#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”

Brought to you by Allbirds http://allbirds.com incredibly comfortable shoes, Wealthfront http://wealthfront.com/tim high-yield savings account, and Shopify http://shopify.com/tim global commerce platform providing tools to start, grow, market, and manage a retail business. Derek Sivers (@sivers https://twitter.com/sivers) is an author of philosophy and entrepreneurship, known for his surprising, quotable insights and pithy, succinct writing style. He is a former musician, programmer, TED speaker, and circus clown, who sold his first company, CDBaby, for $22 million and gave all the money to charity. Derek’s books (How to Live, Hell Yeah or No, Your Music and People, Anything You Want) and newest projects are at his website: sive.rs http://sive.rs/. His upcoming book is Useful Not True https://sive.rs/u. Please enjoy! P. S. To follow the exact step-by-step "Tech Independence" instructions from Derek, please visit sive.rs/ti https://sive.rs/ti. * This episode is brought to you by Allbirds http://Allbirds.com! Allbirds http://Allbirds.com are incredibly comfortable shoes, sustainably made, with design rooted in simplicity. I’ve been wearing Allbirds http://Allbirds.com for the last several months, and I’ve been alternating between two pairs. I started with the Tree Runners (in marine blue, if you’re curious), and now I’m wearing the Tree Dashers, and the Tree Dashers are my current “daily driver.” I stick with the blue hues, and the Dashers are in buoyant blue. The color pops, and I’ve received a ton of compliments. The Tree Dasher is an everyday running and walking shoe that’s also great for light workouts. It’s super comfortable, and I’ve been testing it on long walks in Austin and New Zealand on both trails and pavement. Find your perfect pair at Allbirds.com http://Allbirds.com today and use code TIM for free socks with a purchase of $48 or more. Just add a pair of socks to your shopping cart and apply code TIM to make the pair free. * This episode is also brought to you by Shopify http://shopify.com/tim! Shopify http://shopify.com/tim is one of my favorite platforms and one of my favorite companies. Shopify http://shopify.com/tim is designed for anyone to sell anywhere, giving entrepreneurs the resources once reserved for big business. In no time flat, you can have a great-looking online store that brings your ideas to life, and you can have the tools to manage your day-to-day and drive sales. No coding or design experience required. Go to shopify.com/Tim http://shopify.com/tim to sign up for a one-dollar-per-month trial period. It’s a great deal for a great service, so I encourage you to check it out. Take your business to the next level today by visiting shopify.com/Tim http://shopify.com/tim. * This episode is also brought to you by Wealthfront http://wealthfront.com/tim! Wealthfront is an app that helps you save and invest your money. Right now, you can earn 4.3% APY—that’s the Annual Percentage Yield—with the Wealthfront Cash Account http://wealthfront.com/tim. That’s more than eleven times more interest than if you left your money in a savings account at the average bank, according to FDIC.gov. It takes just a few minutes to sign up, and then you’ll immediately start earning 4.3% interest on your savings. And when you open an account today, you’ll get an extra fifty-dollar bonus http://wealthfront.com/tim with a deposit of five hundred dollars or more. Visit Wealthfront.com/Tim http://wealthfront.com/tim to get started. * [06:16] The Derek Sivers School of Enough. [11:24] Scuba diving and empathy lessons in Iceland. [16:13] Categories we apply to ourselves and others. [22:46] Derek’s people compass. [28:14] How to secure your tech independence. [1:05:19] The unoptimized life. [1:16:37] The meaning of Derek’s upcoming book, Useful Not True. [1:32:55] The problem with moral relativism and other -isms. [1:51:24] Giant leaps. [2:00:10] Finding and asking mentors for help. [2:08:18] Games. [2:12:26] The wisdom of quitting when you’re ahead. [2:17:13] Why would Derek — never in need of external validation — seek fame? [2:20:45] What makes Derek so darned interesting? [2:23:18] Has Derek always been a satisficer? [2:31:43] Living on the edge case. [2:35:33] The real question behind “What would you tell your younger self?” [2:40:29] Giving directions in Antarctica. [2:41:46] How do you teach an 11-year-old to act like a 16-year-old? [2:45:45] Parting thoughts. * For show notes and past guests on The Tim Ferriss Show http://tim.blog/podcast, please visit tim.blog/podcast https://tim.blog/podcast/?utm_source=podcast&utm_medium=podcast&utm_campaign=podcast-description. For deals from sponsors of The Tim Ferriss Show http://tim.blog/podcast, please visit tim.blog/podcast-sponsors http://tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday https://go.tim.blog/5-bullet-friday-1/. For transcripts of episodes, go to tim.blog/transcripts http://tim.blog/transcripts. Discover Tim’s books: tim.blog/books http://tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss https://twitter.com/tferriss Instagram: instagram.com/timferriss https://instagram.com/timferriss/ YouTube: youtube.com/timferriss https://www.youtube.com/timferriss Facebook: facebook.com/timferriss https://www.facebook.com/TimFerriss/ LinkedIn: linkedin.com/in/timferriss http://linkedin.com/in/timferriss Past guests on The Tim Ferriss Show http://tim.blog/podcast include Jerry Seinfeld https://tim.blog/2020/12/08/jerry-seinfeld/, Hugh Jackman https://tim.blog/2020/06/26/hugh-jackman/, Dr. Jane Goodall https://tim.blog/2020/04/16/jane-goodall/, LeBron James https://tim.blog/2018/11/27/lebron-james-mike-mancias/, Kevin Hart https://tim.blog/2020/05/20/kevin-hart/, Doris Kearns Goodwin https://tim.blog/2018/09/07/doris-kearns-goodwin-leadership/, Jamie Foxx https://tim.blog/2015/12/06/jamie-foxx/, Matthew McConaughey https://tim.blog/2020/10/19/matthew-mcconaughey/, Esther Perel https://tim.blog/2017/05/21/esther-perel/, Elizabeth Gilbert https://tim.blog/2020/05/08/elizabeth-gilbert/, Terry Crews https://tim.blog/2017/12/20/terry-crews-how-to-have-do-and-be-all-you-want/, Sia https://tim.blog/2020/08/12/sia/, Yuval Noah Harari https://tim.blog/2020/10/27/yuval-noah-harari/, Malcolm Gladwell https://tim.blog/2016/06/21/malcolm-gladwell/, Madeleine Albright https://tim.blog/2020/05/27/secretary-madeleine-albright/, Cheryl Strayed https://tim.blog/2017/03/30/cheryl-strayed/, Jim Collins https://tim.blog/2019/02/18/jim-collins/, Mary Karr, https://tim.blog/2020/11/11/mary-karr/ Maria Popova https://tim.blog/2014/10/21/brain-pickings/, Sam Harris https://tim.blog/2020/05/15/sam-harris-2/, Michael Phelps https://tim.blog/2021/01/21/michael-phelps-grant-hackett/, Bob Iger https://tim.blog/2020/01/16/bob-iger/, Edward Norton https://tim.blog/2019/10/31/edward-norton-motherless-brooklyn/, Arnold Schwarzenegger https://tim.blog/2015/02/02/arnold-schwarzenegger/, Neil Strauss https://tim.blog/2014/06/24/neil-strauss/, Ken Burns https://tim.blog/2019/09/12/ken-burns/, Maria Sharapova https://tim.blog/2017/08/26/maria-sharapova/, Marc Andreessen https://tim.blog/2016/05/29/marc-andreessen/, Neil Gaiman https://tim.blog/2019/03/28/neil-gaiman/, Neil de Grasse Tyson https://tim.blog/2019/10/03/neil-degrasse-tyson/, Jocko Willink https://tim.blog/2016/09/21/jocko-willink-on-discipline-leadership-and-overcoming-doubt/, Daniel Ek https://tim.blog/2020/12/03/daniel-ek/, Kelly Slater https://tim.blog/2020/09/08/kelly-slater/, Dr. Peter Attia https://tim.blog/2019/11/27/peter-attia-fasting-metformin-longevity/, Seth Godin https://tim.blog/2016/02/10/seth-godin/, Howard Marks https://tim.blog/2018/09/25/howard-marks/, Dr. Brené Brown https://tim.blog/2020/02/06/brene-brown-striving-self-acceptance-saving-marriages/, Eric Schmidt https://tim.blog/2019/04/09/eric-schmidt/, Michael Lewis https://tim.blog/2020/05/01/michael-lewis/, Joe Gebbia https://tim.blog/2018/03/08/joe-gebbia-co-founder-of-airbnb/, Michael Pollan https://tim.blog/2018/05/06/michael-pollan-how-to-change-your-mind/, Dr. Jordan Peterson https://tim.blog/2021/03/01/jordan-peterson/, Vince Vaughn https://tim.blog/2017/05/31/vince-vaughn/, Brian Koppelman https://tim.blog/2020/04/23/brian-koppelman/, Ramit Sethi https://tim.blog/2019/05/07/ramit-sethi/, Dax Shepard https://tim.blog/2020/11/18/dax-shepard/, Tony Robbins https://tim.blog/2014/10/15/money-master-the-game/, Jim Dethmer https://tim.blog/2020/05/18/jim-dethmer/, Dan Harris https://tim.blog/2020/11/19/dan-harris/, Ray Dalio https://tim.blog/2017/09/13/ray-dalio/, Naval Ravikant https://tim.blog/2015/08/18/the-evolutionary-angel-naval-ravikant/, Vitalik Buterin https://tim.blog/2021/03/08/vitalik-buterin-naval-ravikant/, Elizabeth Lesser https://tim.blog/2021/03/16/elizabeth-lesser/, Amanda Palmer https://tim.blog/2019/04/18/amanda-palmer-2/, Katie Haun https://tim.blog/2021/02/18/katie-haun/, Sir Richard Branson https://tim.blog/2017/10/09/richard-branson/, Chuck Palahniuk https://tim.blog/2020/09/02/chuck-palahniuk/, Arianna Huffington https://tim.blog/2017/10/18/arianna-huffington/, Reid Hoffman https://tim.blog/2015/08/31/the-oracle-of-silicon-valley-reid-hoffman-plus-michael-mccullough/, Bill Burr https://tim.blog/2017/09/17/bill-burr/, Whitney Cummings https://tim.blog/2015/06/26/whitney-cummings/, Rick Rubin https://tim.blog/2015/05/15/rick-rubin/, Dr. Vivek Murthy https://tim.blog/2020/03/26/vivek-murthy/, Darren Aronofsky https://tim.blog/2017/09/09/darren-aronofsky/, Margaret Atwood https://tim.blog/2022/02/22/margaret-atwood/, Mark Zuckerberg https://tim.blog/2022/03/24/mark-zuckerberg/, Peter Thiel https://tim.blog/2014/09/09/peter-thiel/, Dr. Gabor Maté https://tim.blog/2018/02/20/gabor-mate/, Anne Lamott https://tim.blog/2021/07/09/anne-lamott/, Sarah Silverman https://tim.blog/2022/01/12/sarah-silverman/, Dr. Andrew Huberman https://tim.blog/2021/07/06/andrew-huberman/, and many more. 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Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Tim Ferriss?

  This episode is brought to you by Allbirds, incredibly comfortable shoes, sustainably made with design rooted in simplicity. I am speaking from experience here. I've been wearing Allbirds for the last several months and I've been alternating between two pairs. I'm traveling with them right now. I started with the Tree Runners in marine blue, in case you're curious. And now I'm wearing the Tree Dashers and the Tree Dashers are my current daily driver. I wear them for everything. They're easy to slip on, easy to tie. Everything about them is just easy, easy, simple, simple. I stick with the Blue Hues and the Dashers in this case are in buoyant blue. The color pops. I've received a ton of compliments, but putting the color aside, the Tree Dasher is an everyday running and walking shoe. That's also great for light workouts.

• 0:43Tim Ferriss?

  It's super comfortable and I've been testing it on long walks in Austin. I've also been testing it on the trails and pavement in places like New Zealand. And let's come back to the sustainability. I mentioned that earlier. In the Allbirds Innovation Lab, they research how to make the most out of sustainable materials like leather made from plants, sugarcane and tree fibers. In fact, the Tree Dasher is made with eucalyptus tree fiber. That's something also found in New Zealand. Eucalyptus tree fiber to create a lighter and more responsive shoe. Allbirds is making shoes better than natural. They are supernatural. Find your perfect pair at allbirds.com today and use code TIM, that's T I M, for free socks with a purchase of $48 or more. That's allbirds.com using code TIM.

• 1:27Tim Ferriss?

  A L L B I R D S dot com. One more time, allbirds.com using code TIM.

• 1:37Tim Ferriss?

  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. So what does that mean? That means in no time flat, you can have a great looking online store that brings your ideas, products and so on to life. And you can have the tools to manage your day to day business and drive sales. This is all possible without any coding or design experience. Shopify instantly lets you accept all major payment methods. Shopify has thousands of integrations and third-party apps from on-demand printing to accounting to advanced chatbots, anything you can imagine.

• 2:21Tim Ferriss?

  They probably have a way to plug and play and make it happen. Shopify is what I wish I had had when I was venturing into e-commerce way back in the early 2000s. What they've done is pretty remarkable. I first met the founder, Toby, in 2008 when I became an advisor, and it's been spectacular. I've loved watching Shopify go from roughly 10 to 15 employees at the time to 7,000 plus today, serving customers in 175 countries with total sales on the platform exceeding $400 billion. They power millions of entrepreneurs from their first sale all the way to full scale. And you would recognize a lot of large companies that also use them who started small. So get started by building and customizing your online store, again, with no coding or design experience required.

• 3:06Tim Ferriss?

  Access powerful tools to help you find customers, drive sales, and manage your day-to-day. Gain knowledge and confidence with extensive resources to help you succeed. And I've actually been involved with some of that way back in the day, which was awesome, the Build a Business competition and other things. Plus, with 24/7 support, you're never alone. And let's face it, being an entrepreneur can be lonely, but you have support. You have resources. You don't need to feel alone in this case. More than a store, Shopify grows with you, and they never stop innovating, providing more and more tools to make your business better and your life easier. Go to Shopify.com/Tim to sign up for a $1 per month trial period.

• 3:48Tim Ferriss?

  It is a great deal for a great service, so I encourage you to check it out. Take your business to the next level today and learn more by visiting Shopify.com/Tim. One more time, Shopify.com/Tim, all lowercase.

• 4:04Tim Ferriss?

  At this altitude, I can run flat out for a half mile before my hands start shaking.

• 4:08Derek Sivers?

  Can I ask you a personal question?

• 4:10Tim Ferriss?

  Now would be an appropriate time.

• 4:14Derek Sivers?

  I'm a cybernetic organism, living tissue over metal endoskeleton.

• 4:26Tim Ferriss?

  Hello, boys and girls. This is Tim Ferriss and welcome to another episode of The Tim Ferriss Show, where it is my job to deconstruct world-class performers of all different types. My guest today is a dear friend, and this turned into a very fun, very wide-ranging conversation, Derek Sivers. Derek Sivers, you can find him on Twitter @Sivers, S-I-V-E-R-S, is an author of philosophy and entrepreneurship, known for his surprising quotable insights and pithy succinct writing style. He has revised his bio. I love this, and this ties into what we talk about in the actual podcast. He is a former musician, programmer, TED speaker, and circus clown, who sold his first company, CD Baby, for $22 million, and gave all the money to charity. Derek's books, How to Live,

• 5:11Tim Ferriss?

  Hell Yeah or No, Your Music and People, Anything You Want, I love Anything You Want, and newest projects are at his website, sive.r s. And you can also type in Sivers.org, and it'll go to the same place, but he likes the sive.r s. And there are two URLs that didn't exist when we recorded, but he promised to create pages for them, and he has. So the first is a page for his newest book, Useful, Not True, and that is at Sivers, so sive.r s slash u. And the next is related to tech independence. So how do you get off of the cloud,

• 5:51Tim Ferriss?

  create your own tech independence? And you can find the details, the step-by-step, at Sivers slash T I. So again, that is sive.r s slash T I. And without further ado, please enjoy this very in-depth, very eclectic conversation with the one and only Derek Sivers.

• 6:16Tim Ferriss?

  Should we kick this party off? What do you think?

• 6:18Derek Sivers?

  Ready.

• 6:19Tim Ferriss?

  All right. So I thought we would start. First of all, cheers.

• 6:22Derek Sivers?

  Cheers. Nice to Matt.

• 6:24Tim Ferriss?

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

• 6:34Derek Sivers?

  Ooh.

• 6:34Tim Ferriss?

