#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”

25:07So that kind of 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 going to 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, but I think this is the reason I call it a people compass is it's related to when you're not sure what business to start. A lot of people are, they're looking at the many different options right now.

25:40The way I think about it is asking yourself, what kind of people do I like being around because these are the people you're going to be serving you have to like them you want to love your customers and love serving them because ultimately even if it's the money what you really really want is the emotional fulfillment right yeah totally so you might get lucky by strategically choosing an industry or a market that's on its way up and you might get really lucky and become a billionaire doing something but what if your customers are jerks would you be happy getting rich running an all-night vaping store?

26:14Think of the kind of customers that would come into your all-night vaping store. Are these the people you want to serve? And would you be happy even if you made a million dollars doing that? I think you'd feel pretty mixed about it. I'm a little embarrassed to tell you about my new startup then.

26:31Right. So it's asking yourself, what kind of people do you want to be around? Decentralized blockchain, baby seal clubbing, expeditions. not sure I want to hang out with the people who might go on that tour run by AI we may need a refill on the scotch at the rate we're going pause so um yeah I think that if you set up your business to serve the people that you love being around yeah even if it makes less money you're going to be much happier yeah so that's where I'm at right now like right now I'm not an entrepreneur but I'm starting to get that itch I'm starting to feel like doing something. And if I do, it'll just be to be around the people that I already love.

27:13Okay. So let's poke at that a little bit. Being around the people you love, there are many ways to do that. Why do you think you are maybe leaning towards the entrepreneur vehicle for doing that versus doing other things? Is it what you know? Is there more to it? Because it's asking yourself, what would you do even if it didn't pay? Yeah. I'll just pick one example. And don't hold me to this world if I don't end up doing this idea. Do you know that like seven years ago, I happened to mention that that week we talked, I was enjoying learning the history of hip hop. And for six years, people keep telling me like, so history, I was like, it was just, it was that week.

27:50Come on. So, all right, right now. And now I like olives. So stop lecturing me about my past self. So right now, an idea I'm having is 100-year hosting, legacy personal websites, so that setting up a trust so that your personal website will last on for 100 years or 50 years after you die. And this is the kind of thing I care about so deeply that I would do it even if it didn't pay. I would do it as volunteer work. And I really like people that have personal websites. They're my kind of people that enjoy technology for its own sake, that took, what do you call that? Oomph Go Power? No, no, no. Where somebody takes initiative.

28:30Somebody took the initiative. Is that English? Go ahead. I don't speak Esperanto yet. Somebody took a little, and set up their own website. I like these people. I like people that have personal websites, that aren't doing it for money. They're my kind of people. And so I would be proud to serve them. So that's all I meant by that. 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. Or broadly speaking, tech independence. And to set the stage for folks, we were walking down the street here in Wellington, beautiful Wellington, New Zealand.

29:13Early central Wellington. New Zealand. Well, yeah, the central area is a little bit like Hade Ashbury in some respects, but for the people to get the reference. But all in all, beautiful city, lots of hiking trails, shockingly similar to Northern California. 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. It's like being in a time machine.

29:48In any case, we were walking around, not 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 going to use anyone's name, but somebody who's very technical and hyper paranoid, I was like, let's say there are 10. Let's say your mom is a one. Not to make assumptions about your mom, but I will. Where do you fall on the cybersecurity spectrum? And that opened up a, I think, fun discussion. We chatted. You also then wrote in your diary about it the next morning. Yeah, because I'm slow like that. You'll ask me something like that.

30:26And 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 man. 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 monologue, which you didn't. It was a conversation, but you then refined it the next morning. So let's talk about this because you gave a couple of, I wouldn't say recommendations, you described a few things you do personally that I found very interesting. One of which was, you don't use the cloud, which I think will get a lot of people's attention.

31:09Because 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. But there is part of me that's very privacy sensitive and is fundamentally uncomfortable with having all this stuff, all this miscellanea, all these impulsive, ridiculous group chats and whatever backed up somewhere else for a lot of reasons. Your phone book, your calendar. All of that. 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 that are feasible for a muggle like myself.

31:55Poor Tim. Poor Tim. We're incapable. All right. So Dr. Sivers, please hold court. So audience, I prepared. I took notes because although I love Tim's podcast, I love it most when people come and give us like an intense data dump. Yeah. Know this, know that. So guys, I prepared a couple hours and here you go. So I'm going to unapologetically read from my notes to give you the best bang per buck of your time listening. So tech independence is all about the fact that I think the main sales pitch of the cloud is now don't worry your little head about that. Let us take care of it. We'll keep all of your data.

32:41See, isn't that easier now? there, we've got your data. And it actually reminded me of something I think you said in For Our Body about yoga studios, that no, it's not the best thing for your health, but it's a better profitable pitch for them to sell you a yoga studio instead of deadlift freeway. Yeah, there's a lot of that in fitness overall, for sure. There's an incentive. This is the tech equivalent of that, that I wish that history had gone such a way that we all had our own little private server at home. But instead, the cloud made a better sales pitch saying, no, no, no, give us all your stuff.

33:14We'll take care of it forever. So my idea is if you spend a few hours to learn how to do it yourself, you'll just have tech independence. What that means is self-reliance. It gives you better security, better privacy, better freedom, better flexibility, and total control. And I think it's a great use of your time to spend a few hours learning to do this kind of like somebody learning to drive manual transmission, right? You don't need to do it, but this is a good life skill to have. Especially imagine if we were in a world that had more, it was 50 years ago. Or now in a lot of countries, you still can't drive automatic.

33:48So I don't know if you've heard the same stories I have about how many people have lost their Google accounts. There was a guy I know who's a very savvy tech entrepreneur in Singapore who, because he was so tech savvy, he put all of his kids' photos in the cloud since the day his kid was born. He put everything onto Google Photos. For 10 years, his kid was 10 years old the day that he started a new company and said, I'm going to do the Google Apps for Business. And it asked him a quick question. Would you like to merge this with your existing Gmail account? He said, yes. He merged it. And the next day his wife was like, honey, where are all the photos of our kid?

34:22He went, they're in Google Photos. She said, no, they're not. And he looked up, he's like, oh my God, you mean they're gone? And he emailed customer service and they said, well, no, you chose to merge your accounts and we warned you that they're gone. He said, well, could you please recover them? They said, no, they're gone. This poor guy has no photos of his kid from age zero to 10 because he trusted the clown. I mean, sorry, cloud. He can't trust those clowns. So, um, sorry, that was something. Escape the clowns and the cloud. Escape the clown. Tech snark. Okay. So, um, so every, Oh, you do that.

34:52Do you do that on purpose? I did. Oh, that was good. So yeah. Anytime when somebody talks about the cloud, you know, change it to an N. Clown. Got it. keep all my contacts in the clown. So everything I'm going to describe here takes just a few hours to set up. This isn't a major, major thing. It's not that hard. Listeners of yours are used to being suggested to learn how to do something. And let me also preface this for a quick second. This is not a tangent by saying, I do not experience you. Maybe I'm missing something. Maybe you have spider holes dug in the backyard. I do not experience you to be a hyperparanoid person.

35:31at all. So I just want to mention that because folks might think, oh my God, this guy's got like 20 years worth of oatmeal and gold bars and guns in the basement. And he's this guy, maybe, right? I want to sort of set the proper reference point, which is I don't experience you to be a paranoid person. Not at all.

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37:11If you go to, there's a company I recommend called vulture.com, but it's spelled V-U-L-T-R.com. I could use some branding help, but yeah. So they have something called cloud compute for$5 a month. We're basically that's setting up a private slice. It's just yours, but on a shared computer. Okay. So it's like a virtual private server. Virtual private server. Exactly. I was trying to not get technical. Yeah. So, and a server for people who don't know, I know this is going to be old news for a lot of folks. What is a server? Sounds super complicated and technical. It's just a computer that's always online.

37:44That's it. Publicly accessible, always online. Doesn't even necessarily need to be public. We'll get to that. because I think for setting up your server, there are three options. Either the$5 a month, Vulture.com, Cloud Compute. Number two, search the web for a cheap dedicated server. So now a dedicated server is an actual piece of hardware that is only yours, not shared with anybody else. So if you want more privacy, just spend a little extra money and get a dedicated server, which means, yeah, this physical hardware, you're the only person that has, they have physical access to it, but you have the only root password and it's going to be an encrypted hard drive.

38:17We'll get to that. The third option is go to any used marketplace and find an old used Lenovo ThinkPad, ideally from the T400 series. You can get these for under$200 now, and they're great. And they run any old operating system. And you would just set this up in your closet and keep the master version of your server in your closet. And then the other things would be mirrors of that. But we'll get to that in a second. Okay. So here comes my... Yeah, you have done some work. Good to know. Here's my quick how-to. And I'm going to tell you a few things here. that aren't complete instructions, but they're enough for you to search the web.

38:52So I'll tell you what to do, and you can search the web for exactly how. The first thing you're going to need to do is to use the terminal. So the command line. In the Mac, it's built in. You go into utilities folder. It's called terminal. On Windows, it's called PowerShell. And anybody using Linux, you know what it is. So the operating system I'm going to recommend, the one I use, is called OpenBSD. And we touched on this on the street the other night. The reason I use OpenBSD... Isn't it bondage, sadomasochism? Is that BD? No, no, no, sorry. Berkeley Software Distribution. Oh, there we go. Actually, quick, but I was born in Berkeley, California, and kind of like more people named Dennis go into dentistry because there's an affiliation of names.

39:30Freakonomics pointed that out. I always wonder if my affinity with the BSD operating systems is because I was born in Berkeley. Oh, look at that. I'd be stands for Berkeley, who knows? Anyway, but the reason I got turned on to OpenBSD is because I used to have Linux server as a public server, and it was hacked. And the guy at the data center said, oh, yeah, that's been happening a lot lately. He said, you might want to switch to BSD. It's a lot more secure. So OpenBSD is designed from the ground up by super security freaks. And part of why it's so secure is it's so simple. It's a very, very simple operating system that doesn't do everything under the sun.

40:05It does this that I'm describing, and it does it really well. And it's secure as hell. And it's got, as I understand it, a few lines of code. Yes. Right? Which means, let's just say you're a writer. the more you write the higher the frequency of typos yes and you don't want bugs yes in your code that can be exploited the less code the better so install openbsd and follow the instructions to encrypt one of the disk partitions in there as you're installing it then you're going to use ssh which stands for secure shell to log into it then on your home computer use that terminal to generate a private ssh key you do ssh dash keygen the type you want is ed25519 and then that's going to generate two keys a private key and a public key you upload the public key to your server and then after you do that edit your ssh configuration file to disable password logins so now the only way to log into your server is with your private public key that you just generated right very similar to the crypto public private thing then you go into your pf.conf settings you edit your firewall to only allow port 22 which is the port that ssh uses to connect.

41:12Once you've done that, voila, now your server is super secure. Nobody can get in except you from your computer with the generated private key through SSH is the only way to connect to that server. Can you explain the generated private key? Yeah. It's really just a single command you type on the terminal. If you type SSH-keygen-t ed25519, it will ask you for an optional password and it just creates the private key and the public key. Same name, but one has the .pub at the end. And then you just use whatever tool you want to upload the.pub to your remote server. You put it into the correct place, an authorized keys file, and voila.

41:49Now it will, instead of asking you for your password, it just uses the private key and the public key matching to let you in. Got it. So it's like Marco, Polo, okay. Yeah. We're in, as opposed to entering a password every time. Right. And that's why then you want to change the SSH server configuration files to disable passwords. So even if a billion script kitties were trying to hack your server to guess your password, passwords are just disabled. Okay, this is, keep track where you are. Yeah. Do you think this will become, and I'm non-technical folks, you've probably guessed, but this type of Marco Polo, I'm not going to remember the proper, wait, the private keys and so on, private public keys or whatever the term is, will become more and more prevalent as say quantum computing and so on allows the current level of encryption to be decrypted more and more effectively i'm just i'm just wondering about well this is going to take us off on a major tangent i think it's already i think it's what our phones are already doing behind the scenes with whatsapp encrypted chats or facetime or even just our phones themselves when you type in that code when you first turn on your phone i think our phones are already behind the scenes using public private key yeah so that's the way it should be it's just it is the best solution so far, I think.

