Weekend University
host: Niall McKeever
Great conversation about skepticism, debugging, rebelling against yourself, going against your impulses, questioning.
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Transcript:
Niall
Okay, Derek, welcome to the show.
Derek Sivers
Thanks Niall. It’s finally great to finally talk with you. We’ve been emailing for 10 years and I’ve been following your stuff for a long time and checking in on you. So now after 10 years of emailing, we’re finally speaking.
Niall
Yeah, Derek’s act of public service is that he responds to every email, so if you email him he will respond to you. I probably shouldn’t say at the start of the interview.
Derek Sivers
I encourage it. In fact, I think it’s the big reason I do podcasts like this. I’m not here to promote anything. I’m here as a magnet to find the other cool people spread around the world so that they contact me and we get to know each other.
Niall
Well, your most recent book is titled Useful Not True, so to get started Derek, can you just give us your definitions of both of those terms, useful and true, please.
Derek Sivers
Yeah, I had the title first because it was something I’ve been wanting to communicate for a while about choosing what we believe because it’s useful, not because it’s necessarily true. But of course, to write a book like that, I thought, “Oh, shit, now I have to define what I mean by true. What do I mean by true?” So the best I’ve got is that when I say true, it means necessarily, absolutely, objectively true for everyone, everywhere, always. The reason to set that definition so high is because once you consider something to be true, then you think it’s a fact and that’s that. It’s closed and you will never question it because it’s just true. As you can imagine, I’m trying to suggest that we do less of that - that we define less things as necessarily true so that we can keep questioning them.
Derek Sivers
“Useful” is whatever helps you do what you need to do, be who you want to be or just to feel at peace.
Niall
How do you hope that your readers are going to be different after having read “Useful Not True”?
Derek Sivers
More skeptical. Healthy skepticism. Ultimately, it’s a book about skepticism. It’s a book about taking the stories you’ve told yourself about your past, about who you are, about the way the world is, and opening them up for questioning if you find that they’re not serving you. So if you feel like, “Well, I’m just bad at this. I’m not the kind of person who has good things happen to me.” That might not be true. It feels true, but it’s healthy to look at that and say, “Well, hold on a second. Based on what?” Because there might be somebody else in your high school that would say, “Oh man, you were always the super achiever. You’re always great at everything you do.” You go, “Wait, what? No, I feel like a loser inside.” Somebody else might think that you’re the winner. Even in particular situations, you might look at an ex that dumped you and find out that your ex thinks that you dumped them. There’s so many things, whether it’s about our past or about the present situation. You might look at a current situation you’re in and say, “Oh, there’s just no way to do this. That’s never going to work.” You can just reframe this and say, “Wait, hold on. That’s not true. That’s only one way of looking at it. It’s not necessarily true.” This is where so many extremely successful super achievers find their edge is by looking at a situation that others would say is a dead end. They say, “Hmm, actually, I think there’s a trap door in here somewhere and we can get out and I can do this.” That starts with skepticism. That starts with doubting your first impression that is usually a pretty limiting belief.
Niall
Wow. Well yeah, like the big thing I’ve got from it is that it’s given me a lot more flexibility about how I look at my beliefs and you talk in the book, you give a really interesting story about how the past is not necessarily true and you talk about a car accident you were involved in at quite a young age that weighed on you for probably 10 or 15 years or so and then you met the woman. Can you tell us about the story, Derek, and its relevance to what we’re talking about?
Derek Sivers
I mean, it’s just one tiny example of the kind of thing we’re talking about is when I was a teenager, just a couple months before I went off to college. I was in a car crash. As they took me away and they took away the other woman in the other car, somebody told me the next day, they said, “Oh yeah, that woman you hit, you broke her spine. She’s never going to walk again.” I’m like, “Whoa, whoa.” It’s weighed so heavy on me for so many years that 18 years later when I was mid 30s, I went back to my little hometown of Hinsdale, Illinois, USA, and I found her in the phone book and showed up at her door and she’s walking just fine. I had completely misunderstood or somebody just miscommunicated it to me. They misunderstood and I held onto this big heavy story for 18 years that was based on one little bit of misinformation. Then as I was talking with her and I apologized for hitting her, she said, “No, sweetie, you didn’t hit me. I hit you. I was eating and distracted while driving. I’m the one that swerved into your lane.” I went, “What? No.” For 18 years, both of us thought that we caused the accident. To me, this is just an example that I’ll bet everyone listening to this has an example in your life of some story that you’re holding onto about the past that’s based on one perspective of one little bit of information that might not have even been correct, but you’re holding onto it as the story of the past, which might be weighing you down.
Niall
That must have been such a weight lifted off your shoulders to realize that you hadn’t actually paralyzed that woman. You must have felt so light after that.