  Mmm. We have Scotch, we have Go Go Gadget Black Tea. What is this called again?

• 6:41Derek Sivers?

  Go Go Goa.

• 6:42Tim Ferriss?

  Go Go Goa.

• 6:43Derek Sivers?

  Yeah, Go Go Goa. It's so good.

• 6:45Tim Ferriss?

  Go, so we go.

• 6:45Derek Sivers?

  Like Goa, India, you know, the region.

• 6:47Tim Ferriss?

  Yes.

• 6:50Tim Ferriss?

  So this is otherwise known. I do have a backup of Diet Coke in case. This is Podcaster Speedball. So I expect this is going to be a fantastic episode. And for those who are not watching, or those who may not have video in front of them, we have two different sized Scotch glasses. And if you were to walk into Derek's kitchen, you would find a wide assortment of glasses, namely one other glass, which, which, which is yet larger. It's like a Russian nesting doll of three separate glasses. And those are the only glasses you have in the house.

• 7:24Derek Sivers?

  And I didn't buy any of them. They were just.

• 7:26Tim Ferriss?

  But please, please explain more.

• 7:28Derek Sivers?

  Oh, God.

• 7:29Tim Ferriss?

  Because you walk the talk of certain types of minimalism. There are those out there who may not believe some of it. I'm just saying, or maybe skeptical. Have a healthy skepticism. I'm telling you guys, he's got three glasses in this kitchen.

• 7:41Derek Sivers?

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

• 7:49Tim Ferriss?

  Yeah.

• 7:49Derek Sivers?

  Right? So there's only me and my kid here. And so you come over and you say, okay, let's make some Scotch. And you're like, do you have any? I was like, uh, no, that that's all I got. I just have these glasses and honestly, I don't even know where they came from.

• 8:01Tim Ferriss?

  But they work.

• 8:02Derek Sivers?

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

• 8:06Tim Ferriss?

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

• 8:38Derek Sivers?

  And only two. Again, it's this idea of enough. It's like I wear junk, basically home pajamas. I think of one of those pajamas, the big baggy T-shirt that somebody handed you to conference. And you would never wear that outside the house. But Michael Brown with an E in London. When I lived in London, right before COVID hit, I thought, you know, I'm living here by Sal Row in London. I'm about to leave England forever. I'm going to get a custom-made suit. So I looked at, um, what was his name? Sartorial Talks. It's an interesting YouTube channel about somebody diving deep into like the craft of fine clothing.

• 9:18Tim Ferriss?

  Tailoring.

• 9:19Derek Sivers?

  Yeah, tailoring. And so he recommended this guy, Michael Brown, in London. So, you know, I went to Michael Brown and he said, what would you like? I said, you're the expert. You know, just dress me. So he told me what to wear and I do.

• 9:32Tim Ferriss?

  And because I have a little bit more context here, and then he would ask, so what type of shoes are you going to wear? And you're like, what should I wear? Well, how are you thinking about X? And you'd be like, how should I be thinking about X?

• 9:42Derek Sivers?

  Yeah.

• 9:43Tim Ferriss?

  And this is something I've thought more and more about, which is, it's not so much quantity versus quality, because there's a whole spectrum, right? You can have things that are very good and you have half a dozen of them. I'm making this up, of course. You can have one thing that is the best, subjectively or objectively, and that's it. You have one. Or you could have a ton of things and you're like, hey, I don't care about this thing. So this is a disposable item or service or fill in the blank in my mind. So I think we'll probably talk more about this, but what comes to mind for me also, when I think about, say, your suits, they're great suits. You're happy with them. You look good in

• 10:24Tim Ferriss?

  them. And I think about, in contrast, my accumulation of ill-fitting suits, in part because my body weight has fluctuated so much in my life, right? I've gone from 145 to 220, in both cases being pretty lean. So I have like, kind of fat boy Tim jacket, and then I've got like, really, really skinny, emaciated Tim jacket, and then I've got things in between. But I don't need most of those and yet I still have them. Or, not from the perspective of fit, but Kevin Kelly. In his new book, which is, I think it's simply called Excellent Life Advice, something like that. And one of the bits of advice was along the lines of, yeah, you know how you have that bad pen? He's like, throw out the bad pen.

• 11:04Derek Sivers?

  It's so liberating.

• 11:05Tim Ferriss?

  Yeah. Don't have the bad pen.

• 11:07Derek Sivers?

  Yeah. It's about self-respect, isn't it?

• 11:10Tim Ferriss?

  Yeah.

• 11:10Derek Sivers?

  Even something as simple as a pen, when I've done that, I went, I'm better than this.

• 11:16Derek Sivers?

  I'm not going to make this, this pen is not going to rule over me any longer.

• 11:19Tim Ferriss?

  Yeah, yeah, yeah. You're only as good as the worst pen in your house.

• 11:24Tim Ferriss?

  So let's start with a story. And I have not heard this story because you began telling me and I said, no, I don't want to hear it. I said, let's save it. Scuba diving. That'll be my-

• 11:33Derek Sivers?

  Scuba diving?

• 11:34Tim Ferriss?

  Scuba diving. That'll be my cue.

• 11:35Derek Sivers?

  And what it taught me about empathy and identity.

• 11:39Tim Ferriss?

  Amazing. I'll listen to the TED Talk.

• 11:42Derek Sivers?

  All right, here we go. So I was in Iceland and I never had any intention to go scuba diving, but I was at that place in a Thingvæir Park, if you've ever been there, where the two continental plates meet, the American continental plate meets the Eurasian continental plate. And there's this deep fissure in the ground, but it's crystal clear water. So you can see all the way down. I was like, ooh, I want to go in there. It just looks like Avian spring water, you know, poured over rocks with nothing clouding the water. So I was in Iceland for a month, so I went to take scuba diving lessons. And the instructor was great. So it's dive.is. At the time, it was just him in his basement and it was me and one other guy learning scuba diving.

• 12:24Derek Sivers?

  So we did the practice in the swimming pool and we did all the theoretical stuff. You learned to scuba?

• 12:30Tim Ferriss?

  Yeah.

• 12:30Derek Sivers?

  Okay. And so the swimming pool was great and I love the fact that it's calm, that you don't need to panic about holding your breath. It's just slow and meditative. But then the first time we went into the cold ocean, and to be clear, I had to wear one of those giant dry suits that you like, you're like a spaceman with four layers of rubber and stuff over the rubber. So it's very claustrophobic. And then I get into the water and it gets down to about 20 meters. And I'm just like, oh God, do I hate this? I hate, I want to like, I need to go, I need to, I just want to go back at home. I want to be on the internet. I want to be emailing my friend. I want to talk to my friend. I just want to, you know, no, I just, I gotta get out of here. So I wrapped on his tank. And I went up to the top.

• 13:07Tim Ferriss?

  You pointed, you pointed to go up.

• 13:09Derek Sivers?

  Yeah. And I was just like, I tore off my mask. And I was just like, I said, I don't wanna, I said, I'm just gonna go, you guys go ahead. I'm gonna wait on the side there. You go ahead. I'll just wait. And he was so sweet. He was so cool. He looked at me and just stopped for a second and he said, Hold on a second, he said, it's a really nice day today. He said, look around, look at those mountains. And then he goes, see, it's a nice day today. He said, yeah, look, look at what a, look at what a beautiful area we're in right now. See, um, and then he said, you know, if you were to leave now, he said, I know you're flying back in seven days. If we're to leave now, you wouldn't be able to complete the training. And you wouldn't get your certification. I know you don't want that. He said, just relax for a second. It's all right.

• 13:53Derek Sivers?

  And so I just relaxed for a second, you know, you inflate your BCDs, so you're just buoyant and you float. And I went, all right, yeah, what was I scared of? So I went, okay, I'm ready. And so we go back down and I completed it. It was great. It was no problem. And I love being underwater. It's wonderful. So that was the completion of my training. The next day was my first official dive. So we're there with a dozen other people that have flown to Iceland from around the world, including this couple from Germany that were bragging about how many dives they've done. We've done over 100 dives. So they were acting like know it alls, but then they're like, oh, dry suit. We've never done dry suit before. And so they're getting into dry suit, the guys. It's, it's tough.

• 14:36Tim Ferriss?

  It's different. It's different.

• 14:37Derek Sivers?

  And so I get underwater, but this time I'm elated. I'm underwater, just where I wanted to be in that crystal clear fissure there in Thingvileir. I was like, wow. And at 20 meters down.

• 14:51Tim Ferriss?

  Which is for the Yangs, 60 feet or so. Which is pretty deep. I mean, that's, that's, that's a deep dive.

• 14:57Derek Sivers?

  The bottom of where you're supposed to go as a beginner. And at the bottom, I see the German girl by herself and her partner's not there. And I do the dive manners we're taught, where I gave her the okay symbol.

• 15:09Tim Ferriss?

  Yeah.

• 15:10Derek Sivers?

  And she gave the not okay symbol. And I was like, oh, wait, did I remember? And I was like, okay? And again, she goes, not okay. And I see her eyes are looking crazy. And I went, oh shit, I've been trained for this. Oh my God, I can do this. Okay. Held on to her BCD, held on to mine, inflated hers a bit, asked if she needed my mouthpiece. And she said, no, and helped her get up to the surface. And she gets up to the surface and she rips her mask off, just like I did. She said, I don't like this. I don't like, no, this is not good. I don't, I hate this. I feel bad. Now I want to go. And I said, I just imitated the dive instructor exactly. I said, well, hold on a second. I said, look around. I said, it's a really nice day. I said, isn't this great? I said, you see those mountains over there?

• 15:55Derek Sivers?

  I said, just relax a second. I said, I'm here with you. It's okay. And so she calmed down and I saw her go do the same thing I did and calm down. And then her boyfriend showed up.

• 16:05Tim Ferriss?

  Where the hell was the boyfriend?

• 16:07Derek Sivers?

  I don't know. But he took her away.

• 16:09Tim Ferriss?

  So you're on your own, babe. I'm out of here.

• 16:11Derek Sivers?

  I've accidentally missed one step in the storytelling of this that I should have included is the night in between those two days. I went home that night thinking, what the fuck? I think I just had a panic attack. I'm not one of those people. Like I have no respect for people who have panic attacks. Because usually panic attacks, to me, I think of like people who are just like, oh no, like my cake is late. I'm gonna die. And they freak out over shallow little things. And it seems to me like they have no perspective on life. So then I have no respect for that kind of silly panic. But I had just panicked and it was involuntary. It's like that night I had this moment of just like, wow, what does that mean? Am I a panic attack person now?

• 16:54Derek Sivers?

  Have I changed categories from a not panic attack person to a panic attack person? I just kind of fell asleep with no answers to that. So then, yeah, then the next day had this thing happen with a German couple. And I feel like that experience taught me two kinds of empathy. That we categorize people, like I just said, the type of person who has a panic attack. And we think of a category of person that's a, say, like depressed, fat, homeless, divorced, bankrupt. And you think, I would never be those things. I'm not that kind of person.

• 17:33Derek Sivers?

  But I thought, wow, like, a lot of these things are involuntary. It's not like somebody chooses to be depressed. And I realized I had been unfairly categorizing people the same way I had unfairly categorized panic attack people. Because now I am one, right? I've had that. Addiction. Somebody who said they would never be an addict. Then they find themselves addicted to something that seemed harmless at first. And they have to admit, oh, my God, I'm an addict. But then I realized that someday, these categories might be me. Or anybody else, if you're categorizing people, this might be you. But then the thing that happened on the second day, where there's another category that we don't think we could be,

• 18:15Derek Sivers?

  which is like hero, rescuer, leader, athlete.

• 18:20Tim Ferriss?

  Things with a positive connotation.

• 18:21Derek Sivers?

  Millionaire. Some people in the past few years have become millionaires, which is something that they held in a different category and thought, I'd never be that. And suddenly there, you have to admit, I'm a multimillionaire now. It's a category. So I realized that we can, even those categories can be involuntary, that you can suddenly be a rescuer, even if you never intended to be one, just through the power of imitation. So you can deliberately step into these roles by imitating others.

• 18:51Tim Ferriss?

  So how do you now think about labels that you apply to yourself? And I ask that in part because as you're speaking, I think of how it can not only be unfair to say, I'm this and not that, or that person is this and not that. But if you're applying it to yourself and you have very narrow categories, so you have very finely tuned labels, I think it makes you fragile. Because you are susceptible to the whim of chance in a way that I think is not particularly resilient. If suddenly your circumstances change and you find yourself in a different category,

• 19:35Tim Ferriss?

  it can be really upsetting. And

• 19:40Tim Ferriss?

  How do you think about what you call or don't call yourself? We were talking a little bit about this at lunch before we recorded, right? There are people who are like, I have read Stoicism and now I am a Stoic. And there's this identity that's assumed and these labels that are applied. And as much as I love Stoicism, even though I invoke that name,

• 20:02Tim Ferriss?

  I do think that you have to be careful with labels. So how do you think about that for yourself?

• 20:07Tim Ferriss?

  Well timed for a sip of scotch.

• 20:09Derek Sivers?

  Well, young man. Sit down.

• 20:15Derek Sivers?

  By the way, audience, the hardest thing about hitting record on this is that Tim and I have these like crazy all over the place conversations in the forest and whatnot, that it's hard to remember that we need to close tangents today.

• 20:26Tim Ferriss?

  Yeah, that's true.

• 20:26Derek Sivers?

  Usually we open a tangent and close it two days later.

• 20:28Tim Ferriss?

  Yep, that's very true.

• 20:29Derek Sivers?

  We have to close tangents today.

• 20:30Tim Ferriss?

  Okay.

• 20:31Derek Sivers?

  So do you want me to go on my anti-ism tangent?

• 20:34Tim Ferriss?

  Well, let's see. Is there some unfinished business that we need to tidy up first?

• 20:40Derek Sivers?

  There's a tiny idea around the identity, which is to just admit that whatever you are is now and whatever your preference is now. So like when my kid says, I hate tomatoes, I say, today. And he goes, oh, right. I hate tomatoes today because it's leaving open the possibility that you might change your mind tomorrow. And he did. I hate olives. I hate, hate, hate olives so badly.

• 21:05Tim Ferriss?

  You, Derek.

• 21:06Derek Sivers?

  And he picked this up from me, right? So he's like, I hate olives too. But he was just imitating me. And then we went to Subway one day. I was so proud of him. He walked up to the counter and he said, I would like olives. And they said, do you want anything else? He said, ham, just ham and olives. And they loaded this sandwich full of olives and I looked at it like horrified. He ate it and loved it. And he goes, I like olives now. It's like, yes, I love that switching between identities. And so I used to call myself an entrepreneur and other people would call me an entrepreneur. And then I did my first book that was about that. So I got categorized as an entrepreneur.

• 21:46Tim Ferriss?

  Great book, by the way.

• 21:47Derek Sivers?

  Thank you. Thank you for the foreword.

• 21:48Tim Ferriss?

  Anything you want, right?

• 21:49Derek Sivers?

  Yeah.

• 21:50Tim Ferriss?

  Yeah, I recommend, I recommend people check it out. I've read it multiple times. It's a great book.

• 21:55Derek Sivers?

  I love that you did the foreword.

• 21:56Tim Ferriss?

  Yeah.

• 21:56Derek Sivers?

  Thank you.

• 21:57Tim Ferriss?

  You're welcome.

• 21:58Derek Sivers?

  For years, I kept calling myself an entrepreneur until one day I realized, like, wait a second, this has expired. Somebody who was an athlete in high school can't keep calling himself an athlete forever.

• 22:08Tim Ferriss?

  Yeah, I've learned that one.

• 22:10Derek Sivers?

  You have to keep earning that title or it expires, right? Same thing with being a good friend. The same thing with any labels that we call ourselves. You can't just keep using that forever. You have to keep it up or it expires. So if you realize that your previous identity is expiring, you have the choice then of either admitting, I was an entrepreneur. I was a musician. Or if you don't want it to expire, well, then you need to do something about it. And like actively be a good friend, not just keep calling yourself a good friend or go actively be an entrepreneur if you want to keep calling yourself that.

• 22:46Tim Ferriss?

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

• 22:50Derek Sivers?

  Great.

• 22:50Tim Ferriss?

  But that's the nature of conversation, especially when you have Gogo Gadget tea and scotch involved.

• 22:59Tim Ferriss?

  We were talking about this the other night at dinner. Revising, say, we use language, we're creatures of language. I mean, part of the reason that we've become such a dominant pest on the planet is our ability to use concepts and abstraction. And you had mentioned at one point, thinking of yourself after entrepreneur as a writer. How did you make that switch?