43:02Yeah. Side note, if you have a four digit password on your phone, you can change that to eight digit. Simple upgrade in settings. Okay. So next thing you need a domain name. My recommended place to get a domain name is a wonderfully nerdy non-commercial site called bookmyname.com. B-O-K-M-Y-N-A-N-E.com. You don't get 10 % affiliate. Absolutely not. Wait till you see the site. It's like a wonderful old school nerdy. There's no affiliate program there. As a backup, I use netim.com. Both of these are French companies. And there's a third one in Portland, Oregon that I like called porkbun.com. All three of those are really good reputable places to get a domain name.

43:39I recommend them. No affiliate fees at all. I just like them. I use them. Okay. So now you've got a server. And the best thing to start with, like you said, I'm not a guy that's got stockpiles of oatmeal and gold. But once you've got, I don't know why you picked But once you've got your own server, it puts everything else into perspective. So that's really where I'm coming from when I say like, I don't do things in the cloud. It's because when companies come out and say, we can take care of this for you. It's like you've already got your bread and peanut butter and jam in the kitchen. And somebody says, we can make a sandwich for you in your own home.

44:17You think, I don't need your help. For those people who listen to what you just said, they're like, I think I just heard a lot of Klingon. I'm not sure, but I can't parse what any of that means. It sounds overwhelming. Right. What would you say to them? I care about this so much that I'm going to set up a really dead simple thing that's basically just do this. Copy paste this. This is going to work. Look at that. So email me. God damn it. Email you. Write a blog post, Derek Simmers. No, I will. I will. Blog post? What's that? Yeah, you've only written five million blog posts since like 1987. You know what?

44:52I registered the domain name cloudfree with the.ee for Estonia. So cloudfree.com wasn't available? I don't know. I just thought it was clever. Okay. Cloudfree. No, but someday I'm going to write this up into a very simple, you don't need to understand this yet. Just do this. Eventually you'll understand it because that's how I learned. Where are my photos? Oh, Derek Severs says all my photos. Right, right. That's what I really wanted. I want your photos. because that's how we all learned it first, right? It's often like, just do this. You'll understand it later. Yeah. Now just do it. And I think that's a fine way to learn if you trust the source, right?

45:31Trust me. So it's not as hard as it sounds. Okay. It's like someone describing how to hit a baseball. You'd be like, what the fuck? That was like 15 pages of describing and that sounds too hard. It's like, actually, no, you just got to try it a few times. Yeah. Okay. So by the way, you know, it's cute. My kid didn't know what baseball is. They played baseball last week at school and he said, dad, what's this thing with the squares? and set up in a... And he hit a home run on his first try. Oh, wow. It's all downhill from there. Tell him to stop. Yeah, exactly. Everybody was cheering for me, but I didn't know what I was supposed to do.

46:01They told me to run. Okay, so now let's talk about some applications. Okay, so you have a server set up. Here's what you're going to do with it. First, do your contacts and calendar. So I don't like the fact that my phone automatically gives Google all of the contacts and all of my calendars or Apple or whatever. So you can set up, it's called Radical, R-A-D-I-C-A-L-E The website is radical.org It's absolutely free open source R-A-D-I-C-A-L-E Yes .org It's absolutely free open source It sets up what's known as a carddav and a caldav server On your server this will be the new server that you sync your contacts and calendars to So it's dead simple blew my mind You install radical on your server You just basically type one command and it says okay it's running You say okay And then you go into your phone, and instead of telling Apple to manage your calendar and contacts, you just set it to your domain name.

46:58And suddenly it says, okay, synchronized. And now every new contact you add and every calendar entry is synchronized with your server, not apps. And actually, I have gone through this process before, and I can tell people it's quite simple because things have probably changed. But quite a few years ago, if you wanted your, say, Cal on Mac and Google Cal to sync, huge pain in the ass. Right. You had to use a third. So you would have to use a third party. And at least I ended up using Caldav a long time ago. That's since changed. But yeah. So this is not very hard. Deadly. That's why I started with this.

47:34Yeah. It's like the simplest thing to set up. And the most sensitive in a way, or some of the most sensitive. Yeah. Calendar and context. It's so important to know that my contacts aren't being sent to other people. And then you see it backed up yourself. Because there are some people that get locked out of their Gmail account or whatever, and then they're just screwed because all their contacts are in there. But you have them yourself. Okay. So next thing is file storage, where photos, books, ebooks, movies, documents, everything else, they're just files. So the first thing you want to do is to export them out of the apps that are like the walled garden apps, like Kindle and Apple's Photos app, and save it as regular files.

48:10EPUB, JPEG, MP3, MP4, just open standards. So you export it out, you save it there, and now you've just got regular files. You don't need iCloud, you don't need Dropbox, you don't need Google Drive. You've got your own server. So every computer has this dead simple little program built into it called RSYNC. R-S-Y-N-C. Well, Macs have it built in. Windows, I think you might need to install it, or maybe it's there with the new PowerShell. And all it does is synchronize the difference. So if you have 10 ,000 files and you've changed three of them today, and your remote server has 10 ,000 files, but not the new three, you type rsync, and it'll just send the newest three that you've changed.

48:45That's it. So rsync is built in, but you have to manually type rsync in the command and your server name, and it'll go. So that's what I do. But if you're a fan of Dropbox, there's a free replacement for Dropbox called SyncThing, S-Y-N-C-T-H-I-N-G dot net. So it's totally free, open source. I want to give you more scotch, just see what it does to your spelling. This is going to be a lot of spelling. Continue. So it's completely free and open source, and it does that more like automatic style instead of manual synchronization. Well, let me pause. So in your particular case, do you think automatic sync?

49:22Do you like automatic sync? I like having the delay between my servers. Because if you fuck up... Yes. Right. If I accidentally delete a file, even if it's a week later, we'll get to... Actually, you know what? I'll talk about this right now. I have my servers cloned, So that's actually the next step I would recommend anyway. Once you've got this and it's working, for extra security, go back and repeat that first step and set up another server with a different company in a different country. And do it again. Do the SSH port thing. Then you can use R-sync or sync thing, not just to clone between your computer and your server, but that server and the other server.

49:59I have a great idea. Okay. You ready? Yeah. All right. So this next chapter of Dr. Severs, entrepreneur interacting with customers you like who own personal websites. You could create a service that helps people liberate themselves from the cloud for those who own personal websites. I like it. Anyway, just an idea. Because you seem to be philosophically aligned with this. Yeah. I'm passionate about it. It upsets me when people are bound to the cloud or just going to use everything in the company's hand. They're dependent on the service. It's about being dependent. It's about the self-reliance.

50:38People who are dependent on others. Imagine if everybody in their own home was dependent on somebody else to make them food. They didn't know how to make their own food. You'd feel bad for them. Come on, it's not that hard. Here's a knife. Here's some bread. Some peanut butter. See, you could do it. That's how I feel with these things. You only need three glasses. It's easy. I would also say that it's not just about being dependent, it's about being informed. So do you have complete understanding or near complete understanding of how you are storing sensitive information? When's the last time anyone listening to this, or even, I'll speak for myself, yours truly, read the complete terms and service when something pops up and it's 27 pages and you're like, yeah, yeah, yeah, okay, click, accept.

51:26There's a lot of stuff buried in there. There's a reason there are armies of lawyers that work on terms of service and that they're updated constantly. Which is nice to tune into people who care about that stuff deeply, and they can act as a nice natural filter to let you know if somebody's being good or being bad. That's how I found when I recommended bookmyname.com for domains. It was like some super nerd that recommended that. They're like, oh, these guys are old school Unix. You want to go with these guys? They're not these new salesmen trying to raise venture capital for their domain selling.

51:54These are just old school nerds. Doing it for the right reason. That's what I like to hear. These are my people. Okay, so I have three servers now set up in New Zealand, US, and Germany. And I like the delay between them. So I have one that I update every night, sometimes multiple times a day. Manually. Yeah, I just type R sync right before I shut down my computer. It backs up my today's work to my remote server. And then about once a week, I back it up to the second server. Then about once a month, I back it up to the third server. And I really like that delay because there have been times that I've deleted something.

52:26and like a whole week later, I went, oh, crap. Let me ask a dumb question, maybe. Why delete anything? Storage is so cheap. Oh, I know. No, I mean more like deleted lines of code. Oh, I see. Like I thought I was done with that. Right, there was a revision that you want to undo. Yeah, yeah. And sometimes even using Git, but sometimes I'm not, and sometimes it's gone. It's rare, but every now and then. Okay, so website is a no-brainer. The OpenBSD operating system comes with its own web server. So I highly recommend, And no offense to don't install WordPress. We love you, Matt. I adore you, Matt.

53:00But I think everybody should learn how to do it themselves. It's not that hard to do an H1 tag, H2, P tag, UL, UL, L I, Ahref, Image Source. You can learn it in an hour. And voila, now you can make your own HTML website. And anybody, because I get this question about once a week by email, people saying, what do you recommend? I want to make my own site. Well, hold on. Not to push back, but just to stress test a little bit. WordPress is open source. Why not use it? You could, but see, WordPress is, I think, last time I counted, 38 billion lines of code. Yeah. And it does way more than what you need.

53:39So it's kind of like if you said, I need some scissors, and somebody handed you the contents of an entire hardware store. You're like, no, I really just need to cut this. So I think most people, what they want from a website is, I have some thoughts. I want to put them in writing for the world to read. Or I have a couple of photos. That's what most people want. But then, I love WordPress and I used it for years, but it does everything. And I think it intimidates people to the point of paralysis. Yeah. So that's why I say, well, no, no, no, no, hold on. My top recommendation is don't let people tell you that this is complicated.

54:12Because if you look at WordPress or similar services, and by the way, I'm just saying WordPress, I mean, it could be Ghost, it could be any of these things. You get the impression that making a website is hard. Yeah. But it's not. It's just a plain text file that you change it from.txt to.html, and you add in a couple bracket tags. Yeah. And that's it. Yeah. And then you upload it, and it works, and the world can see it. So I just constantly remind people how simple this can be, and I say that even if you just do it this way for the first month, please, like, make your own static HTML web page, even.

54:42I think it's a good exercise, even if you end up later using something else. Exactly. Right? That's what I was getting to. Yeah. So start by doing it that way. And then if you need something that another service offers, you'll recognize that you need it. Yeah, totally. I agree with that. I mean, I edited the first 30 to 40 episodes of my podcast, which is a lot of work. And I'm not a master at it. And there are far better people who work on it now for these later episodes. But I felt good doing it in the beginning. And I was like, all right, if I'm going to delegate anything, to the extent that it's feasible, I'd love to learn how to do each thing.

55:20Otherwise, how am I going to assess anything? Yeah, exactly. Okay, I'll name one last one, and then we're done with this subject. The last thing I'm going to recommend is email. So at very least, get off Gmail and use your own domain name. It's so important to switch your email to your own domain name. You can do that with G Suite, though. I know, but we're talking about the liberation, the independence. It's knowing that you aren't dependent on these guys. So I think it's crucial to extract yourself from the we'll take care of it for you thing. So the three things I'm going to recommend, the three different options in order, the simplest, cutest little one I've found is mailbox.org is in Germany.

56:00And for$1 a month, they do nothing but host your email. And I think maybe your calendars, but you know, we've already talked about that. But mailbox.org, you point your domain name at them. They do your email. They're cute. They're great. They're all privacy focused. If you want the luxury full premium suite of like the best email client on earth, you go to fastmail.com. Fastmail.com is amazing. It's$5 a month. But again, it's they're taking care of it for you. So, you know, the third option is coming. You can host your email yourself on your own server. It's dead easy to receive email. It's a little harder to send email.

56:37You'd have to set up a few config files. But it's not that hard. I do it myself. it's a bit advanced but it's possible and i assume that that would come maybe as you know step eight after you've done other things right that's like if you're starting on the bunny slopes which were the first stages this is like okay now you're getting on some moguls yeah don't try this day one get familiar with the gear first so i would be curious to know how you would reply to people who are listening and they're like mailbox.org in germany fast mail i've never fucking heard of these things no wait wait hold on hold on which is not to say they're not robust and amazing and cute, as you put it.

