Derek Sivers

Interviews → Inside Education / Seán Delaney

Education and learning. Why being smart is a choice, the qualities of a great teacher, how I learn, focus, tech independence, my future projects.

Date: 2020-05

Download: mp3



Hello and welcome to Episode 402 on Inside Education. A podcast for educators who are interested in teaching. I’m Seán Delaney. I’m a teacher and teacher educator.

This week’s guest is difficult to categorize. Words like musician, author, philosopher, blogger, TED speaker, entrepreneur, computer programmer, philanthropist, circus performer could have been used at various times in his life. I first came across him when I read his short book, Anything You Want, and found it honest and insightful.

My second connection with this week’s guest is through a much-loved CD I bought a number of years ago by singer Laurie Collen. This CD had a message inside, “Your CD has been gently taken from our CD Baby shelves with sterilized contamination-free gloves and placed onto a satin pillow. A team of 50 employees inspected your CD and polished it to make sure it was in the best possible condition before mailing. . .”

Derek Sivers established his company, CD Baby, to sell his own music and later his friend’s music. The next time I became aware of Derek Sivers was when I heard him on a podcast, and he encouraged listeners to write to him. At the time, I was working on a speech for the launch of my book, and I sent the first draft to Derek, who read it and offered suggestions on how to improve it.

His website,, is a treasure trove of resources to explore, enjoy, and make you think.

In the course of our interview, we cover many topics including the single best quality of school teachers, the powerful impact one teacher had on Derek, what inspires him to create, the importance of focus, finding something that is endlessly interesting for you, and how a great teacher interrupts expectations.

I asked Derek how he would describe himself for someone who has not come across his work before the show.


Titles are like awards. You get them after having achieved something. They feel very past tense. I used to say, “I am a musician. I am an entrepreneur,” but after a while, it felt insincere. I used to do those things, but I’m not doing them now. So, my favorite answer when a stranger asks what I do is to say, “I don’t know.”

I completely ignore my past, which is really more authentic because I never think of my past. Then it makes them think I’m weird. Who doesn’t know what they do? What a weird thing to say. But it leads to more interesting conversation.

But in short, I also say that I write pop philosophy.


What’s the difference between pop philosophy and philosophy?


Philosophy sounds serious. It sounds old and ancient and takes itself far too seriously. Pop philosophy sounds digestible, useful, and accessible


How did you end up in Oxford, England?


I left the United States 11 years ago, hoping to never go back, but really, Oxford was just a smart international place to raise my kid.

Honestly, Singapore or Geneva were my first choices. But Oxford was a nice compromise with his mom, who didn’t like Singapore and felt that she didn’t want to learn another language. So, Oxford, it was.


In your view, what are schools for?


Hopefully, a place that encourages you to be smart. I think we all have the ability to be smart and to be stupid – to think carefully or not think at all. A lot of it depends on our environment.

When I think back to my teenage years, I used to be in a stupid circle of friends who would smoke pot, hang out, and do nothing but make dumb jokes and say stupid things. That environment encouraged me to be stupid because that’s what was rewarded.

But when I’m in an environment where people are being smart and actually rewarded for deep, deep critical thinking, it rubs off on me. It makes me want to ask better questions and challenge assumptions and go beyond the first answer and all those things that hanging out with your drunk friends don’t do.

So, I hope that’s what schools are for. I’m not sure, though. My kid just turned eight and he was in the best school in Oxford. But the school shut down two months ago and now he’s learning more at home than he ever did in school. He’s really thriving now. I’m not really sure what to make of that or what schools are for. I was hoping you could tell me.


When you say he’s thriving, what is stronger about his learning style now versus at school?


He seems more into it. His mom and I are making projects for him that he finds it more intrinsically interesting. We’ll pick a person he finds interesting and dive into that person’s history, and then he’ll write a report on what he learned. I played him this one Bob Marley song he liked called “Buffalo Soldier.” He said, “What’s a Buffalo Soldier?”

I explained to him what the lyrics were about. I taught him what these lyrics meant. Then he really wanted to know more about the song and about Bob Marley, so we ended up watching a 90-minute documentary about Bob Marley and reading all through his Wikipedia page. Then he wrote a paper on what he learned about Bob Marley. Pretty soon, he was doing a role play for school.

He got dressed up as Bob Marley to describe why Bob Marley was important. He said that it wasn’t just about the music, it was about the way that he brought people together. He’s really into that and thriving. Maybe because it’s just the three of us now. We’re doing things that he’s intrinsically interested in.

