The Decode Project
host: Cara Ooi
intentional living, overcoming autopilot, storytelling and communication, distraction and focus
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Transcript:
Cara Ooi
Well welcome, Derek. I’m very, very excited to be talking to you today. I gave our conversation, a lot of thought ahead of time because I have read your books and I’ve consumed a lot of your work. And so I have lots of questions but am trying to think about how this applies to the podcast and how this podcast is all about change. So I am often looking for a universal framework on change. And I think what I have landed on is a lot of it is about being able to break out of the autopilot, the default, the certain patterns that we get into and we’re not always fully aware of, and learning to be intentional by building the skills and the habits and the practices, to be able to be intentional in our lives and to live according to what we really care about and what really matters. And so you have always been somebody who has been a very good example of that. And I know you have lots to say about that. So I’m hoping that can be our focus today.
Derek Sivers
Sure. In fact, we can just start right now that I think for me, it’s more about the internal rewiring of my brain. I think that’s where it feels like it starts. Is having a new perspective into something that hasn’t changed. But now I’m thinking of it in a new way, and I’ll just give the dumbest example first, that you could think of a big chocolate cupcake is yum yum yum. Or you could think of it as harming yourself. And if you suddenly look at a cupcake and think of it as self harm, then suddenly just the whole way you’re thinking about the cupcake is less appealing and the actions follow next. So to me, the change of perspective happens first, and then I take the actions that are in alignment with that perspective.
Cara Ooi
Okay. Rewiring your brain involves creating a narrative or a story or a thought that’s going to stick. And so I was actually thinking a lot about this in terms of your work in the past as a performer, and how that really drilled you and your ability to tell good stories and make stories that would stick or that would resonate with your audience. And I wonder, has that translated to your ability to make sticky stories for yourself that have made you be intentional?
Derek Sivers
Oh. Yes, I was about to say no, but yes. Ideas travel better if you can fit them in your pocket. And so often when I have an idea that I know I want to keep. But it’s complicated, I’ll even privately in my diary spend hours simplifying it. Like what’s at the essence of this? What’s an unnecessary detail? So really, what does it come down to? You know, I ask myself questions like that until. The idea is small and easy to communicate to others, and if I can communicate it quickly and easily to others, then I know that it will stick with me better.
Cara Ooi
Yeah. And that very much tracks with my experience of certain things that I’ve learned from you and that have really stuck with me. And interestingly, I had the experience because I had consumed some of your podcasts years ago. And then in knowing that I was going to be meeting with you, went back and re-listened. And so I had this very strange experience of being like, “Oh, I forgot, this is where I got that from.”
Derek Sivers
Oh cool. I love that. I just had that happen when I reread this Tony Robbins book called Awaken the Giant Within. I reread it for the first time in, Oh my God, almost 30 years. I’m 53 now, and I read that book when I was like 19 and 21 and 23. I loved that book so deeply. And now going back and reading it last year, over and over and over again, I was struck with like, “Oh, wow. That’s why I think this way, I got this from this book.”
Cara Ooi
Yeah. Well, and so to be fully transparent, I had heard you say that on some podcast, I can’t remember it. And I was having this very meta experience of, “Oh my goodness. And this is happening to me right now.” So bizarre. Okay. So yeah, I agree with that. Like the getting down to the nugget, getting down to the essentialism and the important--
Derek Sivers
Yeah. So one more idea on that is I’ll give you a real example that just happened is I just went to Dubai for my first time and had a transformative experience. Talk about change. Dubai was in my top ten list of places I never want to go in my life. I had no interest in ever going to Dubai because I had no first hand experience of it, but I’d only heard what other people told me, and I heard multiple people over the years describe Dubai as this shallow, materialistic culture that cares about nothing but shopping. And they said, “Oh, it’s like the most shallow people in the world are drawn to Dubai because they just want to shop, shop, shop. And the whole culture of the place is just about the shopping malls.” And I thought, “Oh, let’s put that at the top of the list of places I never want to go.” But I was speaking at a conference a month and a half ago, and the flight on the way back from the conference changed planes in Dubai. So I thought, you know, instead of just changing planes, I’m going to get out for just two days. I will experience Dubai for two days. And I did and I loved it. It is like the bar in Star Wars. You remember the first Star Wars where they have the bar with like everybody’s from everywhere and it’s like questionable characters, but oh my god, like the variety of people you see here.
Derek Sivers
Dubai is the bar in Star Wars, and I was so fascinated that I didn’t want to leave. I kind of want to live there now. I think it would be such a fun place to live, at least for one year. It feels just like, you know, again, the bar in Star Wars. It feels like if you lived there, you would just see all forms of life come past you to you. And I came home and I was trying to communicate this to my friends, and I noticed that I was going blah blah, blah, blah, blah, blah, for like an hour just to try to describe my feelings and my experience. And so instead I sat with my diary and I thought, okay, I’ve been boring my friends a little too much with this. How can I shorten the essence of what I loved about Dubai, and how can I make it more tellable? And so even in that case, trying to not bore my friends is another reason to shorten the story. But then yes, I find that it’s easier for me to keep an idea with me in my head and remember it if I’ve made it a more enticing story.
