Derek Sivers

Interviews → Learning Leader / Ryan Hawk

Leadership, excellence, journaling for your future self, how I make better decisions

Date: 2020-05

Download: mp3



Welcome to the Learning Leader Show. I’m Ryan Hawk. Tonight’s featured leader is Derek Sivers. He started CD Baby and sold it in 2008 for $22 million dollars, donating all of it to a charitable cause. He’s a self-described monomaniac, introvert, slow thinker, and he loves finding a different point of view. He’s also the best-selling author of Anything You Want: 40 Lessons for a New Kind of Entrepreneur. Ladies and gentlemen, this one is a bit different, but very interesting.

Welcome, Derek Sivers, it’s great to have you. I’ve been following your work for many years and I’m a big fan, so it’s great to talk with you, man.


Thanks, Ryan. I like your show, and that’s why I’m here. Thanks for having me.


I remember listening to someone else’s podcast thinking, “Who is this guy with the soothing voice?”

I had to pause and take so many notes on my phone. I thought, “This is maybe one of my favorite podcast episodes I’ve ever listened to. I have to talk to this guy at some point!” That was about five years ago. So, it’s great to finally be here.

We’re both dads, so I want to start this one a little bit differently.

You became a dad eight years ago. How did becoming a dad change your views on the world? On leadership?


That change that I hear other dads talk about – I had most of that happen when I started CD Baby at 29.

Until then, everything I did was just for me. I had been around the world, performed 1000 shows, recorded multiple albums, been on the radio, and bought a house with the money I made making music.

So, when I accidently started CD Baby, I started caring about my musician clients more than I cared about myself. I wanted them to have the spotlight, not me. I wanted them to get rich, not me.

Then I had employees. People whose lives were dependent on me. It was up to me to take care of them, pay them well, make sure they were happy and healthy and growing.

When friends have told me how having a kid changed their life, I think I went through some of that already with starting my company. That’s when life become less about me

So, when I had a real baby 10 years later? The major change-of-view was to be fully present with him. I’m usually very future-focused. My head is always in my work and my future plans.

But to be with my kid, I have to shut that all down, physically and mentally, and just be 100% engaged in his world, his play.

The common leadership lesson between those two things is to be selfless. The leader follows the led.


I read that you’ll go to the park or play in the wilderness with your son for hours and hours. How have you built up the energy? What’s your mindset towards promoting and nurturing that exploration in your child?


For one, it really helped that I raised him in New Zealand. We just moved to England a year ago, but the first seven years of his life were in gorgeous, breathtaking New Zealand.

If we’re out in nature, somewhere stunning, and my kid is sitting there playing with a stick, I’m happy to hang out there and look at the world for five hours.

When we’re trapped inside on a rainy day, it’s hard to sit on the living room carpet for five hours. I don’t have master Zen patience, but it really helped that I would usually take us somewhere gorgeous to go play.

I noticed that adults are always looking for big, amazing superlatives. I would say, “Let me take you to some distant, amazing thing I’m going to show you!” But kids are happy with the tiny details.

Many times, we’d drive many hours to get to the most amazing view or forest or rock formation in New Zealand. Then we’d arrive, and he’d prefer to play with the dead log full of bugs that was right at the trail entrance. We’d often never even get to the big amazing thing I intended to see because we’d just play all day long with the detailed thing.

So, we stopped wasting hours driving to amazing things, and instead had a blast in the local forest 5 minutes from home.

You don’t need amazing things to play. Some sticks, some leaves, a cardboard box, some trash. He has more fun with these things than official toys.

Put another way, if you buy your kid a toy, they’ll probably have more fun with the box it came in.


How do you make big decisions? Like where to live, how to parent, relationships, etc.


We should talk about values because that’s a huge part of it.

I’ll give you a concrete example. I grew up in Hinsdale, Illinois. I was even more entrenched in America when I was living on the beach in Santa Monica, California. I very explicitly felt that it was the only place for me. I never wanted to go anywhere else. I didn’t even want to take a vacation because I felt like I lived in paradise.

I had little disagreements with my girlfriend at the time who wanted to travel. I’d say, “Travel? We live in paradise. This is amazing. I never want to go anywhere but Santa Monica ever again!”

But later I thought, “Oh, wait a minute. I’m 35. Am I seriously going to spend the rest of my life here in this one spot? Is that me?”

And just like that, the value system in my head flipped, and suddenly, I thought, “No, no, no, wait a minute. I love Santa Monica. But learning, growing, exploring, and expanding my self-identity are really important to me. Oh, my God, what have I done?”

