Less Clueless
host: Steve Sima
How to Live and its orchestra metaphor, Asian parent guilt, family dynamics, romantic relationships, loneliness, money and morality of business, shallow vs deep joy from money, everything is figureoutable.
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Transcript:
Steve Sima
Okay, Derek. So last time we spoke, we talked about your new book, Useful Not True. And today, I want to focus on your magnum opus, How to Live. Because, you know, first of all, I just got to say, holy shit, dude. Like when I heard you say, this is your masterpiece, I just thought, you know, artists, they'll have subjective, you know, this is my masterpiece and so on. Yeah, whatever, man. And I read it and this thing read like a hundred books worth of insights distilled down to 129 freaking pages. I swear to God, I highlighted half the book. So congrats on it. I mean, it's not new, but I want to touch on it. It touches on so many themes from relationships to money to everything about life.
Steve Sima
I want to start with something that you're quite known for and something I respect you for, which is reinvention. You write, the way to live is to regularly reinvent ourselves. Why is that?
Derek Sivers
It's tough with the How to Live book to defend any one point of view because you have to click into a mindset where you think that this is the answer. That's what every chapter did. It said, "No, forget the rest. This is the way." So I have to click into the mindset that says that reinvention is the answer because it lets you live the fullest life.
Derek Sivers
Imagine you live in a huge house and you spend your whole life just in the living room and you never leave the living room. People bring you food from the kitchen and they bring you your pillow from the bedroom, but you never leave the living room in your whole life. You're missing out. You could be seeing the world from many different rooms. Or let's expand the metaphor. Imagine you never leave your hometown your whole life. Imagine you never wear anything but shorts and a t-shirt in your whole life and you've never tried putting on a suit. Imagine you've only ridden a bicycle in your whole life and you've never tried a car. You've never tried an airplane and you've never tried a horse. I could keep going.
Derek Sivers
The idea is the default way you are is just one way of being, and it's your default. It's the one that comes the easiest. So if you want to live a full life and experience different ways of being in the world, you have to deliberately reinvent yourself to push yourself away from your defaults and into something that feels unnatural at first. Like the first time we ever got on a horse, it was not the most natural thing. Then somebody teaches you how to get into it. Same thing with trying on a different lifestyle: a different line of work, a different way of being in the world.
Steve Sima
And you followed that statement up with saying, every year or two, change your job and move somewhere new. So I think the way to read this book, you can really get kind of misunderstood if you don't read it in the right way in terms of like, there's one chapter that has this extreme view And then the next chapter has the opposite view. And there are seasons in our life. There's our balance.
Steve Sima
Every year or two change your career and move somewhere new is pretty extreme. So how do we balance that with having emotional stability?
Derek Sivers
You don't need to. Emotional stability is also just one way of being. That it's held up as something we should all want, but there are many things that are held up as something we should all want. Some people say we should all want a spouse and two kids. Some people don't want that. Some people say we should all want to get rich. Some people don't want that. So stability is not an absolute good. It's just one proposed good.
Steve Sima
What about depth? If we're changing all the time? Because one of your other chapters talked about pursuing mastery, and sometimes that takes years. Right how do we balance that with depth and long-term commitment?
Derek Sivers
Ultimately this is where you have to use your preference. You have to look inside yourself enough to realize what makes you thrive, what makes you flourish, what makes you most deeply fulfilled, which may be going deep into one place, one career, one person, or it may be continuing to surf the surface.
Derek Sivers
There are surfers and there are scuba divers, and neither one is wrong.
Steve Sima
Yeah, and I guess there's just certain seasons in our life where we do one thing and certain seasons where we do others, right?
Derek Sivers
Yes. Did you get that in the orchestra metaphor at the end? The book How to Live ends with a picture of an orchestra seating chart with 27 instruments in the orchestra, not coincidentally to match the 27 chapters of the book. And the idea is you are the composer and the conductor that can use these philosophies like instruments. A composer decides he wants to use a trumpet right now and then decides to use the violins and then to stop the violins entirely and just have a single clarinet play.
Derek Sivers
You can do this with the philosophies in life. You can have a time in your life when you're completely driven to make money. And that's all your focus. You're not balanced. You're not deep. You're not mastering anything. You're just out to find the profit. And then let's say you get your income to a comfortable level. And now you shift your priorities to, say, giving back. And now you say, "You know what? All of my needs are met. I'm turning my attention to giving." This is life. This is how it goes. You don't have to pick one and declare it to be the right answer. You just use what works for you now.
Steve Sima
The seasons thing is so interesting. At the moment, I've just completely cut - aside from your books, for these interviews - I've completely cut out nonfiction from my life. Because in another chapter, you say, just create, don't consume. And I just find that at a certain point, consuming is just mental masturbation. It's just, "Oh, I feel like I'm being productive." But then I'm not really actually going to do anything, but it lowers my guilt just enough so I can keep surviving. And creating, you know, creativity begets creativity. You don't need to read more books to create. But then at a certain point, when I need inspiration, I think if we're really in tune with ourselves and we're honest with ourselves, we'll know to change to the other instrument, like you said, right?
Derek Sivers
I love it. Beautiful example.
Steve Sima
Yeah. What are some examples of your life where you reinvented yourself and what did you get out of it? Some insights that you gained out of it?
