Flynn Skidmore
host: Flynn Skidmore
New York City memories, gentrification and its impacts, journaling, beliefs as tools
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Transcript:
Flynn
Derek, I’m so, so happy to have you here already your energy, your facial expressions have been fantastic. Truly. Yeah. So much life in the way that you’re communicating. And I’m really happy to be here with you.
Derek Sivers
Thanks, Flynn. Yeah, before we hit record, we were already vibing out about New York City. What neighborhood did you grow up in?
Flynn
I grew up in Fort Greene.
Flynn
My parents, my parents moved there in 1985, and I grew up in Fort Greene, and I lived there until I was in my early 20s.
Derek Sivers
Oh, wow.
Derek Sivers
It was such a different time, wasn’t it? I moved to New York City in 1990, and people who think of it as this gentrified city now can’t understand, like the danger it had in the late 80s and 90s. You know, it was not a safe place.
Flynn
It’s so cool. So I’m about the age now, a little bit older now than my parents were when they decided to move to Fort Greene in 1985. And, you know, like given my social circle, given what I have access to, what’s normal in my network, I don’t know anyone who’s making a decision to move to a neighborhood where there’s a high likelihood that you would get robbed or something like that. And Fort Greene is such a beautiful, culturally rich neighborhood. And when my parents moved there at the time, high likelihood of getting robbed, like pretty, pretty dangerous place, pretty high crime rate. You know, I love my parents in so many ways, and they are complex people. And it really makes me appreciate them to that they are the type of people who made that decision, because I don’t know anyone who would make a decision like that. They were hungry for culture. They were hungry to live in a place that architecturally was beautiful. They didn’t want to be around white people, and that’s just very cool to me that they sought that out.
Derek Sivers
Wow. And so for you growing up there, I’m sure at the time it just felt normal. But I don’t know. How old were you in 85 when you moved there?
Flynn
So in 85, I was negative, five years old. I was born in I was born in 1990. So my parents were in the neighborhood for about five years and then had me in 1990. Yeah.
Derek Sivers
Oh, I didn’t get you were that young. So even the stuff I’m saying about, like how New York City felt in the late 80s, early 90s, you weren’t really, you know, you were crawling, not.
Flynn
Late 80s, early 90s. No my my recollection is really mid 90s, late 90s, early 2000 as a kid. Yeah. So you and I arrived in oh, God.
Derek Sivers
Well, that’s when it really started transforming was kind of mid 90s gentrification. That New York City started being this, like, safe place, you know, Friends and Seinfeld. And it was like people just go there out of college just because it was fun. Whereas like when I moved there in 89, 90, it was just like, “Oh man, you’re moving to New York City. Okay, well, I’m really worried about you.” It would be like somebody moving to, I don’t know, Israel right now. Yeah. Everybody was really concerned why I’d be doing such a thing.
Flynn
And what motivated you to do it? What is it that you were seeking out?
Derek Sivers
Music business. I wanted to be a famous musician. It was the right choice for me. I mean, okay, look, it wasn’t the most dangerous place on Earth. It wasn’t South Sudan, you know. It was still the the co-hub of the entertainment entertainment industry. You know, New York City and L.A. were just the place where everything happens. And just so many great things in my life happened because I was in that place that attracts so many ambitious creators. There’s so many things that just happen if you’re just living in the same place as somebody else that you don’t quite get if you’re in Iowa but ambitious and you think, “Hey, it’s fine, we got the internet.” But sometimes there’s just that thing of being literally sitting in the room with somebody or a friend of a friend or, you know, hanging in person, kicking it in somebody’s living room, and that’s the vice president of a record label or the guy that produced this amazing album. And just being in the physical place where things are happening is still, I think it’s still key.
Flynn
You were seeking that out. You knew that that’s what you wanted. You wanted to be in in physical space, within proximity to other people who were ambitious.
Derek Sivers
Yeah. Well, I mean, but also don’t forget, like I’m talking 1990 before the internet. So it wasn’t like this decision of how important is the proximity. The decision was do you want to go get famous or not? So if you do--
Flynn
It’s binary.
Derek Sivers
Well then you move to New York City or L.A., maybe Nashville, where these things happen. Because if you don’t, you just won’t get successful.
Flynn
That’s really interesting, that’s really not that long ago. Where if you want to be famous, if you want to be successful in terms of a lot of eyeballs being on you, you only really have two options, maybe three options, whereas anyone can do that from anywhere right now.
Derek Sivers
Yeah. I wonder, I’m biased because of the past, but I’m still occasionally surprised when I hear that, like Mr. Beast was doing his thing from North Carolina or wherever he’s from. And I think, yeah, maybe location really is completely moot now. But still, there’s a thing about finding other ambitious people that maybe there’s some locations, you know, if you live in Moldova, where your location would be really working against you, and you might want to get out of a pessimistic place where everybody around you is saying like, “What are you doing? It’s just a waste of time. Stop it.” You know. That might rub off on you even the slightest bit. Maybe somebody from Moldova would at least just want to get to Berlin or something I don’t know. To be around some other ambitious people. I don’t know.
Flynn
You speaking about this reminds me of something that I noticed when I moved to San Diego, it was during Covid. And I remember at the time there was a lot of people that were moving to San Diego at the time. And, you know what it’s like when you move into a new place. You’re extra ambitious, you have extra energy. You’re seeking to put yourself into novel experiences to meet people. So I’m part of this sort of wave, this new influx of people who are moving to San Diego. And it’s not just people who are moving to San Diego, but they’re the type of people who chose to change something about their lives during Covid, which is a very specific type of person. There are also the type of people during Covid who, these are the words that are available to me right now, but I’ll just say exacerbate existing dysfunction. And then those who chose to create something new. You like that wording?
Derek Sivers
Wait hold on wait, wait, can you do those three again? I love, by the way, the setup where you said, “Sorry these are the words I have available to me right now.” I was expecting you to say something like, fucking fuck, fuck, you know? But instead you’re like, exacerbated. What? What did you just say?
Flynn
Exacerbate existing dysfunction?
Derek Sivers
Ah, okay. Sorry. Now that I’ve gotten past the words, now I got to the meaning. Okay.
