Derek Sivers

One Percent Better

host: Joe Ferraro

monomaniacal philosophy, pursuing fears, goals and actions, personal interests and values, self-improvement

episode web page

listen: (download)

watch: (download)

Transcript:

Joe

My guest today is serial monomaniacal person Derek Sivers. Welcome to 1% Better.

Derek Sivers

Thanks, Joe. The word you put after the word serial. You said what you?

Joe

You said monomaniac on your website, among other things. What’s that mean?

Derek Sivers

It’s a word I learned recently because I really like doing one thing at a time. I found that I have almost infinite patience and energy if I’m doing only one thing. But as soon as I try to do more than one thing at one time, everything feels draining and stressful. So I learned that monomaniacal means somebody who is interested in only one thing at a time. And I went, “Oh, that’s me.”

Joe

When I was preparing to speak with you today, one of the things that I wanted to spend and invest some of our time doing is defining terms and not trying to be too fine or too cute with it. But right away you get me thinking. You say one thing at a time. But the reason I put the word serial in front of your name is because you’ll move from this to this. It was a circus performer, entrepreneur. But when I think of your life and the work that I’ve studied, you have these threads that run through it. So let’s take a step and actually try to think about what you mean by one thing at a time, because right now you and I are here. But someone who’s listening to this is on the treadmill. They’re walking out in nature and listening to our conversation. So I think it gets very interesting when we try to define what we mean when you say one thing at a time.

Derek Sivers

I don’t know if we invent threads or if the threads are always there to find, but I think most people’s lives, even if it seemed like they had nothing in common between the different things they do. You could find a common thread, even if it’s just in your intention or even if the common thread is, I’ll just go with whatever pays the most. You know, to me, I always felt that I was experimenting and exploring with a spirit of like, let’s see what happens. Like I’ve never done this before let’s see what happens if I try that. That’s the common thread for me that’s gone from my fascination with making music that lasted all the way from age 14 until 30 or so. My fascination with helping musicians. My fascination with writing and pop philosophy and ideas. Throughout all of these, there was this considering a new idea I hadn’t considered before and then wanting to turn it into reality. So with music, I’d have a musical idea that had never existed before. You know, like this kind of a Beatles melody mixed with this kind of a James Brown beat, and I’d have to turn that into reality. To test it out. And then later, when I was helping musicians, I was like, “All right, there’s really no place that allows independent musicians to go directly. Let’s see if I can make it. Let’s see if I can turn that into reality.” And did that for ten years. And now it’s like I have this theory of life that we should do whatever scares you and expand your comfort zone. Right now, that’s just in theory, but let me see if I can put that into practice. Like this is something that doesn’t exist in my life yet. Let me see if I can make this exist in my life. To me, those all feel like the same common thread. If even if from the outside it looks like nothing in common.

Joe

And that leads me to one of the core ideas I want to speak to you about today in your book, “Hell Yeah or No”. You close the book by saying, “I heard this idea as a teenager, took it to heart and made this rule. Whatever scares you, go do it.” And that’s how you leave the book. You also title the book Hell yeah or No. And when I think of those two ideas, I think there’s some tug of war there. And I would love for you to talk a little bit more about that. So for me, when I think of Hell Yeah or No, if there’s any doubt, I’m not doing it. And when I hear your last line, you say that precise feeling of fear is actually what we should do. Can you say more about that?

Derek Sivers

Ha ha ha. I’d never directly contrasted those two before. I’d never thought about that those two might be at conflict. You’re the first to mention that. Yeah. I hope this doesn’t just sound like a cop out to say that different tools for different times. I don’t think that hell yeah or no is a philosophy for all of life that you should use at all times in all situations. It’s a very specific tool in the toolbox, and I think it even says in the very first sentence of the original essay. Hell yeah or no. Like if you’re feeling overwhelmed with too many options, then consider this. So it’s like if there’s a screw on the wall that has the flathead line in it, then reach for the flathead screwdriver. All of these tools start with an if for a situation where you might need this tool. So hell yeah or no is a very specific tool for being overwhelmed with options. But whatever scares you go do it to me is much closer to a general life rule of thumb. It was actually originally taught to me as whatever you’re thinking, like whatever is captivating you, go do it instead of just thinking about it. And I liked the version of whatever scares you go to it because if you do something that scares you, you’ll almost always find that once you do it, it no longer scares you. You’ve done it. It wasn’t as bad as you thought. And now this is something that’s in your realm of possibility, your realm of experience, and it no longer scares you. And what a cool way to go through life. Finding things that scare you, steering towards them, doing them, and then no longer being scared anymore. Then finding the next thing that scares you, moving towards it, doing it. And now that doesn’t scare you anymore either. It’s a nice life strategy.