We’re giving him books that he wants to read instead of forcing him to read something that he’s not into. Personal feedback is also important. We are going through the times tables, and we can see that he’s got this. We can skip past this. Let’s focus on this bit that’s not coming as easily to him. He’s more engaged and learning more than he did in school.


Does he seem to be taking initiative more and following his interests more?


Yeah, he’s finding that intersection with his interests. Not just his interest of shooting arrows at the side of a wall [laughter], but his interests mixed with our nudge towards something that would be a learning and growing experience for him.


What is your vision of an educated person? When you think of an educated person who comes to mind for you.


Educated is past tense. That implies to me that you have been educated. You have completed the assignments. That’s all.

I know some very educated people who are not smart. Most people only think when they’re forced to. They did well in high school, so they got into Harvard, graduated, and haven’t done any thinking since. I actually know three different people that went to these fancy Ivy League schools and haven’t done a minute of thinking since.

To be an educated person is not impressive to me. I think anybody can be educated just by following orders. But to be smart, to be a critical thinker, to challenge assumptions, to look past the obvious, and to question the world, that’s impressive and doesn’t require that you have been educated.

An hour ago, I was listening to an interview with Naval Ravikant. I don’t even know his educational background, but he’s a shockingly smart thinker. Nothing he says sounds like it was coming from any kind of, “education.” He’s in his 40s or 50s, and I doubt any of this came from when he was a teenager in school.

I’m 50 now. Schooling was decades ago. Educated seems to imply teachers and being taught with assignments and such.


I suppose some people might think that if you downplay the idea of educated and up-play the idea of smart, that’s not malleable. It implies smart is something you have or don’t have; whereas, educated is something that you could actually achieve.


Oh, no, sorry. I don’t want to give that impression. Smart is something you do. It’s not something you are. I don’t believe that anybody is smart or stupid. It’s a matter of somebody being smart or being stupid.

I actually don’t believe there are any stupid people. It’s people who are being stupid, who are deciding on a moment to moment basis not to think, not to challenge your assumptions, to jump to conclusions, or to go with whatever first impulse comes into your head and without challenging it. That is being stupid.

What’s the opposite of that? Critical thinking. Challenging assumptions. Looking past the obvious. Questioning the world. That’s being smart. It’s definitely not a fixed thing.

Your first question asked me how I would describe myself. I said that titles are like awards. They are past tense. That’s how I think of the word educated. It’s a past tense thing. That’s just something you did.

Like when somebody says that they’re well-traveled. That doesn’t impress me. Any idiot can get on a plane and go somewhere. That doesn’t take any skill. Almost any idiot can show up to school and complete the assignments, but it doesn’t mean that they’re smart or going to be smart. A lot of people complete the assignments, but then go through their life in a stupid way.


So, the idea of “resting on your laurels” is alien to you?


Yeah [laughter]. Familiar to me, but undesirable.


Has any book you’ve read particularly influenced how you think about teaching or learning?


Not any one in particular.

If you go to, I’ve been doing a project since 2007 where I take detailed notes on every book I read. I underline or circle every sentence or idea that I find interesting and want to reflect more upon later. I do this for my own sake.

At first, I kept them privately on my computer, but after a few years, I decided to share them. Now, it’s an ongoing process. You’ll see 300 something books I’ve read since 2007 with detailed notes on each. Those books collectively have been the biggest influence on me by far. But not any one book in particular.

I think it’s because the subject of teaching and learning is one of my favorite subjects in the world, which is why you and I are having this conversation.

Of the hundreds of books listed, there are many that are directly about learning. But there are also many that are indirectly on that subject, so that’s why I think that they’ve all influenced me a little bit. But there isn’t one key book that changed everything for me on it.


I can really recommend that list because it certainly has influenced my reading over the last number of years. You rate them on a point scale out of ten and it’s really useful.

Who do you consider to be a great teacher or educator? What would the qualities of such a person be?


I think about interrupting expectations.

If you ask the class, “What’s one plus one?”

When the class answers, “Two,” you should say, “You didn’t ask me one of what. One drop of water plus one drop of water doesn’t make two drops of water. Always ask for more information. Never rush to an answer.”

If a teacher said that to me, she’d be a great teacher. Because a great teacher is someone who teaches a mindset and not someone who just delivers information. Anybody can deliver information, but I would love a teacher who helps deliver a mindset of questioning assumptions and interrupting expectations.