• 23:25Derek Sivers?

  Looking to your heroes. I call it my people compass. If you're not sure which way to go, you can ask yourself, well, who do I admire? Who do I like?

• 23:35Tim Ferriss?

  Mm hmm.

• 23:35Derek Sivers?

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

• 23:55Tim Ferriss?

  I'll metabolize of your other focus.

• 23:58Derek Sivers?

  It was like, and as I'm doing my thing, if I learn some lessons, there I just put them into writing.

• 24:04Tim Ferriss?

  Yeah.

• 24:05Derek Sivers?

  But then I noticed that all of my heroes were authors. These were the people I looked up to the most. And that helped me realize my values, like it helped reveal my values. So ultimately, like, we want to be our ideal selves. And I think that your heroes are your idealized self. It's kind of, that's why we idolize certain people is we want to be like them. So 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?

• 24:49Derek Sivers?

  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. The way I think about it is asking yourself, what kind of people do I like being around?

• 25:08Tim Ferriss?

  Mm hmm.

• 25:09Derek Sivers?

  Because these are the people you're going to be serving. You have to like them.

• 25:12Tim Ferriss?

  Mm hmm.

• 25:13Derek Sivers?

  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?

• 25:19Tim Ferriss?

  Yeah, totally.

• 25:20Derek Sivers?

  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?

• 25:37Derek Sivers?

  If you think 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, you'd feel pretty mixed about it.

• 25:48Tim Ferriss?

  I'm a little embarrassed to tell you about my new startup then.

• 25:54Tim Ferriss?

  Right.

• 25:55Derek Sivers?

  So it's asking yourself, like, what kind of people do you want to be around?

• 25:57Tim Ferriss?

  Decentralized blockchain baby seal clubbing expeditions.

• 26:03Tim Ferriss?

  Not sure I want to hang out with the people who might go on that tour.

• 26:05Derek Sivers?

  Run by AI.

• 26:08Tim Ferriss?

  We may need to refill the scotch the rate we're going.

• 26:11Derek Sivers?

  That's gonna work. Pause. So, um, yeah, I think that if you set up your business to serve the people that you love being around.

• 26:19Tim Ferriss?

  Yeah.

• 26:20Derek Sivers?

  Even if it makes less money, you're going to be much happier.

• 26:23Tim Ferriss?

  Yeah.

• 26:24Derek Sivers?

  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.

• 26:36Tim Ferriss?

  Okay, so let's poke at that a little bit. Being around the people you love, there are many ways to do that.

• 26:40Derek Sivers?

  Mm hmm.

• 26:42Tim Ferriss?

  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?

• 26:53Derek Sivers?

  Because it's, it's asking yourself, what would you do even if it didn't pay?

• 26:58Tim Ferriss?

  Yeah.

• 26:58Derek Sivers?

  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 happen 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. Come on. So, all right, right now.

• 27:15Tim Ferriss?

  And now I like olives. Stop lecturing me about my past self.

• 27:19Derek Sivers?

  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.

• 27:31Tim Ferriss?

  Yeah, sure.

• 27:32Derek Sivers?

  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, um.

• 27:50Tim Ferriss?

  Oomph, go power?

• 27:51Derek Sivers?

  No, no, no, where somebody takes initiative. Somebody took the initiative.

• 27:55Tim Ferriss?

  Is that English? Go ahead. I don't speak Esperanto yet.

• 28:00Derek Sivers?

  Somebody took a little, and set up their own website. I like these people.

• 28:04Tim Ferriss?

  Yeah.

• 28:04Derek Sivers?

  I like people that have personal websites, that aren't doing it for money.

• 28:08Tim Ferriss?

  Yeah.

• 28:08Derek Sivers?

  They're my kind of people. And so I would be proud to serve them.

• 28:12Tim Ferriss?

  Mm hmm.

• 28:12Derek Sivers?

  So that's all I meant by that.

• 28:14Tim Ferriss?

  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.

• 28:30Derek Sivers?

  Yeah.

• 28:30Tim Ferriss?

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

• 28:37Derek Sivers?

  Central Wellington.

• 28:37Tim Ferriss?

  Well, yeah, the central area is a little bit like Haight 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 a 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. In any case, we were walking around, not in the, on the nature side of things, but downtown. And I said, you know, I'd love to ask you about cybersecurity.

• 29:20Tim Ferriss?

  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.

• 29:47Derek Sivers?

  Yeah, because I'm slow like that. You'll ask me something like that and in the moment, so we're walking down Courtney Place, I'll give some half ass answer. And then later that night, I'm like, ooh.

• 29:56Tim Ferriss?

  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.

• 30:15Derek Sivers?

  Yeah.

• 30:16Tim Ferriss?

  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 because in part, I think there are many people who feel, myself included, that there's something uncomfortable about it, but.

• 30:41Tim Ferriss?

  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.

• 31:00Derek Sivers?

  Mm hmm.

• 31:01Tim Ferriss?

  For a lot of reasons.

• 31:02Derek Sivers?

  Your phone book, your calendar.

• 31:03Tim Ferriss?

  All of that, all of that. It's there, 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.

• 31:18Derek Sivers?

  Poor Tim.

• 31:19Tim Ferriss?

  Poor Tim.

• 31:20Derek Sivers?

  Poor incapable.

• 31:23Tim Ferriss?

  All right. So, so Dr. Dr. Sivers, please hold court.

• 31:27Derek Sivers?

  So, audience, I prepared.

• 31:33Derek Sivers?

  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.

• 31:42Tim Ferriss?

  Yeah.

• 31:43Derek Sivers?

  Know this, know that.

• 31:43Tim Ferriss?

  Yeah, yeah, yeah.

• 31:44Derek Sivers?

  So, all right, guys, I prepared a couple hours and here you go. So I'm going to unapologetically read through 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. See, isn't that easier now? There, we've got your data.

• 32:08Tim Ferriss?

  Yeah.

• 32:08Derek Sivers?

  And it actually reminded me of something I think you said in Four Hour 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.

• 32:20Tim Ferriss?

  Yeah.

• 32:21Derek Sivers?

  Freeway.

• 32:22Tim Ferriss?

  Yeah, there's a lot of that in fitness overall, for sure.

• 32:24Derek Sivers?

  So.

• 32:25Tim Ferriss?

  There's an incentive.

• 32:25Derek Sivers?

  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. We'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're in a world that had more, it was 50 years ago.

• 33:08Tim Ferriss?

  Or now in a lot of countries, you still can't drive automatic.

• 33:11Derek Sivers?

  So 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 kid's photos in the cloud since the day his kid was born. He put everything under 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? He went, they're in Google Photos. She said, no, they're not. And he looked up, he's like, oh my God, what do 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,

• 33:55Derek Sivers?

  well, could you please recover them? And 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.

• 34:04Tim Ferriss?

  He can't trust those clowns.

• 34:06Derek Sivers?

  So, um, sorry, that was some snarky.

• 34:09Tim Ferriss?

  The clowns and the cloud.

• 34:10Derek Sivers?

  Escape the clown. Tech snark. Okay, so, um.

• 34:14Tim Ferriss?

  Oh, you do that on purpose?

• 34:16Derek Sivers?

  I did.

• 34:16Tim Ferriss?

  Oh, that was good.

• 34:19Derek Sivers?

  So, yeah, anytime when somebody talks about the cloud, you change it to an clown. 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.

• 34:42Tim Ferriss?

  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 I have spider holes dug in the backyard, I do not experience you to be a hyper paranoid person at 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 like, you know, gold bars and guns in the basement and he's this guy. Maybe, right? If, if I just would, I want to sort of set the proper reference point, which is I don't experience you to be a paranoid person.

• 35:13Derek Sivers?

  Not at all.

• 35:17Tim Ferriss?

  Just a quick thanks to one of our sponsors and we'll be right back to the show. This episode is brought to you by Wealthfront. There is a lot happening in the US and global economies right now, a lot. That's an understatement. Are we in a recession? Is it a bear market? What's going to happen with inflation? So many questions, so few answers. I can't tell the future, nobody can, but I can tell you about a great place to earn more on your savings and that's Wealthfront. Wealthfront is an app that helps you save and invest your money. Right now, you can earn 4.3 APY, that's the annual percentage yield with the Wealthfront Cash Account. That's more than 11 times more interest than if you left your money in a savings account at the average bank, according to FDIC.gov. So, why wait?

• 35:59Tim Ferriss?

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• 36:28Derek Sivers?

  So first, let me just say, the first thing you need is to get your own server, which is as simple as $5 a month. If you go to, there's a company I recommend called vulture.com, but it's spelled V-U-L-T-R.com.

• 36:41Tim Ferriss?

  Could use some branding help, but yeah.

• 36:44Derek Sivers?

  So, they have something called Cloud Compute for $5 a month, where basically that's setting up a private slice. It's just yours, but on a shared computer.

• 36:52Tim Ferriss?

  Okay, so it's like a virtual private server.

• 36:54Derek Sivers?

  Virtual private server, exactly. I was trying to not get technical.

• 36:56Tim Ferriss?

  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.

• 37:05Derek Sivers?

  It's not. It's just a computer that's always online. That'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. We'll get to that. The third option is go to any used marketplace and find an old used Lenovo ThinkPad,

• 37:49Derek Sivers?

  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.

• 38:04Tim Ferriss?

  Yeah, you have done some work.

• 38:07Derek Sivers?

  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. So 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-

• 38:38Tim Ferriss?

  Isn't it bondage, sadomasochism? So, no, no, sorry.

• 38:42Derek Sivers?

  Berkeley Software Distribution. Actually, a quick, I was born in Berkeley, California and kind of like more people named Dennis go into dentistry because there's an affiliation of names. Freakonomics pointed that out. I always wonder if my affinity with the BSD operating systems is because I was born in Berkeley. It's because 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

• 39:26Derek Sivers?

  system that doesn't do everything under the sun. It does this that I'm describing and it does it really well. And it's secure as hell.

• 39:32Tim Ferriss?

  And it's got, as I understand it, a few lines of code.

• 39:34Derek Sivers?

  Yes.

• 39:35Tim Ferriss?

  Right? Which means, let's just say you're a writer, the more you write, the higher the frequency of typos.

• 39:40Derek Sivers?

  Yes.

• 39:40Tim Ferriss?

  And you don't want bugs-

• 39:42Derek Sivers?

  Yes.

• 39:42Tim Ferriss?

  -in your code that can be exploited.

• 39:44Derek Sivers?

  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-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.com settings.

• 40:29Derek Sivers?

  You edit your firewall to only allow port 22, which is the port that SSH uses to connect. Once 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.

• 40:45Tim Ferriss?

  Can you explain the generated private key?

• 40:47Derek Sivers?

  Yeah. It's really just a single command you type on the terminal. If you type ssh-keygen, space, dash, t, space, 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, now it will, instead of asking you for your password, it just uses the private key and the public key matching to let you in.

• 41:19Tim Ferriss?

  Got it. So it's like Marco, Polo, okay.

• 41:21Derek Sivers?

  Yeah.

• 41:22Tim Ferriss?

  We're in, as opposed to entering a password every time.

• 41:24Derek Sivers?

  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.

• 41:37Tim Ferriss?

  Okay, this is, keep track where you are.

• 41:39Derek Sivers?

  Yeah.

• 41:39Tim Ferriss?

  Do you think this will become, and I'm non-technical, folks, you've probably guessed, but this type of Marco-Polo, I can't even remember the proper, the private keys and so on, private-public keys or whatever the term is, will become more and more prevalent as a...

• 41:56Tim Ferriss?

  Quantum computing and so on allows the current level of encryption to be decrypted more and more effectively. I'm just wondering about, well, this is going to take us off on a major tangent.

• 42:07Derek Sivers?

  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.

• 42:19Tim Ferriss?

  Yeah.

• 42:21Derek Sivers?

  So that's the way it should be. It's just, it is the best solution so far, I think.

• 42:25Tim Ferriss?

  Yeah, I'd go if you have a four-digit password on your phone, you can change that to eight-digit. Simple upgrade in settings.

• 42:31Derek Sivers?

  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-M-E.

• 42:42Tim Ferriss?

  You don't get 10% affiliate.

• 42:43Derek Sivers?

  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.

• 42:58Tim Ferriss?

  Pork Bun.

• 42:59Derek Sivers?

  Yeah, all three of these are really good reputable places to get a domain name. I recommend them. No affiliate fees at all. I just like them. I use them. Okay, so now you've got a server.

• 43:07Tim Ferriss?

  Hmm.

• 43:08Derek Sivers?

  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 oatmeal, 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.

• 43:33Tim Ferriss?

  Yeah.

• 43:34Derek Sivers?

  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. You think, I don't need your help.

• 43:42Tim Ferriss?

  For those people who listen to what you just said, and 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.

• 43:51Derek Sivers?

  Right.

• 43:52Tim Ferriss?

  What would you say to them?

• 43:53Derek Sivers?

  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 gonna work.

• 44:02Tim Ferriss?

  Look at that.

• 44:03Derek Sivers?

  So email me.

• 44:04Tim Ferriss?

  God damn it. Email you. Write a blog post, Derek Sivers.

• 44:07Derek Sivers?

  I will. No, I will. I will. Blog post? What's that?

• 44:11Tim Ferriss?

  Yeah, you've only written five million blog posts since like 1987.

• 44:15Derek Sivers?

  You know what? I registered the domain name cloudfree with the dot e for Estonia.

• 44:20Tim Ferriss?

  Yeah.

• 44:20Derek Sivers?

  For e. So I.

• 44:23Tim Ferriss?

  Like cloudfree.com wasn't available?

• 44:25Derek Sivers?

  I don't know. I just thought it was clever.

• 44:28Tim Ferriss?

  I don't care.

• 44:28Derek Sivers?

  Cloud for e. No, but someday I'm gonna write this up into a very simple. You don't need to understand this yet. Just do this. Eventually you'll understand it. Cause that's how I learned.

• 44:38Tim Ferriss?

  Where are my photos? Oh, Derek Sivers has all my photos.

• 44:40Derek Sivers?

  Right. That's what I really wanted. I want your photos. Cause that's how we all learned it first, right? It's often like, just do this. You'll understand it later.

• 44:49Tim Ferriss?

  Yeah.

• 44:49Derek Sivers?

  Now just do it. And I think that's a fine way to learn if you trust the source, right? Trust me. So it's not as hard as it sounds.

• 44:58Tim Ferriss?

  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 gotta try it a few times.

• 45:06Derek Sivers?

  Yeah. Okay. So, um, by the way, you know what'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.

• 45:17Derek Sivers?

  And he hit a homerun on his first try.

• 45:19Tim Ferriss?

  Oh, wow. It's all downhill from there. Tell him to stop.

• 45:21Derek Sivers?

  Yeah, exactly. Everybody was cheering for me, but I didn't know what I was supposed to do. They told me to run. Okay. So now let's talk about some applications. Okay. So you have a server set up.

• 45:28Tim Ferriss?

  Yep.

• 45:28Derek Sivers?

  Here's what you're gonna 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 Radikal, R A D I C A L E. The website is radical.org. It's absolutely free, open source.

• 45:51Tim Ferriss?

  R A D I C A L E.

• 45:54Derek Sivers?

  Yes.

• 45:54Tim Ferriss?

  Okay.

• 45:55Derek Sivers?

  Dot org. It's absolutely free, open source. It sets up what's known as a card dev and a Cal dev 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 and suddenly it says, okay, synchronized. And now every new contact you add and every calendar entry is synchronized with your server, not Apple's.

• 46:29Tim Ferriss?

  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.

• 46:43Derek Sivers?

  Mm hmm.

• 46:44Tim Ferriss?

  Huge pain in the ass.

• 46:45Derek Sivers?

  Right. You had to use a third.

• 46:46Tim Ferriss?

  So you would have to use a third party and at least I ended up using Cal dev a long time ago. That's since changed. But yeah, so this is not very hard.

• 46:55Derek Sivers?

  That's why I started with this. Yeah. It's like the simplest thing to set up.

• 46:59Tim Ferriss?

  And the most sensitive in a way, or some of the most sensitive.

• 47:01Derek Sivers?

  Yeah. 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 it 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. epub, JPG, 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.

• 47:45Derek Sivers?

  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 its 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. That'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.

• 48:27Tim Ferriss?

  I want to give you more scotch, just to see what it does to your spelling. There's gonna be a lot of spelling. Continue.

• 48:34Derek Sivers?

  So it's completely free and open source, and it does that more like automatic style instead of manual synchronization.

