Derek Sivers

Interviews → Modern Wisdom / Chris Williamson

Smart conversation. Why minimalism is considerate, how to make your website future-proof, how to stop procrastinating, achieving excellence, why truth isn’t succinct, why I’m self-publishing

Date: 2020-03

Download: mp3



Thank you very much for joining us. Since you’re a man who says no to a lot, I’m very glad that you said yes to coming on this podcast.


I really like what you’re doing with Modern Wisdom. I like your topics of conversation. So, these days, when somebody asks me to do an interview, it’s all about the quality of conversation. You sent me some really interesting topics.


Thank you. I’m really looking forward to today.

What have you been working on recently? If you were to update your /now page today, what would it say?


I have been programming. Up until Christmas, I was working maniacally on my next book, called How to Live, which I’m so fucking excited about. I was putting in 15-hour days of writing, which I think you’re not supposed to do for health reasons. But I would get out of bed at 6:00 am, and I would write and write and write. I’d stop for lunch, and I’d write until I would drop at midnight.

I was doing that for months on end, and I was so into it. But around Christmas, my assistant reminded me that some other things with my first and second books are on hold because they’re waiting for me to program some things for the translators and the store.

So, since Christmas, I stopped writing. And for 2 1/2 months, I’ve been doing nothing but programming every day. I’m programming the store where I’m going to sell the books directly from my site, programming a translation system to manage all the translations of my books, and stuff like that. I’ve been in programmer-head, which is fun.


That’s cool. I had Stephen Wolfram on the podcast a while ago. Do you know Stephen?


I met him when he was a teenager, and I was a little kid. My dad’s a particle physicist. We were living here in Abington, England. My dad told me this. I don’t remember this, but when I was five, I had dinner with Stephen. I haven’t seen him since then.


You should reach out to him. That is a man who has really optimized the ability to code as much as possible. He’s got a special laptop harness where he can go for a walk while he’s still coding, which looks like the maddest thing.

You’ve got a guy with essentially a baby stroller attached to him, but instead of it being a child, it’s some Python or some Wolfram Mathematica.


I did a five-day-long walk in the forests of New Zealand, and I had so many thoughts during that time. I enjoyed it so much, just walking, walking, walking through a gorgeous forest. It felt like, “Yeah. This is how life should be.”

If you can get away with it, a great way to live is to spend most of your time walking through a gorgeous forest.

But I have other aspirations in life. There are a lot of things I want to write, and there are things I want to read. Reading while walking – I think we’ve solved that pretty well with audiobooks. But writing while walking, I can’t do that yet. I’d like to. That could be a skill that one could practice.

It could be similar to how you decide that you’re going to start speaking Portuguese or learning to play the sitar. You would start at the very beginning and understand that you are not expected to know how to do this thing today.

Writing through voice and recording your voice instead of writing visually on a typewriter would be a very different skill to learn. It seems like it would be very useful.

Between voice recording and voice recognition dictation software, I think we have the tools to make it viable to have your main method of writing be oral. It’s very appealing.


How much of it is the being outside, and how much of it is the movement? Because you could quite easily get a treadmill desk.


That’s just sad.


You’ve got to have the landscape going by. Right?


Yeah. It’s the combination. If it was just the outside factor, you could say, “Okay. Set up your laptop on a picnic bench outside.”

It’s the walking outside through a forest. I tried a treadmill once in my life, and it felt like the saddest thing. We use them as a negative metaphor, don’t we?

”How’s work?”

”Ugh, it’s just another treadmill.”


It’s badly branded. They should rebrand it. They should call themselves something else, shouldn’t they?

Am I right in thinking that How to Live is a descendent of the Directives that you wrote?




So, that’s the love child of the Directives?


Yes. If you have read Sum by David Eagleman, it’s an homage to that book. Sum is probably my single favorite book. There’s a page on my website where I collect my notes from every book I’ve read since 2007. It’s at There are notes on 300+ books there.

I take detailed notes whenever I’m reading something. Sum is the #1 book at the top of that list. I wish everybody would read that book. It’s one of the most brilliant, creative, think-piece books. It’s 40 little short stories, each just two to three pages long. Each one answers the question, “what happens when you die?”

It’s a constant reimagining. It’s 40 different answers to that one question. I love that format so much.

Chapter 3 says: When you die, you awaken in the great hall, and it’s empty. You find out that God is a creator. He’s not a manager. He tipped over the first domino a billion years ago, and he’s on to other things. He doesn’t even know we exist.

Chapter 6: When you die, you find out that what you knew as your life was just an artificial intelligence program. You are an artificial intelligence program.

I like this idea of 40 answers to one question. Each answer deliberately disagrees with the previous chapter because it’s a reimagining of a different answer. My book, How to Live, is an homage to Sum. It’s using that exact same format to answer the question, How to Live.


It seems like your approach to writing, content, and production is lean. There’s very little fluff. The Directives that you came up with are a list of 120 instructions.

Is removing the fluff something you’ve always done?


