Derek Sivers

Run Your Life

host: Andy Vasily

International education expert and I talk about world perspectives, curiosity, prejudice, and a mental sweep.

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Transcript:

Andy Vasily

Derek, this has been a long time goal of mine and a dream kind of to have you on the podcast because I’ve listened to all of your talks, I’ve read your books, I’ve followed your work and I’m really moved in many ways by the work that you do and the humor that you’re able to infuse in your life narrative is really important and you talk about humor in your writing and the importance of humor and infusing humor in our approach can lift us up, you know. So in advance to the conversation, Derek, I really want to thank you for your time. I know you’re very busy, but I sincerely thank you for your time and energy and your willingness to come on my show.

Derek Sivers

Thanks, Andy. I’m looking forward to it.

Andy Vasily

Yeah. And before I always talk about on the podcast, the conversation before the conversation and we spent a few minutes just kind of sharing some experiences and you know my past, I’ve shared with you that we’ve lived in and worked in six different countries and this is one of the themes you always talk about is the importance of travel and taking on a worldly view and being open to new experiences. So I know we’re going to unpack that today, but...

Andy Vasily

Can we just start off with you telling us who you are, the listeners, who you are and anything you want the audience to know about you to start off.

Derek Sivers

I like how you slipped my book title into the introduction itself. So my name is Derek Sivers. I was really just a musician. I went to music school. I didn’t even go to a normal university. I just went to a music school from the age of 14 to 29. All I cared about was music. I wanted nothing else in life than to just make music. You couldn’t even get me to read a book. I had no interest in travel or any of that, but then I was pretty successful at it. That’s actually the first time I went to Japan is I was the guitarist for Ryuichi Sakamoto when I was 22 years old in 1992 and if you search YouTube for Sakamoto Live 1992, you can see a bunch of videos with me with long blonde hair playing guitar for Ryuichi. And then as I was selling my music, I had friends ask if I could sell their music for them too because I had made a website that could sell my music and so I accidentally started a business called CD Baby and I ran that for 10 years. It was the largest seller of independent music on the web. This is from about 1998 to 2008 and after 10 years of that, I felt done. So I sold the company, walked away, but I didn’t need the money so I put all the money into a charitable trust and kept none of it for myself. People think that’s weird. To me, it just made logical sense. And then I never intended to write a book, but then Seth Godin in 2011 said, "Hey, I’m starting a new publishing company. I want you to be my first author." And how can you say no to that? So I wrote a book in 11 days called Anything You Want, which is my story about how I started, grew and sold CD Baby and the lessons I learned, usually sharing my most embarrassing mistakes and things I did wrong. And that did really well. So people seemed to want more books from me. So I dove into that because I’m just a huge fan of books. My role models are all authors. My heroes are authors. And so I started writing books. So my fifth one just came out called Useful Not True.

Andy Vasily

Great, great, short read, powerful, to the point. Really beautiful messages in there. And I’ll give you an example. Today, when you talk about the concept of change, you know, so I was preparing for this, my dog was getting groomed, his haircut at a little local shop, and I went to the cafe next door for an hour just to kind of prepare more for our interview. And I wanted something chocolatey, because I’m a chocolatey kind of guy, right?

Derek Sivers

And you’re in Belgium.

Andy Vasily

Yeah, right. Exactly. So I had a cafe latte. And I was like, "You have anything chocolatey?" And I don’t speak Dutch. Learning Japanese, my limited Japanese, I mean, my Japanese was okay was hard enough. So I never took on another language after that. But I said to the clerk, "Do you have anything chocolatey?" And she said, "Oh, no, we have this rice tart." And my gut instinct was like, "No way, not touching it." But then I thought, "Oh, Derek would not be happy with that. I have to try that out. I’ve got to be open to it." So I said, "Yes, I’ll have it." And it was actually really good. So that brings me to this idea of change, you know, and all the things that you’ve learned about that. But before getting there...

Andy Vasily

I want you to imagine that I’m a fly on the wall in your grade three or grade four classroom. Okay? And I’m just looking in and I’m seeing Derek, the grade three or grade four student. What kind of student would I see? And what’s a story you can tell from that time that kind of captures what you were like, and maybe even highlight some of the strengths that you might have possessed that went on to serve you so well in the work that you’ve devoted yourself to? I always like to go to early days to kind of set the frame to learn what people were like. So take that in any direction.

Derek Sivers

The only notable thing from that time was that I understood math. And when the teacher was explaining algebra, that like, X + 7 = 11. I said, "Well, why do you use x?" And she said, "Well, it’s just what we do." I said, "But it could be anything, right?" She says, "Yes, it could be anything. It could be ABC." I said, raised my hand again. I said, "But if it could be anything, I mean, couldn’t it be the picture of a cat or a tin can?" And she said, "Yes, technically, it could be the picture of a cat or tin can. It’s just a placeholder." So in all of my algebra homework for the rest of the year, I just used little drawings instead of XYZ. And when I think back about that, I think, "Yeah, that was a pretty cool kid, insisting on finding a different way to do things back then." But you know, I don’t know about this looking back that far thing, because it seems like we like to think of ourselves on some kind of trajectory, like my life is a story and it began here. But honestly, I don’t think that there’s any line connecting moments in time. And I think me now telling you that story I just told you, is back projecting a narrative onto the past that really wasn’t there. It was just some scattered little moments. And maybe that’s one that I’ve remembered because it fits into some self identity that I think is cool. But maybe there are 88 counterexamples that are not cool. And I just didn’t remember them because they didn’t fit into my narrative of who I think I am.

Derek Sivers

I think I didn’t really start becoming me until I met my first best friend when I was 12. Until then, life was quite solitary and just little tiny moments of doing things. But once I had my first best friend, then I had a witness. And we could tell each other all of our thoughts and share ideas and tell your stories of the past and get somebody to hear them and echo them and somebody that saw the real me. Feels like life began at my first best friend.

Andy Vasily

Yeah, that’s beautiful. And if I double click on what you just said about the algebra example, what I see is an inquiry mindset. I see a strength there. I really do. Because in education myself, the work that I do is really instilling student agency and helping teachers understand the importance of differentiating learning to allow entry points for all students based on their awe, their wonder, their personal connections they’re making to their learning, which means that we have to create the conditions for an inquiry mindset. So we have to invite students, we have to create the conditions for questions. Back in the day when you and I, I think you’re 55, 56. Yeah, I’m roughly the same age. So we grew up in the Styx era and Van Halen and all of that and Brady Bunch. Questions weren’t, it’s not that they weren’t permitted, but you just listened. You just took in what the teacher said, you listened. But to actually ask questions like that to me reflects an inquiry mindset, which connects deeply to all of your work on curiosity, remaining curious and open to experience.

Andy Vasily

So I kind of, I understand what you’re saying about the through line and the neat trajectory. But sometimes I think that we can pull on certain strengths that are within us, held in our heart, as we navigate the world in all chaotic ways. You know, we bring some of those strengths with us. But do you see a connection there? Maybe in terms of inquiry and being curious?