Derek Sivers
Well, I think of everything pretty metaphorically. So it then immediately makes me question things like I always thought that I was just not attractive. I’m not an attractive person. There are these guys that are hot that all the women want and I’m just not one of them. This to me seems to just be a true fact. Here’s my height, here’s my age, here’s my attractiveness level. That’s just a fact. It was based on two exes that we had a great relationship as people. I just loved her and she loved me for who I am, but she just wasn’t attracted to me, and that’s that. So therefore I took it as a fact about me. I’m just not attractive. This seemed to me to just be, like I said, one of the basic fundamental things of who I am. Here’s my name, here’s my attractiveness level. It was only really just a few years ago in my fifties that I went, “Oh, wait, hold on. That’s not true. There’s actually a whole bunch of counter-evidence.” I’d been holding onto this mis-categorization based on two little data points that were outliers. Again, I think all of us have these beliefs that we hold and we just think of them as just true - that’s just a fact. That’s why the whole point of the book is to make you question all these things that you consider true. To say, “Look, unless it’s absolutely, necessarily, objectively, observably true for everyone, everywhere, always, and like any creature or machine could observe it and agree, if it’s anything short of that, then it’s not necessarily true and should be opened up and questioned.”
Niall
For sure, for sure. It reminds me of a guy, Bruce Lipton. He talks a lot about the biology of belief. One of his key points is that most of our beliefs form before the age of seven. Those first seven years, your unconscious is just like a sponge and you’re just absorbing everything in your environment. So all these things get into your sort of into your subconscious mind before you have the ability to critically assess them and actually assess, is this useful, is this true or is this just something that someone’s told me? So these things, they’re like a bug in our operating system and they affect us for most of our lives. What you’ve done with this book is you’re essentially giving people an operating manual for sort of like looking under the hood of your mind and saying “Does this actually serve me or is this something that is a bug?” If it is a bug you provided steps there for debugging, exactly. You talk as well in the book, there was a sentence that I wrote down, it was “Belief cause emotions, emotions cause actions. Choose the beliefs that lead to the actions that you want.” Can you maybe expand on that a little bit and have you any comments there?
Derek Sivers
Yeah. It’s a tougher one to explain, but it’s really profound and it’s really important. Your actions — what you choose to do, whether you choose to jump into an opportunity or let it pass or bounce out of bed or sleep in — are initially based on your emotions. Whether you’re feeling overwhelmed or if you’re feeling psyched, that’s an emotion. But even that emotion comes from the way that you’re seeing something.
Derek Sivers
If you see a project as overwhelming, (“Oh my God!”), then the way you’re representing it in your head is just a huge thing. Then it feels daunting because you’re seeing it in a certain way, which then makes you feel tired, and the action you take is nothing. You sit on the couch and play video games instead because the idea of dealing with that project is too daunting. But that all starts with how you’re choosing to see it. It was amazing to realize that your belief about something like, “I can’t do this,” or “This is easy,” those two opposing beliefs about the same thing can lead you to feel differently about it, which leads to the different actions about it. It’s amazing to realize that that initial belief or perspective is completely up to you. You have a default that you impulse your way into by unintentionally thinking of something in the default initial impulse way, but you can consider other ways to see it.
Derek Sivers
Like, I can’t even imagine right now the desire to be Prime Minister of New Zealand. No way. It’s out of my realm. I could never do that. But somebody right now could say, “Well, actually, Derek, you’re a New Zealand citizen, and you’ve got a good sense of this and that. You know, it’s not that hard of a job. It’s the same number of hours you spend doing the things you’re currently doing. It’s the same nine to five hours, but you’d be doing a greater service.” Somebody could tell you a thought process that could make you go, ”Oh, wow, I could do this thing,“ and suddenly take the actions and seven years later you’re Prime Minister of New Zealand. It just starts as a different thought process. That initial change in belief, a change in perspective, a change of the way you look at something completely affects your emotions about it, and your emotions are what affect your actions that you take.
Niall
That’s very well explained.
Niall
And so, you spent how many years writing Useful Not True? What, five?
Derek Sivers
Oh, no, this one? Two years. I was sitting on the idea for a couple years. It was underlying the other stuff I’ve said. So, for example, in some of my previous books, I said things like, ”Business is not about money. Business is a place where you get to set all the rules and you make your own little utopia.“ Or, in a later book, I said, ”I’ve decided that everything is my fault. When I think of the world as other people’s fault and I think of myself as a victim, it makes me feel helpless. But if I think that everything is my fault, then this feels like something I can do something about.“
Derek Sivers
So, over and over again in the past when I’ve shared my deliberate beliefs on something, people say, ”Well, that’s not true.“ I didn’t say it was true. I said I’m choosing this perspective to think of business as a place to be generous, to think of the world as my fault. For me, this puts me into a useful mindset that helps me take the kinds of actions I want to take. I never said it was true. What the fuck is true anyway? I’m clapping my hands. That’s true. But a perspective? A perspective is never true. It’s always just one way of looking at it.
Derek Sivers
So, this was always underlying the other things I’ve written over the years. As people kept poking me on it, I thought, ”You know, I just need to address this subject directly. So, I’m going to write a book called Useful Not True.“ But then it took, yeah, two and a half, not five, but two and a half years of work to write it because I had to go read the Bible. I had to read ten books about religion. I contacted a philosophy professor and asked her, ”What is this way of thinking?“ And she said, ”I think you’re describing pragmatism.“ So, I went and read seven books on pragmatism and found out, no, it’s actually somewhat similar to nihilism. So, I read a couple books about nihilism and read a couple books about skepticism and beliefs.
