46: Nicole Seah (Nix) - Loving What is Real

[00:00] Everything that you make, whether it's company, a piece of writing, a podcast, is this amalgamation of your experiences in the world. Grow up, all the things you read, all of the people you've met, it's a collection of these things. Brought into the furnace of something and come out the other side. You really see in this very subtle moment is how a person's entire being has gone into this. Any of these very large, significant companies. You can actually trace back the lineage and the sense of effable feeling that it's come from the founder. [00:30] or come into friction with one another. I don't know if you've read the short story Borges and I. It's about him and having a separate writer self and then himself circling around each other. And, you know, one wins, but who is it? And there's always these dueling parts of me, which is one of this very serious, intense side and then this more playful light side. So the implication there is that it should be bridged. Is some separation good? Maybe. I don't have answers here. It's through seriousness that you find playfulness. Think about Miyazaki, right? He hand drew his frames until well into the 70s. There's this one amazing interview where he says, [01:00] I was thinking about how to make the dragon move. And he's like, I actually went to a restaurant and I looked at the eels wriggling around. And I thought, you ever seen an eel move like that? He just has like constitutionally unable to not care. And I think that is what makes this film so light. And you don't have to have this tyranny of one identity. Welcome to Dialectic, episode 46 with Nicole Sayah. Nicole is a writer, investor. [01:20] and a friend who I've had many wide-ranging generative conversations with, and so I was excited to be able to capture one of them with you here today. Nicole, or Nyx, as you might know her from her writing, writes on Substack at Starting From Nyx,

[01:34] and just launched a new project called New Ontologies, where she's profiling founders and early stage teams and the principles and ideas and craft and humanity [01:43] that go into them. [01:44] We talked about beauty, reality and fantasy, writing and ambition, and this tension that we circle through so much of the conversation around, which is striving and seriousness and effort and intensity, and also the ways that... [01:59] Things can just fall into place when you come to love not just fantasy but reality. [02:05] I hope you enjoy the conversation. And before we get into things, I'd like to thank Notion Dialectics presenting partner. Notion is a creative workspace for your life's work and has dramatically changed in the past couple of years as they've rebuilt the company from the ground up to think about how AI can be used in a way that doesn't just automate away your teammates or automate away the meaningful work, but instead allows you to think from first principles about how you can collaborate with people and with AI to do great work. The theme behind this for Notion [02:35] together. As Notion has reinvented itself, the team has evolved incredibly too. My friend and former podcast guest Brie Wolfson and her collaborator Camille wrote an amazing piece for Colossus about the inside of Notion and how they're becoming an AI first company. And Notion is growing incredibly fast. I have to imagine that there are a number of dialectic listeners who would be amazing fits for Notion, whether it be on the product side, the go-to-market and sales

[03:05] cross-collaboration with AI, and a team that I spent a lot of time with, the storytelling team, as they think about the future of Notion's brand, how Notion can tell amazing stories about people building inside and outside of software across creativity, and how teams, big and small, are thinking together. [03:20] If you think that might be you and you're interested in working with Notion, please reach out either to them directly or to me at work at jacksondoll.com and I'll take a look. It would be a true honor to have some of my audience join the team at Notion and get to collaborate together. Notion is a huge part of what makes dialectic possible. You can also learn more about Notion or check it out if you haven't tried it in a while at notion.com slash dialectic. Thanks again to Notion. And here is my conversation with Nicole Sayah. [03:49] Nicole Sayah, thank you for joining me. This is a long time coming. Yeah, I'm excited to be here. I'm excited for this. We've had many long meandering walks and conversations, so I'm excited to hopefully capture a little bit of that. [04:02] uh, in, in hi-fi. Um, I want to start with beauty. [04:06] I'm going to turn around a line of yours on you. [04:10] How has pursuing beauty rearranged your life? [04:14] Hmm. Yeah, I think a lot about that quote by Iris Murdoch, which says that beauty is a version of unselfing. And I've always loved that term of basically beauty taking you out of yourself. And I think one part that's interesting. [04:33] One way beauty has rearranged my life is through reading beautiful works of literature. I think just the...