I’m living in Oxford now. When people visit my house, the first question is, “Do you live here?” Because it’s very empty. I’m say, “Yeah. To me, I feel quite settled. Look, I have a couch. That’s big for me.”

Minimalism goes through all aspects of my life.

When it comes to writing, it’s just considerate. The more you say, the less people hear. The more they tune out. If you tell somebody, “Check out this article,” they click the link, they see the article, and they say, “Oof, okay. This is 50 paragraphs. This is going to take me half an hour to read.” They may skim it quickly.

On the other hand, if they click and it’s only 18 sentences, then hopefully, they’re going to read all 18 sentences. I found out that the average length of one of the articles on my site, and the chapters in my book, is 22 sentences.

I chisel them down. I get rid of every single word or sentence that isn’t absolutely necessary.

I spent 15 formative years of my life as a songwriter. From the ages of 14 to 29, my primary goal in life was to be a great songwriter.

I wrote over 100 songs. That’s 15 years of my life that I tried to say what I want to say in six syllables to match the melody. Maybe that’s why I do it. I think I still take that approach to my writing.


I’ve been thinking about a lot lately about the crossroad opportunities in life.

We have these grooves that we’ve greased, and often there comes a time where we have to decide to continue to grease that groove or take ourselves out of that.

Often, like a river, we take the path of least resistance. But to change the flow of that river, there’s a lot of inertia and stagnation to get over to the other side.

What are your thoughts about that?


During those times in life when we’re making decisions, we forget to explicitly name the benefit of doing nothing, of continuing as we are now. Too many people say, “I have to make a choice between A and B. But they forget that there’s option C, which is to do nothing, and carry on as you are now.

I don’t mean just consider it. Actually state it and say it out loud. Name it as an option. The usual thing people say is, “Should I do this new thing? What are the benefits? What are the drawbacks?

You should also ask, “What are the benefits of not doing this new thing? What are the benefits of doing nothing?”

I heard this idea in a book called The Courage to be Disliked, which is also brilliant. It’s one of the best things I’ve ever read.

It gets you to consider why you’re not changing. Why are you just continuing on the way you are? There is a benefit if you keep doing what you’re doing.

If you ask yourself, “Why am I carrying on as usual?” You might come up with an answer like, “Well, my life is pretty good now. I’m happy.”

Or there’s a chance that doing this new thing would make my life harder, and I don’t want to risk that.

You can name the mental mindset ones like, “My life feels under control right now, and I like feeling in control. I like feeling like an expert. I like feeling smart. If I do this new thing, I’m going to feel dumb and out of control, like trying to write a book while walking through the forest.”

Once you bring these to the surface, they don’t just sit in your subconscious. You’ve brought them to the table. You can weigh them in your decision. You’ve laid them out as an alternate option. Then you have to admit that it’s okay to do nothing. I think often we feel that we’re always supposed to be doing something.

Warren Buffett is quite public, but he has a quiet partner, Charlie Munger, who is an interesting thinker. Charlie Munger gave this interesting advice to young investors during one of the many times that someone asked, “How can we be successful investors?”

He said, “Imagine you’ve got one of those little loyalty punch cards with 10 holes in it that you can punch out. That is the total number of investments you’re allowed to make in your life. That’s it. If that’s the case, you’d be better off waiting and waiting for years for the right thing to come by. Then, when the right thing comes along, you knock it out of the park. You dive in all the way when you see the right opportunity,”

That’s what my book, Hell Yeah or No, is about.


I’d like to talk about your approach to decision-making. I think you’ve said that you’re a slow thinker. In the same way that your articles are lean, your decision-making is considered.

Is that because of Charlie’s approach? If you make the right decision, you only need to get a couple of them very, very right?


There’s a theme that I think is going to come up a few times in this conversation, which is there’s no right or wrong approach. All of these things and these philosophies are tools that we use for specific situations.

I have an article called, “Hell Yeah or No,” that a lot of people quote. Some will email and say, “This is great. I’m using it for everything in my life now.”

I say, “No. No. No. ‘Hell Yeah or No’ is one specific tool for one specific situation – when you’re overwhelmed with options and you’re in danger of drowning. Then you raise the bar all the way. You say no to almost everything and say yes to almost nothing. But it’s for a specific situation

If, for example, you’re straight out of college, you’re about to jump out into the world and try to make something of yourself. Then, it’s probably a better strategy to say yes to everything. Just do it all. Sleep less. Say yes to everything. Try everything. Go everywhere. Meet everyone. Do 20 different jobs per year, a few weeks each, and just do it all.

Then, when something hits, when the world starts rewarding you in a certain aspect, you can double down on that. When you start to get successful in that one thing, and everybody wants a piece of you, then maybe it’s time to say no to almost everything and stay focused on the one thing that has given you major payoffs.

And when you asked my slow thinking that felt like a cathartic admission.


Also, probably a little bit of a disclaimer.


Yes. Thank you. Good word. It was a bit of a disclaimer. Partly because I meet strangers that ask me deep questions, and they go, “Oh! Derek Sivers! I want to ask you something.”

They ask me a question, and I say, “Uh. I don’t know.” They look at me a little disappointed.