Derek Sivers

Maybe, but only because I’m drawing that line. I really do see our past more as like looking up at the galaxy of the stars. And it’s just a billion points, or however many you can remember. You have a billion, a million little memories. And kind of like ancient people drawing constellations to say, oh, look, there’s Orion’s belt. Oh, see that? That’s a big dipper. We draw lines connecting the moments in our past. But the lines are our creative thing we’re putting there. They’re not necessarily there. Somebody else from a different culture could say, Orion’s belt? No, that is the snake of Mjolnir. And tell you that it’s something different. And so same thing with your past, that we have a past with a thousand little events. (I’ve just diminished from a billion to a million to a thousand.) And we connect them, we tell some kind of story. We say, oh, well, you know, I just wasn’t really a popular kid in school. And you tell some little sob story, you say, this is me. I was always rebellious. And you’re the one drawing those lines. But somebody else observing you, one of your former classmates could say, what do you mean you weren’t popular? You were the one that we all looked up to. Where did you make this story that you weren’t popular? You clearly were. And we weren’t making fun of you. I think we were jealous of you. And somebody else could tell the flip side of a story that you’ve been boo-hooing to everyone. So I don’t like telling stories of the past. Or rather, if I do, I know that what I’m saying is not necessarily true. It’s just one possible perspective.

Andy Vasily

Yeah, which comes alive in the writing. And I was really thinking about that in both books. Useful Not True. Taking on our own perspective, but perspective taking. And how what we believe to be true is true based on what we believe, but it’s not necessarily true in the bigger picture of things, because everybody has their own so-called truth, right? And I see that in your writing.

Andy Vasily

And one of the things that I really enjoyed double-clicking on was that idea of your openness to changing what we once believed, right? And I really do want to ask you, maybe some of the listeners have heard of Cricket and Clover. Maybe they’ve heard the Tim Ferriss episode, right? But I’m guessing that probably many listeners haven’t heard anything about, or they have no idea what I’m talking about when I say Cricket and Clover. But that is a perfect example of something you now love that you once hated and even wanted to kill. And I think it’s a very powerful metaphor. And I want you to share that story, but also the bigger metaphor that you’re hoping people will pull out of that too, maybe contemplate in their own lives.

Derek Sivers

Yeah, I mean, you know, if my books have done nothing else but make you get that rice treat today, then I’ve done my job.

Derek Sivers

The idea is that when you notice that you have a prejudice against something, if you just have an aversion to opera or baseball or Saudi Arabia or whatever it is that when you hear it, you think, "Ew, yuck, no, count me out, no way." And just this instant revulsion. Usually to me that means there’s some kind of blind spot going on there. If you have such an instant revulsion, it’s usually because you don’t know enough about it. It’s the essence of racism. It’s like, "Whoa, weird person that looks nothing like me. No, I don’t trust you. I don’t get you. What’s with the turban? I don’t understand. No, no way. I don’t know why you have this dot on your forehead. No, I don’t know those people. I’m not going to go there." That’s a lot of people’s natural reaction to things is if it seems so strange, you just have an instant aversion. One of my favorite life lessons is to lean into that. Like, first you have to notice it in yourself. And then when you notice it, try leaning into it, like steer towards it and go into something that you have an initial instinct against and get to know more about it because it’s usually probably more nuanced. It’s not so clearly black and white. ("That’s just bad.") You need to learn more about it. Maybe the reason you don’t like opera is you haven’t tried to appreciate opera. Maybe you haven’t really sat and watched a baseball game and seen what’s cool about it.

Derek Sivers

So, rats. I used to live in a basement apartment in Boston right next to the trash room and rats were the bane of my existence that year. Rats on the stairs. I had to walk over rats. There were rats right outside my door. There were rats in my ceiling at night as I was trying to sleep. I’d hear like right above me and there was a hole in the ceiling that I knew at any time a rat could like slip and fall during the night onto the ground and I’d be waking up by rats chomping on my fingers. I don’t know. So, I killed many rats that year. I was 18 years old. It was my second year of college in Boston and I killed many rats with great glee. I tossed their dead little corpses into the garbage with vengeance. So, just nine months ago, we had a pet mouse that died and it was really sad and then my boy said, my boy was 12 at the time, said, "Can we get a pet rat?" And I was like, "Pfft. Yeah, right. Ha ha. Very funny." And dismissed it. Then a week later he said, "You know, I was really sad that you just shot down my idea of the pet rat. I mean, they’re really cute and wonderful." I said, "Wait. I thought you were kidding. You’re serious? You seriously want a pet rat? A rat? Are you sure? They’re nasty, filthy, disease-carrying things that chomp on you. That’s not a pet." And he said, "Dad, just look at the YouTube videos. They’re really good pets." And I went, "Alright, I’ll watch the videos." And sure enough, I was totally wrong. They are great pets. They’ve been maligned. They were in the wrong place at the wrong time carrying the wrong disease. But actually, rats themselves are wonderful. The difference between wild rats and pet rats is the difference between wild dogs and cocker spaniel. Pet rats are sweet, clean. Like cats, they poop in a litter box. They control their bowels. So they always, like when they need to poo or pee, they go to their litter box and sit there for a minute and do it and then come back out. They are soft and cuddly and really affectionate. And yeah, we got two pet rats named Cricket and Clover. And they’re twin brothers. Usually can’t tell them apart. And they’re so sweet and affectionate and I love them. And you know how it is when a parent gets a pet for a child, it really means it’s the parent getting the pet. The child plays with it a few minutes a week. But I play with those rats six times a day. Every time I get up to have a cup of tea, take a break, go to the bathroom, whatever, I always go over to the rat cage and pick up my little boys, and they’re so sweet and I love them.

Andy Vasily

My buddy sent me a picture actually from Japan. His name is Scott McKeeman. He’s a big fan of your work. So he sent me a picture. I don’t know if it’s Chloe or Clover or Cricket, but this is the photo I’ll just show you right now. So you can see this. Can you see that?

Derek Sivers

Licking my head. That’s Cricket. Cricket likes to lick my head when I’m reading a book on the couch or whatever. And if I let them out in the living room after they’ve pooed and peed in their litter box or whatever, I’ll just let them run free in the living room. And Cricket very often jumps up onto the couch, climbs up me and then sits there and goes sip sip sip (licking noise).

Andy Vasily

Pretty big too.

Derek Sivers

Yeah. They’re chunky boys.

Andy Vasily

I connect with that so much. In your last episode with Tim Ferriss, you gave four other examples of why this has been such a happy year for you because you’ve changed your mind on five things. Probably more than that.

Derek Sivers

Reversing a prejudice. I think there’s no deeper joy than reversing a prejudice. That if you used to just be instinctively against something and you get to know it more and now you like it, wow, it’s such a deep joy to feel that because it makes you think about your whole life. What other things am I initially against that I could be for next year?

Andy Vasily

Yeah, for sure. How I connect to that is having lived in Japan for 10 years and Saudi for eight years. In Japan, there’s an expression, I don’t know if you’ve heard of it, shogunai. Shogunai is an expression which is, "It can’t be helped. It is what it is," kind of thing. There’s a couple of stories that I want to share, just quick stories to illustrate this point, but I hated shogunai. I loved Japan and the culture. I played American football, so I was on the American football team in Hiroshima. It was all Japanese players and myself. There was one other foreigner that played. We would go to games and play in away tournaments. I had this belief that the refs, because I was a gaijin, that I had this belief that the refs would just call penalties against the foreigners. It seemed true to me that we were just getting called on penalties left and right. We were playing in the national championship at the Tokyo Dome. We did get a bunch of penalties called on us and the winner of that game would go to Paris for the world championships and play near the Eiffel Tower. There was a lot at stake, but we’re getting these penalties. At the end of the game, I was livid. I was furious. My Japanese teammates were like, "Andy, shogunai, shogunai." I’m like, "Fuck shogunai. It can be helped. This is bullshit." Just like a barbarian just going off. That expression would always annoy me so much because from my foreign eyes, many things can be helped, but they would say shogunai oftentimes to dismiss that idea that there are things that you can do that would change the outcome. And then inshallah is the same thing in Saudi.