Flynn
Yeah, yeah, you got the meaning. Yeah and that’s why I said sorry. Because that’s an annoying way to say something. I could say more simply. And I just didn’t have the words for it at the time.
Derek Sivers
Got it.
Flynn
Right. So there’s this migration that happens to Southern California or I guess, San Diego, but it’s also at a very specific time. And this specific time creates or I guess doesn’t create categories of people. But categories of people emerge in this particular time. And that was really interesting. I’m like, wow, I’m among a group of people who chose to move to Southern California in 2020, in the middle of Covid. That’s a very specific type of person and a very interesting creative energy. And I wonder if you’ve ever had experiences like that, where there was a particular time where you show up in a place and it’s specific to that time.
Derek Sivers
Oh good question. San Francisco, Silicon Valley 1999.
Flynn
Yes, yes.
Derek Sivers
Napster, the first Napster, Winamp. I mean, sorry, I’m catching like old people like internet 1.0 shit now. But oh man, the first illegal Napster and my company CD Baby was just like the toast of the town for the independent music business at the time where there was this alternate MP3 revolution going on, it was like the Indy revolution. I just happened to be in the right place at the right time. I mean, I wasn’t living in San Francisco. I was in Woodstock, New York, and then Portland, Oregon. So I was outside of it, but I kept going into San Francisco, where I’d be in the midst of these things there. Yeah, that was a really special time. There’s so many people, sorry not so many. There are some people that I meet now that we have that thing in common. You know, like the guy that invented Bittorrent. And you know Bram Cohen and Justin Frankel that wrote Winamp, which was like the very first Windows MP3 player back when Mac, nobody had Macs. Everything was Windows and he wrote the first MP3 player that was popular on Windows. And you know, sitting in a hot tub with that guy in San Jose and just feeling like I’m in the middle of everything, you know, going into the Napster offices in Silicon Valley when they were trying to become legit. Yeah. Anyway, I guess that’s my example. It was like right there in the midst of the MP3 revolution of 1999.
Flynn
Okay. So this is interesting. So now two very cool things I know about you. You go to New York City pre massive wave of gentrification in New York City. And then you end up spending a lot of time in Silicon Valley right at the right time. You’re an early adopter of location.
Derek Sivers
I was and then in 2012 I had a kid I was living in Singapore at the time, had a baby. And then I assumed that he was going to grow up in Singapore. We were legal residents and everything. Actually permanent residents of Singapore at the time. So I assumed, all right, this is where he’s going to grow up. Which means in the year 2030, he’ll be doing his military duty for two years and then forevermore until he’s 50. But, hey, he’s going to grow up here in Singapore, so that’s that. But then when he was about eight, nine months old, I thought, wait a second. I think kids need, like, their hands in the mud, you know, feet in the river, nature, real physical world. Not just apartments and shopping malls. So I thought, well, ideally he’d grow up in New Zealand. I mean, fuck, that’s just paradise. So let’s see, what would it take. So I was like, okay, here’s the forms. All right. Fill out the forms. So it was about nine months of paperwork. I became a legal--
Flynn
New Zealand just popped into your mind as a great option?
Derek Sivers
I mean, I had visited and I just felt like it’s just the nicest place on earth. And there’s something else to it. I’ll get to that in a second. But yeah, I did nine months of paperwork, became a legal resident. Mostly for the reason of him, so that he could grow up here. And I’ve been here really since then I moved to England for a year, but then Covid sent us back. But been here since 2012 and will probably be here until 2030 when he’s 18. So that’ll be the longest I’ve ever lived anywhere in my life. To answer your question, when you said, like, you know, just because. There’s also the nice benefit that if you live in New Zealand for five years, they’ll make you a citizen. And so then you have another passport. And you and I talked right before we hit record about how I burned the ships and renounced my US citizenship as a way of preventing myself from going back to my comfort zone. So, yes, I wanted another good citizenship. And so New Zealand ticked all those boxes, and now it’s my home in every single way. I’ve completely internalized it. It’s the only place I think of as home.
Flynn
It’s amazing. I’m so happy for you and and so happy for your kid. Did you get to grow up with hands in the mud and feet in the water?
Derek Sivers
Oh yeah very much so, yeah. His friends are video game addicts, but he is not. He really grew up in tide pools and forests and fields, and he grew up entirely outside, very deliberately. So now his definition of fun, even at the age of 12, is to go out and play outside, which I love. Apparently it’s rare now.
Flynn
It is rare. I do think that it is rare. That’s amazing. As I’m listening to you speak about this, it brings up for me one of the major questions that I wanted to ask you about. So in your book, “Useful Not True” which I love, by the way. And funny little note, you know those experiences in life where you have a particular lens or a particular way of seeing something, and you think that it’s an original lens, and then you find out a bunch of other people are using the same lens. That’s what happened to me when I found your book.
Derek Sivers
Oh, cool.
Flynn
Yeah. That thinking about beliefs as tools that either are associated with empowerment or disempowerment is something that I’ve enjoyed experimenting with for a while, and it was very soothing and beautiful for me to see that you have applied a similar thing for a long time, and that it’s worked out pretty well for you.
Derek Sivers
Well sorry before the question. I’m just curious, do you know where that came from for you?
Flynn
That’s a really, really good question. So I’ve heard you speak about CBT and and like the cognitive behavioral therapy stuff that’s kind of what I’m talking about here. It’s similar. I was interestingly in my therapy training and training afterwards like kind of anti CBT for a while. I’ve mellowed out since then. And more pro somatic, pro somatic CBT doesn’t get to the truth of reality, bypasses somatic experiences, all that kind of stuff. But over time, I have come to appreciate a more cognitive lens. I don’t know exactly where it came from. Maybe it came from learning about CBT stuff in grad school, maybe before then. I’m not sure. But I did start to see beliefs as tools about five years ago, but I don’t know the origin. I don’t know where it came from.
Derek Sivers
Okay, see, you and I have a very different background then that I didn’t learn about CBT until two years ago, even though I’ve been doing it for 30 years.
Flynn
I love that.