Joe

I heard you a moment ago say almost always. And that was one of the thoughts I had. Sometimes with public speaking. People are constantly afraid and it doesn’t go away. Something maybe as banal as a roller coaster. You know what’s going to happen. You know, the third turn is going to get you rocking and rolling, but you’re still scared. So I think that that almost always can be kind of crucial.

Derek Sivers

Yeah. There’s also when we use terms like scared or happy or even honest. There’s always a couple different levels of it. Like, there’s shallow happy and deep happy. To me, shallow happy is having an ice cream. Deep Happy is being proud of yourself for not having the ice cream. Like, that’s a deeper happiness to me. Honest is when a friend calls and says,” What are you doing?” And you say, “Nothing.” And deep, honest is a friend calls and says, “What are you doing?” And you say, “Actually, I was just sitting here thinking about Dubai for some reason.” “Why? Why Dubai?” “I don’t know. Just at the very second you asked me, for some reason, I was thinking of Dubai.” Like, there’s always a deeper level of honesty, a deeper level of happiness. And I guess the same with what scares you. There’s kind of a shallow scares, which can be a thrill, and there’s a deep scares, which is just like, “Oh God, oh no, that would be devastating. I couldn’t do that. I would lose everything. Who would I even be if I were to do that? It would shake my very foundation.” So you can interpret that in whatever way works for you.

Joe

Yeah, That’s helpful. Thank you. You’ve described yourself as a slow thinker. What does that mean?

Derek Sivers

I don’t know. I’ll get back to you tomorrow, huh? It is honestly like that. I very often, when recording a live interview like this, will think of a much better answer the next day. In general, in conversations, in life situations. I find that a day or two later my thoughts are much better. It takes time for things to sink in. Or to ruminate or to consider other perspectives that the the instant reaction you have to something is often like what we call a knee jerk reaction. It’s your default. It’s just impulse reacting and it may not be your wisest self. But if something matters, you sit with it for a while, you might start to think of other aspects. Other solutions to that problem or other angles to that question. So that’s how my brain works. I think that most people’s brains are like this and they feel a social pressure to answer everything quickly. But I put that out there on my site. I put that post saying I’m a slow thinker and went into detail on it. I think it’s sive.rs/slow. And a lot of people have thanked me for that because I think it called attention to it and gave them permission to tell people like, I don’t know, let me think about it for a bit. Because I think even socially we think we’re not supposed to do that. But it’s admirable in a way. It shows that you’re going to give this a real effort. You’re going to give it your time. You’re taking it seriously. When you say, let me think about that and I’ll get back to you. There’s something kind of honorable and honoring about saying that for sure.

Joe

Did it ever cause insecurity at a younger age?

Derek Sivers

Probably. I’m just not remembering it now.

Joe

Yeah, Now it’s beautiful. As someone who is-- we’re gathered around the virtual campfire of a podcast called 1% Better. I would love to invest a moment or two on the word better. You said it a moment ago in terms of better thinking, better answers. But when you think of that word, let’s give ourselves permission to be as broad as we want. 1% better is founded on the idea of self-improvement, small, incremental gains, lifelong learning. But when you think of that word, you said, you give better answers the next day. What’s top of mind when you think of better?

Derek Sivers

Well, there’s honesty that we mentioned earlier, like shallow honest versus deeply honest. If it’s a personal thing you might want to get more honest if it’s that kind of relationship, if it’s an intimate relationship where deeper honesty would deepen the bond between you, then you may want to go for the deeper honest. Which can take a little while to either get the courage or the self-knowledge to dig into. Let’s see if it’s creative. Then it’s finding a perspective that hasn’t been overdone. Finding an angle that hasn’t been explored before. I often think of I’m not a very visual thinker, but I like the visual metaphor of a very multifaceted jewel or a complex object. If you think about like a geode or an agate or some kind of interesting hundred sided rock that you might pick up from a jagged beach, that you can hold it up and look at it from so many different angles. And you might find one little angle if say you were an artist sketching, and if you were to hold it at one little angle, it would be completely different than if you just moved it an inch that way. You’d have to do a completely different drawing. And even the subjects that were considering, even if it’s computer programming or business or whatever it is we monkeys do. Thinking a little longer can help you think of a new angle that you hadn’t considered before that could give you an insight for how your solution could be better. Meaning more efficient, better meaning more surprising if it’s meant to be entertaining. Better meaning. I guess in general more effective for whatever your goal was.

