In Search of Wisdom
host: Joshua Bertolotti
conflicting ideas, independence vs. commitment, navigating uncertainty, wisdom in daily life
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Transcript:
Joshua
Well, Derek, welcome to In Search of Wisdom.
Derek Sivers
Thanks, Joshua. I really admire what you do with the podcast and your articles and your substack. I’m a fan, so happy to be here.
Joshua
Well, awesome. The feeling is mutual. I really appreciate it. Today we’re going to be discussing your new book, “How to Live 27 Conflicting Answers in One Weird Conclusion”. Love the book, love the format of the book and everything. So I thought maybe we could start there. How did you come up with this idea of writing a book with conflicting ideas?
Derek Sivers
Well, first, everyone should read a book by David Eagleman called Sum. Sum? Did you read it?
Joshua
I have not, no.
Derek Sivers
Okay. So the very first page of my book, “How to Live”, says this book is an homage to the book “Sum” by David Eagleman. So it is a straight up homage the way that an indie musician may rerecord the Beatles, Sergeant Pepper’s start to finish or something like that. It is using the format of the brilliant book Sum. So first let me tell you something about the book Sum. So David Eagleman’s book-- the subtitle I believe is “40 Tales from the Afterlives.” And it’s 40 short little stories like three pages long, each of what happens when you die. But my favorite thing is that each chapter disagrees with the other chapters, so it’ll be like chapter three “When you Die, you find out that in the previous life you got to choose to be a human, but now you’re back in the spirit realm and you get to decide what animal you’d like to be. So you decide to be a horse. As soon as you say that, you start turning into a horse. But then you realize, ’Oh no, my brain is turning into a horse’s brain and I won’t be able to appreciate what it is to be a horse. Because what I liked was being a man, appreciating the life of a horse.’
Derek Sivers
I don’t actually want to be a horse and you try to complain, but all that comes out is. Then the very last sentence says. Your last human thought is what kind of beautiful, complex creature might you have been that chose the simple life of a man?” Whoa. Great little three page short story. Right? But then the next chapter says, “When you die, you’re in a giant mansion and you walk around forever trying to figure out if there’s anybody else here. And you find out that God is a creator but not a manager. So he created us years ago and now nobody’s home. We’re all alone.” So what I loved about his book is this format of every chapter disagreeing with all the other chapters. It’s answering the same question, which in his case is “What happens when you die?” Answering the same question in 40 different ways with 40 different conflicting answers. So I love that book so much. And I read it twice over two years. And then one day I was driving down the road and I went, “Oh my God, I need to write a book called How to Live in that same format where every chapter is going to have a strong opinion of saying, Here’s how you should live.
Derek Sivers
Be independent cut. All ties depend on nobody and nothing. Nobody can truly be happy until you’re independent. That all misery comes from dependency. And then the very next chapter would say, Here’s how to live, commit, pick a place, pick a person, pick a career, Get the deeper joy of the long relationship with everything you know, bind yourself to these things because that’s where the real benefit comes.” And the thing is, all of these answers are true. They are all a good way to live, all a valid way to live. So the joy then is presenting them all in one book, which we’re not used to. We’re used to reading different books with different answers. And feeling the conflict within ourselves of saying, “The book I read last month said I should live that way, but the book I’m reading now says I should live this way.” But how fun to have all of the conflicts presented to you in one book. But then the big challenge was how to end it. We’ll leave that for a different question.
Joshua
Yeah. No, I love it. And I think, you know, it really connects with wisdom. I’ve done, I think this is probably around 130 something in terms of episodes. And I end each conversation, as the listeners know, with what is wisdom in daily life. And obviously there’s many different responses, you know, 130 different responses, and none of those are completely out left field and totally not aligned with wisdom because it’s many different things. There’s a pre-socratic philosopher that I bring up probably far too often on the podcast named Heraclitus in his writing. What we have of it is almost similar to your style. It’s not some 400 page, you know, on and on. And he says, “Whatever I say. The opposite is also true.” And kind of banging on 2500 years ago because people weren’t getting it back then. This like the opposite is also true. So I’ve got a question of essentially, why do we not necessarily care for contradictions? I was looking through the Amazon reviews of the book, and it’s a phenomenal book. Lots of great reviews. But there was one in the review that I have to share. It says, “Full of contradictions. Although there are some gems in this writing, you know, I’ve rarely read a work with so many contradictions. It’s obviously in the subtitle 27 Conflicting Answers.” So why is it that we don’t always care for some of these contradictory ideas and things like that?
Derek Sivers
I’m currently researching this subject because it applies to my next book, which is called “Useful Not True”. And Sharon Kay, who you might want to interview someday. The clearest writer I have ever read on philosophy. She’s at University of Ohio. Sharon Kay, Check her out. She has an introduction to philosophy book on Amazon that I just found breathtaking in its clarity. So I contacted her first to tell her I’m a fan. And then I contacted her two months later to say I’m working on this new book called “Useful Not True”, about how I choose beliefs because they’re useful to me, not because they’re provably true, because I don’t think that hardly anything non-physical is provably true. And she said, “You should look into pragmatism, specifically William James and Rorty.” And a few others I don’t have on the top of my head right now. And I read about three books by William James and in there, while he’s talking about other things. Now, to finally answer your question, he talks about monism versus pluralism or monist versus pluralist. This outlook of the world that wants to have one answer, one congruent, top to bottom answer. He calls that monism or being monist. And there’s something really true to that. I think he said that the number one has almost a mystical power. We think of one world, one people, one love one answer, one God, one way to live. And it’s a very enticing mindset. There’s something that feels very settling about it to say, this is it, This is the answer. This is the one thing. So I think most of us are drawn to that feeling. We want to feel that there is one answer, that there is one right answer, that there’s one way to live. So I think that’s why the reality of pluralism about there being conflicting answers that are both correct, or at least neither one is wrong is unsettling, but closer to the reality of life.
Joshua
How do you think about getting more comfortable with-- I’ve done a number of episodes. I think probably the first 50 episodes, there was some sort of questions around uncertainty and how do we get comfortable around that second part of that this not knowing that sometimes it’s this, sometimes it’s that. And I really can’t know with any sort of certainty that it’s this here and it’s that, you know, at some other time. How do you think about, you know, navigating uncertainty, I guess.