Derek Sivers
So I just heard the term only because somebody said, “Oh, it sounds like you’re talking about cognitive behavioral therapy.” And I finally went and looked it up and got CBT for dummies. Literally I read that book and then a few others. Yeah, “Cognitive Behavioral Therapy for dummies”. I always start with the dummies books. You know, like, I wanted to learn about religion. I got Judaism for dummies, Islam for dummies, Hinduism for dummies.
Flynn
Which is hilariously a really smart thing to do.
Derek Sivers
Thank you.
Flynn
Just to be a dummy.
Derek Sivers
Yeah, yeah. I mean, all right, I don’t know anything. Not going to pretend. So yeah, it was only when I was learning about it. I went, “Oh, this is kind of like what I’ve been doing since I was a teenager, and I’m 54 now.” So I think I’ve always been journaling, challenging my thoughts, trying to disprove them, coming up with conflicting evidence against them, etc.. But anyway, that’s interesting I didn’t know you went to school for that.
Flynn
Studied applied psychology. Yeah I studied applied psychology and my relationship with thoughts. I guess I started to really think about thoughts as something to even think about, probably at about 18, starting doing the thing that 18 to early 20 year old white males do, like going down the path of eastern like religion, you know what I mean? And what’s really interesting to me about what you’re saying is that at a young age, how old were you when you started to see your thoughts as something worthy of challenging?
Derek Sivers
19.
Flynn
Okay. Okay. So similar age actually, it’s pretty fascinating that at 19 years old, you recognized thoughts as something to be challenged or something to be disproven. Whereas so many people are so enmeshed with their thinking that it doesn’t even occur that they are something that could be challenged or disproven. So yeah how do you think that happened for you? How were you able to separate yourself from thoughts enough to recognize that there is something to play with there?
Derek Sivers
I’ve got an embarrassingly short answer. Is this hot woman that was my boss at the circus. I was a circus MC ring leader. My boss was hot and she was a fan of Tony Robbins. And she said, “You have to read this book called Awaken the Giant Within. It’s great.” So because I admired her so much and she knew me so well, I devoured that book. When somebody gives you your highest recommendation, when somebody says like, “Oh, Flynn, you know, I know you and you need this.” And if it’s somebody you really respect, you give it your full attention. So I gave that Tony Robbins book, “Awaken the Giant Within” my full attention at age 19, because my hot boss told me to.
Flynn
Yeah
Derek Sivers
And yeah sorry thinking about the hot boss for a second. And so in there yeah, of course, he talks all about that. It’s really that. So that’s where it started for me, there’s my short answer. Is reading that as somebody who was 19 years old and wanted to be a successful musician, I tapped into self-help stuff because I thought, all right, well, this is what’s going to help me be successful. Like the kind of success I was pursuing was not like, get a good job and climb the political ranks in your law office. It was very much a do it yourself. This is all up to you. The only thing holding you back from success is your own mind. Even choices like to move to New York City or what to do on a day to day basis. Who I meet, what I pursue, who I call, what I persist with, my plan of attack. All of that was just mental structure. And so getting into this stuff at 19 completely changed my life. And it wasn’t just that I read the book once at 19, I devoured all of his stuff, all of his Power Talk episodes and his other books. And I tried attending one of his events once, and I hated the in-person event. It was awful.
Flynn
What do you think about it?
Derek Sivers
Oh, God dude, I mean, okay, there are some people on earth who like this shit, but oh, man, this whole kind of like. “All right, everybody go rub the shoulders of the person next to you. Now pump your fist in the air and say, yes, I can.” I mean, I went, “Oh fuck no.” Like, no, just give me the book. Like, maybe I’m just an introvert. Maybe I don’t need to dance in between each point I’m learning.
Flynn
Yeah. Like to fully integrate the point, you have to pair it with excitement.
Derek Sivers
Yeah, yeah. Oh, God. That just turned me off completely. Yeah. I hated it, hated it. It was funny even 20 years later, I thought maybe I should give it another shot. You know, it’s been 20 years since then, and I tried again. I was like, “Oh, God.” And luckily there’s like a money back guarantee. So, you know, 12 hours into it, I was like, “No, no, no, I need my money back. I hate this.”
Flynn
I love that you I love that you hate that. That actually helps me accept myself a little bit more deeply because I have a strong aversion to those sorts of things. Wait you know, those experiences where you’re you’re part of a group dynamic and you can see the dynamic play out as if everyone is following some rules that don’t seem to be connected with what they actually want. They’re just following the rules in order to do the thing that the group dynamic would do. You know what I’m saying? But that might not be true. I might just be like a cynical asshole who’s being judgmental, you know what I mean? But there does seem to be a large section of the population who does like that kind of stuff. Who wants to be at the Tony Robbins experience, like dancing in between each thing that they learn. I don’t know. Do you have that experience where you feel removed from group dynamics like that, like you’re watching them happen rather than being able to fully immerse?
Derek Sivers
Totally. Which is why I have not yet been to Burning Man. And I was completely opposed because I think I would have that same repulsion against it. But just two months ago, I met a guy who told me what’s beautiful and wonderful about Burning Man, and he told it to me in such a way that I’ve started to think, “Well, maybe.” Because Flynn, my greatest joy in life, is overcoming or reversing personal prejudice. And 2023 for me was one of the best years of my life. Because I went to United Arab Emirates for the first time. Just because it was the layover, I was trying to get from New Zealand to Switzerland to a conference that had me come speak, and there was going to be a change of planes in Dubai on the way there. So I thought, you know, Dubai is a place that I hate, even though I’ve never been there and I know nothing about it. But just from what I’ve heard about it, I hate it in a pre-judging kind of way. So I thought I should look into that. I’m going to change this into just a three day layover. And sorry, y’all, I’m gonna make myself stop because I could talk for an hour about how much I love Dubai and United Arab Emirates and that whole culture.
