because it’s useful. Because it gets the result I want from myself.

I just picked an obvious example of that, but there are variations on that. I’m going to choose to believe this because it gets me the result I want even if the result I want is to break out of a common way of thinking.

If I’m feeling in a rut on a certain subject or a rut in my life, I need a different way of looking at it. Here’s a perspective that makes me want to jump out of my chair and go down to the gym. Well, it doesn’t matter what that perspective is. It doesn’t matter if it’s true or not. It matters if it gets you out of your chair – if gets you doing what you want to do.


I see.


Useful, not true. I keep meaning to write that article.


I like that. I’m looking forward to seeing what you come off writing about it. And it’s a great concept, it’s a totally Derek Sivers type of idea.

Totally, a Derek Sivers headline.


I have a style now? I have a type?


In my eyes. [Laughter]

It’s different. That’s your type. It’s different. It’s a great thing. It’s the opposite of cliché.

I want to talk about one of your TED Talks that you gave about keeping your goals to yourself and why it’s beneficial to do that.

I made a post about that this week – about how we live in this announcement-happy, bragging culture – where we announce even the smallest of victories and can have hundreds of people congratulate us and tell us how great we are and positively reinforce what we’re doing, even if it’s not that great of a thing.

I referenced some science and research on this. When we fantasize about this stuff, and we project this stuff out there, we’re actually far less likely to go and make it happen in real life because we trick our mind into thinking that it’s already been there, done that.

I don’t think announcing all of your goals is a good thing to do at all, but I also saw people had rebuttals like, “No, I do this all the time, and I think it’s good for me.”

Would you advise people to stay quiet until the completion of a goal, or is there a time when it’s okay to announce it?


First, I’m going to tell you a little secret before I answer your question. That TED Talk was kind of a funny situation. The way they used to do TED Talks 10 years ago – I don’t know if they still do – was that they would take pitches.

They would ask people to submit up to three ideas for a talk. For that conference I submitted two ideas that I really wanted to talk about, but there it was on the forum, the empty third submission choice.

I read a little article that morning about how announcing your plans makes them less likely to happen. I just filled in that one. I had read the article an hour earlier.

And of course, that’s the one they chose. To me, I don’t think it’s anything more than an interesting little eyebrow raiser. Two minutes of intellectual entertainment is nothing to guide your life by.

By the way, the URL on my site for the original article is sivers.org/zipit. I pointed that out because it links to Peter Gollwitzer’s original research and gives the details of his original tests.

When I gave the talk on stage at TED, I had to reduce it down to two and a half minutes. I couldn’t include any nuances. See the truth is not always succinct. This is actually a good example that the cute, succinct two-and-a-half-minute talk can’t contain the truth so much.

This thing about not announcing your goals only applies to some kinds of goals, called identity goals. Some tests found that if you told other people your identity goals, and then you got the social reward of people seeing you in a better light because of your announcement, you’re 30% less likely to do the hard work necessary to actually achieve that goal.

If you think that this applies to you, if your goal is an identity goal, a personal achievement, like I’m going to run a marathon, I’m going to lose 30 pounds, I’m going to learn Chinese, then it’s something that doesn’t need the help of anybody else.

If it’s more of you needing to do the hard work necessary to achieve something, then yeah, if you find yourself craving the reward on social media for announcing your intentions, try challenging yourself to not say a thing until you’ve actually completed it. That might give you the extra motivation to go make it happen.

But if you’re hearing this two and a half minutes of entertainment on the TED stage thinking, “Well, I don’t know because here was this one time that I said. . . “ No, of course this doesn’t apply to everybody in everything in all life.

It’s just one little tool in the toolbox. It’s a monkey wrench you can use if you need a monkey wrench. That’s how I think of all of these things.

Even all these non-fiction books offering the solution to how to live your life – I just think that each one of them is just like pliers in a toolbox.

It’s just one tool, that if you need pliers, you can use that book – that approach given in that book. If what you really need is a hammer, you can use that. If what you need is that little level thing with the bubble in the middle, then use something else.

There’s no one tool to guide our whole life.


I imagine you’ve picked up a lot of tools in your life.

How many books have you read?


I only know how many I’ve read since I started taking notes in 2007. That’s when I realized I’ve read a ton of books, and I’d forgotten more than half of them.

2007 is when I started taking notes. So, since 2007 I’ve read 310 non-fiction books that were worth writing notes about. I’ve read some where there was nothing worth writing down. I also don’t take notes on fiction books I read.

But as far as non-fiction that were worth taking notes on, I just counted the other day, so 310.


What do you think is your favorite?