Derek Sivers
Actually, I’ve got two concrete tips for your listeners. First, I used to do this with my future. I used to think, let’s pick any particular future. Like, I’m going to move to California and start a business doing this, and this is what I’m going to do and I’m going to live here and I’m going to do this. And this is the business idea. This is what I’m going to do. And I’d pursue that path for a week or a month. Or more or less. And at a certain point I’d say, “Mm. Now, you know, what I really want to do, is be a nomad. I really just want to keep traveling the world. I don’t want to stay in one place.” And in fact, I didn’t like the burden of having customers needing something from me every day because they’d paid money. So I owe them. I don’t like that burden. So, no, in fact, what I really want to do is be a digital nomad and do such and such. And then after a week or a month or a year, I’d say, “Hm, I don’t really like the digital nomad life. I think what I want to do is, you know, so on.” I used to feel bad every time I had chosen one.
Derek Sivers
And then changed my mind and chose another one. So the solution to that is I realize that all of these were just possible futures and it was okay to just leave them as possible futures. So I made a folder on my computer called “Possible Futures”, and every time I’d have an idea, even though it felt like the right answer, like this is it, this is what I need to do. Instead of making it a decision, I would open up the folder called “Possible Futures” and I’d put all of the details in there and I’d gush out all the plans. And I’m a bit of a programmer, so I would sometimes just create the database tables and I’d start creating code for this new idea and I’d get the detailed plans. And maybe instead of actually going in incorporating a company and spending that $150 to create an LLC and a bank account and all that, instead I would just write down how I would do it. And I’d let myself dive all the way down that rabbit hole until it felt exhausted. And at a certain point the inspiration drains. And I would just leave it. There is a possible future and usually a new possible future would come along soon. And it was okay to fill up this folder of possible futures. I think I have 80 or 90 in there, each of them written out in great detail.
Derek Sivers
And every now and then when I finish one project or close the book on a chapter in my life or whatever metaphor you want to use, I turn to that folder of possible futures. And I look at the ones that aren’t going away like that still follow me wherever I go. They’re still in my psyche. I still yearn for them after years. And I’d say, “You know what? This is worth doing now because I’ve wanted this for years. This feels like a good idea for my values. And so now I’m going to pursue it.” Okay. So that’s one answer to your question. That’s one concrete way when you feel that you’ve got multiple things that are the right answer and you’re thinking in future tense. But same thing with present tense philosophical ways to look at the world. I’m sure we’ve all read one of these overview of philosophers books because they never just discuss philosophy. They always feel a need to focus on the philosophers, you know, here’s what Nietzsche said. Here’s what they say. Here’s what Schopenhauer said. I long for and would pay great money for a book on philosophy that never once mentions a philosophers name. I really think we should pull the biographical namedropping side of out of it and just focus on the ideas themselves.
Derek Sivers
But if you did that. You would have a book like “How to Live”, because you’d say one way of looking at this according to, x x, x retracted, you know, blackout those names. Is that life is misery and we’re all going to die and everything is sadness. And so the best we can do is slog through it. Another way of looking at this is thriving and so on. But each of these would be conflicting, and that’s how they are presented in these books that show an overview of the history of philosophy. They’re often in these different chapters saying, “Well, here’s one way of looking at it.” A lot of people seem to think this guy was smart and here’s what he said. But on the other hand, here’s what this other smart guy said. So I think it’s okay to keep all of these like possible futures and just consider them as possible philosophies. And then your unique human nature is to pick which one is working for you now. Which should we talk about? The ending of the book. The orchestra picture. Yeah. Okay. I was going to keep the meaning a secret and just let the world decide what they thought it was. But, you know, here we are.
Derek Sivers
Each of these philosophies to me is like an instrument in the orchestra. If you are a composer and you’ve got a symphony orchestra at your disposal, well then sometimes you want the clarinet to play something and then sometimes you want the flute to join in and then you want them both to stop and just have the cellos take over and then the timpani join the cellos, and then the trumpets join the timpani. And then all of it stops in a single piccolo plays something. It’s the same thing with philosophies that you can say “At this point in my life, what I need right now is hedonism. I just need to be fully present. I just need right now, I need to fill my senses. And just be in the moment.” And that’s what you need right now. But then you have a baby, and what you need is some long term planning. You need to live for the future. Or maybe let’s say if you get pregnant, you need to plan for the future. And then when the baby is born, you got to shift back to being just completely present and there with your kid. You can’t be managing your stock portfolio when your baby wants your attention. So these seemingly conflicting philosophies can be treated like instruments in the orchestra.
Joshua
I love it. And I love the end, just this word, this conclusion, which is is very short. You’re the conductor and composer. You know, it’s a bunny and duck. So pick up the book. But this word and it seems like a lot of your work focuses on something I think is so important of this discernment thing of knowing you know when this hedonism, present moment pleasure, whatever it may be and when long term planning. I was looking through your website and I’m new to your website and you have these book notes which I’d love for you to share with the listeners, but I was looking through and I made just a note of one quote from “Happy” by Derren Brown. You said, “The greatest burden a child must bear is the unlived lives of the parents.” As a parent, it’s really struck me, such a great quote, but it seems like you’re really after this intentional living. You know, how do you lead the type of life that you want to live? You know, please expound on that. Or, if I’m incorrect, please correct me. But I’m curious, like, where does that come from? Not everybody is really focused maybe on that, it seems like this discernment of knowing what matters and making wise decisions that are aligned with the type of life you want to live.
Derek Sivers
Thanks for catching that thread. I hadn’t really thought about that, but just while you were asking. I think it might be because I got stupid lucky. And started a company right before the .com boom and sold it right before the global financial collapse in 2008. I just did it for the ten years that I was enjoying it. And as soon as I stopped enjoying it, I sold the company and my timing just turned out so damn lucky that I sold it for more money than I’ll ever be able to spend. So that puts you into kind of a fucked up position where now you have every option under the sun. I mean, when I sold the company, I had also recently, well, a year or two before broken up with my girlfriend at the time. So suddenly I was completely untethered. I was floating in space. Meaning. I didn’t have to be anywhere and I could afford to go anywhere and I didn’t have to do anything and I could afford to do anything. So Omfg, what do you do when you don’t have to be anywhere and you can be anywhere and we don’t have to do anything and you can do anything.
