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Derek Sivers

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2023-04-21
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2023-04-21
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  1. It's just a random domain name they got, but it's like it's programmers and Sidmen's talking tech and it's fine. It's like hacker news minus the business. Oh, I hope I didn't send a bunch of traffic their way. Yeah, I looked at the.org and I used to have Sivers.org and I looked at that. I was like, I'm not really an organization, am I? Those four characters aren't really necessary, are they? I was like, I think I could reduce those. And so, yeah, S-I-V-E.rs. All right.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  2. This matters to me more than money. So it's like the reason I do a podcast like this. It's like I'm clearly not selling anything. I don't have a big ask, but I really like it when people email to introduce themselves, especially if it's not coming with a loaded question. Like, what would you tell your younger self? What should I be doing with my life? But when people just introduce themselves, it means the world to me. It's really cool to feel connected with people from around the world. to know that I have friends in India or have friends in Nigeria or friends in Finland. That's my favorite thing is hearing from strangers. So honestly, like my website, which I made myself as a static HTML website speaking of our earlier tangent, if you go to s-e.rs, yeah, just send an email and introduce yourself. That's my... Surprising

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  3. Now I'm in Bangalore and we finally meet. And it was so damn rewarding. And similar thing. It's like going to Helsinki, Finland for the first time. And what do I do? I email, say like, who do I know in Helsinki? And there were a number of people that had emailed over the years to introduce themselves. And soon I'm like sitting naked in a sauna with some dude that emailed me because, you know, he read my book.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  4. Going to say this is crazy, but still to this day, like my currency, the thing that matters to me more than money, the thing, obviously many things do. I still really like meeting people. Like I just recently went to India and went to Chennai and Bangalore for 10 days and I sat down and talked with 50 people in 10 days. I had one to two hour long conversations with 50 people. And a lot of these 50 people are people that I'd been emailing with for years. Like they just contacted me out of the blue because they read my article or they read my book or they heard a podcast. They emailed to introduce themselves. And here it is 10 years later.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  5. It's kind of the only thing I do. May X after we broke up said, Wow, I've known you. I've never seen you get mad. I've never seen you cry. I've never even really seen you get upset. I'm like, yeah, I just don't really. Like I'm a happy dude. Yeah, like this is the only thing, but it's like, it's not a, obviously not an upset cry. It's like, holy shit, this is such a big deal.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  6. It's funny also collecting my thoughts on how to say this, I don't have to explain a bunch. Nobody's asked directly. It's like if you do this right, it passes on for many generations. A kid that's raised really well can like pass that generosity of spirit. And then somebody that's raised ignored might pass on that scarcity of spirit, you know? I'm not doing this for the media. This is not like trying to be a. A captured moment. Holy shit!

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  7. It's so important. The stakes are well yeah shit Well yeah new experience To collect myself for a second, it's the stakes are so high that it's like if you do this right, it passes on. Wow, what should...

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  8. If you guys have ever seen or go see the song Papaute by the Belgian musician Stromai, it's basically this. It was a hit single in France and Belgium. There's a great music video for it of this guy who's basically being a bad dad. And when he and I watched that video together, I always cry

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  9. He means so much to me that it's I'm proud of myself that I didn't cry when I told the story about the cardboard box in London. I almost did.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  10. He's seen all the previous ones. He's seen much worse. He's read the saga comic books. Highly recommended, by the way, saga. Best graphic novel. Anyway, so he's seen it all. So I went in to try to get the tickets while my son and Tim were out on the street. And he said, can you teach me how to like I'm 16?

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  11. Yeah, weirdly. That was off point for New Zealand. New Zealand is a wonderfully casual culture. Formalities are very uncommon here, but that was a weird moment of strictness where they wouldn't let my 11-year-old come in to see John Wick, but we were determined to get him.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  12. I like how my son spent time with you. Wellington, and wanted to ask you questions about Antarctica and instead he had a more pressing question, which is, what is it like to be sixteen?

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  13. I owe him thanks yet again for It was one of my favorite episodes of yours that a conversation with Matt in Antarctica. Oh, yeah.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  14. Take two of these come in the morning. Oh shit, I'm Can you go east from Antarctica? How do they do directions in Antarctica?