I thought you were Derek Sivers! [Laughter].


”You’re supposed to have the answer.” I saw, “Well, in a few days, I will.”

I just noticed that I’m not the quickest to draw, but that’s okay. I spent a little time thinking that through and realized I don’t need to be quick, and in fact, I think it’s really kind of cool. When you try to be quick, you give this knee-jerk reaction off the top of your head.

You say the first thing that comes to mind. I’ve found that the first thing that comes to mind isn’t as interesting as the things that come to mind much later, whether it’s five minutes or five days later.

Once you work through the usual reaction and get to the other side of that, that’s the stuff I want to dive into. I’ve embraced my slow approach.


We all want to appear competent and capable. I fall into that trap. I’m constantly trying to strip away the very sticky element of the persona of a competent, regular podcaster. When people ask me things, I’ll say something like, “Well, I had this conversation with Aubrey Marcus. It’s very interesting in Episode 117 when he said that.”

Then I think, “No. No. No, Chris. Just allow yourself to sit with the question. Don’t try and broadcast this version of you.”

I’m not convinced that that’s where my value lies.

It seems like that you’ve identified that you add more value by waiting and considering and coming back with your answer later instead of saying something quickly to close the loop in order to look cool, capable, and competent.


Right. But it isn’t just about looks. In my case, I am pursuing the path of being a great writer and thinker.

I’m not pursuing the path of being a great interviewer or debater. If I wanted to be a great interviewer or debater, then I would change my value system accordingly.

I would say, “Well, I used to be a slow thinker, and that’s my default, but I need to practice being a quick thinker now because I want to be a great debater or interviewer. I need to be quick. That’s just how that game goes.


The Ben Shapiro approach. Yeah.


Right. The slow thinking is for me in my current situation.


What would you identify as your life values?


[Laughter] That’s a big one.


It’s one that I’ve been pondering a lot recently. Why don’t I tell you mine?


Okay, please. Thank you.


Cool. I refined mine down to five. You’re supposed to have no more than five, or else I’d have to pay tax on the ones over the top [laughter].

My values spelled out an acronym, CASES.

Curiosity: To be curious, to learn new things about myself and the world around me.

Adventure: To experience new things and meet and see new people.

Self-less development: A word that I made up, which is to learn about myself, improve, and then teach others what I’ve learned.

Excellence: To be precise with my thoughts, words, and actions. I want to fulfill my potential. I want to make the most of minutes.

Self-care: If I don’t look after myself, I can’t do the things that I want to do for myself and others.

If I broadly ensure that most of the stuff that I do on a daily basis meets most of those values – at least one – I’m probably in the right ballpark.


Wow. Very cool.

I like that. I think my big ones are more concept-based. To me, one of the biggest ones it to ignore what you say but notice what you do. I think about this one a lot. Your actions reveal your values. It doesn’t matter what you say.

You can say that you think it’s important to be kind to everybody, but if you go around being an asshole, that’s clearly not one of your values. We do too much thinking about what we want in theory and too little noticing about what we want in practice.

We can say we can think that we want something, but you have to go out into the world and try things. If you have a theory about what you want, go try it as soon as possible to find out if you really want that and be very open to the fact that your theory might have been wrong.

Don’t be upset about that. Just say, “Oh. Okay. Well, sitting at home in my bedroom with my notebook, I thought I wanted this thing. But now that I’m actually doing it, I found out I don’t, and that’s okay.”

Another value: I think we oversimplify.

For example, you may think, “I’m sick of the city. I want to live in the country.” So, you move to the country. But after a few months, you miss the city. I have a lot of friends in New York City that did this.

I think the truth is more nuanced, which is that sometimes, you prefer the city, and sometimes, you prefer the country. But that nuanced truth is less dramatic. It’s less simple. So, it’s harder to tweet your stance on that.

We want to have a very simple version of our self-identity so that we can fit it into our little social profile and say who we are quickly.

So, I think we often oversimplify. Often, things are situational. You may want one thing when you’re in a certain situation, but not when you’re in another.

I mentioned that “Hell Yeah or No” is an idea for a certain situation. But the problem is, we feel a need to decide which it is. Do I value this thing or not?

Don’t oversimplify. Acknowledge nuance and acknowledge conditional situations.

My friends are spread out around the world, so most of our conversations are by phone. When friends have these life situations, they’re often trying to decide, “Am I going to do this thing or that thing?” Or “Do I prefer this or that?”

I feel it’s my job to remind them to remind them that the answer might be both.

I like this idea that in-between black and white is not only grey but every color in the world. I think you can choose to be colorful in your values, and like colors in nature, you can acknowledge that you’re ever-changing.

I’ve gone through some very distinct phases in my life where I’ve made a life decision to be in the middle of everything. “I’m going to move to Singapore. I’m going to be in the middle of Asia. I’m going to meet everybody and do everything.”

I did that for a few years. Then I had a kid. After that, I thought, “ I have a baby now. I want to move to the middle of nowhere in New Zealand. I want to raise my kid in nature and give the finger to the world.”