Derek Sivers
Suddenly it was just like a massive blank slate in life. So I think more than most people. I had to ask myself these questions. And again, it was the timing. It wasn’t the case two years earlier. Two years earlier, I was just up to my neck in work, working 18 hours a day, and I didn’t have the time to pontificate about that. I got work to do, you know. But two years later, I had nothing but time and I had to pontificate. I never used that word out loud. I wonder if I’m using it correctly anyway, but mybe that’s why I’ve thought so much about values. What’s worth doing? The different options we all have, the different options we might not have considered, questioning myself, doubting myself, not believing the first thing that I say or even think. Pushing myself for further answers, then running those through a set of values and even questioning those to ask if there are other options I should consider. I spend many hours doing this, sometimes hours a day. So maybe that’s why I had too many options.
Joshua
A question I typically open with is something along the lines of, how did you discern your path early in life? If you could take yourself back there, you know, how do you think about that of some of the forks in the road that you might have encountered as a young person? How were you discerning and making some of those decisions back then?
Derek Sivers
Yeah. No forks. I was a knife, not a fork. I highly recommend being a knife, not a fork, no matter what it is. For me, it was music. At the age of 15, I wanted to be a great guitarist. Specifically at the age of 15, I think I just wanted to be a great heavy metal guitarist, but by 16 it had expanded into, I just wanted to be a great, successful musician. By my own definition, I don’t mean successful with money, I just mean really wanted to be great. I wanted to be a great musician, making my full time living, playing music and that narrow focus stayed with me from the age of 15 until 29, and I am so thankful for that. That I think I can wholeheartedly prescribe it to everyone, to focus on something, anything. Whether you want to be a great juggler or an AI programmer or, I don’t know, mountain climber, whatever it may be. If you’ve got one thing that you’re focused on, it helps you filter out that noise. When the world has a ton of money and resources behind. Bombarding you with distractions and trying as hard as they can to pull you off of your path into something that benefits them. You know. “No, no, no. Come look at our new software.
Derek Sivers
This is what you need. You need the newest phone. No, no, no. Come over here. This is what you need. You need to give me some money because I’m doing this thing that is so exciting.” The whole world is trying so hard to pull you off a path, and it’s the best thing a person can do. To a point to have one monomaniacal laser focused path. No forks in the road, just the knife. So that was my path from 14 to 29. And then at 29, it wasn’t so much a fork, the path just turned 29 is when I started my company CD Baby. And I created it to sell my own music. But then all these other musicians said, “Hey, can you sell my music?” So suddenly for the next ten years, I was monomaniacally focused on helping musicians sell their music. So then all the way from the age of 29 to 38. All I did was that one thing. So age 38 was the first time in my life that I wasn’t hyper focused on one thing, that I finally lifted up my head and said, “Oh, all right, world, what you got? What else is going on?” So that’s kind of what I meant, where all of these possible futures opened up.
Joshua
It’s so interesting to me this, maybe a mindset or I don’t know. Maybe you could help me, what you would call it. But this feeling of of having enough, like I’ve heard you mention and read about the proceeds that you get from books goes to charity. You know, you feel like you have enough which is another connected with the Heraclitus like another ancient idea like supposedly inscribed at the Temple of Apollo. It was like nothing to excess, you know, right below that know thyself inscription, nothing to excess. It seems like you’re living that. Like, how did you come to this feeling of, actually, I have enough?
Derek Sivers
I honestly think any clear thinking person would come to the same conclusion, which is as economists would put it, the marginal value of more money. Right. So the usual metaphor is a man dying of thirst, crawling through the desert. How much is that first glass of water worth to him? It’s worth everything. It’s worth his life. How much is the second glass worth? Something close to as much. How about the third glass? Maybe a third as much. And eventually, once you get to the 20th glass of water, well, how much is the 21st glass of water worth to him? Not very much, because he’s full. He’s had 20 glasses of water. He’s all right. And so how hard would he work for that 21st glass of water? So that’s how I felt about money after I sold my company, I mean, I gave most of it away anyway. I had some sale profits, but all the profits from the company sale, I gave it all to charity because of this choice of realizing, “What the hell would I do with $22 million?” I’d have to be stupid to spend that money. Meanwhile, people are starving. People are in desperate need. They could use it more than I can, So I’m going to give everything to them.
Derek Sivers
Because for them, it’s the first glass of water. For me, it’s the 101st, right? So it just makes more sense if you’ve got a glass of water and it’s going to be your 100th glass of water, it makes logical sense to give it to somebody that’s dying of thirst. Right? And then there’s the stuff thing. And that to me is just my personal preference that I just don’t like being around too much physical stuff. My home is empty and I like it that way. I get uncomfortable when I’m in places where every flat surface is filled with little knickknacks and vases and portraits and things, and I feel like a bull in a China shop. I feel uncomfortable, so there’s no stuff I want to buy. And I don’t need the ego boost of having a bigger bank account. I don’t compare myself to others, so it just didn’t make any rational sense. I felt like to pursue more when you don’t need more is a psychological disorder. It’s like being a hoarder, right? Those people that just Keep feeling the compulsion to get more, even though they have tons. So yeah, there.
Joshua
There was a previous podcast guest probably from a year or so ago, but I used to like kind of capture one quote per conversation. And I remember the quote was like, “When you know you’re enough. It’s not about you anymore essentially.”
Derek Sivers
Oh, good one. Yeah.
Joshua
And it’s like this idea of like having enough, like in the way of, you know, status stuff, things, money, like, whatever it may be. And then, like, another thing is like knowing you are enough, you know, it is some sort of deeper type of thing. But I do think, like you were saying, if someone can really look at it logically and maybe contemplate it and think about it, that they can come to a similar realization that actually it’s like this guy Epicurious, to do the “philosopher” name thing again that you were talking about. But it’s like if you could only see that you have everything you need, you know, it’s like we can’t quite see it. He’s stressing like, if you could only see you have everything you need. It’s a fascinating thing. Like, could you say more, I guess is my question?