Derek Sivers
You emailed me last week about a book that I almost read. What was it, Donald? Do you remember his name? Yeah, The Case Against Reality. I heard a brief little synopsis of The Case Against Reality and I went, ”Oh, this is a good idea. I want to include this in my Useful Not True book.“ So, I started reading it, but it was honestly kind of at the 11th hour as I was almost done writing the book and I said, ”Ah, that’s too much.“ I think that The Case Against Reality argument might get people to dismiss the other things I’m saying because I think what Donald Hoffman is saying is like, ”Actually, it’s just your entire perception of things is all just synapses connecting to your brain. It’s not necessarily the reality.“ And I’m like, ”Oh, that’s too far. We all draw the line somewhere.“ So, I thought, ”Well, I’m going to draw the line a little back from that point.“ But it was fun for two and a half years learning all about the subject of beliefs, realities, perceptions, how they affect our actions, pragmatism, skepticism, all of that.
Niall
The other story that I think was absolutely just incredible from that book was your order confirmation email. Can you just give us that, just that, a brief overview of what that was and how you set that up.
Derek Sivers
When I first built cdbaby.com, my little online record store, like anybody would, I just had a default email confirmation. I was building the software from scratch anyway. I wasn’t using some prepackaged e-commerce software. So, I had to write the email to let the person know that your order has been received, your order has been shipped. The initial one just said, ”Okay, your order has been shipped today. Thank you.“ That’s it. I thought I can do better than that. Like, come on. It’s a record store. Why spread generic notifications when you could spread something that makes people smile or at least do a double take or something a little weird? So, in 10 minutes, I wrote this quick little email that went, ”Your order has been picked with satin gloves from and placed into a gold-lined pillow and sent on our private jet to you on this day. Your picture is on our wall as customer of the year. A whole crowd gathered around and waved bon voyage to your CD on its way to you this day, the 17th of July. We hope you had a good time shopping at cdbaby.com. We’re exhausted but can’t wait to see you again.“ Something like that. It was just stupid. It was just being silly in 10 minutes. But that one email reached so many people. A few hundred people a day buy a CD from me and a few hundred people a day got that email. A lot of people shared it and spread it and posted it on their blogs and shared it on social media and sent it to their friends. Seth Godin even put it in a book and talked about it. I think there have been a couple books now that quoted that email. I’d find that customers were coming to CD Baby because they heard of CD Baby - because of that email that had been shared around. I thought, ”Wow, that was a good use of my 10 minutes.“
Derek Sivers
It comes from asking yourself how you want it to be. Right before we hit record, you said that I write very succinctly. And, yeah, I read a lot of books that were just too verbose - 300-page books that really could have been 20 pages. And that pissed me off so much. I thought that’s not how the world should be. We should write more succinctly. Skip the fluff. Get to the point. So it’s not saying that everybody needs to start writing silly things. It’s just you look at the way things are and you say, ”Well, in a perfect world, how would I want them to be?“
Niall
Definitely. And so we’re talking there about your company CD Baby which you spent over a decade building. How long did that take roughly? About 10 years. And then you sold that, you became like mega multi multi millionaire and then you gave everything away to charity.
Derek Sivers
Well, wait, sorry. Tiny nitpick. I actually set it up so that the multi-millions never touched my hands. I transferred the ownership of my company into a charitable trust first before I sold it, so that when the company was sold, the money went directly into a charitable trust. I didn’t want it to ever touch my hands.
Niall
Okay, okay. Yeah, that’s quite unconventional to say the least. But then what I find interesting about your story Derek is that you were like gearing up to go like right, I’m going to Silicon Valley, I’m going to start another company, I’m going to be like this mega successful serial entrepreneur and then you’re like actually hold on. Do I really want that? You know, and then you change direction. Can you tell us about this period in your life?
Derek Sivers
Yeah. I don’t talk about that much, but it just seemed like the obvious thing to do. I’m selling my company. I’ve got a whole bunch of other ideas I want to do. Literally the next morning after selling my company, I woke up with my next big idea that I was so psyched about, and I spent months building it. But then I had to catch myself realizing that it sounded like I was going to stay on the same trajectory - that if I were to sell this company and then build the next one, well, I’d be swapping out the name above my forehead, you know, the name of the company. But really my life would be exactly the same. I’d be throwing myself into yet another thing and the trajectory would keep going exactly as it was. By my values, I thought yes, that would make more money, but it seems like it would lead to a less interesting life. I want a full life. When I’m on my deathbed, I want to be looking back at, wow, all the things I did, not just “How much did I stockpile? How much did I make the numbers go up?” I want to think of a rich, full life having done many things, tried many different approaches to life, seen the world from many different angles. So I halted it. I stopped doing that new startup idea. I did not move to San Francisco to do to dive deeper into the world I was already in. Instead, I just went and deliberately shook things up and just started saying yes to everything I used to say no to. Started saying no to everything I used to say yes to. I moved far away. I tried moving to China, but my girlfriend at the time hated it. So we compromised and moved to Singapore, lived in Singapore, and that’s where my kid was born and definitely shook up my world.
Niall
What was it like to go through a period of your life where you were basically going against your instincts, your impulses, going against the things that had served you so well until that point? What was that like?
Derek Sivers
Nobody’s ever asked me that before. That’s a fun question.