Derek Sivers
I ended up reading a few books, probably maybe six books about it now. It is such a fascinating place. It is the most multicultural place I’ve ever felt. Like okay, you know, growing up in New York City, New York City is about 35% foreign born population. Dubai or United Arab Emirates in general is 90% to 95% foreign born population. Like everybody’s from everywhere, it is the best melting pot I have ever found on earth. It is the bar in Star Wars. It’s the place where everybody from around the universe gathers. And it’s just such a fascinating place. No, glitz, glam, bling, whatever you call it. You know, I’m not on Instagram. I’m not into that stuff. It exists there. So what, you just don’t go there. The rest of it is amazing. I love it so much. And that felt so good to me to reverse a prejudice like that. And then for nerdy reasons again, that we won’t go into, I was always prejudice against the Python programming language, because I’m fluent in a language that’s very similar to it.
Derek Sivers
Ruby. Which it’s like Ruby and Python are like Spanish and Portuguese. And so I never wanted to learn Python. And anytime somebody would talk about Python, my ears would close. I was prejudice against it. And then last year, I was looking at starting a new project, and I was trying to figure out what was the best language to do it in. And I sat there and evaluated like 17 different languages. And I thought, “Well, I think that’s every language I could look at doing.” So I was like, “Oh, huh. Well, I haven’t looked at Python. I guess just for the sake of completion, I should look into Python.” You know, prejudice, prejudice. And so I got a book on Python. I started looking into one. I went, “Oh my God, this is gorgeous. Whoa, this is fascinating.” I was like, “Oh my God, this is a beautiful language. Why have I been prejudiced against it all these years?” You know, kind of like Arab culture. What the hell? I guess I grew up in America at a time when we were told that Arab is synonymous with terrorist. And I guess I accidentally internalized that. What the hell? I was so wrong.
Flynn
You took it in as your own, took it in as if it was your identity that you chose to have. But it was, but it was just something that was given to you.
Derek Sivers
Oh, I think it was just completely blow. It was just unconscious
Flynn
Blow, yeah.
Derek Sivers
I just assumed it was a fact, you know?
Flynn
Assumed it was a fact. Yeah, yeah.
Derek Sivers
Yeah. You just assume that tomatoes are a vegetable. And somebody says, “Actually they’re a fruit.” And you go, “What? No.” Okay so, yeah. So that was that was 2023 for me. At the end of the year I was thinking, “God, what a good year it was.” I was like, “Why am I so happy with this year?” I was like, “Because I reversed two prejudices and how good that felt.” And so who knows, maybe I will end up enjoying Burning Man someday.
Flynn
Maybe.
Derek Sivers
A Tony Robbins event, no. That’s not prejudging. I tried a couple times to give that an open mind, but no, I just still hate it.
Flynn
That was peri judge and post judge and it stayed for 20 years.
Derek Sivers
Whoa peri.
Flynn
So yeah, I know the word peri from perinatal, which is something like a way of saying during pregnancy. Pre, peri, post and I love using peri.
Derek Sivers
Do you have kids?
Flynn
No. I don’t remember how I learned perinatal. Have you ever had an experience where you’ve had a prejudice, you’ve prejudged something and you’ve chosen to move towards it and you’ve moved towards it, and then you decided that you still hate it.
Derek Sivers
That’s a good question. Olives. I still hate olives. Coffee mostly. Actually, oh, God. Whoa, dude, you just helped me realize 2023 was the first time in my life that I drank a cup of coffee and didn’t hate it, and it’s because it was Emirati coffee. My Emirati friend his grandfather built the very first building in Dubai. That’s how young that place is. And he served me a cup of coffee and I said, “Oh, no, I don’t drink coffee.” He said, “No, my friend, it’s Emirati coffee.” I said, “No, I hate coffee. I’ve always hated coffee. I’ve tried it a few times.” Even my girlfriend at the time, we were out at a coffee shop and she took a sip. She was like, “Oh my God.” She’s like, “This is the best coffee I’ve ever had.” She’s like, “Derek, I know you hate coffee. If you’re ever going to try coffee, try this one. This is the best coffee I’ve had in my whole life.” I took a sip. I was like, ‘Ah, oh, God, that’s nasty. Awful, I hate it.” She said, “Okay, you just hate coffee.” So that was the year before, that was 2022, 2023, I’m sitting in Dubai meeting with this dude. Such a nice guy. Mohammed Kazim, his whose grandfather built the first building in Dubai.
Derek Sivers
And he serves me a coffee. And he said, “My friend here, it’s Emirati coffee. You must.” And I went, “Now I’m going to be a rude asshole if I don’t.” So I was like, “All right.” I was like, “Oh, wow. Wow, this is really good.” He’s like, “Yes, that’s Emirati coffee. That’s the good stuff.” And it’s different. It’s like a cross between tea and coffee. So when I tell this to people, they usually go, “Oh, is this the one that’s made in the sand?” No, that’s Turkish coffee. In his opinion, he said there’s only 3 or 4 places in all of Dubai that make proper Emirati coffee. So coffee drinkers, next time you’re in Dubai, ask somebody where you can get real traditional Emirati coffee. Give it a try, and then email me to tell me how different it was. So yeah, so three things or three prejudices I steered towards in 2023 and did like them. But yeah, the only one I can think of that was prejudiced against, tried it again, still didn’t like it. Probably olives. Yeah, that’s a fun question. I’ll probably think of another in a couple of days.
Flynn
Yeah, you may have to think about that for a little while. So when I brought up your book, one of the questions that I had while asking it, this is sort of a general existential question that I have is, okay, well, how do we cultivate conviction about our goals? So you’re saying, you know, like take a look at your thought and be discerning about the usefulness of your thoughts. See if your thought or your interpretation is either helping to empower you to achieve something that you want to achieve, or disempowering you to achieve that thing. It’s making it harder to achieve the thing that you want. So with your son, for instance, you had the goal of having him grow up in a place where he could have his hands in the mud and feet in the water. Like, how were you convicted enough about that because another option could be growing up in Singapore. And that’s one thing, I could totally see someone being convicted about that goal, that that’s the right thing. So how were you convicted enough about that to move to a different country to raise him there?
