Derek Sivers

Photo of the writer Derek Sivers making a face and showing his teeth
Derek's profile image on X.
Foreword 2025-04

https://sive.rs/

Derek Sivers has written lots of interesting bite-sized articles on his website, and also collected them into books and presentations. He got rich from selling an early internet age company but gave away almost all of the money, and continues to do so with the book sales.


2018-02

https://sivers.org/kimo “There’s no speed limit”

I was seventeen and about to start my first year at Berklee College of Music. […]

When the studio owner heard I was going to Berklee, he said, “I graduated from Berklee, and taught there for a few years, too. I’ll bet I can teach you two years’ of theory and arranging in only a few lessons. I suspect you can graduate in two years if you understand there’s no speed limit. Come by my studio at 9:00 tomorrow for your first lesson, if you’re interested. No charge.” Graduate college in two years? Awesome! I liked his style. That was Kimo Williams. Excited as hell, I showed up to his studio at 8:40 the next morning, though I waited outside until 8:59 before ringing his bell. (Recently I heard him tell this same story from his perspective. He said, “My doorbell rang at 8:59 one morning and I had no idea why. I run across kids all the time who say they want to be a great musician. I tell them I can help, and tell them to show up at my studio at 9am if they’re serious. Almost nobody ever does. It’s how I weed out the really serious ones from the kids who are just talk. But there he was, ready to go.”)

He did graduate in roughly two years.


https://sivers.org/gifts “Why I don’t want stuff”

I live in a little pre-furnished apartment with no stuff, and I love it this way. I have no books, knicknacks, decorations, and really no personal items at all. Just some minimal clothing, my laptop, headphones, and not much else. All the kitchenware and furniture just came with the place, and will stay here when I leave. I just moved into this place a few weeks ago. I’ve moved every year or two since I was 17. I do it because I can, and living this way makes me happy. Every year, I erase my computer’s hard drive and re-install my operating system from scratch. Every week, I erase my phone’s log of texts and calls. I just love that uncluttered feeling.

It makes me really happy when another Christmas or birthday has passed and I didn’t receive anything.

I love people one-on-one. When not answering emails, I’m often talking on the phone with one of my dear friends across the world, getting into great conversations for hours.

In fact, I’ll tell you a secret. For most of those interviews at sivers.org/i, they sent me their questions a week in advance. I’d spend hours writing down answers from different perspectives, before choosing the most interesting one. Then once we were in a live conversation, I’d try to make it sound spontaneous.

It’s a common belief that your first reaction is the most honest, but I disagree. Your first reaction is usually outdated. Either it’s an answer you came up with long ago and now use instead of thinking, or it’s triggering a knee-jerk emotional response to something that happened long ago.

All these blog posts are so wonderfully concise.

[…] spending 12 hours writing an article, saying everything on my mind, then editing it down to only the words that are really needed.


https://sivers.org/horses “My favorite fable (塞翁失马)”


https://sivers.org/counter

So my public posts are a counterpoint meant to complement the popular point.

The best and most effective changes I’ve made in my life seemed crazy at first, because they seemed to be over-compensating.


https://sivers.org/my-fault

It felt so good to decide it was all my fault! This is way better than forgiving. When you forgive, you’re still assuming they’re wrong and you’re the victim. You’re just charitably pardoning their horrible deeds. But to decide it’s your fault feels amazing! Now you weren’t wronged. They were just playing their part in the situation you created. They’re just delivering the punch-line to the joke you set up. What power! Now you’re like a new super-hero, just discovering your strength. Now you’re the powerful person that made things happen, made a mistake, and can learn from it. Now you’re in control and there’s nothing to complain about.


https://sive.rs/tvtest

It’s actually impossible to fail if your only mission was to see what happens!


https://www.ted.com/talks/derek_sivers_weird_or_just_different

In Chinese there are doctors who think it’s their job to keep you healthy. So they take payment when you are healthy, but when you are sick you don’t have to pay.

He also had the example of Japanese using block and building numbers instead of street names:

For an American blocks are the empty space between streets, for a Japanese streets are the empty space between blocks.


https://sivers.org/about

My own self-created philosophy lined up almost exactly with an ancient philosophy called Stoicism.

Nobody gives a novelist shit for writing alone. But an entrepreneur, programmer, or musician is expected to collaborate. I disagree, for me. I prefer the life of a novelist, whether I’m writing code, music, or systems.

12 hours a day works best for me, about 6 days a week. It’s good to break the gravity one day a week, and force myself to do something else. I resist it at first, but appreciate it afterwards.

