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Tim FerrissTim Ferriss

Derek Sivers — Finding Paths Less Traveled, Taking Giant Leaps, and Picking the Right “Game of Life”

Brought to you by Wealthfront high-yield savings account https://wealthfront.com/tim and Shopify global commerce platform providing tools to start, grow, market, and manage a retail business https://shopify.com/tim Resources from this episode: https://tim.blog/2023/04/21/derek-sivers/ Derek Sivers is an author of philosophy and entrepreneurship, known for his surprising, quotable insights and pithy, succinct writing style. He is a former musician, programmer, TED speaker, and circus clown, who sold his first company, CDBaby for $22 million and gave all the money to charity. Derek’s books (How to Live, Hell Yeah or No, Your Music and People, Anything You Want) and newest projects are at his website: sive.rs. His upcoming book is Useful Not True. Please enjoy! 00:00 Start 00:58 The Derek Sivers School of Enough. 5:33 Scuba diving in Iceland. 10:24 Categories we apply to ourselves and others. 17:15 Derek’s people compass. 22:59 How to secure your tech independence. 59:39 The un-optimized life. 1:11:21 The meaning of Derek’s upcoming book, Useful Not True. 1:28:10 The problem with moral relativism and other -isms. 1:47:21 Giant leaps. 1:56:55 Finding and asking mentors for help. 2:05:20 Games. 2:09:36 The wisdom of quitting when you’re ahead. 2:14:38 Why would Derek — never in need of external validation — seek fame? 2:18:24 What makes Derek so darned interesting? 2:21:00 Has Derek always been a satisficer? 2:30:06 Living on the edge case. 2:34:12 The real question behind “What would you tell your younger self?” 2:39:30 Giving directions in Antarctica. 2:40:31 How do you teach an 11-year-old to act like a 16-year-old? 2:45:04 Parting thoughts. P.S. To follow the exact step-by-step “Tech Independence” instructions from Derek, please visit sive.rs/ti. Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 900 million downloads and been selected for “Best of Apple Podcasts” three years running. Sign up for "5-Bullet Friday" (Tim's free weekly email newsletter): https://go.tim.blog/5-bullet-friday-yt/ Follow the Tim Ferriss Podcast: https://tim.blog/podcast/ Visit the Tim Ferriss Blog: https://tim.blog/ Follow Tim Ferriss on Twitter: https://twitter.com/tferriss/ Follow Tim Ferriss on Instagram: https://www.instagram.com/timferriss/ Like Tim Ferriss on Facebook: https://www.facebook.com/TimFerriss/

Tim FerrisshostDerek Siversguest
Apr 21, 20232h 48mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 0:58

    Start

    1. TF

      [upbeat music] Should we kick this party off? What do you think?

    2. DS

      Ready.

    3. TF

      All right, so I thought we would start, first of all, cheers.

    4. DS

      Cheers.

    5. TF

      Yes.

    6. DS

      Thanks to Matt.

    7. TF

      Yes. Matt Mullenweg, thank you for the scotch blend, which we shall enjoy here. So I'll take a sip first.

    8. DS

      Ooh.

    9. TF

      Mm. We have scotch, we have Go Go Gadget black tea.

    10. DS

      [laughs]

    11. TF

      What is this called again? [laughs]

    12. DS

      Go Go Goa.

    13. TF

      Go Go Goa. [laughs]

    14. DS

      Yeah, Go Go Goa.

    15. TF

      It's so good to us. Yeah.

    16. DS

      Go. So we have Go Go Goa.

    17. TF

      Like Goa, India, you know, the region.

    18. DS

      Yes.

    19. TF

      Yeah. [laughs] So this is otherwise known, I do have a backup of Diet Coke in case, this is Podcaster Speedball. [laughs] So I expect this is gonna be a fantastic episode.

  2. 0:58 – 5:33

    The Derek Sivers School of Enough.

    1. TF

      And for those who are not watching or those who may not have video in front of them, we have two different sized scotch glasses. And if you were to walk into Derek's [laughs] kitchen, you would find a wide assortment of glasses, namely one other glass which-

    2. DS

      Yeah, there are only three glasses

    3. TF

      ... which is yet larger.

    4. DS

      [laughs]

    5. TF

      It's like a Russian nesting doll of three separate glasses. And those are the only glasses you have in the house.

    6. DS

      Yeah. And I didn't buy any of them, they were just-

    7. TF

      Please explain more.

    8. DS

      Oh, God. [laughs]

    9. TF

      Because you walk the talk of certain types of minimalism. There are those out there who may not believe some of it, I'm just saying, or may be skeptical. Ha- have a healthy skepticism.

    10. DS

      [laughs]

    11. TF

      I'm telling you guys, he's got three glasses in his kitchen. [laughs]

    12. DS

      And this is my only pair of pants. And yeah, so these three glasses, I don't even think about it because I, I just think about having what's enough.

    13. TF

      Yeah.

    14. DS

      Right? So there's only me and my kid here.

    15. TF

      Mm-hmm.

    16. DS

      And so you come over and you say, "Okay, let's make some scotch." [laughs] And you're like, "Do you have any?" I was like, "No, that, that's all I got."

    17. TF

      [laughs]

    18. DS

      "I just have these glasses. And honestly, I don't even know where they came from."

    19. TF

      But they work.

    20. DS

      They work. And this is enough. And these little bamboo cups I got for my kids so that he wouldn't break them.

    21. TF

      So I have a feeling we will come back to this in a sense because as a foreshadowing for people who are listening, if you have not read The Paradox of Choice, Barry Schwartz, he talks about maximizers and satisficers. So I think we'll probably come back to this in a bunch of different ways. But suffice to say, the embodiment of minimalism. You also have two very nice suits that act as your sort of outside in the world attire.