Derek Sivers
What an inappropriate question. I wonder about people who are comparing themselves to others. Say somebody has earned $100,000 and they’re feeling like a loser because they’re not a millionaire. Or even worse, the people that are millionaires and feel like a loser because they don’t have 10 million or even worse, the people that have 10 million and feel like a loser because they’re not a billionaire, whatever is. To be careful who you’re comparing yourself to or think deeper about who’s respect actually means something to you. Whose respect do you value? So for me. I’d rather earn the respect of ten people I admire than a million. So that’s why I put no effort into SEO or massive promotion of my stuff on my site, my videos or whatever, because I’m not trying to reach a million people. I’m really just doing everything for the few people that I respect and they’re not even a specific few. It’s more like a kind of few. But I know that it’s a rare type of person that I’m trying to reach. So yeah, the respect of millions means nothing to me. The respect of, say, a handful of people that I respect, that means more to me. So I think it’s a better thing to aim for and if you’re feeling this thing about enough or if you’re feeling that you are not enough and don’t have enough, you’re probably comparing yourself to strangers that you don’t actually admire, you know, people on YouTube or something like that you feel you should be matching them. But I don’t think you actually want to. I don’t think those are your actual heroes.
Joshua
Yeah. No, it’s so good in the way of possible futures, this folder. Do you ever think much about your future self in the way of, you know, Derek a couple decades from now or regrets that you can live with and and stuff like that.
Derek Sivers
All the fucking time. Like all the time. In fact, it’s such a way that I just even see the world, is I always see myself on a trajectory almost visually. Like I have to know where I’m heading. Like, what’s the mountain in the distance that I’m walking towards? You know, like to use the metaphor of somebody who is hiking. What do you do? Are you just going towards the setting sun that way? Are you going towards that giant mountain in the distance or that hill or that huge tree over there? What’s the thing you’re heading towards? I’m always thinking of that. And if I don’t know my answer, I feel so unsettled that I take to my diary right away and I ask myself, “Wait, what am I doing? Where am I going? Why am I doing this? What’s this for? What’s really about? Do I really want to go there? I used to want to go there. Do I still want to go there?” I’ll spend a couple of hours in my diary to ask myself these questions. I was literally doing it this morning because I just made a couple changes in my life.
Derek Sivers
The details don’t matter, but I had to kind of recalibrate to say, okay, I’ve changed direction a little bit. I’m going here now. Let me make sure I know what that looks like. What’s the logical conclusion of this path? Where is this path going? What is this doing? Why? I’m constantly asking myself those things to make sure I’m on the right trajectory because, you know, like the the thing we were just talking about enough. Sometimes you find people or you may be a person listening to this that is just churning away on a path that you got yourself on to at a certain point because it served you at that point, whether it was a year ago or ten years ago, you put yourself onto a path and you’re still going on that path, but it doesn’t actually go where you want to go anymore. And I think you need to constantly ask yourself. Where is this road going and is that where I really want to be?
Joshua
I’m curious to ask. You have a chapter about that book that really matters to you, you know it was written for you. One of those books I would say for me is you know, Seneca, I do like a Sundays with Seneca here. So there’s many listeners that are possibly fans of Seneca, and he says something along the lines of. Like the wise person, does not always take the same steps he’s writing to his friend Lucilius. Says they don’t always take the same steps, but they’re walking a single road. Do you ever think in terms of like, do you have like a single road, like a clarity type of thing of, you know, the fruit of this life type of thing? Maybe there’s detours, maybe there’ changes, but is there like a single road or anything that comes to mind?
Derek Sivers
No, I guess I’m not wise. See, I was about to say something, but no, that changed. Somebody recently asked me, “Have you always been this way?” And it was a good friend of mine that I’ve known for ten years. And I said, “Yep, I’ve always been this way.” And then only later that night, as I was falling asleep, I thought, wait a minute. No, I haven’t. So much of who I am changed massively at the age of 38 when I sold my company. And it was very deliberate, I’d say kind of like you asked earlier about my teenage self, I’d say from the age of 14 to 38, I was head down blinders on, monomaniacal focused, no turns, except, you know, maybe starting CD Baby was a slight shift in path. But that same kind of head down galloping full speed ahead. I’m saying galloping because now I’m imagining a horse with the blinders galloping full speed ahead. And at the age of 38, when I sold CD Baby, I made myself change. And I did it so deliberately. By like a day to day, hour to hour, minute to minute basis. Everything that my instincts told me to do, I chose the opposite deliberately. And I mean literally minute to minute. Choosing what to eat at a restaurant. I looked at the thing and I said, “This is what I want.” And I went, “Oh, that was my instinct there. This is the thing on the menu that looks the least appealing to me. I’m ordering this.” And I did that every day in life. I did it ongoing for a year or two. I deliberately scrambled my operating system because I just wanted to make a change and it made me do some things. There are now among my biggest regrets. Like I whimsically married somebody I hardly knew because it was the thing that felt the most unlike me to do. So I did it
Derek Sivers
And I think it’s probably my number one regret in life. But I don’t regret the process because it sent me on a completely different path. That I really like. I really like this path of explorer. And that was when you saw me or heard me about to answer the question. I caught myself. I was about to say I’ve always been an explorer. And I went, “No, I have not.” That approach to life did not start until I was 38. I was just not exploring. I was, you know, don’t bother me with your explorations. I’m going this one place mono focused. And it wasn’t until 38 that I started pushing myself into the unknown and constantly exploring. Sorry I’ve done so much daydreaming in the past 90 seconds. I forgot your original question, but does that help?
Joshua
No, it does. In the way of exploring, what would you say you’re exploring?
Derek Sivers
Everything I can geographically, mindsets, philosophies, people, communication styles, what I’m learning, how I’m learning it, how I spend my day. I’m constantly trying whatever I’ve never tried before. Whenever I notice that there’s a place on my mind map that’s unmapped, I go there and I’ll just concretely, I’ll give the most recent example is just two weeks ago. A friend was asking me where he should incorporate his company. Because he’s a digital nomad and could be anywhere. I was like, “Well, there’s this, there’s that. Singapore is a good place to do it. On the other hand, New Zealand is really fast. On the other hand, you know, look into Wyoming, USA, it’s got some really good looks then. Then I was like, Oh my God, what about Dubai?” I never think about the UAE. Like the Middle East is just not on my map. I don’t know anybody there. I’ve never been there. I’ve never thought about it for a single minute. So I gave him that answer. But then, like literally as soon as he left, I immediately went to the computer. I was like, “United Arab Emirates. Saudi Arabia” I know nothing about this part of the world. And then luckily the very next day and you people that believe in the law of attraction can nerd out on this. I got an email from a British guy living in Abu Dhabi who said that he’s a huge fan of my stuff.