Besides my “work”, I write in my journal up to three hours a day. Reflecting, daydreaming, planning. Asking myself questions, and trying different answers. It feels like all my learning happens here.

Two of my best friends right now, I’ve never seen in-person. One lives in Hong Kong. One lives in Lithuania. We’ve been talking on the phone for years, but never met in-person. We don’t even video-chat. Just voice. That’s all I need. (Because of this, I loved the movie “Her”.)

It occured to me that maybe he preference to talking may be linked to his musical background. Myself, I feel most comfortable chatting on computer, where it’s easy to control the pace of conversation and do research before blurting out dumb things. I too really prefer to chat one-on-one.

I got online in 1994, so I watched many companies — companies that people were completely dependent on — go out of business, and watched everyone’s uploaded stuff just disappear. So I don’t trust companies, I avoid the cloud, and run everything myself on my own server.

I’m not into family. Man, I catch a lot of shit for this. I don’t hate but don’t love my family. They’re fine. I just never felt that close to them, even as a little kid. I don’t subscribe to that “blood is thicker than water” metaphor. I feel pretty equally connected to everyone. (We’re all cousins, anyway.) I don’t feel more bound or obligated to my immediate family than I do to strangers. In fact, because of my ambitious exploring nature, I’d rather focus on the unknown, and push further out into the world. All of my relatives, every single one of them, live basically right next to each other in Portland Oregon. I’m the black sheep.

I don’t like live music. (I know that is a very despicable opinion.) I love great recordings. Like my preference for one-on-one conversations, my relationship to a piece of music is personal — it’s between me and the music. I don’t want to have a bunch of other people around, and don’t want to be distracted with other things when listening. Ideally, instead of a one-to-one relationship between listener and musician, it would be one-to-zero, where I can’t even know who the musician is. Then I could focus just on the music itself, and not be distracted by any personal information about the musician.

Agreed but I also feel this way about any media — watching TV or anime with friend, expecting to be asked for opinions or judged for my reactions distracts me from my need to deeply connect with the work.

My present life is in service of my future self. I tend to do things for my future, not my present.

I feel the precious value of time, most of the time. I imagine my time as worth $500 an hour, and ask myself what’s worth $500. Watching a TV show? Absolutely not. (“Game of Thrones” at 63 hours so far = $31,500 to watch.) Social media? Absolutely not.

Use this rule if you’re often over-committed or too scattered. If you’re not saying “HELL YEAH!” about something, say “no”.


https://sivers.org/career

So instead of looking for passion and purpose, just keep mastering whatever work you’ve started, becoming more and more valuable in your field. Passion and purpose will follow a great career.

Think of ways you can use the value you’ve built up to make the transition to another field.


Seriously, what the hell, I don’t think I’ve ever identified this closely with a person on the internet before. Nearly everything he says feels quotable and not being said by anyone else. Maybe I’m over-quotating today, but whatever.


2018-02

https://sivers.org/jp14 “Understanding Japan”

Honne (本音) refers to the opinions and true feelings that everybody has.

Tatemae (建前) refers to social obligations, and opinions that have been adjusted to be socially acceptable — when words and true intentions don’t fully coincide.

What someone really thinks is “honne”, but what they actually express is “tatemae”. In Western countries we could call it hypocrisy, but in Japan knowing how to express tatemae and honne at the right time is considered a virtue.

Imagine you want to buy a ticket and there are no seats left. The ticket salesperson won’t give you a straight answer like, “There are no tickets left.” Instead he will probably keep you waiting, pretending he is looking into something on his computer, make weird faces, and say something like, “Finding seats can be difficult.” This is tatemae at its best.

In individualistic societies (America, Europe, Australia, etc.), the common belief is that if you pursue your own self-interest this will automatically help with the interests of your society. In Japan, the belief is reversed. If you give your utmost in your work to serve your company, customers, and society, then this will automatically serve your own self-interest.


https://sivers.org/wds “Uncommon Sense - live at WDS”.

He’s a phenomenal presenter as well.

We imagine everyone we see on the screen has to be rich, right? It blew my mind when I learned the richest actors in Hollywood are people you have never heard of, because they optimized for money instead of fame.

This presentation is from 2015, quite good call:

Donald Trump has chosen to make less money and optimize for legacy

In your grand business strategy, commit to a problem rather a plan to solve one, as no plan survives the first contact with the customer.

You want us change the album cover, okay, no problem, just send us a pizza. - Sorry? What? - Yeah just call this local pizza place and tell them you want to order a pizza for CD Baby, they know us, they’ll know what to do. - Ehh, uh, sure I guess. Thanks.