Cara Ooi
Mm hmm.
Derek Sivers
Yeah. Oh, I’m sorry, but the reason I brought this story up is because of change it’s one of my favorite things in the world to feel your mind change on something. And here’s this place that I had on my blacklist, and now it’s on my wish list. That’s amazing. What a cool feeling to change your mind about something. Same thing just happened literally ten days ago with the computer programming language called Python. I am fluent in a language that’s very similar to Python called Ruby, and I’ve used nothing but Ruby for 15 years. I’m kind of an expert in the programming language called Ruby. And so when anybody talked about Python, I went, “No, not interested.” Plugging my ears. I don’t want to know about Python because I use Ruby, I speak Ruby, and I was just looking at setting up a new project. And so I was evaluating like 15 different programming languages, and I was looking into each one and I looked into everything but Python. And at the end I was like, “All right, well, as long as I’m evaluating every language, I’m going to have to look at Python.” So I opened up Stupid Python and I started playing with it and I went, “Oh my God, this is gorgeous. Oh my God, I love this. Whoa, this is amazing. Oh my God, I think I love this even more than Ruby. Wow.” And so for the past 15 days I’ve been doing all my programming in Python. And once again, I felt that, you know, what was on the blacklist is now on the wish list. That’s such a nice feeling. That’s my favorite change. I think something that I previously used to be prejudiced against. Now I’m actually loving.
Cara Ooi
Okay. Well, so I’m wondering if we can talk a bit more about your thoughts on how to break out of the autopilot and how to create the conditions for being intentional?
Derek Sivers
Well, first, we don’t unless we have to, autopilot works. So usually we don’t get shaken out of our flight path unless some disaster has happened. You know, lightning hits the wing, a bird flies into the engine. Then you turn off autopilot and you pay more attention to what you need to do to change. The autopilot is smart. It’s conserving energy. It’s saying, “I don’t need to think about this. I don’t need to think about that. I’m good. I’m just going straight.” I actually just read a book by an anthropologist that pointed out that our brains use calories, and we have to be smart about where we’re going to spend our calories. And we don’t want to make our brains work too hard unless they have to. We reserve our calories for things that matter. So I think maybe we all just do this evaluation in our head about what’s worth caring about, what’s worth expending our brain calories on. And usually we don’t unless we have to.
Cara Ooi
And you’re absolutely right. So breaking out of the autopilot and being intentional takes a lot of energy. So I often talk about this idea of the compelling reason, like, as opposed to being kind of pushed into the change, something’s pulling you into it. Right? So like one thing that I often use is the big three. So the big three values that kind of dictate how you want to live your life, the type of person you want to be. You know, from hearing you talk about your work, it seems to me, and you can let me know if I’m wrong. But freedom seems to be a big one. I think fun seems to be a big one for you too. So yeah, I’m wondering if you have any thoughts on that. Like this idea of having something that you’re moving towards that makes it worth it to break out of the autopilot and to expend energy and to bike up that hill.
Derek Sivers
I often think about my values and whether I’m living according to them. Right. So if I say that freedom matters to me, well, then are my actions in alignment with that? Or am I considering buying a house? And if I say that freedom matters to me, doesn’t that go against freedom unless I want to reframe that in some way and say, “Oh, buying a house gives me the freedom to da da da da da.” But on the other hand, I could look at it and say, actually buying a house would make me feel less free. It would make me feel bound to a place, whereas I’d rather be location neutral. But if I owned a home somewhere, then I’d be a little wrongly biased in favor of going back to that place more. And maybe I want that. So I spend time in my diary asking myself things like this. Like, am I living according to my values? And if I’m not, then yeah, that disconnect that incongruency feels icky. And that’s more of how I feel. The pull of like, oh, I say that this matters to me, but then look at my actions. I’m acting against my values. And so then I feel like lightning. So I think getting to the core of something first and saying what matters to me, therefore, what’s the most direct, purest way of going for that value that matters to me, even if it’s unusual and most people would think it’s weird, I don’t care what’s the for me, the way of living most in alignment with my values or that value.
Cara Ooi
So tell me a bit more about how you actually take action on that consistently. I very clearly know what my values are, but I still find myself defaulting and not acting in alignment with that. And I think many people have that struggle, and there are lots of reasons, but I think a big part of it that we’re often not talking about is this concept of the whirlwind and just how much stuff is distracting us and keeping us exhausted, right? When you’ve got a lot of stuff going on, you’re balancing a lot.
Derek Sivers
Yeah. I’m going to tell you a tiny thing that just happened yesterday. This is going to sound surprising. One of my best friends just got out of jail, two months in jail, and we were talking yesterday. She said, “When I was in jail, I had no internet, no phone, no nothing.” And she said, “I grew to kind of like the quiet after all of the medium bombardment. Now that I’m out--.” And she even changed her phone number. She just felt like making a break with her past. It was like a dumb mistake that got her in there. And so she changed her phone number, got a new phone and got a new SIM card, new phone number. But even then, even just when narrowed down to her best friends, people keep sending her things like little messages. Check this out, check this out, check this out. And she said, “Oh God, this is too much.” She said, “I kind of feel like going back to the way things were a month ago. But I don’t want to live under a rock.” And I said, “Why not, listen to that metaphor you’re using? If you’re not being bombarded by everything, then you’re living under a rock. Like, what kind of metaphor is that?” I think seeing people who are giving in to the bombardments, that they are like a leaf blowing in the wind, that they’re just being tossed around by everybody around them, that they’re not in control of their own attention.
