#137: Breaking Rules, Solitary Socialite, Future Possibility Folders, Daydreaming and How to Live with Derek Sivers
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Kia ora, ni hao and hello. Welcome to the Chiwi Journal Podcast. I'm your host, Camille Yang. My guest today is Derek Sivers. Derek has been a musician, producer, circus performer, entrepreneur, tight speaker and book publisher. He's an author of four books, Anything You Want, Your Music and People, Hell Yeah or No, and How to Live.

In today's episode, we covered various topics including breaking the rules, solitary social life, future possibility folders, daydreaming, moving for good, New Zealand and many more. I hope you enjoy this conversation as much as I did.

Hey Derek, so glad to have you on my show. Good to see you again. Been a while. Yeah, since I have left New Zealand for a while, for more than three years. Yeah. So, and I'm a bit homesick. Shall we start with New Zealand? No, let's save that for the end. Okay. Yeah, that's good. I'll start with some of your articles that influenced me a lot. First one is "Move for Good",

So I remember we briefly chatted about this topic when we met in New Zealand and most of the people who we grew up with, they didn't choose the path to move around but stayed. So what do you think makes you different? I think some people just have that curiosity, that drive to want to take the more challenging path. You know, some people just want life to be easy.

They'll always choose the easier option. They would always rather relax instead of working. They'd rather watch TV instead of making something. Life is hard enough as it is. They just want to take it easy. And then some of us want to intentionally make things more difficult. We want the challenge because we like the feeling of growth that we get from doing difficult things. And so I think moving across the world to a culture that is very different than the one you know

especially if people speak a language that you don't know yet, is one of the most difficult things that you could do. But it's so rewarding because what happens after you do it is suddenly you have more places that feel like home. And that's such a wonderfully deep happiness, a real secure feeling to know that many parts of the world feel like home. So to me, it's worth the struggle, but most people don't feel that way.

Yeah, true. I know you moved to so many places. You too. Yeah, yeah, I did. Yeah. So if I say the one city's name and you give me an answer, like how this city changed your life. Sure. Ready? New York. That's where I learned to not be scared of what used to scare me. When I first arrived in New York, it scared the hell out of me. And only two years later,

it was my comfortable home. So that was the place where I started to feel the feeling of like, hey, places that used to scare me can become my new comfortable home.

Like, what part scares you most? Is it too big? Oh, no, it's just like, because I was like, yeah, I was like 19 years old. I grew up in a small town and suddenly I'm like, oh my God, New York City. And it's not just the physically looking at the height that just keeps going and going and going, but it's also the cultural baggage, you know, like New York City had this reputation as being this tough place. This is also like less so now than when I first moved there.

The crime was way worse than it is now. And so New York City was known as this like tough, dangerous place. And so filled with all the cultural baggage and then just the visceral overwhelm of being there. It was scary when I first moved there. But then within two years and still, it's my comfort zone. I'm so comfortable in New York. Every neighborhood, anywhere. I have friends there. I love it. Cool. Next, Singapore.

That's when I realized that I was just an American. Up until Singapore, I had been living in lots of different parts in America, and I still thought that I knew what was right and wrong. I thought I had the answers. Once I got to Singapore, I found a perfectly working philosophy that was completely opposite of mine. You know, this kind of Confucian approach to life that felt wrong when I first arrived.

But after a while, I started to understand it and it made sense. So then I felt like I know nothing anymore. 15 years ago, I thought I had all the answers. Now I know that I know nothing. Wellington. I don't love Wellington. I'm just here out of some accident of necessity. It's an ugly city. It's too dense, way too much advertising. I wish they would have

made some kind of regulations about how much advertising you can put because every bit of space is taken up by real estate advertising and it's just really ugly advertising.

I don't like it. So, yeah, I have nothing else to say about Wellington. But you moved there second time, if I'm right. Like, what made you make this decision? Yeah, just my ex-wife's job. That's the only reason. Okay. Last city, Oxford. Oh, God. I love Oxford. I'm really sad that I'm...

Not there anymore. I loved it thoroughly. I loved living there. I loved the... It is just the right size for me. I think it's gorgeous. I think it's...

smart and cultural. I love the location. It's handy to get to Heathrow Airport, which then brings you everywhere. I love that it's right on the edge of the countryside. I just love the people it attracts. I even like the weather. I like English weather. Yeah, same. I just love everything about it. And I just stumbled into like a perfect, wonderful house. I had this wonderful little cottage house there that I just adored. I never wanted to leave. But I moved there in 2019 and

planning to stay for 12 years, but then COVID hit and that plus some other like family stuff just had to kind of make a family decision to move back to New Zealand. So I miss it dearly. I mourn for it. I grieve. Yeah, I think it