Derek Sivers
And had a really insightful, wonderful email. And really lengthy. Just one of those people that really likes to write long emails. And I said, “Hey, you live in Abu Dhabi, why? And what’s that like?” And he sent me like 20 pages in reply, like, “Oh my God, Derek, if you’ve never been here.” He was telling me all the benefits of living there and what he loves about it and sent me a whole bunch of photos. And if you come, you should go here and then. All right, I’m going. And I booked a flight and I’m going in seven weeks because I know nothing about it. It wasn’t on my radar, so I want to know more about it. But same thing, I was lifting weights right up until two minutes before our interview. I was doing squats and overhead presses. I have a little home gym here and ten years ago I used to look down on weightlifters. I thought they were idiots wasting their time in the name of vanity. And then multiple people told me about the benefits to your skeletal system and why as your aging it’s one of the best things you can do. I went, “Well, okay, I am completely prejudiced against it, therefore I’m going to do it”. And I started going to a gym and I learned about weightlifting and had a good coach teach me the right way to lift and I’m totally into it now. So I keep doing that stuff ideally every day. I love steering towards the mysteries, steering towards the unknown, steering towards the things that feel so weird and uncomfortable to me. Whenever I notice that feeling, I steer towards it.
Joshua
So fascinating. There’s a lot of guests that I’ve had on that talk in the same way, and I feel that same way of like In Search of Wisdom, there’s some sort of like, like someone can be bit with something and there’s like an insatiable search for fill in the blank, whatever it is. Just some sort of search that can just last a lifetime, like people that have had 60 years they’ve been at the search. And like sometimes I wonder like Seneca was talking about like that road really some sort of broad thing he’s talking, as long as you live never stop learning how to live like some sort of thing connects with obviously the title of the book. And it’s a fascinating thing. And I made a couple notes here from the book that I want to specifically kind of just get your take on if I could. You open the book, as you mentioned, independence. You write, “When you say you want more freedom from the world, you may just need freedom from your past self.” And this has come up a bit in the conversation, this freedom from your past self. How do you think about that and what does it look like? Maybe you’ve given some examples of I want to do this, do I really want to do this? I’m going to do the opposite. But if you could maybe unpack the how around that, because that can be a difficult thing for some of us of doing that opposite unknown thing.
Derek Sivers
Yeah I think the concrete directive is to open your journal, whether it’s paper or text file or whatever. And think of a belief that you hold or an action you do that’s not working for you that you think is actually hampering your progress to being your ideal self. And question it, challenge it. See, why do I do this? Why did I start doing this? Sometimes it really helps to know the origin of things. I believe this is true. Why do I believe this is true? Because all these people told me is true. Why did they tell you it’s true? Question that like, maybe it just kind of served their agenda. It helped make them a more quotable leader which fed their ego, but the things they were saying were not actually true. But you took it as true because you looked up to them because other people did. And so now you hold this belief just because somebody that you looked up to when you were 21 said so. And creatively think of the opposite. And actually, whenever I think of opposite, by the way, I always think in terms of not 180 degrees opposite, but like 170 almost opposite, because then you can ask yourself, what’s the opposite of that? And then the opposite of that, it’s like if you keep going at 170 degrees, then you go all the way around the circle.
Derek Sivers
To just challenge your beliefs. Even if it feels wrong, or especially if it feels wrong to entertain that notion. Entertain the notion of what if this belief of mine is wrong? And what if this action I’m taking is a bad strategy. And what strategy would be ideal for the outcome I want. What is the outcome I want? Okay. What’s the most direct way to get the outcome I want? Even if it’s unusual or even if it’s socially unacceptable, what’s the most direct path to what I want. Well, then why am I not doing that? And I think just asking yourself these questions. And then always steering towards the action you can take. Not just sitting there thinking about these things. You’re not writing papers for a professor anymore. It’s about what actions are you going to take in your life. So what actions does this mindset or this worldview or this philosophy seem to dictate? And then you take those actions and can you at least try taking those actions to see if it’s applicable in real world?
Joshua
I love that the 170 degree and like the what now thing. Another previous guest, this cognitive psychologist who wrote Thinking 101. The listeners may remember she said any why question you can’t find an answer to. So like it doesn’t mean in terms of these peeling these onion peels back like, you know, and getting curious, but like and maybe that connects with this idea of the book. It’s like you’re exploring it. But then at the same time, well, what now? You know, in the way of like, looking back, like peeling the onion back in some sort of, you know what? Now, moving forward towards this action thing. It’s such an important thing because that seems like really how it is that’s in real life because you could spend ten years exploring some sort of why question and not necessarily get to any sort of definite answer.
Derek Sivers
Well, and also confabulation is a fascinating subject where even if you answer why, you should not believe anything you say. Notice that researchers, psychology researchers don’t ask people why because they know that anything people would say is just kind of noise. Look at their actions. Actions reveal values, not people’s blah, blah, blah explanation. So you shouldn’t believe your own either. But rewinding a bit to when we were talking about William James and the monist versus pluralist worldview. Don’t try to find the right answer. Don’t try to figure out what’s true. Only look for what works for you now. So when you’re entertaining these different notions in your journal. Beware of this tendency to try to figure out the right answer. Just create a bunch of different options and never stop at the first one. In fact, don’t stop at the second or third one either. Keep going. Once you’ve got a menu of options. Pick the one that would work best for you now. Or let go of the idea of it being true or even right. But just the one that serves you the best. Now that gets you to where you need to be next.
Joshua
So good.
Derek Sivers
Wait, can I make a visual metaphor. You talked about Seneca’s path. And I talked about the mountain in the distance. If you want to get to the top of the mountain, sometimes what you need to do is to go down a bit into a valley in order to get around the cliff and come up the back side. So going down is not the right answer for how to get up the mountain, but yet it’s what you need to do now. To get where you need to be next. So that’s the problem with people constantly asking themselves what’s true. What’s right. Is you’re not trying to find the ultimate truth. You’re just trying to help yourself take the next action that you need to take.