Derek Sivers
It felt great. It’s a rebellion that is a rebellion against myself. It’s like, ”Fuck you, Instincts. You can’t tell me what to do.“ Yeah, everything is telling me to say yes to this invitation I just received, so I’m going to say no. It’s mischievous. It’s day-to-day rebellion. ”Hey, this woman is really attracted to me, and I’m just not attracted to her. So maybe I’ll go for it.“ At every given moment, doing the thing that my instinct is telling me not to do, it’s fun. Also makes you realize that there’s no right or wrong answer. There’s no good or bad outcome, even. It’s just different. It was wonderful to change my daily decisions and outcomes. Like when somebody decides to travel to Africa or Cambodia: you’re doing it to shake up your day. And so I was doing it just with my daily decisions.
Niall
We’re not talking about minor things here. You got married.
Derek Sivers
Yeah, I know it makes me sound like an idiot, but it was a certain situation. We’d been dating for six months, and she said that her parents were insisting that we be married if she was going to travel with me. My initial instinct was, ”What? Hell no, I’m never getting married again. I made that mistake once. I never want to do that again.“ It’s like, ”Hmm, yeah, fuck you, instinct. You can’t tell me what to do. All right, I’ll do it.“ So, yeah, I did it. Got married. And it was horrible.
Niall
Well, you have to try these things to know. One of the important takeaways from this is that this is very context-dependent. There are times in life where that going against your impulses is the best thing you could do, if things might not have been going well for you up until that point. But there’s other times where you got to trust your gut too. Do you want to say a bit more about that?
Derek Sivers
Think about what you just said, that any approach you could take towards life or anything is an approach for a purpose, for an outcome. If somebody says, ”You should follow your holy book exactly. You should do exactly what it says. You should not think that you are anything special. The recipe for life has been solved. Just follow the book.“ That is really good advice for a certain outcome. If you want this kind of life, then that is the approach for that kind of life. If you want a life of chaos and uncertainty, well, then there’s a different approach to life you could take that would get you that kind of outcome, a different set of values and rules that you would follow for that outcome. So whenever some guru is preaching publicly saying, ”Here’s how to live,“ they’re saying they have the answer. But what’s left out of that sentence is it’s the answer for this kind of outcome, for this destination. The way to get to the top of the mountain is to keep going up at every turn. But that’s only if you want to get to the top of the mountain. If you want to swim to the bottom of the ocean, it’s a different set of instructions. If you want to get lost in the jungle, it’s a different set of instructions. So you have to filter everything you hear from the variety of gurus through this understanding that what they’re saying is the right answer is only the right answer for that purpose or destination.
Niall
For sure. I like what you said there. Just you were saying about here’s how to live and then you pointed at the camera. It was almost like you should have titled the book How to Live, Here’s How to Live and then how to picture yourself like Uncle Sam’s pointing.
Derek Sivers
Yeah, that would never be misunderstood. Never.
Niall
So the example that came to mind for me, Derek, whenever I was thinking about this was one of your most famous blog posts is “Hell Yeah or No”. But then you’ve also got an interesting story about saying yes to a circus gig early on in your career that led to you being in the circus for I think 10 years as well. And it’s like there’s a time and a place for both of these philosophies. Maybe just share a little bit about, I suppose, yeah, the benefit, maybe just quickly do like a brief sort of like the benefits of the yes to everything. And then the take it the other way about the hell yeah or no. Cause this is sort of like how to live. This is the way how to live is kind of right. You know, you’re saying this is way you should live, but then this is the opposite way too.
Derek Sivers
Yeah. It’s different approaches for different situations, right? So if you were at the start of your career, maybe you just graduated out of university, you don’t know what’s next, well, then a really good strategy for you is to say yes to everything. Because like lottery tickets, you don’t know what random numbers are going to be the winning ticket for you. So you say yes to everything. The more lottery tickets, the better. Then when something starts rewarding you in an outsized way, then you need to start saying no to all the other things and follow the thing that’s most rewarding, whether it’s financial or emotional or creatively rewarding. Then you double down on that. At a certain point, if you get overwhelmed with too many requests and too many options and you find yourself spread too thin from saying a half-hearted yes to too many things, then a better technique is to raise the bar all the way up and say, ”From now on, if I’m feeling anything less than hell yeah to something. If I’m anything less than completely psyched, I’m going to say no by default to everything.“ So literally everything anyone asks you to do, the answer is no, unless you’re feeling, ”OMFG, yes. Hell yeah.“ Then you say yes to that rare occasional thing. What happens then is it leaves space in your life for you to throw yourself all the way in to that occasional “hell yeah” thing and just let go of everything else.
Derek Sivers
But notice that these are two completely conflicting approaches. When I wrote about hell yeah or no, unfortunately Tim Ferriss liked it because he was feeling overwhelmed at that stage in his life, so he blogged about it and mentioned it repeatedly and a lot of people that follow him said, ”Hey, I heard about hell yeah or no. I’m using this in everything in my life. I’m applying it to everything. I’m fresh out of school and I’m getting all these job offers and none of them make me say hell yeah, so I’m saying no to everything.“ I say, ”No, you’ve missed the point. It was a tool for a certain situation. It is a way of handling overwhelm. When you are drowning in good options, you need to raise the bar to only say yes to a great option. But you can’t say that this is the hammer that I’m going to use on everything in your life now. That’s an unwise use of it. So whatever. Maybe they’ll find out the hard way.