I think that’s one of those questions where the truth is not succinct. [Laughter]

It’s different at different times. It’s kind of like when somebody asks, what book do you think I should read? It depends where you’re at in your life.


What’s useful to you right now?



If I had to pick right now, the book called “How to Live”, which is my next one.

I’m actually so immersed in this. When I take notes on books that I’m reading, I kind of judge a book by how many sentences I’ve underlined in a book because I only underline something if it surprises me.

I’m never trying to make a book summary. Leave that to somebody else to summarize a book. I’m not doing that.

All I do with my book notes on my site is, if while reading something, something makes me go, “Huh, that’s a really interesting idea,” then I underline it so I can reflect on it later.

I save it to a text file, so I don’t have to read the whole book again. I can just go through my notes on that book and reflect on the interesting points in that book.

For my next book called, “How to Live”, I’m setting out to make the kind of book where I’d be underlining almost every sentence. It’s basically my ideal book. I’m still writing it now. That’s what I’m working on 15 hours a day.


Awesome. You obviously you take lots of notes.

What do you think is the most important thing you’ve learned over the past year?


Probably to stop quoting.

I read these non-fiction books where every page says, this person said this, that person said, this legendary scholar is quoted as saying, blah, blah, blah. This famous millionaire said such and such.

I look at the page, and I realize that the author just shoved five unnecessary names into my mind – names that have nothing to do with the actual point the author’s trying to make. It’s noise. It’s clutter. It shouldn’t be there.

If I hear an idea and I’ve considered it and I’ve integrated it into my beliefs, I say it’s mine. I’ll say it succinctly in my own words and stand behind it, like adopting a child.

I will take care of this idea and raise it as my own, but I’ve stopped quoting.


What if people accuse you of not giving credit and even stealing like, “Hey, no, I heard this from this person, Derek.”


Sorry, I should be more clear. You don’t take the words. You take the idea. You internalize it and you really need to make it yours.

So, for example, let’s pick a famous quote. Marcel Proust has this famous comment; I’ve seen it everywhere this year. It says, “The only true voyage of discovery would be not to visit strange lands, but to possess other eyes.”

The first time I came across that quote, I thought that’s good, I like that. If you’ve considered this idea and you believe it, well then now it’s your idea.

You can say it to anybody and just say it in your own way. You don’t have to say, “well you know what Proust said.”

You only need to quote somebody if you’re going to use their exact words. But if this is something you believe now, then now it’s something you believe.

You can say, “I’ll learn more from a hundred hours in three different belief systems than I would spending a hundred hours in three different countries.” That’s one way of saying that same idea.

It’s about inhabiting different minds, not different lands. Or you could say, “I would rather see my life through Gandhi’s eyes than Gandhi’s life through my eyes.” that’s kind of the same idea.

Proust’s idea inspired those versions of the idea. It’s kind of his idea, but no, I’d say it’s mine.

Also, I find that personally, I get so much more from putting it into my own words than just echoing what someone else said.

I think it’s a kind of cowardice to just echo what someone else said. If somebody quotes someone else, you’re not really putting your ass on the line.

You’re kind of saying, “well this person said this thing, so if you want to attack it, well, hey, it wasn’t me. I didn’t say it. It’s him. He said it.”

I’d say no, take a minute, internalize it, put it in your own words, reflect it out and fucking stand behind it.


I’m going to play devil’s advocate again.

I actually listened to this specific podcast of yours, “Don’t quote, say it yourself”.

I was a big fan of it, but I do have to ask, what if someone is explaining something to you, Derek, and they say, “Oh, I remember reading this quote from a Nobel peace prize winner about how we all. . .” and then they explain it in their own words.

They just used that first piece there to generate a little bit of authority and prevent you from questioning them. [Laughter]


Nothing will prevent me [Laughter]. I know what you mean. It’s true that that’s effective. I’m not going to pretend that that’s not effective.

If you tell me Gandhi said something, well, I’ll listen twice. I’m totally susceptible to this thing. I remember even long ago, I never used to like Prince the musician, until Miles Davis said he likes Prince.

I thought, “Oh really, Miles Davis likes Prince? Okay, well now I’ll check out Prince.” So, I’m totally susceptible to this if the voice of authority says something. So, I get it.

For my minimalist tastes, I get annoyed by the conversational clutter when somebody is saying such and such, or this person who wrote this book, titled this in his book this year, said this quote.

People do that in conversation. I used to do that in conversation, especially when I started reading a lot more. I found myself quoting these books and then I’d hear myself talking to friends, and I’d say, “You know, there’s this book called “Thinking Fast and Slow”, by Daniel Kahneman.