Derek Sivers

I’m so glad you made that connection. I was just about to say that. All right. Sorry, go ahead.

Andy Vasily

Yeah. You go to government affairs or you’re handing in actually to come to Belgium. I had to get the bloody Ministry of Health to stamp my medical report in Saudi. They kept putting the wrong stamp on it. Time is working against me. I’m under a lot of pressure to hand in the paperwork. It’s one of the last times I’m saying, "Please, can you get this right?" The guy’s like, "Inshallah, inshallah." I didn’t say, "F inshallah." I just was like, "I don’t want to hear that right now. I don’t want to hear that. I just want to hear, "Yes, you will get it done." And then he says, "Trust in the process. People are working behind the scenes to make this happen, inshallah." And right away, I connected with the shogunai thing and my mindset being, "Fuck shogunai." There’s other ways to look at this, but in the end, shogunai and inshallah are beautiful illustrations of cultural thinking. In Japan, it’s like once it’s...and Saudi too, once it’s gone, it’s out of your control. There’s nothing you can do about it. You just accept. It’s about acceptance and maybe a bit of patience, but I changed my mind about those two things and now I realize the beauty behind it. That’s what I wanted to share in connecting on to what you had said.

Andy Vasily

Based on your travels, can you give some examples of things that really maybe you held hard and fast to, but then you completely changed your mind on?

Derek Sivers

Oh, in short, Confucianism. It’s oversimplified, but when I first moved to Singapore, I met many 30-somethings that said that they wanted, they used to want to be a musician or a poet or a painter, but their parents told them, "No, no, no. You need to go to law school. You need to go to med school. You need to get an engineering degree." And so they did. And now they have a well-paying job at a big company or they’re a lawyer or a doctor, whatever. When I first heard this, I said, "No, you need to follow your dreams. You don’t have to do what your parents say. Just because they said they want this for you doesn’t mean that’s what you have to do." And a few people pushed back and it took maybe a year of living there and meeting a lot of Singaporean people. It was very social when I lived there and I met with probably 500 people one-to-one like this over lunch and most of them Singaporean. And eventually I got to understand the mindset better. And now I can see the benefit of social harmony and your personal desire to make music or poetry or something is not that different from your desire to eat the ice cream or have your parents buy the Batman toy for you. It’s a passing feeling that doesn’t always need to be honored. And sometimes doing the right thing is the right thing to do when somebody with a zoomed out perspective can see what is really best for you. "Trust me, you’ll have a better future. Go get that engineering degree. I can see where Singapore is going in the long term. You live here in Singapore, this is going to be to your benefit. I know you want to make music. Just do it on the side of something. Don’t try to go be a professional musician. Get the engineering degree." I understand that viewpoint now. Similarly, I understand the Chinese government’s viewpoint. I’ve read a couple books that try to describe their point of view and I never really understood that the Chinese government is very cradle to grave, top to bottom. You have a fight with your landlord, the government gets involved. The toilets aren’t working in the apartment building, the government gets involved because one tenth of the adult population is employed by the government. And they get involved at every little local level. It’s considered to be the government’s job to take care of you from cradle to grave, every aspect of life. A friend of mine told me about the data surveillance thing, saying, "You got to understand the Chinese government, they’re mostly engineers. And like most engineers, they want all the data possible so they can make the best decision. So all the things about having cameras everywhere or monitoring the internet, they’re just collecting all the data they can. It’s not big brother, horrible ill intentioned. They’re trying to help their citizens have the best life they can by looking at what’s going on." And hearing these mindset perspectives, I think helped me go like, "Okay, I was initially against that, but now I get it. I can see the benefits." Especially if you go to China, you go to a place like Shenzhen, Chengdu, Shanghai, and you see the amazing quality of life in these places. You go, "Okay, it’s working. Proof is in the pudding."

Andy Vasily

Absolutely. We were there in Nanjing, I told you, for five years. So we spent a lot of time in Shanghai, Shenzhen, and Shanghai, which is such a beautiful, Shanghai is an amazing city, right? And we had the best experience there. It was an amazing experience. We worked with Chinese people. We got to know the Chinese very well at the school that we worked at there and just life on the streets in China is so vibrant and full of life and so many greeted with so many smiles and so much respect. It’s so much curiosity towards us too, like kind of looking at us like, "Who are you and what are you doing here?" You can tell that they’re probably thinking, but in the best way possible. So you hit the nail on the head when you said, "Sometimes we have preconceived notions of what something is going to be like." And that’s really based on nothing until you actually start to learn about it. As you said, you learned about Dubai, you changed your mind about Dubai and you learned about the history of Dubai. And then you talk about sitting in the Dubai Mall. And I’ve been to that mall many times, looking at all the different nationalities, pass by. And with Dubai, there’s no central kind of hub. Some places will have a central hub and it just seems so spread out and so hard to put your finger on it, but it’s such a cool place. So you changed your mind about that. You’re constantly challenging people to really think about what they might consider changing their mind on. And you use a lot of stories as provocations for that.

Derek Sivers

Well even going back to you asking me about fourth grade, even changing your mind about your own past. There are a lot of stories in your past that you’ve probably told yourself are just fixed. "This person wronged me." "I was treated unfairly here." "I was great at this." "I was bad at that." You can rewrite those stories too.

Andy Vasily

Absolutely. Right. And I think that leads me into How to Live. And can you just share with people, what do you want the listeners to know about this? And then I want to do something called Two Stars and Two Wishes, which is I connected with a lot in that book for sure. There were some things, it’s not that I didn’t connect with, but it’s kind of like, "Hmm, you know, you’re making me think, and I want to talk to you about those two wishes to unpack them further." But before getting into that, can you just share what you want the listeners to know about this amazing book?

Derek Sivers

Thanks. In short, it’s a little book where every chapter has a very strongly opinionated answer to how you should live your life. And every chapter disagrees with all the other chapters. So it’s like reading 27 little opinionated philosophy books in one little book. And it’s only 112 pages. So each chapter is only three pages long. And it’ll say, so one chapter, for example, will say, "Live for the future. Here’s why living for the future is the way. It is the only way to live. Today is just in service of tomorrow. It’s all about building the brighter future, ideally as long as possible so you can make a better world for your children and your grandchildren and make the world a better place. This is how to live." And it stacks up the argument why. And the very next chapter will say, "Here’s how to live. Just fill your senses with every moment. There’s no such thing as the past. That’s just your memories. There’s no such thing as the future. That’s just your imagination. The only real thing is now. Live fully for the present moment. Look to the example of the animals of the world. They’re not living for the past or the future. They’re just living for right now. And even if what you feel like doing right now is building a dam, then do it, but not because of the future, but just because this is what you feel like doing now." And makes up the best argument for why you should live now. And then the very next chapter will say, "Here’s how to live. Get rich. Money is a neutral indicator of value. If you just focus on getting rich, you’ll be being valuable to the world." So it’s a head-spinning, confusing book that does not resolve itself. It just has 27 chapters in no particular order really, except I tried to make each one have the biggest contrast with its adjacent ones. And at the end, there’s just two photos. One of an optical illusion of a duck and a bunny, and one of an orchestra seating chart. So the title of the book is "How to Live, 27 Conflicting Answers and One Weird Conclusion."

