Derek Sivers

Interviews → Transformative Principal / Jethro Jones

On education, parenting, and encouraging focus

Date: 2020-05

Download: mp3



Welcome to Transformative Principal. I’m your host, Jethro Jones.

I am very excited to be talking with Derek Servers, an entrepreneur who founded CD Baby and has written a few books. My favorite book that he’s written is called Anything You Want: 40 Lessons for a New Kind of Entrepreneur. He is now writing and doing cool things.

Welcome, Derek, to Transformative Principal. I appreciate you coming on.


Thanks, Jethro. Thanks for having me.


I’m excited to talk to you because you have taken a different path. You have a son that you’re home schooling. Is that correct?


As of a couple of months ago, yeah.


Yeah, like we all are.


Right, exactly. But before that, no. The reason we moved to Oxford, England from New Zealand was for the schools. Up until two months ago, he was in one of the best schools in all of England for his age group.


That’s very exciting. One of the things that you’ve written about is the idea of giving your son your full attention and letting him lead the way in the things that you’re both doing, especially with creative play and things like that.

Can you tell us about how you view parenting and educating your kids? Not just educating as in sending them to school, but also teaching them the things you really want them to know?


First, I have to give this caveat that he just turned eight. I still feel like I’m really new at this. But maybe ask me in 20 years, I’ll have more authority on the subject and more to say. But as of now, I’m just beginning to dabble in this.

My approach to parenting has been to encourage focus and encourage him to dive deep into whatever is interesting him. We only moved here to England a year ago, so he spent age zero to seven in New Zealand, which means he grew up mostly outside. And that really shaped him in a big way.

For one, we often went to the beach or the forest or just a grassy field and play there for hours and hours. For five hours we just saw in one spot playing with shells, playing with driftwood, making little things out of leaves and sticks and whatever.

I always wanted to make sure that we did everything for as long as he was interested in it. I never said things like, “Come on. We need to go.” I wanted him to learn that whatever he’s into, he should keep going over learning, “Well, I’ve been doing this for 30 minutes or 60 minutes. I should stop.”

Sometimes I worry that the pace of school teaches the latter. Like every 60 to 90 minutes, we should change subjects.

It’s similar to watching a Hollywood movie. We expect it to be somewhere around 100-110 minutes. If it goes much longer than that, we think, “Oh, come on, what’s going on? This movie so long.”

I wanted him to dive into whatever he’s into for as long as possible.

Also, I want to broaden his inputs. While we’re playing with Lego, I’ll play some really avant-garde Bulgarian or Indian music, and just let those sounds soak into his mind and open his ears.

But all of that is just parenting. I guess education’s different subject.


Well, I think that they’re closely intertwined.

Why was that important to you to start while he was so young?


It’s personal preference. I feel that if you’re focused, you can do anything. If you’re not focused, you can’t do anything good. That’s my own value system. There are other things too, like empathy and consideration.

There’s a really sweet story. When he was two or three years old, we were out playing in a playground somewhere and a kid fell down and started crying. I think his parent wasn’t hovering over him so I said, “Oh, hey, that kid fell down. You should go give him a hug and tell him it’s OK and try to help him.”

He went, “OK!” He ran over there and put his arm around this kid and patted him on the back. He said, “It’s OK. It’s OK. Here, I can help you.” It was so cute to see my little two or three-year-old doing that, but it was because I told him to.

And then I think one more time, maybe six months later that kind of situation happened again. Some kid was sad and crying about something. I said, “Oh, look, he’s crying. You should go put your arm around him and help him.” He said, “OK,” and he went running over there to help.

And Jethro, ever since then, since the age of three or four, now, he just does it automatically. Any time he sees anyone get hurt or sad anywhere, he immediately rushes over and puts his arm around them and say, “It’s OK. It’s OK. Can I help? It’s alright. Are you OK?”

It’s amazing that I can see that direct link from two specific examples where I encouraged it and now, where it’s a habit. Even at this age, he still does it. A few months ago we were at a coffee shop and a kid leaned back and fell out of his chair. And even though his parent was right there, as soon as the kid fell out of his chair and started crying, he jumped up out of his seat, ran over there, put his arm around him and said, “It’s OK. It’s OK.”

Wow. It’s so cool to see that. I wish I could consistently do even more things to encourage the values that I think are important.