It’s teaching the students how to carry on and learn on their own. Teaching students how to be smart out in the world and outside of the classroom. If you’re just sitting here taking in information, anybody can do that. That’s not being smart.

Being a great teacher is to teach others how to go out into the world. Think deeper and challenge. Go beyond what’s necessary. Ask better questions.


I like the water drop example you gave. Can you think of any other examples?


When I was around eight, I started learning algebra and I didn’t like it at first.

I said, “Why is it always X and Y?”

My algebra teacher said, “I don’t know. That’s just what people do.”

I said, “Could it be anything? One cat plus two tin cans equals this?”

She said, “Yeah, it can be anything.”

I said, “OK, from now on, on my homework, instead of X and Y, can I just make it anything and draw pictures if I want?”

She said, “Yes,” and I thrived. From that point on, algebra became fun to me because she just helped teach me that you don’t have to copy the example. As long as you get the gist of the idea, you can get creative within it. That changed everything for me. I ended up being a little math whiz who went on to be a state champion in math. It was partially because of her giving me that freedom to understand that it wasn’t just rote copying.


All she did really was just stand back and let you follow your instinct.

Was there a teacher apart from her who had a significant impact on you?


Oh, yes.

Kimo Williams has a massive influence on me. If you want to read the full story, go to

I was 17 years old, living in Chicago. I was about to leave for my first year at Berklee College of Music in Boston. I met Kimo through circumstance about five weeks before I left. When I mentioned that I was about to attend to Berklee, he said, “Oh, really? I have a theory that you can graduate school in two years instead of four and I can help you do it. I used to teach there, and I think that their pace goes much slower than is necessary.”

So, Kimo and I did a crash course of five private lessons at his house over five weeks. In those five lessons, he taught me four semesters of harmony and arranging and music theory classes so that when I arrived at Berklee School of Music on the opening day, I tested out of six semesters of required classes. He taught me all of that information in five lessons.

The meta lesson here was that I can learn way faster than schools usually teach. Schools have to teach at a pace where the slowest students can keep up. But if I’m driven, I can go way faster and further.

When Kimo taught that belief system to me, everything changed.


What’s your view of the work of public-school teachers?


I admire all of their patience. It’s so hard to wait for a student to figure out the answer themselves instead of just telling them. I find that really hard when working with my kid.

Since we’ve been homeschooling these last couple months, it’s so tempting to just give him the answer. Instead, you have to wait for them to figure it out. My main view of public schools now is that I’m in awe of their patience and I’m thankful for it.


Did your interest in music come from school or did it come from somewhere else?


It helped that my mom made me take music lessons starting at age six. It was non-negotiable. Piano, viola, clarinet – I got to choose, but I always had to be taking something. If I said I was sick of piano lessons, she’d say, “OK. Then pick a different instrument, but you have to play something.”

I played the clarinet from the age eight until seventeen, but when I heard the song Iron Man by Black Sabbath, I was like, “Oh yes, I need that.” I fell in love with that sound of heavy metal.

Then, I bought myself an electric guitar and a distortion pedal, and I thrived. I quickly became the best guitarist in school. Everyone was in awe of my mad guitar skills, and I think it was probably because I had been playing music since I was six years old. Even though I played the piano, viola and clarinet, it gave me a foundation so that when the intrinsic interest in guitar came, I was already well prepped.


When your mother insisted on you taking music lessons, was it because she recognized your interest in music, or did she strongly believe in music? If you had been interested in art or a sport, would she have directed you towards that?


No, I get the impression it was just something she believed was a rule of the house. My parents said kids need to take music classes and that’s that.


How much of your education was conventional and passive? When did you start taking control of your own education?


Great question.

Once I started to actively choose learning, it was night and day. I almost failed high school. I was terrible at the passive work. I had no interest in classes like English Rhetoric. Teachers kept saying, “This is going to help you get into a good school.”

I sat in the back of class with long hair and my heavy metal t-shirt thinking, “I hate you. I hate this subject. I’m not going to a normal college. I’m going to be a musician. I don’t care. I already know what I want. I don’t care about this,” so I almost failed. I had failing grades on homework assignments because I would blow it off, but I would get an A on the test. So, the two averaged out so that I didn’t actually fail the class, but almost.

After high school, when I got to finally choose my own path and decided I was going to pursue nothing but music, I massively excelled. Not just a personal intrinsic zoom of motivation, but I also was at the top of the class and always going above and beyond whatever was required. I actually loved it when my teachers would assign things like re-harmonizing a jazz composition – something that was out of my realm – because I realized that it all benefitted me in my goal as a musician.