Andy Vasily

I saw the duck and I was like, "I don’t see the bunny. I don’t see the bunny." And then finally I was like, "Oh my God, there’s the bunny. There’s the duck." But for some reason it took me a while to see the bunny. But I think you eloquently described exactly what you’re trying to do. You’re not saying this or that, you’re saying both. And neither is right or wrong. And I learned that early on because you’re talking about traveling the world and I was like, "Oh my God, I connect with this so much." And I sent you an email saying, "I love this." It’s sharing about the world and travel and openness to experience and then all of a sudden it’s like, "Stay in one home. Don’t move. Stay there for the rest of your life." And I’m like, "Huh? You just told me to travel the world, man."

Derek Sivers

But that’s the whole point. For one person staying at home and building a life and living that path is the right choice for them. For another person, it’s traveling the world. For one person it’s different. What are different times in your life? It’s different approaches for different purposes. Each approach to life is in service of a certain value. If you want a deeper connection to one place, then how to live is to commit to one place.

Andy Vasily

Absolutely. And that’s the beauty of it. So you see both perspectives and that’s what you really emphasize in all of your work is my perspective taking on the other perspective. And how can we not grow as a person and become richer in experiences by taking on this type of mindset.

Andy Vasily

So two stars and a wish. So the first star for me that I want to share with you is, again, I connected with a lot of the chapters, but certain points really stuck out to me probably based on my own narrative, my own experiences. But page 47, here’s how to live. Follow the great book. Physical discipline helps mental discipline. Align your outer self with your inner self. Cleaning your house helps clean your mind. Change yourself and change the world. And I shared or I saved so many quotes. I have quotes written everywhere. And I immediately, immediately went right to my quote from Mother Teresa. If each of us would only sweep our own doorstep, the whole world would be clean. And Dr. Carl Jung, your vision will become clear only when you can look in your own heart who looks outside dreams, who looks inside awakes. So when you think of follow the great book and those quotes and what you were sharing in that, again, without discipline, the tiny things in your life will be your downfall.

Andy Vasily

If you had a broom in your hands, what shit would you have to sweep away in your own life? Like looking back, what shit did you have to sweep away to better clean your own doorstep? And how has this helped you to be better for the world and the people you serve?

Derek Sivers

Here’s one. It’s doing the right thing, not the emotional thing. The role model is a good hotel concierge. So that if you come stumbling in drunk and throw up in the lobby, a good hotel employee does not yell at you and punish you. They say, "Oh, sir. Oh, sorry. Here, let me help." And if you say at six in the morning, you wake up at a nice hotel and you say, "I want some coconut ice cream." A good hotel concierge does not say, "That’s stupid. You shouldn’t want that. There’s no such thing." Good hotel concierge would say, "Hmm, okay. Very difficult. Maybe we could find this. Let me see what I can do." I just gave terrible examples there. That was really awful. I’d almost wanted to scratch those for the record.

Derek Sivers

The real point is when somebody’s being a kind professional, they mute their own emotional authentic reaction. They keep that to themselves and what they show you is the right thing to do, the right thing to say, no matter what they’re feeling inside. So the reason I used a hotel concierge as an example is I imagine that in those moments, if somebody comes and throws up on the floor, asks for coconut ice cream, what they’re really thinking is, "You idiot. Oh, God, look what you’ve done. This is going to take me an hour to clean up. Nobody can find you coconut ice cream at 6 a.m." But outwardly, they say something kind. And I think of that example in our lives when you encounter somebody that’s done something that you think is stupid or somebody that you think is making a wrong decision or being idiotic, you want to give them a piece of your mind and tell them what you really think. And I’ve learned that it’s better to act like a professional hotel concierge and keep that to yourself and think of what’s the right thing to say to this person.

Andy Vasily

Did you learn that through practice, obviously, or did it just take some time? Because you’re dealing with people all the time, right?

Derek Sivers

Yeah. Well, I think I learned it more when I was running my music distribution company called CD Baby. I had 180,000 musician clients that would sometimes get emotional and irrational and send us an album, we’d put it up in the store. And then a week later they’d change their mind and they want to change the tracks or change the album art. And of course, my selfish thing was like, "No, you can’t do that. We already did all the work." And instead I’d say, sometimes I’d write the nasty email, then delete it. And then start again and say, "No problem. I’ll be happy to help. Just want to make sure you’re happy." And I’m so glad I did that. And then it filtered out into everyday life as well.

Andy Vasily

So taking on a non-judgmental kind of stance.

Derek Sivers

Oh, no, I’m fully judgmental internally.

Andy Vasily

No, no, internally, but externally with withholding that knee jerk reaction. Right?

Derek Sivers

Yeah, which is against the current trend of valuing "authenticity", where we’re valued for, "being your real self saying what you really think." And I know a lot of people on social media are rewarded for being jerks to other people. And I think it’s unfortunate and unwise.

Andy Vasily

Yeah, for sure. One of the wishes I have is to kind of unpack randomness on page 28. And I think it also connects with the part from Useful Not True about beliefs. And what you say is, we think we see patterns and causes, really there are none. We think events are meaningful, really they’re just coincidence. We’re not used to the logic of probability. Life is more random than it seems. So why that stuck with me and why I want to unpack that a little bit is, again, I’ve got a short story is that I was almost killed in Cambodia in an accident. My ulnar artery was completely blown out in the accident and I came close to bleeding out. So I was rushed to a local hospital, this shitty little clinic, right? Australian doctor who had kids at her school was the only physician on that morning. Crazy thing is that last week I was giving a workshop in Malaysia to educators there. And the director of the school was the principal of the school that was in the car with me, rushing me to the hospital, gripping onto my wrist so I wouldn’t bleed out. So you talk about that idea of human connection and full circle back. And last time I saw him, his name is Robert Cody. My wife was a nurse actually. So he had reached into my pocket with the hand that he wasn’t holding onto my wrist with, called my wife and said, you got to get down to the clinic and put the phone up to my ear. And I was like, I can’t talk, just please get to the clinic. And I get out of the car and my blood is all caked all over his body and all over my body. That’s the last time I saw him. Two months after that, I reached out to him to say, thank you so much. You kept me so calm in that moment. He was getting me to talk about my kids and I thank you because if I didn’t have your calm presence, I don’t know what would have happened because inside I was panicking. And I said, one day I’ll give you a hug. And then he emailed me a few weeks ago to say, I’m going to cash in on that hug. I’m going to see you in a couple of weeks. That’s just part of the story. But what’s interesting is that I was in, I had arterial clamps jammed into my wrist, a blood pressure gauge for a tourniquet, four hours, my arms turning dark purple, pains intense. And then all of a sudden they find they need an orthopedic surgeon. There’s none in the city of Phnom Penh. So they find Dr. James Gulligly, who’s a retired Scottish orthopedic surgeon that does volunteer surgeries on landmine victims. And he’s not in Phnom Penh on Fridays, but he was there that morning. And they rushed me to him and he does an arterial ligation, which is just stitch the artery shut on either side. He couldn’t reattach it. So he saved me in my moment of need, great need. Right? Then the second coincidence is that I had to fly to Bangkok to have total reconstruction of my wrist a few days later. But our passports were being renewed in Bangkok because the Canadian embassy was in Bangkok. So we couldn’t fly out. The president of Cambodia’s grandkids were at her school. His daughter-in-law escorted me onto a plane without a passport and got me to Thailand. So pretty cool. But then insurance turns us down and I have to fly back to Phnom Penh and I’m in intense pain. So I was supposed to have total reconstruction. We didn’t. And for whatever reason, insurance turned us down and then we would have had to pay, I don’t know, some crazy amount of money, which we didn’t have for the surgery. And they said, "Oh, you’re going to have to go back." And I’m a complete mess, like anxiety, overwhelming. I think I’m going to die. I’m at the airport and I have a total breakdown before getting on the plane. And I don’t want people to see me bawling. And I go to the corner of the terminal and for the first time I was a kid, I prayed to God and I prayed for like, "Why did this happen to me? And please God, give me a sign that I’m going to be okay." And then I go back and I’m wiping my eyes and I get on the plane and the plane’s packed and my wife is beside me. There’s an empty seat beside me. And this Thai woman comes up and she’s trying to put her suitcase in the overhead compartment. She asked me to help her. And I said, "I can’t. My arm’s bandaged up. She’s sorry." And then she sits beside me and she’s staring at me and she says, "Are you okay? You don’t look okay." And I said, "No, I’m not." And I told her the story and she looks at me like a deer in headlights and says, "You’re not going to believe this. It was my husband who operated on you last week." So Dr. James Gulligly, his wife was Thai and they ran this charity together and she went back and forth a lot. So she was like, "Oh my God, I’m going to tell him when I get home what happened about insurance. He calls me the next day. Those insurance companies are fucking bastards. I’m going to make sure that you get taken care of." And he organizes me for me to fly to Singapore to the top hand specialist and has all the whole thing paid for. Okay. So that’s another coincidence. And then the third coincidence is my wife was the school nurse and a week before the accident, she was looking through brochures on her desk and came across the work of a really cool charity. I was like, "Shit, I’m going to donate $100." That was to Dr. James’s charity. A week later, he operates on me. So when you talk about randomness, I chose to believe and connect the dots in a way that God answered my prayers. I’m not religious. I think I’m spiritual and I believe in the connecting of dots and that if we put good karma out in the world, that it’ll come back to us. And that could have been all coincidence, but I choose to look at it as having deeper meaning in my life. And this goes back to the belief that I have about that story. That’s my belief and that’s how I connect the dots. And that’s what inspires me to think that maybe I was given another chance to do good work in the world. And maybe this is my purpose. And after that, I truly found my purpose. Whereas before I was doing good work, but skating through, just trying to figure things out. So I’m not pushing back on what you’re saying, but I want you to unpack that idea of beliefs and randomness and what you’ve come to understand about it based on your own context and your own story and your own learning.