So, I said, “Goodbye world. I’m going to raise a kid for seven years.” I disappeared off to New Zealand for seven years and had that phase.

This past year, I moved to England. It was a new phase for me to explore more.

You can acknowledge that what you wanted five years ago is not what you want now. Just because you said it in the past doesn’t mean that you still need to honor it.

There’s this question that I’ve heard often. What would your teenage-self think of you now?

The funny thing is that I think that question implies some kind of authenticity as if your teenage-self was your real authentic self.


An unencumbered, pure version of your spirit. That wasn’t affected by all of the crap that you’ve done over the last 20 years. Yeah, I get it.


Right. I think that no, no, no, no. In fact, I think it would be pretty sad if I was living some kind of life to please my teenage self. That would acknowledge that I haven’t changed. But man! I’ve changed a lot. I’ve changed so much. The me now is very different from the me from 10 years ago, and very, very different from the me from 30 years ago. And I love that.


At 17, some bits of me were good, but I was a total dick in other ways. This loops back to the crossroad opportunities in life. We have this momentum, which we’ve built up. We’re moving in a direction like a river cutting through rock.

There’s a continuity bias. I am a musician, writer, podcaster, club promoter, DJ, whatever. I am that thing, and there’s this requirement, this feeling like, “The new thing. I didn’t do well on the new thing. If I change, then I’m not that thing anymore.” That is me. That was me.

That’s where I got my quantifiable metrics of status and success from the people around me. This is what society is. Put me on a pedestal. I’ve had some form of success with this. If I do this new thing, what if it all goes to pot?

It doesn’t surprise me that all of us sometimes find it challenging to let go of the tether to that balloon.


Let’s think about that question you asked about what we are optimizing our life for. About the difference between existing with an understanding of your values, your goals, and your plan versus just allowing life to blow your leaf around. Like the beginning of Forrest Gump. The little leaf blowing in the wind.

There can be reasons at stages in your life to make yourself stick with one thing, even if you want to change every distraction. Then there are times where it’s right for you to go chase distractions.

I think about this wonderful rule of thumb of asking yourself what you want now versus what you want most? I love the simplicity of that sentence.


That’s a tough question to answer. [Laughter]


I think of shallow-happy versus deep-happy. Shallow-happy is just having the ice cream. Deep-happy is being proud of yourself for not having the ice cream. But most importantly, it comes back to whatever works for you.

There is no philosophy or approach to life that is inherently right or wrong. You just have to try it and see if it works for you or not.

I don’t mind holding some beliefs that are completely false if that works for me right now and gets the desired action. You have to ask yourself, what does “works for you” mean? What makes you act? What makes you take the right actions?

Maybe for you at this stage in your life, the right action is to stay focused. Or maybe the right action for you at this stage in your life is to open your mind to new inputs, try new things, and indulge every curiosity. Only you know what stage of life you’re in.

Do you need to keep focusing right now for your current desires in life, or is it time for you to stop doing the thing you’ve been doing?

No podcast is going to tell you the right answer. But I think what these conversations, podcasts, articles and books, or whatever inputs we get in the world are useful because we hear other people’s thoughts.

It’s useful to help you consider another way of being. But ultimately, you need to try it on and see if it works for you in practice and not just in theory.


It’s interesting as I produce more content on this podcast, I feel myself thinking about the prescriptive model of life. There are Life Hacks Series. By no means is that something to live your life by.

I see that side. I see the prescriptive side – the best sleeping posture, how you can scale your business using Google AdWords and blah, blah. I see that side, but the nuance is where all of my interest is.

I think you arrived at a solution, which is perfectly curated for you because we are all world experts in ourselves.

You’re a world expert in Derek Sivers, and I’m a world expert in Chris Williamson. Really, there isn’t anyone who is as qualified to make a decision about what you should do than you.


Yeah. Taking in the input of others. Hear it all. Take it all in. But ultimately, only you know what’s best.


Yes. I want to bring up mortality and playing the game of life. Our existence is fleeting. Very few people will remember that we were here or care when we’re gone.

How does this impact the way that we should view our lives and our occurrences within them?


I’m curious to ask why you’re asking? I never understood people’s need for meaning. I tend to go from desire to desire, from interest to interest, from project to project. I’m always, always, always working toward something. So that is my meaning in life at any given moment.

If I zoom out, and if you were to say, “No, Derek. What’s the big picture?” Then there’s a project or a path there too. I can say, “Oh. Well, in the bigger picture, I want to find interesting thoughts that others haven’t considered and share those with the world.”

You could say, “Okay. Well, what’s the bigger picture of that?”

”Well, honestly, it tickles my brain and is viscerally pleasurable to find a new way of looking at things. It’s creative and inventive and fun.”

You could say, “Yes, but what’s the real point of that?”

It keeps going, and you could say, “I’m growing. I feel that I’m constantly growing and changing. I’m learning more about the world. I’m understanding the world better, which makes me happy on a day-to-day basis. The world becomes my playground.”

At any point, you could zoom in and say, “Why are you doing this thing? This minute? This hour?” Or zoom out and say, “Why are you doing this thing this decade?”