Niall
Tim’s new book is actually going to be on the power of now. You’ve probably spawned that maybe a couple or a decade ago.
Niall
Another thing in the book, you tell the story of Igor Stravinsky in the 70s in LA and I think someone asks him what’s the best instrument or whatever and then he gives a whole spiel about the different instruments and how they’re actually like philosophies. Can you tell us about this metaphor and its relevance to what we’re talking about?
Derek Sivers
Sure. Could you tell that I made up that story or did it sound real? You’re the first person to ask specifically about that story. So you’re the first person to crack the news that no, I just made that whole thing up. I made it sound real. I quoted the date that it happened and the biographer that wrote it. But no, I just made the whole thing up.
Derek Sivers
I made up that story to explain the ending of my last book called How to Live where I just showed a picture of the orchestra seating chart with no explanation. I thought it needs a little more explanation. It applies to the useful not true theme, which is that each instrument in the orchestra is not the one and only true right correct instrument. Nobody would tell you, “You know what? Never mind all these others. The clarinet is the best instrument for everyone everywhere always.” No, I mean, maybe there’s a clarinetist who believes the clarinet is the best instrument. But come on, nobody really thinks that it’s the instrument for everyone everywhere always. But when it comes to life philosophies or religions, there are a lot of people, often millions of people who believe, “Nope, this is the best instrument for everyone everywhere always.” I was using the orchestra metaphor to say that each instrument has its wonderful qualities. You use it at certain times in the music. There are times in the music when you want to harp and times in the music where you want the trumpets with the little mutes in them with that very reedy sound. So same with life philosophies, you use them at times in your life for a certain purpose or a certain color in your life. I need a little more hedonism right now. I need a little more discipline right now. So we use them. Neither one is the right answer for everyone everywhere always. But it’s what you needed at this moment. So I made up a story about Stravinsky saying this because I thought if Stravinsky said it, people would pay more attention.
Niall
It works. And which philosophy are you finding most relevant and applicable to your current life situation?
Derek Sivers
I don’t know. I think it’s changing a few times a day. There’s no big overarching approach to life I’m taking right now. There’s a certain approach that I use to do the things I know I need to do but don’t necessarily want to do. Like lifting weights and not eating the cupcake. There’s a certain approach to life I’m taking to be fully present with my kid. These are completely unrelated, well not completely, somewhat unrelated philosophies, but I use them at different times of the day.
Niall
Slightly off topic, a tool that I got from you years ago that is immensely helpful is the process you use for dialoguing with your mentors, for getting advice from your mentors. I think this is incredibly valuable. Can we share that process for us, Derek?
Derek Sivers
Sure. It’s even probably more appropriate now in the age of smart AIs. The idea was when I’m stuck in a problem that I really want my mentor’s advice. First I don’t want to waste his time. He’s a busy guy. I’m thankful that he gives me any of his time. So I try to figure out the problem as much as I can myself first. Then I try to condense the question in such a way that it’s really easy for him to understand the context as succinctly as possible and the direct question, the bit of information that I don’t have, the understanding I don’t have, as direct as possible so that in three minutes he could read my email with the context, my direct question, and then give me the answer I need. Every time I found that in the process of doing that thing I just described, I figured out the answer for myself. Once you put the context so simply and clearly and then the question so directly, well then duh, it tends to solve itself. So the truth is, I almost never even contacted my mentors. One of them doesn’t even know I exist. But it was really helpful to think of how I would succinctly phrase the context in question for my mentor. Every time that that’s the process that ended up solving the conundrum. Think about it from their point of view. They are wise but busy, so how can you simplify this? That process seems to be most of the solution.
Niall
You have had actual mentors Derek that you’ve known in the flesh and one of them that has a really interesting story is Kimo Williams, the guy that helped you through Berklee music school when you were really young. What were some of the most important things you learned from Kimo would you say?
Derek Sivers
Yeah, Kimo. There’s an article if you go to my website, it’s sive.rs/kimo, where I tell the full story. The favorite thing he taught me is that the standard pace is for chumps. He says he doesn’t remember saying this to me, but this is the lesson I got out of it. He said, “Look, you’re about to go to university where the classes will be taught at a pace where the slowest person can keep up.” He said, “I don’t think you’re going to be the slowest person, so therefore you should not accept their pace. That’s the stupid pace. That’s for chumps. You can do better than that. In fact, I think you could learn an entire semester of material in about a week. If you read this book, read that, do the work, it’s probably just 15 hours of your time you’ll get the entire semester. So therefore, why sit in the class for a whole semester? If you value your time, just spend the 15 hours in your spare time and then go contact the teacher and ask if you can take the final exam for the class without taking the class. The head of the department should let you do this, and if you pass the final exam, you’ll get the credit for the class and not have to take the class. So doing this method, I think you can graduate college in two years.” That’s the mindset he got me into at age 17, before going to university. So I carried that approach with me in life. People say it takes this long to do something. I think that’s the standard pace. I think I can do better than that.
Niall
So this actually reminds me of something else I wanted to ask you, but let me just bring up a quote here. It’s about, it’s from your new book, actually. Go straight for what you really want. When you’re stuck in a problem, ask, what do I really want? What’s the real point? And what’s the point of that? And you ask these questions again until you get to the real outcome. And then finally ask, what’s the most direct way to get there? Can you talk about this thought process you have? And does this help you arrive at sort of like, at like first principles and sort of just not follow the crowd and not just accept the default rules and assumptions that everybody else is living by.