Andy Vasily

So have you had any big moments that have been a bit of karma, maybe a bit of coincidence or just take that in any direction you want?

Derek Sivers

Sure. And by the way, I know what all listeners are thinking right now, which is, "Andy, you need to get out and live a little."

Derek Sivers

The biggest life lesson I’ve learned about stories in our life, connections we make like that versus randomness, is that neither one is necessarily true. And by necessarily true, I mean objectively, observably, empirically true for anyone everywhere always so that any outside creature or machine could observe it and agree that this is the definitive true answer. You can’t say that these coincidences in your life are true, but you also can’t say that the connections are necessarily true, but you also can’t say that it was necessarily random. Neither one of those points is the absolute right answer. It’s just a way of looking at it. So then you ask yourself, "What’s the point of looking at it in that way? What’s the end result?" So if you look at it as not just a random coincidence but as meaningful, then, oh, wow, it fills you with an intense sense of awe and feeling like you’re a little twig floating down a river of fate and connections and how beautiful to see these connections. But let’s imagine that there was an opposite situation where say somebody grew up with abusive parents that beat them and then they went out into the world and they met somebody that seemed to be the answer, but then that person also turned out to be abusive. And then they were in a horrible car crash and didn’t have the right surgeon and lost their arm. And then they had more bad things. That same person could look at their past and if they felt that it was all connected, could feel whatever is the opposite of awe. They could feel an overwhelming sense of doom, that I am doomed, I am cursed, I am a bad person, the universe hates me. All of these things are connected to conspire against me. The world is against me. That person would be better served by looking at those past events through the lens of randomness. Say actually, I’ve had six bad coincidences, really bad coincidences. That doesn’t mean that everything will not be amazing from this point on. If you roll two dice, there is the chance that four times in a row, you’ll roll two ones. Imagine what you want is the high score, you keep rolling those. It doesn’t mean that the dice are going to keep rolling ones forever. Every now and then, bad luck just happens and it wasn’t your fault. And that lens can bring you so much peace and a useful mindset that helps you go out into the world tomorrow expecting things to be good even though they’ve only been bad in the past. You can say this is not a story. These things are not connected. So both of those points of view, to say everything’s connected or to say nothing is connected, neither one is necessarily true. You have to look at the result in yourself that each story gives and choose the story that serves you now.

Andy Vasily

Beliefs = emotions = actions, which you talk about. And I hear that and I’m glad that we talked about this because there are some people that believe just one path. So again, I’m open enough in my own story to know that that’s the story I’ve created. I’ve connected those dots in a way that’s meaningful to me and I’ve found inspiration through it. But that’s my interpretation of it and I accept that somebody would have a completely different point of view based on their own understanding and their own learning.

Andy Vasily

And what you talked about in Useful Not True: You talk about this idea of being in a workshop and the workshop presenter wrote, life is blank, left a big blank, big blank, big blank, big line, and then challenged everybody to fill in what they felt was the answer. And then you quietly observed during lunch or whatever it was, and everybody kind of sharing their points of view, thinking that they were right. And then you stumbled upon, not stumbled upon, but you had carefully reflected on it and then you figured out what you felt the answer was, which was the right answer. I think that’s really powerful because all of your work is about giving people permission to do just that. Life is blank. You fill it in. I’m not here to tell you how to live your life. I’m not here. I can just suggest different ways of looking at your life to challenge your thinking. But I really see a connection there. So can you just share that story because I love it.

Derek Sivers

Yeah. And I did stumble upon that profound moment where, yes, the teacher right before we broke for lunch said, yeah, "Life is _________", everybody fill in the blank, figure out what goes in that blank. We’ll talk about it after lunch. Goodbye. See you in 90 minutes. And it’s just fascinating to me that sitting at the table with six other people, somebody was passionately arguing for why life is learning. No, look, life is learning. It’s all about this and stacked up the argument why life is learning. It’s clear the answer. And somebody said, no, man, life is love. Ultimately, love is the real emotion that this is what it’s all about. That’s why we’re all here. Somebody said, no, it’s all bullshit. Life is time. Life is the time between the moment you’re born and the moment you die. That’s what we call life. The very definition of life is time. That’s what we call life. It’s the time between birth and death. That’s what life is. And somebody said, no, man, like a recent nouveau Buddhist said, life is suffering. All life is suffering and was kind of echoing the lessons he had heard the previous week at a Buddhist lesson. And I’m usually a talkative person. But I just sat there and marveled at the clash of values and thinking, wait, there’s no way that one of these is the answer. There’s no way that it’s like, no, you five are wrong. This guy that said life is love, he’s the right one. Wait, wait, I mean, sorry, the guy that said life is suffering, he’s the right one. Yep, the rest of you are wrong. He’s right. There’s no way, no way that that could be true. It’s like, well, if none of them are true, then what? I was like, wait, the underline, the fill in the blank is the answer. Whoa, that’s so cool. Wait a second. Hold on. Let me wrap my head around this. The teacher wrote, "life is _______" and asked us to solve that problem. But actually, what he wrote on the board is the answer that it is blank. There is no meaning. We put words into there if we feel like it, because it makes us happy to say life is time. It makes us fulfilled to say life is love. But those are our projections that we’re putting in there. It’s not the answer. And this whole funny idea that we make jokes about this idea of like, oh, you know, "What are you doing figuring out the meaning of life?" We act like there’s an answer. Like the monk goes to the top of the mountain to sit there and meditate for 50 years to figure out the answer to the meaning of life. But there’s not an answer. There’s nothing to figure out. It’s just a blank canvas that we can paint whatever we want onto and erase right again. Whoa. And so, yeah, I got a very smug sense of satisfaction when lunch was done. I went back into the workshop and everybody put forth their arguments to tell a teacher that they had figured it out that life is whatever, giving, life is learning. And yeah, sure enough, the teacher had intended it to stay blank. But that was a really profound moment to me.