Derek Sivers
Sometimes the outside world presents you with a situation and you have to change your approach. And this is where philosophical flexibility comes in really handy. So if you were pursuing one path, completely focused on it, and then say, for example, you or your partner gets pregnant, then, "Oh, hmm, okay, I might need to change my path right now." So that happened to me. That was very unexpected. We had actually deliberately decided not to have kids. And in fact, we had just broken up. And then she found out she was pregnant. So I had to change my priorities because I think looking after a brand new human is top priority over anything else. Nothing compares to that. Making money is not as important. Reading books is not as important. Creative output is not as important. Adventuring is not as important. By my value system, helping shape the emotional and mental and physical well-being of a new person is way more important than everything else. So that's one example in my life. When I sold my company, that was also unexpected. I thought I was going to run that company for the rest of my life. And then the business situation combined with a bunch of offers in one week. I got three offers in one week to buy the business. It felt like the universe was poking me in the face, telling me to take a hint. And so I sold the company, which I was not expecting. and I went from having some money to having way too much money and I went from having no time to having all the time in the world and I went from being bound to a place to being completely unbound. So suddenly in one day everything changed. So I had to adapt.
Steve Sima
Did you have an identity crisis afterwards?
Derek Sivers
Yes, yeah. I had to adapt to the new situation because I had been living the old situation for 10 years. Suddenly the entire situation had changed.
Derek Sivers
In fact, let's go somewhere unexpected with this. Cultural things. Many of my friends are from India. And in India for probably centuries, there has been this culture where it is the child's duty to take care of the parent when they're older. Because the economy for centuries was quite hand to mouth. Through your labor, you would earn as much money or food or goods as you could consume this year. And so if you're in your 70s and your 80s and you're not able to work as productively, you don't have any savings because everything you did was just for now. And so it's the child's duty, since they're able to work, to take care of you. But it's 2025 and we live in a world where at least half of the world can save money and save for the future. And I think has an obligation to themselves to save for their future so that they're not dependent or a burden on others. So the situation has changed, but yet I hear people holding on to the traditions just because it's the way they're used to being. They're used to a world where it's the kid's duty to take care of the parents. It made sense in the old situation. It doesn't make sense in the new situation. So you have to update yourself philosophically to align with the situation, whether that's a baby or selling your company or living in a world where we can afford to save our money.
Steve Sima
You actually jumped ahead to something I was going to ask you later, which is you wrote something along the lines of my son owes me nothing, which is so, you know, me being East Asian, and like you said, South Asians have similar cultures as well. This idea of filial piety, you know, piety, parent worship, literally, right? Where you must obey your parents, you must take care of your parents. And as you said, it's incredibly useful in a pre-social safety net world to make sure the old people aren't just discarded, right? They don't to starve to death. It was very useful on a society-wide level, but not so great for personal well-being because you have this kind of just like cycle of abuse where the parents say, "Okay, it's my turn. I suffered all the kind of - like I needed to go obey. Now it's my turn to make you obey." And nobody's really happy.
Steve Sima
So how did you jump to that conclusion? Because I feel like a lot of people have children as a "I won't die alone" kind of insurance?
Derek Sivers
To me, it's just clear thinking. It's respecting another person's life as an autonomous, fully featured human being, not as an object in your world. I would have a harder time understanding how somebody thinks that their child is some sort of object to their subject. How can you combine that with love? How can you love someone, yet ultimately think of them as an object to serve you? I don't get that mentality. So yeah I wrote that in the book, and I tell him often, "You owe me nothing. If you go out into the world and I never hear from you ever again I will be happy that you must be having a great time. If you're too busy to contact me, that's amazing!"
Steve Sima
You followed up by saying you finally start to appreciate family once they're not forced upon you. That hit me so hard because i know so many chinese parents who use this ancient art of guilt trip in order to get their kids to do things. "Look how much dad sacrifices for you. Look, look at mom sweating over this hot oven, making you soup all day!" Whatever it may be. And then it just drives the kids absolutely miserable. But then, but then it will have to come with like, oh, this is unconditional love from my part. But if, if love needs to come with obedience and what was it? The, what is it? You ask a Asian person, "What's your retirement plan?" and they say, "What do you mean? You're my retirement plan!" So that that one hit really really hard. This idea that we've got to look out for ourselves in today's world.
Derek Sivers
I heard a beautiful metaphor that if you hold a book too far away from your face it's hard to read, but if you hold it too close it's hard to read. There's a right distance for a book and it's the same thing with your family.
Derek Sivers
But wait, before we declare that as some kind of absolute truth, because it's a cute metaphor: Everybody's got their own family distance that works for them. Just because some book author has a healthy family and is telling you with a finger jabbed your chest how you should be treating your family, that's not true for you. That's one way of looking at it maybe that works for the person saying it. But I know a lot of people that have really abusive families where the best thing they could do is to cut all ties, change their name and disappear and not be found. I've got a good number of friends like this, that I'm very thankful that they don't feel any obligation to serve their abusive parents.
Steve Sima
This idea is very deeply rooted in people-pleasing, right? That for people-pleasers to finally get to the point of, "I am not obligated, I am not beholden to anyone" takes years and years and years. And it's incredibly unnatural to arrive at that. I have these second cousins of mine who -- we have no blood relations. They're cut. We share cousins, but we were not related by blood, but we're basically like siblings and I'm closer to them than I am with some of my blood cousins. And it's just kind of a great example of, you know, blood doesn't really mean anything. It just means that you have an opportunity to be in close quarters with each other and you might form a bond or you may not.
Derek Sivers
Yeah. My boy looks almost nothing like me. And I found that very useful as a reminder when he was a baby that I love him for him, not because he shares my DNA.
