Derek Sivers

Interviews → Ali Abdaal / Deep Dive

Fun conversation with one of my favorite people. My last interview for a while. On friendship, writing, music, goals, and more.

Date: 2020-05

Download: mp3 or mp4


(See the video on YouTube for some funny comments from the live stream.)


Hello, everyone. Welcome to this episode of Deep Dive, featuring the one and only Derek Sivers.

Derek, thank you so much for joining us.


Hey, Ali.


Can you give us a quick introduction to who you are and what you do?


Sure. Here’s my background in a minute or less.

Ever since I was 14, all I wanted was to be a successful musician. I was completely obsessed. That’s all I did until I was 28. At age 29, I had achieved success in music and bought a house with the money I made.

Then, I started a little hobby website to sell my CD called CD Baby. It took off and became the largest seller of independent music on the Web from 1998 to 2008. In 2008, after doing it for 10 years, I felt done.

So, I walked away, sold the company and have been an author, writer, speaker, pop philosopher guy since then.


I first heard about you through Tim Ferris’s podcast for the first time in December 2015.

And you wrote this book, Anything You Want which I often list as one of the three books that’s most changed my life. So, thank you very much for that.


I know people who have wrestled with writing books for ten years. I wrote that little book in 10 days. It was effortless. I didn’t think anything would come of it.

Seth Godin asked me to share my lessons learned and I spit them out into 80 tiny little chapters, and he published it two months later. I didn’t think it would go very far. It’s nice to see how it’s traveled.


Your book is subtitled 40 Lessons for a New Kind of Entrepreneur. I got a lot of business advice, but also a lot of life advice. When I reread it, it was an inspiration for how doable it seems to write a book.


Good. Some people think that writing a book is a big, serious thing. It’s got history behind it. It’s got these legends of writers going off into the mountains to sweat blood into the pages with their quill pen dipping into their veins, burning their soul onto the pages.

It’s much better to think not in terms of a book, but to think in terms of ideas that you want to share. For each core idea, make that one article – never more than one idea per article. If you have a second idea, you need to make that a separate article. Think in terms of articles. Most importantly, share the articles with the public as you go.

This way, you’re not putting yourself in a situation where all of your writing and ideas are jailed until your work is finally released. One idea at a time, you can put it out into the world and air it out. There’s something that happens when the public encounters one idea at a time. They might ask a few questions that you never thought of and it can help develop that idea before it’s a permanent inclusion in a book. Once you have all of the ideas that you feel make this book, then you can wrap a bow around it and call this collection of articles a book. You can call them chapters instead of articles.

It’s a healthier process than thinking, “I need to go write a 300-page book. This is going to take a long time.”


That’s interesting because for the last year or so, I’ve been toying with the idea of writing a book. I fall into this trap of considering it a really big deal. In my head, I think I need to spend a few months on the outline then a few months planning it…

A couple of days ago, I made a commitment to myself that I was going to write 1,000 words every day. For the last three days, I’ve been writing 1,000 words every day and having a low bar for the things that I’m writing. It takes me around 20 minutes. I’ve been thinking that this experiment would be a good time to get on with my book. I really like the way of thinking about it as one article at a time, with one key idea.


It also presents the ideas better. I often feel bad when I’m reading a 350-page book that has a brilliant idea buried on page 293. I know that hardly anybody reads that far in a book. Five percent of the people that buy a book actually read the whole thing. So, the number of people that are going to make it to that brilliant idea very near the end of the book are so few that I feel bad for that great idea.

That’s where I came up with this rule for myself to put one idea per article and make sure that each idea gets a spotlight in the world.


That makes a lot of sense.

I always advise people to put stuff out publicly for free. I’ve had a few people argue that you’re asking for others to plagiarize you work by doing so.

How do you think about this fear that some people might pirate your stuff?


There’s always an excuse to not do things.

People will say, “I’d love to travel around Asia, but what if I get diarrhea? What if I get lost?”

Everybody has a rationalized excuse for not doing something, but you have to have a certain confidence. There are many examples where authors have released their entire books for free and it actually boosted sales. Releasing individual articles from the book boosts attention and sales, too.

The contents of my next three books will all be on my site for free. But you have to click 90 different times to read 90 different articles, or you can spend seven dollars and lay down on the couch and read it. I’m confident that most people are probably going to spend the seven dollars to lay down on the couch and read it in one go, instead of clicking 90 times. That’s what I would want to do.

One of my favorite books by Seth Godin is called Small is the New Big, and it’s a compilation of articles from his site. I could have read it all for free with 130 clicks through his site, but I’d rather just spend a few dollars.

If you’re hoping to sell a $200 course someday, I can see the argument that you maybe shouldn’t put the entire contents of that course online for free if you’re hoping to sell it for a high ticket. But books are pretty cheap.


You’re working on three books at the moment. Can you tell us a little bit about those?

I’m curious about your setup for writing the books. On this channel, I like to talk a lot about favorite apps and those kinds of things. I fall very much into shiny new toy syndrome and when I decided to start writing, I spent hours and hours trying to figure out what tool to use before I thought, “Wait a minute…”


I only use plain text. I don’t use apps. I write everything in a Linux terminal looking like an old 70s Unix terminal using an old 70s text editor called VI. I type in plain text in the terminal entirely offline. Writing offline is my biggest productivity hack. When it’s time for you to write, power down your broadband modem. Cut yourself off from the world. Go to your phone and turn it off too. Make it so that you cannot go online. Then, you write.

As you’re writing, you’ll have those moments where you think, “Oh, I need to look that up.” We all have this habit of constantly thinking, “I need to research something. Yes, I’m writing, BUT what year did the Titanic sink? I need to know.”

You fall down a rabbit hole and stop writing. So, I write offline and when I think I need to look something up, I add it to a to-do list and look up those things later when I’m back online. What’s funny is how many of them disappear. I realize I really didn’t need to research this random topic.

As for apps, I personally see apps as the enemy. I’m using as a text editor from the 70s, and it works. I type my words into a terminal and it saves them in plain text. That’s all I need. Whenever somebody says, “You need this app. You need to organize your thoughts,” no you don’t.

People wrote with typewriters for a hundred years. And before that, they used a pen and a stack of paper. Just the fact that you have a word processor that can cut a paragraph and move it somewhere else is amazing. Any plain text editor does that.