[04:39] sentence-by-sentence construction is really... [04:44] gorgeous to me. I read a lot of... [04:47] translation as well. And I think that seeing the choices that the translator makes, but also the choices the author makes in parallel is something I draw a lot of inspiration from. [04:58] I like that. You have a [05:00] amazing piece on kind of like different types of beauty. And I want to get into the details on that, but I have a couple of excerpts first. [05:08] And you start the point almost in this sort of like, I don't want to say it's a negative orientation, but a complicated orientation to beauty. You say, only later I reflect on the sheer inescapability of my longing for beauty. Most women I know grew up haunted by the beauty myth, torn between acceptance and aspiration. [05:24] All my life, I saw beauty as a form of applied effort. Beauty was rarely a quality one owned intrinsically, rather something one maniacally expended money and time to become. I think this is also against the backdrop of a trip to soul, which is obviously a very specific place in that world. Then you go on to say, it seems to me there are two predominant types of beauty. A beauty that is solipsistic, oriented around glamour and draws us inward in an ever-turning gyre. And a beauty that lies outside of us, that makes us more generous and open. [05:54] Murdoch reference you were talking about. [05:58] I'm curious how you relate to this sort of like, maybe one cut of this or one interpretation I have is like, there's a type of beauty... [06:05] as like a target... [06:07] Like to make something more beautiful, make oneself more beautiful, but certainly also...

[06:11] effortfully make words more beautiful or a podcast more beautiful, whatever. And then there's a beauty as like perception. [06:18] which is like this just generous orientation towards recognizing the world is beautiful and, [06:23] Um... [06:26] Do you think that those two things are... [06:29] at odds with each other and, and to the extent they're not, or to the extent they, or like, [06:34] Maybe what I'm asking is like, [06:35] how do you think about intentionality in those two forms of beauty? One, cause the second one, the perception one feels much more like, like, [06:44] I'm not doing anything and the world's just happening to me and I'm perceiving the world as beautiful and the other feels like very effortful and we'll talk more about that and seriousness and so on. But does that distinction make any sense? I'm curious for your perspective. Yeah, it does. But I mean, I think I would say that both are actually quite intentional because the second is more like actually, oh, I'm... [07:01] purposefully paying attention to the world. And it's a frame of mind where I think a lot about like ordinary magic. And, you know, there's a lot of poets that write about this. And some of my favorite poetry is always like about regular people, regular days. And I think one aspect of beauty is actually noticing the ordinary and watching it [07:22] come alive with a new sheen. [07:24] You know, there's that Simone whale, like attention is the greatest form of prayer. So, [07:29] I think they're both intentional, just maybe different frames. One is very inward oriented and the other is more external, which is I'm. [07:37] perceiving the world, I'm taking in these inputs, and I'm making something out of that, or I'm

[07:42] or I'm anticipating or understanding something different about the world. [07:46] Does it take effort? Does that type of attention take effort? Do you relate to it taking effort? [07:52] I do, yeah. I mean, I do think that, well, sometimes it's like, oh, wow, this mountain range or this thing that I'm looking at, it's just inherently, you know, nature is beautiful. Yes. But I do think that some... [08:05] perception is required, like some perceptual change is required for you to also see the regular world as beautiful. [08:13] Yeah. [08:13] There's a... [08:15] uh, Nietzsche idea that you get into in the same piece. And it's almost like a, if that's like one form of two types of beauty, there's a different kind of caught on two types of beauty being sort of like easy to perceive and difficult to perceive. Um, and Nietzsche is talking about music and like the way that some things are like really easy to consume or really easy to access. He says, um, [08:36] We need to exercise effort and goodwill in order to endure it in spite of its strangeness. We are finally recompensed for our goodwill, our patience, reasonableness, and gentleness towards what is unfamiliar. By the unfamiliar slowly throwing off its veil and presenting itself to us as a new ineffable beauty. That is its thanks for our hospitality. Love, too, has to be learned. Yeah. [09:05] there's [09:06] Someone else you say tolerates strangeness long enough to be changed by it. [09:12] And I think this is also maybe you in the same piece. You talk about perhaps developing a taste for difficult beauty or the ability to tolerate mental discomfort is one of the most important human skills to have, to consume novel things, to accept boredom and sadness, to be patient, to override the aversion of being changed.