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  15. How do I think of that question? I keep getting that question all the time on podcasts. Damn it, this question again. Like, what I would tell my younger self, I think it came up again just two weeks ago.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  16. Funny, the nature that these questions come to us and is usually one question asked, one answer expected. But if you think of the physical metaphor, just imagine that you are somewhere on Earth right now. Say you're sitting somewhere in Argentina and a phone call comes in and says, how do I get there? How do we get to where you are? Depends where you are. Are you in Brazil? Are you in France? Are you in Finland? Where are you? But that would take a back and forth that we don't have. If somebody asks you one question, how do I get where you are? Only honest answer is what depends. It's not a sound bite.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  17. I think that is What advice would you give someone who wants to be where you are? Not where you are, like how to get how do I get where you are?

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  18. Because to me, at that moment, that's what I wanted to tell my younger self. I felt like culture sold us this story that women don't like sex, that it's something men want in women reluctantly give. And so for like most of my life, I was trying to be considerate. And so I was not entirely sexless, but mostly. And it wasn't until my late 40s. That it was like, oh my god, women like sex. Nobody told me this. Oh my god, this changes everything. I had more sex in the last three years than the rest of my life combined because this newfound insight. And so what would I tell my former self? Well, fuck yeah, that's what I would tell my former self. But that's just me. I don't think that's the question

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  19. When people ask the question, what would you tell your younger self? What's the real question there? I unfortunately have taken that question literally too often. And you asked me seven years ago when I said women like sex

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  20. For framing it like that, sometimes I feel guilty speaking candidly about something that's actually going on with me if I know that it doesn't apply to everybody. Whatever I do publicly, I try to make it for them. It's not so much my personal expression as it is me giving back. Like the world's given me a lot. This is what I do to give back. But it's a nice reminder what you just, the way you just framed it, it's kind of like Felix Dennis writing his How to Get Rich book. Dude was worth $600 million or something when he wrote that. He didn't have to write that book, and he wrote about his extreme case. But for me, as a small fry reading it, it was really useful. To read what somebody in an extreme situation did and how he made his choices. You know what I've been meaning to ask you forever? I'm sorry, wait.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  21. And so I spent far too long in my diary thinking of every possible place on Earth I might live and why I could or I spent hours reading about places that I still haven't even visited, but I learned all about them. I even know what it takes to move there. You know, the naturalization law of becoming a citizen there and the steps to becoming a resident there and the pros and cons of living there. And I've read books about it still haven't been there because I did that for many countries. So that's something that was like 10 years ago. I was still maximizing that. And now here we are in New Zealand, where the longest I've ever lived somewhere in my life. Right here. I used to always move around every two years and I've been right here in Wellington 11 years now

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  22. Think 10 years ago I overthought the where to live. A lot. I was feeling very free after I sold my company. It's like, what do you do if you can do anything, but you don't have to do anything? And where do you go when you don't have to be anywhere and you can be anywhere? It's like too much freedom. It's a complete blank slate with no restrictions at all. I wasn't even in a relationship. I was just completely unbound.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  23. Yeah, and so it's, I mean, that's kind of one of those, you know, nobody cares what you're bad at things. It's like, I'm sure there's a bunch of stuff that Josh Waiteskin is not good at, and he just doesn't matter.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  24. He's one of those invisible mentors, not like officially. I loved his book, The Art of Learning. I've listened to his interviews and I really admire him. I have many times wondered, like when I've hit some kind of dilemma or a situation, like how much Josh Wait's doing this.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  25. And kind of like the, I don't know who the hyper effective person is you mentioned earlier, but choosing that they're just a couple things that you care enough about. Like I am glad that Josh Waiteskin is not a satisficer. I am glad that he went all the way down the rabbit hole.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  26. And now that I put that into action, it was because of reading Paradox of Choice. I said, okay, I need to do this. He's right. Dude's smarter than me. I'm going to do this. So yeah, I just internalized it and I did it. And when I catch myself in a moment, see, I think like shortly after reading the paradox of choice, moved to Portland, Oregon. It's a pretty car-focused city. The CD Baby office was out in the far reaches and I needed to get a car. And I had just recently read Paradox of Choice. And I said, I'm going to give myself two hours to choose a car. Maximum. And so, yeah, I... In two hours, I did quick research for 30 minutes, went out to some car lots, looked at a few options, went, this one, good enough. I loved that car. Was it the best possible choice? No, who knows?