What I like about not using apps, too, is that I really like to think super long term and equipment agnostic. Twenty years ago, I was a Mac guy. Fifteen years ago, I was a Windows guy. Ten years ago, I switched to Linux. Six years ago, I switched to Open BSD. I used to use Android for a few years and just last year, I switched to Apple for the fun of it. I may go back to Android. I like the fact that I’ve been editing my plain text files on all of those platforms. I’m not tied to any piece of overpriced hardware.

I could even switch it into new things that haven’t been even invented yet. New technology will come out and they will read text files because everything does. I’m not sure that new technology will read Scrivener. I see apps as the enemy of productivity.


Fantastic. Yeah, I think that’s the lesson that I definitely need to take more to heart.


Someone asked Seth Godin in an interview about the tools he uses to write, and he said, “I’m not going to answer that. You’re going to look for some excuse to buy something, thinking that because I use this, maybe you should use that. No, stop it. Use whatever you have. It doesn’t matter what you use. Don’t blame the tools.”

I read in a book once that real professionals don’t hide behind their tools. The author said, “Show me somebody using the fanciest, newest, top-of-the-line computer to make their art, and I’ll show you a procrastinator. The real professionals are just using whatever is around. It doesn’t matter. They’ve got something inside them that needs to come out. It’ll come out using whatever is there. It’s the amateurs who try to nerd out about their tools.”

You’re hearing a common theme here. These things are obstacles. They’re distractions. I try to eliminate all distractions, all obstacles, all of this nonsense that’s not necessary. I always think in terms of the minimum necessary to do my work and shut off the part of my brain that thinks it needs to find something new.


You’re working on three books at the moment. Can you give us any sneak peeks?


None of them are released yet, but two years ago I finished writing a book for musicians called Your Music and People: Creative and Considerate Fame. But what I love is that my non-musician friends who read the advanced copy say that it’s a great book about marketing and communicating in general.

When I was a musician, I read a brilliant book called The Inner Game of Tennis that was about your performing self, versus your over analytical self. Even though it was about tennis, you could apply its lessons to whatever you’re doing in life. Now, I wrote this book about music, but people can read metaphorically about creative and considerate fame in whatever you do.

My second book is called Hell Yes or No, which is a collection of my best 80+ articles from the past 10 years, which I found had a common thread around the subject of what’s worth doing in life. Those two books are done. They were supposed to be on sale two months ago, but I’m still tweaking my store where I’m selling them. I’m building my own store because I’m a nerd like that. So, any old day now, those two books will be ready.

You can go to and get on my email list, which is a private list. I don’t spam or anything. And I will tell you when they’re ready.

My third book is called How to Live. That’s the one that I’m still writing right now and I’m so damn excited about it. It examines 27 radically different one-sided arguments on how to live with one succinct conclusion.


That sounds very intriguing.


I’ll be in solitude writing and shrieking with excitement sometimes because it’s so much fun to write. I can’t wait to finish it.


I can’t wait to read it.

I’m fascinated that you’re coding and building your own store.

I read something that really resonated with me about this subject – if you sign up to run a marathon, you don’t want to get a taxi to take you to the exit. That sort of thinking is probably in action with you building your own store.


I met a tailor in London who not only makes clothes for other people, but he makes all of his own clothes, too.

When I met him, he was wearing what looked to be a normal polo shirt.

He said, “I made this shirt because most polo shirts don’t have this kind of color.”

Is that efficient to make your own clothes? No, but it’s what he loves to do. There’s more to life than efficiency. Sometimes you do things just because you love doing them. I’m very process driven. I do things for the doing, not for the goal. There have been many projects that I finish 90-95% of it and shut it down because I finished the fun part. The actual launching didn’t matter to me.

My books are also translated into 25 languages. I built a whole translation system to manage all the translators, too.

Every sentence in the book is saved in a database. Now, I can look up any English sentence I wrote and see that sentence in 27 languages, which really helped when I had to make an edit to the book and I had to cut out a paragraph. If my system wasn’t like that, it would’ve been really hard to find that paragraph in Arabic, or that paragraph in Chinese to cut out. Because it was mapped per sentence, it was easy to do. It’s going to be fun for learning languages later when I’m learning Portuguese or Mandarin. I can use my own sentences for language learning.

I had around 65 different translators crowdsourced and working on this, 55 editors, and 100 reviewers. I built the whole system to manage all of this, and it was really fun.

Now, I’m putting the finishing touches on the store. I enjoy that I get to do some things that you can’t do at Amazon. For example, I can do custom dedications. If you buy the book from me, you tell me how you would like to dedicate it, and that’ll be the first page of the e-book.

I got so excited realizing that I can do that with the audiobook, too. If you buy the audiobook from me and request a custom dedication, I turn a mic on, hit record and upload it to my server.

It merges it with the Master WAV file of the audio, compresses it into an MP3, and now when you download your audio book, in your intro is my custom dedication.

That stuff excites me so much more than putting it on Amazon like every other person. I really like the clunky, DIY, “we don’t need the man,” type of ethic.


You’ve said in the past that the era of Internet you grew up in was very different. It was very much about individual creators.


Especially in music. In 199,4 it was exciting because the Internet was so new, it didn’t even have graphics. It was just text but that was exciting in itself because you got to connect with people around the world.

Around 1998, when MP3s became a thing, it was super exciting because every musician went, “Oh my God, I don’t need to sign my life away to EMI or Warner Brothers. I can distribute my MP3s directly to my fans or use the Internet to sell my CD directly and mail it to them. I don’t need a record label. I don’t need distributor. We don’t need record stores. I don’t need a publisher. Wow, I don’t need to sell my soul anymore. This is amazing!”

Self-distribution was a huge revolution. I was so happy to be right in the middle of that scene. It was a renaissance – a blossoming of entrepreneurial spirit. Everybody was doing everything themselves and it was so cool. In 2007, Facebook started to get more popular and things started to get more centralized. That’s when it started to feel corporate and icky to me.

So, I don’t care that what I do is unpopular. It makes me happy to do things myself with a do-it-yourself work ethic.


That reminds me of the idea that the only point of doing anything is to make it make you happy. Therefore, just do what makes you happy.


Yes, profits are important in a way, but the reason you want profit is to be happy. When you do what makes you happiest, it puts fuel in your tank. It gives you that gold power. It makes you excited to get up and do things. If you’re trying to optimize everything for maximum returns because somebody tells you this is what you should be doing, it can be depressing. You find that you no longer want to get out of bed in the morning. You’re not excited about what you’re doing.

