S1 Bonus - Derek Sivers on the Pursuit of Meaningful Work

Leo

Welcome to the Zen Habits podcast, where we dive into how to work with uncertainty, resistance, and fear around our meaningful work. This is for anyone who wants to create an impact in the world and cares deeply enough to do the work. I'm your host, Leo Babauta, creator of the Zen Habits blog.

My guest on this episode is a friend, Derek Sivers. He is someone who I have followed online. We've interacted over the years and he's inspired me for so long.

Derek Sivers, how do I put him in a nutshell? He's a, an entrepreneur. He's a musician. In the nineties, I think late nineties, he started a company called CD Baby, which was really for musicians and, and helping their business. Then, another related business called Host Baby and then sold both of those in 2008. Moved to Singapore and then New Zealand. So he's lived a fascinating life.

I think he's done so many interesting things throughout his life, and he's also someone who writes really incredible blog posts and book notes. So he'll go through a book and then take notes as he reads the book and then put all the notes on there.

I remember when my first book came out called "The Power of Less", he published a book note on that. And I went and read it and I was like, 'eh', he gave it like basically a middling review. So Derek is very honest with it, and actually I really respect his his book reviews.

He's also written a number of books, including one he released in 2021 called "How to Live", and I actually think it's a really great book. He said it's 'my masterpiece, the best thing I've ever made my soul in a book, and a bunch of other really good things as well.

Now he's writing a book that he's published a number of chapters on that called "Useful, Not True". And I actually think it's a really great book of things that we don't have to take as absolute truth, but they're still useful in some way. He's writing it right now. He's been releasing some of this stuff and you can get on his email list to be the first to get updates on that.

So "Useful, Not True". Derek Sivers, really authentic guy who I really love. Let's have him on.

Leo
All right. Well, welcome. Derek, thank you for being on the podcast. I'm so excited and honored to have you. But I just wanted to say thank you for coming.

Derek
Thanks, Leo. And hey, audience in case you didn't say it in the intro, Leo and I have been communicating and aware of each other for 15 years, but this is basically our first time actually speaking live for real. So exciting, excited to finally talk.

Leo
Yeah. You're someone whose work I've resonated with for so long. I even started my 'now page' based on something that you created, which I was really cool, but I found a lot of inspiration, including your like short URLs on your website. I've been reading your stuff forever, and I'm actually a little bit of fan, fan-ness coming up in me, just like, oh, excited to be talking with Derek Sivers.

Derek
Well, same here, I'm not trying to one-up you, but dude, I'm living in New Zealand partially because of you.

Leo
Really?

Derek
Yeah, because... I held you up as a role model who was becoming a successful writer from Guam. And when I was sitting there thinking I needed to be in the middle of things, I need to be where the media centers where everything's happening, then I thought, you know, if Leo can do it from Guam, well, then, dammit, I can do it from New Zealand. So it's like you were an inspiration for me moving to New Zealand. I really, it wasn't like you were just one of a hundred reasons. It was like it was three reasons to move to New Zealand. And, you know, number two of three was like if Leo can do it from Guam.

Leo
Oh, that's amazing. Actually, I had no idea that was the case. That makes me even more excited to talk to you. So really cool. I haven't ever actually been to New Zealand. I'd love to go one day.

Derek
It's no different than California.

Leo
One thing I've noticed about you, looking at your bio, it's this long list of all these really interesting, fascinating things that you've done in your life, explored. You've launched businesses, sold businesses. Now you're passionate about creating anything really. And you are constantly putting out more stuff, not for monetization or profit, but just because you like to create, serve, and do interesting things.

So, I can actually start anywhere. I have so many things that I could talk to you about. I'm like, oh, I want to talk to him about that and that and that. I was looking at all your books. Some of them I've missed over the years. So we can start anywhere, but I'd love to zoom in on resistance, uncertainty, and fear around meaningful work, which, you know, as you know, is the theme of this season. Does that sound good to start with?

Derek
Yeah.

Leo
Okay. And we'll see where this leads us. We might actually go to talking about nomadism and all kinds of other fun things. So, yeah. One of the things that fascinates me about you is that you're constantly in creation mode, and you seem, at least from the persona I've picked up on, to be very focused, you single-task, and you really pour yourself into something. You're devoted to the creation you're doing, which is an inspiring thing.

If I'm wrong on this, please feel free to correct me, but that's something that has inspired me. I'd love to dive into that, but just before I saw your kind of eyes go up. Thinking, am I getting that wrong?