Andy Vasily

Yeah, for sure. I mean, I think of, you know, Michael Gervais, Dr. Michael Gervais?

Derek Sivers

No.

Andy Vasily

He has a podcast called Finding Mastery. He was the performance psychologist for the Seattle Seahawks. Pete Carroll’s now moving to LA Raiders, so he might end up going there. But he has this wonderful program called Compete to Create where he, I’ve taken the course a few times, where he unpacks the guiding principles of high performance, right? And what he talks about his life philosophy is every day is an opportunity to create a living masterpiece. So that’s what really drives him in his work. So when you were talking about that blank canvas, I thought about his philosophy and how it’s wise, you know, like we are given opportunities every day to do work that matters, even if that’s impacting one person or a million. Which connects to the other area I want to unpack from page 30, pursue pain. And what you say is, therefore, the way to live is to steer towards the pain. Use it as your compass. Always take the harder option. Always push into discomfort. Ignore your instincts. Robert Plant, the lead singer from Led Zeppelin, and Bruce Dickinson, the lead singer from Iron Maiden, were at a recording studio. Ryan Holiday, I saw him speak in November, and he told the story that they were in a recording studio in the Netherlands, right? And they knew each other, and they got together for a coffee. And Robert Plant is like, "Sometimes the mountain’s just too high. You know, I see the mountaintop, and I just can’t get there, and it just eats away at me." And I think he was talking about his own creative processes tormenting sometimes, like Leonard Cohen as well. Like, it was really hard for Leonard Cohen to create music, whereas Bob Dylan would just pump off these songs in 10 minutes. And Robert Plant was talking about that idea of the mountain being so high, and Bruce Dickinson is like, "Why don’t you just take the staircase one step at a time and enjoy the view? That’s what I’ve done." Right? And it’s that example of pursuing pain. Like, to Robert Plant, that’s painful, and he wants to avoid it. And Dickinson is just saying, "It’s just part of the journey. Just take the steps." But that really got me thinking about the story of your 17-year-old self, which is really powerful. I must admit that I paused there, and I was a little emotional listening to that part of the story, or your story in that part of the book, because you confronted pain head on, and you learned so much through the process, and how uncomfortable it might have felt. Maybe it wasn’t uncomfortable to go knock on that door, but for many years, there was underlying pain and emotional distress that you were going through as a result of what had happened. So would you mind, with the audience, just sharing that story and what you learned about it? Because that is that idea of pursuing pain. That, to me, connects deeply to it.

Derek Sivers

Sure. I’ll give a hint to the audience listening to this that the story you’re about to hear is a story written in the past, a way of looking at the past. So, yeah, when I was 17, I was in a car crash in my neighborhood in Hinsdale, Illinois. I blew off a yield sign and car crashed into me. It was totally my fault. And in the confusing time of police and ambulances showing up and taking us out of the car and taking us away, somebody later told me that, "Yeah, well, guess what, dude? I mean, the woman that you hit broke her spine and she’ll never walk again." I was like, "Oh, God, that is awful." But this was all just a month or so before I was going off to college in Boston. So, I flew from Chicago to Boston and carried this weight with me for years that I could be a joyous, happy person and every now and then I think, "Oh, and there’s some woman in Chicago that will never walk again because I blew off that yield sign. Oh, that is so messed up." I carry that with me. So, for so many years in my mid 30s, I was back in Hinsdale, Illinois and I decided I’m going to go find that woman. Used the good old fashioned white pages because people weren’t on social media at that age and found the woman whose car I hit just showed up at her door, knocked on the door and she answered the door. The door opened, there was an older woman there and I said, "Hi, my name is Derek. I’m the one that hit you in the car back in whatever year that was." And I started sobbing on her doorstep and she said, "Oh, sweetie, sweetie here. Come in, come in. Don’t worry, come in." And she walked me into her living room, walked and took me a second to put this together. I was like, "Wait, what? She’s walking. Hold on. What?" And she said, "You know, don’t worry about it." You know, I was still kind of crying a bit and she said, "That car crash, believe it or not, helped me turn my life around. I was being a glutton. I was a compulsive eater. I was fat." And she said, "I was eating while I was driving and that’s why I hit you." And I said, "Wait, no, I hit you." Because I blew off the yield sign. She goes, "No, sweetie, I hit you because I was eating and not paying attention while I was driving. You didn’t hit me, I hit you." And she said, "Wait, all these years you thought you hit me?" I was like, "Yeah." And then she started crying and she goes, "It’s so stupid, these stories." And again, I referred to this earlier that we all tell stories about our past. You know, "I’ve been wronged," or "I am a champion," or "I’m great at this," or "I have bad luck," "Women just aren’t attracted to me," "Men are all jerks." We make these stories in the past and we hold on to them so tightly like, that’s just true. That’s what really happened. That’s how it went. But it’s usually based off of a misunderstanding or an unfair connection between some random little data points that we connect and just cling on to it and say, "That’s the past, that’s true." So, I think the name of that chapter I made is "The Past is Not True." That just by definition, you can have some true facts. Okay, yes, this car hit that car. That happened, but your interpretation and the meaning of it is never true. It’s just one perspective.

Andy Vasily

Yeah, and that was, at an unconscious level, carrying that type of burden can be overwhelming and then it would surface itself every once in a while and you would think about her. Did it seem like a courageous act to go? Wat was that like for you? Was it just like, "Yeah, hell yeah, I’m going to go, I’m going to knock on the door." Can you just share any kind of feeling that you had going there? Did it seem like an act of courage or the right thing to do?

Derek Sivers

No, I think it just felt cathartic and maybe even selfish. Believe it or not, John Lennon and Yoko Ono, in an interview I read once, gave me a new perspective on the selfishness of unburdening yourself. So, their rule in their marriage was, "If you cheat, you are never allowed to tell me. You must carry that burden yourself forever." And that was such a backwards way of thinking of it. Obviously, here I am 40 years later after reading that, still quoting it, because that’s such an interesting framing of a confession as a selfish unburdening. Like, "I’ve been holding this secret. I need to tell you the truth. I slept with somebody else." And you think that you’re somehow being righteous and congruent and telling the truth and manning up to your honesty and all that, but no, that’s selfish. You’re unburdening yourself. You’re sharing the secret so you don’t have to keep it. And it was so interesting that Yoko said, "No, you’re not allowed to unburden yourself. If you’re going to do something that’s going to be a burden to carry, that’s yours to carry." So, no, I’d say that probably I was in a mindset of unburdening myself to go back and apologize to this woman.

Andy Vasily

Well, and mutually beneficial both ways. You both walk away with different insight and a different perspective, which was so valuable to the both of you.

Derek Sivers

Well, maybe, but I mean, that’s the way it turned out. It could have been opposite.

Andy Vasily

Yeah, for sure.

Derek Sivers

A woman in a wheelchair could have rolled up to the door and seen me and said, "Fuck you. I hate you. How dare you show your face here? That was a horrible selfish thing to do." Actually, that was a real problem in my last romantic relationship a couple of years ago is over and over again, we had such a clash of values around this kind of thing. I would do something that I would think was kind and she’d say, "How dare you do that?" But what? How are you seeing this at all as unkind? So, you never know how somebody else’s value system is going to interpret your actions.