57:12But they'll say, I have more confidence in Google being around in five years than I do in these companies, which I know nothing about. Ultimately, you can have a certain degree of liberation, but if your infrastructure fails, or these people put up a closed for business sign, and suddenly the hardware upon which things are being stored is game over, I guess I'm wondering how you would address people with those types of concerns. And everything I've recommended here was recommended with that in mind. You should expect that you will outlive most businesses. Yeah. I think that, to me, is the biggest misconception that people have about Facebook or Apple or Google, that it's likely you might outlive Google and Facebook.

57:58Yeah. You know, those of us who were around in the first dot-com boom. Yeah, if history repeats, it's certainly well within the realm of possibility. It was unthinkable in whatever, 1999, that MySpace wouldn't be around. Or maybe, what was that, 2003? So how is mailbox.org better in that sense? Because everything is done with your own domain name. So if mailbox.org ever sends, actually, if they just disappeared one day, you'd go, you just log into your domain name router and just route it to another service. Because everything's being sent to, you know, tim at tim.com. So you have your own domain name.

58:30You can just route it to a different mail server. Same thing with the servers I'm talking about. if one of these services in Germany or New Jersey suddenly went under, no big deal. You've got your clone, your remote clone. Your remote server is a clone of your home thing. Right. So all of this is expecting everybody to fail. Yeah. So the conclusion is, I think this is a great use of your time. It's liberating. It's empowering. And then when somebody tries to sell you a service, you'll know that you can do it yourself if you want to, and you might still choose to have them do it. Question for you.

59:01So if somebody's listening and they say, there's no fucking way I'm going to do all that. However, I'd be interested in dipping my toe in the water and maybe doing the first thing. Just to learn some new technology, gain some confidence. I'm not going to do the whole kit and caboodle because it just sounds overwhelming. But I want to do sort of a science project with some experimentation. What might you recommend to them? I'd say the first baby step is to get your own domain name. Definitely. Definitely. And then move your email off of Gmail and just go to some third party provider of email. Okay.

59:36So you'd start with email. I think so. It's the simplest. It's the only one in there that's not truly setting up your own server. Although I mean, that would, you know, obviously that's the next step is just do that first thing and just have like a couple hours of something that feels uncomfortable and new to you. But voila, you have a server that's running anywhere in the world. And once you have a server, everything else is easier. But yeah, the baby steps is to just get your own domain name and switch your email to that and try to just move everything off of Gmail or just let your old Gmail be your junk account.

1:00:07Okay. Question for you personally, if you had to choose between having your email off of the cloud or calendar and contacts. but you can only choose one. So calendar and contacts come together. Email is another. Which would you choose? I don't know why there's a sense of happiness in having my calendars and contacts be on my own server. Yeah, I lean that way too. And I don't know if I could verbalize why that's the case. Mail sending has become unfortunately difficult because a lot of things get marked as spam unless you do a bunch of more complicated things. That's right. I didn't even think about that.

1:00:45I could see that being a huge problem. So the way I actually have my mail server set up right now, and I don't mean this to... Pretends to be Gmail. Well, can you imagine? What could go wrong? All incoming email comes directly into my server. But for sending, I actually use a service called Mailgun that just handles the sending. So they take care of all the deliverability. Yeah, so it's not an ESP, but it's helping, or maybe it is an ESP, like an email service provider. Oh, it is. Yeah, I guess there are. But for outgoing only. Yeah, I think, I wonder, I think SendGrid to handle some of this as well.

1:01:20Yeah, they're one of the same. So you're really just using their SMPTE servers just to send the outgoing mail, but receiving it privately. So that's my balance right now. SendGrid, those guys have done such a good job, at least last I checked. And I met them when they were just starting. I met them at Techstars a million years ago. And this is an example of where being non-technical hurt me because I just didn't know what I was looking at. The guys were super great, clearly very smart, but I was like, I don't understand that. this. Wait, can we tell people the Shopify? Oh, man. I mean, my most expensive mistake ever?

1:01:58No, no, no. My little thing with Toby. Oh, yeah, yeah, yeah. It's cute. I'll let that one just float by. Sorry, didn't mean to stir up the... Yeah, selling Shopify earlier was my most expensive mistake ever as their first advisor, and they had like 10 employees. So audience, there was this cute moment. So we're going to get to a cute moment. I just want to say that also... God, do I love the Shopify guys. I just thought they're so great. Toby, Harley, the whole gang, just great humans. It's really, it makes me so happy when the good guys and gals do well, right? It just makes me so happy. So, cute story.

1:02:33Sometimes people ask if I can introduce them to you. Yeah. And I'm like, no. I respect your time. Yeah, I appreciate that. By the way, I love your email address. Oh, yeah, yeah, yeah. Which basically says fuck off. Yeah, basically. Yeah, it's essentially fuck off at timferris.com. It's not, yeah, it's not that aggressive, but it makes it clear, like, think twice before sharing my email. Don't you dare give this to anyone. Yeah, yeah. At timferris.com. That is his personal email. Yeah, yeah. A little wordy, but, you know. It's worth it. Give him a hurdle. So, oh, Toby. So, I love the Ruby programming language.

1:03:11And so before there was Ruby on Rails, I learned Ruby in a cabin in Sweden that I was offline for two weeks. So I brought a programming book with me. I was like, well, I'm going to be offline for two weeks. I might as well learn something new. So there was this really unknown little programming language called Ruby. I was like, that sounds fun. So I grabbed this Ruby book, installed Ruby on my laptop, and went off to this cabin in Sweden in the winter for two weeks. I was offline and I learned Ruby for two weeks. I came back going, that was so much fun. I wish I could use this to make websites.

1:03:40And there was news that there was this guy named David in Denmark who was doing something with websites in Ruby. So I emailed him saying, hey, somebody said you're making like a web framework in Ruby. And he emailed back saying, not ready yet. That's all he said. So for those that don't know, that's DHH, David Hennemeyer Hansen. And so then Rails came out about eight months later. And at first look, I was just like, huh, this is a little confusing. I don't really get it. and so I posted to like the Ruby mailing list. Can anybody tell me, I'd be happy to pay somebody for an hour of their time to show me how this works.

1:04:16So some guy named Toby said, I'll show you Rails for$100. I'll spend an hour with you. So I paid Toby$100 to show me Rails for an hour and he showed me over the phone. We never met face to face. It was all just over the phone. I was living in LA and Toby was great. He showed me how Rails works and like got me really into it. I was like, all right, I'm in. And so my old company, CD Baby, we started converting everything over to Rails. I was like, this is great. So a couple years later, I get this email from Toby saying, hey, not sure you remember me, the guy that taught you Rails? He said, could you introduce me to Tim Ferriss?

1:04:51Because I've got this little e-commerce thing I'm doing. I was like, e-commerce thing. No. I was like, sorry, dude. I don't do that. No. So I didn't introduce you guys. So I was thrilled later to find out that Toby's little e-commerce thing is Shopify or became Shopify. Became Shopify. Became the Shopify. And then I was thrilled to find out like another year or two later that you were. We met at RailsConf of all places. Wow. I was a speaker at RailsConf, which I felt I was supremely underqualified. They loved doing that. But I met him in the green room at RailsConf. Oh, sweet. Yeah. That's how you met.

1:05:29I was going to ask you. Yeah, that's how I met. Wild. So yeah, Toby and I have emailed since then about like joking about, yeah, Sorry I didn't introduce you guys. Yeah, Toby's a spectacular human. Big, big fan. It's kind of funny that somebody listening to this thinks that we might be talking about tech and programming the whole time. But no, that was it. We're done. We're not going to talk about Unix command line terminal stuff anymore. Yeah, well, we'll zig and zag. So let's zig a little bit. 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 unoptimized life.

1:06:07If you'd be open to going there next, what do you think? Yeah. All right, let's do it. London. London? 2019. Ooh, this is going to be good. I took my boy 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 going to go to the museum. And if it's not raining, we're going to the zoo. And he said, okay. So we got to Marlebin Station in central London. We walked out and he said, you know, Dad, I don't want to go to the zoo or the museum. I said, what do you want to do? He said, let's just walk around.

1:06:43Sure. 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. 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 felt so cool in the cardboard box.

1:07:19And then at some point we found ourselves right in front of the West End musical Wicked. And the show was about to begin in 10 minutes. And I said, do you have any tickets? What are the best tickets you have? 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 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. He held her hand. They held hands. And so show was over. We go home and I took him into bed that night and I said, did you have a good day?

1:07:55And 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. And I was just like, I marveled at that. I was just thinking later, like, if I would have planned and said, no, we're going to the museum. Come on. It's an important museum for you to know. Then he wouldn't have had this unoptimized experience and stumbled into the cardboard box. 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 tool we use to make the most of our time.

1:08:36But 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 best decision for that moment, not what you thought would be the best decision earlier when you made the plan, which was a prediction. I think about, for example, this stupid house I'm in right now. So this is my stupid house, everybody. I don't like this house, but here I am. I would never guess based on your assortment of matching plateware. How much energy I've clearly put into this house and making it perfect with all of its decor. There's nothing on the walls.

1:09:16No furniture. Yeah. Yeah. Except for some mice. Yeah. Legitimately. Yeah, I have three pet mice. We were going to bring them out. It would be distracting. I thought about getting rid of this house and getting a house that was more suited for me. And I actually put an offer on a place. And it was a really nice place. It was at the end of Clyde Key Wharf, which is out there in the water. And oh, man, it was nice. And so it was like the night before my offer was accepted. And it was the night before I was going to put down the deposit. It was going to be mine. And I fell asleep that night thinking, at first thought, I was thinking, I'm going to be so happy tomorrow.

1:09:53And then I thought, wait, I'm already happy. What, am I going to be more happy tomorrow? No, I'm already happy. It's like, well, then why am I doing this? Why am I spending a bunch of money if I'm already happy? So I yanked it. So I didn't buy it. And here I am in this stupid house because it has no obstacles. Like, it's warm. It's quiet. It's not suited to me perfectly. but that's okay. Like it doesn't get in my way. And then from there, I think how many other things in our life are we okay to just not optimize? Depends where you draw the line, right? Your romantic relationship, your job, your family, but nobody has the perfect family of their wishes.

1:10:33Our location, where you live, our diet, you have to kind of decide what's worth optimizing. That we don't need to optimize everything. It's okay to have some things be good enough. And so I'm so glad you brought up The Paradox of Choice by Barry Schwartz. I really fucking internalized that book. It's a great book. The ending of that, where he says like, okay, I've been describing the problem. So what's a recommendation? And he says, satisficing. There's maximizing and there's satisficing. I had no idea you're going to bring this up. This is great. Yeah. Yeah. That maximizers have been found to feel worse about the decisions they make.

1:11:12They look into every possible option. They try to make the best possible choice, but studies show that they feel worse about the choice they make. Whereas satisficers may not make the absolute best possible choice, but they feel much better about the choices they make. Yeah, I think a lot of who I am is because of satisficing. And if I seem like I make weird decisions in life, for example, like not even continuing to pursue making money, it's because I'm satisficing. Like I really took took that lesson to heart and have shaped my life around it. So just for definition terms, right? Because people might think optimizing is trying to eke out the every last iota of improvement, right?

1:11:53But I think what we're really talking about is... Wait, sorry to interrupt. You know, like if you were to hear Paul McCartney go, hey, Jude, you'd be like, whoa, just to hear him sing two notes. To hear you go, optimizing. That's like, whoa. That's classic. It's a classic, you know. And if that is my legacy, so be it. Optimizing. Optimizing. I think what we're talking about is where to focus your finite energy on improving versus leaving things as they are, right? In a sense, right? Because I think optimizing, when I think of optimizing, optimizing is leading to optimal. What does that even mean?

1:12:35Maybe it's open-ended, so it just continues forever. but it's a helpful word. I'm just curious how you currently think about where to focus your energy on improving externally versus leaving things be. And this is a conversation that's near and dear to me. One of my most effective friends basically has said, I'm paraphrasing, but he's like, yeah, I optimize for like one or two things and everything else is good enough. Like I just have to get it to good enough. And that's it. And he's incredibly effective in life. And he's also a very happy guy in general. Hard to know how much of that is out of the box versus due to the decisions and the way he views the world, but seems to contribute.

1:13:23So how do you think about then where you might maximize versus where you satisfy? Because I know it's not good enough across the board. I find that hard to believe. What do I maximize? I'm not sure. or maybe maximize as to polarizing a word. No, you know what I think it is? Yeah. If it's really fun. Okay. If you think it's just actually really fun to like, maybe some people set up their, well, let's just say they get into bread making and they're just like, I want to set up like the best bread making. They're just having fun with it. Then great. They can maximize, you know, people who get really into high fidelity audio and they nerd out and they know it's stupid.