[09:27] And so like, there's this... [09:28] I'm really fascinated by this like [09:32] this tension around something being strange and having to sit with it to the point where the beauty inside of that in it becoming beautiful, we are also changed. [09:43] Like... [09:44] Which I think I've experienced, but it's so non-intuitive. [09:50] Yeah, I mean, I think it's like the frontier of the world coming together and the unfolding that happens between you and the world, which I think we've talked about a bunch. [10:00] you know, there's lots of ways that, for example, Nisha talks about music. There's another piece by Zadie Smith that I really like called, you know, Attunement, or On Attunement. And it's about how she hears Joni Mitchell's song, California, for the first time. And if you've heard California, it's a little bit of an odd song. It's not, you know, it's not naturally, it's sort of a different register, a different tempo than people maybe were used to or are used to. And she describes, you know, [10:27] a moment underneath a cathedral when she hears a song and it completely flips for her. And it's about context and it's about engagement with the song in a very difficult moment in her life or a moment of reflection. And I think about that a lot for books and different types of media as well, which is, and even people, right? It's like context matters so much. And I think sometimes

[10:57] Maybe you see something or read something once and it doesn't hit then. But I think it requires patience and endurance to actually... [11:05] look at it again, like turn over the stone again and give things second chances. I think I'm a big believer in that. [11:13] That's a romantic idea and a beautiful one, and certainly one that I think most people will connect to. Maybe it's not quite the same example. I had my own experience of that with Joni where I... [11:21] I already liked Joni, but I had heard Both Sides Now many times. And I just want to walk one day and I fully listened to it for the first time. And I was like, oh, my gosh, this is one of the best things I've ever written, which is a little different than I think the Zadie example where she actually had almost an aversion to it. Like an aversion, yeah. [11:37] I guess my question is like, [11:39] Thank you. [11:40] We have finite attention. [11:42] Um... [11:44] Maybe the classic example is you read a book or you watch a film and you don't connect with it, and years later you come back. And so time is doing a lot of work there. Perhaps to go back to the point you were making or the point I was making or referencing of yours is that, [11:57] I've changed. How do you know... [12:01] When to like. [12:02] give something more... Assuming that some beauty is not easy... [12:07] How do you know when to persist? [12:09] When it's challenging. Versus numb or something? Or dual? Yeah, we're sort of neutral. I think the dispassion thing is probably the signal that maybe there's nothing there. But I think if you feel that there's something there and maybe it's uncomfortable. It's abrasive. Yeah, it's abrasive. And you're like, oh, I don't like this at all.

[12:30] then maybe return to it because there's some emotional register there that you're not quite aware of. [12:36] Yeah. [12:36] Are there any experiences, maybe art-wise or otherwise, that come to mind where you've had this kind of like switch, almost like this horseshoeing? [12:45] Yeah, there's actually a really great example. I took art history in college and I [12:52] My art teacher, she was just, I mean, a fabulous professor, but she was very moved by art to the point where she would cry in the middle of our lectures. It was great. Like, I was so energized by it, first of all. But there was this one, you know, structure. Is it a big class? It's a small class, like a seminar. But there's this big structure called Donald Judd's Boxes in Marfa. And it's just like a row of boxes in the fields of like a waste, like a barren land. [13:22] basically. And she started like bawling her eyes on in the center of class and [13:26] For a long time, I didn't understand it. You know, I was kind of shocked by that reaction. [13:33] Or almost like it's like, come on. Like, are you really? But when I... [13:39] There was like a moment where I looked at some photos of those boxes and there's some, the sun was setting, the light was reflecting off of it. I read the backstory of, you know, why did Donald Judd kind of put those boxes there? It's about like man-made versus artificial and all these interesting dualities. And I thought there was just so much more texture there that I didn't pick up the first time. And so it...