For me, I live in London for two years. Once I left it, I miss it deeply. And I'm now in Lisbon and it's like sunny day every day. But I talked with my friend. I miss England weather. It gave me so many inspiration. Yeah, it's very interesting. And I can see sometimes just life leads you to different parts. And

probably don't have a choice. You may have a choice. I mean, yeah, you always have a choice. You never have to do anything, but you gotta, if you take other people into consideration, you know, it's not just about you. Yeah. So, so yeah, I had to make it, if it was just up to me,

I would probably just be fully nomadic, but wanting to do the best thing for my son and his mom, here we are. When did you find out you start to like more consider about others? I know in your book, your music and the people you see meta marketing skill is being considered. In your business and in your personal life, when do you start to have this philosophy?

I think that was just marketing. I think that was just realizing that that was the essence of marketing really comes down to being considerate. Marketing isn't shouting. Marketing isn't advertising. Marketing isn't annoying people. Like real marketing is all about being considerate and making it easy for people to remember you and helping them see why they should be

do business with you and making them feel good about doing business with you. That's what marketing is really about. And to do all of those things well, you have to be considerate. So I think that's where my focus on being considerate came from was when I started learning about marketing, when I was trying to promote my music and then later my business. Yeah. What about your personal life? I think that comes more from having a kid.

I'm not just saying this to sound like a good dad, but, you know, my kid just objectively matters more than I do. You know, he's got more life ahead of him. Therefore, his life matters more than mine. So I put his needs above my own for just that very... Part of it's just love, but a lot of it's just practicality. No, not practicality. What is it? Ration. It's just the rational thing to do, to place...

Your kids' needs above your own. I see. Since I haven't had a baby yet, so I probably can't understand this. Maybe one day. Maybe it's easy to imagine. Yeah. It's not so hard to imagine that, yeah, when you have a kid and you just realize that this kid's life matters more than yours, just objectively. Since you have done so many different things and have so many different titles and identities,

I wonder how did you find out that identity is no longer yours? And what do you feel about when you say goodbye to your old identity? If an old identity was fully realized, then I'm happy to leave it behind. For example, I was a professional full-time musician for 15 years. I did it well. I did it thoroughly.

I did it for 15 years and that was enough. I'm happy to, I'm happy that I did it and I'm really happy to leave it behind. CD Baby, I was an entrepreneur for 10 years. For 10 years, I felt like a public servant. Like I was living 7 a.m. to midnight, seven days a week for my clients. Like everything I did at every waking moment, I had no personal life for 10 years. I didn't go out. I didn't go to restaurants. I didn't travel. I just lived for my clients.

every waking minute for 10 years. And I'm glad that I did it and I'm glad that it's done. I think the sad thing is when you have an old identity that was never fully realized. Like, for example, like 20 years ago, maybe 15 years ago, I said, I really, really, really want to learn Mandarin Chinese. I want to speak Mandarin and I want to be able to write Chinese fluently. I love the written language, especially English.

I want to do this. But for 15 years, I haven't really done it. It's even part of why I moved to Singapore was because of the language, because it's one of the, where it is the only place except mainland China where they use the simplified Chinese. And I thought that's the one I want to learn. So I'm moving to Singapore partially to learn Chinese, right? And, but it was always like fifth priority under other things.

So I just never really got around to it. And now after like 15 years, it's just admitting, you know what? I don't think that's ever going to happen. So I'm just going to let that one go. But there's something kind of sad about that. You know, I really did want it, but I just wanted other things more. So that's a little sad to let go. And, you know, the thing I was saying about Oxford a few minutes ago, that wasn't just Oxford. That was like, we made like a big family decision. Like my kid's going to grow up in Oxford. He's going to live in Europe.

for the next 12 years of his life from the age of 7 to 19, this is where we're going to live for 12 years. He's going to grow up here. I had so many plans of all the places I wanted to take him, places I wanted to discover myself, not just, you know, visiting a place once. I don't mean like looking at the Eiffel Tower, but like really getting to know all these adjacent cultures. I was really looking forward to that. I had really big plans for my kid to grow up that way. And after only 13 months...

you know, COVID hit, it derailed everyone's life. And so like, I really, I mourn for that. That's, that's a hard one to look back at. And I don't feel okay about the fact that that's not going to happen. So how did you cope with this disappointment? I just, I'm, I'm very disappointed. Just accept it. I don't know if I fully accept it. It's just, oh, well, that's life.

You can't have everything you want. You can have anything you want, but you can't have everything. Exactly. Before I moved to England, I planned everything. I'm going to watch the Euro Cup. I'm going to all the writers' residency to visit. I planned my whole Europe trip. Then COVID hit.