Derek
No, that's very right. I was just thinking of what aspects of this might be useful for your listeners. And I'll name two things up front: the monotasking or single-tasking is partially my nature, but I think it's mostly learned the hard way. I think a lot of us, most of us have too many things we want to do, and we feel torn, or we can dissipate our energy, distribute it too widely, and nothing gets done, or we just sit there in a state of paralysis.

So that's one thing I want to address. So that's the donkey and the magnifying glass. I'll get to that in a second. I'm just saying them out loud so I can remember these. And then the other one is more of the soul-searching, noticing what excites you and what drains you. That's why I keep making things instead of, say, supervising other people who are making things, is because I've just noticed. Yeah. Okay. We'll talk about this one first. We'll get back to the donkey and the magnifying glass.

Leo
Okay, great.

Derek
So I think the ultimate compass we should use to guide our actions is the choice between what excites you and what drains you. So, what's giving you energy versus what is sapping your energy away. And what's interesting about fear is that fear is energy; fear and excitement are two sides of the same coin, as the saying goes, right? The fear of something means that that thing is exciting. Fear is energy, which is the opposite of boredom. So, what you want to steer away from at all costs is boredom.

If something is boring you and just draining you or making you feel like going to sleep, and you literally get sleepy when you do this thing, then that's something you should be avoiding. But if something is scaring you, and hopefully at some point in the season, you'll talk about the War of Art and the resistance. Are you going to address that?

Leo
Oh, absolutely. Steven Pressfield's work?

Derek
Yes, it's Steven Pressfield's beautiful metaphor, personifying the resistance, almost like the devil, you know, with a capital D. The resistance is a person, a devil, a demon that tries to convince you that what you should be doing is watching TV instead of writing your book. It's there to tempt you, like, no, no, no, come over here.

So as long as you can identify the resistance as fear, and then be thankful that you're feeling fear around this thing, then one of my life mottos is, "Whatever scares you, go do it." If you're feeling fear about something, that is what you should be doing. Partially because this is something that excites you so much that it's energizing you. Even though you're feeling it as fear first, it will be the flip side of that coin afterward. But also as a life path. If you keep steering towards whatever scares you, then over and over and over again, you'll no longer be scared of these things.

So often, we're scared of something because it's the first time, and once you do it, you go, "Oh, I can do that." Then, yeah, another notch in your belt, another thing that you know that you can do now.

Leo
That brings up a couple of questions for me. I don't know if this is the right time to interject. You're on a great train of thought, and I'd love to come back to the donkey and the magnifying glass.

Derek
I won't forget.

Leo
Okay, great. That's a great curiosity hook. It's gonna I definitely need to have that resolved.

I love that you talked about fear being energy and that it can actually energize you. But the question I have, I have a couple of questions. The first one is, for some people, they get so caught up in anxiety around that fear, the thing they're afraid of, that it can tighten their body up and feel draining. So I'm wondering, is there a way to work with that so that the thing you're afraid of doesn't have to be draining? You know what I mean?

Derek
I think it's easier if you think of it in a less ambiguous way and imagine yourself, say, about to bungee jump or skydive, or something, fill in something that is a more obvious example of fear. Whether you've done it or if you can just imagine doing it, you know that it's safe. You sat at the bottom and you watched 20 people bungee jump. This place has been doing it for 20 years. They're safe. You know that you're going to be fine.

Now you're standing on the edge of that ledge with a harness around you, looking down at the ground below, and everything in your body is saying, "No, you're stupid!" And you have to override your instincts and just tell yourself, "I don't want to do it, but I'm going to do it." You just say, "All right, everything about this feels wrong, but here I go. I'm going to do it anyway."

Believe it or not, that's the kind of self-talk I do, even when I'm just sitting down to write or take on a project. I know I should do, and I'm scared to do it. And that voice, called the resistance, is telling me to do anything but do this. "Maybe you should eat first. Maybe you should go for a walk. Hey, go call a friend, go watch something. Look at this funny video." It's like standing on the edge of the ledge about to bungee jump or something. I just tell myself, "I don't want to do this," but fingers on the keys, shut off the phone. Here we go. And I make myself do it.

One of my favorite metaphors is, if Steven Pressfield can personify the resistance, I like to personify inspiration. Inspiration is gorgeous. She is loving, wonderful, all-accepting, kind, and encouraging, but she will never make the first move. You have to make the first move every time. After you begin, even though you don't want to, then she will come towards you and go the rest of the journey with you.