It always has a purpose. So, I don’t really understand this question of about the meaning of life. I don’t care.

It’s like the Tibetan monks who make those elaborate sand drawings, and then they get destroyed so easily.

Which is fine. There have been projects that I’ve worked on for years, and then just a month or two before launching, I went, “Eh,” and chucked it.

It’s fine because I was enjoying it the whole way. It wasn’t a goal that didn’t launch. It won’t mean anything in 50 years. Well, so what?

Let me turn it back on you. What is your thought behind asking that question?


It’s twofold. The first one is many people don’t get to do what they want to do in life, and by asking what is the meaning of life – how can I find meaning and purpose in my daily, yearly, decade existence – they’re hoping that someone will prescribe them the steps to get away from doing the things they don’t want to do and move toward doing the things they do.

The second thing is a big part of it is a repackaging of the fear of death. I think humans don’t like the idea of dying. Unless you’ve absolutely taken the red pill on stoic philosophy, free will, or whatever it might be, there is an innate fear in dying.

Previously, we might have had that serviced by religion. Previously, we may have had that serviced by a belief in an afterlife or a higher power or whatever it might be. Now, as we have an increasingly secular society, I think people are trying to find a meaning in their existence right now, which is so great that it justifies the fact that one day it’s all going to end.

How’s that for an answer?


Thank you. That helps.


I think that might be it. I genuinely do. I did a podcast a couple of years ago with a guy who was talking about how he thought people’s search for happiness is proliferation of how to be happy – five steps for your fulfilled life.

He was adamant that it was just people fearing death and trying to run away from it. Upon reflection, I can see more and more of that now.


This conversation is going to be recorded and kept around. I definitely think of all this stuff in terms of after death. I think of all of the stuff that I’ve written as the legacy I’m leaving.

Did you read Derren Brown’s book called Happy?


I did. I actually got to see him speak about it a couple of weeks ago in London.. It was great.


Oh wow. I wish I had known about that. I’m a massive fan of his.

Whenever people ask that question about inviting any person ever in history, living or dead, to a dinner party, it’s Derren Brown. That’s it.


He’s a beast.


No need for Jesus, Buddha, or Gandhi – just Derren Brown [laughter].

Near the end of his book, he had a wonderful tiny point in passing. He said that your thought patterns are your personality. The way you think is your personality. When you share your thoughts and personality with your loved ones or to the public, they carry on after you die. Therefore, that is the afterlife. Your personality carries on after your death.

It’s always funny to me when, say George Harrison from the Beatles died, or Ray Charles, people, “Ohh. That’s so sad.”

Or David Bowie. I think, “Really, were you waiting for David Bowie’s next album? Have you bought all of his albums in the last 20 years?” They go, “Oh, no.”

Then I think, “Then, he’s not dead to you. You’re enjoying what he did in 1972, so you can carry on enjoying that. David Bowie is not dead for you. David Bowie is very much alive.”

You weren’t a dear friend of theirs. They weren’t stopping over at your house the next week for dinner, so what they put out there in the world is completely alive for you. That is the only version of them that you get. So, I think of this creative output as quite eternal, at least lasting for another couple of generations.

At the very beginning of the call, you mentioned my hyper-simple website. Part of that is because I’m expecting this website to go on 100 years. Who knows what holographic device is beamed into people’s retinas or implanted in their brains or how that website will be used in the year 2300, but I expect that my site will be around then.

I think people using WordPress and current plugins filled with Google analytics and JavaScript are being very, very short-sighted.

If I were to die tomorrow, this site is going to keep working for a couple of hundred years because it is just plain HTML and text with absolutely no contemporary tooling that will expire. That’s very much on purpose.

I make my site by hand. I don’t use any frameworks. I don’t use any software. I type every HTML line in by hand.

You said something like, “Removing everything or striping it down.”

But actually, it’s the opposite. Since I open up a blank text document to create a webpage, why would I take hours of time to type loads of unnecessary div tags and JavaScript includes() unless it was absolutely necessary? That’s too much typing. It’s unnecessary.

So, no. I don’t put in anything that isn’t needed. A lot of that is because I’m making a site that’s intended to be around for at least 100 years.


That’s hardcore. I really, really like that. I was going to ask what code your site was written in. I thought I had seen something to do with Raspberry or . . .


No. You’re thinking of Ruby. I do use the Ruby programming language for a little bit of automation, but it just helps me output static, plain HTML pages with nothing in it.


When you originally do your book summary, is it plain text, like in a Notepad file?


Yeah. I still do.


Or something like the most hardcore text version that you’re going to get so no matter what happens in the future, it’s always going to be future-proofed?


Basically, I only use two programs on the computer. I use Vim, which is a raw programmer’s plain text editor, which is like Notepad. It doesn’t do bold print or anything like that. It does no fonts. It’s just plain text. It’s eternal.

Civilizations on Saturn’s moons will be able to read plain text files. I don’t think they’ll be able to run WordPress 7.2 necessarily. But plain text files, yes.