I wanted to kick ass at whatever they assigned me, and I did. The teacher would assign the class to write one eight-bar composition by next class and I would go write three eighty-bar compositions. I loved taking the personal challenge to go above and beyond.

Back to your question, I had regular, old, passive schooling from age five to seventeen, but from eighteen on, I’ve actively chosen education. I’ve learned so much more since school than I ever learned in school. I’m 50 now. I graduated university when I was 20, so for 30 years I’ve been out here learning, and my love of learning didn’t come until after high school.

I see school as covering the downside, instead of serving the upside. For kids who don’t know what they want, school keeps them at a baseline capability. But for those of us who know what we want, school feels just like a little steppingstone. It’s not the point.


When did you realize what you wanted?


The song Iron Man [laughter].

Once I heard that song, I thought, “This is what I want. I’m going to be a musician.” I’m so thankful for that. It’s so useful to have something – anything – for a kid to pursue. It really doesn’t matter what it is. Because in pursuit of being great at that one thing, you learn everything else as a side effect. You learn how to learn. You learn how to improve. You learn how to practice. You learn mastery. Just by having something that you’re into.


You see a meaning for what you’re doing.


It gives all of the other learning meaning when you can now apply it to this thing that you intrinsically want and that you’re driven towards.


How well did your education prepare you for being an entrepreneur?

Because that is an important part of your life. The founding of CD Baby.


It didn’t at all. I feel bad when I hear people who say that they want to create a business, so they’re going to go get an MBA or a degree in business. What’s taught in business schools is often how to be a business consultant, and how to be an employee in the middle of things.

How to be an entrepreneur? I don’t know of anybody teaching that. To anybody listening or reading, if you want to correct me, email me and tell me who is teaching entrepreneurship successfully. That would be great.

Entrepreneurship is very holistic and people focused. It’s very much about psychology. It’s very much about having to think of things from the other person’s point of view. It’s very much just being out in the world and remembering the customer’s point of view.


You’re focusing more on the other person?


Client, customer, partner, any of these. It’s dealing with other people and learning the psychology of other people, even all the people that you network with. Networking is kind of an icky verb. But networking, knowing a lot of people, keeping in touch with them, not just for your own selfish interests, but in finding some mutual interest with all these other people, that’s where a lot of these things we call “lucky breaks” happen. You’re constantly out there and staying at the forefront of people’s minds.

Being an entrepreneur is often about being out in the world with no rules and no system. It’s about making your own rules and system and finding a way to do what nobody else is doing. It’s not about a formula, it’s about being resilient when the tough times come. It’s about being super flexible.

Day to day, you have to change your plans accordingly. You have to listen when you get feedback from the world saying they want this instead of that.


Learning is very important to you. When did you consciously find that out about yourself?


I was very ambitious, so I saw learning as a key to my success. Originally, it was the key to be a successful musician. Later, it was the key to running a successful business. Then, at the age of 40, after I sold the business, I lifted my head up and got interested in other things in life.

But until that point, learning was always important to me because it was a means to an end of success for something that I was already focused on.

Now, I just love having my brain tickled. I love learning a new way of looking at things, a new perspective. I love being surprised. Since my 40s, I’ve loved learning for its own sake.


Do you think that you had to mature in order to look at learning from the more personal way?


When I was younger, I couldn’t have because it was too vague. I’m glad that my younger self was narrow minded and focused. I felt bad for my classmates who didn’t know what they wanted and just drifted into a normal, boring life because they had no target or focus. They were ambivalently out there in the world saying, “I guess I’ll send out my CV and try to get a job somewhere. I know this place will hire me. I guess I’ll do that.”

I feel bad when I meet those people 10 years later. I went to one high school reunion and I was a full-time professional musician at that time. They were only 28, but they looked like they were 50. They’re wearing suits and ties and working some dumb job. I thought, “Wow, what happened to you people?” That’s when I realized, “Oh wow, this is what happens when you don’t have a focus. You’re just adrift and doing nothing.”


In the world, there’s an infinite number of things to learn. How do you decide what to learn?


I’m still quite focused on success in my current projects. Right now, I’m really into being a great writer and programmer and dad. So, that’s still what I’m focused on learning. But sometimes we stumble into things. Portugal gave me resident status through circumstance. I have a little plastic card that says I’m a resident of Portugal. So now, I’m learning Portuguese. I never would have chosen to learn Portuguese, but just because of circumstance, I’m learning the language.