• 48:40Tim Ferriss?

  Well, let me pause. So in your particular case, do you think automatic sync? Do you like automatic sync?

• 48:46Derek Sivers?

  I like having the delay between my servers.

• 48:50Tim Ferriss?

  Because if you fuck up?

• 48:51Derek Sivers?

  Yes.

• 48:52Tim Ferriss?

  Right?

• 48:52Derek Sivers?

  Because 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 rsync or Syncthing, not just to clone between your computer and your server, but that server and the other server.

• 49:22Tim Ferriss?

  I have a great idea.

• 49:22Derek Sivers?

  Okay.

• 49:23Tim Ferriss?

  You ready?

• 49:24Derek Sivers?

  Yeah.

• 49:24Tim Ferriss?

  All right. So this next chapter of Dr. Cyrus. 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.

• 49:41Derek Sivers?

  I like it.

• 49:42Tim Ferriss?

  Anyway.

• 49:43Derek Sivers?

  I can't, you know, it's...

• 49:43Tim Ferriss?

  Just an idea. Who... Because you seem to be... Philosophically aligned with this.

• 49:49Derek Sivers?

  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 hands or the dependent on the server. It's about being dependent. It's about the self reliance. People who were dependent on others, like imagine if everybody in their own home were like dependent on somebody else to make them food. They didn't know how to make their own food. You'd feel bad for them like, come on, it's not that hard. Here's a knife. Here's some bread, some peanut butter. See, you could do it. You know, like, that's how I feel with these things.

• 50:17Tim Ferriss?

  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. There'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.

• 50:56Derek Sivers?

  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 felt, you know, 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? Like, you know, they're not these new salesmen trying to, you know, raise venture capital for their domain selling. These 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.

• 51:32Tim Ferriss?

  Manually?

• 51:33Derek Sivers?

  Yeah, I just type R sync right before I shut down my computer, packs 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 and like a whole week later went, oh, crap.

• 51:52Tim Ferriss?

  Let me ask a dumb question, maybe. Why delete anything? Storage is so cheap.

• 51:56Derek Sivers?

  Oh, I know. No, I mean more like deleted lines of code.

• 51:59Tim Ferriss?

  Oh, I see.

• 52:00Derek Sivers?

  Like, I thought I was done with that.

• 52:01Tim Ferriss?

  Right, there was a revision that you want to undo.

• 52:03Derek Sivers?

  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, no offense to, don't install WordPress. We love you, Matt. I adore you, Matt, but I think everybody should learn how to do it themselves.

• 52:26Tim Ferriss?

  Yeah.

• 52:26Derek Sivers?

  It's not that hard to do an H1 tag, H2, P tag, UL, ULI, Ahref, image source. You can learn it in an hour.

• 52:35Tim Ferriss?

  Yeah.

• 52:36Derek Sivers?

  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.

• 52:45Tim Ferriss?

  Well, hold on. Let's not to push back, but just to stress test a little bit. WordPress is open source. Why not use it?

• 52:52Derek Sivers?

  You could, but see WordPress is, I think, last time I counted, 38 billion lines of code.

• 52:58Tim Ferriss?

  Yeah.

• 52:58Derek Sivers?

  And it does way more than what you need. So it's kind of like if you said, I need some scissors. And somebody hands you to the contents of an entire hardware store. And 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.

• 53:28Tim Ferriss?

  Yeah.

• 53:29Derek Sivers?

  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. Because 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.

• 53:43Tim Ferriss?

  Yeah.

• 53:44Derek Sivers?

  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.

• 53:50Tim Ferriss?

  Yeah.

• 53:51Derek Sivers?

  And that's it.

• 53:52Tim Ferriss?

  Yeah.

• 53:52Derek Sivers?

  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 webpage even.

• 54:05Tim Ferriss?

  I think it's a good exercise, even if you end up later using something else.

• 54:08Derek Sivers?

  Exactly.

• 54:09Tim Ferriss?

  Right?

• 54:09Derek Sivers?

  That's what I was getting to.

• 54:10Tim Ferriss?

  Yeah.

• 54:10Derek Sivers?

  So start by doing it that way. And then...

• 54:14Derek Sivers?

  If you need something that another service offers, you'll recognize that you need it.

• 54:17Tim Ferriss?

  Yeah, totally. I agree with that. I mean, I edited the first 30 to 40 episodes in 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. Otherwise, how am I going to assess anything?

• 54:45Derek Sivers?

  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.

• 55:00Tim Ferriss?

  You can do that with G Suite, though.

• 55:01Derek Sivers?

  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 will 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. And 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 mail. 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.

• 55:45Derek Sivers?

  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. You'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.

• 56:10Tim Ferriss?

  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. Don't try this day one. Get familiar with the gear first. So I would be curious to know how you'd 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, but 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

• 56:52Tim Ferriss?

  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?

• 57:01Derek Sivers?

  Everything I've recommended here was recommended with that in mind. You should expect that you will outlive most businesses.

• 57:10Tim Ferriss?

  Yeah.

• 57:10Derek Sivers?

  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.

• 57:21Tim Ferriss?

  Yeah.

• 57:22Derek Sivers?

  Those of us who were around in the first dot com boom.

• 57:24Tim Ferriss?

  Yeah, history repeats.

• 57:25Derek Sivers?

  Yeah.

• 57:25Tim Ferriss?

  It's certainly well within the realm of possibility.

• 57:28Derek Sivers?

  Yeah, it was unthinkable in whatever 1999 that MySpace wouldn't be around. Or maybe, what was that, 2003?

• 57:35Tim Ferriss?

  So how is mailbox.org better in that sense?

• 57:38Derek Sivers?

  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'd just log into your domain name router and just route it to another service. Because everything's being sent to, you know, [email protected]. So you have your own domain name, you 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.

• 58:06Tim Ferriss?

  Right.

• 58:07Derek Sivers?

  So all of this is expecting everybody to fail.

• 58:09Tim Ferriss?

  Yeah.

• 58:10Derek Sivers?

  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.

• 58:24Tim Ferriss?

  Question for you. So 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 like, I want to do sort of a science project with some experimentation. What might you recommend to them?

• 58:49Derek Sivers?

  I'd say the first baby step is to get your own domain name.

• 58:52Tim Ferriss?

  Hmm.

• 58:53Derek Sivers?

  Definitely. And then. Move your email off of Gmail and just go to some third-party provider of email.

• 58:58Tim Ferriss?

  Okay, so you start with email?

• 59:00Derek Sivers?

  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.

• 59:30Tim Ferriss?

  Okay, question for you personally. If you had to choose between having your email off of the cloud or calendar and contacts, we can only choose one. So calendar and contacts come together. Email is another. Which would you choose?

• 59:50Derek Sivers?

  I don't know why there's a sense of happiness in having my calendars and contacts be on my own server.

• 59:55Tim Ferriss?

  Yeah, I lean that way too. And I don't know if I could verbalize why that's the case.

• 1:00:00Derek Sivers?

  Mail sending has been come unfortunately difficult because a lot of things get marked as spam unless you do a bunch of more complicated things.

• 1:00:07Tim Ferriss?

  That's right. I didn't think about that. I could see that being a huge problem.

• 1:00:09Derek Sivers?

  So the way I actually have my mail server set up right now, and I don't mean this to

• 1:00:13Tim Ferriss?

  Pretends to be Gmail?

• 1:00:15Derek Sivers?

  Well, can you imagine?

• 1:00:19Tim Ferriss?

  What could go wrong?

• 1:00:21Derek Sivers?

  All incoming email comes directly into my server.

• 1:00:23Tim Ferriss?

  Yeah.

• 1:00:24Derek Sivers?

  But for sending, I actually use a service called Mailgun that just handles the sending. So they take care of all the deliverability.

• 1:00:31Tim Ferriss?

  Yeah. So it's not an ESP, but it's helping, or maybe it is an ESP, like an email service provider?

• 1:00:36Derek Sivers?

  Oh, it is. Yeah.

• 1:00:38Tim Ferriss?

  Yeah, I guess there are.

• 1:00:38Derek Sivers?

  For outgoing only.

• 1:00:39Tim Ferriss?

  Yeah, I think, I wonder, I think SendGrid does

• 1:00:41Derek Sivers?

  Yeah.

• 1:00:42Tim Ferriss?

  Handle some of this as well.

• 1:00:43Derek Sivers?

  Yeah, they're one of the same. So you're really just using their empty servers just to send the outgoing mail or receiving it privately. So that's my balance.

• 1:00:50Tim Ferriss?

  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 are super great, clearly very smart. But I was like, I don't understand. This.

• 1:01:13Derek Sivers?

  Wait, can we tell people the Shopify?

• 1:01:17Tim Ferriss?

  Oh, man. I mean, my most expensive mistake ever?

• 1:01:21Derek Sivers?

  No, no, no. My little thing with Toby.

• 1:01:23Tim Ferriss?

  Oh, yeah, yeah, yeah.

• 1:01:24Derek Sivers?

  It's cute.

• 1:01:25Tim Ferriss?

  I'll leave, I'll let that one just float by.

• 1:01:28Derek Sivers?

  Sorry, I didn't mean to stir up a...

• 1:01:29Tim Ferriss?

  Yeah, selling Shopify earlier was my most expensive mistake ever as their first advisor when they had like 10 employees.

• 1:01:35Derek Sivers?

  So, so, audience, there was this cute moment.

• 1:01:37Tim Ferriss?

  Yeah, so we're gonna get to a cute moment. I just wanna say that also, God, do I love the Shopify guys. I just, 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. It just makes me so happy. So, cute story.

• 1:01:56Derek Sivers?

  Sometimes people ask if I can introduce them to you.

• 1:02:00Tim Ferriss?

  Yeah.

• 1:02:00Derek Sivers?

  And I'm like, no. I respect your time.

• 1:02:03Tim Ferriss?

  Yeah, I appreciate that.

• 1:02:04Derek Sivers?

  By the way, I love your email address.

• 1:02:06Tim Ferriss?

  Oh, yeah, yeah, yeah. It's basically says fuck off.

• 1:02:09Derek Sivers?

  Yeah, it's essentially [email protected].

• 1:02:14Tim Ferriss?

  It's not, yeah, it's not that aggressive, but it makes it clear, like, think twice before sharing an email.

• 1:02:19Derek Sivers?

  Don't you dare give this to [email protected]. That is his personal email.

• 1:02:25Tim Ferriss?

  Yeah, yeah. A little wordy, but you know.

• 1:02:27Derek Sivers?

  It's worth it. Give him a hurdle. So, um, oh, Toby. So, I love the Ruby programming language. And so, before there was Ruby on Rails, I learned Ruby in a cabin in Sweden that was offline for two weeks. So, I brought a programming book with me. I was like, well, I'm gonna 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. And there was news that there was this guy named David in Denmark who was doing something with websites and Ruby. So, I emailed him saying, hey, somebody said you're making like

• 1:03:12Derek Sivers?

  a web framework in Ruby. And he emailed back saying, not ready yet. That's all he said.

• 1:03:17Tim Ferriss?

  And for those who don't know, that's DHH, David Heinemeier Hanssen.

• 1:03:21Derek Sivers?

  Yeah. 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 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. So 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, alright, I'm in. And so my old company, CD Baby, we started converting everything over to Rails. I was like, this is great.

• 1:04:03Derek Sivers?

  So a couple of 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? Because I've got this little ecommerce thing I'm doing. I was like, ecommerce thing? No. I was like, sorry dude, I don't do that. No, I don't know. So I didn't introduce you guys. So I was thrilled later to find out that Toby's little ecommerce thing is Shopify. Or became Shopify.

• 1:04:31Tim Ferriss?

  Became Shopify.

• 1:04:32Derek Sivers?

  Became the Shopify. And then I was thrilled to find out like another year or two later that you were...

• 1:04:37Tim Ferriss?

  We met at RailsConf, of all places.

• 1:04:41Derek Sivers?

  Wow.

• 1:04:41Tim Ferriss?

  I was a speaker at RailsConf, which I felt I was supremely underqualified.

• 1:04:46Derek Sivers?

  They love doing that.

• 1:04:48Tim Ferriss?

  But I met him in the green room at RailsConf.

• 1:04:50Derek Sivers?

  Sweet.

• 1:04:51Tim Ferriss?

  Yeah.

• 1:04:51Derek Sivers?

  That's how you met. I was gonna ask you.

• 1:04:52Tim Ferriss?

  That's how I met. Wild.

• 1:04:54Derek Sivers?

  So Toby and I have emailed since and about like joking about, yeah, sorry I didn't introduce you.

• 1:04:58Tim Ferriss?

  Yeah, Toby's...

• 1:04:59Derek Sivers?

  It all worked out.

• 1:05:00Tim Ferriss?

  Toby's a spectacular human. Big, big fan.

• 1:05:03Derek Sivers?

  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 gonna talk about Unix, command line, terminal stuff anymore.

• 1:05:15Tim Ferriss?

  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. If you'd be open to going there next, what do you think?

• 1:05:32Derek Sivers?

  Yeah.

• 1:05:33Tim Ferriss?

  All right, let's do it.

• 1:05:34Derek Sivers?

  London.

• 1:05:35Tim Ferriss?

  London?

• 1:05:36Derek Sivers?

  2019.

• 1:05:38Tim Ferriss?

  This is gonna be good.

• 1:05:39Derek Sivers?

  On the train from Oxford to London. And it was one of those days that looked like it might rain, it might not. So we made a plan on the train. I said, okay, if it's raining, we're gonna go to the museum. And if it's not raining, we're going to the zoo. And he said, okay. So we got to Marleben 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, just walk around. Sure? Yeah, okay. We just walked around. So at every intersection, he said, let's go this way. So, 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.

• 1:06:24Derek Sivers?

  At another time, in like a little alleyway, he saw this huge cardboard box that 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. And 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 eight 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.

• 1:07:10Derek Sivers?

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

• 1:07:54Derek Sivers?

  seem to be the tool we use to make the most of our time. But that doesn't always make sense, does it? Because like, as you go through life, you keep getting new information moment to moment. That helps you make the best decision for that moment. Not what you thought would be the best decision earlier when you made a plan, which was a prediction. I think about like, 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.

• 1:08:25Tim Ferriss?

  I would never guess based on your assertion of matching plateware.

• 1:08:31Derek Sivers?

  How much energy I've clearly put into this house and making it perfect with all of its decor.

• 1:08:37Tim Ferriss?

  There's nothing on the walls and no furniture.

• 1:08:40Derek Sivers?

  Yeah.

• 1:08:41Tim Ferriss?

  Except for some mice.

• 1:08:43Derek Sivers?

  Yeah.

• 1:08:45Tim Ferriss?

  Legitimately.

• 1:08:46Derek Sivers?

  Yeah, I have three pet mice. We were gonna bring them out. It'd 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 like 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 gonna put down the deposit. It was gonna be mine. I fell asleep that night thinking, at first thought, I was thinking, I'm gonna be so happy tomorrow. And then I thought, wait, I'm already happy. What, am I gonna 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.

• 1:09:32Derek Sivers?

  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. Our 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.

• 1:10:15Tim Ferriss?

  It's a great book.

• 1:10:16Derek Sivers?

  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.

• 1:10:25Tim Ferriss?

  I had no idea you were gonna bring this up. This is great.

• 1:10:27Derek Sivers?

  Yeah.

• 1:10:28Tim Ferriss?

  Yeah.

• 1:10:29Derek Sivers?

  That maximizers have been found to feel worse about the decisions they make. They 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 that lesson to heart and have shaped my life around it.

• 1:11:07Tim Ferriss?

  So, just for definition terms, right? Because people might think optimizing is trying to eke out the every last iota of improvement, right? But I think what we're really talking about is-

• 1:11:18Derek Sivers?

  Sorry to interrupt. You know what? Like, if you were to hear Paul McCartney go, "Hey Jude," you'd be like, "Whoa." Just to hear him sing two notes.

• 1:11:25Tim Ferriss?

  Yeah.

• 1:11:26Derek Sivers?

  To hear you go, "Optimizing."

• 1:11:29Tim Ferriss?

  That's like, whoa.

• 1:11:33Derek Sivers?

  That's classic.

• 1:11:34Tim Ferriss?

  It's classic, you know?

• 1:11:37Tim Ferriss?

  You know, if that is my legacy, so be it.

• 1:11:40Derek Sivers?

  Optimizing.

• 1:11:40Tim Ferriss?