Joshua
Something I made a note of, I heard on a one of the podcasts that you were on about labels, and it seems like connected to that in my own experience and then like experience of others. A sticking point of, say that going down in that ravine or even just kind of making moves in general can be these labels. And please correct me if I’m wrong, but I want to say I’ve heard you say adding today to a particular statement. You know, I’m a X, Y, Z today. I love that. Could you say more about, you know, labels and maybe loosening our grip on them?
Derek Sivers
Yeah, I find that to be a useful hack. A quick, simple hack you can carry in your pocket is to constantly acknowledge that you’re constantly changing. And so whenever you say, I’m an introvert or I’m a fan of Miles Davis or I’m super into Seneca. Sorry. You know, I had to just think of one that applies to this. Is to add the word today. Whether you say it out loud or you just remind yourself that it might all change tomorrow. Tomorrow you might read a book that blows your mind that says, actually, Seneca was totally wrong, and here’s why. And you might read this book and go, “Oh y God, all of life makes sense now. This is amazing. Whoa! Oh, my God. Everything I’ve learned about Seneca was wrong. And I love it. This is so much better.”
Derek Sivers
You should keep yourself open to that possibility. And in fact, it just happened to me two months ago. I’ve been calling myself an introvert for 20 years. And I loved Susan Cain’s book called Quiet, where she defined an introvert as not somebody who doesn’t like being around people or not even that whole like, where do you go to recharge your batteries around people or away from people? But she said it’s just a matter of how much input you need to feel alive. And they did these tests where they measured lemon drops on the tongue of self-proclaimed extroverts and introverts and people who call themselves introverts. One drop of lemon juice on the tongue stimulated their nervous system as much as five lemon drops of lemon juice on the tongue of an extrovert. So the whole idea is an introvert only needs a good book to feel alive. But an extrovert might need Burning Man or something to feel alive, right? So I’m like, “Yep, I am completely an introvert. I am off the charts. 100% introvert.” Sorry, 100% is not off the charts. So then after ten years in quiet New Zealand, living a very quiet, solitary life, I started to feel dead and dying and just stuck.
Derek Sivers
And I wanted to go to India. So two months ago I impulsively booked a trip to India and met up with a ton of people in India. I blogged about it. If you see it on my site, it’s a sive.rs/met-chbg because I went to Chennai and Bangalore and oh my God Joshua, I’ve never felt so alive in so long. And it was this intense feeling of this is what I needed. Oh my God, I’ve been living this low stimulation introverts life because I had defined myself as an introvert and therefore I had been living like an introvert. But oh my God, I think that might have been one of those things where I should have added the word today because I think something’s changed in me. I’m feeling more like an extrovert now. I still don’t like parties, and I think that might have been the confusion because when you’re at parties the conversation is usually quite dumb. Just, you know, cocktail party talk, little bar room chatter. They’re not interesting conversation. So I was thinking about times when I was around a lot of people and I think, “Uh, yuck. I didn’t like that.” I couldn’t wait to get home to a good book. Therefore, I am an introvert. But actually, maybe I just hated having stupid conversations and I was yearning to get back to more intellectual stimulation. So yeah, I should have added the word today to my self-definition as an introvert long ago because I’m really doubting it now.
Joshua
It’s so interesting just this idea of relational, like all of these particular chapters in your book. Sometimes it’s this, sometimes it’s that and so much depends on the circumstances of that particular situation and what matters to you, you know, in that particular moment.
Derek Sivers
Yeah.
Joshua
And connected to that the other note that I made was on the chapter. Do whatever you want. You write, When people as the meaning of life, they’re looking for us. When they ask the meaning of life, they’re looking for a story. But there is no story. Life is a billion little moments. They’re not part of anything.” I love that. And I’m curious for anyone listening, maybe the both sides of that, maybe someone that hears that and it’s not so inspiring. You know, what’s the inspiring thing of that? Because it is a beautiful thing if we’re thinking about becoming every day, like we’re not these particular labels, like each and every one of these moments it’s like perennial opportunities, if you will.
Derek Sivers
I wasn’t trying to be inspiring, but just now when you asked the question. I thought of a nice metaphor. Is yes, I believe that everything that ever happened to you is not a narrative is not a story. There was no trajectory. It was just a bunch of individual things that happened. And first, make sure that you strip away the story you’ve told yourself about it. And again, sorry, that’s what my next book is all about. The “Useful Not True” book spends a whole first half of the book pointing out over and over and over again. This isn’t true. That’s not true. That was all just your interpretation. That’s a story people make up about what this means. Your mother said to you, “You’ll never amount to anything.” And a kid at school said, “You’re just bad at everything.” What does that mean? Nothing. It doesn’t mean anything. It means nothing at all. It means your mother spoke those words and she might not have even meant it. It meant nothing that she said it. There is no other implied meaning. She just spoke those words. She doesn’t know why she spoke them. Even if you asked her why and she gave an answer, it’s probably not the real answer. She doesn’t know why she said it. However you interpret it at the time was just your interpretation of it at the time. It means nothing that you took it a certain way. And then the kid at school said this thing, for whatever reason, he might have been jealous. He might have had the opposite, meaning he might have actually thought that you were great at everything and wanted to take you down a peg. You have no idea. So nothing means anything. Nothing has inherent meaning. It’s just things that happen. What happened is your mother spoke these five words and that kid spoke these seven words.
Derek Sivers
That’s all actually happened. It’s just a bunch of pinpoints in your history. Like stars in the sky. Now, imagine the constellations. Imagine that long ago somebody said, “That’s Orion’s belt and that’s Uriah and that’s the--” I forget the constellations. I haven’t thought about them in a long time. But imagine you grow up thinking,”Oh, that’s what that is Orion’s belt and that’s what it is.” And somebody said, “Oh, that’s the dragon’s mouth.” And he went, “No, no, no, no, no. That’s Orion’s belt. That’s what it is.” It would take somebody to kind of shake you out and say, “No, no, no. You just had Greek parents. That’s not what it actually is. It’s just stars in the sky. And in fact, hey, come down to New Zealand. They look different down here. They’re in a completely different shape.” And to realize that you can creatively draw your own lines between anything that happened in your past and between anything that’s going to happen in your future, you get to draw your own lines. You can decide that’s actually a lemur and it’s leaping to a cactus. That that’s what that collection of stars actually is, a lemur leaping to a cactus because you decide that’s what it is. And it helps us so much to strip away the untrue meanings and untrue doesn’t mean false. It just means not true meanings that people have told us that things in our past meant, or that you told yourself that things in the past meant. Believing those things, believing those stories can get you really stuck. I find it very emancipating to strip away those stories.