Many of these changes happen in an instant. You have a certain thought that you can’t un-think, and the wiring in your brain changes instantly.

But in general, with navigating big decisions, the biggest lesson I’ve learned in the past couple of years is the difference between in-theory and in-practice.

In theory, you can read books on parenting, think about where you’d like to live, describe what kind of relationship you’d like.

In practice, when you actually go try the thing you think you wanted, you often find that you don’t actually like it. You thought it’d be really different than it is, or the other people involved in this decision with you have a very different set of needs and values than you do.

So, don’t consider anything decided until you’ve had a chance to try it in the real world.

Don’t announce, “We’ve decided we’re going to move to the countryside!” Because you’re going to be embarrassed and guilty and conflicted if you get there and find out you don’t like living in the countryside. In theory, you thought you did. But in practice, you didn’t know they were going be this many bugs. It’s boring.

Instead, say, “We’re going to try living in the countryside for a while and see what it’s like.”

Announcing your plans has a weird effect on your psyche and self-identity. You have to be careful when you announce things because it can mess with you wanting to go through with them or not.


I saw you gave a TED Talk about how there’s a lot of research on why you should keep your goals to yourself, and why you shouldn’t share them with other people. This is counterintuitive to what most people say. Can you explain?


I’m no expert in this. I read an article in Newsweek magazine once that talked about this, and I thought it was interesting. It happened to be on the same day that the TED conference was asking for submissions. I said, “I could talk about this thing I heard about earlier today,” and they chose me.

So, I had to get on stage as if I was some kind of expert. The idea is for a certain kind of goal, called an identity goal. Pursuing this goal lifts your self-esteem and your esteem in the eyes of others. It makes you a different person in your eyes.

For example, you might say, “I’m going to do the Iron Man competition,” or, “I’m going to learn Mandarin,” and others may give you the social satisfaction like, “Oh, Ryan, dude. Right on! You’re going to do Iron Man! Wow! You’re going to learn Chinese?! I could never do that.”

That social feedback gives you internal satisfaction. You think, “That’s right. I’m the kind of guy that does Iron Man. I’m the kind of guy that learns Chinese.” You’ve now already felt a lot of the satisfaction that you shouldn’t have felt until you actually do the thing.

We’re social creatures. The things other people say and what other people think of us affects us a lot. So, for identity goals, try not telling anybody. Keep it to yourself so that you have to actually do the hard work necessary in order to get any satisfaction from this thing. Otherwise, you might not follow through and do the hard work necessary since you’ve already felt the reward from announcing it.


I often open this podcast with a question about sustaining excellence.

What have you found to be the commonalities among people who have sustained excellence?


They hold themselves in very high value. In other words, the stakes are high.

This is a little personal, but why not? I’m going to tell a little story because I was in love with an Olympic athlete and got to know her very, very well. Her self-worth was so inspiring. I was one of only four people that had her phone number because she raised the bar for social interaction so high that only these four people were allowed to take her time. Everyone else had to go through her agent. Her agent was one of the four people that had her number.

And even for dear friends, she loved them fully, but they weren’t allowed to waste her time. She was shocked that I let my friends complain about their life for hours. She said her friends know not to waste her time like that. Their time together had to be high-quality.

She never ever broke her diet. Yolks removed from eggs. No oil on the salad. Never a piece of bread. I said, “You don’t like bread?”

She said, “I love bread, but if I eat the bread then my performance suffers tomorrow, and nothing is worth that.”

She had the most amazing self-control because she valued herself so highly.


Was she happy?




Really? It doesn’t sound like that happy of a life to me.


This was a life-long mission. She had been like this since she was four years old.


Part of being a good friend is to be there when they need you. Sometimes you’re going to receive, and other times you’re going to be more of a giver in the relationship.


I think she put the bar in a different place. The random little whining and moaning about your day for hours? No.

But if you need to talk? She’d be there for you.

She always put her practice and training as the top priority above everything else. And for the most part, that was true. There were a couple times in our times together when I called her and said, “I really need to talk,” and she said, “OK, no problem. I’ll wrap up now. I’ll call you back in five minutes.”


So, you found that these people to seem to have extremely high expectations for themselves first, and their lives align with those big expectations?


Yeah. I’m running through examples of my high performing friends in my head and the most common thing is that they all have very high self-esteem.


How do you define excellence?


Setting very high standards and then living up to those standards. I think it’s totally subjective for each person.


How do you do that for yourself? What is living an excellent life mean to you? And this may be a weird question, but is that something that’s important to you?