He won a Nobel prize for behavioral economics, and in this book, “Thinking Fast and Slow”, he said. . .

I’m thought, “what the fuck was all that noise? None of that was necessary. Just say it.”

I really felt it more because there have been some non-fiction books I’ve read in the last few years when looking at the page, half of this page is just references to other people’s names. Just say it.

If I’m buying your book, I want to hear what you think. I don’t need you to echo out what others have said. Come on.


Yeah, you really throw me back.

One of the first pieces of constructive criticism I received on my first book, about two years ago, is that I used too many quotes. Not within the text, but to open a chapter after a section, and it said, “you know, Jordan, people bought the book because they want to hear you say it.”

So, I’m onboard. I see what you’re saying here, Derek. I agree. So, before we wrap up, I’ve got a couple of more questions here.

You do a lot of writing for fun. For me reading is fun too. Is there anything else that you do for fun, Derek?


Daydream. Deliberately daydream. I will very often, if I’m feeling a little burnt out with writing, just go lay down on the couch and just think of something strange.

I think daydreaming got a bad rap in school. If you were nine years old, you’d get in trouble for staring out the window and daydreaming instead of listening to what the teacher was saying. So, we tend to think of daydreaming as something we shouldn’t do.

I’ve never watched Game of Thrones or most of these shows that people talk about because if I have an hour of leisure when I don’t feel like working, I can entertain myself just fine by laying down on the couch and daydreaming about something.

I just imagine something that doesn’t exist, and then usually it ends up being some big inspiration that makes me leap out of the couch. Very often this will happen.

I’ll go lay down on the couch and deliberately sit down to just daydream, and after 30 or 60 minutes, I’m like, “Oh my god, oh my god, I just had a great idea.”

I’ll jump out of the couch. No movie has ever made me do that. So yeah, I daydream.


I was going to say that too, just seconds before you brought it up.

I’m an adamant believer that this white space, this blank space where we’re not engaged in anything is so beneficial for our minds because that’s where ideas happen often.

People don’t have ideas because they’re constantly engaged in that phone. If they’re not on the phone, they’re on the computer. If they’re not on the computer, their eyes are locked on the TV, so they never leave space for these ideas.

I’m a big proponent of what you just said Derek.

Do you consider yourself retired?


I think retired is one of those words like married, where you can be legally married or you can be essentially married. I think you get to define it yourself.

I never would’ve considered myself retired, but then I realized that I don’t work for money and I haven’t in 12 years and I probably never will again. I’ve told you how I work. I work 16 hours a day, but it’s not for the money.

Nobody pays me to do what I do, but when I think of retired, it’s an ‘icky’ word that sounds to me like giving up, like quitting or something like that.

I hate doing nothing, and I don’t hang out. I don’t sit on a couch and watch things. I don’t play golf or other games. I work non-stop, but only for myself.

So yes, I’m retired.


I wonder what retired even means, like tired again? [Laughter]


If you put new tires on your bike, it’s retired.

It’s a funny story. I never considered the word once until a visa immigration guy brought it up 10 years ago. I was entering England intending to ride my bike across the whole country.

I was coming through with my bicycle, at the Brussels Eurostar train – coming from Belgium with my bike entering England. You do the visa control stuff at the Brussels train station before you are allowed to get on the train. The guy said, “Okay, well how long are you here for?”

I said, “I don’t know, maybe a month.”

He said, “Well, what are you going to be doing here?”

I said, “Just riding my bike.”

He said, “Who do you work for?”

I have the shut-up version of the question, like if somebody sits next to me on an airplane seat, and I don’t want to talk to them. If they ask, “Oh, what do you do?” I say, “Computer programmer.”

Because people go, “Oh.” They have nothing more to say to that. Whereas, if I said I was a musician, people go, “Oh, what kind of music do you do?” And if I say I’m an author, they go, “Oh, what’s your book about?” And I don’t want to talk about any of that.

So, my shut-up version of the answer when anybody asks is computer programmer.

But then I was at visa control, and the guy said, “Oh, a computer programmer, who do you work for?”

I said, “this and that, here and there.” He said, “Well, who were you working for now?” I said, “Oh, just random things, projects.”

I was going for the shut-up answer, but he’s visa controlling, and his job is to make sure people aren’t coming in to steal someone’s job.


And Derek is super sketchy [Laughter].


Right. He doesn’t know who I am. I’m just a guy who handed him a passport. So, he says, “I’m not going to let you get on that train because it sounds to me like you’re coming in here to take a job. I mean, you’re a computer programmer, but you’re not working for anybody. You’re coming into the country for an indeterminate amount of time. It sounds to me like you’re coming here to take a job.”