Then, I use Firefox, and that’s it. I do everything, all day long, in Vim, a plain text editor. I don’t use the Cloud for anything. I do nothing online. I don’t use Google Docs.

In fact, I prefer working offline. A funny little nerd habit of mine is, about two hours before I go to sleep, I completely power down my broadband modem.

I go over to the wall, and I click off our British power switch on the wall. It shuts off the internet. I hold down both buttons on the phone, so it powers off completely.

Now, I’m in a dark house with no connection to the world, and that’s how I spend the last two hours of every day. I may continue writing, but it’s completely offline.

I do the same thing when I wake up in the morning. I spend the first four or five hours of the day completely offline. I don’t turn on the internet usually until noon or so when I’ve gotten in a few good hours of writing and working and programming.


Is it just to give you time to focus, or is there something more symbolic about that? Do you like being off-grid in that sort of a way?



I find there’s a wonderful peace and relief when I know that there’s no way to contact me. My phone is off. The internet is off. I like the fact that if there was a real emergency, somebody would come bang on my door. But I like being unreachable.

It’s a different feeling when you’re sitting there focusing on work but a little part of your brain knows that there are alerts happening. At any point, you can just grab your phone and hit red or whatever your fix is. I like just not being able to.

I’m the kind of guy who doesn’t keep cookies in the house. I can’t have a box of cookies and then just not eat them, so it’s better for me not to have the cookies in the house.

It’s better for me to completely shut off the internet, so my brain goes, “Ah. That’s not an option.” I really like that.


One of the best lifestyle changes I’ve made over the last few years has been charging my phone outside of my bedroom.


Yeah. No electronics allowed in the bedroom. It’s so unsexy.


It is unsexy, and as soon as I did it, I started sleeping better.


I literally ban electronics from the bedroom. There is a little clock by the bed. Just a clock. It’s one of those little 5 £ clocks that does nothing but show you the time. That’s it. No phones allowed in the bedroom.


Is it firelight? Is it just candles like an old man with a lamp wandering around?


I wish. That would be great. I do have a candle in the bedroom.

What’s kind of cool is that my kid is now eight. He’s been raised this way, so he’s not an iPad addict like a lot of kids his age. He actually scoffs at video games. He had a friend two years ago, a next-door neighbor, who was one of his best friends ever.

This kid’s dad was always in the basement playing Fortnight or something for hours. He was a completely absent dad. He was not there for the kid. He was grumpy because all he wanted to do was play video games, and he would never play with his kids.

It was so interesting that my son saw that. He didn’t just note it but mentioned how sad it was to me a few different times.

One time, we were playing a little word game of opposites. What’s the opposite of music? What’s the opposite of a cloud?


What is the opposite of music?


You want to know my favorite answer?


Yeah, sure.


First, take a guess. What do you think is the opposite of music?




No, because silence is part of music. It’s an important part. What else could it be?




My favorite answer: the opposite of music is business.


[Laughter] Yeah, okay.


See, these are the more fun answers. Right? That was a fun example of you have your first and second thoughts. That’s like the slow thinking.

In this word game we kept playing, the opposite of music is business. That’s an idea that didn’t come until a week after trying to answer the question. That was my favorite answer. It’s like, “Ohhh, that’s good.

My son asked me, “What is the opposite of being a dad?”


You didn’t say being a mum, did you?


No. His answer was a winner. It was playing video games.




Yeah, because he had such a negative association with watching his friend’s dad playing video games instead of being there with his kid. The point is, we have a household that is very offline. Let me take that back. Not very offline; it’s part-time offline, and I really like that.

It’s not the primary thing. There’s no TV in the house.


That’s a self-aware kid that you’ve got there, Derek. He sounds really, really cool. I like him.

I want to touch on excellence for a minute. I mentioned that it is one of my core values.

How do you balance between wanting to produce your best work – something that you’re proud of, that connects with other people, a high representation of your cumulative skills and talents – while also giving yourself a break?


Let’s look at the micro example of procrastination. If you look at why people procrastinate, it’s usually when you’re facing something difficult. It’s easier to retreat into the safe thing like surfing the web or playing video games instead of uncomfortably facing what needs to be done.

The way to stop procrastination is to catch yourself doing it, to deliberately interrupt it, and then go back to doing what you know you need to do no matter how unpleasant it is. I think it always gets easier after you begin.

When I think of excellence, I think of a life-size version of that. If there’s something you’ve always wanted to do, you need to stop wasting time and do it. If you write out your bucket list, the things you want to do before you die, I bet you could do almost all of them in a few months and most of them in just a few weeks.

Usually people’s bucket lists are the places they want to visit and some things they want to do. I think if you took a couple of months off work, you could do 2/3rds of that list right now and be done by next month.

It’s a matter of doing them instead of doing other things like watching shows, surfing the web, playing video games, sitting on couches hanging out, tasting the local beer.

What’s the opposite of excellence? That’s procrastination.

People who choose the easy path in life don’t ever achieve excellence at anything.

Excellence is usually choosing the more difficult path, which gives the greater rewards. It’s doing what you know you need to do, even if you don’t feel like it. My definition of excellence is tainted by the fact that I was in music for 20 formative years of my life.