Derek Sivers
Well, maybe two answers. For one like for your listeners that are just in general thinking like, how can I adopt a conviction. I’m going to give a real example that we can probably all relate to. Whereas say you’ve got a deadline, something that really has to be done, whether in 12 hours or 12 days or 12 hours is better and you’ve been too distracted and oh my God, you’ve basically got 14 hours of work to do and you’ve got only 12 hours to do it in. But you’ve got other things that are tempting you. You know, a friend says, “Come on, come out. I’m going to treat you to the best ice cream ever made.” Or hey, this person that you have a big crush on, she’s right here and wants to meet you. You’d have to tell yourself, like, no, I need to do this. I need to stay focused. It’s the only way this is going to get done. What you’re saying in that moment is, I need to believe this is the most important thing in the world right now more than anything else. And so you do this internally. You kind of quickly update your beliefs to say, “No, this is the most important thing. Everything else can wait. I am deciding to think this way right now because that’s what I need to believe in order to get this done.” Okay, we can all relate to that scenario. So it applies in other ways too. Losing weight, getting good at something, you deliberately change your values to say, “Yes, I love ice cream. But I am not going to eat ice cream. Because being thin feels better than eating ice cream or nothing tastes as good as being fit feels.”
Flynn
I think that’s what the saying is. Yes.
Derek Sivers
So you deliberately change your values in a very conscious way, because you need to do that to make this change happen. So we can do this with other things too. You can look at yourself and realize that you have a tendency to talk too much about yourself in social situations. And you can feel the pain of it when you maybe see somebody else doing it to you and talking way too much about themselves, and you go, “Ooh, shit, that sucks. And I think I do that too. I need to stop doing that.” And so you might tell yourself, either you could say, I’m just gonna shut up in social situations, I’m just gonna bite my tongue and say nothing. But then you realize that that makes you a boring guest, too. So instead you say, I think I need to deliberately get better at asking the other person about themselves. I’m going to learn how to do this. I’m going to maybe read a book on it, giving me some supporting ideas on how I can deliberately turn questions back at the person who asked them. Deliberately ask people for more information about themselves or say things like, “Oh, really? Like what?” You know, when they say something and you do that because you think, I need to make this change.
Derek Sivers
So I need to update my beliefs that this is more important. Okay so there’s some day to day examples but I feel I should answer your question before we dive into this. You asked me a two part question that was like, how did I do that for my son, deciding it was important enough to grow up in New Zealand.
Flynn
Yes.
Derek Sivers
I don’t know if that wasn’t a decision as much as an observation that he was seven months old, crawling on the floor in apartment buildings in Singapore. And whereas I think that Singapore is also one of the most multicultural places and would be a great place to grow up as a teenager, I think in short, I just felt like this would be a great place for him to grow up in general. But then when I saw him crawling on the floor, I went, “Oh God, I forgot about the importance.” Like to me, my soul would feel lacking if I didn’t have that connection with like, creeks and tadpoles and long grass blowing in the wind and the feeling of bark and climbing trees and mud and all that stuff, I was like, God, that’s such an important part of being a kid.
Derek Sivers
At least it was to me. And I think that’s kind of a human experience. Like, I know he’s going to grow up in a very computerized world, but even, you know, 3D animations and motion graphics are trying to imitate the physics of the world. But if you learned the physics of the world through a computer screen, more than actually being in the world and sticking your finger in a rushing river and watching how the water flows around it, I was like, I want him to have the real experience of that, not just a computer experience of that. Like, no, this is really important to me. I really want my kid to grow up in nature. It was intended to only be for a few years. It wasn’t intended to be his entire childhood, but maybe I just felt that-- yeah, I know it’s not a concrete, absolute universal truth, but to me I felt like, no, this is a really important thing for childhood. So I just decided it was important enough to move.
Flynn
It felt true to you. I really like that you mentioned something about your soul. Like almost like you have access or at least in this instance, you have access to some sort of innate truth in your soul, and you decided to listen to it. I find that to be really beautiful. I find that to be--
Derek Sivers
I don’t know what that is.
Flynn
Yeah. It’s just such a strange thing because I would really like to believe and I don’t know if this is true or not, but I’d really like to believe - I guess I can choose what belief I have. I’d actually like to hear your perspective on it that everyone has access to that. I’ve certainly heard that before - that everyone has access to listening, to being connected with the innate truth of their soul and then making choices that are informed by the truth of their soul. I’d really, really like to believe that.
Derek Sivers
I disagree because I know too many people or people in too many situations where what they feel is their inner soul is telling them some nasty, fucking damaging shit. “That person wronged you and you need to get revenge. Like. No, everything in my soul is telling me I need to get revenge. Even if I end up in jail because of it. That motherfucker is going down because he wronged me.” And I think even in those situations where I’ve had open, safe conversations with people in those situations. And I said, like, “Come on, that’s some shit you’re inheriting from your parents, or that’s some value system that you’re putting there that doesn’t exist in nature.” But no, they’re just so convinced in the moment. Like, “No, you know, show me two lions on the field and that lion, you know, attack that like you know, what the other lion is going to do is kill that motherfucker. That’s the law of the jungle, man.”
Derek Sivers
You know, it’s like some people internalize this stuff so deeply. Just from who their friends and family were growing up or the media they took in. That it just feels like an absolute truth. It’s the same people say about their religion you know that people’s religion feels like an absolute truth. Like, what are you talking about? This isn’t just in my mind. This is the way the universe works. But then you if they were to explain that to somebody that grew up on the other side of the world, never having heard of this religion, and you tried to explain it to them, the other person says, “Well, I don’t know. I’m 60 years old and grew up. I’ve never heard of that. So you’re telling me this is an absolute truth, the way the world works? But we’ve never heard of that over here, so I don’t think that’s true.” So these things feel like absolute fact. And so I think that soul searching can feel like going into your-- God maybe that’s just synonymous for your deepest beliefs.
Flynn
Like soul searching is synonymous with your deepest beliefs. Please say more about that.
Derek Sivers
Ah, I just made it up.
Derek Sivers
But sure we could riff on this. There are some beliefs that are new. You heard them on a podcast last week. You go, “Huh? That’s a good idea.” And there’s some that you’ve just been swimming in since before you were born. You know, your great grandparents and grandparents and parents and all of your friends and family growing up tell you that this is how things are and you see them act that way, and the media you take in is that way. And you’ve just shaped your entire understanding of the world. And so it’s like so core to how you see the world. Then I’d call that a deep belief, that’s not easily dislodged. And probably when you’re soul searching, what we call soul searching might be another way of saying bypass the nouveaux beliefs. Let’s get to the oldest ones. What is true about you? What is your essence? You know, it’s really probably just going back to what’s the oldest shit you learned? Which still might be shit.
