Derek Sivers

Interviews → Tim Ferriss Show : part 2

31 minutes about the definition of success, unpopular beliefs, and more

Date: 2015-12

Download: mp3



When someone asks you “what do you do?”, how do you answer it?


That is a heavy question for everyone, isn’t it? We think, “Oh no. This is my big moment. This is where I define who I am!”

I heard that Steward Brand gives a different answer every time he’s asked. I like that. It’s a good challenge.

Search YouTube for the British magician Derren Brown doing his hypnotizing hand shake. The video is called Russian Scam. He holds out his hand as if to shake yours, but then grabs your forearm with the opposite hand instead, and puts something else in your hand. It puts people into a state of confusion, where they’re open to suggestion to help find some reason for what’s going on here.

He’s got a great little book called “Tricks of the Mind” that I highly recommend, where he tells how he did something similar to stop a mugging. He was held up at knifepoint in a dark street once. The attacker said, “Give me all your money!” and Darren just said to the attacker, “My grandfather had a wall that was 5 feet high! Little ducks all around. Do you know the type? Like this?” A few more nonsense sentences and the mugger was completely thrown off, and just walked off, derailed. Confusion is a great way to break habits.

So latelly when someone asks what I do, I say something like, “I don’t know,” or, “Y’know, I’d never thought about it before.”

It derails the routine of a boring conversation. Lets them know we’re not just painting by numbers now.

Also, it’s like finding someone who doesn’t know their name. How could you not know your name? How could you not know what you do? Poor thing must have amnesia. Let’s help him figure it out. Because we can’t just have someone walking around not knowing what it is they do now, can we?


When you think of the word “successful,” who’s the first person who comes to mind and why?


The first answer to any question isn’t much fun, because it’s just automatic. “What the first painting that comes to mind: Mona Lisa. Genius: Einstein. Composer: Mozart.”

This is the subject of the book “Thinking Fast and Slow” by Daniel Kahneman.

There’s the instant, unconscious, automatic thinking. Then there’s the slower, conscious, rational, deliberate thinking.

I’m really into the slower thinking. Breaking my automatic responses to the things in my life, and slowly thinking through a more deliberate response instead.

Then, for the things in life where an automatic response is useful, creating a new one consciously.

So what if you asked, “When you think of the word successful, who’s the third person who comes to mind, and why are they actually more successful than the first person that came to mind?”

In that case: first would be Richard Branson, because that’s like the stereotype - the Mona Lisa. And honestly, you might be my 2nd answer, but we can talk about that later.

My third and real answer is we can’t know, without knowing their aims.

What if Richard Branson set out to live a quiet life, but like a compulsive gambler, just can’t stop creating companies? Then that changes everything, and we can’t call him successful anymore.


What are the most common misconceptions about you?


Oh, I feel pretty understood. I don’t think people are thinking about me enough to conjure up any misconceptions.

We think the goal of writing and communication is to be understood, but I think a better goal is making sure you’re not misunderstood.

I learned this the hard way at my last company because we had a quarter million customers, so when I’d sent out an email to everyone, if any sentence was at all unclear in any way, I’d get 50,000 confused replies, which would take my team like a thousand man hours to go through.

Anything I put out into the public is rewritten and edited like crazy until I think it’s as clear as can be.


What are your morning rituals? What does the first 60 min of your day look like?


Not only do I not have morning rituals, there’s really nothing that I do every day, except maybe some form of writing. Here’s why:

I get really really into one thing at a time. For example:

A year ago, I discovered a new approach to programming the PostgreSQL database, that made all my code a lot easier, so I spent five months, like every waking hour, just completely immersed in this one thing. Bounce out of bed at 5am, programming SQL code like 19 hours a day, from 5am til midnight, just stopping maybe an hour or two a day to go for run or talk on the phone with a friend.

Then after five months, I finished that project. So I took a week and went hiking in Milford Sound, New Zealand. Totally offline. When I got back from that I was so zen nature-boy that I spent the next week or two just reading books outside.

Then it was time to prepare my big keynote speech for this conference, which tied into something I’d been wanting to do for years anyway, which is turning all my book notes into succinct directives. So for the next three or four months I did nothing but that. Again, like 5am til midnight. You can’t pry me away from my work when I’m really in the zone like that. I don’t want to hang out, watch anything, or distract myself in any way. I’m just so into what I’m doing.

Actually... when I started CD Baby, it began a singular obsession that lasted 10 years! For those 10 years, like 7 days a week from 7am til midnight, I did almost nothing else but work on the business. So sometimes that project can last 10 years.

I can picture that ideal world where I spend a few hours a day on each of my top three priorities. But I just get so in the zone with one thing that it feels like going against nature to break that!