    22. DS

      Yeah.

    23. TF

      Which makes sense to me.

    24. DS

      And only two. It's, again, it's this idea of enough. It's like I wear junk, basically home pajamas. I think of them as pajamas. The, the, the big baggy T-shirt that somebody handed you at a conference.

    25. TF

      [laughs]

    26. DS

      And you would never wear that outside the house. But yeah, Michael Brown, with an E, in London. When I lived in London right before COVID hit, I thought, "You know, I'm living here by Savile Row in London. I'm about to leave England forever. I'm gonna get a custom-made suit." So I looked at, um, oh, what was his name? Sartorial Talks. It's an interesting YouTube channel about somebody diving deep into like the, the craft of fine-

    27. TF

      Tailoring. Yeah

    28. DS

      ... yeah, tailoring. So he recommended this guy, Michael Brown in London. So yeah, I went to Michael Brown and he said, "What would you like?" I said, "You're the expert. You know, just dress me."

    29. TF

      [laughs]

    30. DS

      So he told me what to wear, and I do. [laughs]

  3. 5:33 – 10:24

    Scuba diving in Iceland.

    1. TF

      So let's, let's start with a story now. And I have not heard this story because you began telling me and I said, "No, I don't want to hear it."

    2. DS

      Yeah.

    3. TF

      [laughs] I said, "Let's save it." Scuba diving. That'll be my-

    4. DS

      Scuba diving?

    5. TF

      Scuba diving. That'll be my cue.

    6. DS

      And what it taught me about empathy and identity.

    7. TF

      Amazing. I'll listen to the TED Talk. [laughs]

    8. DS

      [laughs] Oh, God. All right, here we go.

    9. TF

      I'm sold. [laughs]

    10. DS

      So I was in Iceland and I never had any intention to go scuba diving, but I was at that place in Thingvellir Park, if you've ever been there, where the two continental plates meet, the American continental plate meets the Eurasian continental plate and there's this deep fissure in the ground but it's crystal clear water so you can see all the way down. I'm like, "Ooh, I wanna go in there."

    11. TF

      [laughs]

    12. DS

      It just looks like avian spring water, you know, poured over rocks with nothing clouding the water.

    13. TF

      Right.

    14. DS

      So I was in Iceland for a month, so I went to take scuba diving lessons. And the instructor was great. So it's dive.is and at the time it was just him in his basement, and it was me and one other guy learning scuba diving. So we did the practice in the swimming pool, and we did all the theoretical stuff. You learned to scuba?

    15. TF

      Yeah.

    16. DS

      Okay.

    17. TF

      Mm-hmm.

    18. DS

      And so the swimming pool was great, and I love the fact that it's calm, that you don't need to panic about holding your breath. It's just s- slow and meditative. But then the first time we went into the cold ocean, and to be clear, I had to wear one of those giant dry suits. You're like, you're like a spaceman with four-

    19. TF

      Yeah

    20. DS

      ... layers of rubber and, you know, stuff over the rubber. So it's very claustrophobic. And then I get into the water and it gets down to about 20 meters and I'm just like, "Oh God, do I hate this. I hate, I wanna, like, I, I need to go. I need to, I just wanna go back at home. I wanna be on the internet. I wanna be emailing my friend. I wanna talk to my friend. I, I just wanna... You know, I, I just, I gotta get out of here." So I rapped on his tank and I went up to the top.

    21. TF

      You pointed. You pointed to go up.

    22. DS

      Yeah. And I was just like, I tore off my mask and I was just like, I said, "I don't wanna... " No, I said, "I'm just gonna go. You guys go ahead. I'm gonna wait on the side, uh, there. I'll ju- you go ahead. I'll, I'll just wait." And he was so sweet. He was so cool. He looked at me and just stopped for a second and he said, "Hold on a second." He said, "It's a really nice day today." He said, "Look around. Look at those mountains." And then he goes, "See? It's a nice day today." He said, "Yeah, look, look at what a, look at, at what a beautiful area we're in right now. If you were to leave now," he said, "I know you're flying back in seven days. If you were to leave now, you wouldn't be able to complete the training and you wouldn't get your certification. I know you don't want that." He said, "Just relax for a second. It's all right." And so I just relaxed for a second. You know, you inflate your BCD so you're just buoyant and you float.

    23. TF

      Yeah.

    24. DS

      And I went, [sighs] "All right. Yeah. What was I scared of?" So I went, "Okay, I'm ready." And so we go back down and I completed it and it was great. It was no problem. And I love being underwater. It's wonderful. So that was the completion of my training. The next day was my first official dive. So we're there with a dozen other people that have flown to Iceland from around the world, including this couple from Germany that were bragging about how many dives they've done. "We've done over 100 dives."

    25. TF

      [laughs]

    26. DS

      And so they were acting like know-it-alls, but then they're like, "Oh, dry suit. We've never done dry suit before."

    27. TF

      [laughs]

    28. DS

      And so they're getting into dry suit and yeah, it's-

    29. TF

      Ruh-roh.

    30. DS

      [grunts] It's, it's tough, you know?

  4. 10:24 – 17:15

    Categories we apply to ourselves and others.

    1. TF

      babe. I'm out of here.

    2. DS

      I've accidentally missed one step-

    3. TF

      Mm

    4. DS

      ... in the storytelling of this that I should have included, is the night in between those two days, I went home that night thinking, "What the fuck? I think I just had a panic attack." Like, I'm not one of those people.

    5. TF

      [laughs]

    6. DS

      Like, I have no respect for people who have panic attacks. Because usually panic attacks to me, I think of, like, people who are just like, "Oh no," like, "my cake is late. I'm gonna die." And they freak out over shallow little things.