It made me smile really big when you said that you like my book list. When people I admire tell me what books they love, that has a huge influence on me. Many people said the book Sapiens was great. After hearing for the 20th time that I should read Sapiens, I said, “OK. I’ll go read Sapiens,” and wow, huge surprise. Not usually my thing, but I loved it.

Similarly, the book, Cows, Pigs, Wars and Witches was amazing. Guns, Germs and Steel was amazing. I never would have read these, but just one person I admire said, “You should read this,” and so I did. Even things like Arnold Schwarzenegger’s autobiography called A Total Recall. I have no interest in Arnold Schwarzenegger. But somebody I admire said that he really liked it, and so I went, “Huh? Alright.” I read Total Recall, and it was surprisingly interesting and enlightening and inspiring.

Deciding what to learn is usually people pointers and random stumbles.


Deciding what to learn also informs your core practices and priorities.


Usually, and then sometimes deliberately spreading out another direction.

If I’ve read too many books that are purely focused on my current priorities, it gets a little boring. I don’t want to read yet another book on being a great writer, a programmer, or a parent, if that’s all I’ve been reading lately.

So, I’ll go read a book on salt just to just to spread out. I just started listening to The Odyssey translated by Emily Wilson. It’s a new translation that I’ve never read.

Tyler Cowan interviewed Emily Wilson and I heard her talking about her translation of The Odyssey. Tyler Cowen is somebody I find very interesting. I admire him. I never would have thought about The Odyssey, but because Tyler Cowan pointed me in that direction, I’m really interested in The Odyssey now.


How do you avoid distraction and maintain focus in your learning?


Look up the book, Flow, by Mihaly Csikszentmihalyi. Flow talks about losing yourself in your work in a wonderful way where time flies. The key point is that the work has to be difficult enough to not be boring. Not too easy, but not too difficult where it’s overwhelming. I think that’s the answer to how I avoid distractions. I try to keep my work in that flow state. If something gets too hard, I find a way to break it down so that it’s not too hard.

Once things get too hard, I get distracted. When I bonk my head up against something that’s too difficult, I find myself opening a browser to surf Reddit or something stupid like that. Same thing if something’s too easy. It becomes boring and I don’t want to do it. I look for distractions that are more interesting.

Maintaining focus – that usually comes from the state of being unfinished. When something is unfinished, I feel constipated. It’s physically uncomfortable. I just want to get it out. Pressure builds up. I hate when things are unfinished. I’m usually learning for the sake of creating something. I want to learn a particular subject so that I can create this thing and get it out. More than anything, that keeps me focused.


Something that’s unfinished is quite different than something that is just started.

The finish line is in sight when something is unfinished. But when you start something new, the finish line is so far away. Does that make a difference for you? Unfinished versus starting with a very steep learning curve?


I am so glad you caught that. You just caught a glimpse into my mental state right now in May 2020, where I have three or more projects that are very close to finished.

I’m feeling very “Shut up. Ignore the whole world. Ignore everything. Focus, focus, focus. I just need to finish these!”

But you’re right. I was beaming as you mentioned this different excitement and joy that comes when you first start something. It’s almost like falling in love. It’s a bounce out of bed at 5 a.m. because I’m so excited for the joy of discovery. It’s a thrill. I don’t need to try to stay focused because it’s almost an obsession. Like when you first fall in love with somebody and you’re obsessed.


Where do you let things go? You talked about learning Portuguese. Why wouldn’t you go even deeper and deeper into it? When do you let you let yourself stop learning a subject and say, “OK. I’ve gone far enough in that.”


I don’t stop myself. Very deliberately, I usually do go down the rabbit hole. But that’s OK. I’m almost always glad I did. I love that you asked how far I let things go. It’s not a binary question of “Do you go down the rabbit hole or not?”

It’s, “How far down the rabbit hole do you go?” Even reading a whole book about Schwarzenegger already puts me in the one percent of the world who knows more about him than most people.

Don’t you find that your intrinsic interest dries up after a certain point? You say, “OK. That was enough.” I’m interested in linguistics, but only to a certain point. I don’t really feel like becoming a professional linguist now, but I’m glad that I took this 30-hour course in linguistics or read these three books about it. But I don’t feel like reading 20 more.

There are those occasional things where it feels endless, like computer programming. I love it for its own sake. I find it endlessly interesting. I love doing it. I love learning about it. I love talking about it. I love programming. I started learning programming 23 years ago as a quick means to an end. I was trying to sell my CD online, so I quickly had to build a little shopping cart on my site. I had to learn a little bit of programming to do so, but then it kept going. Slowly, over many years, I found that my interest in it just kept growing.