So it's kind of pulled to form my plan for two years. I'm glad you were able to move to Lisbon. Everything you know that that was a place that I almost lived as well. Yeah. I became a legal resident of Portugal and planned on living there and then...

you know again just family things happened and it didn't work out but oh well I remember I emailed you to ask you about what do you think about Portugal and you said it's a little bit sad and dirty oh that was private put insult Portugal on the air sorry I think I do feel like it's like New York and Lisbon it's all very dirty but I think it's part of their city's identity yeah true

Yeah, New Zealand is clean, but I don't have that deep connection. I don't know why. So clean is not my priority when picking up the city. Yeah. What are some of your life-turning points to make you rethink your principles? Let's talk about the, say, like the first time you...

I discovered the benefit of breaking the rules. I was 17 years old and had just gone off to university. I went to Berklee School of Music. So 17 years old, got on an airplane, went far away to the city of Boston. I had never lived in a city before. It's my first day there.

And everybody was checking into their dormitories. And we had all been assigned a room. You know, like the school takes care of that in advance. They say, you'll be in room 312, you'll be in room 163. So I went with my friend first to his room. So we checked him into his room and his room was huge with a bathroom.

And then I went to go check into my room and it was, it was like this booth I'm standing in right now. It was just this tiny little room with a bunk bed and just enough room to walk around the bunk bed like this sideways. And there were supposed to be two of us in that room. Like they wanted two people to live in that tiny room. That was just a bunk bed and room to walk around it. Not even a desk.

And no bathroom, no nothing. And I just took one look and I just said, oh, hell no, I'm not doing that. So I totally broke the rules and found somebody whose roommate didn't show up and had an empty room like they had a suite.

And nobody had showed up for the other half. So I found out about this. And so I knocked on their door and I said I was the roommate. I said, oh, this is my room. But for some reason, they must have given me the wrong key. But this is my room. So, hey, I'm your new roommate. I'm Derek. Nice to meet you. And for a whole week, I climbed in through the window because the housing office said, absolutely not. Go back to the room we assigned you to. And I said, absolutely not. I won't.

And they said, you are seriously breaking the rules. And I said, I don't care. I refuse to sleep in that room. I'm sleeping in this room. I'm climbing in the window. I'll do this all year if that's what it takes. And after about a week, they finally relented and they gave me the key. And when I look back, I'm so proud of myself.

little 17 year old Derek that did that you know like that's really cool to stand up for stand up for yourself and not take the rules too seriously to be resourceful to make something happen instead of just going oh well I guess that's what I'll just have to do then you know I think that was a turning point as you said of like learning to break the rules

It's a good example. I remember you mentioned a story in your book or your article. When you were in school, there was a professor going to give a talk, but he didn't eat. So you order the pizza, then it leads to give you some mentorship or something like

If I remember correct. I think it is also a good example to notice something someone else didn't notice and give you, open the door for you to some opportunity. It reminds me when I first noticed your website, I read almost everything on your site. And I'm very fascinated about the terminology you coined.

solitary socialite. Oh, the solitary socialite, yeah. What are the pros and cons of being a solitary socialite? The two pros are first that it's efficient. I mean, it's so efficient to meet everybody by email that I go through about 100 emails a day and I can do it in about 90 minutes. Like I do it in under one minute per email. I can have one-on-one communication with people

100 people a day in 90 minutes. And that's so efficient. And I have this program that I like a database so I get to keep track of everybody I've communicated with and I can see our email history. I keep track of where people live and what they do and their URLs. And I follow people on Twitter and stuff like that. So it's really efficient to keep in touch with lots and lots of people. Another surprising thing I like about it, about the solitary aspect, is I don't

I usually know the age or the race or even the gender of who I'm talking with. It's funny, I just realized that with the, I guess there's some languages where I'd have to use a different verb if it was masculine or feminine for who I was talking with. But in English, you know, I don't know.

Often, like there have been some times where I've been emailing with somebody for years and found out that they were much older than I thought. And like the other gender, you know, like because sometimes there are these names like Bobby or Robin where you can't be sure what gender somebody is. And I've been surprised a few times to find out that

I thought I was emailing with somebody from a certain demographic and they were completely different. And even like the race thing has surprised me a few times. Like I've been emailing with somebody for years and then they say, oh, hey, look, I made this video. I'm like, oh my God, I was not expecting that. And I like that. I like that it's just like I'm dealing with people just for their ideas, their words, not their face, you know, not their age. So what's the downsides? The downsides is because...