Joe

More true, more true to the aim of maybe what you hope to accomplish. In a weird way, I think of conversations like that stone that you just held up. We have this conversation tomorrow. It’s different, there’s no doubt about it, Right? Not just our clothing, but our affect, what’s in the air. Right. It’s just you can’t duplicate a conversation.

Derek Sivers

Yeah. By the way audience, I’m going to tell you a little secret that Joe might not have felt okay to tell you. This is actually our second recording, we recorded four days ago on schedule. And I got really really sick during the recording and I had to call it off. I had to go. And it’s funny, what a massively different recording this is. Four days ago I was almost feeling faint. I mean, I was feeling faint and I was worried I was going to faint. And my answers were very weak and half assed. And here we are four days later, I’m feeling better. It’s like pow, pow, such a different conversation.

Joe

I feel totally different. I feel very comfortable. I feel very connected with you. I feel that this has actually done something for our relationship, wherever it may be. Connecticut to New Zealand. So maybe that is great to tell people that vulnerability piece and just there’s a lot that I learned in that four days that we should probably talk about it at some point and it’s just a cool thing. Maybe if we marry together, the idea of slow thinking and better, we arrive at one of my favorite pieces of yours and I wonder if you could tell the story of “Relax for the same result”. This beautiful story of riding a bike next to the beach. Could you recall that for people? I think it is a beautiful symmetry of those two.

Derek Sivers

Yeah. I used to live on the beach in Santa Monica, California, and it’s got a great long bike path. It’s like I think 15 miles and I lived about in the middle. So it was seven miles to the south, eight miles to the north. And I would do this round trip loop on it and it would take me. Well let me get to that. I would do this bike path so often that after a while I started getting kind of competitive about it. You know, I started leaning forward. I started going as fast as I could for real exercise. You know, I wanted to really sweat, really push it. I wasn’t doing this just to hang out. I was doing this as my main daily exercise, so leaning forward as fast as I could and I would bring a watch with me to time myself. And it was 43 minutes almost every time. Only if it was a really windy day did it set me back by a minute. But every time I would push as fast as I could for the entire 43 minutes and then, you know, look at the time, 43 minutes. All right. You know, I thought, well, I wonder how hard should I try to get that down? But I noticed that after doing this for six months or so, I started to get a little less enthused about it.

Derek Sivers

I started feeling like, “Oh, yeah, I guess I should go on my bike ride.” Which is ridiculous. You know, it’s this gorgeous beach in Southern California. I should be happy about this. But noticing my hesitancy one day, I thought, you know, I’m just going to go chill. I’m going to do the bike ride at like half speed. I need to just reconnect with my sense of joy around this. So I just got on the bike and I just did the bike path. And I looked up and I looked around and I looked at it. There were dolphins that day. It was like, really nice timing. Maybe they’re dolphins other days too. I just hadn’t noticed. But there were dolphins leaping in the ocean. I was like, “Oh, you almost never see that. Look at that dolphins.” And then at one point in Marina del Rey, I flew under a bunch of pelicans. I was like, “Whoa, pelicans.” And they all went right above me. I was like, “Wow.” And just as I looked up to say, wow, one of the pelicans shit in my mouth, it was like right in my mouth, like undigested or digested shellfish.

Derek Sivers

So very memorable ride. And when I was done I said, “I wonder how long that took? Probably an hour and a half.” I looked at my timer and it said 45 minutes. I was like, “Wait, no, wait.” I looked again. I was like, “Oh, my God, how the hell could that be 45 minutes, only two minutes longer than usual.” And then I realized, I mean, like not then this is talk about slow thinking. This took me days to wrap my head around that. Like so all of that red faced pushing as hard as I can and leaning forward only made a two minute gain and if I had just chilled, my legs are strong enough to push myself at a pace. They could do this without all of that red faced effort. And then it made me think metaphorically about how many other things do we do in life, like parenting, where we think like, “Oh, come on, we have to go now. You’re late. We got to go to school. You got this? How many times have I told you to to put your dishes in the sink?” And for what? Maybe it’s like the exact same result without all of that stress. So, yeah, there’s my story. I love.

Joe

I love it. And there’s a couple of things we can we can pull on there. One is. What’s the order of events? The chicken and the egg? Did you go searching for a story in your book and said, “Oh, I have this one ready?” Did you come to the idea of, “Well, I love this idea of relaxing or pressuring?” What’s your best recollection of how that came to be? That did I copy the story and retrieve it or did I need it for the book? How did you remember the origin story at all?