How do you learn in general?


Books. I love the long, quiet focus of books. It also really helps to mix in as many senses as possible. Listening to things, watching multimedia videos, courses that give assignments.

In short, the more different methods, the better. You’ll have a stronger foundation if you’re learning from many different inputs and sources.


You also spoke about cross-referencing different sources. Some sources are better at explaining ideas than others.


This was so useful. Since I’m such a fan of books, and I listen to recommendations, sometimes people will say to me, “If you want to learn this thing, you should read this book. This is the one.”

So, I’ll start with that book, and it’ll be a slog. It feels uphill and too hard. So, I’ll switch to another medium. Some video, or person, or even a different book. Suddenly, it’s so easy. I just needed a different teaching method and a different focus for some reason.

Sometimes, the way one person describes something makes all the sense in the world to me. And another person teaches it in a way that makes no sense to me.

It really helps to have a variety of inputs and sources.


When did you realize that creating was very important to you?


You can probably predict what I’m going to say. Being a successful musician was my first ambition. That’s what it was all about – creating great music. And basically, the only measure by which you’re judged is by what you create. That that value system stuck with me.

I don’t like learning without creating. If I go learn a subject for 1000 hours and do nothing with it, it feels like it was pointless.

I get that it can be interesting to have your brain tickled to learn about something new for the sake of it, but I always want to turn into something. It’s almost pointless unless I’m using it to create something.


Do you have a memory of creating something that you are proud of for the first time, presumably as a musician?


Yeah. The first time I wrote and recorded a song that sounded like my heroes. That was such a great feeling. It’s one thing to write a song where you’re in your bedroom strumming an acoustic guitar. But when you actually plug it into the box, put in some layers, put some drums and a bass over it, turn on the effects, and it sounds like a real professional recording, it feels mind boggling. I’ll never forget that.


Apart from music, what do you like to create? I know you’re working on three books at the moment.


That’s my main thing. I’m really excited about writing many different books. Partially because I didn’t take my writing seriously until a year or two ago. I didn’t consider myself a writer.

I have a whole folder on my hard drive full of couple hundred things that I want to create someday. For example, I want to design and build a house from scratch. I want to make a hosting company called 100 Year Hosting where websites will stay alive after you die. There will be a trust set up where the trust will own the domain name or have rights to update it. For 100 years, or many decades after you die, your domain name and your website will stay safe and alive, and that will be your legacy after you die. I’d love to setup that system. I’d love to create the legal and technical structure to help that happen.

I have an idea called B Major. I want to set up as a place to highlight the next generation of musicians and showcase them.

I’d love to make a forest over 15 years. I want to buy 100 acres of dead land somewhere and hire forestation experts to cultivate it back into a thick forest over the course of 15 years, and then it can take care of itself.

I would love to make an app that connects those few remaining people on Earth who still enjoy talking on the phone. I feel like everybody has descended into texting. Only a few of us still prefer talking on the phone. I have an app idea called EarMouth that I want to make that is specifically for connecting those people.

I have an idea called CloudFree. It could be a site or service that teaches about tech independence because I think everybody has become too dependent on the Cloud and Google. How upset would you be if Google deleted your account tomorrow? If it would be devastating to you. You are in a precarious position because Google can and might just delete your account by accident or for no reason and there’s nothing you can do about it. So, I want to teach people how to be tech independent and cloud free.


That’s fascinating! Where did those kinds of ideas come from?


Pain and anger – what persistently angers me or frustrates me for years at a time and doesn’t end.

Some desires or interests come and go. This month, you think you might want a dog, but a year from now, you don’t. But if you find that years have gone by and you still want this thing, you should pay attention to it. Especially with anger. If there’s a certain subject that gets you unreasonably upset, pay attention to it.

It’s telling you that this is wrong, and you need to right it.

With tech independence, it makes me scared and sad for my friends who are completely dependent on cloud services. They use Gmail and put all of their important photos on Instagram or Facebook. They’re completely dependent on Google calendars and Apple’s cloud copy of their contacts. They completely depend on these companies that don’t care about them. It makes me really sad and angry to see how far things have gone that direction because when I first got into the Internet around 1994, more people were self-hosting things. It was a given that you did everything yourself.