    7. TF

      Yeah.

    8. DS

      And it seems to me like they have no perspective on life. So then I have no respect for that kind of silly panic, right? But I had just panicked, and it was involuntary. And so, like, that night I had this moment of just like, "Wow, what, what does that mean? That am I a panic attack person now? Have I changed categories from a not panic attack person to a panic attack person?" I just kind of fell asleep with no, you know, answers to that. So then, yeah, then the next day had this thing happen with the German couple and I feel like that experience taught me two kinds of empathy. That we categorize people.

    9. TF

      Mm-hmm.

    10. DS

      Like I just said.

    11. TF

      Right.

    12. DS

      The type of person who has a panic attack. And we think of a category of person that's, say, like depressed, fat, homeless, divorced, bankrupt, and you think, "I would never be those things. I'm not that kind of person." But I thought, "Wow, like, a lot of these things are involuntary." It's not like somebody chooses to be depressed.

    13. TF

      Mm-hmm.

    14. DS

      And I realized I had been unfairly categorizing people the same way I had unfairly categorized panic attack people, 'cause now I am one, right?

    15. TF

      [laughs] Yeah.

    16. DS

      I've had that. Addiction, right? Like somebody who said they would never be an addict, then they find themselves addicted to something that seemed harmless at first, and they have to admit, "Oh my God, I'm an addict." But then I realized that Someday these categories might be me or anybody else if you're, you know, categorizing people. This might be you. But then the thing that happened on the second day where there's another category that we don't think we could be, which is like hero, rescuer-

    17. TF

      Hmm

    18. DS

      ... leader-

    19. TF

      Right

    20. DS

      ... athlete. [laughs]

    21. TF

      Things with a positive connotation.

    22. DS

      Millionaire.

    23. TF

      Right.

    24. DS

      Some people in the past few years have become millionaires, which is something that they held in a different category and thought, "I'd never be that," and suddenly they're, "You have to admit, you know, I'm a multimillionaire now."

    25. TF

      Yeah.

    26. DS

      It's a category. So I've realized that we can... Even those categories can be involuntary.

    27. TF

      Mm-hmm.

    28. DS

      That you can suddenly be a rescuer even if you never intended to be one-

    29. TF

      Mm-hmm

    30. DS

      ... just through the power of imitation. So yeah, you can deliberately step into these roles-

  5. 17:15 – 22:59

    Derek’s people compass.

    1. DS

      to keep calling yourself that.

    2. TF

      So I may be skipping ahead because I do like mixing tangents.

    3. DS

      Great.

    4. TF

      But that's the nature of conversation, especially when you have Go Go Gadget tea and scotch involved. [laughs]

    5. DS

      [laughs]

    6. TF

      So we were talking about this the other night at dinner. We use language. We're creatures of language. I mean, part of the reason that we've become such a dominant pest on the planet [laughs] is our ability to use concepts and abstraction.

    7. DS

      Hmm.

    8. TF

      Right? And you'd mentioned at one point thinking of yourself after entrepreneur as a writer. How did you make that switch?

    9. DS

      Looking to your heroes.

    10. TF

      Mm-hmm.

    11. DS

      I call it my people compass. That, like, if you're not sure which way to go, you can ask yourself, "Well, who do I admire? Who do I like?"

    12. TF

      Mm-hmm.

    13. DS

      So for me, this was like, as I was not sure what direction I wanted to go, like I, I am an entrepreneur and I'm a programmer and I'm an author. I actually thought about it in that order. Maybe programmer first, entrepreneur. And then writing seemed to be something I was doing as just, like, a waste product. [laughs]

    14. TF

      [laughs] A metabolite of your other-

    15. DS

      Right

    16. TF

      ... focus. [laughs]

    17. DS

      It's like, it was like, it was like, and as I'm doing my thing, if I learn some lessons, there.

    18. TF

      Right.

    19. DS

      I just put them into writing.

    20. TF

      Yeah.

    21. DS

      But then I noticed that all of my heroes were authors.

    22. TF

      Mm.

    23. DS

      These were the people I looked up to the most, and that helped me realize my values. Like, it helped reveal my values. So ultimately, like, we want to be our ideal selves, right?

    24. TF

      Mm-hmm.

    25. DS

      And I think that your heroes are your idealized self, right? It's kinda, that's why we idolize certain people is we want-

    26. TF

      Mm

    27. DS

      ... to be like them. So that kinda reveals what your values are. So in that moment I went, "Oh my God, that's right. In my heart I'm actually more of an author." And programming is fun. I love programming. I love what it empowers, and I think we're gonna talk about that later. And I'm not an entrepreneur anymore. So in that moment I was like, "That's it. I'm really an author now, aren't I? Wow, that feels weird to me. I never thought of myself as an author." So the reason I call it a people compass is it's related to when you're not sure what business to start.

    28. TF

      Mm-hmm.

    29. DS

      Like, a lot of people are, you know, they're looking at the many different options right now. The way I think about it is asking yourself, "What kind of people do I like being around?"

    30. TF

      Mm-hmm.

  6. 22:59 – 59:39

    How to secure your tech independence.

    1. TF

      Okay. So, so many directions we can go here. I think you alluded to it, so why not hop to it? Programming, the empowerment that can provide. Let's talk about escaping the cloud. [laughs]

    2. DS

      All right.

    3. TF

      Or broadly speaking, tech independence.

    4. DS

      Yeah.

    5. TF

      And to set the stage for folks, we were walking down the street here in Wellington, beautiful Wellington, New Ze-

    6. DS

      Lovely Central Wellington

    7. TF

      ... New Zealand. Well, yeah, the central area is a l- a little bit like Haight Ashbury in some respects, but for the people that get the reference. But all in all, beautiful city. I mean, lots of hiking trails. Shockingly similar to Northern California.