Yes, it’s important to me, but how it’s defined might change daily. Like the example I said earlier about living in Santa Monica. On Tuesday, I thought, “This is where I’m going to spend my whole life. I live in the best place on Earth” and by Thursday, I thought, “I need to leave America and never come back in the name of growth and exploration.”

Your values can flip where suddenly, what you would have described as an excellent life two days ago is not what you would describe as an excellent life. The definition is ever changing.

But, yes, I definitely hold myself to high standards. I think that’s why I fell for the athlete. I hadn’t met anybody like her before. I hold myself to a very high expectation for what I want out of life.


Let’s shift to a leadership perspective.

When you were running CD Baby, you mentioned you had 80 plus employees. What is your definition of excellent leadership?


I haven’t thought about this in a long time. It’s been 12 years since I left CD Baby. I was a leader there for 10 years, and a big reason I quit was because I didn’t like the having all that responsibility.

Excellent leadership is being selfless.

Having the perspective to see what’s long-term best for the people you’re serving then ensuring it happens.

A narcissist is the opposite of a leader. Good leadership is forgetting yourself and doing what’s best for others.


You sold CD Baby. Can you share the exit story there? How much you sold it for and what you did with the money and why?


[Laughter] In four seconds, you asked about the three things I planned to never speak about – not during this phone call – but 12 years ago when I sold the company. Back then, I thought, “OK, how much I sold it for and what I’m doing with the money. . .this is nobody’s business.”

It was 2008, and podcasts weren’t really mainstream yet. This guy, Greg Galland, interviewed me on his podcast. We were an hour into the conversation when he asked, “So how much did you sell for?”

I was suddenly put on the spot and thought, “Should I say this out loud? It’s nobody’s business, but we’re on air. I’m being recorded. I don’t want to be rude. We’re an hour into this podcast. Nobody listens to these things anyway.”

Then, I said, “I sold it for $22 million,” and he published the podcast with “Derek Sivers Sells CD Baby for 22 million,” as the big headline.

I thought, “God damn it. I outed myself accidentally!”

About a month later, I still didn’t learn my lesson. I still didn’t think anybody listens an hour into a podcast. Some random dude said, “How does it feel to be swimming in $22 million dollars now?”

I said, “Actually, I gave it all away.”

He asked why, and I said, “It’s set up as a charitable trust. I put all the money into the trust because I didn’t want it.”

He said, “Wait, we need to talk about this.”

I thought, “Oh man. I didn’t think I was ever going to talk about this publicly.”

That’s the answer through my winding little tale. I was already making plenty of money before I sold the company. I was the sole owner. I had no investors. It was a very profitable business. When I sold the company for $22 million, I knew that I didn’t even want the money.

So, I set up a charitable trust to benefit music education because that felt like the grand circle of life. All this money came from musicians in this generation, and when I die, it’s going to go to the next generation of musicians.


Do you ever rethink that decision? Are there ever days where I could be nice to have like $10 million?


No. Never.

I journal for one to three hours a day. It’s like I watch movies in my head. I play out alternate futures. When I occasionally start to have that thought that you just described, I ask myself, “What would I do if I had a hundred billion dollars right now?”

I’ll sit there with an open journal and write, “Uh, what if I got a Tesla? I don’t need a Tesla. Maybe I’d hire a teacher to help? Yes, I could. OK. That would cost $20,000. Uh. . .”

I get stumped because I wouldn’t do anything differently. I don’t want anything. So, I never regret the decision. I’m really glad that I don’t have $22 million dollars burning a hole through my pocket.


You just mentioned that you journal a lot. Many leaders stress the importance of documenting what you think by putting pen to paper.

What have you found to be the power behind documenting your thoughts?


I haven’t watched a video or TV of any kind for more than two hours in the past year. I don’t watch anything. So, my journaling time comes from that kind of time. I really mean it when I say that I watch movies in my brain. Any time I feel like crashing on the couch and exhaling, I do it with a journal in my hands. I write. I play out hypotheticals. I pour out whatever is in my head.

To answer your question about the importance of journaling, just a few years ago I started keeping topic journals. I found that there were some subjects that I kept coming back to. I write on the computer in text files, but I’m sure you could do this on paper, too.

Four years ago, we were considering moving back to Singapore from New Zealand. For years, I kept having thoughts come into my head about Singapore. Eventually I thought, “I should really keep all of these in one place instead of having them scattered among 400 separate entries.”

That’s when I started keeping a ThoughtsOn journal. I have a folder called ThoughtsOn. Inside are a couple hundred text files with names like Singapore, or language learning, or interviews. It really helps whenever you find yourself returning to the same subject to open up that journal and write down your current thoughts with a timestamp.