Whatever excites you the most is what you should be doing.


I often get questions from students struggling with productivity or motivation. They see what I’m doing the Internet because I’m a doctor by day, and I do this YouTube stuff in the evenings. And they ask, “How do you have time for all of the stuff?”

I find it quite hard to answer because in general, I don’t really ever do something that I don’t want to do. So, I wonder what you’d say if someone asked, “How do you force yourself to do something that you actively don’t want to?”


Sometimes you have to push yourself through something you don’t want to do. I’m not sure what you do, but I will literally yell out loud at nothing. I kick the floor and then I think, “Alright! I’ll get some caffeine. And then I’ll just do it. I don’t feel like doing this, but it needs to be done. Here we go.”

But that’s a few minutes per week or maybe a few hours per week tops. And usually, if we personify the muse as inspiration, she’ll meet you halfway. When you sit down to do something, even if you don’t want to do it, you have to get over the initial hurdle. For example, jumping into a cold pool. Once you jump, it’s cold for the first ten seconds, but once you’re in and it’s like, “OK, this is this is actually alright. But damn, that first 10 seconds really sucked.”

The inspiration usually meets me halfway, and I don’t spend hours cursing and yelling each day. It’s only for a few minutes when I have to get started.


You wrote an article titled, “Don’t Quote. Say it Yourself.”

I have a long list of mentors who I quote from regularly. I often find myself wondering if these mentors really care that I’m quoting. But I feel that I should give them credit. What do you think?


I used to do the exact same thing to a fault. I would hear myself telling friends a whole bibliography about the person I was quoting before I would even get to the point.

One day I thought, “I should just say that sentence, shouldn’t I?”

The idea is not to hide the source, but not to force that on someone who didn’t ask for it.

I think of the metaphor of eating at a restaurant. Imagine if it was the norm that every time you went to a restaurant, you ordered a meal. When your food came out to you, the chef would also come out and say, “OK, what you’re eating here? We got the lettuce from the Wilsons farm, which is about 30 miles down that way. We pick the lettuce and it came to us on a truck that was run by the Miller Shipping Company. Now, these parsnips came from over here. And in the kitchen, a man named Jeff chopped them up. We got the chicken from this farm. The chicken’s name was Tracy, but now she’s dead.”

You’d be saying, “OK. Can I eat now? I came for this meal. I didn’t need the whole history of where every ingredient came from. If I want to know, I’ll ask you. But if I don’t ask, you don’t need to tell me the ingredients and the source of every ingredient in my meal.” That applies with the ideas and the stuff we’re sharing, too.


How do you think about it when writing a book?


If I were to attribute every sentence to its source in this third book I’m writing called How to Live, the page would be littered with sources. Instead, with each idea that I’m tempted to quote from somebody, I go through a really deliberate process of adopting it.

Again, I like this metaphor of adoption – think of it as adopting a child, or an animal, or whatever you want to use? I’m going to adopt this idea and now it’s mine. I know that it originally came from somewhere else, but I’m going to fully embrace it as my own now. I’m not using it word for word. In fact, I’m going to alter it a little bit.

For example, Oscar Wilde may have said it well, but I think I can say it a little better or mix it with my point in a new way. Sometimes I do get ideas from books that are long winded and have a flowery sentence structure that I don’t like. I don’t want to quote that exactly, but I like the seed of that idea. In fact, I get to mix it with this other idea over here. Now, the combination is my own unique thing.

By default, I won’t quote others unless you really ask me, “Wow that’s a really interesting idea. Where did you think of that?”

I’ll say, “Glad you asked. It’s from this book…” Now, I can tell you the background because I know where everything came from.

Musicians are the same way – every idea, every melody, every note, every lyric – musicians usually got it from somewhere else. They heard this Joni Mitchell song and mix it with parts of a Beck song, add in this and that, and it comes out as their own song. They know what their sources are, but the combination comes out sounding unique. If you really ask them to dissect it, they’ll tell you where they drew inspiration from. But you don’t need to bother people with that. They don’t ask.


You were a professional musician for much of your early life. Why don’t you identify as one anymore?


Until about a year ago, I still thought of myself as a musician. Then I had a funeral for the title.

I was very torn between writing and making music. My instruments were sitting in front of me, and every day I chose writing over music.

Every day I felt bad about it until I finally had a moment where I told myself I was going to get really serious about music again.

After that, my very first thought was, “But this is time I could use to write. . . If you don’t want to make music, why are you forcing this? It’s my identity. I’m a musician. But what would happen if I gave away all my instruments? That would be a huge relief!”

So, I gave all my instruments away. I called my friend who’s a professional musician in Oxford and asked him if we wanted all of my instruments and speakers.

He said, “Dude! Are you serious?! That would be amazing!”

I said, “OK it’s all yours!”

I wasn’t using it and now he’s using it every single day. He loves it and it changed his life. That was about six months ago. It felt amazing. But it definitely meant a little mini funeral for that identity of mine.


That’s exactly how I’ve been feeling about being a doctor.




Genuinely. It’s such a big part of my identity and “brand.” I’ve been a doctor for the last two years and I’ve been thinking about taking a career break to figure out what I want to do long-term. I’m thinking it’s a very reasonable time to take a break and see what happens.

I’m not holding the funeral just yet, but at least I’ll give it a shot and see what unemployment and being a citizen of the Internet is like, and then take it from there.


I reverse and ask myself, “What do I hate not doing? If I were to remove everything and give myself a big blank slate in life, what would I hate not doing the most? I find that a more useful question to ask.

But wow, that’s tough because with something like music you can say, “OK, it’s not going to be my primary thing, but I’ll dabble here and there.

You can’t say, “I’ll be a doctor as a hobby here and there when I feel like it. I’ll stop in and see if anybody needs any help.” I don’t know how that would look.


That’s sort of the direction I’m heading with it. Especially in fields like anesthetics and emergency medicine and even general practice.

There’s a lot of people who now have what will be called portfolio careers. They do medicine maybe two days a week and then run their wine business on the side for two days a week and then make some music on Fridays.


Wow. That’s really cool.


I’ve been taking singing lessons for the past few months and I’ve dabbled in music since I was I was a teenager and I want to get better at it.

I missed the boat on music theory and actually knowing how to read music. It’s frustrating.