Derek Sivers
Yeah, well, never mind everybody else. We don’t need to compare ourselves to anybody else. But even just for your own sake, it helps so much to ask yourself, “Why do I want this thing?” Like if you think, “I want a new car.” Why? Is your existing car not moving? You think, “Well, that’s not it. It’s because I want to feel like I’m getting somewhere in life.” Like, okay, so what makes you feel you’re getting somewhere in life? Well, some kind of progress. I want to feel that I’m working towards something, that this year is better than last year, and that’s better than the year before. Or that this week is better than last week. I want to feel that sense of progress. Okay, well, what else could help me get that feeling of progress? I don’t think this is really about the new car as much, is it? I think there’s something else. What other progress? Because if I get a new car, then I’m going to still want progress to get more new things. So maybe there’s a healthier way to do this. What else could I do in life to move progress? Well, fitness. I could feel more and more fit. Well, no, that’s pretty ambiguous. Well, maybe it doesn’t have to be ambiguous. How could I make it less ambiguous? Is there a numerical way to measure my fitness? Okay, all right, good. Now this is one idea. What else? What else could help me feel weak progress? Maybe my creative output? Can I get more and more creative? Okay, well, again, is there a way to quantify that where I’m objectively feeling progress? Maybe I could start counting the number of words I write? That sounds like AI-generated spam. No, not that. Maybe count the number of posts? No, that’s still the number of words. Maybe count the number of people that I affect with my thoughts? People that are touched by what I’ve written? Okay. That’s another idea. So you just keep thinking about what’s the real point. Sorry, I just picked one example with the feeling of wanting a new car, which is not something I want to be clear.
Derek Sivers
It could go with anything. Why do you think you need a girlfriend? Is that some kind of ego gratification? Or is it an experience to dive deeper into one person and enrich in one relationship over spreading instead of spreading yourself out over many? Why is it that you want to start a business? What’s the real point there? You can’t assume the reason you want to do it is the same reason everybody else wants to do it because everybody’s got their different reasons. Some just want the money. Some think it’s a recipe for freedom. Some think that they’re just a loser until they do it. If they don’t start a business, they’re a worthless person. Each one of these things would be addressed in a different way. Almost anything you find yourself wanting in life, it’s worth digging underneath it to ask yourself, what’s the real point? What do I really want? If I suddenly had it, what problem does that solve? How would I feel if I got there? What emotion is that actually trying to satisfy?
Niall
And the way you speak about this, it makes it sound almost easy to do. What is your process for reaching and arriving at this kind of clarity of thought about what you really want? And what the essence is that you’re actually getting? How are you doing this?
Derek Sivers
I hope that nothing I said there sounded like clarity! It’s just questioning. It’s often a big muddle. The most ignorant people have the most clarity because they think that the only idea they have is the only idea there is! That’s a good amount of clarity. Once you start questioning everything, it turns into a big muddle, but you might muck your way through it and find yourself at a much better place. You just keep questioning these things, whether it’s just conversation with a friend, talking to your cat, journaling, just pondering while walking in nature, just laying down on the sofa and looking at the ceiling.
Derek Sivers
The how doesn’t matter, but I prefer journaling because I like to have them written down, because I do find that I often come back to things again in the future, coming back to something I’ve thought through last year. It really helps for me to find my previous thoughts, which I’ve often forgotten and are still really useful. I go, “Oh, wow. I solved that 90%. Then I got tired and I let it go.” Here I am a year later still feeling anxiety over this unsolved situation in my life. I search my past diary for it. I use text files so I can just search for a word. It’s like, “Oh, wow. There it is. Oh my God.” I read this thing I wrote a year ago, sometimes 10 years ago. I’m like, “Whoa. Okay. Wow. Smart past me. That’s some good stuff I forgot.”
Derek Sivers
To answer your question, as you’re merking through all the mucky thoughts and questions, something eventually will strike you as, “Whoa. Yes. That works for me. I think that’s the solution I was looking for.” Something will strike you. It might take a year before you get there, before something hits you as the right approach. Something will strike you as the solution to your situation.
Niall
It’s so interesting you say that because, you from the outside, you do appear like someone that has such clarity of thought and such, such simplicity to your, to your life, but not a simplicity that’s that you’ve come by easily, something that’s sort of been on the other side of a lot of thought and lot of doubt. And then your internal experience is just like doubt and muddling through things and all the rest. It’s just, funny how you external appearances don’t actually match the internal landscape, you know. With the journaling, something I’ve been doing for, since probably 2019 is I do like a weekly reflection and I would just like write down like, you know, what went well this week? Um, what did I learn? What didn’t go so well? Um, what’s energizing me, what’s draining me, like just basic questions. And I didn’t think anything of it. And then the past few weeks I’ve gotten the habit of like going back and just looking at like an entry from like 2019 and you’re like, It’s so interesting to see like the problems you’re worried about and what you’re working on and what was on your mind. It’s just like a snapshot in time. Like it’s, it’s such a good practice, you know.
Derek Sivers
So useful. I think it’s useful to everyone, everywhere, always. There are very few things that I think everyone should do, but journaling is one of them.