    8. DS

      Yeah.

    9. TF

      I mean, I felt like I was flying into SFO. You have Monterey pine here. You have eucalyptus, which we both borrowed from Australia. You have nasturtiums. A lot of the vegetation here is similar. It's really nostalgic and kind of eerie in a way to be here, because I feel like I'm back in Northern California.

    10. DS

      Yeah.

    11. TF

      It's like being in a time machine. In any case, we were walking around, not in the, on the nature side of things, but downtown, and I said, "You know, I'd love to ask you about cybersecurity." And I said, "Let's say," and I'm not gonna use anyone's name, but somebody who's very technical and hyper-paranoid. I was like, "Let's say they're a 10. Let's say your mom is a one." Not to make assumptions about your mom, but I will.

    12. DS

      [laughs]

    13. TF

      Where do you fall on the cybersecurity spectrum? And that opened up a ve- I think fun discussion. We chatted. You also then wrote in your diary about it the next morning.

    14. DS

      Yeah, 'cause I'm slow like that. You'll ask me something like that, and in the moment as we're walking down Courtney Place, I'll give some half-ass answer. And then later that night I'm like, "Ooh, I got a better answer now."

    15. TF

      I mean, I'll push back a little bit. Yeah, slow is relative. I mean, I think that you were very coherent, and you thought about it before you launched off into some type of, of monologue, which you didn't. It was a conversation, but you then refined it the next morning.

    16. DS

      Yeah.

    17. TF

      So let's talk about this because you gave a couple of, I wouldn't say recommendations. You, you described a few things you do personally that I found very interesting.

    18. DS

      Mm-hmm.

    19. TF

      One of which was you don't use the cloud.

    20. DS

      Yeah.

    21. TF

      Which I think will get a lot of people's attention because, in part, I think there are many people who feel, myself included, that there's something uncomfortable about it. But I assume, since I'm non-technical, there really just is not an alternative, right? But there is part of me that's very privacy sensitive-

    22. DS

      Mm-hmm

    23. TF

      ... and is fundamentally uncomfortable with having all this stuff, all this miscellanea, all these impulsive, ridiculous group chats and whatever backed up somewhere else-

    24. DS

      Mm-hmm

    25. TF

      ... for a lot of reasons.

    26. DS

      Your phone book, your calendar.

    27. TF

      Yeah, all of that.

    28. DS

      All these things, yeah.

    29. TF

      All of that. There's something deeply uncomfortable about it, and yet I use the off-the-shelf tools because everyone else does, and I just assume there are no alternatives-

    30. DS

      Yeah

  7. 59:39 – 1:11:21

    The un-optimized life.

    1. TF

      You know, there's so many options here for where to go next. I think one I'd actually like to talk about is the un-optimized life, if you'd be open to going there next. What do you think?

    2. DS

      Yeah.

    3. TF

      All right, let's do it.

    4. DS

      London.

    5. TF

      London?

    6. DS

      2019.

    7. TF

      [laughs] Ooh, this is gonna be good.

    8. DS

      I took my boy-

    9. TF

      Tuck in, kids

    10. DS

      ... on the train from Oxford to London, and it was one of those days that looked like it might rain, it might not. So we made a plan on the train. I said, "Okay, if it's raining, we're gonna go to the museum, and if it's not raining, we're going to the zoo." And he said, "Okay." So we got to Marylebone Station in Central London. We walked out, and he said, "You know what, Dad? I don't wanna go to the zoo or the museum." I said, "What do you wanna do?" He said, "Let's just walk around." "You sure?" "Yeah." "Okay." We just walked around. So at every intersection, he said, "Let's go this way." I said, "Okay." And so he just led the way through London that day. We walked around for eight hours. So at one point, he was jumping around park benches and met these kids from Croatia, where they got into a little tickling match.

    11. TF

      [laughs]

    12. DS

      At another time, in, like, a little alleyway, he saw this huge cardboard box. It was, like, almost as big as he is, and he got into this cardboard box and wore it like a turtle shell. So he walked around London in a cardboard box for, like, an hour, and everybody would do double takes looking at him, and he just felt so cool in the cardboard box. And then at some point, we found ourselves right in front of the West End musical Wicked

    13. TF

      Mm

    14. DS

      And the show was about to begin in 10 minutes. And I said, "Do you have any tickets? What are, what are the best tickets you have?" And they had eighth row center tickets. They had two left. So we're like, "Yeah, let's do it. Let's go see Wicked." So he left his cardboard box there. We went in and saw Wicked, and he, at one point he whispered to me, he said, "Dad, I like the girl next to me." And I said, "Okay." And later I look over and he's holding her hand.

    15. TF

      [laughs]

    16. DS

      He held her hand. They, they held hands. And so show was over, we go home, and I tuck him into bed that night and I said, "Did you have a good day?" And he said, "I had a great day." And I said, "All right. So what was your favorite thing today?" And he thinks for a bit and then he said, "The cardboard box."

    17. TF

      [laughs]

    18. DS

      And I was just like, I marveled at that. I was just thinking later, like, "If I would've planned and said, 'No, we're going to the museum. Come on, it's a g- it's an important museum for you to know,' then he wouldn't have had this un-optimized experience and f- stumbled into the cardboard box."

    19. TF

      Mm-hmm.

    20. DS

      And so of course, you know, I think about life and I think about, like, that day as a metaphor for how we tend to make plans. Because plans seem to be the th- the tool we use to make the most of our time.

    21. TF

      Mm-hmm.