How important is music theory when it comes to producing and singing and creating?


Music theory is like language grammar. If you were to ask to ask a linguist, they’ll tell you that there are about 6,000 languages in the world and only a few hundred of them have ever been written down. Most active, living languages in the world today have never been written, and therefore most languages today have never had a codified their grammar.

But most of the languages in the world, people learn to speak without knowing if what’s a conditional verb, people just listen and speak it. Same thing with music theory. Music theory always comes later to analyze what’s been done, and to give names to things that people did intuitively so that they can turn it into a lesson and teach it to somebody else.

But all of that is later analysis that is absolutely not necessary to the playing or even the learning of music.

My best advice is to analyze your favorite music and make up your own system for writing. The whole reason that we have the sheet music with the treble clef, the five lines, and the dots and the circles with the flags was to make a universal standard so that people like Mozart could write out his sheet music and hand it to a bunch of musicians that aren’t going to be there with him and didn’t have a recording.

But you’re just you’re not going to be writing parts for cellists, you’re going to be doing this for yourself. So, take your favorite song or each of your favorite songs and make your own system for analyzing them on a piece of paper in an hour or so.

Notice and pay attention to the organizing of instruments – the layering. Sometimes I love listening to these arrangements where something comes in for eight bars and you think the songs going pretty well and then something else comes in for the next eight bars and layers it. Then, that thing at the beginning drops out, leaving only the second thing. I’ll enjoy writing this analysis on a piece paper just to see the way that instruments are dropping in and out of the arrangement and to see how they build and then where they all drop down.

Then, I’ll use some of these ideas for the arrangement in my own productions. You could analyze the hell out of things without needing to do any of the standard music treble clef, note reading notation, and definitely without music theory. Whenever you hear something you like, you stop and poke around and find that chord. Sometimes there are things that we don’t even really know how to analyze.

I am very, very versed in music theory. I went to Berklee School of Music. I got a bachelor’s degree in music.

And yet when I hear the song Lithium by Nirvana,

“I’m so happy ‘Cause today I found my friends They’re in my head.”

[Sings notes]

It makes no sense. I have no idea what the hell he’s doing there.

I don’t know what kind of analysis you would put into this chord progression, but damn it sounds so cool.

It sounds awesome. All of this music theory is just a way to kind of turn things into workbooks to teach students. But you don’t need that.


I was watching an interview with John Mayer a few days ago, and he said something almost identical. He also went to Berklee. He was saying that when you’re listening to a song or learning how to play a song on the guitar, don’t just memorize the finger deposition. Think about what that chord is and why they chose it. Then think about other ways you can make that chord. Eventually, if you do that enough, you develop your own music theory and you don’t have to read a book about it.

He was saying he didn’t really care about music theory despite having gone to Berklee.


Cool. That is a good example, especially on guitar. It’s good to go through chord progressions that you might have learned down at the bottom of the deck on a beginner acoustic guitar. Now, play those up higher on the neck with the same chord progressions. That can be a fun example. It also brings out different notes with the melody. Next thing you know, you’ve written your own song.

I listened to an interview with the Rolling Stones when they first got famous. Keith Richards and Mick Jagger said that they never even set out to write original songs, they would just play songs by their heroes. By jamming and playing, their own somewhat unique song would accidentally tumble out of the mix. That’s how they would write songs – by imitating their heroes and their own thing tumbles out.


I love that an original song is just a remix from different sources.


The biggest pop songs of all-time sound like nursery rhymes. They’re so simple. And you guys might offer the story.

When Paul McCartney came up with the melody for the song Yesterday, he thought, “This is too good. Somebody must have written this already. This can’t be original.”

He went around singing it and asking everybody, “What song is this?” Finally, he said, “I think I wrote this?” but it didn’t even feel original to him. It felt like he had heard it from somewhere. But no, he accidentally wrote Yesterday. It was called Ham and Eggs at first. Later, he came up with better lyrics.


You’re a pretty good singer. Were you born that way?


No. I was a horrible singer at the age of 15. I was just like a heavy metal guitarist and my guitar teacher at the time said, “You’re going to have to learn how to be a singer because if you don’t learn to sing, you’re always going to be at the mercy of some asshole singer.” [Laughter].

I took that to heart even though I had no desire to be a singer at the time, but I didn’t want to be at the mercy of some singer either. So, I started singing and I was terrible. I took voice lessons every week or so for 15 years. Every single night I would go into a soundproof practice room and sing my arpeggios and my scales [singing]. Then, I would do tone practice which is where you experiment with opening or tightening your throat to get different tones out of your voice.

What I love about techno music is how they play with timbre. [Singing] That was all one note. But they’re just bringing out the treble, rolling it back. Cutting it off.

You can do that with your voice, too. Pick a note and sing that note in as many different ways as possible. And it’ll sound terrible. You can imitate your heroes. Try to sing like Stevie Wonder. Teachers will point out that singers like John Lennon sings through his nose and Paul McCartney sang in his throat. So, I nerded out on this for 15 years.

Although I loved doing it and I was determined to be a great singer, for 15 straight years, everybody who would hear me sing would say, “You’re just not a singer. I hope you find a real singer someday because you’ve got pretty good songs but you’re just not a singer.”

I was unfazed. I said, “I don’t care. This is what I love doing. I’m going to do it.” Sure enough, I really like the vocals from the last few songs I ever recorded before I accidentally started CD Baby. When I hear myself sing now, I feel like I finally got it.

For most people it doesn’t take that long. You’ve got a good voice to start with. You can hear certain people have a speaking voice. It’s already pleasing to begin with. You’ve got a head start.


Thank you. For the past couple of years, I’ve been posting my singing on my Instagram occasionally, and people are so nice and supportive. But occasionally, I’ll get like a couple of people saying, “Hey, man. Stick to productivity advice.”

I know I shouldn’t care, but I have imposter syndrome when it comes to singing because it’s not a big part of my identity at the moment. But it’s very reassuring to hear that you worked at it for 15 years before you thought that you were reasonably good.


Two hours a night for 15 years. I was driven. It can take a while, but I think you’re doing the right thing by putting it out there. It also helps to remember that it’s something that you enjoy doing for its own sake. It’s process driven, and not just a goal.


You mention that you don’t need to make a living from your hobbies because by trying to do so, you’re actually going further away from the art itself and much more towards the business side of things, which might ruin the passion.