Flynn
It’s a question that I ask is like, we make the distinction between soul and nature and then cultural conditioning as if soul is the correct thing. And conditioning is generally the incorrect thing, you know?
Derek Sivers
Yes.
Flynn
And even actually in the way that you responded to that when you said you disagree, kind of in your response was, well, no, that can’t be soul because it’s malevolent and some people want to hurt people. And then I was thinking, well, what if souls want to hurt people sometimes? Like, how do we know that shit? You know, like, how do we--
Derek Sivers
Well that’s where I go to my radical skepticism, basically nihilism, which I think has a bad rep, but I think it can be a great thing, which means blank slate. Nothing has any inherent meaning. It’s a blank slate. You might have grown up with other people putting meanings on to things for you, but none of that is true. It’s a blank slate. Nothing has inherent meaning. You put meaning into whatever you want. If you feel like it for the sake of a purpose, you know, making you finish your paper in 12 hours, you’re projecting some meaning to help that happen. But then he nature is a funny one because I used to not believe in nature. I used to think everything was nurture. But then I got two kittens at four weeks old that had never been more than a foot apart their whole life, and they had such radically different natures, even though they were treated exactly the same and their nature stayed the same for their whole life. One was so adventurous and malleable, and you could just pick her up and do anything. The other was so timid her whole life. I went, “Oh wow.” I treated them exactly the same and yet they stayed. You could tell, like when I first met them when they were four weeks old. Little tiny kitten babies.
Derek Sivers
You could see their personality already. And I think that’s nature. And you ask any parent who has more than one kid that sometimes just two kids will just have radically different natures. Actually in the next room right now, I just last week, at the request of my son, got two pet rats.
Flynn
Yes.
Derek Sivers
We just got them, a few weeks old, and already they have very different natures. One is super cuddly and lazy and just wants to cuddle in your lap, and the other one’s super adventurous. So, anyway, sorry, pet rats are way cuter than you’d expect. Especially growing up in New York City where I thought rats were going to be--- go to YouTube sometime and search for “cuddly pet rats” and just look at how cute and cuddly they are. They’re pocket puppies. They just want to sit in your lap and cuddle. Anyway they’re adorable. Nature. Yes, there is a nature and we don’t even need to pass judgment that killing is bad. There are some situations where killing is good and it’s the right thing to do. So it helps to have an open mind and look at these things, with a clear head, and try to remove all judgment before you put it back deliberately.
Flynn
I like that a lot. So in the time when you thought that everything was determined by nurture, do you have an intended function for that belief at the time? Do you remember what you were using that belief for?
Derek Sivers
No, I think that was just my assumption. I just assumed that’s how the world works. Is that everybody we all got it from somewhere that if somebody’s angry, they must have been taught to be angry. If somebody’s really passive and gentle, they must have been taught to be passive and gentle. But then you find out through experience, I don’t know. Okay. There are some things that are just nature.
Flynn
Which is in some ways I can see how that can be a hopeful perspective. Oh, if it’s all nurture and someone is angry and they learned this anger in this lifetime, and there’s not something like true about the identity of their essence or their soul that they’re angry, then we might be able to rehabilitate that or redirect that pattern,
Derek Sivers
Right! Or change it.
Flynn
Or change it. Change it is a better way of saying it. Yeah.
Derek Sivers
Yes, I’ve had the difficult experience of being in romantic, very entangled relationships with people that have a very different nature than I do. And for years I thought that nature could change to be more compatible with me and no.
Flynn
Okay, one thing that people struggle with a lot in what you’re describing there in those relationships. Is how did you know, in those relationships that enough had been enough? What was the experience that let you know, okay, this person is this way and they’re not going to change, which means that I have to go a different direction.
Derek Sivers
Well, I’ll give you a very concrete example. That’s my most recent example, which ties into the other stuff we were talking about, CBT. Is I journal every day, I didn’t start doing this till I was 42. I journaled since I was a teenager, but usually only when something was perplexing me and I needed to sort out my thoughts. Then I would turn to a journal and say, okay, what am I thinking? What is this? What am I trying to get out? What’s going on? But unfortunately, then if I look back at years of those journals, it’s like weeks of silence and then me turning to the page in troubled times, it doesn’t really give me an accurate look back at what my life was like during those times, because it could have been, you know, 13 days of peace and on day 14, turmoil. So I regretted that. At age 42, when my kid was born, I was wondering what were my 20s really like, but I had no way of telling, and I had no accurate record. So I thought, well, you know, the best time to plant a tree 20 years ago, the next best time now. So I was like, all right, I’m starting now, every day I’m going to journal. Just saying what I did today, how I felt, what I did and how I felt at very least that. Even if it’s just ten minutes at the end of the day to quickly say, did this. Did that feeling like this, had this thought, you know, in ten minutes, sometimes I’ll take an hour, but at least just ten minutes at the end of the day.
Derek Sivers
So worth it. I highly recommend this to anybody. There are very few things that I say I think everybody should do this. I think everybody should do this. Everybody should journal, even if it’s just into a voice recorder or a camera, I mean a video feed. So good to have that to look back at. And here’s a concrete example which also answers your question, which is I had been seeing this wonderful woman for two years. We moved in together. We bought a house together, we got engaged, we were planning on having kids, and we were having a difficult time. We were fighting a lot, but I had remembered that things had been really good, but were just difficult right now. But then they were really difficult, like just screaming and butting heads at everything. So I said, I need a few days apart. And I got an Airbnb and I went away for a few days. And what I did is I went back and reread every single diary entry since the day I met her and those things are honest because they’re you know, for my eyes only. I’m always honest. And they’re written in the day.
Derek Sivers
So I trust the day’s report more than I trust my memories weeks or months later. And so when I went back and looked at those journals, I had usually not been happy even the day I met her. Even like those early times. It had always been hard, so I had been wrongly remembering it as good in the past and difficult in the present. It had been difficult the whole way.
Flynn
Wow.