Leo
That's amazing. So what I'm hearing, what I was talking about was this kind of anxiety that can really close us down and be draining. But that's kind of the anxiety of standing there at the ledge. But on the other side, if you're actually able to jump, it's releasing and it's energizing. So the draining part, just standing there, not taking that leap.

Derek
Yeah, the strongest I ever felt this was years ago when I was running a web hosting company called Host Baby, and all of my musician clients had been asking me to make this thing that was like a website builder, where they didn't know HTML. They were all hiring individual web designers that would flake away and screw them over or something. And I knew that if I were to just build this thing, where I could ask them their band name, their album name, their song titles, and such, upload, put in your calendar dates, go, and it would generate an HTML page.

It was really hard to make it. I didn't know how to make it, but I knew it had to be done, and I knew that I was the one to do it. I knew that if I did it, there would be giant rewards, not just for making a lot of people happy, but I knew a lot of people would be very happy to pay a lot of money for this thing.

I just remember sitting in my living room almost every day, every morning, noticing that I was doing everything but what I needed to do. I would curse, kick, scream, and use every swear word I knew. Then I would just put my fingers on the keys. Once I began, every time, inspiration would finally come meet me.

I feel all those same feelings, but I override them and make myself do the thing that I know leads me to where I want to go and who I ultimately want to be.

Leo
It sounds like that was probably like 20 years ago, so 20, 25 years ago. It sounds like 20, 25 years of doing that kind of thing over and over has probably built up a lot of trust in yourself. You know, if I finally just take the leap, it's going to be everything I've wanted. Like I know how that always turns out.

Derek
Actually, no, it's still better than it was 20 years ago. It doesn't get any better.

There was this Nobel Prize-winning psychologist, behavioral economist Daniel Kahneman, who's been studying cognitive biases and things like this for 50 years now. Somebody asked him recently in an interview, like, so since you've identified all these biases, are you able to override them? He said, "Nope, it never gets any better."

Leo
"I'm still human."

Derek
Yeah, I'm still a victim of all of these things, no matter how much I identify them. So yeah, no matter how much you and I can talk about this, I still struggle with it as much as everybody else.

Leo
That's actually very good to hear because I think people can put others on a pedestal like, "Oh, this person has it solved and figured out, and they don't have to worry about this, and it's easy for them now." Yeah, and I can relate. I still face my resistance. It's still there, the same fears that were there for me when I first started all of this. It still comes up. They're just fears.

The difference now is that I'm better at spotting them, and I don't make them quite as significant as I used to. Still a little bit significant, but yeah, I still struggle with it, but I think I'm able to work with it a little bit more effectively.

Derek
The definition of courage is not to not feel the fear, but courage is to feel the fear and do it anyway.

Leo
Yeah. Yeah. One more question before we get to the donkey in the magnifying glass.

You talked about avoiding the stuff that drains your energy and going towards the stuff that gives you energy, which I love. It's very clarifying, a great compass. But I'm wondering if those are fixed. You know what I mean? That things that drain your energy, do you always have to avoid those? Can't you shift that? What if you wanted to be energized by something you typically find draining or that would create something in your life if you moved toward it? I'm wondering, yeah, what you've noticed about that.

Derek
Okay, two thoughts. Where I thought you were going with that is that it changes over time. There are times in my life when what excites me is solitude. I need to get out of here. I need to get away. I just want to be alone. That is more deeply exciting. And then there are times in my life when I've been alone in paradise for too long, and what's exciting is to be in the middle of everything and take on a bunch of new responsibilities. So it can change with time. That's the problem, I think, with people labeling themselves as introvert or extrovert. I think those can swing like a pendulum. But you're talking about deciding that you wanted to change it.

Leo
Yeah.

Derek
Yeah. For that, I journal in a way that I only recently, after many, many years, found out that this is called cognitive-behavioral therapy, or what I do in my journal has a name.

Leo
It has a name.

Derek
Yeah. So the kind of journaling I do is usually when I'm feeling a little conflicted about something, feeling incongruent, I start asking myself questions. I start challenging my beliefs, or I start opening up other options. I brainstorm past the first two or three that come to mind. Like what? Okay. I'm stuck in this situation. What's the solution to this? I go, blah, blah, blah. Here's a solution. I go, Ooh, that's good. I'm tempted to stop right now. I'm going to make myself do another. What's another solution? Blah, blah, blah. Ooh, okay. Well, no, I don't like that one as much. What's another one?

I make myself keep going and do at least five, ideally even 10 different solutions. And not just to tick a box, but each one I take it seriously. I think of something, it would be a radically different way to approach this.

Derek
I love this. This is incredible.