  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? Maybe 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. And

• 1:12:20Tim Ferriss?

  one of my most effective friends basically has said, I'm paraphrasing, but he's like, "Yeah, I optimized for like one or two things and everything else is good enough. Like I just, I just have to get it to good enough."

• 1:12:31Derek Sivers?

  Nice.

• 1:12:31Tim Ferriss?

  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. So how do you think about then where you might maximize versus where you satisfice? Or is it, because I know it's not good enough across the board. I find that hard to believe.

• 1:12:58Derek Sivers?

  What do I maximize? I'm not sure.

• 1:13:00Tim Ferriss?

  Or maybe maximize is too polarizing a word.

• 1:13:05Derek Sivers?

  No, you know what I think it is?

• 1:13:06Tim Ferriss?

  Yeah.

• 1:13:07Derek Sivers?

  If it's really fun.

• 1:13:08Tim Ferriss?

  Okay.

• 1:13:09Derek Sivers?

  If you think it's just actually really fun to like, maybe some people set up their, 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.

• 1:13:24Tim Ferriss?

  Yeah.

• 1:13:24Derek Sivers?

  And they nerd out and they know it's stupid, usually.

• 1:13:27Tim Ferriss?

  Yeah.

• 1:13:29Derek Sivers?

  They're just like, I don't care. I want this thing with the gold plated cable connector.

• 1:13:33Tim Ferriss?

  Right.

• 1:13:34Derek Sivers?

  And I think if you have fun optimizing, then it's worth it. If maximizing that is, if the process is fun to you.

• 1:13:42Tim Ferriss?

  Mm hmm.

• 1:13:43Derek Sivers?

  I think that should be the parameter. But I think that saying enough, good enough, is a superpower.

• 1:13:48Tim Ferriss?

  Yeah, I really do. I really agree with that.

• 1:13:51Derek Sivers?

  You know what is such a good lesson to learn is that nobody cares what you're not good at.

• 1:13:57Tim Ferriss?

  Okay, say more.

• 1:13:58Derek Sivers?

  Like publicly, you're gonna be just known for a few things that you're good at.

• 1:14:02Tim Ferriss?

  Yeah.

• 1:14:02Derek Sivers?

  All those things that you're not good at, nobody cares that you're not good at them. So just let it go, like, you know?

• 1:14:09Tim Ferriss?

  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.

• 1:14:21Tim Ferriss?

  There is that.

• 1:14:25Tim Ferriss?

  I mean, not, yeah, not that I'm recently single and thinking about, and thinking about this all the time or anything.

• 1:14:30Derek Sivers?

  We have spent many hours talking about sex while walking in the forests of New Zealand. Sex and relationships and...

• 1:14:38Tim Ferriss?

  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?

• 1:14:50Derek Sivers?

  I haven't had a shower since yesterday. I was feeling greasy. It was 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.

• 1:15:01Tim Ferriss?

  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. Right? If it can be undone easily, this is also with money, right? Attention and money. I'm gonna default to speed with a lot of things. If it's not that important or if it's pretty easy to reverse.

• 1:15:45Tim Ferriss?

  I think that's been helpful.

• 1:15:47Derek Sivers?

  Off the top of my head, I think how important it is to be... Done with something so that you can move on.

• 1:15:54Tim Ferriss?

  Mm hmm.

• 1:15:55Derek Sivers?

  Like, I don't want.

• 1:15:57Tim Ferriss?

  Open loops.

• 1:15:57Derek Sivers?

  Yeah. Unresolved decisions, sitting unresolved, sitting undecided for a long time.

• 1:16:03Tim Ferriss?

  Yep.

• 1:16:04Derek Sivers?

  I feel the weight of those unfinished projects.

• 1:16:07Tim Ferriss?

  Mm hmm.

• 1:16:08Derek Sivers?

  Because I'm trying to make it perfect.

• 1:16:09Tim Ferriss?

  Yep.

• 1:16:10Derek Sivers?

  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. You know, at some point. I love the fact that we say we, somebody releases an album. You release a book because there's a wonderful double meaning in that word, right? Like, all right.

• 1:16:28Tim Ferriss?

  I've never even thought about that.

• 1:16:29Derek Sivers?

  Released.

• 1:16:30Tim Ferriss?

  Yeah, I like that.

• 1:16:31Derek Sivers?

  So I think about that with anything I post on my site, any of my books. It's like, all right, it's released. It's good enough.

• 1:16:36Tim Ferriss?

  Hmm. All right. I'm going to combine this, maybe another Siversism. It's not really Siversism, 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?

• 1:16:57Derek Sivers?

  All right. So again, I'm addressing the audience for a second. So, you know, I figure I'm coming on the podcast. This isn't just one of our random conversations.

• 1:17:08Tim Ferriss?

  Yeah.

• 1:17:08Derek Sivers?

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

• 1:17:12Tim Ferriss?

  Yep.

• 1:17:12Derek Sivers?

  We can talk freely without hitting record.

• 1:17:14Tim Ferriss?

  Mm hmm.

• 1:17:15Derek Sivers?

  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? A 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. It'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 coming away?

• 1:18:00Derek Sivers?

  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.

• 1:18:20Tim Ferriss?

  Preach.

• 1:18:21Derek Sivers?

  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. So, 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.

• 1:19:06Derek Sivers?

  Here'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.

• 1:19:34Tim Ferriss?

  You've come up with so many children's books ideas in this conversation.

• 1:19:38Derek Sivers?

  The cat and the alien.

• 1:19:39Tim Ferriss?

  The cat, the alien, and the octopus.

• 1:19:40Derek Sivers?

  Because it makes you realize that everything else is just mental interpretation, right? Like, there we go. This is on the table. This is true. But everything else, including, what was this one? Am I flipping you off right now? Like, am I angry at you right now? No, just because I'm-

• 1:19:56Tim Ferriss?

  He's giving me the middle finger.

• 1:19:58Derek Sivers?

  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. If 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.

• 1:20:42Derek Sivers?

  So they want their kids to believe that family is everything. But they have a self-serving reason to believe that.

• 1:20:46Tim Ferriss?

  Yeah, possibly subconscious, right?

• 1:20:48Derek Sivers?

  Right, right. Oh, so I'm so glad you said this. Have you heard about the split-brain stories that people-

• 1:20:54Tim Ferriss?

  Yes.

• 1:20:54Derek Sivers?

  Okay.

• 1:20:55Tim Ferriss?

  Why did you get up to have a glass of water? That type of stuff?

• 1:20:58Derek Sivers?

  Can I tell it?

• 1:20:58Tim Ferriss?

  Yeah, please.

• 1:20:59Derek Sivers?

  So, this is so important to understand that-

• 1:21:05Tim Ferriss?

  These are crazy. These are so bananas.

• 1:21:07Derek Sivers?

  Actually, we'll start with the other one, since you know that one.

• 1:21:09Tim Ferriss?

  Well, no, no, but the audience doesn't come up-

• 1:21:11Derek Sivers?

  No, no, no, but we'll do both. But during brain surgery, the patient needs to stay awake. And so there was a woman-

• 1:21:18Tim Ferriss?

  In some, yeah. Or I guess they could, yeah.

• 1:21:20Derek Sivers?

  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. The 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 them-

• 1:21:44Tim Ferriss?

  Stimulating part of the brain.

• 1:21:45Derek Sivers?

  And so, the split-brain patients, there are 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 and 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.

• 1:22:10Tim Ferriss?

  Yeah.

• 1:22:11Derek Sivers?

  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 that 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.

• 1:22:29Tim Ferriss?

  Yeah.

• 1:22:30Derek Sivers?

  So 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? Before there was Virgin Airlines, you've heard the tale that he was at a,

• 1:23:15Derek Sivers?

  an airport and a flight to somewhere was canceled.

• 1:23:17Tim Ferriss?

  Right, it was delayed and...

• 1:23:18Derek Sivers?

  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?

• 1:23:35Tim Ferriss?

  The genesis.

• 1:23:36Derek Sivers?

  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.

• 1:23:47Tim Ferriss?

  Or not evidence-based, right?

• 1:23:50Derek Sivers?

  Not true. Sorry, I'm just, I'm just...

• 1:23:53Tim Ferriss?

  Yeah.

• 1:23:53Derek Sivers?

  Having fun.

• 1:23:55Tim Ferriss?

  Have fun.

• 1:23:55Derek Sivers?

  Because, yeah, not evidence-based. Because we don't say, "I believe in potatoes." Because

• 1:24:03Tim Ferriss?

  Speak for yourself.

• 1:24:03Derek Sivers?

  We don't have to, because there's a potato.

• 1:24:06Tim Ferriss?

  Yeah.

• 1:24:08Derek Sivers?

  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.

• 1:24:16Tim Ferriss?

  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,

• 1:24:28Derek Sivers?

  Ooh.

• 1:24:29Tim Ferriss?

  It's like, ooh, thou doth protest too much.

• 1:24:31Derek Sivers?

  I like that. So, since no beliefs are true,

• 1:24:37Derek Sivers?

  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. This is like, this 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, you know, 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

• 1:25:04Tim Ferriss?

  Mm-hmm.

• 1:25:04Derek Sivers?

  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 Work Week, giving so many wonderful examples of how you don't have to accept the world's norms.

• 1:25:21Tim Ferriss?

  Yep, for sure.

• 1:25:23Derek Sivers?

  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.

• 1:25:34Tim Ferriss?

  Mm-hmm.

• 1:25:34Derek Sivers?

  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,

• 1:25:51Tim Ferriss?

  Mm-hmm.

• 1:25:52Derek Sivers?

  because you realize you can make up the rules. So this is that Matrix moment, where the bullets are flying out, and he goes, wait a minute, this is just code.

• 1:26:00Tim Ferriss?

  Yeah.

• 1:26:01Derek Sivers?

  Somebody 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.

• 1:26:19Tim Ferriss?

  This, I think, begs a number of questions, living in a broader society, about morally acceptable or reprehensible behavior.

• 1:26:29Derek Sivers?

  Right. But that's when I talk about like, being who you want to be.

• 1:26:34Derek Sivers?

  We can't really address people who want to be psychopaths or who want to be damaging.

• 1:26:38Tim Ferriss?

  Yeah.

• 1:26:38Derek Sivers?

  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?

• 1:26:45Tim Ferriss?

  Yeah.

• 1:26:45Derek Sivers?

  How 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, you know, your psychosis that might lead you to be a bad person.

• 1:26:56Tim Ferriss?

  Right. Table that for a minute.

• 1:26:58Derek Sivers?

  So I have a funny little story that felt almost too risque to tell.

• 1:27:02Tim Ferriss?

  I love, I love too risque. Let's do it. Why you don't record these in front of a crowd? Can always edit.

• 1:27:09Derek Sivers?

  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.

• 1:27:29Tim Ferriss?

  Hmm.

• 1:27:30Derek Sivers?

  It's funny, I was like, can I say this on the?

• 1:27:32Tim Ferriss?

  We did not consummate our attraction.

• 1:27:36Derek Sivers?

  Yeah, all right, I'm just gonna say it.

• 1:27:38Tim Ferriss?

  Yeah.

• 1:27:38Derek Sivers?

  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 a.m. Like, time to check out, time to go. And like, and she was asking them in Norwegian, like, please, one more hour. And 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, like, you know, Sheraton, Hilton, Marriott. And it was 11 o'clock and my fairy was leaving at 4 o'clock.

• 1:28:17Tim Ferriss?

  Hmm.

• 1:28:18Derek Sivers?

  Oh, and there's one detail. She was just in the process of breaking up with her fiance.

• 1:28:23Tim Ferriss?

  Oh, yeah, small detail.

• 1:28:26Derek Sivers?

  So this matters because I said, hey, what do you think about getting a hotel for a few hours? She was like, oh. Well, we could. I was like, yeah, it feels kind of naughty, doesn't it? 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,

• 1:28:54Derek Sivers?

  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's like, welcome to the Sheraton Hotel, you know? And 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, 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 okay? Was there any problem? I said, no, no problem at all. Everything's great, just decided to catch an earlier ferry.

• 1:29:39Derek Sivers?

  So paying in full, here it is. He's, 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 stupid establishment. This is not, this is a various reputable hotel. I do not like this. No, you must not. Dude, I don't like this one bit. He was getting really angry. Yeah. And I was so happy because, not for the obvious, but like, it was so liberating realizing that I've done nothing wrong.

• 1:30:23Derek Sivers?

  Nobody was hurt. This is fully like consensual. He's, you know, they were paid for their room. And

• 1:30:30Derek Sivers?

  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. And at a certain point, you realize that you're free, you're liberated from that. 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 point in my life, realizing that I was liberated from authority and from judgment.

• 1:31:07Tim Ferriss?

  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." And 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 fiancee, though, I want to stand in for some of the audience who will say, "Well, wait a second.

• 1:31:52Tim Ferriss?

  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." I'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?"

• 1:32:11Derek Sivers?

  They had broken up but were still living together because she just hadn't kicked out yet.

• 1:32:16Tim Ferriss?

  Ah, okay. All right. Okay.

• 1:32:19Derek Sivers?

  I wouldn't sleep with somebody's wife.

• 1:32:20Tim Ferriss?

  Okay, okay.

• 1:32:21Derek Sivers?

  Or fiancee.

• 1:32:22Tim Ferriss?

  Okay, got it.

• 1:32:23Derek Sivers?

  But no, I know what you mean, that it's... 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. These different ideas of 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.

• 1:32:54Tim Ferriss?

  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, therefore 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.

• 1:33:20Derek Sivers?

  Yeah.

• 1:33:21Tim Ferriss?

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

• 1:33:37Derek Sivers?

  I defer to Sam Harris.

• 1:33:39Tim Ferriss?

  Okay.

• 1:33:40Derek Sivers?

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

• 1:33:43Tim Ferriss?

  I don't think we've discussed it explicitly. So why don't, why don't you, if you wouldn't mind elaborating?

• 1:33:48Derek Sivers?

  Probably the best elaboration is to tell people to go search for Sam Harris Moral Landscape. The 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 and.

• 1:34:10Tim Ferriss?

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

• 1:34:13Derek Sivers?

  Yeah.

• 1:34:15Tim Ferriss?

  Yeah, I don't want to speak, I don't want to speak for Sam.

• 1:34:17Derek Sivers?

  Go find that talk.

• 1:34:18Tim Ferriss?

  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. And that is why sometimes I'm actually very envious of people who are deeply religious. It's like, here are the rules, right? I mean, you want to talk about paradox of choice, like how much decision fatigue does that really mean? I'm actually very envious of that sometimes. So how do you think about, I'm not saying you should think about it, I'm just curious,

• 1:35:01Tim Ferriss?

  when, let's just say, outside of breaking the law? You can do anything, right? There is a, it's just like having 1,500 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? In secular societies, I think about, I wonder about this a lot.

• 1:35:29Derek Sivers?

  Yeah. I recently read a book I can recommend for anybody called What Everyone Should Know About Islam.

• 1:35:34Tim Ferriss?

  Okay.

• 1:35:35Derek Sivers?

  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, the government laws are aligned with the religious laws, which are aligned, like everybody here agrees in this code. It's not a, 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.

• 1:36:17Tim Ferriss?

  Yeah. Yeah. And this is just for people who, this came up very organically in our conversation.

• 1:36:23Derek Sivers?

  I don't remember how, do you?

• 1:36:24Tim Ferriss?

  Yes, I do remember because I think I was talking about how I do not identify as a philanthropist, even though I do a lot of nonprofit work, because I actually have a pretty Hobbesian view of human nature in general and think we've probably, was 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, fill is something the etymology of that. And then the philanthropy is like the anthropocene or anthropology. It's humans. So like to love humans basically is philanthropy. And I don't feel like I

• 1:37:08Tim Ferriss?

  align with that. I'm actually a misanth- 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 Sci-Sci 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. I think that is sort of the stream of conversation that led to that coming up.

• 1:37:48Tim Ferriss?

  I was asking about how you consider constraining your choices with maybe a lens of morality. And so you were going to say.

• 1:37:56Derek Sivers?

  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.

• 1:38:07Tim Ferriss?

  Yep.

• 1:38:08Derek Sivers?

  To say, um, 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.

• 1:38:21Tim Ferriss?

  Hmm.

• 1:38:22Derek Sivers?

  It's like, I don't need to have some million dollar thing to make me happy. I'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 standing declaring themselves to be a stoic.

• 1:39:05Tim Ferriss?

  Or religion, or CrossFit, or veganism, whatever.

• 1:39:08Derek Sivers?

  Right, right. The biggest fault, I think, to.

• 1:39:13Tim Ferriss?

  Crypto for that matter. You went on about religion.