Derek Sivers
And after two years of that, and as we were planning on having kids, I thought, “I think this is a bad idea. I don’t think I should be having kids with somebody that we’ve always had a hard time. I don’t think this is going to be changing anytime soon.” So I did the very difficult but lucid thing of telling her, I think we need to break up. So that was a year ago and it was because of my journal and it was the right thing to do. I’m so, so glad I did that. She’s a wonderful person. I miss her occasionally, but it was the right thing to do. We were not a good mix. Our life values were too different. What she wants out of life and what I want out of life we’re just too different and just clashing every day. But I wouldn’t have realized that if not for the journal.
Flynn
There are so many beautiful gems in there. You journal only when things are intense, so it’s this skewed representation of what life is. Then you decide to journal every day so you can get an accurately capture the truth of what you’re experiencing. You get into a relationship. Think you start to hit some turmoil, the way that you’re interpreting it is things were great, but now they just took a turn. They’re not so great right now, which was probably an interpretation that would allow you to continue staying in the relationship. And if you weren’t able to go back and see the accurate reports, you would have been able to continue with that interpretation. That would have you stay in the relationship for longer. Then you got the accurate reports. The accurate reports were like, oh no, this has never been as good as I thought it was going to be. It’s probably the right time to leave. That’s amazing.
Derek Sivers
Thanks. It was very helpful for me.
Flynn
Yeah. That’s amazing. And I’m really glad it’s obvious. I mean, you spoke to how difficult it is. It’s such a difficult thing to have that break up conversation. I think it’s really cool that you did that, that you chose your happiness.
Derek Sivers
That break up conversation was actually easier than most because I felt so solid about it, because I could tell this wasn’t a decision coming from a current mood. This was me looking at, you know, 800 days of us having been together and I reread 800 entries. And so I felt very solid that was the right decision. Whereas when couples break up because they just had a fight or I’m mad at you right now or you really pissed me off yesterday, maybe we should break up. That’s a hard conversation to have because you don’t know if you’re being stupid or impulsive. But to look back at 800 days together and say, no, this is usually been bad. I felt very sure about that decision.
Flynn
I’m thinking about the people listening to this who are unsure about their relationship or considering breaking up who haven’t been journaling for 800 days in a row, and that saying, “The best time to plant a tree is 20 years ago, and the second best time is now.” Is such a good saying. I usually write every day, I would say that I write six out of seven days on average. But I honestly don’t-- I’m not recording all that often how I’m doing. I only record how I’m doing when I’m confused or frustrated or upset. I’m usually writing about ideas, and you have inspired me to start keeping an accurate report of how I’m actually doing my levels of happiness.
Derek Sivers
Cool. I find it so useful for other things, even as a life log, I can say what day was it that I flew to Israel? You know what when did I meet Christine? Or even oh, man, there’s a friend that I only talked to, like, once or twice a year. And I know that six months ago, she told me that she met this new guy and that things are going great and told me his name. I’ve totally forgotten his name. I went and searched my diary for her name, and I found the last time we talked where she said or I wrote in my diary, “She’s met this new guy named Louis.”
Flynn
That’s incredible.
Derek Sivers
And I was like, ah, I know I’m going to be talking to her tonight. I was like, Louis, Louis! I was like, I got to ask how Louis is doing because I put it in my diary that day six months ago. There’s no other way I would have remembered that. But she was so happy that I asked about Louis. Yeah life log. It’s great.
Flynn
This is like, maybe the most practical question that I’ve asked you and I actually really enjoy being in the space of non practicality. How do you organize your journals? My sense is that you’re a very organized person. You asked for the audio clip of this to keep in your archives. No one has ever asked that before. I love that energy so much. So what is your system and your process for organizing all of your journals?
Derek Sivers
Well, first, everything’s on a computer. My phone is ephemeral. There’s nothing of importance on my phone. I erase it every week, I don’t care. Anything of value gets put into my computer, and then even then, I’ve got, like, a four terabyte drive that has everything. I just took a little time up front to put things into categories that make them easy to find in the future. So there’s a folder called audio, and inside that is like audiobooks, language, music, me or something like that. And so then inside music is maybe 200 folders of albums sorted by artists. So I don’t have a Spotify subscription. If there’s an album I like or music I like, I keep it and I put it in the category by the artist name. So then if I ever want to go listen to Miles Davis, even if I’m sitting in a cabin in Patagonia offline, I can pull up my folder of Miles Davis and hit play. By the way so I should just say first, I remember the day that I organized my music. I remember I was sitting in Union Square in my apartment, and it was like a 15 hour day, and it was monotonous and boring, but I did it, like I organized everything by file name, by artist name, and I put it into the right place.
Derek Sivers
And I’m so thankful that I just took a little upfront time to put things in an organized way where I can always find them. So if there’s a brand new album out or some new music I’m putting into my collection, I already have a system in place. I know put it in the music audio, music, artist name, put the mp3’s in there. So same with the diary. I used to have my diaries scattered around in like word documents called diary.doc, you know. And eventually it’s like that file grew so long with dates and entries, which were sometimes I’d guess, what the day was and I’d have to search by date. So then I said, okay, this is going to be a little boring. I’m going to do this once and for all. So now the system is folder called diary. And then every file name is just year dash month day day.
Flynn
So year year year year dash.
Derek Sivers
So the file name like yeah 2024-05- 28.txt. Is the diary for May 28th, 2024. And I just ended up creating a shortcut. So all I do is I type the letter D in my terminal when I type D enter. It automatically grabs today’s date and creates a new file or opens the existing file at today’s date.txt in the diary folder and I just start typing. Maybe I just got off a really interesting phone call and I’ll just go to my terminal on the computer and I hit D bloop new text document and I’ll just start typing like, “Just got off a really interesting phone call with la la la la la la la la la la la la la la.” I’ll just type for, like a few minutes, save the file, get back to work. And I go through my day. I do my thing and it’s the end of the day. And before going to bed, I’ll be like, winding down, about to shut off the computer. I’ll just type D and I’ll say, “Had an interesting podcast with Flynn Skidmore this morning. We talked about something. It was good. Cuddled the two rats. Oh, my God, they’re so cute. They slept in my lap. Things are going well. I did my weight lifting today. I did a good walk. Feeling good. Almost done with my next book.”