Derek
Thanks. And for the kind of example you're talking about where, say I'll just pick one. Say I'm currently not prioritizing fitness, but I want to prioritize fitness. That it currently drains me, but I want it to energize me. In that case, this kind of journaling is ideal, that you just, you start stacking up reasons, you ask yourself, what would be all the benefits of if this was my top priority. How much better would I feel, or then you reverse it, how bad would I feel if I don't prioritize this, if I keep going on this trajectory. Where will I be in 20 years?

Assuming that those things get even worse over time, you know, it's not a straight trajectory, it kind of, then, how much worse is this going to get if I don't prioritize this now? You just start stacking up vivid images in your head of the price you will pay if you don't make this change and the huge benefit you'll get if you do make this change in your values. And even then, sometimes it doesn't fully convince you, but you just start to do the actions. You start to embody it instead of just theorizing it, you know, you start to do the thing again, whether you want to or not.

Oh, here's a perfect example. Right outside my recording booth where we're talking is my squat rack with my deadlift weights. And I do it many times a week. Still, after years, I never, never, never want to do it. I only do it because I have to do it. I'm 53 now, and those first two squats always hurt, and I'm like, Oh, and I know it's going to hurt, and I curse it, but I do it. Almost every time, by the time I get to set three, set four, I'm really glad I'm doing it. I feel badass, I feel better. But every time, you know, here it is two days later, time to do it again. I don't want to do it, but I've aligned my values in such a way that I know I need to do this thing. So that's that.

Leo
Yeah, I love that. And I can so relate to that, the squat example. So thank you. I have a squat rack right below me, so it is calling to me to go do a workout after this. And it's like, Oh, do I really feel like it? Do I want to?

But I always feel so much better. Yeah, at least halfway into it.

Okay, let's get to the donkey. It's been waiting for us.

Derek
The donkey is going back to your original question of, we've got too many things, or you said that I tend to focus on one thing at a time.

Leo
Single-task and be really focused and devoted.

Derek
Yeah. There's a story of Buridan's donkey. I think was an author long ago that made up a fictional donkey to explain a point. I think he was a French philosopher that said.

Buridan's donkey is halfway in between a pile of hay and a bucket of water, and he can't decide. He keeps looking at the water, but then looking at the food, and he can't decide. And he ultimately dies of hunger and thirst, because he just can't decide.

The thing is, we're not a donkey. You can have the foresight to know, I can go to the water first, have a drink, then walk over to the food, and eat, and then go back to the water and have some more water if I want, and even go back to the food again if I want.

We can use the future because thinking of the future is... almost our unique human capability. We're tool makers, but we're also future makers. We are the only creatures, I think, maybe there might be one other mammal on earth that does this a little bit, but nobody as much as us, making the future. We predict, we imagine.

So if you're feeling torn between multiple things you want to do, just think of the donkey and don't be a donkey. Just know that you can go do one right now, and all those other like, Hmm, yeah, but I also kind of want to do that. Okay, do those later. You have to start one right now. Otherwise, you're going to die of indecision. Don't be a donkey. Go just do one right now.

I have this yearning all the time to do other things. But what really helped is I just started creating a little folder on my hard drive of my computer in my journal, where all of these other things I want to do, I will indulge them for a few minutes or a few hours. I'll type out all the things I want to do and all the ideas I have around it, and I'll just put it into a folder. Those are all in a folder called 'possible futures.'

I know that those can happen someday, but later. Right now, I need to finish the thing I'm doing because I've also felt the pain of trying to do too many things at once and never finishing any of them because I was doing too many, too dissipated, you know?

So I make myself do one at a time, no matter how badly I am yearning to do the other things. I make myself finish the one I'm doing now so that I can get the pleasure of something done, something launched, something released, and be done with it. Then I feel more wholehearted about turning to the thing in my 'possible futures' folder that I'm excited to do next.

Leo
Okay, let me ask, I love this. Thank you for sharing that. And I love the donkey story. I've heard it a long time ago, and now you've brought it to a place where I can actually use it. So thank you for bringing that in.

I have someone who I've been working with, and he wants to choose a project to work on. He has at least five, maybe ten things that he's really excited about doing in his life, from music to art to comedy to writing and podcasting. But he's stuck, like that donkey you talked about, just stuck. If I choose this, then I feel like I'm shutting off all those other possibilities. So that directly speaks to what you were just saying. How would you suggest this guy works with that? Given what you were just saying.

Derek
It's a mature realization that you can do anything, but you can't do everything.

Leo
Not right now at least. That's for sure.