Andy Vasily

Yeah. You talk a lot about that idea of what’s more useful and it’s living in alignment so that you’re aligning your thoughts, words and actions in a way that allows you to take action on things that are meaningful to you. A quote that I want to share with you is from Dr. Jim Lehrer. He’s been on Tim’s podcast and Tim has shared this quote. This quote really stuck with me in my journey and I put it up on our chalkboard wall to remind our kids who are now 20 and 19 about the power of personal narrative. What this says is, "The power broker in your life is the voice that no one hears. How well you listen to the tone and content of your private voice is what determines the quality of your life. It’s the master storyteller and the stories we tell ourselves create our reality." Going back to that idea, what Jim says is we are so shitty with ourselves sometimes and the stories we tell ourselves that we would never want what we say to ourselves broadcasted on the jumbotron of a major sporting event for 85,000 people to see. It’s that idea that this narrative that we have, I know that you looking back at yourself, you don’t stitch any kind of linear narrative because everything just happens and you learn and you grow and you pivot and you learn different skills to continue to move you forward in life but how does that quote resonate with you in terms of learning things about yourself and continuing to learn and changing your narrative?

Derek Sivers

Okay, so I gotta clarify, even though I’ve made arguments in favor of randomness, I very much all the time draw lines in my past to say, "Ah, look at what I’ve been doing too many times in the past in all of my romantic relationships," or, "Oh, look, business-wise, I’ve always taken this approach," or, "I’ve been on a gradual path of opening and opening and opening." All the time I draw lines in the past, in order to see where they go. My only advising against it is to not think of it as necessarily true! That if you are drawing a line through your past and making some meaning of the past, please don’t think that it is the only answer. There are always more answers. There are more ways to connect these dots. Anybody could see. Ask any two-year-old, "Show me different ways you can connect these dots." They’ll show you different ways. So same thing with our past. You can connect the dots of the past and make a trajectory and say, "If that, then what? If it’s true that I’ve been really, really stupid in the past, then what does that mean for the future? How does that change my actions? If it’s true that I’ve been really, really smart in the past, if I flip this all around and say, "No, actually, I’ve been really smart in the past," okay, then what? What does that say for the future? You need to ask yourself, "How does this serve me?" None of them are necessarily true. So if that, then what? And then you can choose one. You can say, "Actually, I’m going to adopt this perspective. It helps me to see that this is how I’m choosing to see my past because this helps me for the future." Just make sure that you know that it’s not the only answer because if you find that you’re holding a story about the past that’s disempowering you, that’s making you feel helpless or stuck, you need to know that it’s just one of many options. So you can just wipe it and try a different story and try a few different ones on and then not just settle for the next one you think of either, but make 10 different stories about your past and see how each one affects you. And maybe it’s story number eight that you never even considered before unless you forced yourself to do this brainstorming exercise. But oh my God, if you look at your past through that lens, whoa, well, that opens up so many possibilities. In fact, it makes me want to jump out of my chair right now and go make this thing happen. And I’m going to apply for that thing I thought I could never do. And I’m going to go speak to that person that I think I’m not worthy to speak to. But actually through this lens, I’m going to make that happen. And suddenly one perspective can change your actions so much. And then there you go, that’s the one that you should be adopting because it works for you.

Andy Vasily

That goes back to the idea of curiosity, and I think being open and curious about more than one way to look at things, more than one possibility. And that opens up our cognitive lenses of possibility and allows us to make the best choice based on the information we have. And this connects good segue towards the end is the last thing that I really resonated with was the chapter, "Here’s How to Live, Learn." And what you say is, "It’s the strong swimmers who drown. Don’t believe what you think, have questions, not answers, doubt everything. The easiest person to fool is yourself." And this goes back to this idea of lifelong learning and the pursuit of excellence requires us to really challenge ourselves and what we’re putting out in the world. And we might think that what we’re putting out in the world is right, the right way to do something. And a recent example I can give you is like, I’m an educational consultant and I feel I’m always trying to understand perspectives and I know how hard teaching is to be an impactful teacher. You have to constantly change your perspective because you’re dealing with so many different learners. But there’s a consultant that was putting out their work as exemplary practice, the right way to do it. And I found myself getting irritated because as a lifelong learner, even though this person wasn’t saying it’s best practice, everything in the posts were implying that it’s best practice. And the posts were only showing exemplary work. And my pushback was like, exemplary work is a small percentage of actual work in a classroom. I would love to see examples of not exemplary work and how your work applies to not exemplary work to meet the low level, the low entry point learners, blah, blah, blah. So I had put some comments up, posed as questions, really like trying to open up some dialogue. And the person sent me a private message and said, I will not answer any of your questions. I’m just letting you know. If you have feedback for me, more or less, if you have feedback for me, please send me a direct message and give me the feedback and direct message. Because if you post it publicly, I’m not going to answer it. And I said, aren’t we in a position to model what it’s like to have a civil disagreement or just model what it’s like to have discussions around best practice and not having the right answers? I think we’re in a perfect position to do that. No, I’m not going to do that. I will not answer any of your questions. You can send me a direct message. So unfollow. It’s just not worth it to me. It saves me a heartache. So anyways, going back to that chapter and learning, you also talk about this idea of dislodging your first impression on purpose because you feel that your first thought is always an obstacle. So share some insight into that when it comes to who you are as a learner and what you value and prioritize and any advice you have for the listeners.

Derek Sivers

Okay, well, first, obviously, yes, challenge even the things that seem right to you. So all of us have at some point in life acted like the other person you’re describing, where we feel like, nope, this is it. This is the way. This is how to cook a steak. This is the only way. This is how to make a website. This is how we do the laundry. We have so many things in our life that we think are just a closed issue, that that’s it. This is the way to do it. And we don’t want to have somebody coming in to challenge every single one of these things. Hey, have you tried folding your laundry backwards? Like, just shut up. I’m just trying to get my laundry done. Can you get out of my way? So we’ve all been in that position of not wanting to hear the critique and the challenge of everything, but it’s really useful when you have a moment that you’re not harried and stressed and overwhelmed to ask yourself, like, what’s the counter example to that? I think I’ve found the right answer. Can I disprove the wrong answer? Or can I give an argument to the wrong answer?

Derek Sivers

So approach to learning. I try to journal a lot in a private journal. I’m glad it’s not public because I’ll just pour out my thoughts into many different perspectives. And once I see that I tell some story about even just this is what I’m going through, this is what I want, this is the past situation, this is the current situation, this is where I want to go in the future, it’s really useful then to start doubting all of those things. Like saying, is that really where I want to go in the future? Have I ever been in a case like that before? Is this really the present situation? How else could I see this? And I do that privately, just fingers flying, just say half an hour of just alone time at the computer, empty text file, fingers flying, questioning my answers, answering my questions, questioning those answers again. And it’s really so many times helped me find another perspective that brings me peace or a new insight. So this to me feels like the real point of learning is not to just take in more information, but to take in that information and then ask yourself, how could this be applied? Where else could I use this? Even if you’ve learned some new fact about AI, to ask yourself, how else could I apply this in my life? I seem to be excited about AI because I think it’s an all-knowing Oracle. Why do I want an all-knowing Oracle? Could a magic eight ball serve that same purpose? Like maybe I’m believing the story that AI is smarter than us, but perhaps is it just my belief in the story that’s giving me peace? And in fact, it makes me happy to think anything’s the answer. And could I come up with my own answers and just decide that I am smarter than the AI and I’m going to come up with the answer? And if that, then what? If I pursue that path, where would that take me? Would that be liberating or would that be painting myself into a corner? So anyway, that’s my approach to learning is to try to apply these things to so many aspects of life and question it all.