[14:00] changed my mind, first of all, to see someone have a really emotional reaction to it. And I also think that's why we... [14:07] enjoy friends' recommendations or we trust people to show us what also hits for them. [14:16] Maybe you can kind of adjust your view that way as well. [14:19] I wonder about this because... [14:21] And it relates to something else we'll talk about, but [14:24] I know a movie you like a lot is The Boy and the Heron. [14:27] And it's a good example of a phenomenon that I've had many times, which is I'll experience something. The first time I saw it, I think I saw it, uh, the dub maybe, um, uh, [14:38] So which is maybe a slightly different experience, although Robert Pattinson was really going for it as the bird. [14:43] And I was like, I love Miyazaki, but I really don't know what was going on there. And then I read this amazing review by David Ehrlich, who's a film critic, and then I watched The Wind Rises. [14:53] And so like... [14:54] I guess the point I'm trying to illustrate is I got to... [14:59] without additional context from other people, I may have watched The Boy and the Heron years later and connected it. But instead, I watched the sub two weeks after reading this review and a few other things, and then I really connected to it and really loved it. And I had this complicated relationship, where I'm like, am I cheating? Is the fact that I needed somebody else's additional context, I needed somebody to show me how to see [15:18] Mmm. [15:19] I wonder how you relate... Versus there's maybe a... [15:24] When it happens on your own, whether it's on a long time horizon or just from a [15:28] I don't know, you're going to stand in front of a painting for 10 minutes until you cry, or whatever, it's more earned? Am I just in my head about that? Well, I don't think, I don't know, I don't really think about a sort of instinct as anything earned. I think it's earned to also spend time and engage. I mean, honestly, engaging could mean, oh, staring at something for 10 minutes, or it can mean talking to people. I think of attention much more as a communal thing, or, um,

[15:55] Learning is a communal thing. And I think, you know, for a long time, I thought of it as a very hyper individualistic thing. [16:02] endeavor. And now I'm much more open to the fact that, oh, hey, when I want to understand something, or I want to learn a new concept, it's always through community. It's always through hyperlocal experiences of that thing. So I would say I think that's also earned. Maybe I'm like clinging to some sense of like needing originality or something. Right. Yeah. [16:23] Hmm. [16:24] Or even... [16:26] To go back to your communal idea, it would feel more valid, dare I use that word, to like... [16:33] I'm going to talk with a few of my friends who all saw... [16:35] The Boy and the Heron. But if I outsource an opinion from a professional, very serious person, critic, it again feels... Maybe a better way of asking this question would be... [16:47] When you're doing this communally, how do you maintain sort of a sense of... [16:52] your own interiority, your own sense of self or ideas versus the risk maybe of like, [16:59] Um... [17:00] anything you consume quickly trying to like, [17:03] make your, you're thinking on that very relational is you, you don't get this aspect of sort of sitting, like going through something on your own. Like, do you have a relationship to maybe it's, maybe you're oscillating, which is you're going to go, I don't know, use a simple example. Like you, you read a novel or you read a book. [17:21] and then you spend some time thinking about it, and then you go to the book club, and then you journal. It does feel that some amount of