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  27. Yeah, so just like I think you can't preach minimalism to somebody who hasn't felt the pain of having too much stuff. Need to feel the pain of having to look after too many things and having a cluttered house, and they go ugh, I need some minimalism. You can't just preach it to them. So I think it's the same thing with maximizing and satisfying. And I think satisfying is a lifestyle for me now or something that's deeply internalized, let's say, because I've felt the pain from trying to maximize decisions and spending hundreds of hours trying to find the best this or best that or, you know, make the best decision. I mean, God, I write in my journal so much, so many pages on something. And in the end, I'm just like, I felt the pain from doing this now. I need to learn how to say good enough.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  28. I just noticed from our walking down the street or walking through a forest and talking, you would pick up on a few words that I said in passing. Two days later you were like, let me ask you some more questions about that. I was like, how the fuck did you remember that?

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  29. But just imagine the joy of God, sometimes even a simple manual labor. What was at the end of the movie The Last Emperor? This guy's been through this big giant arc and at the very end of the movie he's just picking weeds in a garden because he used to be the emperor, but the Chinese revolution would have assigned him to just be a gardener now. And he kind of found his peace with it. We all have different versions of that we could do. For the most part, for the last 12 years, I've just been a full-time dad here in New Zealand. I know there are other impressive things I could have done, but this meant the most to me.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  30. And those people, I just want to like physically restrain them and pick them up and put them into another environment to show them you can do something else, it's a bigger world.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  31. Continue. Those people, I think, absolutely should. Somebody needs to shake them out of their, kick them out of the nest, shake them out of their habits, go to something else. I feel the only celebrity death that upset me was Kurt Cobain All the others seemed to be like, okay, they've made their contribution to culture, and I appreciate them. But I wasn't eagerly awaiting George Harrison's next album. But Kurt Cobain, like fuck. It felt like he had so much more to give, but he was miserable. And something like that, maybe not to that extreme, but let's just use that as the farthest end spectrum on this kind of person that says they're miserable doing this thing, but they feel like it's all they can do

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  32. So, the third category of people that Don't know what else they can do, that's the category that by my values, I want to like physically pick them up and put them into a different scenario. I think it's just objectively you need to change now. You need to shake it up in order to live a full life Need to see the world from different perspectives. You've been doing the same thing for too long. That to me, talk about like beliefs and you know. That's a belief of mine, which means it's not true, but I believe that you should

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  33. Maybe it is because I just had that life shift where it's like I did it to a certain point. I didn't get as famous as I thought I could, but I was successful enough. Like, I bought my house in Woodstock with the money I made touring. Know, like by my own definition, I was a pretty successful musician. Then, just at the time that that was getting boring, I accidentally started CD Baby and I just threw all my attention into serving the musicians. So I think that flips something in my head where it's like, I no longer need the attention for me. I don't need any more attention. I don't need any more validation. And now I don't even need any more money. I don't really don't need anything from anybody.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  34. It was more just like, let's see if I can do it. Know just with that spirit of, I think I can do that. I want to try doing that, and it was also feeling that what I was doing musically was valid. Worth hearing. And so a way for people to hear it is too.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  35. Yeah, I didn't want to be that famous, but like, I don't know, Bryanino? A good fame role model where it's not like he'd get hounded walking down the street.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  36. I think a little bit like the things that you talked about being competitive, like your personal tendency to be competitive. Think as a teenager. Like, I want to get famous not like as famous as Prince. Prince was like a musical role model for me. He was my musical.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  37. Formerly. Okay, so we won't let that go But check this out. You and I have thought for hundreds or thousands of hours about the concept of success, what it means to be successful. I'm 53 now. I have spent almost forty years, or let's say like, you know, 35 years thinking about being successful. Just a few weeks ago, in a podcast interview, somebody asked me, What's your definition of success? And I said, To me it's just achieving what you set out to do. That's your personal success for that thing. I think it's very individual. And he said, Nothing to do with what other people think of you? And I went, other people think? I was like, no, what? And he goes, yeah, I think for a lot of people, they would define their success through the eyes of others. I was like, why? Why would anybody? And he said, wait, you seriously have never considered that? I was like, wow.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  38. And so I took his lesson to heart and I said, All right, Felix Dennis said if he could do it all again, he would just retire and write poetry and plant trees and haven't planted any trees yet. It's kind of what I'm doing. So, if what I'm doing seems weird, it's because I took his advice to heart and I've kind of quit the game. So I think here's how we can summarize it, is to say that most people, I think, Go by the inner compass that says, I'm really good at this game so I should keep playing. But I think we should all entertain the idea. We could say I'm really good at this game so I should stop playing.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  39. No, it's great. And I read that at a key time. It was right about the time that we met, like 2008. I was just selling CD Baby and I was suddenly, you know, coming into more money than I could ever spend in a lifetime. And just about that time I read Felix Dennis' book, How to Get Rich. And in it, he had this quote that I got ready for our conversation here. He said, if I had my time again knowing what I know today, I would dedicate myself to making just enough to live comfortably as quickly as I could by the time I was 35, I would then cash out and retire to write poetry and plant trees. So I read that at a Fork in the road moment for me where I just sold Seedie Baby had a ton of money. It's like, what to do now? And I read this book from this filthy rich old man being entirely honest and I thought I should just learn from his experience.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  40. Okay, that's what I thought you were thinking. That is one specific thing, but that's so wonderful that he admitted that.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  41. Really admirable about the personal challenge of making yourself do something else that most of us stay in. Game for too long I really admired that Jacinda Ardern did that when politicians are known for trying to hold on to power as long as they can, right, until they're forcibly removed. Kicking and screaming. I really admire that she did that. I was super, super influenced by Felix Dennis's book called How to Get Rich