Derek Sivers
So to me, what you call living under a rock, I call smart to be the boss of my own attention. And of course, there’s like a thousand things out there that are always saying, “Hey, hey, hey, over here, over here. Look at me, look at me.” And I go, “No. I’m just not even tempted, I don’t care.” And she said, “Yeah, but you know. I like to use my brain.” I said, “Yeah, so you read like 12 books a year. Imagine a world where it was like, not prison. But imagine if you had that amount of detachment. Maybe you turn on your phone for 30 minutes a day, maybe ten minutes a day, just to see who called you like of your friends that reached out to you. But yet you were to read 12 really good books a year and then act on them.” And she went, “Oh, I like that.” And then she paused for a second and sorry, this is going to sound like I’m complimenting myself by telling you this. But she said, “You know, you just read that book Outlive by Peter Attia. And you took action on it.”
Derek Sivers
She said, “As we’re talking, you’re sitting there squeezing your little hand grip thing because the book you read a few weeks ago told you to do this and you took action on it. That’s something I admire about you, that that when you learn something, you take action on it.” She said, “I think most people are so bombarded with information they don’t actually act on anything. They just keep taking in more information.” So what I would recommend is rethink this idea of living under a rock and consider it as a positive, however you want to describe it to yourself. The less noise, I think of it as all as noise, so the less noise you let into your senses, the better. Then deliberately choosing what you want your inputs to be, and then most importantly, acting on the things that when you’re taking in this information, if it’s not just for entertainment, then ideally it’s for making some kind of change, even if it’s a change in how you think. And usually turning that into action means just taking that first step, which might just be sending a message, making a call, taking the first step to make something happen. My neighbor recently put her old tear down house up for sale and I thought like, “Oh, that’s a big project.” And I was like, you know what? I’m going to put in a lowball offer on that house just to see what happens.
Derek Sivers
And it was just a passing idea I had, but I was like, something in me feels like this is worth doing. This is learning experience. So the tiniest little action I took in the moment was I just called the phone number on the sign, and that got the ball rolling and everything else happened. I was reading the book Outlive by Peter Attia, and he talked about the importance of grip strength. And I just paused in that moment, went to a browser tab, searched like grip strength tools, found this captains of crush iron mine. Everybody says this is the best grip strength tool, ordered it. Click click click send. Okay, done. And I went back to the book. But it’s just like in that moment I took the action and of course the thing showed up like ten days later. But I had started the ball rolling and I’m really glad that I did that little thing instead of letting that information pass me by without acting on it. Oh, and my low ball offer was accepted on my neighbor’s house. So now I own my neighbor’s house and it’s going to be a renovation project. So this is going to be a learning experience for me.
Cara Ooi
Oh my goodness. Yeah. I often talk about the idea of the two minute rule that I got from I think that’s originally from Getting Things Done by David Allen. I mean, that’s one of those little things, especially when you’re exhausted and in the whirlwind. That’s one of those little strategies that I find it’s great to start with great low hanging fruit just by doing it and believing that it actually works because it’s so helpful, has made a huge difference for me and for many of the people I work with.
Derek Sivers
You know, I’ll tell you one more. I had just broken up from a six and a half year long relationship, and I was feeling newly free, and I was rethinking my life and what this changes, and I thought, I really want to live around the world. Like I’ve just lived right here in Los Angeles for a long time, Los Angeles and Portland, Oregon. And I want to live around the world. And so I was just kind of writing in my diary for a while about how that might look and think I’d want to start easy, you know, London, say, for example, and then get increasingly harder over the years. And as I was thinking about it, I was like, “Huh? I wonder what a flight to London costs?” So I went to the search engine. You need to enter a date. And I think this is in December. So I picked May. I was like, I don’t know, let me pick a few months out. Okay. May. And I said, oh, they need a return date. I’m like, okay, what’s six months later, okay November. So I said, “Okay, now I’ve got my fake dates entered for just my curiosity of what a round trip from Portland, Oregon to London would cost.” And oh my god, it was like only like $400 round trip. And it was like a special. And I was like, “Whoa, that’s a really good price.” And just in the moment I went, yeah, click. And I booked it just minutes after having the idea and typed in my credit card and went, “Whoa, I did it! I’m about to move to London for six months. Oh my God, I just took that little step.” Initially, that first step only takes a minute. And then the ball is rolling now. So I think it’s so important to just take that first step, even if it’s bold and audacious.
Cara Ooi
So when you were talking about this idea of your friend and the inputs and the idea of living under a rock, one thing I’ve always been super curious about is the fact that you really ask people to get in touch with you, which I’m always, whenever I hear you say that or see it somewhere, I get a little bit anxious for you. Like, how do you still carve out the space to stay focused and intentional when you also allow that amount of input?