Derek
You have to do one thing and use the future to do those other things. But also, think in terms of a well-lived life, get out of yourself for a second, and think about your heroes, the people you look up to the most. They're probably great at one thing, and that's why you love them. That's why you love this person's music or that person's books because they do one thing amazingly well. They're not also an expert mountain climber, an excellent film composer, and a botanist.

Leo
You're not the best example of that.

Derek
Well, no, I mean, I have only really done a few things in my life really well, to me.

Leo
You're a musician, an entrepreneur, a writer. So anyway.

Derek
I was a good musician, not great, but I was good. I was not a good entrepreneur. I stumbled into the right place at the right time. I started a music distribution company at the beginning of the dot-com boom when nobody else had done it yet. I was the only one. So that was just luck. The further I got along that path, the more I realized I'm not good at this.

Sometimes I wonder, like the singer of the Red Hot Chili Peppers, he is not a good singer. How long do you go along this path before you realize, like, 'Man, I am not good at this.'

Leo
Being successful without being good, right?

Derek
Yeah, exactly. You can be successful without being good. But I think about Danny Elfman, who's now a great film composer, started out as a kind of middle-of-the-road pop star, I think he was in the Buggles or something like Oingo Boingo or something like that. Not great at that, but then he started doing film composing.

So anyway, I think that for me, I dabbled in a bunch of things, but I realized that all along it was my writing that was central to things. I think the reason people liked Seedy Baby, my old company, is because of the way I would talk about it and the spirit I gave it through my writing.

Leo
Well, every time you say something, five more questions pop up for me, so I'm just going to ask it. How did you recognize that you were writing and you recognized that writing was the thing? Was there a moment for you?

Derek
Yeah, there was a very clear moment because I defined myself as an entrepreneur and a programmer that sometimes shares what I've learned in writing, and that's how I just publicly define myself without overthinking it. And then one day, I had to ask myself, like, 'Wait a second, I'm calling myself an entrepreneur, but I haven't started a new company since 1998. I have no right to call myself that. An entrepreneur means this person who starts a thing, who launches it. I haven't done that in so long. I really have no right to call myself this.

And programming, yes, I love it. But who are my heroes? And really, my heroes, these are my favorite authors. These are the people that I have up on pedestals that I want to be more like. Are these thinkers? I thought, 'Well, I think that kind of tells me what direction I'm facing. You know, if you're looking up at someone, that tells you which direction you're facing.' So that's where I'm facing. That's where I want to go. So that's when I realized, yeah, I think I'm not an entrepreneur, and programming is my hobby, but ultimately, I'm a writer. That's my top priority.

So getting back to your friend who has 10 different things he wants to do, if you step outside of yourself and think of your heroes, they're probably people that are just really great at one thing, and nobody cares what they're not good at. So I think it's okay to keep those other interests as just interests without thinking that you need to go all the way down that path.

Right now I've got a minor, like a university, you know, you say you've got your major, and some people have a minor. So these days I'm thinking like I've kind of got like a minor in anthropology. I am so fascinated with other cultures and other mindsets and other worldviews, and I want to understand them so badly. I'll stay up all night long and I'll just devour anything teaching me about another way of seeing the world. But I'm not going to make it my career. I'm okay to just leave that as an interest.

Leo
Something you're fascinated by.

Derek
Yeah. And that's enough. I don't have to add that to my list of careers to do. You know, it's just an interest.

Leo
Okay, I've pulled us off the topic, going down some side roads. Should we go back to the magnifying glass?

Derek
Yeah, you remembered. Cool. The magnifying glass is yet another nice visual metaphor. If you ever, as a kid, played with holding up a magnifying glass in the sunlight and focused it on one single spot, making that spot catch on fire. You could do it to a piece of paper, you could do it to a stick. The big idea is that sunlight on a stick won't catch that stick on fire. But if you focus the power of the sunlight into a single, tiny, focused point, then it'll catch on fire.

I think of that with our pursuits. If we spread our sunlight widely, then nothing catches on fire. But if we focus our sunlight on one single thing, then it catches on fire.

Leo
It's a beautiful image. Could I ask about tactics around that? So on a tactical level, let's say you want to focus on writing a book right now. What are some of the things that you do to get that magnifying glass into action?

Derek
Okay, I actually had to do this yesterday for my new book. I got off track for a few weeks, almost a few months, doing some other things that came up because of travel. I had booked a trip, and then that's kind of my minor in anthropology. I got so fascinated with my trip. I went to Dubai for the first time, not expecting anything. In fact, it used to be on my top 10 list of places I'd never want to go. It sounded like the most shallow, crass, materialistic shopping mall of a place. I'd be happy if I never went there in my whole life. But then my plane went through Dubai. So, instead of a two-hour stop, I made it a two-day stop.