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  42. And he retired Gautier. He stepped away. Jacinda Ardern, the most recent Prime Minister of New Zealand, after six years, felt that she had had enough, and she quit instead of going through the process of running for re election. She quit kind of midterm and she said, that's enough. I'm feeling full, I'm feeling spent. Serena Williams, I think, you know, quit instead of going longer than she should have. She quit after 27 years and like that was enough. She hit her point that was enough. Cameron Diaz. I suddenly, after watching There's something about Mary. My kid, I said, I wonder whatever happened to her. And I looked up and saw that she was the fifth highest grossing actress in America, the highest paid Hollywood actress over 40 She'd had enough, and so she just quit to do other things.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  43. And so, yeah, it's continuing a behavior, even though it's not rewarding you anymore. So, to me, that's what making money is. It's a game that I've decided to stop playing because I got enough. But this could apply to anything. Somebody who wanted to be a successful musician. Oh, there's a great Gautier. I think that's how they pronounce it. You didn't have to cut me out. Now you're just somebody that I used to know. One hit wonder. From Australia, that was his stage name, and he did a beautiful thing as he has retired that stage name. He's like, there, did it. I had a massive number one hit. I don't want to keep singing that song for the rest of my life. There is no more Gautier. So now he's just back to his legal name, and he's the drummer and singer in a band called The Basics.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  44. Say actually, if you are looking for a new game, it is a great game. Stardew Valley is wonderful. But it's so wonderful that my ex and I got really into it. She played it for something like 400 hours or something like that. The little clock shows you how long you've played. And at a certain point, she had done everything. She made every dish, planted every crop, caught every fish. Done every favor for every village or whatever, she was done, but yet there was this yearning to keep playing because she was so good at it. And I think that the temptation to keep playing, even though the rewards are done, isn't that the definition of addiction?

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  45. Yeah, I mean, it's so good I mean, okay, let's say if you want to play a great game that is also non-greedy, I found it because it was recommended on a list of no bullshit games that don't ask you for more money once you're in. You just pay your $9 or something like that up front, and then you've got the game forever. That's cool.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  46. So my ex grew up on a farm in Stardew Valley is one of those little farming games where you tend to your crops and then you get animals and

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  47. In fairness. I try to explain It's just because For 10 years, or 15 years, I was playing a certain game. I was trying to be successful. I wanted to be famous. I wanted to be a successful musician. I wanted to be rich in that way. And I did it. And in my mind, by my own standards, I won the game. And When you win the game, say you're playing settlers of Katan or Monopoly or poker, whatever with friends. When you win the game, what do you usually do is you stop playing. You say okay, let's go do something else. I won the game. Even with, say, addictive video games. So have you ever played Stardew Valley?

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  48. No, that's what it was. So it's... It's something that might seem strange about me, that sometimes people say that I seem weird because of the choices I make in life.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  49. Greater good thing I think about Making it interesting conversation for you, but then there's like how many people that listen, so it's like I try to.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT

  50. Yeah, and I didn't want to bother you with things. So I'm just like, I was tempted, you know, I've got your phone number. I could have just texted you. And I'm like, no, hold on. And I'll just do it first. Never mind.

    2023-04-21 · The Tim Ferriss Show · #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” · IDENTIFIED FROM THE TRANSCRIPT