    22. DS

      But that doesn't always make sense, does it? Because, like, as you go through life, you keep getting new information moment to moment that helps you make the, the best decision for that moment, not what you thought would be the best decision earlier-

    23. TF

      Mm-hmm

    24. DS

      ... when you made the plan, which was a prediction. So I think about, like, for example, this stupid house I'm in right now. [laughs] So this is my stupid house, everybody. I don't like this house.

    25. TF

      [laughs]

    26. DS

      But here I am.

    27. TF

      I would never guess based on your assortment of-

    28. DS

      [laughs]

    29. TF

      ... matching plateware.

    30. DS

      Fine. [laughs] Yeah. Right? How much energy I've clearly put into this house-

  8. 1:11:21 – 1:28:10

    The meaning of Derek’s upcoming book, Useful Not True.

    1. TF

      All right, I'm gonna combine this, maybe another Sivers-ism. It's not really a Sivers-ism, but in terms of how Professor Sivers operates in the world, useful, not true. We've been talking a, a bit about this. I wanted to save a lot of it for this conversation with the mics.

    2. DS

      [laughs]

    3. TF

      Where should we start with this?

    4. DS

      All right. So again, I'm addressing the audience for a second.

    5. TF

      [laughs]

    6. DS

      So, you know, I figure I'm coming on the podcast. This isn't just one of our random conversations.

    7. TF

      Yeah.

    8. DS

      This is for the audience. There's a reason we're hitting record.

    9. TF

      Mm-hmm.

    10. DS

      It's for them.

    11. TF

      Yep.

    12. DS

      We can talk freely without hitting record.

    13. TF

      Mm-hmm.

    14. DS

      So I had to think, what's the most useful thing I could share with your audience that I've learned, like, in the last seven years since we last spoke? The thing that's made the biggest difference in my life, a superpower, a, a big, huge change. So to me, it's been, in short, skepticism. So if you wonder why I'm so happy, why I'm thriving, why I seem to be doing well, to me, it's a lot of my happiness comes from this worldview that is radical doubt. It's skepticism. And so I'm gonna give this the shorthand of calling it useful not true, but the visual for it is that moment at the end of The Matrix movie when Neo realizes, like, those aren't bullets. This is just code.

    15. TF

      Mm-hmm.

    16. DS

      Remember all the bullets come his way?

    17. TF

      Yes.

    18. DS

      And he's like, "Oh, wait, right. Like, none of these rules apply to me."

    19. TF

      Mm-hmm.

    20. DS

      That's deep skepticism. It's empowering. It's liberating. And so what I'm gonna do for a few minutes-

    21. TF

      Mm-hmm

    22. DS

      ... including little stories, is to play Morpheus to help emancipate the listeners.

    23. TF

      [laughs]

    24. DS

      So yes, I call this useful not true, but it-

    25. TF

      Preach. Preach.

    26. DS

      Yeah. There we go.

    27. TF

      [laughs]

    28. DS

      Number one. So, okay, I'm gonna tell you the four bits first, and we'll use that to kind of make sure that we come back to this. So, like, number one, almost nothing is objectively true.

    29. TF

      Mm-hmm.

    30. DS

      Number two, beliefs are placebos. So you gotta believe whatever works for you now. Number three, rules and norms are arbitrary games that can be changed. I'm preaching to the converted-

  9. 1:28:10 – 1:47:21

    The problem with moral relativism and other -isms.

    1. TF

      So there's a lot of this that I agree with. I also wonder how we avoid, maybe we don't, but sinking into a moral relativism where everything is okay-

    2. DS

      Mm-hmm

    3. TF

      ... on some level because nothing is objectively good or bad, therefore general mutilation of, like, 12-year-old girls or whatever it is is totally fine in that culture because the culture is different.

    4. DS

      Right.

    5. TF

      Therefore, I'm not going to object to anything like that-

    6. DS

      Yeah

    7. TF

      ... because I'm not the arbiter of universal truth. Therefore, like, everything is okay in different cultures, different places, different households because everything is relative. How do you think about that?

    8. DS

      I defer to Sam Harris.

    9. TF

      [laughs] Okay.

    10. DS

      Did he ever talk about the moral landscape on your show?

    11. TF

      I don't think we've discussed it-

    12. DS

      Okay

    13. TF

      ... explicitly, so if you wouldn't mind elaborating.

    14. DS

      Probably the best elaboration is to tell people to go search for Sam Harris moral landscape.

    15. TF

      All right.

    16. DS

      The best TED Talk I've ever seen.

    17. TF

      Okay.

    18. DS

      Ever. That is the one. Sam Harris, the moral landscape so beautifully summarizes this idea of judging something morally, objectively-

    19. TF

      Mm-hmm

    20. DS

      ... based on individual well-being and-

    21. TF

      So utilitarianism, like the greatest good for the greatest number of people type stuff.

    22. DS

      Probably. Yeah. He says it better than that.

    23. TF

      Yeah, I don't want to sp-

    24. DS

      Yeah.

    25. TF

      I don't want to speak for Sam.

    26. DS

      But yeah, go find that talk. That's kind of my intro.

    27. TF

      Well, I'm curious. There's, I think, a tension sometimes in my mind between living a self-authored, unorthodox life-

    28. DS

      Mm-hmm

    29. TF

      ... that does not conform to convention for the sake of conforming to convention, while also trying to have some type of consistent moral compass.

    30. DS

      Mm-hmm.

  10. 1:47:21 – 1:56:55

    Giant leaps.

    1. DS

      This is my belief now."

    2. TF

      So for folks listening who may want, who would find it helpful to have a structured way to cross-examine their own beliefs and maybe take an opposing stance and then gather evidence, there's something called The Work by Byron Katie-

    3. DS

      Oh, yeah

    4. TF

      ... which is very much this, and I've found personally very useful.