Because I'm doing this all by email and so quickly, I never ever do Zoom. Ever. Only when doing interviews like this, like podcast interviews. But never just for talking to people. So the downside is that I don't remember people as much. So I'm sure that I've emailed with a photographer and a lawyer and a programmer in the past week. But if you were to ask me, hey, can you recommend a programmer? I'd say, I don't know. I just, I interact with people so quickly that

that I don't know who's good. I don't know their work. So say when I lived in a very social city, like when I lived in New York City, Los Angeles or Singapore, I met face to face with a lot of people and then I'd really get to know them and get to know their work. I'd get to know their temperament. Yeah. I'd get to know whether I would actually recommend them for a job or not, you know? I love the sounds of the city as we're talking about the city. Yeah, sorry. I say, yeah, I should have got the... Yeah, the...

Yeah, the booth like you. That's something about moving around. You can't set up the permanent recording thing. You just need to accept that. I echo with your dealing with people online because I've been emailed

A person named Shaonan is in Chinese. You probably assume it's a girl. So I kind of send many like kissing, kissing and very intimate emojis. And then like after half a year, I found out that he's a guy. I love that. Yeah, I feel so embarrassed. I said, oh, sorry about that because I thought you were a girl. That's why I use this kind of emojis.

but he didn't take it in mind because we kind of just communicate with the ideas. I know you keep writing and doing a lot of creation. Why do you think you should not wait for inspiration to come? That's just a basic fact of life is that

Inspiration will never make the first move. She only will meet you halfway. So you always have to start working without inspiration. And only when you've begun working without her, then she will come join you. That's just a fact. Like, ask anybody who...

is any kind of professional creator and they'll tell you the same thing. So yeah, I've found it personally, but it's like, I've also read lots of interviews with creators and they all say the same thing. You cannot wait for inspiration. Yeah, so true. Yeah. Cause I put a Hemingway's quote on my website. There is no secret to writing. You just sit down and tap, bleeding. Yeah. You just need to do it to do the work. The muse won't just come randomly. Yeah.

But do you think you should, if you like travel, when you travel or try some new experience, you get new idea, will you consider that as inspiration? Sometimes, rarely. You'd have to really go out and engage. Like you can't just kind of, I don't know. I mean, some people might get some inspiration by just being a tourist somewhere. But for what I've done, inspiration...

No, I don't know. I think the inspiration rarely comes from the outside world to me. The inspiration is very often just comes from the work itself. You begin writing or doing whatever you're doing. And then the inspiration comes just from all the culmination of your life experience up to that point. Not just because you saw something pretty in a strange place today, you know.

Yeah, it's kind of, it's already inside you. Some external effects just triggered you. So you can make the connection. I read something you kind of like train your kid to be very focused. Is that part of your secret to be so productive on creating and writing things? I don't know if I'm so, I don't think I'm very productive. I've done a lot over the years, but if you look at how much some people write articles

you know, every day or put out something every day or every week. I'm not one of those. So I don't think I should be giving any secret on how to be productive since I'm not productive. I should also not be giving any secrets on basketball tips. I think maybe this is a wrong word because your content to me is very high quality and very inspirational. So would that focus play a big role in there? Maybe. I think it's just...

I work for a long time on the stuff that you see me put out publicly into the world. I might put out a little article that's only 20 sentences, but I worked for like eight hours on those 20 sentences, you know, or my, my Ted talks that are out there. I think I have three or four, maybe three, three Ted talks that are just like three minutes long each. I worked for months on those. That was like a full-time job for two months, but,

to get up there and deliver a good three minutes. You know, that was so much work.

to give a three minute talk. That was a month and a half of my life preparing that three minute talk and getting it just right word for word. And so it's like that with the articles that I put out and the books that I do. It's like, I spend a lot of time editing and sweating over every word, which really comes out, like ultimately that comes from wanting to be considerate. I don't want to waste anybody's time. I don't want to pollute the world. I don't want to put out any sentence that

Into the world that doesn't need to be there. So I want people to know that any time you're getting anything from me, whether it's a book or an article or a talk, that I'm not going to waste your time. I'm going to give you the absolute best and minimum number of sentences I can so that you can get the best benefit in the minimum time.

I can't remember who said that before. He mentioned, okay, this is the long answer for your question because I don't have time to shorten it up. Oh, yeah. It's a credit to Blaise Pascal, I think, long ago. Yeah. Uh-huh.

Yeah. It really takes effort. Like when you read some short and sweet article, maybe this like a couple of months work behind that. I know there's another article you talk about, about daydreaming. Cause this is one of my favorite leisure activities. I like to daydream. So what are the benefits of daydreaming? Oh God, it's all of them. I mean, it's,

your brain doesn't make a big distinction between something you're imagining and something you are actually doing. Sorry, this is going to sound stupid, but like, you know, when you physically touch something, all that's really happening are the nerves are sending messages to your brain. But ultimately, it's your brain that receives the messages from the nerves saying that you're touching this thing. And same thing with your seeing things, you know, it's like hitting the back of your retina, but then it's nerves that are sending the messages to your brain saying that you're seeing this thing. So

When you imagine something, it's almost like it's really happening to you, especially if you let yourself imagine vividly. And whether that's just closing your eyes on the sofa and daydreaming like that or making really concrete plans. Like I often love making really specific concrete plans. Like I'll have some daydream about, you know, how I'm going to build a forest in India and daydreaming.