Derek Sivers
Oh, because it’s email. Email is wonderful because it just stays there. I don’t have email on my phone. So that’s a big thing is it’s compartmentalized. It’s only on my computer. And only when I log in to a certain URL that I’ve set up. Then there are the emails that people have sent me. And yeah, I go to it when I feel like it, which is somewhere between 0 and 2 hours a day, but only when I feel like it. And sometimes I don’t look at it for a week. If I’m totally on a roll with what I’m doing, I’ll just ignore it for a week. And then after a week I’m like, yeah, I’m ready. I feel like it. And then sometimes I just feel like spending a whole day on email. So I’ll just do a week’s worth of email in six hours. But usually I think I spend maybe 30 minutes a day on average and I enjoy it. It’s sweet to see people’s questions. It’s sweet to hear from people around the world. You know, somebody who is a horse trainer in Slovenia or a person running a fishing business in Mumbai. I don’t know, I just like I just find it fascinating, the people that I hear from and then, oh my God, the huge reward comes later when I keep in touch with people. And because I ask people, “Where are you from?” And I keep it in my address book. So then later, for example, right before I went to Dubai, I said, who do I know that lives in United Arab Emirates? And I found some people that emailed me over the years and I asked one of them, I said, “All right, I’m going to be in Dubai for two days. What should I do?”
Derek Sivers
And he said, “Oh my God, you need to go to the Al Shindagha Museum. It’s the most important.” And I’m so glad he gave me that tip, because that was what I was only there for two days, and I spent one day in the Al Shindagha Museum, and I’m so glad I did. My first day in United Arab Emirates was there. I’ll tell you one other. I reached out to a guy that I had met once from Riyadh, Saudi Arabia, which is nearby, and I said, “Hey, I’m going to be in Dubai by chance. Are you going to be there or nearby or do you want to meet up?” And he said, “My friend, cancel your hotel reservation. You must stay at my home.” He said, “I won’t be there, but I have a home in Dubai. I insist you stay in my home while you’re there.” So I did. I stayed in his home in Dubai and gave me a massively different experience than if I had just been staying in some random hotel. And all of this is thanks to my open inbox. I’m so grateful for the people that I meet in my inbox. I love, love, love it. I mean, you might have seen the thing I posted six months ago about all the people I met in India. I said, “All right, I haven’t been to India for ten years. I’m going to just pick two cities. I’m going to Chennai. In Bangalore, who should I meet?”
Derek Sivers
And they were like literally 120 people that wanted to meet up. And so I had one on ones with 50 of them and met 70 more at a gathering get together, two different parties I hosted. And it was amazing to meet so many people. And I learned so much about India and Bangalore and Chennai in particular, and I just love it. I’m not a massive extrovert, I’m really quite an introvert. But meeting with all these people, it’s as fascinating as any of our usual introvert inputs, like books or videos or Ted talks or whatever. We learn this stuff in solitude, and just to sit across from any number of people that grew up somewhere far from you, or grew up with a different set of values and get to know each other, is just the greatest feeling in the world to me. Talk about change and rewiring your brain. I mean, there’s the theoretical change from reading a book and going, “That’s an interesting idea.” But to sit there and get to know somebody that grew up in Saudi Arabia with such a different set of values than you, and you’re like bridging that gap and understanding each other. And he’s saying, “So how could you leave home?” I said, “Where I grew up, everybody leaves home.” And he’s like, “Where I grew up, nobody leaves home.” You know, like to compare these things and understand each other. It’s so interesting. It’s just one of the best things for your brain. I just want to keep doing this for the rest of my life.
Cara Ooi
So I guess one thing I want to highlight is this idea of living under the rock. It sounds like that’s probably a bit too much of an extreme, whereas you don’t want to be at the other extreme of just completely being that leaf being blown in the wind. You will allow inputs into your life. But again, just in a very intentional way, it’s kind of on your own terms. It’s not set up in such a way where it’s fragmenting your attention, keeping you distracted, maybe from what you really-- just where you want to be spending your time on that day. You’re right.
Derek Sivers
You’re right. Yeah, I only have 11 people in my phone. 11 people are allowed to interrupt me. I put them in my phone on purpose. Those 11 people can interrupt me no matter what I’m in the middle of. Those are 11 people I want to interrupt me. The rest are on my computer, and I go to it when I feel like it.
Cara Ooi
Okay, so I’m curious to know if this is just a way you’ve always been or something that you’ve cultivated to create both the space to be intentional, but also the ability to-- like it seems fairly effortless for you to be intentional. Whereas for most people, I would say it requires a lot of willpower to remain in that space of intention. So let me try something. Oh, sorry.