Derek Sivers

Oh, sorry. Oh. You mean, how did I in the first place? Or for the book? What do you mean?

Joe

Yeah. Let me be a little more eloquent there. Did that story exist somewhere in your mind or on paper, for starters, before you ever put it in the book?

Derek Sivers

Oh. I put it on my website first. I put it on my website first after I had told it to a few friends, which was after I had told it to myself in my diary. And spent a couple of days thinking about the implications of that. Then I told a couple of friends, then I posted it on my site. Then I included it in the “Hell Yeah or No” book, which was kind of a compilation of posts that already existed on my site. And then years later, Joe asked me to tell it.

Joe

Beautiful. And one more on that is when you’re thinking, I’m trying to get inside your specific way of framing your writing. At what point in that story, before, during or after does the lesson bubble to the surface? Because it’s a beautiful story without the lesson.

Derek Sivers

Oh, I guess the lesson is so obvious that I could have just said, you know. And I looked at the time, it said 45 minutes, you know, at the end I could leave people to make their own conclusions, but I was just sharing that. I don’t know. Maybe somebody wouldn’t. It did take me a little bit of time to put it together and think about the comparisons to things like. I don’t know business, programming, driving. Yeah, driving. Especially like I think about this every time you see somebody dashing in and out of the lanes in traffic and they’re going as fast as they can to try to get every little advantage over everybody. And then five minutes later, you’re sitting next to them at the stoplight, you know, And I think, yeah, that was all for nothing, wasn’t it? And how much are you stressing yourself out while I’m just sitting here in the middle lane just chilling. Just looking around. We’re all going the same speed, you know? I think it’s at a really important lesson to notice. How much we stress ourselves out for nothing.

Joe

Is there a version of the story that doesn’t involve the pelican shitting in your mouth?

Derek Sivers

Well, no. I mean, I could take that out if you’d like.

Joe

You ever consider taking it out?

Derek Sivers

No. It’s such a funny detail. Like it was that actually. You know what? That just since you’re asking and digging into it, that night I met up with friends. My girlfriend was having some friends over and that was actually the only thing I told that night. I didn’t tell the 43-45 minute story because her friends were in the in a more raucous mood and not wanting to sit down and hear Grandpa Derek tell an old story about the fire. So I said, “Guys, guess what? Pelican shit in my mouth today.” I was like, “Yeah, I was in Marina del Rey and I think the pelicans flew above me and I looked up and I said, wow out loud. And as I said, the word, well, they shit my mouth.” They’re like, “No way, dude.” You know, that was the only story that got told that night.

Joe

I love it. How do you feel about me reading an excerpt of your work?

Derek Sivers

Yeah, that’d be fun. Go for it. All right.

Joe

I think it leads to the next section of the conversation that I had in mind, which is goals shape the present, not the future. So I’ll read a section of this. This is sive.rs/goals. And you knew that. You write, “You have a goal you’ve been putting off. You want to do it someday. You’ve been meaning to take real action on it, but could use more motivation. Let it go. It’s a bad goal. If it was a great goal, you would have jumped into action already. You wouldn’t wait. Nothing would stop you. The purpose of goals is not to improve the future. The future doesn’t exist. It’s only in our imagination. All that exists is the present moment and what you do in it. A bad goal makes you say, I’m not sure how to start. A bad goal makes you say let me sleep on it. Some goals seem great. They impress your friends, satisfy an old wish or are good for you. But unless it changes your actions right now, it’s not a great goal. Find another variation that excites you.” That was edited for time. But is that the most up to date philosophy you have on goals?

Derek Sivers

Yeah, I think about that all the time. That one took so many years to learn. Take it from old Derek listeners take that one to heart. That is such a hard lesson to learn that we think that goal setting is going to somehow change the future. And it was amazing to realize that goals don’t change the future, that the only thing you can change is the present moment because the “future” put finger quotes around it is just another word for our imagination. It’s something that by definition doesn’t exist yet. And so it’s just in our head. And so the only thing that does actually exist is now and what you do with it. And so a good goal is one that changes your present actions. God, that was hard to learn. And it’s still hard to remember. So, yeah.

Joe

Thank you for sharing that insight. And I wonder, you know, if someone emails you, which you’ll be kind and get back to them even if it’s 4 to 7 days later and you will let them know that they probably ask you on a lot of occasions. One of my goals is to write a book. So to think of a real practical application of this, connect the dots for them. They say to you, “One of my goals is to write a book.” Some type of bell goes off in your brain to say, “If it really was that important, you’d be doing it.” How would it actually sound? What would you say?