Joshua
Is there a particular view and belief that. you’ve cultivated some new new lines in the sky that comes to mind, that’s had a had a positive impact here lately.
Derek Sivers
Yeah. I’m embarrassed to say, but, hey, that’s what interviews are for, right? Yeah. I had a couple of those kind of things in my past that made me think I was bad at sex. There are sexy people and I’m just not a sexy person. That’s just life. Some are and some just aren’t. And I never questioned that. Until just a couple of years ago. And I’m 53 and just a couple of years ago, a few things happened. That made me question that and wonder why I had always thought that. And just as I was doubting that, my sister of all people, said something like in passing, we are talking about something completely unrelated. I had never told her my recent rethinking about my history with sex, and she said something about like, “Well, you’ve always been the hot one.” Or something like that. I went, “What?” And she goes, “You know like high school, college or whatever you were just the one that all the girls just thought you were the hottest thing.” I was like, “Wait, what?”
Derek Sivers
She goes, “Yeah, don’t pretend you don’t know that.” I was like, “No, I didn’t know that. I honestly didn’t.” And suddenly, like having my sister say this to me. I was like, “Oh my God, Wow. I really had written a whole story about my past that was completely wrong.” And I just took it as truth despite all of my reflective nature that you’ve heard in this conversation. Despite all my journaling or whatever, I just never even questioned that. That was always just a true thing. And. Yeah, sorry. That was kind of embarrassing to tell in this. You know, here we are to talk about stoicism and sex.
Joshua
No, I love it. Appreciate you sharing. It’s such an interesting thing how we have these about all sorts of-- like sometimes I’ve heard in terms of a philosophy of life, say it’s like, well, we have one, like we all have one. It just might not necessarily be aligned with reality. Like some of these things like we’re making up. Like the story. Well, we all have this thing. Like even that quote that I read about the unlived lives type of stuff. Well, we all have views and beliefs about all sorts of stuff. You know, if you just ask somebody, there’s at least a story. But how do we question it like you’re talking about and ask, W”ell, what do I know? How might I be wrong? What’s the 170 degrees of this?” I’ve heard a conversation and sometimes people talk about like a minimalist or, you know, someone that’s not maybe focused on excess and accumulating things as like living a simple life. But when I read your book or hear you talk about these things and in my own experience. And there’s nothing about the introspective life to me that is simple. Like it’s so interesting. It can be so exciting compared to buying another pair of pants or whatever it may be, you know, or another house or whatever it may be. There are things that if we could maybe only see it. And obviously everybody has the agency to lead the type of life that they want to lead. But it’s not simple in many, many ways, you know.
Derek Sivers
Yeah, but that’s okay. You don’t need to simplify your thoughts. Again, that’s just something you can do for a certain outcome. I do think that thing I said earlier in the conversation that I would actually prescribe and recommend that people simplify their thoughts and maniacally focus on one single thing, get on the path to mastery and ignore everything else and just do this one thing. I think that’s incredibly effective, incredibly productive, incredibly rewarding. To go that deep into one thing and feel those rewards that most people never get to feel, people that stayed shallow. So it’s okay if your thoughts are very simple, although I imagine people whose thoughts are very simple don’t tune in to your podcast.
Joshua
But speaking of shallow, it reminds me of another thing that I thought was really interesting. I heard from you is deep happy versus shallow happy, and I’m curious to maybe add something to that, you know, deep wisdom, since this is in search of wisdom and shallow wisdom, if there’s anything that that comes to mind.
Derek Sivers
No. Does it for you?
Joshua
Well, in terms of how I heard, like the deep happy and shallow happy, there was like examples of, you know, shallow, happy might be something simple like, you know, ice cream, fulfill some sort of immediate pleasure, like a deeper happy. And I didn’t hear you elaborate, but as I was thinking about it, connected with maybe that, future me, that future self. Is there something that is maybe I can do now that might even bring me some happiness five years from now or ten years or ongoing?
Derek Sivers
Yeah.
Joshua
You know, and same thing. I wonder if that connects with wisdom like some things that we could do now. But I mean, happiness and wisdom, I think are honestly pretty, pretty similar in how to live and things like that. Lots of synonyms around.
Derek Sivers
You think about the word wisdom a lot more than I do. To me, the deep versus shallow happy is a pretty easy idea to wrap your head around. Like you said, eating an ice cream for three minutes would make me happy. Not eating the ice cream would make me more happy for a longer time. Because not only would I be proud of myself, which is in itself a deep happiness, but I’d be fitter and healthier for longer. I’d live a longer, healthier life if I don’t eat the ice cream or if I break the habit of eating the ice cream. Not just this time, but for the 100 next times as well, that would lead to a longer, deeper, happier life because I’d be healthy instead of just going for the two minute pleasure of eating the ice cream right now. So yeah, I think more of us should and I very rarely prescribe things, but I think more of us should steer towards deep happy instead of shallow happy. We should forgo the shallow happy. And choose the deeper happy, whatever it may be for you. And I think a good compass is whatever would make you proud of yourself and not impulsively proud. But wisdom, I don’t know how to apply that metaphor to the word wisdom, so yeah. Any thoughts appreciated?
Joshua
Well, maybe this is a good spot as any to bring us to that final wrap up question though, which is how do you define wisdom or think about wisdom in daily life? So I’m curious to like set it up a little bit. I know you as a dad. You know, like like me. I have two younger kids. Really, really important to me. Part of this search for wisdom is really to hopefully be a little bit better dad. You know, if your son comes and asks you, “Dad, what is wisdom?” Anything come to mind? Hmm.
Derek Sivers
No.
Joshua
No. I love it.