1:14:04Usually. Yeah. And they're just like, I don't care. I want this thing with the gold-plated cable connector. Right. And I think if you have fun optimizing, then it's worth it. If maximizing that is, if the process is fun to you, I think that should be the parameter. But I think that saying enough, good enough, is a superpower. Yeah, I really do. I really agree with that. You know what is such a good lesson to learn? Is that nobody cares what you're not good at. Okay, say more. like publicly, you're going to be just known for a few things that you're good at. All those things that you're not good at, nobody cares that you're not good at them.

1:14:43So just let it go. Now, for the broader public, I think that's really useful. But you may have, say, a significant other who cares about some of the things that you're not particularly good at. There is that. I mean not that I'm recently single and thinking about this all the time or anything we have spent many hours talking about sex while walking in the forests of New Zealand sex and relationships well even before this podcast Derek's setting up all these cameras and all this stuff and then he's like I just need to take a quick shower and I was like wait a second are we about to have sex Derek what's happening I haven't had a shower since yesterday It's feeling greasy.

1:15:30It's distracting. But no, it's funny. I wasn't sure if you were going to say, so, as you were saying yesterday in the forest about sex. Oh, no, no, no, no. We'll leave that aside for scotch outside of recording. The unoptimized life. What effect has that had on you paying more attention to that? Leaving good enough alone. Because this is something I would like to do more of. And I've tried to focus, with some success, on making fast, especially reversible or trivial decisions. If it can be undone easily, this is also with money, attention and money. I'm going to default to speed with a lot of things.

1:16:15If it's not that important or if it's pretty easy to reverse. I think that's been helpful. Off the top of my head, I think how important it is to be done with something so that you can move on. Like, I don't want... Open loops. Yeah. Unresolved decisions, sitting unresolved, sitting undecided for a long time. Yep. I feel the weight of those. Unfinished projects, because I'm trying to make it perfect. I feel the weight of those. I've learned the importance of just getting things done and finishing. And to do that, you usually have to say good enough. I love the fact that we say somebody releases an album.

1:17:00You release a book. Because there's a wonderful double meaning in that word, right? I've never even thought about that. Released. Yeah, I like that. So I think about that with anything I post on my site, any of my books. It's like, alright, it's released. It's good enough. Alright, I'm going to combine this. Maybe another... Sivers-ism. It's not really Sivers-ism, but in terms of how Professor Sivers operates in the world, useful, not true. We've been talking a bit about this. I wanted to save a lot of it for this conversation with the mics. Where should we start with this? All right. So again, I'm addressing the audience for a second.

1:17:38So, you know, I figure I'm coming on the podcast. This isn't just one of our random conversations. This is for the audience. There's a reason we're hitting record. It's for them. We can talk freely without hitting record. 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 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.

1:18:20It's skepticism. And so I'm going to 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. Remember all the bullets come his way. He's like, oh, wait, right like none of these rules apply to me that's deep skepticism it's empowering it's liberating so what i'm going to do for a few minutes including a little stories is to play morpheus to help emancipate the listeners so yes i call this useful not true but yeah there we go number one so okay i'm going to tell you the four bits first and we'll use that to kind of make sure that we come back to this.

1:19:05So number one, almost nothing is objectively true. Number two, beliefs are placebos. So you've got to believe whatever works for you now. Number three, rules and norms are arbitrary games that can be changed. I'm preaching with converted that one. And number four, refuse ideology. You need to accept ideas individually. There's the structure. So number one, so almost nothing is objectively true. So here's what's true. My hand is on the table, But what's not true is it's good to do everything in moderation. Here's what's not true. Family is everything. Here's what's not true. My mother abandoned me.

1:19:43Here's what's not true. AI is the future. So all of these things, people say them as if they're true. Or even when people make an excuse like, you know, I would be more successful if it weren't for my family, you know, or my location or whatever. People say these things as if they're an indisputably true fact. But to me, the only thing that's true are the things that both a cat and an alien, or let's say a cat and an octopus, would agree on. You've come up with so many children's books ideas in this conversation. The cat and the alien. The cat, the alien, and the octopus. Because it makes you realize that everything else is just mental interpretation, right?

1:20:23Like, there we go. This is on the table. This is true. But everything else, including, watch this one. Am I flipping you off right now? Like, am I angry at you right now? No, just because I'm... He's giving me the middle finger. Yeah, sorry. I'm holding up my middle finger with the back of my palm towards Tim. Even if people say things like, I hate you, does it mean that they hate you? No, it just, they said three words. That's all that actually happened. Their mouth said these words. You can't, everything else is an interpretation or a projection. So we have to consider why people are saying these things.

1:20:58If you start to think why they said something, it helps to dispel it. You can say, oh, you know what? They're probably just believing whatever supports the emotions that they want to feel right now. So if somebody has a belief that family is everything, maybe it's because that was something they told their kids because they want their kids to take care of them when they're older. So they want their kids to believe that family is everything. But they have a self-serving reason to believe that. Yeah, possibly subconscious, right? Right, right. Oh, so I'm so glad you said this. have you heard about the split brain stories that people...

1:21:31Yes. Okay. Why did you get up to have a glass of water? That type of stuff. Can I tell it? Yeah, please. Yeah. So this is so important to understand that... These are crazy. These are so bananas. Actually, we'll start with the other one since you know that one. Well, no, no, but the audience doesn't. No, no, no, but we'll do both. But during brain surgery, the patient needs to stay awake. And so there was a woman... And some, yeah. Or I guess they could, yeah. I don't know the details of this. It was on the Econ Talk podcast that during brain surgery, they were poking around in there and suddenly the woman started laughing.

1:22:07The patient started laughing and they asked, why are you laughing? And she said, oh, well, it's just, it's really funny the way that that curtain is hanging. And she really thought that the reason she was laughing is because that's the way the curtain was hanging. But it was actually because they were poking a stimulating part of the brain. And so the split brain patients, there's some people whose left and right hemispheres of their brain are not connected. So they've done tests on these people to say into their right ear, please get up and open the window. And they'll get up and open the window.

1:22:37And then they'll ask their left ear, or maybe it's their eye, why did you open the window? And they'll say, oh, it was just a, it was a little cold in here. I hope you don't mind. And they really sincerely to the core thought that's the reason they opened the window. Yeah. There are a couple more examples of this, you know, a message shown to one eye and they did something, then they asked the other eye, why did you do that? And every time the people make up a reason, they don't know they're making it up. They give a reason why they did that. And they feel completely confident that that is the reason why they did it.

1:23:07So to me, this is the most beautiful example, like we actually don't know. So talk about deep skepticism, radical doubt. You shouldn't even believe anything you tell yourself, even in your private diary, when you're saying, I'm not happy in this location, or I can't do this because of that, or I'm mad at so-and-so, you need to ask yourself, okay, that might not be true. Just because I'm saying it, it might not be true. So number two, beliefs are placebos. So two people in the same boat, one can say this sucks and another one can say this is great. But neither one is true. No beliefs are true. In fact, you know, the little story of Richard Branson, And before there was Virgin Airlines, you've heard the tale that he was at an airport and a flight to somewhere was canceled.

1:23:54Right, it was delayed. Yeah, and everybody was grumbling, ah, this sucks. And so he kind of went to the 20 people that were angry and said, hey, if I charter a plane, will you guys split the cost? And I said, yeah. So everybody else was angry. He looked at the same situation and said, this is great. That was kind of the launch of Virgin Airlines. No, not launch. You know what I mean? The Genesis story. Genesis, nice word. So no beliefs are true. When we say, I believe, it's an indicator that what we're about to say next is not true. Or not evidence-based. Right? Not true. Sorry, I'm just having fun.

1:24:31Have fun. Because, yeah, not evidence-based. Because we don't say, I believe in potatoes. Speak for yourself. Because there's a potato. we don't need to say it because there it is it exists so I think that whenever we say I believe such and such it indicates that whatever we say next is not true it's kind of like when science is at the end of a field's name generally it's not science not always but very often that's not the case I can think of a few exceptions neuroscience computer science but very often when science gets appended to something it's like ooh thou doth protest too much so since no beliefs are true I think this is liberating to realize that you can just choose whatever belief works for you now that helps you be who you want to be.

1:25:22This is about personal empowerment. This is a little bit hacking yourself. If a certain belief will help you be who you want to be, right now, you don't need to keep believing it tomorrow. You could believe it for three minutes or three days or the rest of your life. You're going to find what you look for. So if you choose to believe something, you'll find evidence to support your belief of anything. So the number three is that rules and norms are arbitrary games. So this is the one where I can't help but think of, you know, your introduction to the world in four-hour workweek, giving so many wonderful examples of how you don't have to accept the world's norms.

1:25:59Yep, for sure. But it's funny how many times the rules of the world are stated as if they're absolutely true. Like all applicants must submit their application through the usual channels and wait to hear from us. Or to be an expert in your field, you should have an advanced degree from a university. But someone made up these rules, and most people follow those rules, but they're not true. They're just not absolutely true. So I think that realizing they're not true gives you an incredible advantage because you realize you can make up the rules. So this is that matrix moment where the bullets are flying out, but anyways, he goes, wait a minute, this is just code.

1:26:38Somebody made this up, but I don't need to run this program. But if you do that, people are going to be upset at you. So somebody's going to get mad at you, and you have to know that even when they say you're a bad person for doing this, you have to know that that's not true either. And I have a cute story about that. This, I think, begs a number of questions living in a broader society about morally acceptable or reprehensible behavior. But that's, when I talk about like being who you want to be, we can't really address people who want to be psychopaths or who want to be damaging. Because then anytime you taught anybody how to do anything, how to fly a plane, hey, don't fly it into the World Trade Centers, okay?

1:27:22How to drive a car, hey, don't drive it into a crowd of people, okay? You have to just understand that we're talking about a tool, not your psychosis that might lead you to be a bad person. Right. I'm going to table that for a minute. So I have a funny little story that felt almost too risque to tell. I love too risque. Let's do it. Why don't I record these in front of a crowd? I can always edit. Oslo, Norway. My band was on tour and we were there for three nights. And for the first two nights, there was this girl in the audience that was kind of making eyes at me on stage. And so the second night I went to go talk to her and we hit it off and we hung out all night long and it was wonderful but we didn't have sex that's funny i was like can i say this on the air we did not consummate our attractions yeah all right i'm just gonna say it but we kind of regretted it so then it was the third day and it was the day that i was leaving and there's this big kind of central park in the middle of central oslo and we're in the park and you know housekeeping came at 10 am like time to check out time to go i'm like and she was asking them in norwegian I'm like, please, one more hour.

1:28:31And they said, no, get out. And she's like, oh. So we go out to this park and she's like, oh, God, I wish I could be with you. I wish. And she's like, God, I just so want to be with you. And I was like, damn, me too. I was like, I wish we could. And then I looked around and this park is surrounded by like, you know, Sheraton, Hilton, Marriott. And it was 11 o 'clock and my ferry was leaving at four o 'clock. Oh, and there's one detail. she was just in the process of breaking up with her fiance. A small detail. So this matters because I said, hey, what do you think about getting a hotel for a few hours?

1:29:10She was like, well, we could. I was like, yeah, it feels kind of naughty, doesn't it? I'm like, yeah, but let's do it. Yeah, okay, you don't mind? She's like, but I can't be seen with you. She said, just on the chance that a friend of mine walks by, I can't be seen going into a hotel with some strange man. I said, okay, so here's what we'll do. I'll go into the hotel, I'll get a room, and then I'll text you the room number and you come up a few minutes later. She said, okay, good. So I went into the hotel, and whatever hotel it was, I'll just say Sheraton. And he was like, welcome to the Sheraton Hotel, you know.

1:29:40And I said, hey, I'm here for one night. I'd like a room. And great, no problem. Okay, tomorrow breakfast will be served over here and such and such, and here's your room. And okay, he gives me my key. So I go up to the room and I text her the room number and she comes up five minutes later. So then we have fun for a few hours. And it's great. But now it's 2.30 and it's time for me to go get my ferry. So this time we reverse it. I go down alone first and I go to the guy at the front desk. And I said, hey, I've decided to catch the four o 'clock ferry. He's like, oh, is everything OK? Was there any problem?