    5. DS

      Yeah.

    6. TF

      Super, super useful. You teased, you didn't really tease, you, you weren't sure whether to open the door or not. Giant leaps, so with the understanding that what you do is not necessarily what you recommend for all people-

    7. DS

      [laughs] You're going there

    8. TF

      ... what are, what are, what are [laughs] ... Is there an example of a giant leap-

    9. DS

      Well-

    10. TF

      ... that might make for a story?

    11. DS

      ... is there? Um.

    12. TF

      [laughs]

    13. DS

      Yeah. I, um, I renounced my US citizenship in 2011-

    14. TF

      That's a big one

    15. DS

      ... as a way of doing something to... I, I deliberately burned the ships.

    16. TF

      Yeah.

    17. DS

      So I have to explain this metaphor because I've found that most people haven't heard this tale.

    18. TF

      All right.

    19. DS

      But we have all heard of burning the bridges.

    20. TF

      Mm-hmm.

    21. DS

      So you burn the bridge when you destroy a friendship, a connection with somebody, the bridge between you and another person. But to burn the ships is a reference to some, I think, like a Spanish conquistador that had headed off with three ships to South America somewhere, and when he landed, there were thousands of Aztecs waiting to kill them, and they only had a few hundred men. Of course, I'm messing up the details here. But he turned to one of his men and said, "We must not retreat. Burn the ships. The men need to know that we cannot go back. We must go forward."

    22. TF

      Mm-hmm.

    23. DS

      So I wanted to challenge myself to go forward and not go back.

    24. TF

      Mm-hmm.

    25. DS

      And after 40 years in America, I s- felt like, all right, I spent the first 40 years of my life here. I want to spend the next 40 out. But what I found is whenever things got tough, I kept wanting to retreat back to my comfortable California.

    26. TF

      Mm-hmm.

    27. DS

      So I thought, I need to burn the ships. So I did.

    28. TF

      [laughs] Okay. I'm laughing because there's so many rabbit holes we could go down here. I'm gonna, I'm going to use my, my creative license as a host of this podcast to avoid most of them. But are you glad you did that?

    29. DS

      For years, it was my, one of my biggest mistakes in life.

    30. TF

      Made it hard to visit, like, family and friends in the US, right?

  11. 1:56:55 – 2:05:20

    Finding and asking mentors for help.

    1. TF

      Yeah. So let's segue from personal growth to mentors.

    2. DS

      [laughs]

    3. TF

      'Cause many people have had mentors. Many people seek mentors. Many people pine after mentors. And if they could only get ahold of Person X-

    4. DS

      [laughs]

    5. TF

      ... and have a cup of tea or a coffee, pick the brain.

    6. DS

      Pick the brain. [laughs]

    7. TF

      Have, pick the brain. Have a-

    8. DS

      So appealing

    9. TF

      ... have a meal.

    10. DS

      Who would not wanna have their brain picked?

    11. TF

      Yeah. So how would you suggest people ask mentors for help?

    12. DS

      Here's what I do. I have three mentors. So anytime I think, anytime I hit a little dilemma in my life, I write a really good description of my dilemma before I reach out to them, 'cause I don't wanna waste their time, right?

    13. TF

      Right.

    14. DS

      My mentors are VIPs. I don't wanna waste a minute of their time. So, so first I write a really good description of the problem, and then I summarize it. I summarize the context, the problem. I summarize my options, and I summarize my thoughts, because I gotta make this succinct. I don't wanna send somebody a 20-page long email. So I have to make this as succinct as possible.

    15. TF

      What does that in practice look like?

    16. DS

      Oh-

    17. TF

      A half- half page, page?

    18. DS

      Yeah, half page. Like it's like bullet points for everything instead-

    19. TF

      Mm-hmm

    20. DS

      ... of paragraphs, right?

    21. TF

      Yep.

    22. DS

      As succinct as I can. And then before I send it to them, I try to predict what this person would say.

    23. TF

      So each of those three?

    24. DS

      Right, right, what anybody would say to this, but yeah, what this mentor would say, what that mentor would say. I know the way this guy thinks. I've read all his books. I know the way... We've talked a lot. I know what he would say. So then I internalize that, and I address those points that I'm predicting they would say. I'm gonna address those in advance, again, to not waste their time.

    25. TF

      When you say address them, what do you mean by that?

    26. DS

      Kinda like how you asked... I said something five minutes ago, and you asked me a question like, "Can you give me an example of that?" Or, "How do you know this?"

    27. TF

      Yeah, I see. Yeah.

    28. DS

      So it's like, "Okay, I knew you were gonna ask that," so, you know.

    29. TF

      Here's my follow-up.

    30. DS

      Right.

  12. 2:05:20 – 2:09:36

    Games.

    1. TF

      I feel like we should do two things.

    2. DS

      Okay.

    3. TF

      I feel like we should get a, a slight refill-

    4. DS

      Mm-hmm

    5. TF

      ... on the scotch, and then maybe talk about games, the games we play.

    6. DS

      All right.

    7. TF

      Getting good at games, things of this type. So a little bathroom and then scotch break? What do you think?

    8. DS

      Great.

    9. TF

      For people wondering, we just came back from our bathroom/break/scotch refill. This is, I would say, very similar to a lot of our conversations.

    10. DS

      Yeah.

    11. TF

      Like, it's not that different-

    12. DS

      Yeah

    13. TF

      ... from a lot of our conversations, but I do appreciate how much thought you give to deliverables for the audience. Makes a big fucking difference, honestly.