Most professional musicians I know only really spend one to three hours a day actually making music. The rest of the time is spent managing their career. The happiest people I know are the ones who make a living doing something that pays well, and they do their art for the love of it. They’re not trying to make good money doing it.

That said, you have to take the art seriously to be fully enriched. Shallow happy versus deep happy. Sometimes, deep happy comes from doing the more difficult thing. Take your art seriously, even if you only do it at night. Release it to the world and try to sell it. But you won’t be depending on it for an income because you’ve got this other thing in the day that that pays your cost of living. That balance is healthier. And like I said, the happiest people I know are the ones that have balanced those two things.


Awesome. So, we’ve talked about writing and music. I want to shift gears and talk about making friends.


You and I met in April of last year. I’m not just saying this because I’m talking to you right now, but you were one of the coolest people I had met in a long time, and the first guy I had met in a long time where I felt like I really wanted to stay good friends with you.

We talked into the night in Cambridge, and I didn’t want to leave. I thought, “Wow that was a great conversation! He’s really, really cool.”

I almost never add anybody to my phone, even when I meet up with people. I retrieved phone numbers, but I don’t actually add them to my contacts. I actually added you to my contacts because we need to be real friends.

It’s cool that when you emailed me about coming on your show, you said you wanted to talk about friendship. Not only do I have a lot to say about that, but how appropriate that it’s you who is asking me.


Oh wow, thank you! That’s incredibly kind of you. When we met, I really enjoyed our conversation. But I was so worried that I would come across as a fan because I was like a huge fan of your work and I really didn’t want our conversation to become like a podcast interview. I was having a lot of fun talking to you, but I was also really overthinking things, “I don’t know if he likes me. I really want to be his friend!” [Laughter].

And then at the end of our conversation when you said that you enjoyed the conversation and that I should consider you a friend, it made me so, so happy.

What does friendship mean in your book?

Because I know that you consider yourself a citizen of the Internet rather than a citizen of any particular location. How does making friends come into that?


First off, the word “friend” is too vague. It should have many subdivisions, like the French language. I learned a recent lesson – just because somebody is smart and a good conversationalist, doesn’t necessarily mean that you’re going to be good friends.

The number one thing in friendship is emotional safety. I could meet a different stranger every day and have good conversations and feel friendly with everybody, but there’s a tight, inner circle of people that you actually feel emotionally comfortable with. These are the people you could call when you’re really down and need to be selfish and say, “I really need to talk.”

You know you’ll feel safe, even when you’re not your best self. I’ve been thinking a lot about that because I meet many smart, interesting, cool people. It’s always sad or strange to notice the ones that don’t turn into friends because it just stays at the interesting conversational level and doesn’t get to the emotional safety level. So, that’s one side of your question.

I’d say almost all of my friends are people who have initially either reached out to me because they heard something that I put out in the world.

A few of my best friends are people who I reached out to because I liked something they put out into the world. It could be a book that I read and loved, so I emailed the author and said, “That’s brilliant,” and then we trade a few emails back and forth. But there’s always that stage where you’re at an arm’s length distance emailing, you get the feeling that this is a really cool person. Then, somebody has to suggest taking it to the next level, like talking on the phone.

I really like talking on the phone. My friends are spread out around the world. My best friends are practically on five different continents and in five different countries, so the phone is crucial to me. If somebody doesn’t like the phone, we’re not going to be friends. I’ve met some people who were really cool where we’d stay up into the night over drinks in a square talking.

But when I said, “We should talk on the phone sometime,” they said, “Oh, I don’t do the phone. . .”

OK, then we’re only going to be surface level friends.

Somebody has to suggest taking it to the next level. Either let’s talk on the phone or let’s meet up.


It’s a really interesting point that someone has to suggest taking it to the next level.

We all know that feeling of slight anxiety when meeting someone new and you want to be their friend.

It requires some level of vulnerability to sort of put out the suggestion that, “Hey, we should meet up outside of work,” or, “Do you want to chat on the phone sometime?”

I kind of get the impression that you’re OK with exposing yourself in that sense.


You have to.

This is from my American point of view. I know it’s not classic British reserve [laughter].

I’ll tell a few quick, colorful examples.


Somebody mentioned me on Twitter recently and I thought, “Hmm that name sounds familiar?” I found out she wrote one of my Wood Egg books – I had a publishing company six years ago – and she wrote one of my books. Now she’s living in Oxford, England, and I live in Oxford.

This happened about a month after I got here. I messaged her and said, “I’m the guy that hired you years ago to write this book. I live here in Oxford now. Are you really living in Oxford?”

She said, “Yeah. My God, do you live here?!”

I said, “Here’s my local phone number. Let’s meet up.”

It turns out that she has kids the same age as my kid. So, we met up at a playground to let our kids play. I had low expectations. I didn’t know anything about this person except that I hired her years ago to write a book. But as soon as we met, I thought, “Wow you’re really, really cool.”

It’s like when you and I met. That initial thought of, “Wow, you are exceptionally cool. I like you more than I like most people!” It was something about her right away.

We let our kids play and when it was time to go, I said, “Hey, I really like you. You’re a really cool person.”

She goes, “Oh my God, I’m so glad you said that. I feel the same way! My husband and I moved back here from Hong Kong only a year ago, and we haven’t met many people we like here. I was having the same feeling about you, that you’re a really cool person. I had no expectations.”

I said, “Yeah same here.”

She goes, “OK, I think we’ll be friends.”

I said, “Yeah, we’ll be friends.”

Her husband is actually the one who I gave all my musical instruments to.

If I was giving this example to somebody else, I would tell the story about you and me. I was coming to Cambridge to speak at a conference and I reached out to you.


Around that time, I released a video called Three Books that Changed My Life, and your book was on the list. Someone mentioned both of us in a tweet about my video, and then you replied to that tweet saying, “Hey, Ali, I’m going to be Cambridge, too. Do you want to hang out?”

And I thought, “Oh my God, mind blown!” [Laughter].


Here’s another good example. Somebody sent me an email saying that she really liked my book reviews on my site and that they changed her life. She said she admired the fact that I put my email out there publicly because she gets a lot of e-mails from strangers and she knows that if she were to receive an email like that, it would be weird, too.

I looked at her email signature, and she’s this famous Olympic athlete. Then I looked at her work online and read her bio and thought, “Oh my God, you’re amazing. You’re inspired by me?”