• 1:39:15Derek Sivers?

  Yeah. It's a tribalism in that case.

• 1:39:18Tim Ferriss?

  Yeah, not for, not for everyone, just to be clear, but yeah.

• 1:39:20Derek Sivers?

  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 nine, I was on a plane from Amsterdam to the US and I saw a guy reading Four Hour Work Week. I said, hey, great book. And he goes, it's trash, man. And I said, really? And he goes, yeah, this guy's full of himself. This book is trash. And.

• 1:39:50Derek Sivers?

  And I think about that all the time because

• 1:39:52Tim Ferriss?

  This is like, was he a German guy?

• 1:39:54Derek Sivers?

  No, I don't know.

• 1:39:55Tim Ferriss?

  I think, I think, yeah, I've heard a bit of this before.

• 1:39:57Derek Sivers?

  So it's like, because he found one thing

• 1:40:01Tim Ferriss?

  Not to slight the fine Germans, outside of the US, Germany and Korea are my besties.

• 1:40:06Derek Sivers?

  But he found one thing he didn't like about you.

• 1:40:09Tim Ferriss?

  Yeah.

• 1:40:09Derek Sivers?

  And therefore declared all 400 pages of this book to be trash.

• 1:40:14Tim Ferriss?

  Right.

• 1:40:14Derek Sivers?

  And I think that's the problem with isms. Is that if you're trying to buy into

• 1:40:19Tim Ferriss?

  All or nothing.

• 1:40:20Derek Sivers?

  A system, yeah, 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, you know? 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.

• 1:40:37Tim Ferriss?

  That's page four to seven in your Dr. Seuss.

• 1:40:39Derek Sivers?

  Right. Oh, yeah, we're back to that.

• 1:40:42Tim Ferriss?

  The cat, the alien and the octopus.

• 1:40:43Derek Sivers?

  But it's, it's like the mindset that wants everything to be a religion.

• 1:40:47Tim Ferriss?

  Yeah.

• 1:40:48Derek Sivers?

  You know, and I think that's deeply built into people.

• 1:40:50Tim Ferriss?

  Yeah, yeah, the reductionism. I mean, it simplifies reality.

• 1:40:53Derek Sivers?

  Yeah. Simplifies reality. I like that.

• 1:40:56Tim Ferriss?

  I mean, you do assume cognitive burden to take the harder path.

• 1:40:59Derek Sivers?

  So on that note, back to my whole like useful, not true, my radical, what did I call it? Radical doubt, super skepticism?

• 1:41:07Tim Ferriss?

  Yes.

• 1:41:07Derek Sivers?

  I think we should be skeptical of every ism. I think we should avoid isms, avoid ideology and take ideas piecemeal.

• 1:41:17Tim Ferriss?

  Yeah.

• 1:41:17Derek Sivers?

  Which 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.

• 1:41:44Tim Ferriss?

  Yeah.

• 1:41:44Derek Sivers?

  I subscribed to this ism. That to me seems to be a, a jumping to a conclusion. It's, it's a punt. It's like just deferring to the ism.

• 1:41:52Tim Ferriss?

  Yeah. 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, right? Like, are you a Democrat or a Republican? Oh, 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.

• 1:42:13Derek Sivers?

  Yes.

• 1:42:14Tim Ferriss?

  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 a counter 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 that 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

• 1:42:59Tim Ferriss?

  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 gonna be like, wait a second, this guy can't be any happier. What kind of alien is this guy? How much of that do you think is out of the box? Just your code versus a cultivated?

• 1:43:29Derek Sivers?

  Do you know Sonia Lembursky?

• 1:43:30Tim Ferriss?

  No.

• 1:43:31Derek Sivers?

  Okay. You know who she is?

• 1:43:32Tim Ferriss?

  Nope.

• 1:43:32Derek Sivers?

  Oh, she wrote one of those books on happiness. After I read stumbling on happiness, I went, ooh, that was good.

• 1:43:39Tim Ferriss?

  That was a good book.

• 1:43:40Derek Sivers?

  And I went to go find other books on the subject. So she wrote a couple of books on happiness. She's been studying happiness for decades.

• 1:43:46Tim Ferriss?

  Sonia Lembowski?

• 1:43:47Derek Sivers?

  Lembursky, I think.

• 1:43:48Tim Ferriss?

  Lembursky. I'll find it. Put in the show notes.

• 1:43:51Derek Sivers?

  Show notes. 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. And the other 50% is in their control. So the best we can do is just control that 50%. And so, yeah, I think.

• 1:44:04Tim Ferriss?

  Sounds like you're stoic. Closet stuff.

• 1:44:07Derek Sivers?

  Oh, I am.

• 1:44:09Derek Sivers?

  Minus the ism.

• 1:44:10Tim Ferriss?

  Yeah, right.

• 1:44:11Derek Sivers?

  But did I ever tell you about that, that you even talked about Stoicism a bit? And I was like, ancient crap.

• 1:44:18Derek Sivers?

  And then finally, in 2010, I read A Guide to the Good Life.

• 1:44:22Tim Ferriss?

  William Irvine, I think.

• 1:44:24Derek Sivers?

  Yes. I read it, and I went, 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. Maybe, I suspect, I found out years later that the Dale Carnegie book called How to Stop Worrying and Start Living.

• 1:44:43Tim Ferriss?

  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.

• 1:45:02Derek Sivers?

  I just read a couple of years ago in Wikipedia or something that that book was basically spouting Stoic values.

• 1:45:11Tim Ferriss?

  Makes perfect sense. It's a great book, by the way, folks. How to Stop Worrying and Start Living.

• 1:45:16Derek Sivers?

  By Dale Carnegie. 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. This was my weird approach to life. But then just two years ago, I saw that Wikipedia entry about.

• 1:45:39Tim Ferriss?

  You got incepted by Dale Carnegie.

• 1:45:41Derek Sivers?

  Oh, wow. Yeah, inception, yeah, like.

• 1:45:42Tim Ferriss?

  Wow.

• 1:45:43Derek Sivers?

  So, but point is, I've been thinking that way since I was a teenager. And it wasn't until the age of like 40 that I read an actual book on Stoicism. Whoa, this is really like, 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.

• 1:46:03Tim Ferriss?

  Yep.

• 1:46:04Derek Sivers?

  And if you find yourself blindly kind of saying, all of this, this is me, this is how I'm going to live now.

• 1:46:08Tim Ferriss?

  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.

• 1:46:20Derek Sivers?

  Right, right.

• 1:46:21Tim Ferriss?

  To see what happens, but not like this is the truth in all caps. This is who I am, identity.

• 1:46:29Derek Sivers?

  That's totally different. See, that's pluralism versus monism. Like the monism 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?

• 1:47:05Tim Ferriss?

  Yeah, so this researcher who wrote the book After Stumbling on Happiness said 50/50. And then I dragged us into stosis.

• 1:47:11Derek Sivers?

  So that's it. 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.

• 1:47:38Tim Ferriss?

  Your own beliefs.

• 1:47:39Derek Sivers?

  Yeah, my own, something I've said that 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. I'll just keep it general like that. Then I'll stop and ask myself like, wait a minute, is that true? Like, 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.

• 1:48:03Tim Ferriss?

  And you do this in writing?

• 1:48:04Derek Sivers?

  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.

• 1:48:22Tim Ferriss?

  Also, in the all roads lead to Rome type of metaphor, CBT, as I understand it, largely based on many Stoic writings.

• 1:48:32Derek Sivers?

  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 like 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."

• 1:48:51Tim Ferriss?

  Right.

• 1:48:52Derek Sivers?

  You said, like, how would you recommend somebody do that? Or how do you do it?

• 1:48:55Tim Ferriss?

  Yeah, how do you translate that into durable behavioral change? Right, 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." It's one thing to achieve that and quite a different thing to implement that latter belief in a way that changes your behavior.

• 1:49:15Derek Sivers?

  So I think the, um, you 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? So you could just kind of stack up evidence. And then I find that, you know, 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

• 1:50:00Derek Sivers?

  you want to have, saying, "You know, that's a good point. My friend Tracy such and such at 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. Like, you know, some crazy things I've done in my life to

• 1:50:20Tim Ferriss?

  I do.

• 1:50:21Derek Sivers?

  Cut off some options in my life as a giant leap. We can talk about that if you want. But small actions are big actions. You can take the action before necessarily internalizing it.

• 1:50:33Tim Ferriss?

  Totally. Kind of fake it before you make it.

• 1:50:34Derek Sivers?

  Fake it before you make it, yes. Even if you decide, like-

• 1:50:36Tim Ferriss?

  Do it before you believe it.

• 1:50:37Derek Sivers?

  Right.

• 1:50:38Tim Ferriss?

  Act as if-

• 1:50:39Derek Sivers?

  "I should sign up for college." And you're just like, "You're right, I should. Oh, my God, I just did." Like, even before you've convinced yourself, you can, like, sign up that little form and take that first step to

• 1:50:49Tim Ferriss?

  Yeah.

• 1:50:49Derek Sivers?

  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. And then we all have the desire to be congruent with the actions we've taken.

• 1:51:00Tim Ferriss?

  Mm hmm.

• 1:51:00Derek Sivers?

  So it's like, oh, look, I'm this kind of person now. This is my belief now.

• 1:51:03Tim Ferriss?

  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.

• 1:51:18Derek Sivers?

  Oh, yeah.

• 1:51:18Tim Ferriss?

  Which is very much this, and I found personally very useful, super, super useful. You teased, 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 I make for a story?

• 1:51:37Derek Sivers?

  Is there?

• 1:51:40Derek Sivers?

  Yeah, I renounced my US citizenship in 2011.

• 1:51:46Tim Ferriss?

  That's a big one.

• 1:51:47Derek Sivers?

  As a way of, I deliberately burned the ships.

• 1:51:52Tim Ferriss?

  Yeah.

• 1:51:52Derek Sivers?

  So I have to explain this metaphor because I found that most people haven't heard this tale. But we have all heard of burning the bridges.

• 1:51:58Tim Ferriss?

  Mm hmm.

• 1:51:59Derek Sivers?

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

• 1:52:28Tim Ferriss?

  Mm hmm.

• 1:52:28Derek Sivers?

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

• 1:52:34Tim Ferriss?

  Mm hmm.

• 1:52:34Derek Sivers?

  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.

• 1:52:53Tim Ferriss?

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

• 1:53:05Derek Sivers?

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

• 1:53:09Tim Ferriss?

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

• 1:53:12Derek Sivers?

  I highly recommend when everybody asks me about it. Some people have found out about this.

• 1:53:18Tim Ferriss?

  No, no, handful, handful moral, no.

• 1:53:22Derek Sivers?

  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.

• 1:53:38Tim Ferriss?

  Yep.

• 1:53:38Derek Sivers?

  I love that. And under that wise advice, I think that no, you should not renounce your US 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 US sourced. So now that all gets taxed at a 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 and we needed to quickly get on a plane that night. But I didn't have visa.

• 1:54:23Derek Sivers?

  So I went to the US 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 visa. Next, you know, and the slip says, you may not reapply. This decision is final. And hey, useful, not true. I challenged that, 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.

• 1:54:46Tim Ferriss?

  Mountain of evidence for what?

• 1:54:48Derek Sivers?

  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. She'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.

• 1:55:12Tim Ferriss?

  You're not a flight risk.

• 1:55:14Derek Sivers?

  Right, not a flight risk. So I went back with a mountain of evidence and a letter from the doctor for my ex's dad saying, you know, please, he only has a few days to live. Please 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.

• 1:55:36Tim Ferriss?

  Not true.

• 1:55:37Derek Sivers?

  Yeah, I always say like, no, no, no. Once, 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.

• 1:55:45Tim Ferriss?

  Yeah, I would say in general, not to pay with too broad a brush, but the US frowns upon people who renounce citizenship.

• 1:55:52Derek Sivers?

  Yeah, I'm always aware that I might.

• 1:55:54Tim Ferriss?

  In a lot of ways.

• 1:55:55Derek Sivers?

  Never be allowed back in ever again.

• 1:55:56Tim Ferriss?

  Yeah. Okay. What is another example of a giant leap? Anything come to mind? And that's a huge one, for sure.

• 1:56:07Derek Sivers?

  Moving.

• 1:56:08Tim Ferriss?

  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.

• 1:56:18Derek Sivers?

  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, no, can't do it.

• 1:56:44Derek Sivers?

  Don't want to, don't have to, can't. And so finally, after 12 years, it came in handy for that. But no, to me, that was, it was a huge thing.

• 1:56:55Tim Ferriss?

  And the other giant leaps?

• 1:56:56Derek Sivers?

  Giant leaps. Selling my company came in like an instant moment of clarity of like, God, life is weird when, when it's like you can hold multiple philosophies in your head 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.

• 1:57:18Derek Sivers?

  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.

• 1:57:25Tim Ferriss?

  Yeah.

• 1:57:25Derek Sivers?

  And make that it. 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. Another 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 a 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 brush stroke 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

• 1:58:10Derek Sivers?

  and get back to work. But 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.

• 1:58:35Tim Ferriss?

  Was there a feeling or a meal or something your friend said that triggered that?

• 1:58:42Derek Sivers?

  He just asked me a bunch of questions, like, he challenged the things I was saying. He 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 pay your taxes. He said, no, Derek, you need to understand this. You don't have to do anything. What's the dude on Power of Now that went and sat on a park bench? Who wrote Power of Now?

• 1:59:12Tim Ferriss?

  Eckhart Tolle.

• 1:59:13Derek Sivers?

  Eckhart Tolle.

• 1:59:13Tim Ferriss?

  Yeah, I never read the book, but I've heard good things about it.

• 1:59:16Derek Sivers?

  I unfortunately tried to listen to it on a long drive and don't do that. It's hazardous. He'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

• 1:59:36Tim Ferriss?

  Consequences.

• 1:59:36Derek Sivers?

  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. You'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.

• 2:00:09Tim Ferriss?

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

• 2:00:31Derek Sivers?

  Pick the brain?

• 2:00:31Tim Ferriss?

  Pick the brain.

• 2:00:32Derek Sivers?

  So appealing.

• 2:00:33Tim Ferriss?

  Have a meal.

• 2:00:34Derek Sivers?

  Who would not want to have their brain picked?

• 2:00:36Tim Ferriss?

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

• 2:00:41Derek Sivers?

  Here's what I do. I have three mentors. So anytime I hit 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?

• 2:00:53Tim Ferriss?

  Right.

• 2:00:53Derek Sivers?

  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. I don't want to send somebody a 20-page-long email. So I have to make this as succinct as possible.

• 2:01:11Tim Ferriss?

  What does that in practice look like? A half-page page?

• 2:01:14Derek Sivers?

  Yeah, half-page. Like bullet points for everything instead of paragraphs, right? As succinct as I can. And then before I send it to them, I try to predict what this person would say.

• 2:01:25Tim Ferriss?

  So each of those three?

• 2:01:26Derek Sivers?

  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.

• 2:01:40Derek Sivers?

  And I address those points that I'm predicting they would say. I'm going to address those in advance, again, to not waste their time.

• 2:01:47Tim Ferriss?

  And when you say address them, what do you mean by that?

• 2:01:49Derek Sivers?

  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.

• 2:01:58Tim Ferriss?

  Here's my follow up.

• 2:01:59Derek Sivers?

  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.

• 2:02:06Tim Ferriss?

  I got it. You have an answer ready for whatever they might come back with.

• 2:02:09Derek Sivers?

  But I include it in the initial summary of the situation. And then, after I've done that whole process, I don't need to bother them 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 to you? So I think that, you're right, I also get a lot of emails from people saying like, I need a mentor. Will you mentor me? How do I find a mentor?

• 2:02:54Derek Sivers?

  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.

• 2:03:08Tim Ferriss?

  Who is, if you're willing to share, the person who doesn't know you exist?

• 2:03:13Derek Sivers?

  It was Tyler Cowen. I just emailed him two weeks ago to say thank you.

• 2:03:20Tim Ferriss?

  Thanks for your years of service.

• 2:03:21Derek Sivers?

  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?

• 2:03:33Tim Ferriss?

  He walks the walk. He's another example of someone who walks the walk.

• 2:03:36Derek Sivers?

  Very much so.

• 2:03:37Tim Ferriss?

  Not as common as you would hope. Yeah.

• 2:03:40Derek Sivers?

  That's it.

• 2:03:41Tim Ferriss?

  There's a third.

• 2:03:41Derek Sivers?

  It's actually changing. I don't know right now.