I read once that people who were happiest with their life, when interviewed at the end of their life, were the ones who had spent the most time in that state of flow - being in the zone.

So although I feel I probably should have morning rituals and daily habits, I just don’t.

Knowing this, I can plan accordingly. Like if I’m going to learn a language, it’s probably not going to be by doing it 2 hours a day, but rather just total immersion.


What are you world-class at that people might not realize? or: What do your best friends know you’re world-class at, that the rest of the world doesn’t know?


I’ve got the world’s longest attention span. I’ll just sit down and do one task for 12 hours straight, or all day for 30 days in a row.

I love that my kid is getting it from me, by the way we play. I never say “let’s go, time to go”. We just do something until he’s ready to move on. He’ll lead me to the river and just throw rocks in the water for a couple hours. Then we’ll go the ocean and build a fort out of driftwood for hours, then draw in the sand with the shells until he’s sleepy. We’ve always done it this way, since he was 1 year old. Other families would come play on the playground for 20-30 minutes at a time, but we’d just stay there for hours, with him fully immersed in some newly invented game.

Nobody else can hang with us like this. Not even his mom. Everyone else gets so bored.

People ask if I meditate or do yoga, but no. My daily life feels like working meditation. Even being with my kid is like meditation, as you can tell.

Sam Thomas Davies:

Where are you up to with the “Do This” project? Are you going to be sharing your findings on your blog?


Yes. Definitely. In the first podcast I said I had like 18 sentences, but really I meant I have like 18 categories, like “How to be Useful to Others”, “How to Get Rich”, “How to Like People”.

Alltogether, I’ve got about 120 directives right now, each requiring a little more explanation.

Instead of just listing them all, I think each idea deserves its own little spotlight. A page that can be linked to and shared, about just that one idea, instead of only the entire list.

If you want to be notified when they’re ready, get on my private email list, either by going to or just email me to ask.

I think they’re going to be my next 120 blog posts. Then afterwards, I’ll post the big list, with each point linking to those past posts for more information.

Tobin Kaestner:

What are some directives for sharing thoughts online in an authentic way, particularly for introverts?


That’s not an introvert/extrovert thing. Everyone is scared to show their work publicly. At least doing it online is easier than getting up on stage.

The best book on this subject is Show Your Work by Austin Kleon. Go to to see my notes on it. As for some directives, I’ve got 4:

  1. Teach whatever you’ve learned immediately after learning it, while you still remember what it’s like to not know it. Once you get used to knowing it, you can’t imagine what it’s like to not know.
  2. Share your work online. If your work isn’t online, it basically doesn’t exist.
  3. Share the process and residue of your work. People really do want to see how the sausage gets made. Become a documentarian of what you do.
  4. But release your creations some time after completion, once you’ve already moved on to the next thing. So the world’s feedback won’t feel like it’s reflecting on you, but just on some work you did in your past.
Aymane Abaich:

Why and how did you become a programmer?


For me, it was absolute necessity. That’s the best way to learn anything.

There’s a story about Socrates. A student came to him and asked, “Socrates, how do I get wisdom?” Socrates walked him into a nearby lake. When the water was waist high, Socrates suddenly grabbed the student’s head and held it under water. At first he thought it was a joke, but Socrates kept holding him. He paniced and started struggling to get up and his lungs started burning. Finally Socrates let him up, coughing and gasping for air. Socrates then said, “When you desire wisdom as much as that next breath, nothing will stop you from getting it.”

So if you want to start programming, first you have to have a problem that you need to solve. You have to feel the pain of the problem first, then go find its solution. Just start trying to build something you need, so you can find out what you don’t know.

But also learn from a well-written book that guides you through things you didn’t even know existed. Search Amazon for a programming book released in the last few years that multiple reviews say were perfect to help a beginner understand.

As for me? It wasn’t until after CD Baby took off that I started learning programming out of absolute necessity. I was doing hours a day of manual labor, copy and pasting, processing everything by hand. So by learning to write some simple tiny 20-line programs, I saved myself hundreds of hours of work. Then as my company grew, each new thing I learned to automate would save my whole team hours a day of work. So yeah, the ultimate motivation.

Now I love it for its own sake. I think it’s fascinating. And the lifestyle suits me. I love to sit in solitude, and think and make things. I love the immediate feedback. I highly recommend it to anyone interested.

Tobin Kaestner:

What are some directives for creating relationships with people who hold interesting worldviews?


You make people interesting. If you’re boring, they’re boring. If you’re interested, they’re interesting.

I’ve read a lot of books on people skills, and they’ve all been so worth the time.