In that case, I emailed her back and said, “Here’s my phone number, we should talk.”

She called me the next day and we talked for three hours that night, three hours the next day, and three hours the next day. It actually turned into a full-on romantic relationship for years. And it all started because she reached out.

Another good friend of mine wrote a book that I absolutely loved. I emailed the author, totally put him on a pedestal, and said, “Oh, my God, I read your book. I absolutely loved it.”

He wrote back saying, “Oh, my God, I read your blog. How cool that you know my book!”

We decided to talk on the phone. Then, we talked for a few years before we finally met up in person when we were finally in the same country. In fact, two or three of my best friends now are people who I met randomly online by one of us encountering each other’s work and we’ve only talked on the phone for years.

One of my top five best friends, I’ve never seen in person and never even clicked the video button on our calls. It’s been an audio only friendship for five years now.

The point is, you should reach out to your heroes and to people that you feel a connection with online. Introduce yourself and say “Hello,” because you probably have a lot in common. The reason that you were drawn to this person’s work is because it really resonates with you. You’re probably the type of person they’d like to know, too.

Be careful not to put people up on a pedestal too much. By doing that, you put yourself below that person in your mind, and nobody wants to be friends with somebody down there. You want to be friends with somebody that you’re seeing eye to eye with. My advice for when you meet people that you look up to is to fawn over them. Talk about anything else, talk about random surroundings. That’s where you’ll actually connect more than, “Oh, my God, I love your book!”

It doesn’t mean don’t say, “I love your book,” because if you love my book, you’re probably a pretty cool person.

I’ve tried not fawning when I was with people whose work I really admire and because I don’t put them on this pedestal, it became a real friendship with the emotional safety. It turned into a real friendship, which is always more emotion based than intellect or success based.


What’s your process for talking to people on the phone? Do you randomly ring them, or do you text message back and forth? Do you schedule a calendar?


I have such a strong opinion on this.

It’s funny, we all have phones where we use so many of the buttons, except that one that’s in the shape of a phone. Nobody ever uses that button. Everybody is scared of that green button with a picture of a phone on it.

I’m a little weird like this, but here’s my opinion.

You don’t need to text somebody to ask if they can talk because the sound of a ringing phone is the inquiry if they can talk. If they can’t talk, they hit decline. You don’t need to make it a separate ask. Maybe the first time you talk on the phone, you can text first to ask if they’re free.

I’m so glad you asked this because I have a great little story tell. A very famous Broadway musical writer is one of my best emotional friends. I’m not saying that to namedrop or impress, but because the reason we met is that I bumped into him at the TED conference and I said, “Oh my God, you’re the guy that wrote these musicals?!”

It turns out that he knew CD Baby, and we had this great conversation for an hour and then traded phone numbers. For the next year, I just had him up on this pedestal thinking, “He’s very famous and very busy.” I would text him saying, “Hey are you free to talk next Thursday night?”

I loved his reply. After a while of asking this, he finally said, “Derek, I’m your friend. Call me at 2:00 in the afternoon or 2:00 in the morning. Wake me up in the middle of the night if you need to talk. I would love to talk to you in the middle of the night if you need to talk to me. I’m your friend. You’re my friend. Don’t ever ask. Just call. I adore you and would always love to hear from you. Just call.”

I thought that was really sweet. It was one of the nicest things anybody’s ever said to me. I said, “OK. Deal.”

Once I said this, he started calling me at 3:00 in the morning. I’d wake up and answer the phone. He’d say, “Hey man, can you talk? I need to talk.”

I’d say, “Yeah. Give me a minute. I have to wake up,” and then we’d have a 90-minute conversation because he was sad about something.

I thought that was really sweet. A 3:00 in the morning phone call – that’s a real friend. And we need that. People are too scared to bring people into their inner circle. I’m so glad you asked us to talk about it. Nobody talks about any tips, and nobody talks about friendship.


It’s all very strange the way we feel one way about something, and we assume that other people feel a different way about it.

It’s one of those asymmetries. Even though you gave me your number and said, “Call me, we should hang out,” in my head I think, “He can’t really mean that. He must be such a busy guy. He’s writing his books. He’s got a kid. He’s doing lots of stuff.”


[Laughter] We all do that.

That’s why I included the detail that my friend is a famous Broadway musical composer. I was intimidated and felt that he was totally swamped. But everybody makes time for the people that they love talking with. It’s rejuvenating to talk to people you adore. You always have time for rejuvenation.


You mentioned a phrase, “Weird like me.” What does that phrase mean?


I think a lot about kindreds.

I had a specifically weird thing in common with the writer in Oxford who wrote the Wood Egg book for me. She asked, “Why did you leave America?” I said, “Have you heard the phrase, burning the ships?”

She said, “Oh, my God. I was just researching that phrase this morning! How weird that you’re talking about that. Why do you mention it?”

I said, “When I left America, I wanted to burn the ships behind me.”

Do you know the story of burning the ships?


No, I don’t.


We all know the phrase burning bridges. The phrase burning the ships is when you make a drastic move to prevent yourself from retreat. It’s a reference to some Spanish conquistador that went off into South America with 100 men on his ships. But when they arrived, there were 10,000 Aztecs waiting to kill them.

The conquistador said, “We must not retreat from this. Send one of the men to burn the ships to show the soldiers we have to push forward. We cannot retreat to the homeland.”

Somebody burned the ships so they couldn’t retreat, and they won the battle. Whether that was for better or worse, historically – that’s a separate story. So, the phrase burning ships means to dramatically cut off your options. And that’s what I did when leaving America 10 years ago. My friend said she just had that discussion with her husband that morning about burning the ships because they left Hong Kong.

So, we instantly have this weird thing in common. She’s said, “All my friends think I’m really weird for leaving Hong Kong.”

I said, “All my friends think I’m really weird for leaving America.”

We both had this thing thought of, “Wow, you get this weird thing about me.”

It’s a relief to know that there’s this thing about yourself that other people find weird that you might have to explain to some stranger and feel a defensive struggle to explain yourself. But when you meet somebody who’s weird like you, it’s like, “Wow. What a relief. I don’t have to explain myself to you. You get it.”

For example, with the Olympic athlete who I mentioned earlier, we fell in love after a couple phone calls. She’s an absolutely monomaniacal, driven, ambitious person just like me. I’ve always been so weird like that. My friends say, “Dude, relax, just chill. Get a nice, work-life balance.”