I had just sold CD baby earlier that year for 22 million.

I said, “Ok look, this is a little embarrassing, but I just sold my company this year for $22 million. I don’t need to work ever again. I’m not coming to take a job; you can look me up on the internet.”

He said, “Oh, why didn’t you say so? Look, just do yourself and everybody a favor. Next time you get one of these little visa control forms where it asks your profession, write retired. Just admit you’re retired.”

I always thought of retired as meaning I’m just going to play golf and do nothing for the rest of my life. I’m 38, I’m not retired, but I thought, “OK wait. If the definition of retired is that I don’t work for other people for money, no, I don’t do that anymore.”

So yeah, technically I’m retired.


That’s a really funny story. Thanks for sharing that, Derek. I appreciate that.

On the note of traveling, I know you’ve been so many places and you’ve lived in many places.

I plan on embarking on long-term travel myself and living in places like Italy for an indefinite amount of time this year, come summer of 2020.

I’ve been planning on it for several years now, and it’s time. Things are getting to the point where I can do that.

What are some of your favorite places that you’ve lived or travelled to?


Do you already have one in mind? Are you going to go to Italy?


I think my plan is France then travel up to Italy and Germany too.

There’s a whole cluster of countries there that all border each other. I want to travel throughout, see what I like best, and go from there.

I like Israel too.


Oh, good choice. I went to Israel for a friend’s wedding once, and it was one of those places that made me want to get to know it better. That’s a nice feeling.

We spent most of our time in Tel Aviv, but Jerusalem has a really interesting contrast. I think that’d be the place.

If I was to go spend a month in Israel, I think I would get to know Jerusalem.


Yeah, I’ll be spending time there.


My main advice is to go places that are as different as possible from where you grew up. You want this to be an expanding, life-changing experience. The differences between America and even Western Europe are very subtle in my opinion. W

When you go to Japan or Kenya or Indonesia, now we’re talking.


Japan is on my list.


My advice is to go where you’ll be the most surprised. So anywhere in Asia, Africa, Russia, the Middle East. If that feels overwhelming or too much, then aim more for Eastern Europe or South America.

I don’t think you’re going to be super surprised in France, Italy, Germany. Singapore is an interesting middle ground. I lived in Singapore for two and a half years, and I’m still technically a permanent resident. It still feels like home.

My son was born there. It’s always in my heart. Singapore is an interesting middle ground where you’re in Asia, but because English is the first language there, it’s a good intro to Asia.

If you’re going to Asia for the first time, Japan is the most mind-blowing, but Singapore could be a really good home base where you can feel comfortable but still have an amazing learning experience.


Okay. Noted. Singapore’s been an attractive place as well.


It’s expensive by default, but you can get under the surface and find the cheap side.


I think Japan’s expensive too.

Do you think it’s expensive compared to the United States?


It depends where you are. There’s Kentucky, and there’s Manhattan. Are you going to do couch surfing?


I think so. I’m not going to do hotels. I’m probably going to AirBnB it, and see what I like.


Definitely go sign up at couchsurfing.org.




Even as an introvert, you’re going for the expanding your sense of self and all that, so there are plenty of people with guest cottages and guest bedrooms just completely unused. They are happy to host travelers in return for conversation.

You are an interesting dude with a lot to share. There are a lot of dead faced people that would just kind of show up and have nothing to say. You’re not one of them. I think people would be happy to have you stay in their guest bedroom for a week in Tuscany, and in return, tell them tales of famous people you’ve talked with, give them a copy of your book, et cetera.

You’d be doing them a favor and you’d be saving the $200 a night.


Yeah, couch surfing noted. I appreciate it.


Once you’ve created your profile then tell your listeners. People who have a profile on couch surfing can go in and give a little tick mark to say Jordan’s a good guy. He’s a trusted guy. So, tell your listeners once you have a couch surfing profile. I highly recommend it.


I’m a trusty fellow. Okay. [Laughter]

I’m going to play this really short game; I’m going to say a word, and you’re just going to say the first thing that comes to mind. Okay?


No. I’m totally against that!


You are?


Like I said earlier about the Mona Lisa thing – the first thing that comes to mind – I hate that.


I pride myself on being a pretty good listener compared to other podcasts, but I should have seen that in this game here [laughter].




Okay. Respect. Well, Derek, I still have one final question. I do have to thank you though. You’ve been a willing participant. This is a little bit longer than my normal podcast, so thanks for bearing with me. There’s so much that I’m curious about with you.