Derek Sivers
Sorry I’ll just add one clarification. It doesn’t take any willpower to not eat broccoli if you don’t like broccoli. I hate olives. It takes me no willpower to not eat olives because I hate olives. I hate noise and drama. So the the social media noise, the noise of the news, the noise of TV has always been completely repulsive to me. It’s the last thing I want in my life. But also, you and anybody listening to this should look up a seminal article. I’ve never used that word. I’m not even sure I know what it means. Called “Maker’s schedule, Manager’s Schedule” by Paul Graham Graham. He wrote this article years ago, might even be 15 years ago, and so many people have referenced it, said it so succinctly and well that the kind of schedule that a manager needs is to stay on top of things. Who’s doing what? I need to know what’s going on. I’m a manager. I need to manage this project or I’m president. I’m presiding over this project. I need to know what’s going on. I need to be in touch. And he said, on the other hand, a maker’s schedule. It’s somebody who needs to get lost in their thought. They need to have their head down, almost like empathetically immersed in a certain mindset, trying to imagine yourself, whether it’s in some computer code or in the novel you’re writing, or trying to work out the the melodic balance of the song you’re trying to write.
Derek Sivers
You need to stay in that mindset, and you can’t suddenly have a phone going, you know, ding ding ding. You need to stay in the makers mindset. So he said these are two different things. So he said when a maker can’t understand how a manager can live like that, or a manager can’t understand how a maker could live like that, he said, understand that they they have different incentives. Managers need to stay on top of things. Makers don’t. Makers need to stay deep in things. So that was-- I thought it was a really nice way of putting it. And when I read that, it’s not like that converted me. It just gave me a way of putting it because it’s like, yes, see, I’ve been living on the maker schedule since the 80s. You know, when I was 22 years old, in 1992, I left to New York City and I went to a little cabin on the Oregon coast and spent a whole year there, cut off from the world just writing songs. And the rest of my friends were partying in New York City. I was like, nope, I want to make as much music as possible. And I think the best environment for making music would be a cabin cut off from the world, because yeah, that was before the internet. So I’ve always chosen the makers schedule.
Cara Ooi
Is there any sneaky noise for you? Right. I think there’s kind of the obvious noise, like social media is very obvious noise digging at you. But then there’s also the noise within our heads, right? Or just otherwise kind of other sneaky things that keep you from the maker’s mindset or being intentional.
Derek Sivers
Yeah, but when I find them, I usually stop what I’m doing and I turn to the diary. That’s actually one of my main things when I turn to the diary is when I feel my head is a clutter I. I open up a blank text document, I’m like, “All right, what’s going on? Why am I thinking of this? Blah blah blah. Why do I think this? I’m thinking this, I’m feeling this, blah blah blah blah. Why am I feeling that?” I’ll just fingers just flying, just kind of pouring all my thoughts out on the page where I can see them, question them, challenge them, straighten them out. Or like I said at the beginning of our conversation, make them fit into my pocket. You know, turn them into a tiny nutshell so that I can simplify it for my own sake, for my own sanity. And sometimes I just do this for half an hour until I feel like, all right. Okay. Resolved. And again, maybe I need to take a little action right now to help turn this idea into action. So, you know, tick tick tick. Send one email send. Turn it off. Back to creating, mind at peace.
Cara Ooi
Okay, so maybe if I can summarize when you notice that there’s too much noise and you pause, you notice it first of all, and then you go right to your journal and you download your thoughts so you can take a look at them. And then you check in with if this aligns with your values and if it matters to you. And then you choose that first little action and you take that first action. Is there anything I’m missing there? Are there other key habits or skills or practices that you think have really made a big difference for you?
Derek Sivers
No, but just to add one more to that one, I think things stay in your brain when they feel unresolved. If they feel conflicted or incongruent, it’s going to stick with you. And I think you usually have to work out that conflict yourself, that inner conflict of whether it’s I’m thinking this but doing that or I value this, but I’m doing that or I value these two things equally. A and B and those two things I value are in conflict. How do I resolve that? And even though I’m not a very visual person, the word perspective often comes back repeatedly because I think that imagine if you’ve got some complex object in your hand. There’s so many different ways to look at it. And so if I want to resolve something in my head, I’ll keep thinking of it until I find a perspective where it feels resolved.
Cara Ooi
Okay, so I’m going to throw a little challenge in there. Again, going back to this idea of the whirlwind, because you are, I think, unusual in terms of your ability to be intentional, like be clear on how you want to be going about your life and then actually acting on it like that’s quite rare.
Derek Sivers
And so I don’t think it’s my ability as much as my value. I just value it so highly. Yeah. If you value something highly enough, you make it happen. So I think everything I’m talking about is dead easy. It’s usually just not giving into distraction. But it’s just because I value it so highly. So I don’t think I have any special ability. Sorry to interrupt.
Cara Ooi
Well, so I mean, I both agree with you and disagree with you because I think sometimes it’s about the value not being clear or it not being compelling enough. But I also really believe that sometimes it’s just that you’re not looking at it right. Like people can have a value and completely just be so distracted away from it. And so that’s why I keep on coming back to this idea of the whirlwind. You need to have the resources and the bandwidth to be able to continue to focus on that thing, because the change is hard. It’s like that uphill path, right? Like in order to be able to push up that path on your bike, you need energy, right? And when you got maybe a storm brewing around you and you’ve got the whirlwind, right? You need those resources of energy and attention. Because I think maybe one of the reasons why we’re having a bit of a-- maybe that conversation where it’s two different cultures, we’re talking slightly different languages, is that I think you’ve been so intentional about carving out space so that you have bandwidth. I don’t know, you let me know if that’s right or not. But you’re not in this kind of frenzied state all the time, which I think a lot of people are in. And so you have created the conditions to be able to stay focused on your values.