Oh my God, I was blown away. I'm fascinated. I love it. It's a fascinating culture. So now I'm learning all about it. I'm digging into an audiobook about the Ottoman Empire and learning about Bedouin culture. Picked up a book on Arabic. I'm fascinated with this culture, and I got a little distracted. I wanted to turn my attention to my book. So I had to get myself back into a mindset.

Specific tactics are to surround yourself with inspiring wisdom on that subject. Let's generalize it a bit. In my case, I went and pulled up some of my favorite books about writing, rescanned my notes on those books, and got super inspired again on the subject of writing.

But I've had to do this with programming before. I still enjoy programming, and when I need to do some programming, I pull up some of my favorite books on programming. I read some of my favorite bits of wisdom and ideas that I've collected on programming, and I get myself re-inspired about programming.

Same thing with health, fitness, lifting. I've read some great books on weightlifting, fitness, and health. If I'm ever feeling like, 'Oh damn, this has fallen too low in my priorities. I need to bump this up again.' All I have to do is take in some of my favorite bits of wisdom around the subject. I get reinvigorated, refocused, and driven to do it again. So that's my main tactic for anybody that needs to do something.

Leo
After we're done recording this, I'm going to send you an email asking for some of your favorite books on those topics. I know people are going to kick me if I don't ask.

Derek
Actually, so Leo, actually they're all in one place. You might know already, but everybody, go to sive.rs/book. That will bring you to a list. I started taking notes in 2007 because I had read a couple hundred books before that, and I realized I was forgetting all of these books I had read. I knew I had read that book eight years earlier, but damn, I don't remember anything from it. I don't want to read the whole thing all over again. So, starting in 2007, I underline my favorite ideas or circle my favorite thoughts when I'm reading a book. After I'm done reading the book, I type my favorite ideas from that book into a text file. Now I can get rid of the book and just save the text file with my favorite ideas from that book. I review that often.

Leo
It's a great collection. I've gone through it myself several times.

Derek
After keeping those to myself for a couple of years, I decided to put them on my website. So now you can see every book I've read since 2007. I think there's almost 400 books there, and most importantly, I sort them in order of my top recommendations. When somebody says, 'What's your top recommended book about programming, travel, or fitness?' They're all there, and you can start at the top of the list.

Leo
I forgot that you did that. Okay, perfect. We don't need links from you then. You got it all there.

Derek
That's the one and only. There you go. Yeah.

Leo
You mentioned the book you're currently working on, something like 'Useful, but true.'

Derek
'Useful, not true.'

Leo
Shoot. Okay, I was an important distinction. I've read through the blog posts that you have there that can be a part of this book. I don't think I'm going to do a good enough job of summarizing it, but I do want to dive into how it might apply to the topics that we're talking about here.

Derek
Sure.

Leo
Would you be up for summarizing what the book's about?

Derek
Hey, time me. I'm going to see how quickly I can summarize the book. Ready?

Leo
Okay, great.

Derek
All right. So first, I have to say that 'Useful, Not True,' this book is personal. It's about you. It's not about other people. While we're talking about this, forget what other people do. Just think about your own mindset, your own actions that you could take.

So first, it's about pointing out how most of the statements that you hear people say are spoken as truth, but they're just perspectives. It's just somebody's opinion. It really helps to strip away all of this subjective opinion and scrape it down to only indisputable objective, observable facts. Those are the only things I consider to be true. Everything else, I think, is negotiable, subjective, able to be seen from another point of view.

This is most useful for the things where everybody agrees. It's hardest to do for the things that everybody agrees on, like it's good to call your mother. Everybody agrees that such and such is this way. It's hard to strip those down and realize that those aren't necessarily true either.

Once you strip it down to the bare facts, the next step is, for yourself, you can think, kind of like we were talking earlier, what would be good for me to believe? What beliefs are useful for me to hold right now that will help me be who I want to be?

Instead of relying on saying that these beliefs are true, you say that these beliefs are useful to me. Because if you start declaring them to be true, well then you're going to argue about whether they're true or not. If somebody disproves it as true, then you've been knocked off, you'd have that rug pulled out from under you.

So let's stop even trying to argue that anything is true, and let's just think of whether this is useful. After you do that, you can start to realize that all the rules and norms of society are actually just a game, not so different from the game we made up as kids when you'd make up rules, like, 'Now I'm standing on the couch, and if you touch the floor, it's hot lava, but not if I have my fingers crossed. But if I hit you twice, then you're in it.' We make up games as kids and understand it's all just fun.