It’s fascinating to scroll through and see how your thoughts have changed on a subject three months ago, one year ago, or three years ago.

For example, last year I really wanted a dog but knew that it’s a huge commitment. I said, “I’m not going to get a dog unless a year has passed, and I still want a dog.” I had ThoughtsOnDog.txt. It was interesting to see that after a year, my thoughts were very consistent. So, I got a dog. When I was living in New Zealand, I thought it would be really cool to get an RV. I thought about it for a few months. I had ThoughtsOnRV.txt full of many, many, many thoughts about why I want an RV with the pros and cons.

Eventually, I got an RV and it was totally different than I expected. It was terrible. I hated it. That lasted a few weeks. I sold it right back to the dealer I bought it from. Luckily, I didn’t lose too much money.

ThoughtsOn journals are fascinating to see what I expected it to be like versus what it was actually like.

Writing things down is one of the most useful things anyone can do. Don’t write just the first thought that comes to mind. Constantly challenge yourself.

When you ask yourself a question like why do I think we should move to the countryside? You’re first answer might be something like because I want silence.

But you have to push back on yourself. You could write, “Am I unable to get silence where I’m living now? Would noise proof windows solve that same problem? Then, I could still remain conveniently located where we are. Do I need to move an hour into the countryside to get silence or could I move five minutes away?”

Push back on yourself to challenge your thinking.

Lastly, I think it’s also important to keep a daily dairy. Even if you spend five minutes a day writing down what you did, I’ll bet that Future You is going to want to know what present you, back in the crazy year of 2020, was doing. In 2050, you’re probably going to wonder, “Was I really as scared or as happy as I remember in 2020? What was I thinking when all that crazy stuff was going down? I have some faint memories.”

It’s way more interesting to look at a daily diary of what you were doing. Journal your current activities as a service to your future self.


You mentioned earlier in the conversation about your values.

What are some of your core values? How do you live according to those values?


Values themselves aren’t very interesting. My values are learning, creating, growing, changing, and parenting. That’s boring.

How do I live them? I notice when one is lacking and give it more priority until it’s not lacking anymore. That’s boring, too.

What’s interesting is remaining flexible and creative in HOW you can fulfill them. The big idea is to not get stuck on one plan.

Say you planned to be a public speaker or concert promoter. You decided this is what matters most to you. Then, Covid-19 hits and the career of a public speaker or concert promoter is not going to be do-able for a few years. You have to ask yourself, “What did I really want from doing this?”

Was it to share your ideas? To become eloquent? To meet lots of people? What are some other creative ways you can get what you want, considering the new situation?

Say travel was your top priority. But then you have a baby with someone who is strongly opposed to travel. Again, you have to ask yourself what you really wanted from doing that. Was it to eat new food? Understand different cultures? To brag on Instagram about your wonderful life? You have to be really honest with yourself about what you really wanted.

Then think through some other creative ways you can meet those needs, considering your new situation.

Lastly, don’t get too attached to your current values. They may change at any time. If health was never a top priority, but then you get cancer, suddenly health becomes a top priority and partying or travel might suddenly become unappealing.

So, when somebody wants to know your values, you can say, “These are my values NOW.”


You’re a self-described monomaniac.


[Laughter] I only learned that term a month ago.


This means that you’re the type of person who is obsessed with one thing.

How did you diagnose yourself as that, and how do you think that’s been helpful for you?


This sounds like a very serious thing, especially when you say diagnosis [laughter].

I randomly came across this word in a book, and I thought, “Monomaniac. What is that?” I looked it up and I went, “Hey, that’s me!”

I have always been this way since I was a kid. I get really, really into one thing at a time. I’m really not good at living a super balanced life where I wake up and do an hour of this and three hours of that. I admire people who can do that. I’ve tried, but I get so into what I’m doing that I want to see it through to completion.


What are some of those things recently for you?


A very concrete example is my next book called How to Live. I absolutely love writing it so much. Around Christmas time, I’d write for 15 hours a day, seven days a week, only stopping to play with my kid.

Then, my assistant said, “Hey, there are a whole bunch of things on the back end of this system here that I really can’t do my work without. I need your help making these things.”

So, I paused the writing of my book and for three months, I dove completely into programming backend tools I needed in order to help me handle the book production stuff better. I did nothing but programming for three months. I haven’t done any writing in months, and I’m at the very tail end of that now.

As soon as I’m done with the programming, I’m diving back into writing – nothing but writing all day, every day.