I'll spend weeks planning it and I'll talk to people and I'll find out more about this and I'll get all the facts and I'll spend many hours making a specific plan. And it's really exciting and fun. And after a certain point, I think, all right, well, I might do that. I might not. But now I've got something else that's interesting me. Now I've learned about the Esperanto language and I want to do that for a while. You know, so it's okay to just let yourself go.

vividly dive into these things that you might do or just imagine doing, or maybe you know you're never going to do it and you just want to daydream. I think it's all wonderful. Because I have so many interests and I'm very curious about everything, but I know I can't do everything. So I like daydreaming about it. I've already done that. Just imagine that. Yeah. This connects to another article about future folders.

a future possibility fail would you mind elaborate this idea oh it's kind of just what i just said it's um i used to feel bad when i would not make an idea happen you know i spent weeks planning how i was going to build a forest in india and i would feel bad that i didn't do it after all that work and eventually i just realized that um i can just save all that work in a folder

and put all of those folders in a bigger folder called possible futures. And then someday, if I want to make it happen again, I can just pull up that folder and

get back to it. Maybe I'll make it happen or maybe I'll just leave it as it was. So yeah, now I don't feel bad about any time I spend planning something that I don't end up doing. I just consider them all possible futures. So do you believe in like a parallel universe? Derek Silver from another universe already done that. Maybe. Doesn't matter. This one is okay. Just daydreaming about it.

I see you finished the How to Live and I see so many conflicting philosophies in that book. I'm so proud of that one. That's really, that's my soul in there. I love that book. It takes years for you to write it, right? Yeah, it was so rewarding. Yeah, that was like four years of hard work to make it that

small. It would have been easier to make it much longer, but to condense it down and make every sentence count, that was a great feeling. Oh yeah, here, I have a little tiny one here. I just, I love how tiny this is. I love it. It's like 118 pages and so much of my soul is in there in 118 pages.

Yeah, and it's easy to carry when I travel. So I like your book. It's not like I carry something like a Bible. After reading your book, I feel like there is no right or wrong way of living. Because, you know, in our society, so many people just follow one single path.

the society told us to do. But after reading your book, I think, wow, there's so many possibilities. Does that mean for each individual, they have to dig deep in their heart to find their way of living? Like what do you want this book to achieve? I think the punchline at the end of the book is a picture of the orchestra. And to me, it's like the different ways you could approach your life

are like the different instruments in an orchestra where a composer or conductor never has to decide, well, okay, of these 27 instruments, which one are you going to use? They don't have to decide that because you can make combinations of them. You can use combinations and you can use time. So they can say at the beginning, I'm going to have just the flute and a drum.

And just the flute will come in and then the clarinet will join it. And later I'm going to have the trumpets come in and then it's all going to stop and there's going to be just a harp. And it's like this with your different approaches to life. You know, you can, you don't have to pick one. You can say for now, I'm going to be a hedonist, but I'm going to do it in Cambodia, which will help me save money and just live a hedonist life surfing on the beach. Later,

I'm going to go back to school and get my master's degree, and then I'll be head down getting my master's degree. But after that, I'm going to move to somewhere boring because that's where I met somebody from this boring place, and we've decided we're going to go there and have kids. And all we're going to do is just be with our kids in nature.

And then at a different time, I'm going to get a good paying job in San Francisco and make a lot of money. You know, you don't have to pick. You go, you use them with time and you combine them. Yeah, experience different things. Yeah, so you don't ever have to decide. You don't have to look deep into yourself. You can just go with whatever's happening in your life and know that you can use time. I don't know if it's my age now or, you know, some social...

Like peer pressure. Oh, you are in your 30s. Now you should settle down, have a family. So what's your opinion on like move for good and settle down? Oh, well, like that to me is like a... That is my preferred way to travel is to consider or assume that wherever you are now, this is where you're going to stay. So this idea kind of came from an art teacher that said...

that when you go to a museum, you should pretend that you have to buy one piece of art in this museum. And which one is it going to be? And that makes you look at everything very judgingly. You have to decide what is your favorite and look at things very intensely. And so kind of like that was his recommendation for here's how you should go to a museum. I'm saying here's how you should travel. You should assume that wherever you are,

that this is going to be your permanent home for the rest of your life. You are now a local. So instead of asking how they do things, you should be asking how do we do things here? Like how do we tip here? How do we pick a home? How do we hail the waiter at the restaurant? Whatever it may be. You should really internalize it and think that this is your permanent home and think like a local and try to become a local

And even if you end up leaving weeks later, I think you'll have a better experience if you assumed that you're moving there for good. But not settling down, not just because it's like, well, Miss Yang, you're in your 30s now, you should settle down. That's just silly bullshit. No, I don't buy this. But sometimes I got that noise around me. And I found this very interesting. A lot of people travel in a group.