1:30:13I said, no, no problem at all. Everything's great. Just decided to catch an earlier ferry. So paying in full. Here it is. So he's charging my card. It's already done. He's doing the thing. But then he sees her walk by. and he goes, wait a minute. I don't like this one bit. So he remembers that he saw her come in five minutes after me. Now she's leaving five minutes after me. And he goes, this is not some two-bit establishment. This is a very reputable hotel. I do not like this. No, you must not. Dude, I don't like this one bit. He was getting really angry. And I was so happy because, not for the obvious, but like it was so liberating realizing that i've done nothing wrong nobody was hurt this is fully like consensual he's you know they were paid for their room and even though he's angry he can't get me in trouble like i haven't broken the law and i think that we so often as kids we spend so much of our life the first half of our life kind of deferring to authority and thinking that authority has power over us.

1:31:23And at a certain point, you realize that you're free, you're liberated from that. But as long as you don't break the law, even if people tell you you're a bad person, that it's not true. They're just saying that because of their rules or whatever. So this to me was a major turn pointing my life, realizing that I was liberated from authority and from judgment. So a couple of things. So the first is, I read a piece recently, I think the author's name is Ava, A-V-A, I don't know her full name, Book Bear on Substack, and the headline, the title of the piece, something like, on not disappointing myself.

1:32:04And it's a discussion of disappointing others, how disappointing others but not disappointing yourself is important. I mean, that's the kind of upshot of it. very well written, introduced to me by a friend named Mike. Thank you, Mike. So I'd recommend people take a look at that because I think it relates. Since you made mention of the fiancé, though, I want to stand in for some of the audience who will say, well, wait a second. You said you didn't do anything wrong, but we live in a society. We do follow rules. Otherwise, we are with the animals. So what is good, what is bad is based on societal norms.

1:32:39I'm sure there are people listening who are like, well, wait a second. You had fun for a couple hours with someone who is still engaged, how would you respond to people who find that morally repugnant? They had broken up, but we're still living together because she just hadn't looked out yet. Okay. All right. Okay. Fair enough. I wouldn't sleep with somebody's wife. Okay. Okay. Fiance either. Okay. Got it. But no, I know what you mean. But in those moments, you have to ask yourself, do I agree with this rule? Especially if you travel the world, what's polite in Japan can be rude in New Zealand and vice versa.

1:33:11These different ideas of what's what is the right and wrong thing to do, are completely arbitrary, and they change with geography. And so you get to kind of pick or choose, and you can choose to fit into the local norms, or sometimes you choose not to, because you disagree with them. It goes the same with individuals and people. You're liberated from others' norms. You can choose your own. 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 on some level, because nothing is objectively good or bad.

1:33:49Therefore, general mutilation of like 12 year old girls or whatever it is, is totally fine in that culture because the culture is different. Therefore I'm not going to object to anything like that because I am 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? I defer to Sam Harris. Okay. Did he ever talk about the moral landscape on your show? I don't think we've discussed it explicitly. So why don't you, if you wouldn't mind elaborating. Probably the best elaboration is to tell people to go search for Sam Harris moral landscape.

1:34:30The best TED talk I've ever seen. That is the one. Sam Harris, The Moral Landscape, so beautifully summarizes this idea of judging something morally objectively based on individual well-being. So utilitarianism, like greatest good for the greatest number of people type stuff. Yeah. He says it better than that. Yeah, I don't want to speak for Sam. But yeah, go find that talk. This is a, there's, I think, a tension sometimes in my mind between living a self-authored, unorthodox life that does not conform to convention for the sake of conforming to convention, while also trying to have some type of consistent moral compass.

1:35:22and that is why sometimes i'm actually very envious of people who are deeply religious it's like you're the rules right i mean you want to talk about paradox of choice like how much decision fatigue does that remove i'm actually very envious of that sometimes so how do you think about i'm not saying you should think about i'm just curious when let's just say outside of breaking the law you can do anything right there is a it's just like having 1500 different types of toothpaste at the supermarket and having to choose one in a sense right there is a possible decision fatigue there. Do you use for yourself, you can define it yourself, but like good or bad or some type of moral framework for helping to narrow the choices that you make available to yourself?

1:36:03In secular societies, I think about it. I wonder about this a lot. Yeah. I recently read a book I can recommend for anybody called What Everyone Should Know About Islam. Okay. And it was really good. And it finally understood about the different Sharia laws. And it's really congruent. I think more than anything, if I had to pick one, word to give. It's amazing how congruent it is and what peace that can bring in a society where even the government laws are aligned with the religious laws, which are aligned. Like, everybody here agrees in this code. It's not a gray area. But you asked me the other day about, I said that I'm very influenced by the greater good, doing things that, even if it doesn't serve me personally or privately, if it seems like it's the right thing to do, I'll do what seems to be the right thing.

1:36:54Yeah. Yeah. And this is just for people who, this came up very organically in our conversation. I don't remember how, do you? Yes, I do remember. Because I think I was talking about how I do not identify as a philanthropist, even And I do a lot of nonprofit work because I actually have a pretty Hobbesian view of human nature in general. And to think we've probably, we certainly on a planetary level, caused more problems than we've solved. And therefore, I don't fill, like philosophy, right? Like hydrophilic. Like philic is to love. Phil is the etymology of that. And then the philanthropy is like the Anthropocene or anthropology.

1:37:40It's humans. So like to love humans, basically, is philanthropy. And I don't feel like I align with that. I'm actually like misanthrope a lot of the time. So I said, no, I don't think about that. And therefore, I make decisions about A, B, or C in the following way when it relates to some of the nonprofit work and scientific research that gets funded through the SciSign Foundation, my foundation. And that, I think, is what prompted you to say, I'm not sure if I think of myself as an altruist, but I seem to make decisions for the greater good, which I've observed in you. I think that is the rewinding the tape.

1:38:20I think that is sort of the stream of conversation that led to that coming up. I was asking about how you consider constraining your choices with maybe a lens of morality. And so you were going to say, well, yeah, for me personally, I guess I just, we have this gut feeling of what feels right and feels wrong. Or sometimes you actually let your head rule that decision to say, you know what? I know that personally I might want such and such, but I know that ultimately that's, it's not that important. Or maybe the fact that I'm happy anyway affects a lot of my decisions. that it's like, I don't need to have some million dollar thing to make me happy.

1:39:04I'm already happy. Like I've hit the maximum. There is no such thing as happier. I'm already there. So therefore this million dollars should just go to people who can use it because that's for the greater good. Like that's how my brain honestly works. But this idea of isms, ideologies and subscribing. Yeah. You tapped into that, that thing that we, what did you call it? The decision fatigue. It really helps decision fatigue to say i'm all in on this but i think that people do it to a fault where they read a self-help book and go oh yeah this is it this is the answer i'm following this now stoicism everybody's suddenly declaring themselves to be a stoic or religion or crossfit or veganism whatever right the biggest fault i think to crypto for that matter you want to talk about religion Yeah.

1:39:53It's tribalism in that case. Yeah, not for everyone, just to be clear, but yeah. So something related to you happened to me on a plane years ago that I think is a good example of this. That long, long ago, I think it was 2008 or 2009, I was on a plane from Amsterdam to the US and I saw a guy reading 4-Hour Workweek. I said, hey, great book. And he goes, it's trash, man. And I said, really? And he goes, this guy's full of himself. This book is trash. And I think about that all the time because... This is, was he a German guy? No, I don't know. I think, yeah, I've heard a bit of this before. So it's like, because he found one thing...

1:40:38Not to slight the fine Germans. I should say, outside of the US, Germany and Korea are my besties. But he found one thing he didn't like about you, and therefore declared all 400 pages of this book to be trash. Right. And I think that's the problem with isms, is that if you're trying to buy into a system, it's all or nothing. And so if the leader of a movement says something you don't like on social media, well, now the bubble's popped. It's a fly in my dish. It's a hair in the meal. It's a poo in the pool. The whole thing is ruined. Drain the pool. I think that's page four to seven in your Dr.

1:41:16Seuss. Right. Oh yeah, we're back to that. The cat, the alien, and the octopus. But it's like the mindset that wants everything to be a religion. Yeah. You know, and I think that's deeply built into people. Yeah, the reductionism. I mean, it simplifies reality. Yeah, simplifies reality. I like that. I mean, you do assume cognitive burden to take the harder path. So, on that note, back to my whole like useful, not true, my radical, what did I call it? Radical doubt? Super skepticism? Yes. I think we should be skeptical of every ism. I think we should avoid isms, avoid ideology, and take ideas piecemeal.

1:41:54Which means, ideally, you should be open to somebody you don't like taking their good ideas from people you don't like. And the people you do like admitting that some of the things they say, you're not going to adopt that. And when somebody does that, to me, that shows a stronger thinker, a clearer thinker, somebody who's looking at ideas individually instead of just saying, I'm all in on this. I am a such and such-ist. I subscribed to this-ism. That to me seems to be a jumping to a conclusion. It's a punt. It's like just deferring to the-ism. Yeah, this is very present for me in the US, and we don't need to go into politics, but with respect to politics, because I am asked frequently, are you a Democrat or a Republican?

1:42:43Oh, wait, I think you're a libertarian. I'm like, I refuse to play that game. If you want to talk to me about a specific issue, let's talk about it. And if you can not just make the case for your argument, but like, ideally, I mean, this is asking a lot, but like steel man account argument, just to prove to me you're not in this to have a shouting match. Okay, then let's have a conversation. But as soon as you apply, and I think I'm borrowing from Paul Graham on this of Y Combinator fame, but the more labels you apply to yourself, the stupider you get. I think that's true. It's just like the more you calcify your thinking and or just absolve yourself of thinking, which is a luxury.

1:43:26It's deferring, yeah. It's deferring, which is a luxury if you want to, I think, have a really, if you want to be an outlier in terms of the impact you have, the happiness you can achieve, that is a luxury you can't afford is absolving yourself of thinking. Maybe it's a bell curve, who knows? Maybe like the people who completely don't think and the people who think the most is the happiest who the hell knows. I think a lot of it's probably out of the box. How much of your, because there are, I'm sure people listening who are going to be like, wait a second, this guy can't be any happier. What kind of alien is this guy?

1:43:59How much of that do you think is out of the box? Just your code versus a cultivated? Do you know Sonia Lomberski? No. Okay. You know who she is? Nope. Oh, she wrote one of those books on happiness. Okay. After I read Stumbling on Happiness, I went, Ooh, that was good. That was a good book. And I went to go find other books on the subject. So she wrote a couple books on happiness. She's been studying happiness for decades. Sonia Lombowski? Lombowski, I think. Lombowski. I'll find it. Put it in the show notes. Show notes. Yeah, yeah, yeah. She said in one of her books that her studies have shown that most people's happiness is 50 % DNA and out of their control.

1:44:35And the other 50 % is in their control. So the best we can do is just control that 50%. And so, yeah, I think... Sounds like you're a stoic. Closet stoic. Oh, I am. Okay. Yeah, minus the ism. Yeah, right. But did I ever tell you about that? That you even talked about stoicism a bit, and I was like, ancient crap. And then finally, in 2010, I read A Guide to the Good Life. Yeah, William Irving, I think. I read it, and I was like, whoa, oh my God, I thought this was just me. Like, this is the, everything he's talking about, this is the way I've been thinking since I was a teenager. I don't know why I picked it up.

1:45:13maybe I suspect I found out years later that the Dale Carnegie book called How to Stop Worrying and Start Living. You know, I just as a side note, so I've read that book multiple times. I just went into my Kindle recently to look at my Kindle library, mostly to see like whether it was 70 or 80 % of the downloaded books that I hadn't read. And I came across that book and I thought, you know what, this would be a good time to revisit this. They're very overlapping. I just read a couple years ago in Wikipedia or something that that book was basically spouting stoic values. Makes perfect sense. It's a great book, by the way, folks.

1:45:51How to Stop Worrying and Start Living. By Dale Carnegie. And it was on my grandmother's bookshelf, and I read it when I was like 16. And so here I was thinking that up until two years ago, I would have said, or I did say, all the things that stoicism says. I've believed these things since I was a teenager. I thought I made these things up. I thought this was just me being weird. Wow. This was my weird approach to life. But then just two years ago, I saw that Wikipedia entry about... You got incepted by Dale Carnegie. Oh, wow. Inception, yeah. Wow. So the point is, I've been thinking that way since I was a teenager.