Steve Sima
Not because he's a mini you.
Derek Sivers
Yeah, he might as well have been adopted. I would love him absolutely the same. The blood connection is bullshit. Everybody has blood. It's more about the bonds you make.
Steve Sima
Yeah, this is that thing where you see the British upper class men, when their moms die, they never cry at the funerals. But when the nannies die, they're always just sobbing and just dying because blood doesn't override time. If you spend the time, there's going to be a bond. If you don't spend the time, no matter how much blood you have, it doesn't matter.
Steve Sima
You mentioned earlier that you had split up with your son's mother. So you're a single dad by choice. And are you 50 this year?
Derek Sivers
55.
Steve Sima
55, wow. So do you ever worry that when your boy ages out of the house, do you ever worry about being lonely? I think the biggest thing that a lot of people want to have a relationship is to deal with the fear of dying alone. Does that ever bother you?
Derek Sivers
Not in the slightest, because of my situation. Because I put myself out into the world so much and I invite connection and I'm very public and I have this public email address and I come out here on podcasts and I go around the world and I meet people face to face too. As soon as my boy leaves the nest, I'm going to be a lot less lonely because that's when I also throw myself out of the nest. The only reason I'm in this nest (New Zealand) is because of him. So as soon as he leaves the nest, I leave the nest. And then I can go out into the world, into Shanghai and Dubai and Bangalore and Berlin and London and New York and Mexico City. And all of these places where I have hundreds and hundreds of people that can't wait to spend more time with. And I plan on doing that for the rest of my life.
Steve Sima
I ask this because you have this one essay where you wrote about how you and your ex just one day just had an amicable breakup, where one of you said, let's break up. The other person said, okay, and you kind of parted ways amicably. And I think that kind of story would be incredibly unsettling for a lot of people because there's this idea that you know you get married or you find a life partner and once you say i do then that box is checked that uncertainty box is checked for the rest of your life and this idea that one day two people can just grow apart like that i was at a wedding this past weekend a beautiful wedding i cried during the vows the two people were very pure but when the official said this union is forever it's permanent it did kind of hit me like is it um and and not not in a jaded way you know i believe in finding someone committing to them building with them. How do we accept the truth that people may not always feel the same way forever without being like this old, bitter, jaded person?
Derek Sivers
I think it needs abundance. Meaning, just like if you're trying to get fit to be attractive, to attract a mate and you get a mate, it would be unwise to let your health go to shit and get obese and lethargic, not just for vanity, but just for your own health, for your own well-being. It would be unwise of you to do that. Same thing socially. Just because you found somebody doesn't mean you should stop reaching out to make connections. I think of all of us in motion and by constantly reaching out, not just a one-time effort like, "Well, I dated in my 20s and well, now I'm done." It's a constant reach out effort because people keep moving and by continuing to put yourself out there and deliberately meet new people, you're meeting people who are currently intersecting you right now. That in 2025, your interests may be as such, but in 2030, you will have a different set of interests. By putting yourself out there at that time, you'll meet people who have intersecting interests at that point in life. And in 2040, you put yourself out there and you keep meeting people that are intersecting with you at that stage in your life. So you keep doing this so that you have many fulfilling connections in your life, whether those turn into really dear, intimate friends, or just lots of entertaining, shallow friends. Both can be satisfying. I'm going to use the word intimate not in some kind of sex way, but it's a word I've been thinking about, The distinction between someone we call a best friend and just a friend or an acquaintance is the ability to get into the more vulnerable secret stuff that you wouldn't feel okay telling somebody you don't know very well. Some of that stuff we need to share with another person. And maybe we need to share it with more than just our partner. if you've gone and partnered up with one person, there might be a side of yourself that you need to share with somebody else. And again, I'm not talking about cheating because it doesn't have to be sexual. It doesn't have to be physical at all, but just somebody that you can have intimate, emotional, vulnerable conversations with. It's really a great life plan to keep finding those people because you're still in motion and they're still in motion and they'll come and go out of your life. You can have a best friend for five years that just moves on into a new situation and then you find a new best friend that comes into your life for a few years and some stick around forever some don't.
Steve Sima
Yeah my best friend here in Lisbon: Lucia, most incredible person. She moved to New York. She met a great guy, moved to New York at the beginning of this year. And I thought I had a great friends group here. And then it's kind of like if you take the star player off a sports team, the rest of the team doesn't make sense anymore. But then the thing is, that gave me the push to go out and make new friends. And now I've rebuilt a new friends group with some previous friends as well, but a completely new friends group. And I feel like it's the surviving the first one of those that kind of gives you the evidence of like, "Oh, I can do this."
Derek Sivers
Yeah. When my best friend suddenly one day dumped me. And we weren't even in a relationship. It was just a best friend who then got into a relationship and just like one day suddenly called and said, "I can't speak to you ever again." The rug was so pulled out from under me that I was devastated. But it helped me start journaling because all of the things that I used to say in our conversations or turn to that friendship to confide. Now, without the friendship, I turned to the journal to confide, and it ended up being a great benefit for me. I felt like all of these thoughts were being saved instead of just tossed out the window.
Steve Sima
How do you think we can have a continuous pipeline of interesting people coming into our lives?