  • How to Win Friends & Influence People by Dale Carnegie
  • How to Talk to Anyone by Leil Lowndes
  • How to Make People Like You in 90 Seconds or Less by Nicholas Boothman
  • Power Schmoozing by Terri Mandell

They have the most awful titles, but really every book I’ve found on the subject has been great. So go read five books on the subject to get you into a considerate mindset.

Then practice with anyone. Start with low stakes. You’re actually probably a better conversationalist if you don’t think someone is a VIP up on a pedestal.

Back when I was a musician trying to get famous, I went to a music business conference, trying to meet VIPs from record labels that could sign me to a record deal. Such high stakes and I was so nervous. Then during a break I went to go dip my feet in the pool and just exhale a bit. I was sitting next to some dude doing the same thing, and we started talking about that girl over there, and the silly platters of food they had laid out, and why people come to these events in the first place, stuff like that. Cool dude. After a while he had to go, so he handed me his card, and it turned out he was the vice president of A&M records. Holy shit! If I would have known, I’m sure I would have been an uptight mosquito. So... yeah. I learned a lot about being a good friend and conversationalist from that moment. He and I are still friends to this day, and he sent me some of my biggest clients when I started CD Baby.

Lastly, it helps when you have something to show for yourself. Some cred. People want to meet another winner. So don’t hide your accolades.

David DiGiovanni:

You’ve helped a lot of people make money. Does success in business have to be more complicated than that? I get overwhelmed at times with the directives I find in the “how to make money” or “how to grow your business” content. Isn’t success just as simple as being creative and coming up with ideas on how to help others succeed?


Let’s talk about two things: simple vs complicated, and easy vs hard.

Look at running.

If you talk with people who hate running, you’ll hear them say, “Ugh. First you have to get your running clothes, and get dressed. Then you have to put on your shoes, then lace them up just right. Then you have to stretch, and warm up. Then afterwards you need to cool down, then shower. It’s such a pain!”

But if you talk with people who love running, they’ll say, “You just pop out for a quick run.” If you ask them about the steps involved, they’ll say there’s only one: just run.

So knowing that we have this human nature to think of things we like as simple, and things we don’t as complicated, you can use this to deliberately simplify how you think of something you’re avoiding, making it more appealing.

An ultra-marathon is simple: you just run 100 miles to the end. But that doesn’t mean it’s easy!

Success in business can be simple: find a need that people are proving they are willing to pay for, then find a profitable way to solve that need for them. But that doesn’t mean it’s easy!

Notice (in your mind) when your complications are holding you back. Turn the dial towards simplicity, so you just jump out the door and start running.

Notice (in your results) when your simplified approach is holding you back. Perhaps you’re using only one tool in the toolbox, and need to learn others.

And as for all the business advice out there, well, if information was the answer then we’d all be billionaires with perfect abs. So really you, yeah you listening to this, you need to shut that shit off, put your blinders on, get out the door and start running. (Metaphorically speaking, that is.)


On the homepage of, and during the podcast, you mention that you are an INTJ. How has knowing your type affected your life? Has it played a role in any major life decision?


To me it doesn’t really matter much. It’s just shorthand for a basic description of my preferences. I could write a few paragraphs about how I love solitude and making systems, or I could just link to the INTJ description.

The Myers Brigs are kinda like we made 16 little clubs, like Hufflepuff, Griffendor, Ravenclaw, so you can say, “Oh hey you’re a Ravenclaw! Me too!” I’ve met a few other INTJs who contact me because I have it right there in my self-definition, and we always seem to get along really well.

As for affecting my life, when I stopped going against my introvert nature and decided to shape my life around it, it made me very happy. Before that I used to do a lot of really extroverted things, thinking I had to.

But now I work alone instead of around others. I say no to almost all group-things, and instead spend one-on-one time with others. And I’m happier than ever. It's one of the best changes I ever made in my life.

Tobin Kaestner:

What should someone ask to determine their own utopia?


Ask yourself, “Is this in theory or in practice?” Have you proven from experience that this is what works best for you?

Whatever idea you have, challenge it. Argue against it, because so many things seem great in theory.

For example: Say you’re living in a little apartment in a noisy city. You think you’d be happy if only you had a big place out in the silent country. So you do it, you splurge, you buy a place, or sign a year long lease. Then you move in, and.... ooops. After two months, you realize you miss too many things about the city. Wrong prediction. Same with people moving from the quiet burbs to the big city. Or from being an employee to starting your own business. Ooops.

So do little tests. Try a few months of living the life you think you want, but leave yourself an exit plan, being open to the big chance that you might not like it after actually trying it.

The best book about this is “Stumbling on Happiness” by Daniel Gilbert. His recommendation is to talk to a few people who are currently where you think you want to be. Ask them for the pros and cons. Trust their opinion since they’re right in it, not just remembering or imagining.