Derek Sivers

What I would actually say would probably depend on what you know. I don’t do form letters as much as custom conversational replies depending on the other stuff, who I’m talking to. But yeah. I’d actually--, I’d point them to that one that you just read but also to another one. I know the sive.rs/arv, actions reveal values. Your actions reveal your true values that if you say, “I want to write a book.” And you’ve been saying that for years. I think it’s fair for your friends to say, “No, you don’t. You don’t want to write a book. If you wanted to write a book, you would write a book.” Like your actions are revealing your values. Your values are apparently that watching TV and being comfortable and being safe is more important to you than actually writing that book. If you actually wanted to write that book, if that really mattered to you, you would be writing the book right now and nothing would stop you. Not even eating, not even sleeping. You’d stay up all night. You’d skip meals to write that book, if you really wanted to write that book. And when presented with that incongruency. You have to decide what to do about that. Do you want to admit that your values are different than you were? Than you’d thought? Or finally, align your actions with your values.

Joe

It’s beautiful when you say a word that is exactly what I’m thinking about and that’s value. So I want to give you a little theory here. See how I do. I heard you recently on an interview you talk about your admiration for a writer, Mark Manson. His book, The Subtle Art of Not Giving a Fuck, I thought was fantastic. I agree with you. I also think it’s possible that marketing skewed the title away from what I felt the experience was as a reader reading it. Instead of the title being-- what it was really cool. I thought the title was really Choose Your Fucks. I thought that was the message of the book because when I read it as it was and this is all coming back to you in a moment, it made me think I was going to get into a book about not caring, but in actuality, what I took from the book was you can’t care about everything, so choose your F’s carefully. Which leads me back to you. Hey, how’s the theory for you? And how does it land with you? But be much more importantly, I’m very curious and you can go to any length of detail you want. What are your tools for choosing your fucks?

Derek Sivers

First, nice one. Nice analysis of the title, I agree. And I had never thought about that. Don’t tend to think about titles very much. I’ve known Mark since before that book. And in fact, I think for the first couple of million books, my name was on the back cover with a little testimonial quote, which I was super proud of because he asked me to write the blurb for his book and I was super proud of that. I was in a hotel in Fiji for a day and there was one of those little bookstores that only sells like ten books next to the suntan lotion. And I picked it up. I was like, “Wow, Mark’s book is here.” And I forgot that I was on the back cover. So anyway, I adore that book so much. But you’re right, it’s not about not caring about anything. Yeah, I agree. It’s about being selective. So how do you choose your fucks?

Joe

How do you do it? Let’s make it a little bit more tangible to make it less of an unfair question. Let’s start with how do you choose your fucks?

Derek Sivers

It’s the things that I can’t not do. The things that have been fascinating me almost to the point of obsession. If something’s interesting me that much I feel I need to go do it. If something’s persisted. My newest book is called “Useful Not True”, which is an idea that I have been thinking and thinking and thinking about for years. And I’ve found that it’s actually between the lines of everything else I’ve written. Is this idea of useful not true, but I’ve never explicitly stated it before. It’s just like, You know what? I need to say this. I need to dive deeper into this because it’s there. It’s persisting. So I need to do this. If you’ve been thinking for years about moving to New Mexico to a tiny home and this idea is just persisting, well then you need to go do it to see even if you get there and you’re completely disillusioned and you find out that’s not what you wanted, well, at least now you’ll know. You know that you did it unless you realize for example, that you prefer living that as just a daydream and can admit to yourself it’s probably better as a nice daydream that helps you sleep at night instead of trying to go do it. Maybe you don’t want to be disillusioned. Maybe you like the illusion. So for me, those are the things that I choose to do or the things that have been hanging around for years or like the goals thing you read make me leap out of my seat and take action because the idea is so exciting and so interesting, then whatever makes me bolt up and fills me with energy, I feel I should probably go do that now.

Joe

I’ve turned down a couple of job opportunities recently based on that metric. Right? That plus the title of your yellow book. I think if there’s something that’s holding me back and doesn’t make me want to think about it, and when I think about it, I keep coming up with the reasons not to do it. That’s been incredibly helpful. So I want to thank you for that. Then I want to ask about your turtleneck, because you were wearing a stunning blazer and turtleneck that you could have worn anything else in the world except for the continuity of our original recording. But that aside, you have a beautiful microphone. You’ve made these choices. They count as choices you’ve made when you could have made an easier, less expensive, potentially less patina filled choice. So how does that next vector fit into your choosing what’s important?