That’s really great. I’ve seen with my own kids similar things that you when you teach them how they should act in a certain situation, they’re more apt to act that way in the future.

I want to go back to that piece about focus because that story of empathy made me think about an example in my life that’s happening right now. I come from a musical family. My mom plays the piano and organ beautifully. Her grandpa created a school of music in Salt Lake City a hundred years ago and it was very successful. I took piano lessons when I was a kid, but then didn’t like it because I was being forced to do it. That’s how I feel because I’m rebellious by nature. I didn’t like them pushing me into that.

I’ve wanted my kids to be into music also and realized that I need to set that example and say this is how I’m choosing to spend my time. Not how I think you should spend your time – like you must do it or else you’re grounded. Like you can’t go out and play until you practice piano. Because that for me, never worked.

I started playing this year and have been practicing every day. We have a keyboard in the house and I’m using an app to teach myself. And it’s been really cool to do that. But then I’ve noticed how my kids are starting to do it as well and they practice, Derek, more than the “required thirty minutes per day” that I had when I was a kid. It seems like they’re always playing.

And I just find it so fascinating because they see me doing it that they think they can do it as well it’s one of those things where I believe they’re going to be musicians because it’s there and nobody is pushing them to do it. They’re going above and beyond what I would expect them to do.

Even my oldest daughter, who has Down Syndrome and cannot get her fingers to do what she wants them to do, she persists and continues to play every single day and gets mad when she doesn’t get to play as much as she wants. It’s because she loves music. She knows that it matters and it’s important to me. And she wants it to be important to her as well. At least that’s what I think. But she’s doing it.

That idea of leading by example, teaching them how you want them to act, and then allowing them to stay focused. I think those three things, when you combine them together are really, really powerful.


It’s such a good example. I love it.

I feel like I didn’t answer the second half of your question about how I’m educating my son. I’ve had education on my mind lately because of the school situation we’re in right now.

It’s May 2020 and up until two months ago, he was at one of the best schools in all of England, but he didn’t like it. He liked it better than the school he was at before just a little bit. But all in all, he often said, “Do I have to go?” Every day, he felt drained and grumble, grumble, grumble.

And these last two months without school, I feel he’s actually thriving more than ever. He’s so into it, and I see him advancing and thriving, which makes me want to learn more about unschooling. We’re spending full time with him, so I’m just seeing these natural tendencies.

He loves memorization. He’s really good at it. So we use Anki, which is a flashcard software. We’ve been using that for a couple of years and he enjoys it. So wanting to raise a Little World Citizen, on the front of the flashcard, I put the picture of the country on the map. No words on the map, just the shaded region of a country. And he memorizes what country that is just by shape.

At this point, he knows over 130 countries in the world just by seeing the shape of the country on the front of the flashcard. He gets it really quickly. You just flash! And he goes, “Azerbaijan.” Flash! “Estonia.” Flash! “Peru.” Flash! “Vietnam.” Flash! “Indonesia.”

He recognizes these and he loves dancing while doing it. He says, “Give me some more. Give me some more, dad. I just want to keep dancing.”

But if you give him a word problem. Like “Jennifer went into the store and bought six loaves of bread for $0.30 each. How much did she spend?” He’s just completely stumped. So I don’t know at this point whether I should be maximizing his strengths or working on his weaknesses or both.

But here’s what I have noticed. When he sits down to do schoolwork, now that the school is back in session through these crappy online things, he does these required assignments, but he’s so distracted. When he’s sitting down to do a worksheet that school is requiring, everything will distract him. Every little bird out the window. Every paper clip on the table will be fascinating to him.

But when he’s making something himself or learning or reading through watching a video, he’s completely riveted and completely focused. And his memorization thing, he can recite word for word things he heard once a month ago if he was engaged while listening to it or watching it. But if he’s distracted like these school worksheets, he can’t tell you what he did five seconds ago.

I’m noticing this huge difference between him flourishing by doing whatever is naturally interesting to him versus just floundering through doing school assignments. I’m not really sure what to make of it. It’s all pretty new to me.


What I try to coach schools to do more of is to help kids be engaged in their learning by allowing them to choose the way that things work. So instead of saying, here are these things you have to do, we do it more the way you do parenting. What are you interested in? Focus on that and focus on that for as long as you can. What you see with kids is that naturally their focus is going to move from one thing to another.