James McGeough:

How do you define success? What habits or skills are most important to living a successful life?


First, let’s define success.

Were Robin Williams and Philip Seymour Hoffman successful actors? It’s a tough call. First reaction is yes, but... the more I think about it, my answer moves halfway towards no.

Think of someone you know who you’d consider to be the definition of a total loser. Now give that person a million dollars. Are they now a winner? Of course not.

That sounds like a contrived example, but a lot of fame and fortune is dropped in the lap of people who were just the right face in the right place at the right time, but are actually miserable awful people by any definition.

So the more you think it through, the more you realize that you have to define success first by your inner game, not some outside measure of money or fame. Mastering yourself, your mind, and your actions.

But if you only master yourself, and don’t help anyone else, we’d call you happy, but almost nobody would define that as successful.

So the definition of success must include how much you helped others. If you helped thousands of people, even if you ultimately didn’t profit from it, and even if you were personally miserable, we still might call you successful.

So, point is, if you want to be undeniably successful, you need to master yourself, and help others. Don’t focus on the money or the fame. Real success is mastering your emotions and actions, and actually helping lots of people.

Now, you asked, “What habits or skills are most important to living a successful life?” Well, by this definition:

  • The skill and habit of managing your state and your emotional reactions and actions
  • Knowing what people need in general, then what you need in particular.
  • People skills: how to see things from the other person’s point of view, and how to communicate from their point of view
  • The ability to focus, learn, practice, and apply what you learn.

If you can do those few things, you can do anything.

You can first be happy without depending on anyone or anything in particular.

Then you can understand what people need, learn how to provide it, and make sure they know it.

James Van Der Klip:

If you instantly lost all your resources, money, contacts, etc, had no possessions expect the clothes you’re wearing right now and $1000, and looked like a completely different person (i.e no one would recognise you) what steps would you take to become successful?


Notice how we all assume that when you say “become successful” you really mean “get rich”.

But as we covered in the last question, money is almost moot in what it means to be successful.

So if you took absolutely everything away from me, I’d still be successful, because I know how to be happy, how to be considerate, how to be useful, and how to learn.

Sounds like I’m being mister new-age positivity, but it’s really not. This was learned the hard way. I’ve spent years with very little, just a few hundred dollars in the bank. And now I’ve spent years with millions in the bank. Having millions gives you a nice sense of security, but when I look at my daily life, I’m not even using the money.

Here’s what actually makes me happy: a quiet little place to live alone, a working laptop, access to the internet and books, enough money for food, my health, and two good friends. Everything past that is kinda bullshit.

So if I had $1000 and these clothes, I’d already be successful. Successful at thinking, learning, and thriving. That’s all I need to be happy.

What would I do? I’d get any old job. Find an old used laptop for $100 and install Linux on it. Get a teacup and some tea. And get back to reading, learning, writing, thinking, and sharing what I’ve learned. That’s success to me.

My only expensive qualification is I like to live alone. So I’d use my programming skills in return for rent, so I could have my own place.

Even if I had no skills, like if you put me a few hundred years into the past or future, I know how to focus, learn, and practice. There are skills like sales and marketing, that everyone always needs help with.

Now if you’re talking about how to make a lot of money? I’d pick almost any of the paths online that aren’t a long-shot to mega millions, but just great proven strategies to pick a business and optimize it.

Kinda like diet and exercise plans, most of them work well enough if you actually follow through and do what they say, not just half-ass, but all the way.


What is something you believe that other people think is insane?


Oh that’s easy. I’ve got a lot of unpopular opinions.

I believe alcohol tastes bad. So do olives. I’ve never tried coffee, but I don’t like the smell.

I believe all audiobooks should be read and recorded by people from Iceland, because they’ve got the best accent.

I believe it’d be wonderful to move to a new country every 6 months for the rest of my life.

I believe you shouldn’t start a business unless people are asking you to.

I believe I’m below average. It’s a deliberate cultivated belief to compensate for our tendency to think we’re above average.

I believe the movie “Scott Pilgrim” is a masterpiece.

I believe music and people don’t mix. Music should be appreciated alone, without seeing or knowing who the musicians are, without other people around. Listening to music for its own sake, not listening to the people around you, and not filtered through what you know about the musician’s personal life.

I believe it’s unwise to prioritize lifestyle design, because it’s dangerously self-centered, and you are rewarded most in life for keeping your focus on being useful to others.

I believe loyalty is silly. We should constantly try to be disloyal, and only be loyal to the rare person, place, or idea that we’re just unable to be disloyal to.

I believe it’s good to feel smug. That means you’re proud of yourself, which means you’re living according to your beliefs.