There weren’t portals, so way more people had home pages, had their own sites, their own domain name, they made their own HTML. They didn’t depend on WordPress to do it for them. They knew how to create basic HTML. People knew what a URL was. It makes me sad I give people a URL like, and they go to a search engine and search for it.

People used to call 411 or use a phonebook to look up somebody. I see people searching Google for things that they already know the answer to. With one hour of time, people could be tech independent and not depend on these corporations that don’t care about them.

They would know how to host their own e-mail at their own domain and keep their own photos in the system and share them. They can share a copy of their photos, but never give Instagram the master copy of anything that matters to you.

Some of this worry is because when I got online in the mid 90s, there was this thing called the dot-com boom. From 1999-2002, half of every company you ever heard about went out of business and disappeared. I’m still completely expecting Facebook and Google to go out of business and disappear. So, if you’ve given them things that matter to you, it frustrates me because I expect you to live a lot longer than Facebook.

There’s my rant [laughter].


That’s great. It’s a cautionary tale because we get lured in by their ubiquity.

We think they’re there forever.


They want you to be dependent on them. Apple and Google both say, “Give us your content. We’ll take care of that for you. Give us your contacts. Give us your calendar. Give us all your emails. We’ll take care of all of that for you.” Of course, it’s in their own interest to make you dependent on them. It’s very seductive.


And it’s an invasion of privacy, but that’s another whole other area.

When you create something, how do you decide that it’s ready to be shared with the wider public?


For writing my little articles that I post, it’s when there’s nothing left to say. I usually blather an idea and then I remove every sentence I can until I can’t remove anything more. Then, it’s ready. The general answer is that if you wait until it’s ready, then you’ve waited too long. You have to let it go and release it, and remember that you’ll keep improving.

I like that the fact that we use the word “release” in English. You release an album or a book. I like the double meaning of that word. You have to let it go. You’ll always have the feeling that it’s never done. Diminishing returns, or whatever metric you want to measure, but at some point, put it out there before you’re ready.


Computer programs do this. They leave stuff for the next version.


Exactly. I think that with everything in life. I think of this in terms of e-books. If you buy the e-book from me, then you’ll get the next version for free.


I want to ask you a few questions about how education could be different.

If you could rewind your own life or be more proactive in your own child’s education, how would you like your education to have been different, or how would you like your child’s education to be different?


I have more questions than answers. In short, I don’t know, partly because my kid is only eight and I’m still learning this. In 10 years, I might have more opinions. There’s a really interesting article that I recommend called “How to Raise Your Kids to be Billionaires” by Charlie Tips. It’s hosted at He is a California investor who’s been around a lot of billionaires and is quite successful himself.

He’s watched a lot of his friends’ kids grow up and he’s gotten to know many billionaires and learn about how they got there. His article is not about the money at all. It’s more about how to raise kids who are exceptionally happy and thriving in this world.

His bullet points from the article are:

Make them aware of the full range of life options. Like I said earlier about the people who end up into some middle management role at some company. Nobody showed them that you could go start an ostrich farm or get a job on a fishing boat or whatever it may be [laughter].

It was so useful that I was in a circus for ten years. That was my full-time job from the age of 18 to 28. I was the ringleader M.C. of a circus. Everybody I knew were jugglers and magicians, and the guy who started the circus was some kooky guy from the art center who randomly decided one day to start a circus. So, he found a few kids that juggled and started his own circus. It really helped me to be around these misfits.

Charlie Tips’ next point said don’t send your kids to public school or even to the prep schools because they’re just public schools on steroids. Teach love of work and teach love of people. This was a big one.

He said, “In my household, we always had strangers coming through and staying. We lived in San Francisco and sometimes we’d meet a homeless person and invite them over to stay at our house for a couple days and get to know them. I wanted to teach my kids the love of people, all people.”

The next point was to teach generosity.

Make them teen outcasts. Nobody gets great by fitting in.

Teach numeracy because so many things in life ultimately come down to getting the real facts.

Lastly, Charlie Tips said no allowances. Don’t give them an allowance and don’t get a damn job at Burger King, but instead always encourage them to go create something and make something happen.

Create a project that makes money, even if it’s just a few dollars. That’s better than giving them a few dollars. Help them make something that earns a few dollars.

You’re also catching me at a weird time during this lockdown since schools are closed. I’ve had my expectations upended. Part of the reason I moved to Oxford is because it was known for its great schools. I thought, “This is going to be a great place to raise a kid here in this place that knows so much about education.”