Derek Sivers
Takes deliberate effort. You got to keep putting yourself out there into uncomfortable situations like you signing up for a dance class. I loved that example. Going to a new place if you can, if you can up and move to a new. Now, hold on, let me take it back. That creates a lot of initial loneliness. I think you just have to keep pushing into new social circles by putting yourself out there, whether that's putting yourself out there online, because maybe with your interests, the other people that are interested in this thing are spread vastly across the world and are not in your neighborhood. Doesn't have to be in person, but then it can take a deliberate scheduling of phone calls or meetups to make sure that those friendships stay active.
Steve Sima
Yeah, it's interesting. Sometimes I'll meet people pretty often, especially people in their late 20s and kind of early to mid 30s who are just obsessed about dating. It's the number one priority in their life. It's the only thing that they ever talk about. They're always talking about it, men and women. And I always just try to say to them, this is the fuel of your struggles in dating, is your obsession with dating. Because if you were out there doing cool shit, you're going to attract cool people who are also doing cool shit. Like time and energy is so zero sum. If you're putting every minute that you're spending on Tinder or whatever it may be is a minute that you're not investing in an attractive life. And therefore, you're just going to be it's just going to be this kind of negative feedback loop of the more time you spend on this, the less attractive you're going to be. And then it's just going to be making you spend more time on it and so on and so forth.
Derek Sivers
Since we're on the subject, I broke up with my last relationship two and a half years ago. And dude, this last two and a half years has been the happiest time of my life, because I'm not wanting a relationship for the first time since I was 14. I actively do not want a relationship. It is such a nice feeling to feel so whole that I'm not looking for another half. And to be so into what I'm doing in life that I'm not wanting to spend a single hour sitting around on a sofa with somebody trying to win their affection. I'm so into my life. It's so liberating to not want a relationship. Like, even if one was handed to me, I do not want one. I'm so enjoying my life as is. Every hour of every day is filled with stuff I love doing.
Derek Sivers
And being with my son - that's a huge part of it. I spend 30 hours a week with him. So that's maybe most of my social time is spent with my boy. And it's just so nourishing, so enriching. It's really nice to not have that hunger.
Steve Sima
In How to Live, you wrote, "we should try to fall in love as many times as possible." Do you think you'll be open to it somewhere down the line?
Derek Sivers
Maybe, but I kind of feel like I've done a lifetime of that. I knew a woman who went to Alcoholics Anonymous and was sober. And she would say "I'm not opposed to alcohol. Like, I don't mind if anybody else drinks. I've just had more than my share for one lifetime." And that's a bit how I think about sex and relationships. I've had a lot of relationships. I've had maybe more than my share. So if I never have another one for the rest of my life, it's still been a really rich life full of so many relationships.
Steve Sima
It's interesting because on the one hand, I completely get what you mean. I mean, in the book, you talk about just pursuit of mastery, commitment. It clarifies your life. It rids you of all distractions. And by being present, by being focused, that's how you end up being happy. Happiness is just being present. So I completely get that. But then there's also just, you know, I want to be a husband. I want to be a father and to love someone and take care of, you know, my family and all this. But I totally get what you mean because, you know, ever since I started rising, it's basically my life now is Rising and bachata. And it's amazing because, what did you call it, funner than fun. I just wake up. I don't need any morning routines. It's just, okay, "Let's work on making Rising better for the community. Let's work on being a better dancer." And that's it. And I don't think I've ever been happier. Whereas I've been in relationships with people that I really, really like, but the rest of my life was a mess, whether it was career or insecurities or other things. And this is much happier. It's just, I wonder how I can have both - or if I can have both.
Derek Sivers
Well, I think it could consider the very deliberate strategy of going out in a focused, deliberate way to seek that with somebody who's also focused and deliberately seeking that. As an example, about three years ago, I went to Israel. I went to Tel Aviv for 10 days, and I met with a bunch of people that were either born and raised in Israel or many that had moved there from other parts of the world for the purpose of finding a spouse. And it was amazing to me that I met three, maybe even four different people that had done this all successfully. They had grown up in America or Argentina, other places, Jewish parents. And two of them were even quite atheist, but always just felt, "Well, I'm culturally Jewish. I'm going to move to Israel to find a spouse, to find a Jewish spouse." And because of this deliberate focus, all four of them did it instantly. They found a great match, and all four of them were married with kids and so happy with their life and saying it was the best thing they ever did. And all of them told me how they did it. And I think once you turn on that intention and you say that you're not just messing around, but "This is what I want. I want a spouse. I want a couple kids. I want to live here. This is the life I want. Who also wants this life?" And then you meet and you compare values. You know, "I'm very adventurous. I'm very stable. This is important to me. I want a traditional marriage" or "I want a very untraditional marriage." You can share these values with somebody and then just very lucidly find somebody that shares your values and wants this. And it was amazing to see how well it worked in practice.
Steve Sima
Yeah, I think the values part is probably the key to all that because sometimes I'll meet someone who's just, they're smart, they're pretty, they're nice, but they're just very kind of like go with the flow people where it's either not much passion about anything other than just kind of a chill life or it's that the relationship is their main focus. So I always get this pressure of like, I am the core of their focus, but this is only one slice of the pizza for my life, which is really uncomfortable because you think someone's just out there waiting for you. Meanwhile, you can't give them, you know, everything that they want. So I guess this is kind of like those Hollywood stars that can only date other Hollywood stars because the other person gets it and has the same lifestyle.