Derek Sivers
That’s my honest answer. Yeah, it’s. I’m sorry. Again, it’s I actually don’t think of that word much even at the beginning of the interview. I’m sorry. I don’t remember if it was right before we hit record or right after when you said that you ask everybody the definition of wisdom. My first thought was, “Oh, fuck, I never think about that. Maybe I’ll have an answer by the time he asks.” Yeah, but I don’t. It’s one of those words like love that there are so many definitions. There are so many things that word could mean to different people. And so love to me is a word feels almost meaningless because you don’t know which meaning somebody means when they say it. Friend is another good one like that. What does that even mean? Facebook friend. Dear friend. You know, we have to add these extra adjectives. So. Sorry. No, I don’t have any thoughts on wisdom.
Joshua
Honestly, I think if my daughter, you know, who’s ten was to ask me that. I would probably say something along the same lines as I’m not really sure. You know, it’s it’s many things and it’s--
Derek Sivers
Sorry. You know, I may have one for you. Yeah. I was waiting until you finished that sentence, but now it sounded like you weren’t going to finish that sentence.
Joshua
No, go ahead. I felt something.
Derek Sivers
Like what? Do you think you’re going to sneeze? I know. It’s gone. All right. Internalized. It’s just off the top of my head. Wisdom is what’s internalized. It’s when you’ve either thought or heard good ideas. But you’ve really internalized them. And put them into practice and they’re like a part of your soul now. To me, that’s when it becomes wisdom.
Joshua
Yeah. That’s good.
Derek Sivers
Here we go, my dumb contribution.
Joshua
I love it.
Derek Sivers
Often asked question.
Joshua
But even this thing, I mean, that’s kind of what I was thinking a little bit in terms of my daughter was the ask like, I don’t know. It’s in a way of-- there’s some sort of quote of like, “Beware of unearned wisdom.” You know, it’s like you that’s something that each person uniquely has to internalize that to use your word or write that story of what wisdom is to to you. So it would be a difficult question. Thankfully, she hasn’t asked me that question yet. But someday. Someday she might. But before I forget to bring it up, though, I would love if you’d share with the listeners this idea of book notes on your website like hundreds of--
Derek Sivers
Joshua! I was just going to say, the point of that page is to turn the things I’ve learned into wisdom. The reason I’m sorry to interrupt. So listeners sorry, what Joshua was about to say, I think, is that there is a page on my website, it’s sive.rs/book, and on that page are the most recent 400 and something books I’ve read since the year 2007 is when I started taking notes. I read hundreds of books before that too, but I realized I was forgetting them. I would look at this book on my shelf and go, “Wow, I know I liked that book, but I don’t remember anything it said.” I thought, “Oh God, I don’t want to have to read that 300 pages all over again. I wish I had taken notes. All right. Starting today, I’m taking notes.” So now every single book I read. I do it with a pen in hand, underlining my favourite ideas or circling paragraphs, or if it’s a Kindle, I use the highlight feature, but then afterwards I do the dreary slog work of turning all those ideas into a coherent text file. And I do that for my own sake so that I can refer back to it often and turn these ideas into wisdom. I want to reflect on them. I want to think of how this idea in this woman’s book applies to my own life. How can I apply this to my current situation? In fact, I read this book nine years ago.
Derek Sivers
It didn’t apply then. But how can I apply that idea now to this conundrum I’m in today? Let me reflect on that and I’ll sit and I’ll pull up that idea and I’ll kind of put the idea at the top of a diary page and then just write for a whole page on thinking around this idea, sometimes challenging the idea how it could apply and trying to really internalize it and then ideally put it into action. I’m very action focused. I think that a lot of thoughts are pointless unless they turn into action. Yeah, that was the purpose for it. So along the way I decided I should share these with the public. So if you go to that URL sive.rs/book, you will see all of these books. And then I also - because enough people asked - I started ranking them in terms of how much I would recommend it to others, which might not necessarily be how much I liked it. There are some weird books on, I don’t know, Ruby computer programming that I loved, but I would not recommend it to anyone else. So I sorted them like that. So now when you just go to that page, you’ll see my most highly recommended books at the top, and I think everyone should read all of those.
Joshua
Nice. I love it. It’s it’s a beautiful thing. And I’m sure it’s thousands of hours of typing and and creating that. I love when we’re able to do something for ourselves. But then you also, like went a step further of, you know, how might this help others and lots of respect for the thousands of hours of going through there. And I’m going to go through it quite a bit and we’ll link it in the show notes. I think a lot of listeners will really appreciate that.
Derek Sivers
Thanks. But listeners, please do not take it as a substitute for reading the book because I am not writing summaries. Let me be clear. These are not book summaries. I am only extracting the ideas that I personally felt were the most surprising to me and needed more reflection. Sometimes I’ll read a whole book and I’ll only extract seven sentences from it. It’s not a summary of the book, it’s just my personal few ideas plucked out of the book. So if you’re reading the little bits I’ve extracted and they sound appealing to you, please go read the whole book. Because I do think reading just my notes and not the book, it’s like somebody telling you just the punchline of the joke without the joke, you know? And then the duck said, ’I don’t know who this guy is.” You know, if you’ve already heard the setup to the joke, the punchline is enough to remind you why that joke worked. If you haven’t heard the setup, the punchline doesn’t work. So what I’m jotting there in my book notes is just the punch. You should definitely go read the book. Don’t see my notes as “Oh, good. Now I don’t have to read the book because Derek took notes.”
Joshua
Well, great. And another book to read is your book, “How to Live”. I highly recommend it. Love the book. I had just to share another bit of information for the listeners that the rough draft started out over a thousand pages.
Derek Sivers
1300 pages. Yeah.
Joshua
And this final book of around 120 pages is packed with lots of wisdom. And I think many of the listeners will enjoy it. So is there anything we--
Derek Sivers
And also. In fact, listeners, please don’t go to Amazon. They don’t need any more money. If you go to my website, go to sivers.com. I sell all my books directly self-published. When you get the book from me, it comes with the audio book and the e-book and in some cases, the video book. I hired animators to turn one of my books so far into a video book, and all of that comes included, and every single penny of it goes to charity. So I highly recommend get the book directly from me. Decentralize. Don’t go to Amazon.
Joshua
Awesome. And we’ll link it in the show notes so it’s easy to find. Derek Sivers, thank you so much for coming on in Search of Wisdom.
Derek Sivers
Joshua, thanks for the very fun questions. I loved this conversation. Thank you.