Andy Vasily

Do you feel unlocked? Does learning feel like true aha learning? Does it feel like you’ve unlocked something or is it just something you add on? Like, you know, okay, little bits of information you’re just pulling in and absorbing or does it, I guess it would depend on the aha moment, but yeah, can you just describe what it feels like to actually learn for you? What does that feel like?

Derek Sivers

Of course there’s different definitions. Sometimes just taking in more information technically you could say you’re learning, but I think we all know the best moment is that, whoa, blow your mind, spin your head around. Wait a minute. Are you telling me this, that changes everything. That is such a joyful moment. I think it’s the reason I read nonfiction books is in constant pursuit of that moment that blows my mind. We’ve all experienced it from movies that have a twist at the end, you find out in the sixth sense that the guy was dead all along. He was a ghost. You go, whoa, hold on a second. Wait a second. But all the sudden, oh my God, the kid sees ghosts. That’s why, whoa, oh my God. It’s, you know, this is blowing my mind. It’s the same thing when I read books about culture. I’ll just pick a random thing that I said earlier about Yoko Ono and John Lennon saying, no, it’s, you’re not allowed to tell me the truth because that’s your selfish unburdening. Whoa, hold on a second. Telling the truth is selfish unburdening? Whoa, if that, then what? Wow, what an interesting lens to see this through. But again, let’s not think that this is the only right answer. That’s one way of looking at it. And which by the way, the, the picture of the orchestra seating chart at the end of How to Live, the whole point was these are all instruments that you can play for a purpose. The harp is not the one and only best instrument. The clarinet is not the one and only best instrument. You as the composer and conductor use the clarinet sometimes and use the harp sometimes. Maybe you want to have the harp and clarinet playing a melody together. Whoa, how interesting to have these two very different instruments playing the melody in unison. And this is like your life that you can use a present focused hedonistic live only for this very moment and maximize pleasure in this instant. Forget the past, forget the future. All we have is now. And you could combine that with another one like generosity. Whoa, how interesting. Like putting a harp and a clarinet together to combine hedonism and generosity to say there’s only now forget the past, forget the future. I’m going to go live for others and give everything I can to everyone every day in the moment. Whoa, you’ve just painted a new color. You’ve combined yellow and purple into some interesting mix that we hadn’t considered before. You can use these different perspectives to paint yourself whatever life you want.

Andy Vasily

Yeah, that’s beautiful. What a great way to end. And I have one more question, but I just wanted to obviously the listeners can just put your name and they’ll find you. But yeah, can you tell people where they can find you and in particular your books, you know, because I would love them to know where your books are.

Derek Sivers

Well, one place only. I’m not spread out on social media. My own website you will see is deep and has everything. So my website is sive.rs and it’s where I keep all of my thoughts and all of my books and even my notes on other books I’ve read. The last 400 books I’ve read over the last 18 years are all there for you to browse. Every interview I’ve done including this one will be at my website. So yeah, it’s all there including my books. The last five books I’ve written are all on the homepage. So also there is the link to email me and that’s the same way as you just emailed me for the first time a few weeks ago and I’m so glad you did. So anybody listening to this go send me an email, say hello.

Andy Vasily

And you donate the, from what I saw, the books are very reasonably priced and you donate the money to charity.

Derek Sivers

Yep. Yeah, it’s nice that instead of paying $15 to Amazon where I get $2, instead if you buy it directly from me for $15 then all of it goes to charity. So I just pay back my expenses for the making of the books or the translating and the editing and everything else goes to charity.

Andy Vasily

Yeah, awesome. I really recommend that the listeners, I’ll put all the links in there, but the books are fantastic and there’s so much learning there and we’ve just kind of taken just a snapshot little dive into two of the books. But I really encourage them to reach out to you and get your books.

Andy Vasily

And in closing, Denzel Washington once told a commencement speech where he talked about the ghosts of unfulfilled potential and that on our deathbed we’re surrounded by the ghosts of unfulfilled potential and they’re angry and they’re pissed off at us and they’re hurt because they gave us talents and strengths that we never used and they gave us opportunities that we didn’t take action on. And they’re hurt and angry because now they have to go to the grave with us having this unfulfilled potential. So what Denzel says is don’t have any ghosts of unfulfilled potential around you when your time comes. And this connects to some of your writing where you talk about putting it all out there. Like imagine you’re going to die tomorrow. Keep putting great work out there because you never know when the end is here. But project forward hopefully three decades, four decades, five decades, who knows by then maybe we’ll live to 150 but eventually we’ll be at that deathbed and we don’t want to be surrounded by ghosts of unfulfilled potential. Maybe we do, I don’t know but what’s your take on that and what evidence will you have that would indicate that you have no ghosts of unfulfilled potential surrounding you?

Derek Sivers

If you think you’re going to live another 60 years, how does that change your actions? Let’s say the oracle tells you for certain, in fact here’s the exact day you’re going to die, it’s 60 years from now, you’ve got 60 years to go. If that’s true, how will that change your actions today? Or if the oracle tells you actually you’ve only got six weeks left, how will that change your actions today? Choose which story you’re going to tell yourself based on which one helps your actions now. I used to believe this thing, I’m going to live a really long time and hey medical improvements are getting better and by the time I’m old aging will be almost half cured and I’ll be sure to live 100, 120. And that mindset got me not doing much. Whereas if I think I’m in the last third of my life, statistically for somebody born in 1969 in the US, male, something something in the average lifespan is this, okay so 78 then subtract where I am now, okay wow. I’m in the final...

Andy Vasily

23 years left, we have 23 years left man.

Derek Sivers

Right, that works for me. I don’t know if I’m going to die in a month or 60 years but thinking I’m in the final third of my life, that works for me. That is the procrastination elimination! That makes me jump into action, not put anything off. Also the ghosts of potential, it honestly makes me shoo them away because those can be distractions. You know, "Hey Andy, you could be a really good drummer. If you were to start now, start practicing your rudimentary skills, you could be a great drummer in 10 years!" Stop, wait a second, "No Andy you know what, you could be an endurance athlete right now if your maximum potential is this." "Hey Andy, you could be a great writer. You know, you need to start writing every day!" These are all your ghosts of unfulfilled potential. If you try to get to the grave with none of them dead, you’re going to take them all to the grave because you can’t get anything done. You can’t do everything. You can only do something. You have to decide. So I am happy at this age to push aside all of the things that could have been and say nope, running out of time, I need to make this one happen. All those other potentials will just have to go away.

Andy Vasily

Yeah and that aligns with your mastery chapter in How to Live you know and really picking that particular area than doubling down you know and making it your focus. So Derek, I really appreciate your time. It’s been a great conversation and just a glimpse into your work but you are doing really special work and I personally have benefited greatly from it and it has helped me to think differently about the things that I might hold onto a little too tight. So even though I knew your work quite well, preparing for this interview took it to another level and I had your voice in the back of my mind a lot you know when I was preparing with some of the lessons that you share. So for me personally, your work has meant a lot and has impacted me quite a bit and I know it has for other people as well so yeah I thank you for everything that you do. It’s really important work so yeah thanks for coming on the show. Thanks Andy. Okay I’m just going to close it off and then I’ll say bye to you. So everybody thank you very much for listening to this episode with Derek Sivers and I hope you come back to listen to future episodes. Okay yeah thanks so much Derek.