1:46:25And it wasn't until the age of like 40 that I read an actual book on stoicism. Whoa, this is how I think. But that being said, it's healthier to watch out for whenever you find yourself wanting to jump all in to an ism, even if it's just a book that you just read. And if you find yourself blindly kind of saying, all of this, this is me, this is how I'm going to live now. Unless you have the, let's call it self-awareness or meta-awareness to say, okay, I'll try all this stuff on for size. This is like me putting on a suit. Right, right. To see what happens, but not like this is the truth in all caps.

1:47:04This is who I am, identity. That's totally different. See, that's pluralism versus monism. Like the monim is to say, monism is this, it's mystical. The number one is somewhat like magical and mystical. You know, one love, one world, one answer, one way. It's very appealing, this idea of one. And it's very upsetting to think that, no, no, no, there are many answers and they conflict. And you can believe conflicting things at the same time. Sorry, I accidentally skipped answering your question about, was it either, am I this happy, or why am I this happy, or why do I think I'm this happy? Yeah, so this researcher who wrote the book, after stumbling on happiness, said 50-50, and then I dragged us into Stosis.

1:47:48So that's that. So no, I think I got the lucky roll of the dice, the DNA dice. But also, there's another thing I've been doing since I was a teenager that I found out has another name, too. So for my whole life, I very often open my diary and just put everything into there. I write what happened today, but also like the things that I'm thinking. And whenever I come upon a belief that to me feels like a disempowering belief, something that I've said - Your own beliefs. Yeah, my own, something I've said, it sounds disempowering to me. Like, I hate it here. I can't do what I want here. I need to go somewhere else to do what I want.

1:48:25I'll just keep it general like that. Then I'll stop and ask myself like, wait a minute, is that true? That sounds like a disempowering belief. Let me push back on that. I think that belief might be holding me back. So I'm constantly doubting everything I write, doubting everything I think, doubting everything I say. And you do this in writing? Yeah, I do this. My fingers just fly in my, you know. So later, I found out that this is similar to cognitive behavioral therapy. So I've been doing this for decades, and now I just found out what it's called. So I just recently read a book on cognitive behavioral therapy and went, oh, this sounds like what I've been doing.

1:48:59Also in the all roads lead to Rome type of metaphor, for CBT, as I understand it, largely based on many stoic writings. Ah, right, right, that makes sense, yeah. So I recommend, and it's kind of the conclusion of the big arc I was on, the whole useful, not true, super skepticism thing, is you asked me last week, how do you change your beliefs? Like if you say, this is the belief I'm holding, this is the belief I'd like to be holding. Right. You said, like, how would you recommend somebody do that, or how do you do it? Yeah, how do you translate that into durable behavioral change? Because it's one thing to intellectually recognize, this is a disempowering belief, it would be much better for me to hold this other belief.

1:49:45It's one thing to achieve that and quite a different thing to implement that latter belief in a way that changes your behavior. So I think the stack up evidence. So first, you know, just writing in my diary about, I think I need to believe this. I think I need to believe that the place I'm in right now is a good place to be, not a bad place to be. I think that would be a more empowering belief for me, that I can use where I am to do what I want, not need to escape where I am, for example. So then I need to just stack up evidence of this. So it's like once you've decided on the belief that would be better for you to hold, you can always find evidence to support any belief, right?

1:50:21So you could just kind of stack up evidence. And then I find that we're social beings. So talking with friends about it and asking their thoughts on this or telling them, like, I'm starting to think this. And then friends, if they care about you and they support you, will often give you other evidence to support the belief you want to have. Saying, you know, that's a good point. My friend Tracy such and such had this and she had this happen. So, yeah, I think you're right on with this new idea of yours. So friends support it and then you start to internalize it more. and maybe it takes a few days and you take some baby steps to put it into action or a big giant leap to put this into action.

1:50:55Like, you know, some crazy things I've done in my life to cut off some options in my life as a giant leap. We can talk about that if you want, but small actions or big actions, you can take the action before necessarily internalizing it. Totally. Going to fake it before you make it. Fake it before you make it. Yes. Even if you decide like... Do it before you believe it. act as if... I should sign up for college. And you're just like, you're right, I should. Oh my God, I just did. Even before you've convinced yourself, you can sign up that little form and take that first step to take that. So I think I've done a lot of things like that in my life where to support a new belief, I will take an action first.

1:51:33And then we all have the desire to be congruent with the actions we've taken. So it's like, oh, look, I'm this kind of person now. This is my belief now. 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, which is very much this, and I found personally very useful, super, super useful. You teased, you didn't really tease, 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, Is there an example of a giant leap that might make for a story?

1:52:14Is there? Yeah, I renounced my U.S. citizenship in 2011. That's a big one. As a way of, I deliberately burned the ships. Yeah. So I have to explain this metaphor because I found that most people haven't heard this tale. We have all heard of burning the bridges. 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.

1:52:55Of 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. So I wanted to challenge myself to go forward and not go back. And after 40 years in America, I 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. So I thought, I need to burn the ships. So I did. Okay, I'm laughing because there's so many rabbit holes we could go down here.

1:53:33I'm going to use my creative license as a host of this podcast to avoid most of them. But are you glad you did that? For years, it was one of my biggest mistakes in life. Made it hard to visit family and friends in the US, right? Yeah. I highly recommend when everybody asks me about it. Some people have found out about this. No, no. Handful more will know. Don't tell anybody. So when people would ask me about it, my advice was always do not do it. In fact, it still is. Somebody just asked me last week. I was like, do not do it. Kevin Kelly had this wonderful saying, the best option is the option that gives you the most options.

1:54:15Yep. I love that. And under that wise advice, I think that no, you should not renounce your U.S. citizenship because it's cutting off options. A lot of people seem to want to do it for tax reasons. And even that has, you need to look through that thoroughly. I did not do it for tax reasons. In fact, my taxes went up after I renounced because most of my income is still U.S. source. So now that all gets taxed at flat 30 % rate instead of before it was like part of a bigger picture. So yeah, my taxes went up and it reduced the options. So there was something scary that happened. Just a few months after I renounced my citizenship, my ex, her dad was like on his deathbed.

1:54:56and we needed to quickly get on a plane that night, but I didn't have visa. So I went to the U.S. Embassy to get a visa quickly and they rejected me. And I was devastated because they just hand you a slip saying, no, you've been denied for a visa. Next. And the slip says, you may not reapply. This decision is final. And hey, useful, not true. I challenged that rule. I was like, all right, I think somebody just made that up. I'm going to go back and reapply anyway. So I went back with a mountain of evidence and luckily they granted me a visa. Mountain of evidence for what? I was living in Singapore at the time, and it was actually my good friend from Bangladesh that said, Derek, this is your first time being refused?

1:55:31She's like, I've been refused like five times. Look, here's how to do it. You can't just go to the embassy and say, give me a visa, please. You have to show a mountain of evidence that your life is in Singapore, that you have, tell them about your cat, that you have a job, that you have this, that you're on the board at this company, that you're speaking at, you know, National University of Singapore. Show them your two-year rental. You're not a flight risk. Right. Not a flight risk. So I went back with a mountain of evidence and a letter from the doctor, from my ex's dad saying, you know, please, he only has a few days to live.

1:55:59Please allow them to come back. So I was granted the visa, but it was scary as hell. And so I think that people are often overconfident thinking like, hey, I'll just renounce my citizenship and it'll lower my taxes. I can go back anytime I want. But not true. Yeah, I always say like, no, no, no. Once you renounce, you might never be allowed in that country ever again. That is not your country anymore. So I do not recommend it. Yeah, I would say in general, not to pay too broad a brush, but the U.S. frowns upon people who renounce citizenship. Yeah, I'm always aware that I might never be allowed back in ever again.

1:56:34Yeah. Okay. What is another example of a giant leap? Anything come to mind? And that's a huge one, for sure. Moving? Was it worth it for you? So you said, I wouldn't recommend this to most people. And I know we live looking forward and not behind. We can't change the past as far as we know. Now, 13 years later, 12 years later since doing it, it did come in a little handy in COVID times where I will skip some family drama details, but there was a big, big pressure on me to move to America. and I was able to just kind of say, nope, can't do it. Don't want to, don't have to, can't. And so finally after 12 years, it came in handy for that.

1:57:29But no, to me, that was, it was a huge thing. And the other giant leaps? Giant leaps. Selling my company came in like an instant moment of clarity, of like, God, life is weird when it's like you can hold multiple philosophies in your head And at the same time, like this is, sorry, this is the whole thing I was talking about with useful, not true, is these no beliefs are true. So you can hold them all in your head and just kind of look at them like, well, here's one belief that says you should stick it out. When the going gets tough, you need to stay in there and such and such. There's another belief that says the rewards to effort ratio is off, that I'm spending so much effort and getting so little reward that you should stop.

1:58:12another philosophy says. And you can just hold these in your head and look at them as paths you could go down, as philosophies you could follow. And then ultimately you just pick one, or you craft one from a hodgepodge, a piecemeal from the other bits. And so in that moment, I was feeling really frustrated with my company. I'd been doing it for 10 years. I was feeling done. Like somebody who's been painting a mural for many years, or writing a novel for many years, and just you put the last brushstroke on, you write the last word, and you go, yeah, I think I'm done. That's how I was feeling. But somebody could have argued like, okay, go take a vacation and come back and get back to work.

1:58:49But I played off some different ways of thinking about it. And in that moment, while driving down Pico Boulevard in LA while on the phone with a friend, I was like, that's it, dude. I think I'm done. I'm just going to sell the company. And I decided in that moment, and it wasn't fully congruent yet. It was just one of many options. But that night I went and called three companies that had been asking to buy mine. And I told them yes. Was there a feeling or a meal or something your friend said that triggered that? He just asked me a bunch of questions. Like he challenged the things I was saying.

1:59:22He basically did the cognitive behavioral therapy with me. He was pushing back on everything I was saying, challenging it. So for example, I said, I'm sick of having all this responsibility. I don't want to have to do this and have to do that. He said, you don't have to do anything. I said, yeah, I have to pay my taxes. He said, no, you don't. I said, yes, I do. You have to be your taxes. He said, no, Derek, you need to understand this. You don't have to do anything. What's the dude, um, Power of Now that went, sat on a park bench. Who wrote Power of Now? Eckhart Tolle. Eckhart Tolle. Yeah, I never read the book, but I've heard good things about it.

1:59:53I unfortunately tried to listen to it on a long drive and don't do that. It's hazardous. It's got a very soothing voice. But he starts out the story saying that at one point he just went to go lay on a park bench and basically just sat there for a couple of years doing nothing. And it's a reminder that you don't have to do anything, that everything is a choice, that even paying your taxes, you don't have to. There will be consequences if you don't. But let's always be clear that you're choosing to do it. You're choosing to pay your taxes because you'd rather not have the consequences. You're choosing to pay your employees.

2:00:23You're choosing to go into work. None of these things are things you have to do. He pushed back on that a few times. And ultimately, my value system is such that I most value personal growth. And it felt to me like, I've been doing this thing for 10 years. the bigger learning, growing opportunity for me right now is to do something else. It wasn't a matter of up or down. It was just different. Yeah. So let's segue from personal growth to mentors. Because many people have had mentors. Many people seek mentors. Many people pine after mentors. And if they could only get a hold of person X and have a cup of tea or a coffee, pick the brain.

2:01:08Pick the brain. Pick the brain. So appealing. Have a meal. Who would not want to have their brain picked? Yeah. So how would you suggest people ask mentors for help? Here's what I do. I have three mentors. So anytime I had a little dilemma in my life, I write a really good description of my dilemma before I reach out to them. Because I don't want to waste their time, right? My mentors are VIPs. I don't want to waste a minute of their time. 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 got to make this succinct.

2:01:44I don't want to send somebody a 20 page long email. So I have to make this as succinct as possible. What does that in practice look like? A half page, page? Yeah, half page. Like bullet points for everything instead of paragraphs, right? Yep. As succinct as I can. And then before I send it to them, I try to predict what this person would say. So each of those three. 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.