In fact, she took it even further than me. It was such a relief to meet somebody else like that. I said something to her once about hanging out. She said, “Hanging out. You mean people who sit on couches? No, I did not do this. I do not sit on couches. Life is too short.”

I thought, “Yes, you’re so cool. I love this. Somebody gets it.”

The people who have kindred interests are weird like you.


I’ve definitely found that as well. That’s one of the things that I like most about dabbling in different areas of interest.

I started dabbling in music and dabbling in tech stuff. And then the YouTube channel. You have a shared language with other people. It’s a thread that’s ties you together.

My brother and I often notice that when it comes to making friends, we are more instantly comfortable around other ethnic minorities. Even though we don’t experience much outward racism, the experience of being an ethnic minority in the U.K. does, in a way, give you some similarities and shared experiences with other people who are ethnic minorities. In university, I was part of the Islamic society. Whenever I’d meet someone from the Christian Union, we get along very well because you’ve got this shared generally religious sort of vibe has a kindred spirits sort of feeling.


That’s really cool. That’s a good example.


You lived in Singapore and New Zealand. Can you talk about making friends in both of those places?


In Singapore, I got deeply involved and was interested in the people. New Zealand was the opposite. I love both countries, but for opposite reasons. In Singapore, I feel deeply connected with the people. The whole reason I love Singapore is for the people.

When I went to New Zealand, I fell in love with the land. I’ve never been so in love with a place and felt so connected to it. But it was also because I was at an anti-social time in my life. I just had a baby and I wanted to be a very present, full time father. So, I was totally anti-social and not part of the local community.

New Zealand people would ask me to meet up and I’d say no. In Singapore, when people wanted to meet up, I’d say yes. I met up one-on-one with around 500 people in Singapore. But in New Zealand, I met up with three people in the six years I lived there.


I have a sentence buried in the About Me page on my website saying, “If you happen to be roaming around Cambridge, drop me a message and I’ll buy you a coffee.”

Over the last two years, pre-lockdown, I’ve met up with at least 30 or 40 people after work on random days. It’s been very fun. And people think that’s weird. They say, “Why would you meet up with random strangers on the Internet?”

I think, “Why wouldn’t you meet up with random strangers on the Internet?” Sometimes, we meet up for coffee, have a great chat, and I invite them over to my place. One time, there was a student who was visiting the UK from America and we chatted until midnight and he missed the final train back to London. So, he slept on my air mattress and went home the following morning.

My mum said, “What the hell? He could have been anyone!”

I said, “Well, he went through the effort of finding this niche page on my website and emailing me. How bad can it really be?”


[Laughter] You hit the key point. This is somebody who found your site and went to the About page. That shapes a lot of this conversation we’re having about friendship, too. It really narrows it down in the world when people took time to check out what you’re putting out into the world, then went to your site and clicked around.

At the end of all my podcast interviews, I always make a point to say that if you made it all the way to this end of this interview, send me an email. If you listened to this whole conversation, I’d probably like to meet you. So, I will say that right now [laughter].


You reply to every email you get. Why do you do that?


It’s a matter of who you want to be in the world and how you want to be. Tim Ferris, my friend Ramit Sethi, they like this auto responder, you can’t reach me thing. I don’t like that. I wouldn’t feel good about that. I would make a change in some other way in my life if I felt that I was so famous that I needed an auto responder. I would find a way to be less famous.

First and foremost, I like being the guy that replies to every email. Everything else I can say will rationalize that. I get a deep sense of happiness from all the people I know around the world.

I have a system that I built. At its core, this system has a database of every single person I know. So, every email that comes in attaches itself to this central database. That’s where I keep what I know about this person. I can get an email from Jennifer from 12 years ago and as soon as I get it, I know it’s Jennifer from Alaska, the girl who emailed me 12 years ago about thinking of majoring in music at Berklee. I can see our past emails and reply, “Jennifer, good to hear from you again. What’s going on? Did you go to Berklee? What’s up?”

It can honestly be deeply rewarding to see this human history and feel a connection with these people. I also love knowing people from around the world. Minutes before you and I connected, I checked my email one more time and there was like an email from some guy who was a metallurgist in Slovenia. I thought, “Cool! I know a metallurgist in Slovenia now.”

In fact, some people who have heard of me through your show have emailed out of the blue. They’ll say, “Hey, I’m in Saudi Arabia and I found you through Ali Abdaal’s videos.”

How cool. I know somebody in Saudi Arabia. If I were to ever go to Saudi Arabia someday, I could reach out to this guy. I actually do that when I’m traveling, especially if I go somewhere I’ve never been before.

I’ll go to my database and see who I know in Salzburg. “Hey Jen, it’s Derek Sivers. I’m in Salzburg for a few days. Do you want to meet up?”

It’s really fun to turn these random email connections into in-person connections. I get a lot of deep satisfaction out of these connections. It takes me a couple hours a day tops to do all my emails. Sometimes just 20 minutes, but when it gets really extreme, it can be 12-hour days of emailing. It’s exhausting. But it’s worth it to me.


I first emailed you after your interview with Tim Ferriss, where you suddenly opened the floodgates to many emails.


I didn’t realize his show was so popular! [Laughter] Tim was an old friend of mine. I didn’t know anybody listened to his podcast.

Talk about 12-hour days – after that podcast came out around Christmas of 2015, I’ll never forget that. My next two months, full-time, 12 hours a day, six days a week, I answered e-mails from his podcast. My God.


I remember getting a really thoughtful reply back from you and I was thinking, “Wow, this guy must be getting thousands of emails right now.”

That inspired me to also try my best to reply to as many emails as I could. Up until a certain point, I was very proud of that. I was replying to every Instagram direct message that I was getting until it started to get super, super, super overwhelming. Then I realized it would be a full-time job to reply to these emails.

I imagine you get a lot of emails from people asking you for life advice. How do you deal with that?


For me, I think of it as writing prompts. If someone is asking me a question that I’ve already answered in an article somewhere, I keep my URLs handy and I send those. I say, “Good question. Here’s the answer. Read this,” or “Read this book. It answers that better than I could. Let me know when you do.”