And every time they go to a new place, it's still that kind of group of friends, but they just change the location for drinking. I just can't understand. Yeah. They don't take time to learn local culture, but just change the place to drinking. It's very funny, in my opinion. Yeah.

You have another article about you can live in one place but think globally. That's what you did in New Zealand. You did the opposite way when you were in Singapore. You just indulge yourself with the local community. Have you changed the second time you moved back to New Zealand? No, I think I'm still global. I think New Zealand is my... I love it physically physically.

More than socially. I never wanted to be social in New Zealand. I always thought of it as like my...

natural place. I mean, I like the people here. Yeah. I like this being my international home base. Because for me, I feel like it doesn't matter where I live now since the internet is so convenient. I can talk with you and other people who I found I want to learn from. Yeah. Quite interesting to see like whether your physical bodies live not matter that much.

I wonder if you feel the same. Yeah. I mean, it matters somewhat. You are affected by your environment. I think it would be depressing to be in a place where everybody felt hopeless and depressed. Even if you were in your room on the internet connecting with inspiring minds, I think it would still feel a little bleak to be living in a place where everybody around you was hopeless. I think it would be more depressing

exciting. I have felt much more excited when I've lived in places like New York and Los Angeles and San Francisco, where I was surrounded by really ambitious people doing really interesting things. London too. London was great for that. Meeting so many ambitious people doing interesting things. They were really excited about something and then

you meet them and pretty soon they're introducing you to somebody else they're working with and collaborating with people. And it's like, that's wonderful. I mean...

Yeah, we can sit in Bali and use the internet worldwide, but something special happens from being in the same place with other driven, ambitious people. Yeah, I think the energy and the vibes just give you more different things. Like in Lisbon, when I moved here, I just like this digital nomad environment. So many entrepreneurs and founders here. I go to some events, then I go to New York.

and some collaboration opportunities. That's something I won't be able to get in New Zealand. So I feel like, hmm, that's good. But the downside is the weather is so good. Every time I stay home, right, I just feel like, oh, I want to go outside. That's the opposite of London. Yeah, I was like that when I first moved to Los Angeles. Like every day I didn't go out to the beach, I felt a little guilty. And eventually I just realized like, you know,

It's always going to be nice here. I can go next week. I just need to work today. Yeah, there is a question that bothers me a lot. I'd like to seek your opinion. You know, when people like to use stereotypes or to prejudge people, when people look at me, oh, you are Asian, and they probably have some stereotype. But...

Actually, my behavior probably is very different from what people think about Chinese girls should behave. So I wonder why people always use stereotype. It's like too lazy to think out of all side box. Yeah. I think it's just efficient. I think it's just efficient and they just don't care that much.

you really get to know one person. If you meet somebody that really cares about you and wants to know you better, then they will ask you a thousand questions in order to get to know you better. But most people that are just interacting with you on some kind of transactional basis, it's just efficient. It's

And they're sometimes correct. That's why they're stereotypes, is that they came from something. So, you know, it's maybe the, even if it's only 55% of the time, if they can make some assumption like, oh, you're from here, well, then you're probably this. It's just a quick way to get through life. I don't think you can take it personal. They're just being efficient. I see. Have you ever encountered any stereotypes or...

like people think of you as wrong. Yeah, but I mean, I think they're often right. You know, they think that I'm like a brash American. I think, oh, yeah, I guess I am. You know, I mean, that's when you asked what I learned moving to Singapore, I think it made me realize how American I am. Because in America, I felt kind of strange. I didn't feel like an absolutely typical American when I was in America. I thought of my distinguishing features that were not like the people I was surrounding. But then

When you put me out in the rest of the world, then yeah, compared to the rest of the world, I'm very American. So I'd say that when people have made a stereotype about me, it's often turned out to be true. In fact, when I moved back to Wellington, twice now, twice, when I went to go meet somebody in person for the first time, somebody who I'd been emailing with,

maybe even talk to you on the phone and now I was going to go meet them in person for the first time. Twice, the person I was meeting with accurately predicted before I arrived that I would show up in a Nissan Leaf and they were right. That I have a Nissan Leaf, which is like, because I'm not going to splurge on a Tesla, but I'm not going to drive a petrol car.