2:02:21I'm going to address those in advance, again, to not waste their time. And when you say address them, what do you mean by that? Kind of 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? So it's like, okay, I knew you were going to ask that. So here's my followup. Right. So I'll address those in advance again, so as not to waste their time. And then again, one last time I tried to predict, okay, well now that I've addressed those. You have an answer ready for whatever they might come back with. But I include it in the initial summary of my situation.

2:02:50And then after I've done that whole process, I don't need to bother anymore because the answer is now clear. Because I've just done the work of summarizing everything and imagining what they would say. So, The truth is, I haven't talked to my mentors in years, and one of them doesn't even know I exist. These are my mentors. And so this is how I think. It's kind of like, what's his name? Napoleon Hill talked about the mastermind or whatever. Like, he was like, you know, imagine Abraham Lincoln is there. What would Abraham Lincoln say? Yeah, totally. So I think that, you're right. I also get a lot of emails from people saying like, I need a mentor.

2:03:29Will you mentor me? How do I find a mentor? And this is my answer. Like, it's all in your head. It's about the summarization of your situation, thinking of it from another person's point of view. You can predict what this person would say. If you're a fan of their books and their podcasts and their talks, you know what they would probably say. So do it yourself. Who is, if you're willing to share, the person who doesn't know you exist? It was Tyler Cowan. ah i just emailed him two weeks ago to say thank you thanks for your years of service uh-huh for his continued inspiration and he sent me back a tiny little thanks seth godin is one he knows i exist we don't talk that often but i very often think like what would seth godin say he walks the walk he's another example of someone who walks the walk very much so not as common as you would hope yeah no that's it who's the third it's actually changing i don't know right now keith richards bjork what would you chuck your cheese that would be great you know that's thoroughly useful nicodemus you have a fictional a fictional person can be your mentor yeah you know like what would you know what would jesus do right yeah like people still do that like okay i'm not sure what to do what would jesus do that's a perfectly good mentor yeah and i think a lot of people would agree with you.

2:04:47And for those people who might wonder, I actually do something very similar. Okay. Can you tell? Yeah, absolutely. So I have, I try to spend time with people I admire and aspire to be more like in some capacity, right? Because I do think you become the people you spend the most time with. So to bring up a name that we've already brought up, I think actually a lot about Matt Mullen, right? Cause he's very calm in almost all circumstances. Not all. I know a handful of things that bother him, but he's very, very calm and measured and good at perspectival knowledge, taking alternative positions, taking the counter position on his own thoughts, his own opinions, his own goals.

2:05:36So I often think when I get dysregulated or upset about something, I'm getting wound up. I'm like, what would Matt do in this? What would Matt say to me? If Matt were in my shoes, what would Matt do? And I've also done that in writing exercises where I actually just sit down with my older self who has figured it out. So if I'm talking to a version of myself who's 10 years older, 20 years older, who has figured this out, what might that older, wiser version of me say? And I just write out the dialogue. and by the end i'm like huh okay doesn't always give you some magic solution but it is astonishing how often that will give you some type of clarity or maybe relief that helps you to cling less strongly to whatever the challenge or problem or question was that you had in mind it's really It's really remarkable.

2:06:37I do something very similar, I guess, is what I'm saying. Sometimes even just asking. I get emails about once a week where somebody asks me a big question by email, and then at the end they say, actually, you don't even really have to answer this. Just honestly asking you the question helped me get some clarity. Thank you. Yeah, totally. Just the act of opening their email client and starting with it and going, okay, I want to ask Derek Sivers this thing. Yeah. Even if I intend to reach out to a mentor about something, I still go through the exercise of trying to crystallize my thinking so I don't waste their time.

2:07:10Even if it's a really close friend, like I don't, I don't want to be lazy and I don't want to ask them something that could be resolved with five minutes of Googling or five minutes of introspection. It's like whenever I go to anyone, I want to be able to say, basically here's the situation. Here are some of my assumptions. Here's what I've already tried. like I've tried A, B, C, D, and E and I'm not quite figuring it out and then followed by a super specific question but the asking the mentors around your imaginary table and doing that homework I think it's something that I do and I recommend to everyone and there is some selfish motive here like I would like to have fewer than several thousand email rate that come in with like how can I launch my book?

2:08:00Please tell me. And I'll admit, I actually got oddly shy two minutes ago when you asked me who the third one was, because actually it's been you in the past. Oh, wow. 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. I'm like, nevermind. Well, thank you. You know, I think about you. I think about you, Matt. It's funny you mentioned Seth, because Seth would be on a short list for me as well of people who really think, and more than think, it's question.

2:08:38Yeah. The musts, the shoulds, the have-tos. I'm like, wait a fucking second. That's nonsense. I feel like you're very good at that, which is part of the reason I've read your first book so many times. No, I'm all shy. Should we? I feel like we should do two things. Okay. I feel like we should get a slight refill on the scotch and then maybe talk about games, the games we play. All right. Getting good at games, things of this type. So a little bathroom and then scotch break.

2:09:16We're back. Cool. And for people wondering, we just came back from our bathroom slash break slash scotch refill. This is, I would say, very similar to a lot of our conversations. It's not that different 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. 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 yeah you're good at holding both looking at you but i'm thinking of them no offense wow we could we could unpack that for a while you and your euphemisms all right dark mirror here we come uh cheers man cheers so nice to see you Oh, thanks again, Matt.

2:10:11I don't know why we think Matt's there. Matt's got the fuzzy hat on, otherwise known as the boom mic. So we're all playing games. And I think it's a matter of knowing which games you're playing outside of some basics. You got shelter, you got food, and 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 want to play. These are important. why don't I just hand the mic over and let you talk about how you think about this kind of thing. Playing games. Maybe not the proper tee-up, but I'm going to go with it.

2:10:49No, that's what it is. So 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. You are pretty weird, in fairness. It's a compliment. But I try to explain that 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 catan or monopoly or poker whatever with friends when you win the game what do you usually do is you 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 no i probably shouldn't it's adorably uh addictive so my ex grew up on a farm And Stardew Valley is one of those little farming games where you tend to your crops and then you get animals and you get money for selling your crops.

2:12:00I think the story behind this game is also very interesting. Made by one guy with a passion for many years. I believe there's a lot of additional context to that that we don't have to unpack now, but people can look into it. It's a fascinating backstory. But yeah, don't play it because it's digital heroin. 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 like no bullshit games that don't ask you for more money once you're in. Yeah. You just pay your$9 or something like that up front and then you've got the game forever.

2:12:30Yeah, that's cool. That's cool. Let's 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. Yeah. 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?

2:13:11And so, yes, 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. 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. Okay. One hit wonder, Gautier 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.

2:13:56I 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. 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 just 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.

2:14:31She hit her point that was enough. Cameron Diaz, I suddenly after watching There's Something About Mary with 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, and then she'd had enough. And so she just quit to do other things. I should interview her. Yeah. I love those stories. I mean, she would probably not say yes, but I mean, those stories are fascinating. Yeah. Yeah. Because people are just like, yep, goodbye. Because I think there's something really admirable about the personal challenge of making yourself do something else that most of us stay in the game for too long.

2:15:08So 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 and 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. Which, I just have to say, it's definitely not suitable for family listening, but the audiobook is exceptional. I think it's Roy McMillan who's the narrator. And I know that because I looked it up because I was so impressed by the narrator. But just listen, anyway, I just want to second. How's it not suitable?

2:15:47Well, I mean, look, you have a very particular, different orientation on these things, but most parents probably don't want to listen to an audio book that's like, yeah, and then I spent all the money on coke and horrors. Okay. That's what I thought you were thinking. That is one specific thing, but that's so wonderful that he admitted that. It's funny for that reason, right? Because he's so candid. in a way that you would not normally find in most books like this. And unapologetic on other things. The whole thing is refreshingly unusual. I enjoyed it. I love that book. Okay, so I interrupted.

2:16:21No, it was 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 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 key fork in the road moment for me where I just sold CD Baby, had a ton of money.

2:17:05It'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. Yeah. 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 I 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 the, 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.

2:17:43But I think we should all entertain the idea. We could say, I'm really good at this game, so I should stop playing. Mm-hmm. I'm excited to dig into this because there's so many facets that I want to hear your thoughts on. So first, I want to 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? You strike me as a very thoughtful, but in some ways, unemotional person.

2:18:25Wow. Not in a bad way. You don't have volatile emotions. You don't have strong displays of emotion. And that could be a misread. I admire that about you, by the way. Just the general, at least from the outside, maybe it's like the duck on the pond, right? Calm on the top and 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. That's true. And that's remarkable. And you seem to have a very, very, very low need for external validation. That's my perception. Yes, that's true. So that makes it odd, or for me, to hear you say I want to be famous.

2:19:13Because I'm like, what do you get out of fame if that's your constitution? 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 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.

2:19:55And 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? And I was like, wow. He's marking up the wrong tree. He's got the wrong guy. 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. Yeah. So how does fame fit in that?

2:20:30I think a little bit like the things that you talked about being competitive, like your personal tendency to be competitive. I think as a teenager, I was 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 Incredible musician. Yeah. I didn't want to be that famous, but like, I don't know, Brian Eno? That's a good fame role model where it's not like he'd get hounded walking down the street. And that was driven by a competitive drive. It was more just like, let's see if I can do it. Okay. You know, just with that spirit of like, I think I can do that.

2:21:12I want to try doing that. And it was also feeling that what I was doing musically was valid and worth hearing. And so a way for people to hear it is to. Someone was asking me recently, because I was describing how excited I was to see you. We haven't hung out in so long. It's been so fun to hang out. 12 years. God, it's crazy because we also interact virtually. So 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, what's he like? 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.

2:22:10Right? You're a ringleader in a circus. Musician. You're really good at imitation, voices, etc. You enjoy, you seem to enjoy performing. Almost everyone. And I do mean almost everyone. And I'm only saying almost 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 loved or needed or both external validation. I think it's a very uncommon combination, which is why I was asking you about it. Maybe it is because I just had that life shift where it's like I did it to a certain point.

2:23:01I 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. You know, like by my own definition, I was a pretty successful musician. 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 flips something in my head where it's like, I no longer need the attention from 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.

2:23:36But yeah, you're right. I still am socially skilled. I know how to get on stage and talk. Yeah, you're good at it. Really good at it. You're a combination of elements that I don't usually see together. It's very rare. Am I blushing? You're blushing. Could be the scotch. All right. So the next question that comes to mind for me is whether you've always been a satisficer to hearken back to 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 good at a game and you win, it's only natural you'd stop playing that game, is to me the je ne sais quoi, the spirit, the essence of a satisficer.

2:24:25There are people, however, who let's just say they want to be a grandmaster in chess. It's like, this is my game. I win. That is a win on the road of additional wins and mastery to strive to become the best in the world. Or there's another option, which is someone who has played a game for so long. Let's just say it's finances. 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, they've won the Oscar, they've made a gajillion dollars, done whatever.

2:25:15They 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. So I know this is a hodgepodge of a question, but it leads back to, I guess, the first, which is, have you always been a satisficer? Oh, wow. Okay. The sub-questions, we are reversing back to the end. Yeah, this is a whole series of things wrapped in one. In fact, if you don't mind, I think I might end up answering in whatever order. 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.

2:25:56I think it's just objectively you need to change now. You need to shake it up in order to live a full life. Yeah. You 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 change. Just because it's not true doesn't mean it isn't valuable. Right. It's useful. Or I should put a different one. Just because it can't be proven is true doesn't mean it isn't valuable. I know we're going to get into some semantic rat hole here, so continue.

2:26:28I'll let that go. 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, 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.

2:27:15Those 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. Or like you're good enough, go to an ashram for two years, you can always come back, you'll be fine. But just imagine the joy of, God, sometimes even a simple manual labor. what it 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, you know, picking weeds in a garden because he used to be the emperor, but the Chinese revolution would never assign him to just be a gardener now, and he kind of found his peace with it.

2:27:46And 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. You know, I know there are other impressive things I could have done, but this meant the most to me. What really drove that home for me is I'm an enthusiastic student of history, and I read, for instance, I guess it's Genghis Khan, but who really knows? I don't speak whatever Mongolian or whatever the language would have been. Genghis Khan and the Making of the Modern World. Mm-hmm. Great book, yeah. Yeah, really good, especially the first half or so.