Derek Sivers
If you look on my website from my meetings, you click Tel Aviv, you'll see a fascinating guy named Lucian that is one of these examples of a very deliberate marriage. But what's most interesting is that he told me straight up that he and his wife did not touch each other before marriage, not even a touch. And this was very deliberate because they wanted to make a lucid decision for choosing a life partner. And I said, "Wait, hold on, that's crazy. What if you choose a life partner and then you just have bad sex chemistry?" He said, "Well, look, ultimately, the opposite is more dangerous! That because you have great sex chemistry, you end up being a life partner with somebody based on your great chemistry, but you've got completely different values, but you're blinded to that because you're so blinded by the chemistry! That's way more common, that people get into bad relationships because they have great sex chemistry. And so it's a smarter decision to refuse to touch each other. If what you're really looking for is a life partner, don't touch each other." Find somebody that wants the same thing and you have long conversations about what you want and your values. And maybe addressing potential problems first before you decide to do this. Then you decide to commit. And then you jump into bed. after you've committed. It was really fascinating. It was a really strong argument in favor of this approach.
Steve Sima
In your book you said, "It's illegal to sign contracts when you're inebriated, so you shouldn't be deciding your life partner when you're high on infatuation."
Derek Sivers
Thanks for the quote. Well-put, past self!
Steve Sima
One last thing I want to touch on, in terms of relationships, is you wrote, "Beware of the feeling that someone completes you or will save you." What do you mean by that?
Derek Sivers
What needs elaboration there?
Steve Sima
I mean, I understand it, but I feel like it's a feeling that a lot of people chase without knowing why they chase it, I guess.
Derek Sivers
As soon as I sold my company, I told you that situation where suddenly everything had changed for me. I had this idea of going to India and staying for six months, and it seemed really exciting and really fun and a good challenge. And I called a dear friend and I said, "Can you think of any reason why I shouldn't do this?" And she said, "Yeah, don't do it if you think it will make you happy." Oh that's good. Wow. You could fill in so many things into that blank. Don't go chasing the hot person if you think it'll make you happy. It forces you to address the happiness - or the lack of happiness - in yourself directly before also pursuing something else for its own sake not as a means to an end. So don't go to India as a means to an end to fill some gap in your life. Don't have a baby as a means to an end because you feel that your life is a mess and having a baby will somehow give you a sense of purpose. That's using another person as an object, like we talked about before. Address the happiness or lack of happiness in yourself directly, so that you can do something for intrinsic reasons and appreciate somebody for who they are, not what you need them to solve.
Steve Sima
I thought the quote was just put so beautifully, and I ask that because I feel like so much of what we do, whether it's chasing someone or a career or money or a house, whatever it may be, it's the underlying, if this, then I'll be happy. If this, then I will like myself. If this, then I'll finally be good enough. And the answer almost is always, no, it didn't solve your problems, right?
Derek Sivers
Yeah. Though we should caveat to say: Sometimes doing the thing actually makes you happy! If you've been driving an old crappy car that keeps braking and has no heating and is a constant obstacle in your life, and you get a new car, there are many people in your life who might say, "You know, Steve, getting a new car is not going to make you happy." But you get the new car and actually it really makes you happy! Your life is so much easier now. And this thing, if you commute to work, this thing that you spend so much time in is objectively so much nicer now. It can make you concretely happier. I've found this with where I live. I've lived in crappy little apartments with thin walls, listening to neighbors yelling, or above street corners with sirens. And I've been unhappy and I've been thinking, "If I could just move to a new place, I'd be happier." And I've caught myself thinking that. I said, "Well, don't do it if you think it'll make you happy." But then I moved to a quieter place and I'm so much happier. So, again, you just have to look inside yourself and take on both these different perspectives. And only you will know whether this thing you think you want is just going to try to stick some chewing gum into a wound that maybe you need to fix the wound directly or if it really is the solution.
Steve Sima
I guess that's also a limitation in language as well, because in English, it's just "happy". But in Chinese, for example, what you were talking about with the car or the apartment, we call that快乐 - kwae le - literally fast joy. So more of an ephemeral kind of hedonistic type of happiness, more just in the moment of feeling. Whereas there's a deeper level of happiness called 心福 - xin fu - which roughly means like a calm level of bliss, a deep rooted to the soul kind of bliss. For example, like a loving, supportive marriage is xinfu. Whereas like great, like just like insane sex would be kwae le. You know, and and and there is there's that. But I guess it just comes down to being honest with ourselves about why we're doing these things.
Derek Sivers
Yeah, you know, there are some quite shallow-seeming things that really can give you some fulfillment. Let's take the example of a nice home and having money in the bank. Those are two things from my past that you could say would be shallow pursuits. But I get a deep, nourishing sense of deep happiness from having enough money in the bank. I am so thankful that my past self pursued money strongly so that now it's sitting there in an account earning 8% a year in ETFs. And that's a beautiful sense of stability when something goes wrong in life or knowing that if some future thing goes wrong in life, some brain cancer or whatever may happen, to know that I'm okay. It could seem like a shallow pursuit, but it created a deep happiness. And same thing with some of the past places I've lived. There have been some homes that were really expensive. I rented a really expensive place for a year once that I worried might be some red herring of happiness. That I might be thinking this is going to make me happy. In the name of living a fuller life, like your first question, the reinvention, I thought, "Well, I've never really splurged on a place. I've always scrimped. Just for this one year, I'm going to rent this really nice place." And you know what? For that year, I woke up beaming every day! I would wake up like, "God, I love living here. Man, this is nice. Wow, this is amazing!" And it gave me a deep happiness all year long, every single day. So it's hard to know which is shallow, which is deep.