Niall
Is journaling daily for you, Derek?
Derek Sivers
For me, yeah. I like to have the unbroken habit of every single day has a diary entry. Even if I was busy or tired or out with friends and I fell asleep without writing anything about today, well, then the next day I do it. For worst case scenario, sometimes, like, say if I’ve been out with my kid and he just has my full attention from the minute he wakes me up in the morning to the minute I fall asleep singing him a lullaby at night, then maybe two days later when I get a moment, I’ll go back and write my diary for the last two days saying what I remember. It’s a shame I didn’t capture the day in that day because already just even two days later your memory gets a little hazy, you lose some of the immediacy of the feeling. But I started 13 years ago when I remember where I was standing when I wished that I could go back and read what I was doing in my 20s. I thought, damn, it’s a shame that I don’t have a diary then. I’ve just got a few random little tidbits. But was I as happy as I think I was? What was really on my mind? What was I doing? What did I do with my day? Damn, I don’t remember. A little bit, but I don’t trust my memories. What a shame I don’t have a daily diary I could read. Now, 20 years later, I thought, well, best time to plant a tree was 20 years ago. The next best time is today. So, all right, starting today at the age of 42, I started keeping a daily journal. Every single day has an entry for the last 13 years. I think it’s maybe the single most useful thing I do is to just every day, even if I’m busy, at very least write just 10 sentences about what I did today. If I don’t have time to go into the emotions, I share just quickly what I did today, because I think future self would want to know. Then I try to share the emotions.
Derek Sivers
This has turned out to be concretely so useful to me to look at my past self at a time when I was in a situation that either I’m thinking of getting into again or thinking of prolonging. Helping my future decisions by looking at my past self that was in the moment. So I’ll give you one tiny example and one big example. A tiny example was an event that I did eight years ago that they asked me to come back to that event again. I barely remember it. I went and looked, I went and found it in my diary when I did that event last year. Did I like it? The answer was yes. Wow. I loved that event. I barely remember it. But now reading my diary, I loved doing it. I loved the people there. I loved being there. It was inspiring. It was energizing. So yes, I will come to your event again. Thank you diary for reminding me how it went last time.
Derek Sivers
Another one though, I was in a two year long relationship. I didn’t know at the time it was only a two year long one. I was two years into a romantic relationship that was about to get intense. We were planning on having a kid and planning on getting married. She was screaming at me and angry at me about something. It felt like, wow, we’ve had two happy years together. But it’s really tough right now. Really, really tough. Then a friend said something about how he thinks it’s always been tough for me. I said, “Really?” I went back to my diary and I looked, I reread every single entry since the day we had met two years ago. It took eight or nine hours to read through every entry. But oh my God, it turns out that what I had remembered as a happy relationship, if I looked at my day to day experience of being in that relationship, it was usually bad. More days were hard than not. Most of the days were, “Ugh, this is really difficult. I don’t know how long I can do this!” That was only one month into it. Three months into it, I’m like, “Ugh, this is really hard. I’m feeling really frustrated. This is really difficult!” Nine months into it. Thirteen months into it. Fifteen months into it. I kept looking and it was hard most of the time. But my sunny optimistic personality had misremembered the past as mostly good. Because I just maybe amplified the few good moments in my head and went, “She’s great! She’s wonderful. We’re great. We’re wonderful!” But no, most of the time was bad. So that gave me the courage to do the hardest breakup I’ve ever had to do in my life. Because, yeah, there were some really great things about it. But my diary helped me see that it was mostly bad.
Niall
That’s incredible. This is actually that parallels quite well with the example in the book of “500 Days of Summer”.
Derek Sivers
Yeah, good movie. Anybody, everybody should go see that movie. 500 Days of Summer. It’s an interesting example of the kind of stuff we’ve been talking about here where they use the magic of cinematic storytelling to show you the story from one perspective until the end when the main character’s little sister makes him doubt it. Suddenly the movie replays that story through a slightly different lens and you realize, oh, we saw the misremembered version at first.
Niall
I think our lives are a little bit like that. You mentioned, you just touched on it there. You said you want to do the diary for the future self. And it seems like you strike me as someone that might have a good connection to your future self. Like you want that person to have a good life. You care about that person in the same way that you would care for a child or something. A good friend or whatever, know, like, that something that you’ve actively worked on to strengthen that connection or is this something that comes naturally to you?
Derek Sivers
Not naturally. I heed the advice of my elders and experts. So just as I was in the process of selling my company, you mentioned it quickly earlier, the 22 million that I had it not touch my hands and go out of charity. Part of the reason I did that is because of a book I read by Felix Dennis called How to Get Rich, where he went and made six/seven hundred million and was writing honestly and philosophically about it near the end of his life. He said, “If I had to do it all over again, I would have stopped past that first 10 million or so. The rest brought me no more happiness, and I regret the years I spent pursuing more and more. If I could do it all over again, I would have stopped after that nice, comfortable cushion and spent the rest of my life just writing poetry and planting trees.” I took that to heart because here’s a guy who is where I want to be telling me what to do differently. So I just straight up heeded that advice. All right. Well, Felix Dennis says, so therefore I will not pursue any more money. I’m so glad that I haven’t.