So I'm going to have the all electric car, but I'm going to be cheap about it. That's kind of the Derek Sivers way, you know, and, and they, they stereotyped me to assume that about me and they were dead right. And I pulled up in a Nissan Leaf and yet twice, two different unrelated people that don't know each other a few months apart, both like, as soon as I arrived, they're just like the person they were with. They're like, I told you my bet, you know, Hey, you won the bet. We knew you'd come in a Nissan Leaf. We figured you were a Nissan Leaf kind of guy.

So, yeah, I don't mind stereotypes. They're they're fun. They're efficient. But, you know, I know that I know other people that whose feelings get really hurt by them. They're sick of being assumed that because I look like this, you think I'm going to be like that. I can see the downside to it, but you can't you can't take any of it personally. You know, people aren't thinking of you personally. They're just they're just going through life. They've got their own life to worry about. They're not thinking about you.

Yeah, exactly. That's the thing I started to realize. Yeah, it's not all about you. People just think efficiently. I even wrote a book about why people always use stereotypes to judge me like two years ago. Because back then, I got an identity crisis. Why people always put me into a Chinese girl's box. But now I feel like, yeah, as you mentioned, it's not all about you. It's just so.

Daily encounter, people just, yeah, efficient. What's something about you is different from a typical American stereotype? God, I don't know. I mean, when I, you know, in America, there are these different pockets of cultures. So when I was in Chicago, I never felt I fit in. I moved to Boston, I didn't fit in. I moved to New York City, I didn't fit in. And then when I went to San Francisco, I went, oh.

I fit in almost too much. This is creepy. Everybody's like me. So I think that I was born in Berkeley, California, which is part of San Francisco. I lived there till I was five and then moved around the world. But I think maybe because of my parents or something that that San Francisco or California culture just stayed with me. And so when I'm in California, it's almost creepy to me.

how much I fit in, how everybody is like me, how I'm like everybody else. So no, I don't think there's anything special about me. How do you balance, like, adapt to locals' life and fit in? Because you mentioned when you were in Singapore, you kind of want to indulge the local culture. Oh, yeah.

No, I mean, I don't pretend to be somebody I'm not, but like, I, I think it's about understanding. I mean, sometimes it's just in, in your behavior and the way that you act. You don't, I don't come in acting like a brash American if that's rude and off-putting. I might internally keep those same beliefs, but externally I'm going to be considerate. Yeah. I think it's more about understanding. It doesn't mean that, doesn't mean that I need to be a chameleon and be

completely blend in and pretend I'm from there. But I think it's more about understanding. Yeah, the empathy and the connection of understanding people and understanding how you fit in into their world.

I still remember when we first met in New Zealand, you showed off your Chinese. Oh, God. What's the sentence again? Oh, God. My one ridiculous... Something about TV. Yeah. Okay. Yeah. That was... 我现在不想看电视。

I don't want to watch TV now. I learned it from a grammar lesson, the Michelle Thomas Mandarin method, where they don't teach you vocabulary first, they teach you grammar. That sentence was used to show off the grammar of saying 我现在, so I now, 不想, so no, would like, 看电视, watch TV. And I just thought that was, I just liked the way that sentence sounds. Yeah, that's so cool. Yeah, because

Because I was thinking to learn Portuguese, and then I asked you for some recommendation, but it's not my priority. And people in Lisbon, they all speak perfect English, so it's not necessary for me to learn. The Michelle Thomas Portuguese audio by Virginia Catmere is really, really good. It's a wonderful introduction to European Portuguese, and so is practiceportuguese.com.

They have a great, yeah, for learning Portuguese. To me, the combination of those two things, you'll learn not Brazilian Portuguese, but you'll learn real Portuguese Portuguese.

And that's, those are my favorite resources. Yeah. My favorite writer, Fernando Pessoa. He's a kind of inspiration for me to want to learn Portuguese. I want to read his work. Yeah, that's the reason. Yeah, in his language. But now, there's so many things going on. It's not my priority, but eventually I think I will learn. Yeah.

It's so beautiful, Portuguese. Because before I moved to Portugal, I never thought about learning Portuguese. Because French and Spanish are more popular than Portuguese. Do you have any inspirational writers you regard as heroes? Oh, all the time. In fact, I don't remember her name right now, but by the time this...

A podcast goes live if you go to my book page on my website, sive.rs slash book, where I post all of the notes from the books I've read. If you sort with the newest at the top and look for the book that I've read on the 28th of July, I just finished it yesterday.