Derek Sivers

I love that you said patina and vector in the same sentence.

Joe

That’s got to count for something somewhere.

Derek Sivers

Sorry. As a writer, I always appreciate the little effort to choose the surprising word. Okay.

Joe

Why are you wearing that turtleneck?

Derek Sivers

Okay. Yo, dude, what’s up with the shirt?

Joe

I love it, by the way. And I told multiple people about it.

Derek Sivers

Well, thanks. Okay. I saw myself on stage in a video where I was wearing my usual crappy shirt and sandals, and I just said, “You know, that used to be me, but that’s not me anymore.” I feel like that’s current me dressing like old me, but I don’t feel like that represents who I am. And I was living in Oxford, England at the time, which was very close to London’s Savile Row, which is known for being the best suit makers in the world or apparently at least the most renowned. And I thought, you know, as long as I’m here, this is one of those life experiences like, “Hey, I’m in Italy. I should try Italian food.” It’s like I’m in London. I should try a suit. I’ve never had a suit before. So I did a little bit of research. There’s a fascinating YouTube channel by a guy named Hugo Jacomet called Sartorial Talks. Brilliantly produced videos, too. He’s always talking just off camera to an invisible person that I suspect is not actually there. But he is an aficionado of the craft of tailoring and fine clothing. And so I learned a lot about suits that--. It was like just learning about something you’ve never known before. You know, like I might watch a tutorial about quantum computing and another tutorial about a programming language I’ve heard about but know nothing about, and same thing where I just kind of learned about suits for a bit and learned what single breasted versus double breasted. It’s like, “Wow, I never knew this stuff.” And so Hugo Jacomet, I ended up just reaching out to him and saying, “Hey, thanks. I love your videos and I live here in London. And who do you recommend for a tailor to make me a suit?” And he said, “Oh, you should go to Michael Brown.”

Derek Sivers

He said, “Michael Brown is the best suit maker in all of London.” So I said, “All right.” I went to Michael Brown and at first Michael Brown didn’t get back to me. And Hugo Jacomet contacted Michael Brown and told him to get back to me. And so Michael Brown got back to me and I said, “I’d like you to make me a suit.” And he said, “Okay.” And I met with him and he made me the suit. And then as he was almost done making the suit, I said, “Well, what shirt am I going to wear?” And he said, “Go to John Smedley. You want the seafoam cotton rollneck.” I said, “Okay.” And I went and got one and I said, “Is this what you meant?” And he said, “There, that’s what you should wear with my suit.” So I went and got four more of these in four different colors. And I said, “So what shoes should I wear?” And he said, “You need to go to Daniel. Daniel is the best shoemaker.” He said, “I’ll tell Daniel to make you some shoes.” So thanks. It was just this idea of like, you know what? I don’t know what to wear. I’ve never put a single minute of effort into this. I know that what I’ve been wearing, it doesn’t feel like me anymore. So I like what you do. I’d like you to tell me what to wear. So now, anytime I’m in public, I wear one of my two Michael Brown suits and the shirts he told me to wear. And that’s it. Simple. Problem solved.

Joe

That’s fabulous. If someone wants to buy that turtleneck, it’s going to hurt the wallet.

Derek Sivers

I don’t know. Not so bad. No. The shirt was the cheapest part. The suit? Yes. The suit was a one time splurge. Like somebody who decides, I don’t own a watch. I don’t own a fancy car, you know? The suit was a bit of a splurge for me.

Joe

Yeah. When I think of your foray into the sartorial or whatever that cool word was, that’s culinary arts for me, right? It’s food and it’s wine, and it’s a terrific cocktail. I don’t know that I’ve ever heard you really talk about those two. Where do they kind of fall into your interest plan?

Derek Sivers

They don’t. No interest. See, good example, zero zero interest. They do not fall. I eat peanut butter and jelly sandwiches in my nice suit.

Joe

And that’s what’s interesting. Right after this, I’ll go upstairs and meet with my family and that’ll be the value proposition for me. And you don’t find that value there. And that’s why I was so curious to ask you, like now maybe we pivot just a bit to if someone were saying to you, “Well, but how do I decide like I kind of like great suits or shoes, I kind of like wine.” You say, go do it. Just that’s just follow your heart. Is it that simple?