However, you can get an intense amount of learning “done” in the time that they’re focused on that one thing. So, when you start with that premise and you start leading them down that path, then you create the opportunity for them to be engaged in something that they care about, that they’re interested in. And they’re going to learn so much more from that.

I’ve taken kids out of the regular classroom, put them into groups or by themselves or whatever, and have them find something that they’re interested in. And when we do that, what I inevitably see is that they care more about that than the work their teachers are assigning. They go deeper with that, and they often finish the work their teachers are assigning quickly so that they can turn their focus back to the thing that they’re really interested in.

That’s just one of the reasons why I’ve been wanting to interview you for so long. So we could talk about this, because as a parent, you’ve been doing that with your son and you’re seeing how school is, in my mind, basically killing creativity. You’re over there in in England, where Sir Ken Robinson was when he first started talking about how schools kill creativity.

In schools, the point is not to be creative and figure something out. The point is to get an assignment or a worksheet or whatever it is, complete that and receive feedback on it to know whether or not you did it right, according to the teacher, and then move on to the next thing that they can tell you that you did right or wrong. That’s just not a great way for kids to learn. It’s is demoralizing. It’s boring. It’s difficult. Nobody likes it. And yet that’s how we do education all over the world.

It’s not the best way to do it, but it’s the most efficient way if what we’re trying to do is to churn kids out through a factory model. But that’s probably not what you want for your son. That’s not what I want for my kids. You probably have different dreams for your son than being just like everybody else.


First, I think that any focus is good – or that any interest is good. The mastery path to anything is great whether it’s video games or juggling or beatboxing or skateboarding or surfing or poker or whatever. When they get so into something, they should be encouraged to master it, to help them see that they can become one of the best in the world if they focus and deliberately practice at that thing.

That may mean helping them get a good teacher who can observe and instruct. But I think mostly it’s helping them to take it seriously. I’m saying this because of my own thing as a teenager was heavy metal guitar. As a parent, it can be tempting to see that as a waste of time, like “Derek just won’t stop playing his guitar. Come on, you got to focus on something real.” But in wanting to be great at it, it helped me focus so much in every aspect of my life.

I didn’t realize this until recently when I looked back at teenage me. I was practicing six hours a day doing these deep finger exercises. Every day, I was looking for ways to improve as a guitarist. I read every interview with every successful musician looking for clues on how I could become one too. Which then led me to reading self-help books trying to master my life so I could be the successful person I wanted to be.

That eventually led to reading books on business to understand how I could make money with music because I really wanted to be a successful musician. All of this was outside of school, of course. High school was just teaching world history and English rhetoric and stuff I didn’t care about. I did terribly in school.

I went to Berklee College of Music, a music school, but even there, the classes were mostly teaching things like big band, jazz arranging, and things that weren’t directly applicable to what I was doing. But I just had this drive. I really was only focused on being a successful musician.

When I went back to my ten year high school reunion, I was 28 years old. I was shocked by how they all seemed so lost. I would ask them what they’re doing, and they were pushing papers around in some mid-level management job for Motorola or whatever, just paying the bills. They were 28, but they all looked 40. I was a full-time touring musician and they were blown away that I “followed my dreams”. My reaction was, “What did you think? I was kidding?”

I always knew exactly what I wanted. I was always laser-focused on it. I wanted to be a successful musician. It started at 14. And yes, I was only making $1000 a month while they were making more money in their corporate jobs. But it wasn’t about the money.

Looking back now, I didn’t really lift up my head and wonder what I wanted to do with my life until I was 39 when I sold CD Baby. It was the first time since I was 14 years old that I wasn’t sure exactly what I wanted to do. Everything from the age of 14 to 39, I was laser-focused on exactly what I was working on. Mastering guitar led to mastering music led to mastering business led to mastering programming led to mastering life skills.

When I say mastering, I mean trying to master these things, not saying I am a master of those things. But the point is I never sat around watching TV, getting drunk, going to parties, and all the time wasters that people do when they don’t know what else to do. I was always, always, always driven to be great. And so to finally answer your question, I think to be driven is the best thing that we can help someone learn, no matter what it is that they’re focused on.