He then goes on to explain that the real point of asking for pizza in exchange is that it humanizes the business. Earlier he told how the most (anti) “revolutionary” thing they did was to answer people’s phone calls, and another thing he did as a joke was to make all their email responses address the recipient in a silly way.


2018-02

https://sivers.org/obvious

Everybody’s ideas seem obvious to them. So maybe what’s obvious to me is amazing to someone else?

Your public persona — the image you show the world — should be an extreme character. It can be a version of yourself, or it can be a mask. (It’s easier to be honest behind a mask.) Some of the biggest music musicians of the last few decades have admitted that they were playing a character. Eminem, for example, said he wrote lyrics with the main goal of shocking a passive listener into paying attention. Then he built his public persona to match the lyrics.


https://sivers.org/bronze

Imagine what it’s like to be the silver medalist. If you were just one second faster, you could have won the gold! Damn! So close! Damn damn damn! You would keep comparing yourself to the gold winner, full of envy. Now imagine what it’s like to be the bronze medalist. If you were just one second slower, you wouldn’t have won anything! Whoo-hoo! You would be thrilled that you are officially an Olympic medalist, and got to stand on the winner’s podium at all. Comparing up versus comparing down. Your happiness depends on where you’re focusing.


2019-02

https://sivers.org/aos

But his mother was on her death bed. An undiagnosable illness seemed like it was going to take her at any time. All of her children were visiting her every day. When he mentioned that he got accepted to the art school in Vienna, everyone said, “Well of course you can’t go! You need to stay here with your mother during her final days!” He was very conflicted and felt horrible about this, but still felt that he had to accept the offer. So he moved to Vienna. His mother disowned him. His brothers and sisters screamed about his selfishness, and didn’t speak to him for years. Everybody told him what a horrible person he was. David told his story at the age of 38 and said, “And now, 20 years later, my mother is still alive. I’ve followed my dreams, had a great career and an amazing life, while my brothers and sisters have given up their whole lives to stay by my mother’s bed, still to this day.”


2025-08

https://sive.rs/htl00

Every now and then, I hear someone quote it. When they do, I think it’s the most beautiful quote I’ve ever heard. Then I remember I wrote it.

I feel I’m not supposed to admit all of this. But it’s honest.

Why don’t more writers feel this way?


https://sive.rs/dxb “I hated Dubai until I learned about it”

Dubai was in my “Top 5 places where I NEVER want to go”. […] Last year, when I was booking a flight to attend a conference, there was going to be a short layover in Dubai. My first thought was “yuk”. But when I notice I’m prejudiced against something, it makes me curious. So I made it a 3-day layover, to see Dubai for myself.

Dubai the city is in Dubai the state, which is one of the seven emirates of the U.A.E. Abu Dhabi is the biggest emirate, and Abu Dhabi the city is the capital of the country.

See, Abu Dhabi has 95% of the oil, Dubai only has 4%, so Dubai had to be smarter, more competitive, and attract business to thrive. Sheikh Rashid was thinking long-term, had a vision of Dubai’s huge potential, and invested everything into its development in the 70s, even against his advisors’ advice. It seemed crazy at the time, but paid off in a big way 15-30 years later. It was quite entrepreneurial.

Before flying to Dubai, I contacted a Saudi guy I met once in England. […] I emailed him to say I was coming to Dubai, asking if he’d be around to meet. He replied, “My friend! Cancel your hotel! You will stay at my home in the Burj Khalifa!” I said, “Wow! Thank you. OK. It’ll be great to see you.” He said, “No, I won’t be there. I’m in Riyadh. But my uncle will pick you up at the airport and give you the keys, so you can stay as long as you like.”

I’ve lived in New York City, London, Los Angeles, San Francisco, and Singapore. I love how multi-cultural they are. But nothing like this! Those cities are about 35% immigrants, whereas Dubai is almost 90%.

He said, “From the desert, but then two uncles got in a fight, splitting the family, and half went to Iraq for a while. They reunited in Abu Dhabi, but then Islam came along…”

I interrupted, “Wait. Islam came around the year 620. Have you been telling me your family history from two thousand years ago?”

[…] He shrugged, “We keep good records.”

(I’ve asked other Emiratis since, and they all seem to know their family history this far back.)


https://sive.rs/mystery

Use obscure references in your lyrics. Produce unusual sounds in your recording. Make strange images in your photos and videos. Give just enough to make them curious. Let them search for explanations, clues, or context.

Maybe due to social media, artists are less mysterious than ever. It’s kind of sad to have everything so transparent. Once something is explained, it stops captivating your curiosity.