Derek Sivers
Save ten minutes. But also, you know, sometimes I’m really. Okay, so that’s the gist of it. That’s the short answer. That I would recommend to anybody. Just keep a daily diary like that. Then if there are some subjects you keep coming back to like for years. A few years into living in New Zealand, there was a huge family decision about should we move back to Singapore after we have New Zealand citizenship or should we stay here or should we move somewhere else? It was a massive decision that we had hundreds of conversations about, and so eventually I made a folder called Singapore where every time I have new thoughts about Singapore. I would type D Singapore which would open inside diary Singapore now would do you know, whatever 2019-02-22 the year month date of today’s .txt for my current thoughts today about Singapore. Also, I spent years wondering if I should get a dog or not. The pros and cons. And so I had a folder called dog with my ongoing thoughts about today, about whether I should have a dog or not, or the pros and cons.
Derek Sivers
And so then when I’m trying to make a decision, I can look back at all of my years of thoughts on the subject of whether I should get a dog or not, or some are ambiguous, thoughts on relationships. I have a folder that’s called relationships. I have one called home. What does home mean to me? This is something I’ve thought about a lot for years, and so whenever I’m having more interesting thoughts about what home means to me, I type D space home. And now I start just typing my thoughts on home, even if it’s just a quick momentary thought. Or maybe I’ll sit there for an hour thinking about home and it’s so useful then, maybe years later, I’m trying to make a decision on whether to maybe sell my only home and go fully nomadic, or have one home. Or maybe I need two homes on the opposite sides of the earth, I don’t know, I’ll go back and I’ll reread my last ten years of thoughts on the subject of home all in one place. So useful. And it takes almost no work to set this up. You know, you just set up a folder where you’re just going to keep all those thoughts. And so yeah.
Flynn
That’s one of the coolest things that I’ve ever heard. That way of organizing thoughts is so incredibly foreign to me and so incredibly attractive to me. It sounds like your mind is a wonderful place to be. I’m sure it’s crazy a lot of the time, but it sounds amazing in there.
Derek Sivers
Well, I think I just saw the value after years. How old are you now?
Flynn
34.
Derek Sivers
Okay yeah. So I’m 19 years older than you. So I just saw the value over time of my thoughts over time. Seeing what’s persisted versus what disappeared can be so interesting to know about yourself. One of my oldest friends, just recently, when I had a day where I did one task all day long, I woke up at 5:30 in the morning and I set myself on, like programming this thing that I was programming, and I did it all the way from 5:30 in the morning until 11:00 at night, however many hours that is, 17 something. And then she called at 11:00 at night and I was like, “Hey, I’m about to go to bed.” I said, “I just had the best day ever. I just did this one thing all day long. I didn’t even leave the house. I was just so focused on this one thing all day long. I almost forgot to eat.” I said, “It was the most beautiful day.” And she said, “Derek, I’ve known you almost 20 years now.” She said, “The happiest times in your life are these days.” She said, “You’ve told me this exact thing over and over and over again for almost 20 years. Every time you have a day where you do one thing all day long, I’ve never heard you so happy.” She said, “It’s one of the most consistent things about you. You change your mind on everything else, you know, dogs, Singapore, home.” But she said, “One of the most consistent things about you is you love having a day where you do one thing all day.” I was like, “Wow, that’s a good insight.” And I think it’s really helpful to know this about yourself. What persists over time versus what’s just my mood right now. And I think a long term journal is so good for looking at your past to see what has persisted.
Flynn
That’s really it’s so beautiful that I don’t even have words. There are so many thoughts that I have on that. That I am going to journal about tonight in my organized system. I love that level of self study, and I love that level of truth that can be revealed over time. I love emotions, I think that one of one of the things that I’ve kind of heard you speak about with emotions here that we all humans in general, tend to kind of bastardize emotions when we think the lens through which we’re seeing the world or ourselves colored by an emotion, speaks to truth. So it could be like, I wake up today and I’m in a really good mood, just happened to be in a great mood today, I think, “Oh my God, my life is going really well. I’m good. I don’t need to change anything.” But I don’t have something to measure that with. I really might be setting myself up for danger. And then the next day or two days later, I could wake up in a really bad mood, or in a different scenario, I could wake up in a really bad mood and say, “My life is absolutely atrocious right now.” But if I were to look at the data, I would see that, oh, actually, things are going really well. When we can have the data that you’re speaking about, where truths of patterns are revealed over time. What I think it does is rather than thinking that our emotional lens speaks to the truth about reality, it allows us to fully experience the emotion without some sort of fear of it meaning something, or using it as a way of avoiding the fear of something. You know what I’m saying? It seems like you’re setting yourself up-- by almost operating as a computer in terms of how you’re organizing things. You’re setting yourself up to be very beautifully human in terms of your emotional experiences, maybe. You didn’t say that’s something I’m making up, but.
Derek Sivers
Thank you. I like that lens.
Flynn
Before we wrap up, anything that feels important that you’d like to share?
Derek Sivers
No, I was going to say the same thing to you. Like, I feel like a couple times you brought up the slightest thing and I’m like, “Oh, yeah, let’s talk about this. Hey, New York City neighborhoods.” So I want to see, was there anything that you wanted to ask that we didn’t get a chance to because I kept taking tangents.
Flynn
I enjoyed that so much, there’s nothing that’s popping into my mind currently as shit, I wanted to ask that or oh, God, you interrupted me. I didn’t get that. Nothing at all. I feel very clean and happy.
Derek Sivers
All right, well, anybody listening to this, go to my website and send me an email. It’s the reason I do podcasts like this is because I really like the people that I meet because of it, I get emails from strangers every day and I answer every single email, and it’s honestly one of my favorite hours of the day is getting emails from strangers across the world that introduce themselves. So yeah, go to my website, sive.rs my last name with a dot in it, and you’ll see the link there to email me. And please do and say hello.
Flynn
And we’ll link your website in the in the show notes. Thank you so much for being on. I really appreciate getting to talk to you.
Derek Sivers
Fun conversation. Thank you. See you.