I think that it doesn’t matter what someone’s focused on. It can be even as shallow as video games. It doesn’t matter if they’re on the path to mastery. Anything is better than that adrift, lost thing that makes people just sit around and do nothing but get drunk and hang out feeling lost.

So how to do that? How to help someone be driven? I don’t know. Maybe by demystifying it, by showing them the path, by showing them it’s possible, by helping them see the path, see the goal. I think it’s so crucial.


I don’t know guitarists so I couldn’t ask you anything specific, but I could probably ask you something about a specific guitarist and you could remember it even though you read the interview 20 years ago. Right?


[Laughter] Yeah. I know every little tidbit of trivia and everything I read since I was 14 about all those musicians. It’s crazy how much weird trivia I remember. Yeah, you’re right. I retained it all.


But you didn’t retain the things about world history that your teachers wanted you to learn. However, your son, because he’s interested in it, is paying attention to the shapes of countries and is probably going to know the shapes of countries for most of his life, if not his entire life. It’s really easy after you’ve gone down that path of mastery to see the things that you learned.

And for schools, we can do that really easily because we know what you’re supposed to learn and we can go attack those things on the back end and say, “Yup, this kid learned this.” So, for example, we had this program called Synergy at my school where kids could choose to do whatever they wanted to make the world a better place. And they got to define the world. They got to define better. They got to define what they were going to do. A really powerful experience. They had three hours over two days during the week to do that. I wish we could have given them more time to see what they could have created.

So we had some one group of kids that wanted to create a social network to prevent bullying at our school. And so they spent all their time working on that social network, trying to figure out how to create it, trying to learn how to code, to be able to code it, all that kind of stuff. Now, did they ever actually succeed? No, they didn’t. They didn’t have the time, the resources, or anything to succeed, but they learned so much.

They learned so much about research and about programming and about JavaScript and all these other languages that they had never known before. They learned about end user license agreements and terms and conditions and things like that that they would have never thought about before. They learned about how to write simple if and then statements to have somebody report bullying on that system so that they could eradicate it.

And all these things that they learned – I could find ways to tie them back to the content we were supposed to teach them. But those things, they’re going to remember forever. And they don’t need me to bless them and say that they’ve learned these things because they already know. My feedback and validation of that is really meaningless to them because that learning process is already completed.

But schools are not created that way. That’s why I try to help schools establish systems like that – because that allows kids to be creative. And as someone who’s created your whole life, you know that that is so important.

What would you say to someone who asks, “How do I get my kids to be more creative in my school?”


I love the example you just gave. When I look back at my schooling, there was no connection between school and my interests. It felt like school was the opposition. It was the hurdle. I was a bad student of all the required subjects. I failed a lot of assignments. I only got a passing grade because I did do well on the tests. I just refused to do the homework.

It was only when I saw music school as the key to getting what I want from life that I suddenly became a straight A student. I went above and beyond on every assignment because now it was applicable. That’s the word that I heard, by the way, in that story you just gave. Is that everything was now applicable?

And when I think back about my teenage obsession with being a successful musician, I was immediately applying what I was learning. What I was learning was helping me solve the problem I was wrestling with.

That’s the best way to learn. Even years later when I started programming, I did it out of absolute necessity. had already started CD Baby without doing any programming and it quickly ballooned and grew faster than I could handle. So I was doing many hours of manual labor, and I had to figure out how to automate it.

I feel bad for somebody that thinks, “Well, yeah, I guess I should probably learn how to program. I guess I’ll take a coding course.” But if you don’t have a problem to solve, it’s all going to be this foggy, abstract stuff.

I think we need a problem first, a mission, and then all of the learning based around that to help you solve that problem. So, yeah, school itself gave me nothing. Even when I went to music school. Even Berklee College of Music. At least when I was there, it just wasn’t very good. The teachers weren’t very good. They were often discouraging. They were often just these kind of burnt out musicians who would show up late to class, pretty disorganized.

But I was so driven that the school itself was a stepping stone for me. The school didn’t teach me anything and I almost dropped out because of it. It was only when I took a summer off and I thought, “You know what? If I know in advance the school isn’t going to teach me anything, then I can just go back and use it like a library. It can just be the resource where I can get the information I need, but I’ll just expect nothing of the school itself.”