Derek Sivers
So same thing with, for example, a book called Brain Rules for Aging by John Medina, a neuroscientist studying the healthy aging of brains, or what makes brains unhealthy as they age with dementia and Alzheimer’s and stuff. He straight up says, “If you want to keep a healthy brain in life, here are some things you should do. This is what our studies have shown. Learn a new language later in life. Start dancing. Yes, the motor actions of dancing and especially learning a new style of dance. It doesn’t come natural to you. One of the best things you could do for your brain. Socializing with people outside of your usual demographic, especially across generations. Getting into intense conversations with them is one of the most activating things for your brain. Ping pong, table tennis is great for your brain and has almost no danger to it. Whereas, of course, you could do cycling or gymnastics, but those have a lot of dangers to them. Table tennis is the best balance of great for your brain with the fast reflexes. Good for your aerobics and your muscles and your joints, yet no dangers.” So I read a book like this and I think, all right, well, there’s my to-do list. Learn another language, take dancing lessons, socialize outside of my circles, get into table tennis, and I’ll just do these things. Same thing with the more recent book called “Outlive” by Peter Attia, where he says if you want to be healthy and fit as you get older, here’s what you should do. So I try to do these things now to take care of my future self.
Niall
I love it. Brain Rules for Aging from John Medina. That sounds like the best night out ever. Ping pong, dancing, learning language and conversing with interesting people. That sounds like a great night.
Derek Sivers
Can you imagine doing that every day? I find that I’m actually planning where to live based on this advice. So as I travel the world, I notice that there are some places where I’m just more inherently drawn to converse with other people in a deeper way. So New Zealand is a place that’s great for chit chat. It’s one of the first things outsiders notice about coming here is you chit chat with everybody around you. I don’t know if Dublin’s kind of like that. I get the feeling like it’s kind of a similar chit chatty culture or it just as you go around your day. Hey, how are you doing? Yeah, a little bit chit chat. Oh, hey, nice dog. What kind of dog is that? Chit chat chat. New Zealand’s great for that. But in India, specifically Bangalore so far, actually almost anywhere in India - the cities - I’m so drawn to engage in deeper conversations with people. I find so many brilliant, shockingly smart, philosophical 20-somethings that I love getting into conversation with because they’re coming from such a different background and context than me, yet we’re playing catch with the same ideas but from two different points of view. It’s so interesting. So it’s very likely that I will move to Bangalore in a few years and live there because it keeps me socially engaged in a way that my life here in New Zealand, which is healthy, doesn’t lend itself to getting into deeper conversations with people from different generational groups. Or maybe I won’t go to that solution. Maybe I’ll stay here in New Zealand with it cleaner air, but start a podcast like you where I only interview people under the age of 30 or something like that. Who knows.
Niall
Okay, yeah, I love that. And just one question now to wrap up Derek, you have a section in the book, the meaning of life is ______. And there’s this whole discussion about the meaning of life. And maybe there is no, you know, grander meaning to it all. But you’re sort of saying it’s, it’s subjective for each person. And we sort of come up with our own meanings. So I’m curious, you’re someone that’s probably thought very deeply about this for your own life. What meaning do you give to your own existence? Why are you here on this planet, Derek Sivers?
Derek Sivers
Sorry, I wish I could give you a big bang of an answer to wrap up the interview, but it’s honestly the same answer as when you asked earlier if there is a current philosophy I’m following. I said it just changes every day. Sometimes it’s at the time of the day. So it’s the same thing with life is: If I want to write more, I tell myself life is writing, life is sharing, life is leaving your thoughts for future generations, life is expression. I’ll tell myself these things to get me to go, ugh, okay, to put aside the undone laundry and do my writing first. But when I’m engaged in something at 6 a.m. and my boy calls from the next room, “Dad?” well, then in that instant, I switch the “life is ____” because I’ve got the hierarchy right. So up until that second, life is writing, life is expression, life is sharing what’s inside, getting it out. That’s the most important thing in life. But as soon as my boy calls, “Dad?” okay, the most important thing in life is being there for my kid. Writing is second important to that.
Derek Sivers
But to stick with that example, there have been times in the past where my boy wants my full attention and I’ll say, “You know what, dude? I’ve been hanging out with you for the last five days straight. I really want to write this article right now, okay? Can you do something else while I write this? Can you go into your making room and go build something while I finish this article?” Because maybe the balance just stacked up enough pressure where I really want to write this article more than that.
Derek Sivers
So these are life philosophies. That’s where I really believe in the practicality of all of these philosophies that you’re not looking for what’s true. You’re looking for what is useful to you right now. It doesn’t mean it’s useful to you always, but for now, this is what you need.
Niall
If I had to pick one word that I feel gets to the essence of Derek Sivers, at least for me, it would, it would be useful. I don’t mean the sense of like, I just mean, you seem to have a real focus on how you can be as, as of much service as possible to the people you interact with, how you show up in the world, even how you show up with for interviews and all the rest. Like you just seem to be really, you have that top of mind. And that’s something that like, I think we could all learn from you is just, you know, just try and make that a focus in our lives, be as useful as possible to the people around you and to the world at large, you know. So thank you very much, Derek. I’ve enjoyed every minute of this. It’s been a pleasure and I want to wish you the best going forward and we’ll talk soon.
Derek Sivers
Thanks, Niall. I appreciate it.