What's funny is that when grown-ups get older, they suddenly make these games that they treat super seriously, and we think of them as laws, as if they're laws of physics, but they're just rules that somebody made up, somebody agreed, and somebody lobbied for.

If you find out that the game is stacked against you, if the rules of this game are against you, you have the right, and it's wise to quit that game, to not play that game, to either take another role or make a new game or just change the rules.

The common thread through all of these thoughts is that we should not think of anything as necessarily true or not true, but just whether it's useful to us. So, useful, not true.

Leo
Got it. Three and a half minutes.

Oh, okay. I got three minutes and 32 seconds. Thank you.

Leo
That was beautiful. A couple of things that struck me about that as you were talking about it. And one of them is it's liberating. It's almost like the matrix, like knowing that you're in the matrix, you know, like that kind of thing where it's like, 'Oh, this is all a game. This is all made up, and we can choose to play that game or not.'

Derek
Yes, the scene in the matrix is at the very end when he's realized it's all just code and kind of embodies this now. They're shooting him with bullets, and he just looks at it. He's like, 'No, I think not.'

When you realize that all of these statements that people say so emphatically try to convince you that they're true, you realize it now? That's not true. It's useful for you to believe that, and I can see why you believe that.

Leo
Or not, it might not be useful.

Derek
Yeah, sometimes it's, in fact, sorry, I left that out at the beginning, but I think that most things that we consider. Sorry. Most of the disempowering beliefs that we hold, most of the harmful thoughts we think are not true. It really helps to see that clearly, that none of these are true. And again, even though I'm writing this book and I've been immersed in this thinking for a long time, I still catch myself thinking thoughts like, 'I can't do what I want to do from here,' or 'I can't do that because I have a kid.'

And I'll say this as a truth. It's like, 'Well, yeah, of course I can't do that because I have a kid,' or 'I can't do this thing from here.' I'm just picking two dumb examples. It feels like a fact. And then I have to catch myself like, 'Oh, wait a second. Hold on. Useful not true. That's not actually true, is it?' So then I stop and I... If you can think of even one counterexample, if it's arguable, if anybody can take the flip side of that argument, well, now it's no longer true. It's not necessarily false. But it's not absolutely, indisputably, necessarily true. Once you prove something is not necessarily true, well, then, yeah, now it's up for creative interpretation, and you can think of a more useful perspective.

Leo
Yeah, it's like you're removing these imaginary walls, and you get to choose them or not. Like, I get to create whatever I want to create.

Derek
Imaginary walls. Yeah. Calling something true puts an imaginary wall there.

Leo
That seems really solid, right? Like, 'Wow, that's definitely solid. I need to avoid it, not walk straight into it.' But you're, what you're putting people at is some awareness, like that's not a solid wall. You can choose to believe it or not. Yeah. But also putting them at power, putting them at choice. That's a really empowering thing. Really beautiful.

Derek
Thanks.

Leo
You actually already answered one of my questions that came up for me, which is, you know, what, as you write the book, what are some of the things that are coming up for you? You know, some of the things you're noticing as not necessarily true, but maybe not useful, you know, and so you have started on that. Is there anything else that you've noticed?

Derek
Oh God, so many. This book is taking me much longer to write than I thought because it's a personal exploration of a subject that I've felt instinctively for years, but I hadn't really stopped to dissect it. It's been in between the lines of all of my other writing for years.

I think even a lot of what people liked about the way that I spoke about business in my first book called 'Anything You Want.' I talked about entrepreneurship, and a lot of people liked it, which I was really surprised by, but it's because I was looking at common things in a new way. It's like, well, the common narrative is, let's say you got to make the most profit you can. And I'd say, well, there are other ways to look at it. You could think about it in terms of making just enough and trying to make more people happy as long as you're making enough or thinking of this as your own little place where you get to control all the laws of this small universe, which is your business. And people went, 'Whoa, wow, that's really interesting.' And I went, 'Oh, I guess this is just...".

Leo
I will link to that as well.

Derek
I just started thinking about these things that way long ago. And then I realized in between the lines, I'm always taking what people say is true, doubting it, and then brainstorming other ways I could look at this and thinking about which of those ways is most useful for me. To help me be who I want to be.

Leo
So as you write this book, what have you noticed coming up? Any beliefs that are not so useful, not true?