Steve Sima
I guess financial security is an incredibly deep, deeply fulfilling feeling. Whereas, let's say, something else money-related, like having Gucci bags or something, would be a very shallow pursuit of money. So even within money, there are more fulfilling and shallower pursuits, but it depends on the person, I guess.
Derek Sivers
Right. But there might be a person whose Gucci bag makes them happy every day! Maybe the issue is knowing yourself - to know your own deep preferences and what works for you - instead of just listening to the world telling you what you should want.
Steve Sima
I think this is a really nice segue into money. You have this one quote that kind of froze me when I read it. "Your biggest obstacle to getting rich is the harmful meaning you've attached to it." And by it, I'm guessing you mean money. Can you elaborate on that?
Derek Sivers
I hear so many people say billionaires are the problem. "Greedy rich people. Capitalism is exploitation." There are so many truisms about money where people just say it like it's a known fact. Like a square has four sides and money is the root of all evil. But then that belief is useful if you just want to sit at home with nothing, feeling smug and justifying your inaction. There might be some opportunity for you to go make the world a better place, that as a side effect would also pay you a lot of money. But you might find yourself avoiding that pursuit because you've subscribed to the truism that money is evil, and anybody rich must have stolen that money from others. I noticed this with a friend. Actually, I'll say who it is because it's kind of interesting. You know the song Mad World? "All around me are familiar faces...." The guy who sang that, Gary Jules. He and I were walking down the streets of Los Angeles. He's such a smart, interesting dude. We always would have these wonderful conversations. And we walked by a Starbucks. He had just said he wanted a coffee - we walked by a Starbucks and he said, "Anywhere but there - big corporate place" and I said "You know Gary, if CD Baby keeps growing, i might be that big corporate guy. You can't just look at Howard Schultz and say 'what an asshole' because his thing took off - his little coffee shop in Seattle took off. He did something right. People loved it. And it grew like crazy. That doesn't mean he's a bad person." In the same way that if I started something tomorrow that grew like crazy, it would be wrong of everyone to immediately think I'm an asshole because my thing got successful. I think it can be more empathetic to imagine what it's like to be Howard Schultz or Sam Walton or Bill Gates. Somebody that started a thing, worked really damn hard to put that thing out into the world, and people really liked it and it became a huge hit. That could be you. These people are not necessarily so different. It can be more empathetic to think of it that way instead of the prejudice dismissal of anybody that's successful because they must be evil.
Steve Sima
I feel like anybody who's read Hans Rosling's Factfulness will understand this because our world has objectively gotten better in every metric you can imagine, child mortality, poverty, whatever it may be. That comes from abundance and that comes from making money. It's just there are greedy corporate people. Of course there are. But at the same time, good needs to come from abundance. If we're all just scraping by, we're not going to have anything extra to do any good. And like you said, some people just like to feel smug. And whenever I hear people complain about certain things, I just say, "What are you doing about it? Oh, nothing? Okay, don't talk to me. Just shut up." Because if you're actually one of these people, one of these hippies that's making your own freaking deodorant, I can at least respect that. You are committed, and I can at least respect that. But if you're just talking crap, and then you're turning around and doing nothing, then to me, just shut up.
Derek Sivers
Free Palestine.
Steve Sima
There's another quote: "Charge money to make sure your creations are going to people who really want them. People don't value what's free. Charge for their sake as much as yours." Now, there are a lot of listeners out there who just feel icky or just like some kind of guilt about charging for, especially if it's like an intangible, let's say it's their art or some kind of service. They feel icky about charging. What do you say to that and how do you think we can reframe that?
Derek Sivers
Just like our earlier subject about don't get into a relationship or have a baby because you think it'll make you happy. There's a deeper problem there. If you're deeply unhappy and you're looking for a relationship to make you happy, you need to address that unhappiness in yourself first. So same thing with this low self-esteem that feels that people shouldn't give you money for what you do, for feeling that what you do is not valuable. You need to address that low self-esteem in yourself first and realize ideally that what you're making has such concrete value that even this artwork that somebody could put on their wall or in their headphones would make them so much happier that they would be happy to hand over $10 or $100 or $1,000 for this thing. It's easiest when you're doing something that will also make people money. Like when I was running CD Baby, I had created a place that somebody could sell their music to the world. And it was 35 bucks to set you up in my system. and once you were there, thousands and thousands of strangers were going to be checking out your music and hundreds of them would buy it. So I could wholeheartedly say, this is very worth the $35. In fact, I could probably charge $100 and it would be worth it. I had no qualms about saying that because, again, it wasn't me. I'm not saying give $100, give $35 to me, Derek. It was more like I built a system that you can use to go sell your music. It costs $35 to set you up in this system. And yes, of that, initially maybe $5 was profit, and eventually I optimized it, so maybe half of that was profit. But the point is, it starts with the knowing that what you're doing is concretely valuable to somebody else.
Steve Sima
This is that tail wagging the dog thing, right? Where sometimes I'll meet someone who says, "My goal is to get to a million subs by (some date)." And I'm like, "Why do you deserve the million subs? What have you done? What value are you creating to deserve the million subs?" Back in the day, whether it's Michael Jackson or whomever, they were famous because they were great. And now we have people that are just famous for being famous or famous for being able to hijack attention. Seth Godin talks about how you should be offering so much value that people are tripping over themselves to give you the money and you would, they would still feel like it's a bargain or else they wouldn't give you the money.