That handles more than half of them. For the rest, I take it as a writing prompt. Sometimes I’ll let emails sit for a week because somebody will ask me a question or two that’s really good. Instead of answering in my email client, I’ll open up a new text document and I’ll think around the subject and might even spend two hours on it. I’ll spend two hours writing what turns into an article and then I post the article and then I’ll send them the link and say, “That was a really good question. Thanks for the prompt. Here’s an article that I wrote inspired by you.”

You’ll notice that a few times in my articles, I’ll note that somebody asked me a question and here’s my thoughts. But, it’s always easier to give advice than to take it because you’re detached from the person. You’re seeing it from a distance. Whereas inside your head, you’ve got such a tangled mess of concepts in there that it’s hard to figure things out for yourself.

When you see somebody else’s situation from a distance, you can see the overarching theme. By giving someone else advice, you’re actually being your highest self. You’re giving the best advice because you’re emotionally detached. The emotions aren’t confusing you because it’s just an email.

I find it useful that you can take your own advice when you find yourself in a pickle. And yes, you’re filled with emotions about this, but you can think for a second that, “If I were a stranger emailing myself, asking advice, I would say to do this, therefore, I’m going to take my own advice and do that.”

So, I find it useful to give advice. Because it puts you in your highest self and then you can take your own advice later.


Do you ever get a sense of imposter syndrome and ask yourself, “Why do these people think I’m qualified to comment on this issue?”


No, because I do it, too. Every time I get stuck in a situation, I think about my heroes. I ask myself, “What would this person say?”

Sometimes I write an email to one of my heroes to answer to my predicament. But then I’ll think, “I’m going to waste his time. So how can I make this as simple as possible?”

I’ll simplify it, and then before sending it, I think, “Well I know him pretty well. What will he probably say to this? I’ll address what I think he’s going to say.”

Then, I say, “OK. Now what will he say? I think I know what he would say to that, too. Never mind. I don’t need to bother him with an email at all.”

I channeled him enough in my head to take his imaginary advice.

When somebody e-mails me their predicament, I get it. I know how it goes. And I’m happy to help because I’ve been in that position.


The idea of goal setting is very popular. Every business book, apart from yours, says you must set goals that are smart, specific, measurable, achievable, and have realistic timing.

What is your view on goal setting? When it comes to my business, I think that numerical goals can be a bit pointless.


Imagine you bought a car, and somebody says, “We need to optimize this gas mileage. We’re going to get you the maximum miles per gallon out of this car. ALWAYS watch your odometer and while you’re driving, you need to look at these ratios. Make sure you know what gear you’re in. You need to go manual transmission because sometimes you need to downshift. . .”

Somebody could really nerd out about this stuff and tell you how to maximize your fuel efficiency. If they did that, it would be hard to say that they’re wrong because they make a good point.

But it’s missing the whole point of why you have a car. The reason you have a car is not to maximize your fuel efficiency, you have a car to get you somewhere. That’s it. You don’t need to maximize the process of getting somewhere. A business is very often a means to an end. You started a business because it’s something you enjoy doing. Somebody needed help with something and you realized that you had a solution that could help people.

You charge an amount that will keep it sustainable and make everybody happy. It doesn’t have to be super, super optimized. The whole idea of maximizing your return and analyzing every square inch, it’s not wrong, but it’s missing the point of why you’re doing this thing in the first place. If you focus on that maximization too much, you might find that your enthusiasm for doing this thing has been destroyed. Then, you lose interest in doing it and you’ve really lost the whole point.

There’s a dreary, dreadful book out there called All You Need to Know About the Music Business by Donald Passman. Sorry, Donald Passman. His book has been around for 30 years now and every musician has been told to read it. He’s an entertainment lawyer that wrote this book about how to negotiate your record label contracts and the cross-collateralization clause that you’ll find in your distribution agreement and so on… Every musician was told that they must read this book if they want to be a professional musician.

I’ve seen this happen many times where I see a teenager who really loves playing the drums. They want to be the next John Bonham and they got a drum set and they practice their ass off and they love it. They love smacking the drums and they love letting out this physical aggression and keeping a rhythm.

Then, somebody says, “You’re good. You know what? You could be a professional. You really need to read this book by Donald Passman.”

But every time they read it, they keep falling asleep. “Ugh Chapter Seven: Royalty Agreements. . .”

I’ve seen some musicians completely lose all interest in being a professional musician because books like this tell them that they need to care a lot about the cross-collateralization agreement and their royalty contract.

If that stuff excites you, then it’s worth doing. If it drains you, then you need to stop doing that immediately and know that nothing is worth ruining your energy.


That speaks to me in a lot of ways.


Goals aren’t here to shape the future. Not to sound new-agey, but the future doesn’t exist. The future is the name that we call our imagination. All that really exists is the present moment and your memories of the past.

A goal is only a good goal if it makes you take action in the present. If a goal excites you and makes you do something and actually changes your present actions for the better, then it’s a good goal. If it doesn’t, if it makes you sleepy or makes you dread something, then no matter how it’s being praised, it’s not a good goal for you. Goals only exist to change your present actions for the better. That’s it.

I have to remind myself of this often. I have many different goals in my diary or in my head. I’ll often think, “That’s a great goal. I should do that.” But then it doesn’t make me take action. It was a good goal in theory, but not in practice.

Then, there are some goals that when I think of them, I actually get a shot of adrenaline.

I think, “This is worth doing! I don’t care if it’s going to make money or not. That doesn’t matter. This is worth doing because it’s giving me this reaction. This is a good goal.”


Nice. We could keep talking for hours and hours. Thank you so much for continuing to inspire me and lots of other people through your writing. Now, you also have this podcast where you post your articles in audio form, and you’ve also been posting all of your other interviews on there.


Guess what Ali? You are the last interview. In one minute, I am done with interviews. I have done something like 55 interviews in the past few months. When you asked me to do this one, it was just about the time when I was thinking of winding down.

Now, I’m saying “no” to all podcast requests for the indefinite future. This has been the concluding episode of Season Two of my podcast.

If you go to and subscribe to my podcast, you’ll hear Season One, which are these tiny little two-minute episodes of me sharing one idea per podcast. Season two are these 90-minute episodes of me being interviewed by other podcasters. And Season Three? I think I will go back to the tiny tidbits.


I look forward to it. It’s an honor to be the last on the list. I’ll certainly take a lot away in terms of writing, music, friends, life advice, skills, and all of the other stuff that we’ve been we’ve been riffing on. Thanks so much.


I love it. Thanks for having me.