So, I think in terms of being an excellent performer, being an excellent writer, being an excellent producer. You might have a different definition of being an excellent gentleman or something like that.

Somebody listening to this could have a different definition where maybe excellence to them is excellence in their composure. Maybe it isn’t something you need to practice for 20 years. Maybe it can just be in the moment.

You can decide right now, today, from this moment on to be excellent, and you can achieve that by not giving in to your temper, stopping drinking, or whatever it may be.


I think precision is the word that I like to associate with excellence.


Why precision?


Because precision for me is doing the thing that you said you were going to do or doing the thing that you mean to do. Not doing another thing. That’s one of the reasons why I like you as a speaker, why I like Ben Shapiro and Sam Harris because the speech is very precise. The number of words that are used are the number of words that are needed.

I’ll link back to what you said earlier about the way that people make choices and the kind of life they have. Does that mean easy choices, hard life or hard choices, easy life?




I read a really interesting article from Taylor Pearson on procrastination. One of the things that he came up with was, “Procrastination exists because people have a fear of failure. They’re concerned that they may be not good enough, or that they don’t have the skills that are required.”

I think that an element that he didn’t touch on in this is that it’s difficult. I have to do the hard things and there’s something easier floating around: the cookie jar, the social media fix.

He has this beautiful quote where he says, “Interestingly, sometimes, we procrastinate to ensure that we inoculate ourselves from public failure, but the interesting thing is, by procrastinating, we do inoculate ourselves from public failure by assuring ourselves of private failure.” I love that. I love the reframing of that.

It’s like if you do not do this thing, it doesn’t matter whether you think you would or would not fail because you’re guaranteeing the fact that you will, by not starting it. I thought that was a powerful model. It was an interesting way to loop it back around.

What have you changed your mind about recently?


A lot of the things that I said were core values are actually new to me. Maybe that’s why they came to mind first when you asked they’re newest to my brain. The stuff that’s been in my value system for 30 years, I take for granted. I probably don’t even know it’s there anymore.

Even though I write succinctly because I think it’s considerate, I don’t think truth is succinct. I think truth is very nuanced. Memorable sound bites are succinct. Quips and aphorisms are succinct. succinctness is good, too, to carry ideas.

What do you call it in nature when those seeds have little barbs on them?


Like dandelions?


Yeah, thank you. Dandelions or burrs. Succinctness is a good tool to help ideas spread and carry, but succinctness is almost the opposite of truth. You can make catchy slogans that make people go, “Ohh, wow, that’s good.” But it’s one little ingredient in the truth. The truth of things is often very nuanced.

In these situations, if you’re in that stage in your life, for the kind of person you are, the kind of things you want, then THIS is true. But on another day or in the morning or last year or if you were a little bit of a different person, or for your sister that is NOT true. In fact, if you were to quit your job tomorrow, then suddenly that would no longer be true, and et cetera.

But that doesn’t tweet well.

This is pretty new for me. The constant acknowledgment of the nuances to get to the truth.

I have a dear friend who’s been with the same guy for years, but she’s always complaining about him, often calling me with, “What should I do? Should I leave him? Should I stay?”

Finally, I thought with this new focus on nuance, that she’s actually happy with one foot out the door. We don’t need to oversimplify it into an either-or – should I stay, or should I go now.

The truth is, she’s happiest with this one-foot-out-the-door feeling, and she doesn’t need to oversimplify that into in or out. This example came up yesterday, so it’s the one on my mind.


I like it.

While I was podcasting with George MacGill last year, we did an episode on mental models – the highest played ever Modern Wisdom episode. He talked about the Barbell Strategy, which is when you don’t just have black or white thinking, you have black and white thinking.

You push yourself to the ends. You’re able to do incredible deep work, but then also be very social when you need to turn that on. You are able to use the succinct side of things, but you’re also able to understand the nuance as well, on the complete opposite end of the scale.

There’s another point on that that I have to bring up, which is I love aphorisms, and I think that guys like Naval, who are able to distill down incredible wisdom into 160 characters, have a skill that I absolutely do not have and wildly envy. I think you’re right. I think you are correct there. The nuance and the understanding of all that, I think it all ties together.

Final question.

Can we give the people who are listening any idea when they can expect your new pieces of work from you?


There are three. I finished my next book two years ago. I finished my second one year ago, and I’m finishing my third book now. But the thing is, I nerded out on self-publishing.

My first book, Anything You Want, was first published by Seth Godin, but then he sold his publishing in print to Penguin, a major publishing company. Penguin re-released it. I didn’t actually like that experience.




I didn’t like that I didn’t fully own the rights to my own book.

Here’s one core example. There were two or three different times when I got contacted by people who were putting on a conference. They wanted to buy 750 copies for all of their attendees.

I said, “Great. That’s amazing. I would love to do that.”

They said, “Okay. How can we do that? Can we get a quantity discount for 750 copies?”

I have to go ask Penguin. “Hey, Penguin. How can we do that?”