Derek Sivers

Yeah. Whatever interests you, I mean--. Okay. For me personally. I like when something interests me intellectually so it’s part of this, “Whatever scares you, go do it.” Remember I said, whatever you’re thinking, go do it. Whatever interests you, go do it. If you follow your fascination, then it’s all just joy, you know? Let me think what I mean by this. I’m just not interested in food. Two years ago, everybody suddenly went instantly crazy about cryptocurrency, and I just wasn’t interested in it. And people were getting mad at me for not being interested in it. And right now, I’m just not interested in AI. Everybody else is freaking out about AI and upset that I’m not interested in it, but I’m just not. But I’m interested in things that they’re not interested in. Like we all just go with whatever fascinates you. And for some reason, food has never interested me. Maybe ask again in eight years and the answer might be different, but as of now I just am not interested in food. So I hope anybody listening to this. You should never cave in to social pressure to be into something.

Derek Sivers

Even if under the philosophy that if everybody is really interested in something like two years ago with cryptocurrency and right now with AI. That’s a good reason to not look into it because you know what? It’s taken care of. There are plenty of people that are are playing with crypto two years ago and playing with GPT now. Plenty of people are doing that. The world doesn’t need one more person to get into that. But say in the middle of Covid times when everybody’s just at home in their pajamas, somebody commissioning a custom tailored suit. That was fun. I was like the only guy on Savile Row during Covid lockdowns. Like I went up to Michael Brown’s office like during lockdowns, and it felt very antimemetic. That’s not why I was doing it. Of course, I told you the full story about the timing of seeing myself on stage. But yeah, you should feel free to dive into things that other people may find stupid and uninteresting. And if it just fascinates you, then that’s enough reason to go do it.

Joe

Now and in a very beautiful way That brings us to your masterpiece. I don’t know how you would mention it, but I know you’re very fond of “How to Live” this beautiful book. In some ways, our entire conversation up until this point can be a beautiful entry to the book. The first four chapters of the book are called “Be Independent, Commit, Fill Your Senses, Do Nothing.” And those are four of the 27 conflicting answers on how to live. And I think people can chart their own path. And I think that you actually lay out 27 different paths with a surprising conclusion that we won’t talk about here. What is it about this book that of all your work, really brings that smile to your face that I’ve seen every time I’ve mentioned the title to you.

Derek Sivers

Hopefully we all have something that you think is your proudest achievement in life. And for me, that book is my proudest achievement if I did nothing else with my life but write that book and then die, it would feel like a life worth livin. You know, a life well lived. It’s so unique. It’s so well written. And I say that not as a compliment to myself, but I put thousands of hours into writing those 112 pages. The rough draft was 1300 pages. And then I spent two years of full time work editing 1300 pages down to 112 pages. I sweated every word there, and I’m so proud of it. Every word is just the right word. And every sentence needs to be there. And yeah, I’m so damn proud of it. I’m proud of the writing, editing, execution. I’m proud of the whole concept, which I think is very Mischievous and wise. I’m proud of the non-explicit ending. I’m proud of the ironic title and even the color of the book. Even things like the color of the book cover is halfway in between blue and green, and I worked really hard. It took months to find the exact right shade of blue and green with, you know, asked so many people around me, “Is this blue or is this green?” They said, “Oh, that’s clearly blue.” And if everybody said it was blue, then that was not the right color. I tried another color. And if everybody said it was green, then it was not the right color. And I kept trying until I found a color that half the people I asked said it was green and half the people I asked said it was blue. And then I knew I had found the right color. I was searching for the cover that represented the ambiguity inside the book. And yeah, that’s my biggest achievement.

Joe

Now when people say to me, “What’s the most Derek Sivers thing you ever heard?” I’m going to say, “You know how he picked the color of this book.” That is such like methodical and quirky and wise and that is such a gift. I would spend more time on that if I wasn’t so gobsmacked over what I think. I heard you just say. Did you say the original book was 1300 pages down to 112?

Derek Sivers

Yeah. So I spent two years writing How to Live. With the original flash of a concept. It’s an homage to this book called “Sum” by David Eagleman. And so the original concept was to write a book like Sum. Spelled S-U-M by David Eagleman, but call it How to Live. So I had the title and the concept immediately in a flash of inspiration, basically everything but the ending, but the execution to make it happen, I knew was going to be huge because I wanted to take everything I had ever learned in my life and break it into a number of conflicting life philosophies and then have each chapter represent a congruent philosophy that was then going to conflict with every other chapter. And so to put everything you’ve ever learned in life is going to be a big job for any of us. So for me, it was two years of full time writing to put everything I had ever learned, which meant everything that was in the top of my head, of course, was the first six months, and then maybe another six months of going through every book I had ever read. Looking at all of my notes in every book I had ever read since I was a kid, rereading books I had read as a teenager to remind myself what I had learned that maybe has become subconscious, to bring it back to my consciousness, to make sure to include it. And then, of course, my notes were probably a couple thousand pages. And then when I turned it into an actual first rough draft of the book, it was 1300 pages. I would never ask anybody to read a 1300 page book. I’m not that kind of guy. So then I was like, “All right, I think I’ve put everything I’ve learned in life into this. So now I want to make it good. I want to make it dense. I want to make every word count.” So then it was two years of squeezing and chopping and just compressing it down to, like, almost poetry.