Derek Sivers
Yeah. Because it’s my top value. You said the thing I value you highest is freedom. And I guess I’ve probably said that in the past, but it’s kind of like if you ask somebody what’s most important to you and they say, I don’t know, my car, maybe in that moment they say that they’re forgetting the importance of air and and water. So I might have said freedom in the past, but let’s say that’s like the car. It actually comes maybe fifth past some other things. But to me, one of my highest values really is learning and creating. And so I just know that the environment I need for learning and creating is an undistracted environment. And so to me, removing distractions and long periods of focus are just my highest value. I’ll organize my whole life in that way even. I mean, this is not a accident, that audience, right before we hit record, she said that she likes my background. If you’re watching the video, I’ve got these little poofy checkers behind me. It’s because I’m standing in an isolation, a sound isolation booth right now, which I got for the purpose of recording my audiobooks. It’s a recording booth, basically, so it’s completely soundproof, but I think of it as a metaphor for my ideal home. My ideal office is kind of soundproof so that the noise of the world can’t get in. This is my favorite place to be.
Cara Ooi
I’m curious to know how much of that do you think is borne from the fact that you’re an artist and the culture that you have been immersed in?
Derek Sivers
Yeah, I mean that is it. That’s valuing creating. I think of learning and creating as two sides of the coin, you know, that you learn things for the sake of creating things and create things for the sake of learning. That’s how I want to live my life. And so that’s how I’ve set up my life to live that way. And I see giving in to the noise of the world as like the saddest, worst way to live my life. But hey, let’s not forget how much I was glowing and raving about being in Dubai because it was like the bar in Star Wars. So again, that’s intentional of wanting to be in that environment of just like, give me inputs, give me stimulation, but it’s choosing it. I wouldn’t want to live in the Grand Bazaar and be there all the time, but it would be really nice to live in a quiet apartment right next to it.
Cara Ooi
Yeah, that’s a great analogy. So I think that my sense is for you, like, that was interesting. And you’re like, yeah, of course, I just want to create. That’s just that’s obvious. I think at least I can speak personally. I’ve realized I also love to create things. A little bit of backstory. I’m in a women physicians choir, and that was the first time that I’ve done anything like that since I was a kid, right? The idea of doing anything in the arts just for fun. It’s this little thing that has opened up this thing I didn’t know I really loved, which is actually creating stuff and creating stuff with other people. I love it. And so, you know, I think that’s something that is a given for you because you’re just so immersed in it. And I’m sorry, I don’t mean to put words in your mouth. Please correct me if I’m wrong, but my sense is that the world of the arts really cultivates, trains you, drills you in terms of having your focus there.
Derek Sivers
Maybe even if it didn’t. I wonder about young musicians growing up today in a world of YouTube. Sometimes I think it’s maybe just from experience, realizing I’m getting nothing done. When I just keep letting myself watch videos, I’m not making anything. It can be finding the right balance for yourself. I actually looked back at when I did the most writing in my life, and I noticed that it correlated with when I was doing the most reading. So then I realized that that there was a time in my life, just a few years ago where I was hardly reading. I read maybe three books in a year, and then I looked at the time in my life when I was doing the most writing, and it was when I was reading like 30 books a year. I went, “Wow, okay.” There’s a direct connection between how much I’m taking in and how much I’m generating, because often it’s either I’m sharing something directly that I’ve just read. You know, I read something, I say, oh my God. And so I have a way of outputting this, or I’m combining it with something else I’ve read into a new, unique combination and putting out that out there. But yeah, a lot of my writing has been sparked by what I’ve been reading, but it’s only from reading books if I just take in articles and actually podcasts.
Derek Sivers
I already say this on a podcast, but I’ve actually found for me, podcasts are about the worst way for me to take in information because I want to keep listening. So by the time the podcast is over, even if it’s a short one like Seth Godin’s Akimbo podcast, I find like the moment has passed. I didn’t have time to turn it into an actionable idea. Whereas when I’m reading a book and I come upon an idea I like, I go through and I highlight it, I underline it or circle it or whatever, and I stop. And sometimes just stand up and take action on it in that moment. Or I know that my system I have in place is that when I’m done with a book, I go back and put all of my highlights into a text file. So that’s what you see on my website. If you go to sive.rs/book, you will see the list of almost 400 books I’ve read since 2007. 2007 is when I started taking notes on the books I was reading, as I’m describing, like underlining my favorite sentences or circling my favorite ideas, and then putting them either verbatim or reworded into my own words in a text file.