• 2:03:43Tim Ferriss?

  Keith Richards.

• 2:03:46Derek Sivers?

  Bjork. What would Bjork do?

• 2:03:48Tim Ferriss?

  Chuck E. Cheese.

• 2:03:49Derek Sivers?

  That would be great. You know, that's really useful. If you have a fictional, a fictional person can be your mentor.

• 2:03:57Tim Ferriss?

  Yeah.

• 2:03:57Derek Sivers?

  You know, like, what would, you know, what would Jesus do? Right? Like, people still do that. Like, okay, I'm not sure what to do. What would Jesus do? That's a perfectly good mentor.

• 2:04:07Tim Ferriss?

  Yeah, and.

• 2:04:09Tim Ferriss?

  I think a lot of people would agree with you. And 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 Mullin, because 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

• 2:04:46Tim Ferriss?

  good at perspectival knowledge, taking alternative positions, taking the counter position on his own thoughts, his own opinions, his own goals. So 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. Oh, wow. 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

• 2:05:29Tim Ferriss?

  of me say? And I just write out the dialogue. And by then 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. I do something very similar, I guess, is that's what I'm saying.

• 2:06:03Derek Sivers?

  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.

• 2:06:16Tim Ferriss?

  Yeah, totally.

• 2:06:17Derek Sivers?

  Like just the act of opening their email client and starting with it and going, okay, I want to ask Derek Sivers this thing.

• 2:06:22Tim Ferriss?

  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, even if it's a really close friend. Like I don't, I if 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 a situation. Here are some of my assumptions. Here's what I've already tried.

• 2:06:55Tim Ferriss?

  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 self shame out of here. Like I would like to have fewer than several thousand emails to come in with like,

• 2:07:22Tim Ferriss?

  how can I launch my book? Please tell me.

• 2:07:25Derek Sivers?

  And I'll admit, I actually got oddly shy two minutes ago when you asked me who the third one was. Cause actually it's, it's been you in the past.

• 2:07:30Tim Ferriss?

  No.

• 2:07:31Derek Sivers?

  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, and I'm like, no, hold on.

• 2:07:43Derek Sivers?

  And I'll just do it for someone. Never mind.

• 2:07:44Tim Ferriss?

  Well, thank you for, you know, I think about you, I think about you, Matt. It's funny you mentioned Seth, because Seth would be on a shortlist for me as well of people who really. Think and more than think, it's question.

• 2:08:01Derek Sivers?

  Yeah.

• 2:08:02Tim Ferriss?

  The musts, the shoulds, the have tos. I'm like, wait a fucking second. That's nonsense. You know, I feel like you're very good at that, which is part of the reason I've read your first books many times. No, I'm all shy.

• 2:08:17Derek Sivers?

  Should we?

• 2:08:18Tim Ferriss?

  I feel like we should do two things.

• 2:08:20Derek Sivers?

  Okay.

• 2:08:21Tim Ferriss?

  I feel like we should get a slight refill on the scotch. And then maybe talk about games, the games we play.

• 2:08:31Derek Sivers?

  All right.

• 2:08:31Tim Ferriss?

  Getting good at games, things of this type. So a little, little bathroom and then Scotch break.

• 2:08:39Derek Sivers?

  We're back.

• 2:08:40Tim Ferriss?

  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.

• 2:08:51Derek Sivers?

  Yeah.

• 2:08:51Tim Ferriss?

  Like, 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.

• 2:09:05Derek Sivers?

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

• 2:09:15Tim Ferriss?

  Yeah, you're good at holding both.

• 2:09:16Derek Sivers?

  Looking at you, but I'm thinking of them. No offense.

• 2:09:22Tim Ferriss?

  Wow, we could, we could unpack that for a while.

• 2:09:26Derek Sivers?

  You and your euphemisms. All right.

• 2:09:28Tim Ferriss?

  Dark mirror, here we come. Cheers, man.

• 2:09:31Derek Sivers?

  Cheers.

• 2:09:31Tim Ferriss?

  So nice to see you.

• 2:09:32Derek Sivers?

  Oh, thanks again, Matt. I don't know why we think Matt's there.

• 2:09:37Tim Ferriss?

  Matt's got the, 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, let you talk about how you think about this kind of thing? Playing games. Maybe not the proper tee up, but I'm gonna go with it.

• 2:10:11Derek Sivers?

  No, that's, so it's, it's something that might seem strange about me.

• 2:10:18Derek Sivers?

  That sometimes people say that I seem weird because of the choices I make in life.

• 2:10:24Tim Ferriss?

  You're pretty weird.

• 2:10:25Derek Sivers?

  Thanks, 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, OK, let's go do something else. I won the game, even with, say, addictive video games. So have you ever played Stardew Valley?

• 2:11:10Tim Ferriss?

  No, I probably shouldn't.

• 2:11:12Derek Sivers?

  It's adorably 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.

• 2:11:23Tim Ferriss?

  I think the story behind this game is also very interesting.

• 2:11:26Derek Sivers?

  Made by one guy with a passion for many years.

• 2:11:28Tim Ferriss?

  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.

• 2:11:38Derek Sivers?

  Yeah, I mean, it's so good. I mean, OK, let's say if you want to play a great game.

• 2:11:43Tim Ferriss?

  Yeah.

• 2:11:43Derek Sivers?

  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.

• 2:11:49Tim Ferriss?

  Yeah.

• 2:11:50Derek Sivers?

  You just pay your $9 or something like that upfront and then you've got the game forever.

• 2:11:53Tim Ferriss?

  Yeah, that's cool.

• 2:11:54Derek Sivers?

  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.

• 2:12:12Tim Ferriss?

  Yeah.

• 2:12:12Derek Sivers?

  And at a certain point, she had done everything. She'd 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.

• 2:12:26Tim Ferriss?

  Yeah.

• 2:12:26Derek Sivers?

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

• 2:12:33Tim Ferriss?

  Mm hmm.

• 2:12:34Derek Sivers?

  And 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.

• 2:12:57Tim Ferriss?

  Gautier.

• 2:12:57Derek Sivers?

  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.

• 2:13:05Tim Ferriss?

  Okay.

• 2:13:06Derek Sivers?

  That guy, 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. I don't want to keep singing that song for the rest of my life. There is no more Gautier. So now he's just back to his legal name and he's the drummer and singer in a band called The Basics. 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 reelection, 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.

• 2:13:51Derek Sivers?

  She quit after 27 years and like that was enough. She hit her point that was enough. Cameron Diaz, I suddenly, after watching There's Something About Mary 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.

• 2:14:11Tim Ferriss?

  I should interview her.

• 2:14:12Derek Sivers?

  Yeah.

• 2:14:13Tim Ferriss?

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

• 2:14:18Derek Sivers?

  Yeah.

• 2:14:19Tim Ferriss?

  Yeah.

• 2:14:20Derek Sivers?

  Because?

• 2:14:21Tim Ferriss?

  People are just like, yep, goodbye.

• 2:14:22Derek Sivers?

  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. So I really admire 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.

• 2:14:41Tim Ferriss?

  Yeah.

• 2:14:42Derek Sivers?

  I really admire that she did that. I was super, super influenced by Felix Dennis's book called How to Get Rich.

• 2:14:50Tim Ferriss?

  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.

• 2:15:07Derek Sivers?

  Oh.

• 2:15:07Tim Ferriss?

  But just listen. Anyway, I just want to second-

• 2:15:09Derek Sivers?

  How's it not suitable?

• 2:15:10Tim Ferriss?

  Well, I mean, look, you have a very particular, different orientation on these things, but most parents probably don't want to listen to an audiobook that's like, "Yeah, and then I spent all the money on coke and whores."

• 2:15:22Derek Sivers?

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

• 2:15:27Tim Ferriss?

  It's funny for that reason, right? Because he's so candid-

• 2:15:30Derek Sivers?

  Yeah.

• 2:15:30Tim Ferriss?

  -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.

• 2:15:42Derek Sivers?

  I love that book.

• 2:15:43Tim Ferriss?

  Okay, so I interrupted.

• 2:15:44Derek Sivers?

  No, 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, you know, coming into more money than I could ever spend in a lifetime. And just about that time, I read Felix Dennis's 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'd just sold CD Baby, had a ton of money. It's like, what to do now?

• 2:16:29Derek Sivers?

  And I read this book from this filthy rich old man, being entirely honest, and I thought I should just learn from his experience.

• 2:16:38Tim Ferriss?

  Yep.

• 2:16:39Derek Sivers?

  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, but 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. But I think we should all entertain the idea. We could say, I'm really good at this game, so I should stop playing.

• 2:17:12Tim Ferriss?

  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.

• 2:17:48Derek Sivers?

  Wow.

• 2:17:48Tim Ferriss?

  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? Come on the on the top and like kicking like hell underneath. I don't know. But you have a thoughtful, almost serene contentedness almost all the time that I interact with you. That is my perception.

• 2:18:19Derek Sivers?

  That's true.

• 2:18:19Tim Ferriss?

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

• 2:18:30Derek Sivers?

  Yes, that's true.

• 2:18:31Tim Ferriss?

  So that makes it odd, or for me, to hear you say, I want to be famous. Cause I'm like, what do you get out of fame? If that's your constitution? Like it's

• 2:18:40Derek Sivers?

  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.

• 2:18:54Tim Ferriss?

  Yeah.

• 2:18:55Derek Sivers?

  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. And he said, nothing to do with what other people think of you? And I went, other people think? I was like, no, what? And he goes, I think for a lot of people, they would define their success through the eyes of others. I was like, why? Why would anybody? And he said, wait, you seriously have never considered that? I was like, wow.

• 2:19:35Tim Ferriss?

  He's barking up the wrong tree. He's got the wrong guy.

• 2:19:38Derek Sivers?

  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.

• 2:19:51Tim Ferriss?

  Yeah. So how does fame fit into that?

• 2:19:53Derek Sivers?

  I 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.

• 2:20:12Tim Ferriss?

  Incredible musician.

• 2:20:13Derek Sivers?

  Yeah. I didn't want to be that famous, but like, I don't know, Brian Eno?

• 2:20:18Tim Ferriss?

  Mm hmm.

• 2:20:19Derek Sivers?

  That's a good fame role model, where it's not like he'd get hounded walking down the street.

• 2:20:23Tim Ferriss?

  And that was driven by a competitive drive.

• 2:20:27Derek Sivers?

  It was more just like, let's see if I can do it.

• 2:20:30Tim Ferriss?

  Okay.

• 2:20:31Derek Sivers?

  You know, just with that spirit of like, I think I can do that. I want to try doing that. And it was also feeling that what I was doing musically was valid and worth hearing. And so a way for people to hear it is to.

• 2:20:45Tim Ferriss?

  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.

• 2:20:52Derek Sivers?

  12 years.

• 2:20:53Tim Ferriss?

  God, it's crazy, because we also interact virtually. So I was describing to someone.

• 2:21:01Tim Ferriss?

  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.

• 2:21:32Derek Sivers?

  Hmm.

• 2:21:33Tim Ferriss?

  Right? Like you are, you're a ringleader in a circus.

• 2:21:36Derek Sivers?

  Right.

• 2:21:38Tim Ferriss?

  Musician, you're really good at imitation voices, et cetera. 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.

• 2:22:19Derek Sivers?

  Maybe it is because I just had that life shift where it's like I did it to a certain point. I didn't get as famous as I thought I could, but I was successful enough. Like I bought my house in Woodstock with the money I made touring. 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 flipped something in my head where it's like, I no longer need the attention for me. I don't need any more attention. I don't need any more validation. And now I don't even need any more money. I don't really don't need anything from anybody. But yeah, you're right. I still am socially skilled. I know how to get on stage and talk.

• 2:23:04Tim Ferriss?

  Yeah, good at it, really good at it. You're a combination of elements that I don't usually see together. It's very rare.

• 2:23:11Derek Sivers?

  Am I blushing?

• 2:23:12Tim Ferriss?

  You're blushing. Could be the scotch.

• 2:23:17Tim Ferriss?

  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. There are people, however, who, let's just say they want to be a grand master in chess, like, this is my game.

• 2:23:54Tim Ferriss?

  I win. That is a win on the road of additional wins and mastery to strive to become the best in the world. Or it'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.

• 2:24:38Tim Ferriss?

  They don't have the same love perhaps they once did for that game, but they continue to play it because subconsciously or consciously, they do not know what else to do. 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?

• 2:24:55Derek Sivers?

  Oh, wow. Okay. The subquestions. We are reversing back to the.

• 2:24:58Tim Ferriss?

  Yeah, this is a whole.

• 2:24:59Derek Sivers?

  Okay, so the.

• 2:25:01Tim Ferriss?

  Series of things wrapped in one.

• 2:25:03Derek Sivers?

  In fact, if you don't mind, I'm gonna, I think I might end up.

• 2:25:05Tim Ferriss?

  Let's do it in reverse.

• 2:25:06Derek Sivers?

  Whatever order they. So the, the third category of people that don't know what else they can do, that's the category that by my values, I want to like physically pick them up and put them into a different scenario. I think it's just objectively, you need to change now. You need to shake it up in order to live a full life.

• 2:25:25Tim Ferriss?

  Yep.

• 2:25:26Derek Sivers?

  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.

• 2:25:39Tim Ferriss?

  Just because it's not true doesn't mean it isn't valuable.

• 2:25:41Derek Sivers?

  Right. It's useful.

• 2:25:42Tim Ferriss?

  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.

• 2:25:53Derek Sivers?

  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 like, I wasn't eagerly awaiting George Harrison's next album, you know? 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.

• 2:26:38Derek Sivers?

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

• 2:26:46Tim Ferriss?

  Or like you're good enough, go to an ashram for two years, you can always come back, you'll be fine.

• 2:26:50Derek Sivers?

  But just imagine the joy of, God, sometimes even a simple manual labor, what is 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, whatever, assigned him to just be a gardener now. And he kind of found his peace with it. And 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.

• 2:27:25Tim Ferriss?

  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, The Making of the Modern World.

• 2:27:42Derek Sivers?

  Great book, yeah.

• 2:27:43Tim Ferriss?

  Yeah, really good, especially the first half or so is really exceptional. But I realized, because they mentioned Alexander and the grain in that book, I realized. Alexander. It's kind of like Madonna. It's got one name. I don't know that dude's last name. Do you? And like I've polled 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 of 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.

• 2:28:22Derek Sivers?

  Okay, wait, there was some sub questions in that last one.

• 2:28:25Tim Ferriss?

  I can rewind, which by the way is totally developed skill. That's not something, this is after doing a lot of podcasts.

• 2:28:30Derek Sivers?

  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?

• 2:28:43Tim Ferriss?

  Yeah, totally trained. Yeah, which is wild. So I was asking you maximizer versus being satisfizer. Have you ever been a maximizer?

• 2:28:52Derek Sivers?

  Yeah. So just like, I think you can't preach minimalism to somebody who hasn't felt the pain of having too much stuff.

• 2:29:01Tim Ferriss?

  Yep.

• 2:29:01Derek Sivers?

  They 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. And I think satisficing 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 I need to learn how to say good enough. And now that I put that into action, it was because of reading Paradox of Choice.

• 2:29:44Derek Sivers?

  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. And so, yeah, 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?

• 2:30:21Tim Ferriss?

  Well, for you it was, right? Minimizing regret.

• 2:30:24Derek Sivers?

  Yeah.

• 2:30:25Tim Ferriss?

  Two hours.

• 2:30:26Derek Sivers?

  And kind of like the, I don't know who the hyper effective person is, you mentioned earlier, but choosing that there are just a couple of 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.

• 2:30:41Tim Ferriss?

  So I'll, I'll tell you, I don't think you in mind. So 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.

• 2:30:49Derek Sivers?

  Yeah.

• 2:30:50Tim Ferriss?

  And then the rest.

• 2:30:52Derek Sivers?

  Right. Because he's so intense about those couple of things.

• 2:30:54Tim Ferriss?

  Enough. Yeah. I mean, you have to, right? It's a, he's another one who walks the walk in a big way.

• 2:30:59Derek Sivers?

  Right.

• 2:30:59Tim Ferriss?

  Yeah.

• 2:31:00Derek Sivers?

  So I.

• 2:31:00Tim Ferriss?

  Have you met Josh?

• 2:31:01Derek Sivers?

  No, he's a.

• 2:31:02Tim Ferriss?

  You guys would hit it off.

• 2:31:04Derek Sivers?

  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?

• 2:31:20Tim Ferriss?

  Yeah. I mean, no social, doesn't read email. There are so many conventions that he books. It's really inspiring.