It’s been really weird the last couple months to see how my kid is thriving so much more since we pulled him out of school. Since my expectations have been upended, it made me think about the How to Raise Your Kids to be Billionaires article. I keep revisiting it.


How can you scale up the kind of education you’d like your child to have?

How would you envisage to educate the number of people that our system tries to educate at scale where they’re still growing up to be, in Charlie Tips’ words, “billionaires?”


I have a tiny idea. I’ve only put a few hours of thought into it. I call it the School of Mastery. I’ve written about it on my site. It’s at I talk about a place where anyone who wants to focus on a skill of their choice and be surrounded by other people doing the same, could go to this place with a few coaches and others who are experts on the craft of mastery. They can offer help and guidance to the students.

I was influenced by Salman Khan’s proposal to flip the classroom, which is this idea that the core of learning is done as an independent study using online materials. Then you get together with the teachers after you’ve learned in order to review and for a little guidance and coaching.

The actual core of the information transfer happens privately at home and online. So, the idea is that if we assume that the best teachers of any subject have already shared their teachings in some mass way, whether it’s video courses or books or whatever, then you don’t need the in-person classroom to teach you anything.

Instead, you get the teaching through the media sources, books, Internet, videos, etc. But then the local coaches in person can help guide each student’s path to mastery in whatever subject. These people at the school don’t need to be a master in calculus, a master at the flute, a master at calligraphy. Instead, they just need to be great at guiding mastery in any subject, which is a general skill.

I still like the idea of going away to school somewhere. I don’t know about you, but when I was 17 and left to go to Berklee School of Music in Boston, it was a special feeling. There’s a sense of focus and seriousness to it. It fits the story we tell ourselves. “I am going away to this place for this purpose.” Some people do it with yoga, “I am going to India to do yoga,” or, “I am going to this health retreat to get healthy.”

It’s the same with mastery school, “I’m going away to this place where I am going to become great at this skill I want to learn.”


Would you envisage that happening at age 18, or could it happen earlier?


Whenever they’re ready.


The 14-year-old Derek Sivers could have gone to learn about Black Sabbath?


Yeah [laughter]. About music and how to be a great heavy metal musician. Different people hit that point in their life at different times.

A couple of years ago, I got really close with an Olympic athlete who found her calling when she was five. At the age of five, when she went to ballet class, right away she said, “This is it. I’m going to be the best in the world at this thing.”

And she went on to do it. Luckily, even though she grew up very rural and poor, her parents saw this in her, and they pulled her out of normal school. And from that point on, she never went to a general school.

She only went to specialized schools for professional athletes who learn basic requirements on the side while they focused all day long on their coaching and excelling at their Olympic sports.


Maybe schools need to help people find their area of specialism or mastery?


We say “find their mastery” it as if it’s hidden.

Same as talking about “finding” a great love. Like relationships, it’s something that you need to craft yourself. You need to make a great marriage and make a great relationship. Pick something to do and then you can make it happen.

That’s why I like that you asked the question about music because I think it really helped that I was forced to take music lessons for a number of years. I found my intrinsic interest in music independently, but it helped that I had a background.


You mentioned earlier working in the circus with lots of misfits.

What advice would you give a student who knows that they are a misfit in the school system and believes that they won’t do themselves justice in their school examinations? What would you say to them based on your experience of life and learning?


Sorry, the most boring answer ever is that it depends. It depends on the person.

But, before getting to know anything about that person, I would help to reassure them and remind them that school itself is not that important. You don’t need to take it too seriously. In fact, it’s probably really healthy to have a healthy disrespect for the school, and to challenge the things the teachers are saying and push back. It could be really beneficial.

Like how Kimo Williams helped me look at Berklee School of Music – not in reverence, but in order to understand that they were going to make me take four years of classes to learn something that I could learn in two years. That was really healthy for me.

So, if somebody was a misfit in the school system, I’d help reward that. I’d say, “Congratulations. Do not try to fit in with the system. It’s all bullshit anyway. If you can see that, then you can use it to your advantage. Be the boss of your own learning instead of seeing yourself as the slave to their system.”


Derek, that’s fantastic. Thank you so much. I know you have three books coming out. Do you want to say a little bit about the books, about how people can contact you if they’re if they want to hear more?


I don’t need to talk about the books.

But if you go to my site,, my favorite thing is when people introduce themselves. I put myself out there like this is because I love finding the people who find me. So please click my email address on the site. I respond to every single one. I enjoy it. Send me an e-mail, say “Hello,” and ask me anything or just introduce yourself.