It's this book about philosophy, the complete introduction to philosophy. And the woman who wrote it, oh my God, she's one of the most, one of the clearest writers I've ever encountered. She takes these incredibly complex, hard to explain philosophical concepts or everything that a philosopher like Nietzsche or Immanuel Kant taught and compresses it into an incredibly easy to understand 15 page chapter that

It's breathtaking. She's one of the best writers I've ever encountered. And I just emailed her yesterday to tell her so. She's a professor in Ohio. So amazing. So yeah, I think I'm constantly finding writers that impress me. But, you know, the bar keeps getting raised. So then I get really upset when I encounter a writer whose content is

I would like, but I hate their writing style. If they get too flowery or too verbose, it's really frustrating to me because I really like it when people are simple and succinct. I remember one friend asked me, "Who do you want to meet in this world?" And I think I probably want to meet a writer, but I can't figure out who, which writer alive I want to meet. I have the writers on my list, but they're all dead.

yeah I mean there's some good ones I mean I love Mark Manson's writing oh yeah he's good yeah when I read a book and then I take their ideas and I try to put it into my own words and try to say it better than they've said it and one of the only writers that I just can't improve on is Mark Manson like every sentence he writes I look at it I'm like how can I make this better and I'm like

can't damn it he nailed it he's so good yeah i joined his uh private book club oh cool zero fuck game club it's kind of like nft stuff yeah i asked him about my commitment issue because you know i move around and even for my relationship normally just last for three months then down yeah

So his advice for me is just make a damn commitment and then stick with it. Don't think about it. Okay. Yeah, there can be the separation between your mind and your body. You can let your mind wander, but let your body stay committed to one thing. Let the others be possible futures. Hmm.

Yeah. So that would be your advice for me as well, if I ask you this question. I don't know. I don't know about advice. Advice is so full of shit. Cool. Okay. Last question about New Zealand. Oh, all right. So what's the differences you find out the second time you move back compared with the first time you live there? Oh, none. That's what I imagined. No, it's...

No, I mean, look, this is my favorite country in the world. Even though you heard me talk poorly about Wellington, I love almost everywhere else in New Zealand except Wellington. And it was just through some circumstance that this is like, like I said, it was like because of my kid's mom, who's my ex, and the job that she got. And so this is where I am. It's fine.

I don't care. I actually like the weather. I like the windy. Okay, so Wellington, as for anybody listening, Wellington, New Zealand is officially the windiest city in the whole world. There are windier places in the world. I'm sure the South Pole is quite windy. But as far as cities go that are over a certain size, Wellington is the windiest city in the world.

And I like it because it keeps the air clean. It has some of the cleanest air in any city because of the wind. It's just, you know, at the very tip. So it's like ocean to the west, ocean to the east, and the wind is just blowing through all the time. So it keeps the air really clean. The landscape around Wellington is wonderful. So I'm fine with living here. I just, I don't like Wellington, the city, but I'm, I like the Wellington area. New Zealand. Okay. So like I referred to this earlier, but like when COVID hit,

And I was living in England and my ex was there and she didn't like it. And so we kind of like had to make this big family decision of,

where to go. And do you remember when COVID first started, we didn't know how this is going to turn out. We didn't know if this was going to last one year, 10 years, maybe this is just the new reality. Maybe like we'll, nobody will ever travel ever again. I didn't know what kind of tribal wars were going to break out and people locking their borders. Like we just didn't know. So I had to ask myself when it first hit, if I could only be in one country for the rest of my life,

and never, ever be in another country ever again, what would that one country be? And to me, that was just obviously New Zealand. So that's what made the decision to move back here. Like, this is my real home. I'm a citizen. It's my... That's where my heart lies, is here. My possible futures and my daydreams might lie elsewhere, but my heart is here. And it's my favorite single country in the world. So...

Yeah, I'm happy being here. Very happy being here. I think Wellington has a very famous burgers festival every August. I don't know if you heard about Wellington on a plate. Yeah, Wellington on a plate. Lots of burgers. Great. All right. I think that's a thing. They're all $30. Yeah, it's very expensive. Yeah. But that's a burger thing I missed about Wellington.

And the sun on the mountain, welling wood. Yeah. Yeah. It's like a blower way. It's quite interesting. Yeah. Yeah.

Cool. I think, yeah, it's one hour now. And thank you so much for your time, Derek. Yeah, it's good to see you again. Yeah, I appreciate that. I'll probably go back to New Zealand end of this year. Cool. If, yeah, you're free, we can catch up in Wellington. You mean, are you thinking of moving back or just visiting? No, just visiting. Yeah. Okay.

You're going to stay in Lisbon, right? I don't know yet, but for this year, I think. Oh, okay. That's the commitment thing. We'll come back to that in another conversation. I'll ask you again next year. Yeah, for this year, I'll definitely stay here. Still need to explore the city, explore Portuguese culture. Thanks for listening. That's the end of the conversation.

Please make sure you check out Derek's website at sive.rs and introduce yourself. He would love to know where you are and what you are working on.