And that’s why I like you. I like that you’re curious. It’s a fun conversation. So, thanks.

It’s been fun for both of us, but sure, ask anything. I’m ready.


If you could teach a course at a university, a course of your creation or otherwise, what would it be?


Tech independence. Teaching regular people like non-programmers how to be free from the corporate lock-in and get off the Cloud.

I’d start by pointing out that clouds disappear by their very nature. If you’re talking a university course, let’s assume people taking the course are ages 18 to 21, so they are probably going to outlive Facebook, Google and most other companies.

Life is long. We’re talking like 80 years.


It’s probably going to be more than that 80 years from now.


Yeah. So, they shouldn’t rely on these companies for anything that matters to them. If something matters to you, don’t give it to a company.

It made me really sad. I had a friend in Singapore that, when his kid was nine years old, merged his personal and his Google apps like business Google accounts into one. Then suddenly, nine years of his family photos of his kid growing up were gone.

He emailed Google customer service, and they said no, there was the warning that when you merge your accounts. His wife was like, “What have you done?”

He has no pictures of his son from birth to age nine because he was depending on Google. You don’t do that. If something matters to you, you don’t give it to Facebook. They don’t care as much as you do.

I would teach a little class on tech independence. How to set up your own little Linux server, get your own domain name, how to host your own contacts, calendars, photos and media and the other stuff you need, definitely getting everybody off Gmail, and using you@yourname.com for your email. . .

You don’t want to entrench. You don’t want to tell everybody, “Oh the way to reach me is through this company.” That’s how you reach me, through this company that doesn’t care about me.

And so, the point is to never be bound to the corporate clouds again.

In the last week of class, here’s what we would do. It will be almost like the final exam. You do a factory reset. You bring in your phone to class and you do a factory reset.

You stick in a little pin, you pop out the SIM card, and you swap with somebody else’s phone.

If you usually use iPhone, you switch over to Android. If you usually use Android, you switch over to iPhone. Then you boot up the strange phone with your SIM card in it with no cloud sync at all. You get up and running with everything you need in a few minutes, cloud-free.

That’s tech independence.


I love it.

When I saw this on your About page on not being dependent on these companies, I thought I was the only person that thought that because I wrote about it two years ago.

We don’t know where Facebook is going to be in 50 years. My antidote was journals and photo albums. That’s the stuff you want to leave behind, but then, you mentioned something that I didn’t even think of, putting up your own server, right?


For five bucks a month, you can have your own server.

For example, a lot of people, if their first phone was an iPhone, they’re kind of stuck with iPhone because they just put their stuff in Apple’s cloud. It was very smart of Apple, very stupid of you because now you’re just entrenched.

Now, Apple starts releasing terrible, overpriced phones and you’re stuck because you depend on them too much.

I have a cheap Android phone and a cheap iPhone, and I flip back and forth every couple of weeks just to make sure that I’m never dependent on anyone.

Even your contacts – you don’t need to host those with Google or with Apple. It takes two minutes to set up your own little CalDAV and CardDAV server on your own server so that when you go to sync your contacts, you’re syncing them with yourself. You’re never telling Google or Apple who your contacts are.

Your contacts are kept privately on your own server. Same with your calendars, same with your photos. Put them on your own site, even your own file backup, you don’t use Google Cloud or whatever.

There are all these ways to do it yourself. There was a different feeling back in the mid-nineties when all this stuff first started. There was a lot more self-hosting. It was a pretty normal thing to have your own website back then.

It’s kind of sad to me that people were just told, “No, you don’t need to do that, we’ll just take care of it for you.” But now people can’t.

It reminds me of that movie Wall-E, remember with the robot in the future and people were told, “Oh, just sit in these comfortable chairs. It’s fine.”

Then, a few generations go by and people don’t even know how to walk anymore. I feel that way with tech.

It was in the best interest of a few companies to tell you, “No, just put all of your stuff with us, we’ll take care of all of your stuff.”

Well now you don’t even know how to stand on your own two feet anymore. It’s a pet peeve of mine.


I am 100% with you there, Derek. You’re the man. Thank you very much.

I really appreciate you again and listeners, I am calling his book, “Anything You Want” a must-read.

It contains all the business stuff that we didn’t even talk about today. If you are any type of business person or entrepreneur or if you have aspirations of working for yourself. . . or actually there’s a difference. If you want to work for yourself, be self-employed and leave your business for a year or two and come back to it better than it was before you left, you’ve got to read the book, “Anything You Want”.

And visit sivers.org.

Derek, I appreciate you.


Cool, thanks Jordan.


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