Derek Sivers
If you focus not on what you get, but focus on the giving, focus on the generous giving of value, of knowledge, of a service, of a system that you can give to somebody that's concretely valuable to them, that they can and ideally will make it so that the more likely they will use this, the better. So ideally that the more they use this, the more valuable it is to them and you're focused on the value. And what you get is just a side effect. That should never be point. The money, the number of subscriptions in YouTube or whatever, that's like the odometer on your car. That's not the point. You should never be looking at the odometer on your car as the point of driving. It's a side effect of going where you want to go.
Steve Sima
This is one of those things that just takes a lifetime of messing up to realize in terms of sometimes going directly towards the thing is actually keeping you from the thing and you need to take an oblique path towards it like Boeing when they were focused on aviation and making the best planes their profits were just rolling in and then they changed CEOs to a more traditional kind of accounting type CEO that just "okay let's cut costs and maximize profits" and they killed the goose that laid the golden eggs and their profits started going down and then they switched back to the aviation ceo and the profits went back up.
Derek Sivers
You say it's something we have to learn the hard way, but I think it really helps that people like Seth Godin and Tony Robbins - authors like that - people who are putting good ideas out into the world - even what you're doing with this podcast - you didn't have to do this. You're going through the effort of scheduling and putting and editing it and releasing it to help put good ideas into the world. So ideally, some young person listening to this can grow up with this mindset, thinking that the key to business success is generosity and is of providing value, not some kind of scammy, "Here's top 10 ways that you can get a million subs without any effort." Ideally, you put healthy thoughts into someone else's brain to help shape the way they think from the beginning so they don't have to learn the hard way.
Steve Sima
I would love to hear your thought on this because I'm split. On the one hand, I absolutely agree that having these things out there is very useful. But what I find is a lot of they really only help me when I'm ready to hear it. Level 100 wisdom, sometimes you'll try to give someone level 100 wisdom when they're only ready for level 20 and they're just, it's not going to go through their ears. For example, in all of my twenties, I was just chasing hot women and trying to have with as many hot women as I can, because I thought that would finally make me feel good enough because of the attention that I didn't receive in high school. And it took a decade of wasting my time to realize my problems didn't go away. You know, nothing went away. My kind of complicated relationship with my parents, my sort of like lack of fulfillment in my career, none of that went away. You think, you know, getting this girl would, but it didn't. And, but then if I told someone, someone who's like, uh, you know, as Charles Barkley calls it, like sitting in their mama's basement with their drawers on with the cookie crumbs on the belly, who's never had a girlfriend. If I tell them that having sex with hot women or having sexy girlfriends is not going to change your problem. He'll tell me, "fuck you."
Derek Sivers
That's life. That's learning. You could say nobody teaches anyone anything. It's the learning that's the active verb. The student has to pull the information into their brain. You can't force it in.
Derek Sivers
I can tell you one tiny idea that hit me at the right time and changed my life. And it was a book called How to Get Rich by Felix Dennis. And I read it just as I was selling my company. So I didn't need to get rich, but I was just browsing a physical bookstore in San Francisco and saw this title, How to Get Rich, with this audacious cover of a fat bearded guy on a throne with dogs at his side or something like that, looking ironically majestic, called How to Get Rich. And I started flipping through, and it was just an audacious, bold book. and I laughed and I bought it, and it changed my life because it was written by a guy who made $700 million in the publishing industry. Filthy Rich owned many Rolls Royces but didn't know how to drive, had chauffeurs, blew his money on drugs and prostitutes. That's what he said himself in the book. And he kept pursuing more and more money. And then he said, I can tell you now, at the age of 68, filthy rich, if I had to do it all over again, I would have stopped after the first 20 or 30 million, which is enough for anyone for life and I would have spent the rest of my life planting trees and writing poetry. I regret my further pursuits of money. I should have stopped at that point. And I read that just as I was selling my company for $20 million. And it just hit me at the right time. I said, I'm going to take this guy's word for it. I'm going to stop making money now. And I have. I have not made a dollar since 2008. I took his advice. It hit me at the right time.
Steve Sima
Having it in your head, even if you're out making mistakes, I feel like it's very useful because if you don't have the idea in your head, then maybe when you get to that certain pain point, oh, that insight is there. Oh, okay. It wouldn't. You'll just kind of keep going. And I find that sometimes I'll hear some wisdom that I would kind of dismiss, But then if I get to a certain pain point, oh, that's what dad meant. Or that's what, you know, Derek or Mark Manson or whomever meant at that time. So, yeah, I guess they can coexist where you need to be ready for it. But at the same time, having it is definitely better than not having it.
Derek Sivers
Good point. You're right. That's happened just as well to me too, that I took in some wisdom, even from an article. And then when that pain point came, that wisdom came back. Very good point. Thanks for mentioning that.
Steve Sima
So to wrap up, I wanna play a little game. We started off with reinvention. You're known for your intellectual flexibility. What did you say last time? "If I stop changing my mind, I'll be a dead fish." So what have you, let's say in the last year or two, changed your mind on?
Derek Sivers
I'm going to name a few that I haven't talked about publicly yet. You're making me go back through my thoughts as they are now, and with each one trying to compare it to what it was a couple years ago to see what's changed. It's a fun mental walk.