Joe

Thank you for doing that. And I mean that in the most macro sense. And maybe it’s an advertisement unwittingly for the book industry because we’ll turn around and say that a book is too expensive. We’ll say, “How could this book be this much?” And then a man like you.

Derek Sivers

15 dollars. Screw you.

Joe

$15 and a hard, beautiful cover that you signed. I hope people hear that last part and say, yeah, that may be the best dollar for dollar value going. I just have 1 or 2 other things I want to ask you, but I just want to just say this has been everything I hoped and more. Derek, man, this is a treat. This is something that’ll have me smiling after we sign off.

Derek Sivers

Thank you.

Joe

A recent listener of mine described your work as Seth Godin-ish. Now we want to be careful with the comparison is the thief of joy kind of stuff here. But I know we both mutually admire Seth. He’s been a guest. What’s your best Seth Godin story?

Derek Sivers

I hope it’s okay to tell this. He is so congruent offstage and on. So Seth and I have hung out a few times in New York City. And he is the most selfless person I know. And that’s a big statement, but even in his family. He always keeps the focus on other people. So first, let’s say notice in his writing, if you look at all of Seth Godin’s blogs, his books, his podcasts, he never talks about himself or I shouldn’t say never. Every now and then he might, for a very specific reason, tell an old story about being a camp counselor or when I was at Yoyodyne, this thing happened. But he keeps that as short as possible to make a point for the most part. Seth stays entirely focused on you, on the reader, on the listener. And when I asked him about that over a lunch one day. Privately, he told me a story that-- I’ll skip the exact details. But he said that he’s even like that in his own home. That apparently the same day that he had the biggest thing that ever happened to him business wise at his business, his wife came home and said that she had the biggest thing that ever happened to her career wise happened that day, too. And he said, “Really? Tell me about it.” And they spent the rest of the evening talking about her thing and the next day. When she asked. He said, “Well, guess what happened to me yesterday?” And only then when she asked did he tell her his thing. And my jaw dropped at that, like, wow. Like even inside his own family, his value system is such that everybody else comes first. I think that’s my most Seth Godin story.

Joe

It’s absolutely beautiful. I mean, that’s something that it starts out as this beautiful story. And then the more you think about it, it’s actionable. Like as soon as we say goodbye in a moment, I can go do that with my sister and my wife and my kids. I can take that stance and I can say, how can I not? How was your interview with Derek? No, no. How was your ride? How was the traffic? Thanks for being here. I feel like that’s super beautiful.

Joe

Yeah. So thank you for that. I feel like you have something more to say about that. Go ahead.

Derek Sivers

Well, no, I was going to say he’s a huge inspiration for me like that. He’s so congruent. That it’s easy to model. It’s good. He’s a great leader because he’s easy to follow.

Joe

His website is sive.rs because you can go there and buy beautifully bundled books. “Hell yeah or No” is my favorite. How to Live is Derek’s favorite as you heard it. So pick up both. Derek, I could ask you about a million things in closing, but I’m feeling really good about where we are. So instead of looking too far forward, I want to know what the rest of your day has in store. I told you about mine. You’re closing out here by telling us whatever you feel comfortable sharing about how life looks today in New Zealand for Derek Sivers.

Derek Sivers

Actually, my favorite days are a day like today where I woke up and within 30 minutes I’m doing this interview and now for the rest of the day I’m just going to sit down and work. My kid is with his mom today, and so I’ve got the day to myself. It’s 9h30 in the morning here. I’m probably going to spend the next 13 hours straight just writing, and I’m so looking forward to it.

Joe

And I hope this conversation gives you a little bit of energy in some form or another, because I really want to thank you for the time you invested here, man. It’s been really, really special. Thank you so much for being here.

Derek Sivers

Thanks, Joe. I love your questions and your insights. That was one of the most interesting interviews I’ve ever done. Thank you.