• 2:31:29Derek Sivers?

  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.

• 2:31:38Tim Ferriss?

  Good enough.

• 2:31:41Derek Sivers?

  But have I always been like this? No, I think I had to feel the pain.

• 2:31:43Tim Ferriss?

  What did you use to maximize at any point?

• 2:31:47Derek Sivers?

  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.

• 2:32:08Tim Ferriss?

  It's too much.

• 2:32:08Derek Sivers?

  It was a complete blank slate with no restrictions at all. I wasn't even in a relationship. I was just completely unbound. And so I spent far too long in my diary, thinking of every possible place on earth I might live and why I could. Or I spent hours reading about places that I still haven't even visited. But I learned all about them. I even know what it takes to move there. You know, the naturalization law of becoming a citizen there and the steps to becoming a resident there and the pros and cons of living there. And I've read books about it. Still haven't been there because I did that for many countries. So that's something that was like 10 years ago. I was still maximizing that.

• 2:32:43Tim Ferriss?

  Hmm.

• 2:32:43Derek Sivers?

  And now here we are in New Zealand, where it's 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.

• 2:32:51Tim Ferriss?

  Parked up.

• 2:32:52Derek Sivers?

  11 years now.

• 2:32:53Tim Ferriss?

  That's wild.

• 2:32:54Derek Sivers?

  It's good enough.

• 2:32:55Tim Ferriss?

  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, 1%er 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. And it was the extremes inform the mean, but not vice versa. Something along those lines.

• 2:33:37Tim Ferriss?

  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. And 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,

• 2:34:22Tim Ferriss?

  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 and something like location, I think everyone listening can find somewhere. They can find someplace where they're over optimizing in that way.

• 2:34:51Derek Sivers?

  Thanks 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.

• 2:35:03Tim Ferriss?

  Yeah.

• 2:35:04Derek Sivers?

  It's not so much my personal expression as it is me giving back.

• 2:35:09Tim Ferriss?

  Yeah.

• 2:35:09Derek Sivers?

  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.

• 2:35:35Tim Ferriss?

  Yeah.

• 2:35:36Derek Sivers?

  I can hold on to that question. Maybe it's too late.

• 2:35:38Tim Ferriss?

  I don't give a shit. Fire away.

• 2:35:40Derek Sivers?

  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 and I said, uh, women like sex, right?

• 2:35:57Tim Ferriss?

  Forgot about that.

• 2:35:58Derek Sivers?

  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.

• 2:36:19Tim Ferriss?

  Yeah.

• 2:36:19Derek Sivers?

  And it wasn't until my late 40s.

• 2:36:21Tim Ferriss?

  Yeah.

• 2:36:22Derek Sivers?

  That I was like, oh my God, women like sex.

• 2:36:24Tim Ferriss?

  Yeah.

• 2:36:24Derek Sivers?

  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? Well, fuck yeah, that's what I would tell my former self. But that's just me.

• 2:36:38Tim Ferriss?

  Yeah.

• 2:36:39Derek Sivers?

  I don't think that's the question.

• 2:36:40Tim Ferriss?

  The question is, what advice would you give me? Right?

• 2:36:42Derek Sivers?

  You.

• 2:36:43Tim Ferriss?

  No, I'm saying when someone says, what advice would you give your younger self?

• 2:36:46Derek Sivers?

  Right.

• 2:36:47Tim Ferriss?

  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? That's, I think that is the translation.

• 2:36:57Derek Sivers?

  What advice would you give someone who wants to be where you are?

• 2:37:01Tim Ferriss?

  Yeah.

• 2:37:01Derek Sivers?

  But it's not where you are? Like how to get, how do I get where you are?

• 2:37:04Tim Ferriss?

  I think that's what people are generally asking, right? Cause they don't give a shit what you really, what your younger self would do. They, they care about what they would do, rightly so. But the answers are actually very different, if I'm being honest. The answer is 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.

• 2:37:24Derek Sivers?

  Right.

• 2:37:25Tim Ferriss?

  Because in my case, having a history of some very extreme depression and near suicide in college and so on, like my advice would be related to self-preservation.

• 2:37:36Derek Sivers?

  Mm hmm.

• 2:37:37Tim Ferriss?

  And recommending perhaps certain tools like meditation, like consistent, which I had on some level, but I didn't, I think I could have tripled down on consistent exercise, perhaps supervised psychedelic therapies, et cetera, which don't apply to everybody. They just don't. I mean, I, 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.

• 2:38:19Tim Ferriss?

  Number two, I don't understand the assumptions embedded in them wanting X.

• 2:38:25Derek Sivers?

  Mm hmm.

• 2:38:25Tim Ferriss?

  Right? Because if their assumption is.

• 2:38:29Tim Ferriss?

  Let's just say, and you and I have seen this in ourselves and our experience and the experience of many others, like, once I have X amount of money, all my problems just disappear.

• 2:38:39Derek Sivers?

  Right.

• 2:38:40Tim Ferriss?

  Like the vapor of mist hit by the rising sun, like, all my problems just vanish. And that is an incorrect assumption. But if somebody's just asking that at a Q and A at South by Southwest or something, you don't have the time, you don't have the

• 2:38:53Derek Sivers?

  Right.

• 2:38:53Tim Ferriss?

  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.

• 2:39:04Derek Sivers?

  It's funny, the, the nature that these questions come to us and is usually one question asked, one answer expected. But if you think of the physical metaphor, just imagine that you are somewhere on Earth right now. So you're sitting in, uh, somewhere in Argentina and a phone call comes in and says, how do I get there? How do we get to where you are? It 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.

• 2:39:41Tim Ferriss?

  Yeah.

• 2:39:42Derek Sivers?

  It's not a soundbite.

• 2:39:42Tim Ferriss?

  So is the question, you've clapped your hands. So the question you wanted to ask, what question I think people are asking when they ask?

• 2:39:49Derek Sivers?

  Yeah. You answered that, thank you. Yeah, because I've always wondered, it's like, how do I, how do I think of that question? I keep getting that question all the time on podcasts.

• 2:39:57Tim Ferriss?

  Hmm.

• 2:39:58Derek Sivers?

  Like, ah, damn it, this question again. Like, what I would tell my younger son, like, I think it came up again just two weeks ago. It's like,

• 2:40:04Tim Ferriss?

  It comes up a good amount.

• 2:40:05Derek Sivers?

  Yeah, I need a good answer for that. Without the snarky saying, I don't understand the question.

• 2:40:09Tim Ferriss?

  Yeah, it's not a bad question. It's just so context specific that it's not just sometimes unhelpful, but I think dangerous to give too broad a response.

• 2:40:23Derek Sivers?

  Yeah.

• 2:40:23Tim Ferriss?

  To use your sort of geographic metaphor, right? You just send somebody off in completely the wrong direction.

• 2:40:28Derek Sivers?

  Go east.

• 2:40:29Tim Ferriss?

  Go east. Take two of these, come in the morning. Oh, shit, I'm in Antarctica. Sorry about that. Yeah, I thought you were in France.

• 2:40:39Derek Sivers?

  Can you go east from Antarctica? How do they do directions in Antarctica?

• 2:40:44Tim Ferriss?

  So, yeah, 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 gonna be, they're gonna be at some type of base of some type. I've only been once to Antarctica, 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 Mullin, I owe him thanks yet again for, for getting me down there.

• 2:41:23Derek Sivers?

  It was one of my favorite episodes of yours, that conversation with Matt in Antarctica.

• 2:41:26Tim Ferriss?

  Oh, 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.

• 2:41:38Derek Sivers?

  Yeah, that was fun. That's what I was asking.

• 2:41:41Tim Ferriss?

  Yeah, yeah, that was also, if I know Matt at all, I know that there's probably some Scotch involved with that as well.

• 2:41:46Derek Sivers?

  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?

• 2:41:59Tim Ferriss?

  Yeah, what do 16 year olds do? How do 16 year olds walk and behave? Do you want to explain the context?

• 2:42:05Derek Sivers?

  We, we took him to see John Wick 4.

• 2:42:08Tim Ferriss?

  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.

• 2:42:17Derek Sivers?

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

• 2:42:33Tim Ferriss?

  Even though he's seen and memorized all the John Wick movies.

• 2:42:36Derek Sivers?

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

• 2:42:53Tim Ferriss?

  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 gotta work on this a little bit. He had pulled the sleeves of his sweat. He had 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 pulled down the sleeves to make his arms look longer, but the, but the proportions were all wrong. So he looked kind of like ET. And I'm like, I think you're drawing more attention than you want to draw. But the whole thing was very cute.

• 2:43:38Derek Sivers?

  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.

• 2:43:46Tim Ferriss?

  Yeah. And your answer, when I asked you, what makes you emotional was anything related to parenting?

• 2:43:51Derek Sivers?

  Yeah. 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 always cry.

• 2:44:09Tim Ferriss?

  Hmm. Yeah, you're kind of tearing up right now.

• 2:44:11Derek Sivers?

  Yeah, yeah.

• 2:44:12Tim Ferriss?

  Wow.

• 2:44:13Derek Sivers?

  Yeah, it's serious.

• 2:44:13Tim Ferriss?

  Which is, which is new in my experience of Derek Sivers. It's like seeing this. Why do you think that is?

• 2:44:19Derek Sivers?

  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. It's like, if you do this right, it passes on. Wow. What shit?

• 2:44:39Tim Ferriss?

  Hmm. Right on any rush. Zero rush.

• 2:44:44Derek Sivers?

  Hmm, it's funny also collecting my thoughts on how to say this. I don't have to explain it much. Nobody's asked directly. It's like if you do this right, it passes on for many generations. A kid that's raised really well can like pass that generosity of spirit. And then somebody that's raised like ignored might pass on that scarcity of spirit, you know?

• 2:45:06Tim Ferriss?

  Hmm.

• 2:45:07Derek Sivers?

  Holy shit, I'm not doing this for the media. This is not like trying to be a captured moment. Holy shit.

• 2:45:13Tim Ferriss?

  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 though.

• 2:45:26Derek Sivers?

  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. I'm like, yeah, I just don't really like I'm a happy dude. Yeah, like this is the only thing, but it's like, it's not a, it's not a, obviously like not an upset cry. It's like, holy shit, this is such a big deal.

• 2:45:45Tim Ferriss?

  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 say? Any requests to the audience? Anything at all before we wrap up?

• 2:45:59Derek Sivers?

  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. They emailed to introduce themselves. And 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

• 2:46:44Derek Sivers?

  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?" You 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

• 2:47:26Derek Sivers?

  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.r s, yeah, just send an email and introduce yourself. That's my surprising

• 2:47:49Tim Ferriss?

  Do other domains point to that?

• 2:47:51Derek Sivers?

  It used to be sivers.org.

• 2:47:53Tim Ferriss?

  Yeah. You still have that, I assume?

• 2:47:55Derek Sivers?

  Yeah, I'm keeping that forever. But that's my minimalism thing. At one point, I looked at that, I'm like, "dot org."

• 2:48:00Tim Ferriss?

  Where is rs?

• 2:48:02Derek Sivers?

  Serbia, Republic of Serbia.

• 2:48:04Tim Ferriss?

  Okay.

• 2:48:04Derek Sivers?

  But one of my favorite tech sites is Lobsters, L-O-B-S-T-E dot rs.

• 2:48:10Tim Ferriss?

  Okay.

• 2:48:10Derek Sivers?

  I was like, "Hey, Lobsters."

• 2:48:12Tim Ferriss?

  Wait, what the hell is Lobsters about?

• 2:48:13Derek Sivers?

  Oh, it's just, it's just a random domain name they got, but it's like, 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 the way. Yeah, I looked at the dot org, and I used to have sivers.org, and I looked at that, I was like, "I'm not really an organization, am I? Those four characters aren't really necessary, are they?" I was like, "I think I could reduce those." And so, yeah, sive.r s.

• 2:48:37Tim Ferriss?

  All right, so sivers with a dot between the E and the R.

• 2:48:40Derek Sivers?

  Yeah.

• 2:48:42Tim Ferriss?

  Perfect.

• 2:48:43Derek Sivers?

  Yeah.

• 2:48:44Tim Ferriss?

  Thank you, Derek. So nice, so good to hang out, have some scotch, and...

• 2:48:48Derek Sivers?

  And make me cry, holy shit.

• 2:48:49Tim Ferriss?

  Talk life, yeah.

• 2:48:50Derek Sivers?

  That was my first time in like, three or four years.

• 2:48:52Tim Ferriss?

  I've never seen you cry.

• 2:48:53Derek Sivers?

  Yeah.

• 2:48:55Tim Ferriss?

  Wow. Exclusive to the Tim Ferriss Podcast, folks.

• 2:49:00Derek Sivers?

  Just trying to help out my friend, you know, get him some more views.

• 2:49:05Tim Ferriss?

  Views, maul the views. It's so good to hang out.

• 2:49:08Derek Sivers?

  You too.

• 2:49:10Tim Ferriss?

  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? Between 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.

• 2:49:53Tim Ferriss?

  And these strange esoteric things end up in my field, and then I test them, and then I share them with you. So 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/friday, type that into your browser, tim.blog/friday, drop in your email, and you'll get the very next one. Thanks for listening.

• 2:50:20Tim Ferriss?

  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. So what does that mean? That means in no time flat, you can have a great-looking online store that brings your ideas, products, and so on to life, and you can have the tools to manage your day-to-day business and drive sales. This is all possible without any coding or design experience whatsoever. Shopify instantly lets you accept all major payment methods. Shopify has thousands of integrations and third-party apps, from on-demand printing to accounting to advanced chatbots, anything you can imagine.

• 2:51:04Tim Ferriss?

  They probably have a way to plug and play and make it happen. Shopify is what I wish I had had when I was venturing into e-commerce way back in the early 2000s. What they've done is pretty remarkable. I first met the founder, Toby, in 2008, when I became an advisor, and it's been Spectacular. I've loved watching Shopify go from roughly 10 to 15 employees at the time to 7,000 plus today, serving customers in 175 countries with total sales on the platform exceeding $400 billion. They power millions of entrepreneurs from their first sale all the way to full scale. And you would recognize a lot of large companies that also use them, who started small. So get started by building and customizing your online store,

• 2:51:45Tim Ferriss?

  again, with no coding or design experience required. Access powerful tools to help you find customers, drive sales, and manage your day to day. Gain knowledge and confidence with extensive resources to help you succeed. And I've actually been involved with some of that way back in the day, which was awesome, the Build a Business competition and other things. Plus, with 24/7 support, you're never alone. And let's face it, being an entrepreneur can be lonely, but you have support, you have resources, you don't need to feel alone in this case. More than a store, Shopify grows with you, and they never stop innovating, providing more and more tools to make your business better and your life easier. Go to Shopify.com/Tim to sign up for

• 2:52:28Tim Ferriss?

  a $1 per month trial period. It is a great deal for a great service, so I encourage you to check it out. Take your business to the next level today and learn more by visiting Shopify.com/Tim. One more time, Shopify.com/Tim, all lowercase. This episode is brought to you by Allbirds, incredibly comfortable shoes, sustainably made with design rooted in simplicity. I am speaking from experience here. I've been wearing Allbirds for the last several months, and I've been alternating between two pairs. I'm traveling with them right now. I started with the Tree Runners in marine blue, in case you're curious, and now I'm wearing the Tree Dashers, and the Tree Dashers are my current daily driver. I wear them for everything. They're easy to slip on, easy to tie.

• 2:53:11Tim Ferriss?

  Everything about them is just easy, easy, simple, simple. I stick with the Blue Hoos, and the Dashers in this case are in buoyant blue. The color pops, I've received a ton of compliments, but putting the color aside, the Tree Dasher is an everyday running and walking shoe that's also great for light workouts. Super comfortable. And I've been testing it on long walks in Austin. I've also been testing it on the trails and pavement in places like New Zealand. And let's come back to sustainability. I mentioned that earlier. In the Allbirds Innovation Lab, they research how to make the most out of sustainable materials like leather made from plants, sugarcane, and tree fibers. In fact, the TreeDasher is made with eucalyptus tree fiber, something also found in New

• 2:53:53Tim Ferriss?

  Zealand, eucalyptus tree fiber to create a lighter and more responsive shoe. Allbirds is making shoes better than natural. They are supernatural. Find your perfect pair at allbirds.com today and use code TIM, that's T-I-M, for free socks with a purchase of $48 or more. That's allbirds.com using code TIM, A-L-L-B-I-R-D-S dot com. One more time, allbirds.com using code TIM.