Derek Sivers
And I was doing that for myself for a few years before I started sharing them on my website. But the purpose of doing that is so that all those interesting ideas I came across while reading the book, if I didn’t take action on them in that moment, well, then I sure do. In the moment when I’m putting them into the text file afterwards, or if it needs further reflection. Now I don’t need to read that book again. I can just turn to my notes on that book again and go think more deeply about the ideas in it, and then that might turn to action in the future. But yeah, so you’ve got to--. Sorry. So back to the artist thing. You just got to learn from experience what works for you, what environment helps you be who you want to be? Maybe for some people, consuming tons of YouTube videos does work for them. Maybe it’s a bunch of articles, maybe it’s swiping on Instagram a lot actually works for some people. It doesn’t work for me. For me, the most productive thing I’ve found are reading books, keeping my notes, and then writing about what I’ve learned.
Cara Ooi
Okay, another question I really was curious about. And this one might not be fair, because it’s asking you to speak to an experience that I don’t think you that you have. But let’s say you had not created the conditions in your life, and you were very much in the whirlwind. And maybe that whirlwind wasn’t just stuff that was clearly stuff you didn’t want in your life. It was stuff that was kind of complicated, right? Like maybe there were other responsibilities that were tied to things that you really value. Maybe to give an example, my husband’s a physician, and he knows that he has too much on his plate. He’s an ICU physician, and his schedule is crazy, but it’s also really tied to him being a helper. And so that’s a hard thing to reconcile. So sorry tangent, but let’s say--.
Derek Sivers
That actually really helped because I didn’t know what you were talking about. I was like, are we just talking about Instagram? So no, you’re talking about on a deeper level of like, yeah.
Cara Ooi
Well, and I would say the other part of my whirlwind and for a lot of people I think is balancing all of the family stuff and just everything. Right. It’s a lot to juggle. So let’s say you had less bandwidth than you have right now. What would you say are the key things? Let’s say you only had five minutes a day to be in your sound booth. What would you do?
Derek Sivers
Okay, I have been in that situation and I do have a kid, and I ran my company called CD Baby for ten years that had 85 employees in a physical warehouse shipping things every day. And I did spend five years just in the whirlwind of showing up to the office. And there I was, surrounded by everybody’s questions and problems all day. And I did that for about five years, and that’s when I felt the pain of getting nothing done. I felt like I might as well just show up to the office, just put a chair in the hallway and just sit here and just answer questions all day long, because that’s all I’m doing is just dealing with other people’s questions all day. I’m doing nothing for myself. I’m getting nothing done. I’m not making anything. I’m not developing anything. And like I was still the sole programmer. I didn’t hire programmers. I enjoyed doing the programming myself. So I was like, the website’s not advancing. The business is not growing. Oh, sorry. The business was growing, but the business is not, let’s say, developing, adding any new services or improving anything. Because I’m just sitting here answering people’s questions all day. So that’s when I hit my breaking point in 2004. That’s where I hit my breaking point. I said, “Okay, I can’t keep doing this. I need to make a change.” And so that was then it was time for some serious journaling to say like, this is unsustainable.
Derek Sivers
I’m miserable. This is bad for the world. And that’s where I kind of started thinking of those slogans we’ve heard, like, only do what only you can do. So I thought, really, do I need to be the one responding to all these questions? And does it need to be real time? Is there any better solution to this? And so yeah, I put a lot of work. It was like six months of hard work to transform the way my company was working so that people didn’t send all their questions to me. And then I clicked into more of a maker’s schedule. You know, I set up the system. It took months to make it happen, set up the system so that things ran without me. And then I was free. I started working from home, even though the office was just five minutes away. I started working from home so that I could just have this like 12 hours of solitude. And I thrived so much in that environment that I just made that a permanent change. By the way, another book that’s really good on this subject is Tim Ferriss first book called “The Four Hour Workweek”. He talks a lot about how to organize your life with real, concrete good tips so that things happen without you needing to be on top of them yourself. So if you want some good, concrete tips, listeners go read or reread The Four Hour Workweek. It does address that a lot.
Cara Ooi
Agreed. Okay. So not asking you to distill Tim Ferriss entire book, but what were the strategies that made the biggest difference for you?
Derek Sivers
Okay, well. Tim’s book, I read it, it was preaching to the converted already. I read it in my very last, or it was released in the very last year of CD Baby. For me, I did CD Baby for ten years, and I sold the company in 2008, and that book came out in 2007. So I was already living its message when it was released. That’s how we met, actually. I read his book, contacted him saying, “Oh my God, this is great, dude. I’m living what you’re describing.” And he said, “Cool, let’s meet.” And so that’s when we met and became friends. In 2007, 2008, I was living in San Francisco for a bit, but so it was some things like, well, first, hiring help. Even if you’re a solo freelancer, hire an assistant, get somebody to help you make it worth it. And then he talks about a lot about how to delegate setting guidelines, setting rules, saying like, if you can handle a problem for less than $500 or set your budget at whatever it is, do it yourself. You don’t need to ask me. Ask me if it’s over $500. If it’s under $500, I’m giving you advance permission to take care of it.