2:28:23It's really exceptional. but I realized because they mentioned Alexander and the Great in that book and I realized Alexander is kind of like Madonna it's got one name I don't know that dude's last name do you? and like I've pulled audiences not a single person has ever raised their hand I'm like okay this is ostensibly the greatest well certainly one of the greatest but let's just say the greatest conqueror the world has ever known given the constraints and technology at the time can't even name his full name So it's just like that impressive, I don't know, I've just become less and less kind of concerned with that.

2:28:59Okay, wait, there were some sub-questions in that last one. I can rewind. Which, by the way, is totally developed skill. That's not something, this is after doing a lot of podcasts. 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, what, how the fuck did you remember that? Yeah, totally trained. Yeah, which is wild. So I was asking you, maximizer versus being satisficer. Have you ever been a maximizer? Yeah, so just like I think you can't preach minimalism to somebody who hasn't felt the pain of having too much stuff.

2:29:38They 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 satisficing. that 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've felt the pain from doing this now.

2:30:15I need to learn how to say good enough. 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 city 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.

2:30:46And 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? Well, for you it was, right? Minimizing regret. Yeah. Two hours. 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 Waitzkin is not a satisficer. I am glad that he went all the way down the rabbit hole. So I'll tell you, I don't think you'd mind.

2:31:20So I believe that it is Josh who actually said that to me, where he's like, I basically focus on like one or two things. Oh, that makes sense, yeah. And then the rest? Right, because he's so intense about those couple things. Good enough. Yeah, I mean, you have to, right? He's another one who walks the walk in a big way. Right. Yeah. Have you met Josh? No. He's a mortal for me. You guys would hit it off. He's one of those invisible mentors. Not like, you know, officially, but I loved his book, The Art of Learning. Yeah. I've listened to his interviews and I really admire him. And so I have many times wondered, like when I've hit some kind of dilemma or situation, like what would Josh Waitzkin do in this?

2:31:57Yeah. I mean, no social, doesn't read email. There are so many conventions that he boxes. It's really inspiring. 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 Waitzkin is not good at and he just doesn't matter. Good enough. but have i always been like this no i think i had to feel the pain what did you used to maximize at any point i think 10 years ago i overthought the where to live 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.

2:32:45It's 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, but I learned all about them. I even know what it takes to move there. And 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.

2:33:17So 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. Parked up. 11 years now. That's wild. It's good enough. Yeah. I mean, there's a lot to be said for it. I want to say for people listening also that you might think, good lord like this is pretty head in the clouds one percenter stuff in the sense like that doesn't apply to me that's crazy but so i would just point out that god i got this from a documentary it wasn't helvetica which is a great documentary about typefaces and fonts and so on really cool doc there's another one about industrial design and there's an expression in that that stuck with me to this day i think it was from a company or one of the founders of frog design but i could be getting that wrong.

2:34:08And it was the extremes inform the mean, but not vice versa. Something along those lines. It's like when they're designing, say, garden shears, they're not designing for the average person. They're designing for the edge cases. So it's like the old paraplegic woman who needs to use it from her wheelchair. And then the, I'm making this up, like the 350 pound bodybuilder who like can't brush his teeth because his arms are too big. Okay, if you design for those edge cases at opposite ends of the spectrum, you cover everyone. But if you design for the average person, your error rate is going to be really high.

2:34:42And so I've thought about that in so many different domains. So in this case, I'm saying you're providing, from a socioeconomic perspective, an edge case, right? Like, broadly speaking. But there are principles in that exaggerated state that are easy to see, that are harder to see in some of the cases that are closer to, let's just call it the middle of the bell curve. So I would just say that we're exploring these things and the experience of this over-optimizing and paradox of choice and burnt cycles on something like location, I think everyone listening can find somewhere. They can find some place where they're over-optimizing in that way.

2:35:28Thanks 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'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 yeah i can hold on to that question.

2:36:14Maybe it's too late. I don't give a shit. Fire away. 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, uh, women like sex, right? Forgot about that. 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 and 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.

2:36:56And 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 like 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? Fuck yeah, that's what I would tell my former self, but that's just me. I don't think that's the question. The question is what advice would you give me, right? You. No, I'm saying when someone says, what advice would you give your younger self? Right. But they're really asking is, what advice would you give someone who is not where you are, but who wants to be where you are?

2:37:31I think that is the translation. What advice would you give someone who wants to be where you are? but it's not where you are? Like, how do I get where you are? I think that's what people are generally asking, right? Because they don't give a shit what your younger self would do. They care about what they would do, rightly so. But the answers are actually very different, if I'm being honest. The answers that I would give to some person whose specifics I don't understand are very different from the advice I would give to my younger self. Right. Because in my case, having a history of some very extreme depression and near suicide in college and so on, my advice would be related to self-preservation and recommending perhaps certain tools like meditation, like consistent, which I had on some level, but I think I could have tripled down on consistent exercise, perhaps supervised psychedelic therapies, etc.

2:38:32which don't apply to everybody. They just don't. I mean, I think some of those things might apply to some people, but if someone's really asking like, how do I achieve X? How do I have the life that you have? Number one, I would say you don't actually know what life I have. You get the highlight reel and you get what I share in podcasts, but you don't have the full picture. So be careful what you ask for. Number two, I don't understand the assumptions embedded in them wanting X. Because if their assumption is, let's just say, and you and I have seen this in ourselves and our experience and the experience of many others, once I have X amount of money, all my problems just disappear.

2:39:17The vapor of mist hit by the rising sun, all my problems just vanish. And that is an incorrect assumption. But if somebody's just asking that at a Q &A at South by Southwest or something, you don't have the time. You don't have the space to unpack all of that. So any answer you give is going to be hopefully helpful, but it could be really misdirecting in a way. It's funny, the nature that these questions come to us in 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 in somewhere in Argentina and a phone call comes in and says, how do I get there?

2:40:01How do I get to where you are? I think, well, depends where you are. Are you in Brazil? Are you in France? You know, 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? The only honest answer is, well, it depends. It's not a soundbite. So is the question, you clapped your hands, is the question you wanted to ask what question I think people are asking when they ask. Yeah. Yeah, you answered that. Thank you. Because I've always wondered, it's like, how do I think of that question? I keep getting that question all the time on podcasts.

2:40:34I'm like, damn it, this question again. It's like, what I would tell my younger self, I think it came up again just two weeks ago. It comes up a good amount. Yeah, I need a good answer for that. Without the snarky saying, I don't understand the question. Yeah, it's not a bad question. And it's just so context specific that it's not just sometimes unhelpful, but I think dangerous to give too broad a response. Yeah. To use your sort of geographic metaphor, right? You just send somebody off in completely the wrong direction. Go east. Go east. Take two of these, come in the morning. Oh shit, I'm in Antarctica.

2:41:10Sorry about that. Yeah, I thought you were in France.

2:41:16can you go east from antarctica how do they do directions

2:41:22yeah i mean unless you're at the south pole you can give you could give those i suppose it gets a little tricky but the good news is there's pretty much nobody there so you're not going to be giving too many directions to people they're they're going to be they're going to be at some type of base of some type. I've only been once to Antarctica. I actually recorded a podcast in Antarctica in an outdoor tent with someone, a field biologist and photographer, which is super fun. You know what? I owe all roads lead to Matt Mullenweg. I owe him thanks yet again for getting me down there. It was one of my favorite episodes of yours, that conversation with Matt in Antarctica.

2:42:03Oh, yeah. You know, actually, I recorded two. I did one with Matt and I did one with, I want to say her name was Sue Flood, but I could be blanking on the name. This amazing photographer. Wow, two podcasts in Antarctica. Yeah, that was fun. That's what I was asking. Yeah, yeah, that was also, if I know Matt at all, I know that there's probably some scotch involved with that as well. I like how my son spent time with you in 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 16? Yeah, what do 16-year-olds do? How do 16-year-olds walk and behave?

2:42:40Do you want to explain the context? We took him to see John Wick 4. So we went to see John Wick 4. Turns out that in addition to biosecurity in New Zealand, the people at the movie theaters are really strict. Yeah, weirdly. That was off point for New Zealand. New Zealand is a wonderfully casual culture. And 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 in. Even though he's seen and memorized all the John Wick movies. Yeah, he's seen all the previous ones. He's seen much worse.

2:43:16He'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... I'm 16. 16-year-olds behave. We were fortunate. We had some sort of zoo animals in the form of three other 16-year-olds nearby. And so he was trying to mimic it. And I was like, okay, you're very smart. You're very verbally intelligent. He's a very clever kid. And I was like, but the body language and the energy is not at all matching a 16-year-old. So we got to work on this a little bit.

2:43:55He had pulled the sleeves of his sweatshirt, his hoodie up. And I was like, I'm not sure that's helping. It might be hurting. You look very conspicuous. And then he'd pulled down the sleeves to make his arms look longer, but the proportions were all wrong. So he looked kind of like E.T. And I'm like, I think you're drawing more attention than you want to draw. But the whole thing was very cute. 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. Yeah. And your answer when I asked you what makes you emotional was anything related to parenting.

2:44:28Yeah. If you guys have ever seen or go see the song Papa Ute by the Belgian musician Stromae, 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 was crying. Yeah, you're kind of tearing up right now. Yeah, yeah. Wow. Yeah, it's serious. Which is new in my experience of Derek Severus. It's like seeing this. Why do you think that is? it's so important the stakes are wow yeah shit wow yeah new experience gotta 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 shit we're not in any rush zero rush hmm it's funny also collecting my thoughts on how to say this i don't have to um explain it much nobody's asked directly.

2:45:26It'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, like ignored, might pass on that scarcity of spirit, you know? Holy shit, I'm not doing this for the media. This is not like trying to be a captured moment. Holy shit yeah thank you for answering that this is new also i'll say for folks what a gift that you have something that you respond this way to yeah it's kind of the only thing i do my ex after we broke up said like wow i've known you for so many years i've never seen you get mad i've never seen you cry i've never even really seen you get upset 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 it's not a obviously like not an upset cry it's like holy shit this is such a big deal Derek we've covered a lot I'm just saying I don't I don't feel like we need to cover anything more is there anything you'd like to to say any requests to the audience anything at all before we wrap up you're gonna 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 and they emailed to introduce themselves.

2:47:12And here it is 10 years later. Now I'm in Bangalore and we finally meet. And it was so damn rewarding. And similar thing, it's like I went 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. 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?

2:47:54You know, 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 sive.rs, yeah, just send an email and introduce yourself. That's my surprising conclusion. Do other domains point to that? It used to be sivers.org. Yeah.

2:48:30You still have that, I assume. Yeah, I'm keeping that forever. But that's my minimalism thing. At one point I looked at that, I'm like,.org. Where is RS? Serbia. Republic of Serbia. Okay. But one of my favorite tech sites is Lobsters. L-O-B-S-T-E dot R-S. Okay. I was like, hey, Lobsters. Wait, what the hell is Lobsters about? Oh, it's just a random domain name they got, but it's programmers and sysadmins talking tech, and it's fun. It's like Hacker News minus the business. Oh, I hope I didn't send a bunch of traffic there, right? Yeah, I looked at the.org. I used to have Sivers.org, and I looked at that.

2:49:04I 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.R-S. All right, so Sivers with a dot between the E and the R. Yeah. Perfect. Yeah. Thank you, Derek. So nice. It's so good to hang out and have some scotch and... And make me cry, holy shit. Talk life, yeah. That was my first time in like three or four years. I've never seen you cry. yeah wow exclusive to the tim ferris podcast folks i'm just trying to help out my friend you know get him some more views yeah more views i'm all about the views it's so good to hang man you too thanks hey guys this is tim again just one more thing before you take off and that is five bullet friday would you enjoy getting a short email from me every friday that provides a little fun before the weekend.

2:49:59Between one and a half and two million people subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I've found or discovered or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums perhaps, gadgets, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange esoteric things end up in my field, and then I test them, and then I share them with you.

2:50:37So if that sounds fun, again, it's very short, a little tiny bite of goodness before you head off for the weekend, something to think about. If you'd like to try it out, just go to tim.blog slash Friday, type that into your browser, tim.blog slash Friday. Drop in your email and you'll get the very next one. Thanks for listening. This episode is brought to you by Shopify. Shopify is one of my favorite companies out there, one of my favorite platforms ever. And let's get into it. Shopify is a platform, as I mentioned, designed for anyone to sell anything anywhere, giving entrepreneurs the resources once reserved for big business.

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