Another example is when Covid-19 started, I got really worried about all these people I know out in the world. I sent out an email to my whole mailing list saying, “How are you? Are you OK? Yes, I’m really asking. Please answer.”

I got 7,000 emails in return. For the following two weeks, I did nothing but answer emails. I would get up at 5:30 A.M. and I would answer emails, stopping to stretch and eat a little bit, then get back to it until midnight every day. I did this for almost 18 hours every day for two weeks until they were done because I just like to see things through to completion.


You wrote about that and said, “I was immersed in people’s stories and almost devastated from the stress, but also thankful for the connection.”

With those emails, is there a point where that stress outweighs the value of the connection? What’s your decision-making process for that?


I think in terms of net – the warm, fuzzy, good feelings I get from connecting with 7000 people versus a few hours of stress trying to get back to them all in time. So that’s a huge plus and a little minus. That’s net positive.

Let’s pick a different example. Say someone buys a house that’s bigger than they need, or a new fancy car that costs 10 times what a basic, cheap, used car would cost. If somebody decides to buy those things, then they’re probably deciding that they’re going to have to work at a job doing something they don’t really want to do for the next 10 years in order to pay off that expense. It’s nice to have a fancier car, but there’s a huge minus on the backside of that. That’s net negative.

I’ve always been a long-term thinker. Even as a teenager when my friends would ask why I didn’t have any tattoos, I’d say, “Because my 90-year-old self might not want them.”

They’d look at me weirdly and say, “Dude. . .What?”

I’m always thinking in terms of decades and the long-term net positive or net negative.


What’s the primary source of your revenue streams now? Is it writing books?


I haven’t made any money since 2008 when I sold CD Baby. I had plenty of money saved up, so I’ve just been living off of savings.


Seriously? Oh wow.


Yup. I do everything for free. I enjoy that. I like not having to monetize the things I enjoy doing. The thousands of hours of answering emails, I’m doing it because I enjoy the connection.


What about Anything You Want, which is a very popular book?


Sorry, I have earned a little money from that. Hardly anything in the big picture. If that money went if that money went into my bank account, I didn’t even notice.


So, you’re good for the foreseeable future financially?


I live very cheaply, so I’m good.


Wow. It reminds me of Forrest Gump, “That’s like one less thing.”


[Laughter] Yes! I love that quote!


He would mow the grass for free because that’s one less thing to worry about [laughter].

As a family, we have high fixed costs because kids are expensive. But I did walk away from a corporate America job with some of those inflated salaries and comp plans to do something that I loved more. And the satisfaction in it is dramatically increased, even if initially the income went away.

I’m fascinated that it seems like money is not something you even think about?


Yeah, it’s amazing.


I don’t think that part is relatable to many people listening, Derek. You probably know that.


Ever since I was a teenager, I found a way to live so cheaply that I never really had to do anything I didn’t want to do. Instead, I would lower my expenses so that making a few hundred dollars a month would pay my cost of living. There’s always something you can enjoy while living off a few hundred dollars a month. That’s always been my approach to life.

Running and selling the company and making millions doing it just made that even easier to do.


That’s really interesting. Derek. Once again, thank you so much for investing your time with me and my listeners today. Where can they learn more about you?


Only one place. Go to

As you can tell, I like hearing from people. This is honestly why I do interviews like this. For one, I liked Ryan’s interesting questions and they were very thought provoking. But otherwise, I really like hearing from people.

So, go to and my email address is there. Introduce yourself and say, “Hello.”


By the way, it is the fastest website on the Internet


[Laughter] Because I’m a minimalist. I hand coded the site and I didn’t add a single line unless it absolutely had to be there.


If you click on a link, you will be on that page instantly. I’ve never experienced anything like it. I thought, “Could I hire Derek to do my website?” I love it.


I wish everybody would do this. Remove all the bloat. Think of the average site, and why you’re there. Usually, there are some paragraphs of text that you want to read, but there’s also a lot of junk. We should get rid of all the other junk and give the few paragraphs of text that people came for.


I love it. Thanks again, man.


Thanks, Ryan.


Wow. Very grateful for Derek’s time today. A few of the key parts that I thought of:

Don’t be the type of person who talks about what they’re going to do. Be the type of person who actually does it. This was spoken about when we were on the topic of why you should keep your goals to yourself. Be a person of action, a person of accomplishment, not someone who walks around talking and telling everybody about what you’re about to do.

The importance of the daily journal. It’s very valuable to document your thoughts and beliefs and your future self will thank your current self.

Leadership is thinking about what is, in the long term, best interest of the people.