Derek Sivers
And then even learning how to communicate your thought process. So if somebody sends something your way and says you need to decide this, okay, well then you do decide it. But you note your philosophical process or your decision making process when making this decision. And then you share that with your assistant. See, okay, here’s how to decide this problem in the future so that if this kind of thing comes up ever again, you won’t need to send this to me. You know, if a b, then l, m, n, o, p if c, d then x, y, z. You know, like you could kind of set out these rules to say this is how I think of it. So now therefore this is how you can think of it. And you don’t need to ask me because this is my rule making process or this is my decision process sharing that with assistants. So it’s empowering other people to take care of things for you. Let’s go straight to death. Why don’t we I think about this as preparing for death. I think about someday soon I’m going to die. I’m in the last third of my life now. Probably. Well, statistically.
Cara Ooi
Well now you’ve read Outlive, so maybe not.
Derek Sivers
Yeah, right. But I’m going to assume I’m in the last third of my life. It’s important for me to keep remembering that these things don’t have to be me. If I think this needs to get done, well, then, if I want to be at peace on my deathbed instead of in panic, I need to make sure that all these things are getting done by other people besides me. I want to make myself unnecessary sooner instead of too late. And so getting yourself out of the whirlwind sooner it’s good just preparation for life to make yourself unnecessary, and it’s helping others take on more responsibility. It’s helping others grow. It’s helping in any organization. It’s helping other people step up and grow instead of you holding on to too much responsibility yourself. Yeah, it’s just morally and practically a good thing to prioritize that if you’re finding you’re in a whirlwind, that too many things are coming your way, I think it just helps to say, “Okay, it’s time that I share this responsibility.” Help others step up. Help them learn. Help share my philosophical process, help make things their job instead of my job, and try to make yourself unnecessary. But then you got to have, of course, a value system that wants that. So some people really like being in the middle of things that what they actually want, even if they listen to an interview like this, or read a book that says they should be on a maker’s schedule, maybe they just really like being on the manager’s schedule. They like being in the middle of things. It’s exciting. You got to start there to see if this is what you really want.
Cara Ooi
So I’m just aware of the time and I don’t want to take up too much of your time. So I’m just wondering I always like to ask a few final questions. The first question I wanted to ask is, what are the top three things that you’ve learned about change?
Derek Sivers
Oh, I guess we talked about some of them here, maybe all of them. Number one, I think it starts with rewiring your brain in the moment to first think of something differently. You just feel that perspective change, looking at something from a new angle. And this happens to us all the time. But I think change starts with that. Change starts with changing your mind first and then making a real change starts with taking an action in that moment so that it doesn’t pass you by. Don’t let it go before taking some kind of concrete action on it, whatever that new change may be. And then we’re social creatures, so sharing that change with friends or family, telling people. Saying, you know, I’m thinking about this differently. I used to think this, but now I think that. And so I think those are the three things. It starts with changing your mind about how you’re thinking about something, taking any kind of first little action to put something in. So it turns into reality. It doesn’t pass you by. And then sharing it socially to help hold you to it and make it your new self-identity. Self-identity matters a lot.
Cara Ooi
Okay. And then the other question I always like to ask at the end maps on to what you just said, which is, again, because it’s all about taking that first step. What would the first step, two minute step be that you recommend for for those listening right after they listen to this podcast?
Derek Sivers
Oh, like a specific thing right now? Think of something in your life where you are not in total control. Where you feel like well, of course, in a perfect world, I would have total control of that, but I don’t. So my challenge is then to challenge that idea, to realize that you do have control in those situations where you don’t. And instead of saying, can I shut out that bit of whirlwind? The answer is already yes. So then ask yourself, how can I shut out that bit of whirlwind that feels out of my control, therefore giving myself control over it? And then do that first step to take action that direction and make it your new habit. Practice.
Cara Ooi
Love it. So notice the can’t get out a piece of paper. Decide that it’s possible and then start working on the how.
Derek Sivers
Yeah, I still wrestle with this almost weekly. I still encounter things that I feel are out of my control, and I have to stop and go, “Wait, really? I’m acting like, really? Well, then if it’s not in my control, whose control is it in? Really? Am I really the object of that verb?” And I just stop and go, “Why did I, why am I acting like I’m the the victim here? Hold on. Let me flip that stick.” And yeah, I still have to reframe my situations and think of them in a more empowering way, very deliberately, and then take action that direction. Sometimes it upsets people. So yeah, we all have these things in our lives everyday that you feel are out of your control. It’s nice to remind yourself that these things are in your control.
Cara Ooi
Yes, I often have to have that mindset shift from that victim mindset to well, how am I in control? But also how is this potentially this constraint to a gift? That’s another one I tend to go to. All right. Well thank you, Derek. Any final parting words before we finish up for the day?
Derek Sivers
No thanks for having me. That was a fun deep dive conversation. I love your questions and thanks for pushing me on some of those things. And thanks for letting me interrupt. To clarify, I felt a little rude doing it, so thanks for letting me interrupt at times and clarifying. Yeah. Thanks. Anyone listening, go say hello. Send me an email. Introduce yourself. As you can tell, I love it.
Cara Ooi
I will be sure to put all of that in the show notes. So thanks. Thank you very much Derek.
Derek Sivers
All right. Okay. Thank you so much.