    14. DS

      The greater good thing, I think about making an interesting conversation for you, but then there's, like, how many people that listen, so it's like I try to-

    15. TF

      Yeah. You're good at holding both

    16. DS

      ... looking at you, but I'm thinking of them, no offense. [laughs]

    17. TF

      [laughs] Wow, we could, we could unpack that for a while. [laughs]

    18. DS

      [laughs] All right. You and your euphemisms. All right.

    19. TF

      Dark Mirror, here we come. Uh, cheers, man.

    20. DS

      Cheers.

    21. TF

      So nice to see you.

    22. DS

      Thank you for suggesting... Oh, thanks again, Matt.

    23. TF

      [laughs]

    24. DS

      [laughs] I don't know why we think Matt's there.

    25. TF

      Yeah. [laughs] Matt's got the, Matt, Matt's got the fuzzy hat on-

    26. DS

      Yeah

    27. TF

      ... otherwise known as the boom mic. Uh, ah, it is nice. All right. So we're all playing games, right? And I think it's a matter of knowing which games you're playing outside of some basics. You got shelter, you got food, you know, you cover some of the lower rungs of Maslow's hierarchy of needs. Beyond that, we're all playing different games. So knowing which games you're playing, then choosing the game you wanna play, these are, these are important topics. Why don't I just hand the mic over-

    28. DS

      [laughs]

    29. TF

      ... and let, let you talk about how you think about this kind of thing, playing games. Maybe not the proper tee up, but I'm gonna go with it.

    30. DS

      No, that's what it is.

  13. 2:09:36 – 2:14:38

    The wisdom of quitting when you’re ahead.

    1. DS

      And the temptation to keep playing even though the rewards are done, isn't that the definition of addiction?

    2. TF

      Mm-hmm.

    3. DS

      And so it, yeah, it's continuing a behavior even though it's not rewarding you anymore.

    4. TF

      Hmm.

    5. DS

      So to me, that's what making money is.

    6. TF

      Mm-hmm.

    7. DS

      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, Gotye.

    8. TF

      Gotye.

    9. DS

      I, I think that's how you pronounce it. You didn't have to cut me out, you know.

    10. TF

      Oh, yeah.

    11. DS

      Now you're just somebody that I used to know.

    12. TF

      Uh.

    13. DS

      That guy, one hit wonder, Gotye from Australia, that was his stage name.

    14. TF

      Uh-huh.

    15. DS

      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 wanna keep singing that song for the rest of my life."

    16. TF

      [laughs]

    17. DS

      There is no more Gotye. So now he's just back to his legal name, and he's the drummer and singer in a band called The Basics, and he retired Gotye. He stepped away.

    18. TF

      Mm-hmm.

    19. DS

      Jacinda Ardern, the most recent prime minister of New Zealand-

    20. TF

      Mm-hmm

    21. DS

      ... 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 just said, "That's enough. I'm feeling full. I'm feeling spent." Serena Williams, I think-

    22. TF

      Mm-hmm

    23. DS

      ... you know, quit instead of going longer than she should've. She quit after, I think, 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-

    24. TF

      Mm-hmm

    25. DS

      ... with my kid, said, "I wonder what ever happened to her."

    26. TF

      Mm-hmm.

    27. DS

      And I looked up and saw that she was the fifth highest grossing actress in America, the highest paid Hollywood actress over 40, and then she'd had enough. And so she just quit to do other things.

    28. TF

      I should interview her.

    29. DS

      Yeah. Yeah.

    30. TF

      I love those stories. I mean, she would probably not say yes, but I mean, those stories are fascinating to me.

  14. 2:14:38 – 2:18:24

    Why would Derek — never in need of external validation — seek fame?

    1. TF

      I'm excited to dig into this because there's so many facets that I want to hear your thoughts on. So first, I wanna pick up on something that I did not know, although I guess looking at your history makes some strange sense. But wanting to be famous, you mentioned. You strike me as someone, and I mean this in a very neutral way, and this is also why I asked you the other day at lunch, I was like, "What makes you emotional?"

    2. DS

      Hmm.

    3. TF

      You strike me as a very thoughtful, but in some ways unemotional person.

    4. DS

      Wow.

    5. TF

      Not in a bad way.

    6. DS

      Okay.

    7. TF

      But, like, you're not... You don't have volatile emotions.

    8. DS

      No.

    9. TF

      You don't have strong displays of emotion. And that could be a misread. I admire that about you, by the way.

    10. DS

      Thanks.

    11. TF

      Just the general, at least from the outside, maybe it's like the duck on the pond, right? Calm on the, on the top and, like, kicking like hell underneath. I don't know. But you have a thoughtful, almost serene contentedness almost all the time that I interact with you. That is my perception.

    12. DS

      That's true.

    13. TF

      And that's remarkable, right? And you seem to have a very, very, very low need for external validation. That's my perception.

    14. DS

      Yes, that's true.

    15. TF

      So that makes it odd, or for me to hear you say, "I want to be famous," because I'm like, "What do you get out of fame?"

    16. DS

      Um, well, then but let's-

    17. TF

      If that's your constitution? Like, it's, it's-

    18. DS

      Formerly. Okay. So wait, you know what? Something interesting came up. Okay, we won't let that go.

    19. TF

      [laughs]

    20. DS

      But check this out.

    21. TF

      Yeah.

    22. DS

      You and I have thought for hundreds or thousands of hours about the concept of success.

    23. TF

      Yep.

    24. DS

      What it means to be successful. I'm 53 now. I have spent, whatever, almost 40 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, 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?" And I was like, "Wow."

    25. TF

      He's barking up the wrong tree. [laughs]

    26. DS

      Yeah. [laughs]

    27. TF

      He's got the wrong guy. [laughs]

    28. DS

      In 35 years, I had never, ever, ever for a single millisecond considered success as something that would be seen through someone else's eyes. To me, success has always been hyper personal.