So I went back for my second and remaining years expecting nothing of the school, and that’s when I got the most out of it – when I just used it as a resource.

All that said, all this talk of schooling, I know this is your world and this is your thing, but I’m 50 now and I graduated college when I was 20. School is like a distant teenage memory for me. I think in the big picture, I’ve learned so much more since then than I ever did in those few years I was at school. So in hindsight, it just feels like school itself was really not important at all.


Yeah, and that is exactly, exactly my point. It’s about learning for your whole life. It’s not just about those 13 years that you’re in regular K-12 education. School itself is just an institution. But if we think of it instead as learning and problem solving then it totally changes the dynamic.

And so if you went to school and instead of, your teacher saying, “Well, you know, it’s world history class, you need to learn these things.” They said, “What is it that you really want to spend your time doing? And how can we be a resource for that?” If your high school teachers would have said, “Use the school, the facility that we have to start recording your own music and to learn how to get better at it.” You would have had a totally different experience with school, right?


Probably, yeah.


And so that’s how it was when you finally took that approach the last couple of years ago at Berklee when you could you could use the school as a resource. And that’s where I believe we need to get it to as far as education goes because it’s not enough to go through a process of checking off standards.

We really need to teach people how to do what you just have been talking about this whole time, which is become a master in the things that you are interested in and to really focus on those things until you get good enough at them that that you feel like you have mastered them or that you’re done being interested in them.

There may come a time in a couple of weeks or years or months or whatever where your son says, “Yeah, I’m done with flashcards. I’m done with learning about countries. And I’m not interested in that anymore.” That may happen. It may not. But if it does, the next task is to find what the next thing is that he cares about and go all in on that.

All of the things he’s going to learn along the way, even when he’s switching to different things that he cares about, are completely worthwhile educational endeavors that should not be diminished or thought less of because they’re not what traditional school is.


Right. I tried to remember in all of this the nature and nurture contribution. I grew up thinking that everything was nurture. I didn’t believe in nature. I thought we all are entirely of our own making. It was interesting when years, years, years later, in my 40s, I read a few books on the subject of happiness, and it was fascinating to read that 50% of our happiness is genetic. Only 50% is through our actions and life circumstances. They found this over and over again in decades of studies.

One of my best friends is an Australian woman. She is one of the smartest people I know. She’s a scientist in Sydney, but she is one of those people who are like whip smart in every aspect of life. She learns languages like nothing. She’ll just visit Japan for a few weeks and come out speaking conversational Japanese with people. She’s just one of those super bright people.

Whenever she hears me obsessing a little too much about parenting, like trying to be the best parent I can or my kid’s school, she constantly reminds me by saying, “Derek, never forget, I grew up in the worst, crap part of Australia to the worst parents who kicked me out when I was 13. I grew up in foster homes. I went to the worst schools in the poorest parts of the outback. And now look at me.”

All this stuff you’re obsessing on doesn’t matter that much. It’s going to account for some things. Sure. But a lot of people just grow up being who they’re going to be no matter what you do. And it’s a nice counter reminder to all the stuff we try to optimize.


So even when going out of our way and trying so hard to do something a certain way, there are some things that we just can’t overcome. And it’s not the end of the world when that happens. I think for people who are listening, who really try hard to be the best they can be at something but sometimes fall short can be frustrating.

I think that story helps me understand that, it’s OK to be wherever you’re at. I don’t know if that was your intent, but that was what I thought.


It’s nice to remember, like, everything I’m doing, it’s going to account for something. But I can relax a little bit. It’s not a complete make it or break it situation.


I want to thank you again for your time, Derek. This has been awesome. The last question that I ask everybody is, what is one thing that a principal can do this week to be a transformative leader like you are?


Listen. I think that actually listening to kids instead of talking at them is the most important thing.


I think that is fantastic. Thank you so much for being part of this. The website, if you will learn more about Derek at You can see what he’s currently working on. You can check out his podcast. And anything else you’d like to promote, Derek?


No, I’m not here to promote anything. Just go to and send me an email and introduce yourself. The reason I like doing these interviews is for the people I meet.


That is exactly how we met four years ago. And we’ve emailed a couple of times back and forth since then. I just really appreciate your generosity and your time. So thanks again for being part of Transformative Principal.


Thanks, Jethro.