Derek
Oh, just tiny little day-to-day things, but I see them in my friends. It's interesting learning about placebos and nocebos, the things that harm us that aren't true. It's also fun to see other ways to play the game.

Cute tiny story I've never told. My kid was eight years old when his school did their annual football match, and the school takes it very seriously. Sorry, soccer. We were in England at the time, they called it football. So their annual soccer match, and his school took it very seriously. My kid has no interest in sports.

So I dropped him off at the big school sports day and picked him up at three o'clock. I said, 'How did it go?' And he had a big smile on his face. He goes, 'It was great.' He said, 'I had so much fun.' I said, 'Tell me about it.' He said, 'Well, everybody's really mad at me.' I said, 'Why?' And he said this with a smile. He didn't care. He said, 'Well, they told me that my job was to be a goalie, so I guess I'm supposed to protect the net, but my best friend, Cyrus, was on the other team. And so I really wanted him to win because he's my best friend. So every time they kicked the ball at the goal, I just pretended to jump for it. But I made sure to miss it every time.' He said a bunch of people yelled at me, but I don't care. He said Cyrus was really happy, and his team won, which made me happy.

Leo
That's so sweet.

Derek
He was so congruent about his happiness with this, didn't mind one bit that all the people were yelling at him. I thought, again, this is a beautiful example of different ways to play the game. You know, you could start a business to see how much money you could lose, like how much in the hole can I go? Maybe I can convince a bunch of investors to invest in this thing and then lose all of their money because I've just given it to people. There are so many different ways to play the game.

Leo
See how many people you can piss off. I think that would be fun.

Derek
Yeah. Or just, you know, how many people can you help? I mean, wasn't that kind of like Schindler's List at the very end? He's trying to save as many people's lives. And finally, they take him away as he's signing his name one more time, trying to write passes to just, it's just like he's given away everything he has. Whereas all the good people around him were thinking like, how can I profit from this war? His thing was like, no, how can I lose everything? Just give it all away. And, you know, they're just, and it made him happy, and we celebrate him, you know, whatever, 180 years later.

So. Yeah, it's a nice reminder that there are other ways to play the game, that even somebody saying here's the rules of the game or here's how you play, that's not true either.

Leo
I love that. Thank you for sharing that.

I am aware that we're running out of time, which kind of makes me sad because I think I could talk to you for about 10 more hours, maybe all night. But what you've shared here is liberating. And I think what it encourages is inquiry, like really deep inquiry, which is something that you embody, and you don't just talk about it, you embody inquiry, just asking yourself questions and then coming up with 10 possible answers to that.

I think that's what your book also inspires. It's just like people to take a look at the things that they believe to be true and then to choose what do I want to believe? Is this useful? Is this not? Is there a new way to play the game? Do I want to play that game? Or is there another game I want to play? I think that's really incredible.

Derek
My favorite one is, I often use the phrase, 'In a perfect world,' dot dot dot dot, you know, 'In a perfect world, how would I play this game?' In a perfect world, what would the scenario be? And just making your dream come true scenario, which then when you're done, you can usually look at it and go, 'Boom. I could do that.'

There's usually not actually something stopping you. You just have to open up your mind and think about what your ideal scenario would be. And then it's possible to just go make that happen.

Leo
That word 'possible' is I think the thing that really stands out for me, like you're inviting people to look at what might be possible. And I think that's actually something that a lot of your work does. Like, 'Oh, what could be possible?' It's just being in that inquiry of like, 'Yeah, what would I like in the perfect world? What would I love?' And we don't ask ourselves those questions enough, I think. Well, at least most of us don't. I think you do.

I'm excited for that book. I'm going to link to that as well. You know, I know it's an ongoing work right now, and people can sign up to get updates. But I just want to thank you for coming on and sharing some really meaningful work and some thoughts around resistance and donkeys and magnifying glasses.

Derek
Yeah, I also, I don't have a podcast of my own yet, but someday I want to ask you 10 hours of things too.

Leo
So we should actually book 10 hours.

Derek
Yeah. We'll get a special subscriber-only 10-hour podcast.

Leo
We'll do some squats and go into that recording booth of yours. I think it'd be amazing.

Derek
Anybody listening to this, please send me an email and introduce yourself. It's the main reason I do interviews like this. I'm clearly not here to promote something, but I really, really, really like the people that I meet that introduce themselves. So if you're a fan of Leo's podcast, if you're a Zen Habits kind of person, you're my kind of person, and I would like to know you. Email me; go to my website. Just click "send an email." I reply to every single one.

Leo
That's the perfect way to close. Thank you, Derek.

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