    29. TF

      Yeah. So how does fame fit into that?

    30. DS

      I think a little bit like the things that you talked about being competitive, like your personal tendency to be competitive.

  15. 2:18:24 – 2:21:00

    What makes Derek so darned interesting?

    1. DS

      hear it is to-

    2. TF

      Hmm. Someone was asking me recently because I was describing how excited I was to see you. We haven't hung out in so long.

    3. DS

      Yeah.

    4. TF

      It's been so fun to hang out.

    5. DS

      12 years. Yeah.

    6. TF

      God, it's crazy because we also interact virtually. I was describing to someone that I was excited to see you, and they asked what made you interesting, or I don't think they said unusual. It's like, "Oh, so what, what's, what's he like? What's, what's so interesting about him?" And I said, "Well, part of what's interesting is I don't think I've met anyone who has the combination, outside of you, who has the combination of seemingly no need for external validation, yet being a good performer."

    7. DS

      Hmm.

    8. TF

      Right? Like you are-

    9. DS

      Interesting

    10. TF

      ... you're a ringleader in a circus.

    11. DS

      Right. [laughs]

    12. TF

      Musician. You're really good at imitation, voices, et cetera. You enjoy, you seem to enjoy performing.

    13. DS

      Mm-hmm.

    14. TF

      Almost everyone, and I do mean almost everyone, and I'm only saying almost [laughs] because it seems too absolutist to say everyone, but it might be everyone, who I know who is a really good performer, it could be comedy, it could be acting, it could be fill in the blank, had that drive to become excellent doing that because they, they loved or needed or both external validation.

    15. DS

      Hmm.

    16. TF

      I think it's a very uncommon combination, which is why I was asking you about it.

    17. DS

      Hmm. 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

    18. TF

      Mm-hmm

    19. DS

      ... like I bought my house in Woodstock with the money I made touring.

    20. TF

      Mm-hmm.

    21. DS

      You know, like by my own definition, I was a pretty successful musician.

    22. TF

      Mm-hmm.

    23. DS

      And then just at the time that that was getting boring, I accidentally started CD Baby and I just threw all my attention into serving musicians. So I think that flipped something in my head where it's like, I no longer need the attention for me. I no longer, I don't need any more attention, I don't need any more validation. Now I don't even need any more money. I really don't need anything from anybody. But yeah, you're right, I still am socially skilled. I know how to get on stage and talk

    24. TF

      Yeah, you're good at it

    25. DS

      ... yeah

    26. TF

      ... really good at it.

    27. DS

      Thank you.

    28. TF

      You're a combination of elements that I don't usually see together. It's very

  16. 2:21:00 – 2:30:06

    Has Derek always been a satisficer?

    1. TF

      rare.

    2. DS

      Am I blushing?

    3. TF

      You're blushing. [laughs]

    4. DS

      [laughs]

    5. TF

      Could be the scotch. [laughs]

    6. DS

      Yeah.

    7. TF

      All right. So the next question that comes to mind for me is whether you've always been a satisficer, to harken back to-

    8. DS

      Mm

    9. TF

      ... the paradox of choice terminology from Barry Schwartz, or if you've ever been a maximizer. And the reason I ask is because framing games in the way you have, which is once you're, once you're good at a game and you win, it's only natural you'd stop playing that game, is to me, the, the je ne sais quoi, the spirit, the essence of a satisficer. There are people, however, who, let's just say, they want to be a grand master in chess. It's like, "This is my game."

    10. DS

      Right.

    11. TF

      I win, that is a win on the road-

    12. DS

      Ooh

    13. TF

      ... of additional wins and mastery to strive to become the best in the world. Or, here's another option, which is someone who has played a game for so long, let's just say it's finances.

    14. DS

      Mm.

    15. TF

      They finally "win," in quotation marks. They no longer need to work to meet their needs. But they have played one game for so long, they don't know what other game to play, and that paradox of choice and anxiety leads them to continue playing the same game. I know so many examples of people who have won.

    16. DS

      Mm.

    17. TF

      They've won the Oscar. They've made a gajillion dollars, done whatever. They don't have the same love perhaps they once did for that game, but they continue to play it because subconsciously or consciously, they do not know what else to do.

    18. DS

      Right.

    19. TF

      So I know this is a hodgepodge of a question-

    20. DS

      Yeah

    21. TF

      ... but it leads back to, I guess, the, the first, which is, have you always been a satisficer?

    22. DS

      Oh, wow, okay, the sub questions. We are reversing back to the-

    23. TF

      Yeah, this is a whole-

    24. DS

      Okay, so the-

    25. TF

      [laughs] Series of plays wrapped into one

    26. DS

      ... for that third, uh, uh, in fact, I, if you don't mind, I'm gonna, I think I might end up-

    27. TF

      Let's do it in reverse

    28. DS

      ... answering in whatever order they...

    29. TF

      [laughs]

    30. DS

      So the, 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.

  17. 2:30:06 – 2:34:12

    Living on the edge case.

    1. DS

      Well, I think 10 years ago I overthought the where to live-

    2. TF

      Hmm

    3. DS

      ... thing 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.

    4. TF

      It's too much.

    5. DS

      It was a complete blank slate with no restrictions at all. I wasn't even in a relationship. I was just completely unbound. 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.

    6. TF

      [laughs]

    7. DS

      But I learned all about them. [laughs] I even know what it takes to move there and the, 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. That's something that was like 10 years ago. I was still maximizing that.

    8. TF

      Hmm.

    9. DS

      And now here we are in New Zealand, where the longest I've ever lived somewhere in my life is right here. I used to always move around every two years, and I've been right here in Wellington for-

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