They went, “You have to tell them to buy it at Amazon. You can’t order it from us. We’re not a retailer.”

I said, “Oh, man. That sucks. I want this person to have 750 copies. A dollar each would be fine. How cool that they’re going to give it away.”

But I had to tell this guy, “Just go to Amazon and type 750 in the quantity.”

I want to be able to do the right thing, but I don’t even own the rights. Penguin has the rights. I wrote that book for Seth Godin, and then that’s what happened.

Even though my rep with Penguin loves me, and she’s wonderful and great, I just didn’t like the experience. I don’t need the ego gratification of being with a major publisher, so I decided to self-publish to keep control, which reminds me of way back when I started CD Baby.

In the mid-90s, the internet was just getting started. There was a cool, do-it-yourself pseudo-punky ethic about sticking it to the man. Fuck the major record labels. I’m going to do this myself. I’m not signing away my rights to some label.

But here we are 20-something years later, and everybody is selling their soul to Amazon. You mentioned earlier about how to do the Google AdWords thing to increase your business.

It’s like everything’s trying to please the man. The man is now Facebook, Google, Amazon, Instagram, whatever. It reminds me of the pre-internet thing where everybody was selling their soul to the major record labels in hopes of getting rich.

I appreciated that kind of giving all the finger kind of spirit, knowing that you’re probably going to sell less by choosing to be independent, but fuck yeah, it felt so much better.

The point is, I nerded out on not just self-publishing, but self-printing, self-layout. You know how I told you I do everything in my plain-text editor called Vim?




Do you think I did the book design layout in Adobe InDesign? No. Fuck Adobe. I did it in plain text, and I found some software called LaTeX, which you can use to do book design as a programmer in plain text. I’m fucking hardcore on that.

I’m building my own store on my own site because fuck Amazon. I don’t want to sell my book on Amazon. At least not at first. I will eventually.


That’s so cool.


I understand that I’m choosing to sell less by doing this, but damn it feels better. It’s so much more fun.


Well, each book is worth 100 of what the one would have been before because you crafted the thing out with ancient technology in a programming language that no one has seen since the 1800s. Yeah, exactly.


It’s funny. We talk about rationality. Well, you and I didn’t, but people talk about rationality. You could say that this is a rationally-unwise choice, but emotions matter. The way that something feels is a big reason why we do anything. In fact, if you want to get meta, meta, meta, the reason the people like to be rational is because it feels better.

Sorry. I was answering your question about when are these books coming out?

Any day now.


We understand why they’re not here yet.


Yes. It’s because I’ve nerded out on the self-publishing and the self-printing. Lastly, I decided to print hardcover books for an emotional reason. It made me a better writer knowing that I was going to print hardcover books.

It’s because knowing that I’ll be printing hardcover books, even though I’m a total tree hugger, means I don’t want to waste a single sheet of paper ever. If I’m going to be cutting down trees, really every sentence has to be worth cutting down a tree now.


You upped the stakes of the writing because the analyzed costs were increased. That’s interesting.


It’s all just about done. Actually, this morning, I was programming the store on my site.

By doing it all myself, I get to do some fun nerdy things like custom dedications and things that people who sell their books on Amazon can’t do. Everybody who orders the book from me can ask it to be custom-dedicated to them, and the server will create a custom-dedicated book for you.


That is cool.


I’m going to see if I can do that with the audiobook, too, so that everybody who buys the audiobook gets a custom message like, “Hey, Chris. It’s Derek. This book’s for you.”


No way.


Fuck Amazon. They can’t do that.

Ooh! Anybody who wants my stuff, I actually enjoy taking a few minutes a day to answer all my emails. I really like hearing what strangers around the world are doing. I like it when people introduce themselves and say, “I’m a guitar technician in Arizona or I’m a dentist in Estonia.”

Feel free to email me and ask me a question. If you go to, my email address is out there in public. You can email me and ask me anything, and I always reply.


Cool. That’s certainly cooler than just saying, “I’ll head to my Twitter.”


[Laughter] Twitter is still a corporate middleman. I’m thankful that I got online in 1994 because I went through that first dotcom boom and crash.

Every musician was 100% dependent on their MySpace page to manage all of their fan list, music, releases, announcements, and gigs. Then, MySpace disappeared.

I think I have a healthy distrust of any corporate middleman. I think they’re always about to go belly-up any day. I would never tell people that Twitter was the way to reach me because I don’t trust that they’ll be around tomorrow.


I think that if you have plain-text files as the future-proofed version of writing things down, email lists might be the most-likely-to-survive-a -nuclear-apocalypse contact list.


Exactly. It’s an open standard. It’s uncommercial. I like those uncommercial media forms. Paper books have no advertisements in them. Amazon’s not tracking what you highlight in a paper book. I love that kind of stuff. Nerd, nerd, nerd.

We were saying goodbye. I shouldn’t keep taking tangents.


Derek, man, it’s been such a pleasure. Go to Derek’s website and hassle him via email and not his Twitter because fuck Twitter.

Derek, man. Thank you so much for your time. I really appreciate it.


Thanks, Chris. It was a fun conversation.