Derek Sivers
Fossil fuels. I recently read a book called Fossil Future that explained that we should not be aggressively phasing out fossil fuels because most of the world still needs them. For the privileged, abundant first world economies that perhaps don't need them, to be dictating that the rest of the world should stop using them literally kills people. There are hospitals in Africa that don't have enough fuel to create electricity to keep an incubator running for a newborn baby, and so the babies die because they don't have enough gas to run the generator, to run the incubator. And to say that they should stop using gas is murderous. So I've stopped thinking of fossil fuels as objectively absolutely bad. That was a big one.
Derek Sivers
I've stopped thinking of the Chinese government as evil, and I can see the line of thinking that has run things really well for the last 50 years. I admire it now, whereas I think it's villainized by the American media because maybe the governments are at odds with each other over some things. But the people of China and the people of America have no qualms. In fact, I find Chinese people in general very similar to Americans in general, a very similar entrepreneurial, ambitious energy. It's really, really kindred-y. And I admire the way that the Chinese government is doing things, whereas I didn't used to. So I read maybe five or six books about understanding the CCP and Xi Jinping's approach to things. And I think I get it more now and I appreciate it.
Steve Sima
I guess this is kind of related to your useful not true book. This is a useful not true idea. A friend of mine told me about this book title that I never read the book, but it's called Everything is Figureoutable. And I just love that. And it just stuck in my mind. I remember reading Scott Peck's The Road Less Traveled. And he talks about how he saw his neighbor fixing a lawnmower. And he's saying to his neighbor, "oh, you're so handy. I could never be like you." And the neighbor, without even looking up, said, "it's because you don't take the time." And Scott got a little offended. He's like, what does he mean I don't take the time, huh? And then he got to his office. And one of his patients, her handbrake was broken. So he gets into a car. And he remembers what his neighbor said. And he lies down in the back seat, on the floor of the back seat. And he just stares at the mechanism under the seat where the handbrakes cables and all those things are. And he just looks at it for about five minutes without doing anything. And then he saw, oh, this connects to that. That connects to this. If I just tuck this thing out of the way and okay, the handbrake works. And realize it's because I don't take the time. And especially, I was a late adopter of large language models, especially in the age of chat GPT. Truly, there is no excuse. Everything is figureoutable. I call this useful, not true, because I think there are just limits in physics that some things can't be figured out. But even Newton's three laws are not objectively true. This is a simple way of explaining things. So pretty much 99.99999% of things are figureoutable.
Steve Sima
And if you want to just sit back and be a victim and complain about whether it's, I don't know, men's fault or white people's fault or whomever, you can do that. You're just going to be more miserable. Because I have this friend of mine. He's an Indian guy. his part of South India, he says, genetically, they have a more of a propensity to put on belly fat because of starvation. So they are more adapted to starvation. So he's an overweight Indian guy living in a continent in Europe, that's pretty racist to Indian people. And so dating is not easy, but he's lost, I think, like 50 pounds, and he doesn't make any excuses. I respect him so much because it's just like he can complain about racism or he can just make his life better. And he's like, everything is figureoutable. So that's been an incredibly powerful, useful, not true belief.
Derek Sivers
I love that. In fact, I think we should stop there because it ties together last conversation and this conversation because getting rich is something you could do. That anybody listening to this, the skills of making money are figureoutable. And you learn about it and you go put yourself out there and you do it. And oh, my God, it works. And suddenly you have or eventually, let's say not suddenly, eventually you have a million dollars, then ten million dollars in the bank. And suddenly you are one of those people that you had othered and thought were a different breed of people. But it can be you. And same thing with fitness. And I love that you brought up dancing in the last episode. People who dance, they seem like a different species. I will never be one of those species. No, but it's something you can take a few lessons and learn how to do. Drawing by hand. Getting fit, getting rich. Being a great parent is totally doable. It's not that hard. You just catch yourself at those few moments when your temper wants to yell, but you bite your tongue and you think what's the right thing to say now and you say the right thing and voila, you're a good parent. All of these things are figureoutable. All of these things are doable.
Steve Sima
What did you say? "The only difference between the successes and the failures are that the failures gave up."
Derek Sivers
Yes. I love that idea that there is no such thing as failure until you declare it to be over. Until then, you're still just trying. Say you want to write a great novel. You haven't failed until you've stopped trying to write a great novel. Until then, you're still just trying. You're in the process of writing a great novel. It's only at the point when you say, "I couldn't do it. I failed." What that means is you've stopped. If you don't stop, then there is no fail. You just keep trying.
Steve Sima
Okay, well, this has been fantastic, Derek. I mean, I can talk to you for hours and hours, and you are just a wealth of insights. What are some new things that you're working on right now?
Derek Sivers
I don't know. I'm learning Chinese. That's a huge thing. In fact, it's really funny. I just learned 快乐 this morning, two hours ago. I had just learned that, and you're like, "There's this word, 快乐" I was like, "I just learned that this morning!" Anyway. And I'm building a house. And I'm learning a whole new way of programming by having the PostgreSQL database generate the HTML directly. It would be way too nerdy to go deep into that, but that's just what I'm working on now. So I'll leave it at that.
Steve Sima
Great. And where can people find you?
Derek Sivers
sive.rs
Steve Sima
Derek Sivers thank you man really appreciate you
Derek Sivers
I love that we have a similar pursuit I actually think we're quite kindred-y in our pursuit of exploration and self-improvement I think it's really cool that you and I have a similar approach to life and this whole conversation I felt like could have been flipped around and almost anything either one of us said could have been one of us saying it. So really great to get to know you better. Thank you.
Steve Sima
100%. Thank you, man. Appreciate you. Thank you.