[17:28] Maybe that's what I'm trying to understand or work through is like you want some of the relational and you want some of the isolated. Yeah. Yeah. [17:33] and you don't want to overly rotate to one, and maybe I'm wondering about how those two things blur together. [17:40] Right. Well, I mean, the danger point is if you actually don't feel anything toward a particular person, [17:45] piece of work. But because everyone tells you you should feel something, you've like, sort of labeled it as meaningful. Whereas, you know, [17:54] if you come to that thing and you still feel something and you've also talked to a bunch of other people, I think that's still a genuine appreciation of the work. [18:01] Yeah, it reminds me of, I talked to Celine Wynn, who I think you know, or at least have read, and it reminds me of how she talks about Proust, which is like, a different cut on this would be like, you don't have to like this for some arbitrary reason that you're supposed to like it. But also somebody like Celine being like, this is fun and gossipy or whatever, might be a portal in for your own. Yeah, it's a really, I really love the idea that attention is actually just like about doing, like, well, I almost said doing the work, putting in the time. Mm-hmm. [18:31] Yeah, I love Celine's work and I think an important part about what she's doing is like sort of expanding the market. [18:39] for literature through her perception and her, you know, [18:45] her sharing her perspective on things. And I do think that's very powerful to go back to what we're saying, which is like, okay, maybe you do need someone to guide you. And there's nothing wrong with being guided sometimes as well. Right. I think I take away a lot of the, I don't have any shame to like where I come to things, how I

[19:02] get to things. It's always, how do I feel about this thing at the end of the day? And have I learned something along the way about myself, about the world? And I think that's a much more honest and meaningful way to come at it. There's also like less ownership. There's so much less ownership and less pressure, you know? Yeah. It kind of comes back to this idea that like... [19:20] the most beautiful things. What I love about that early idea is that, [19:24] It actually relates a little bit. I talked with Henry Carlson about introspection. And he has this Nick Cave example. And he basically talks about pushing ourselves to introspect with yourself as the subject, not as the object. [19:35] And it feels like beauty is something similar, which is not like... [19:38] who am I or how can I be beautiful or how can I like, it's just like, what am I noticing? And when you take that orientation, part of what I'm sensing in a lot of your answers is just this like very outwardly directed, [19:49] orientation. [19:51] that thus is less concerned about whether it's your idea or somebody else's idea or any of these things. Yeah, exactly. [19:58] I like that. [19:59] So there's maybe a related idea to beauty, which is... [20:05] you write about fantasy and reality. [20:08] - Mm. [20:08] Um, [20:10] and maybe the ways that we cling to fantasy when in fact reality is actually like far more rich or real or beautiful. A couple of quick excerpts. [20:20] But the characters that have captured my heart the most always chose to return to or see reality for how it was. And love the deeply flawed human world because it was real, not contrived, not airless or soundless or unbruised. It was real and had violence and rapture and bodies that aged and buildings that crumbled. But by that same hand, fervor, courage and human striving. And then a couple other ideas.

[20:50] That what lasts, what feels right, looks nothing like what I first imagined or dreamed about. There are no more fantasies to cling on to. There is no past, no backward place for my longings. Only forward into the night, led by the beacon of beauty. Which is a really, really sweet sentiment. [21:07] Um... [21:08] Maybe a really almost sillily open-ended question, but how have you learned to love what is real? [21:14] Hmm. Yeah, it's such a such a great question. And I think I was referring to a lot of different novels in that in that writing about one of my favorite sort of character arcs is like young man kind of, you know, goes for glory and and and victory and goes and embarks on this insane quest. [21:44] and live reality. And I'm always really interested in that inflection where you see something and you think it's real, but you realize it's a mirage. Or it wasn't what you hoped for. It wasn't what you hoped for. [22:03] are not coming true, but I can actually chart a new path and actually opens you up to new, um, [22:10] aperture of thinking. I think in particular, when I think about that novel or these sets of novels, I think, [22:20] Fiction is always a really interesting, very extreme version of reality, which is...

[22:28] Maybe we don't go on the quest, right? We don't go on this insane quest to Wild West and all these things. But we do go on these little quests and we hope and we dream for things. And there's some really fundamental truth to the fact that we don't always get what we want. Yes. Um... [22:43] - The texture of the story is deeply real. - Exactly, yeah, exactly. And the other thing is when I think about everything that I love and care about, whether it's, you know, a beautiful piece of work or it's a person, it's always actually the moments where they chafe against the edge of reality that I realize that they're human and they're flawed and I'm also human and flawed. And that makes it deeply relatable. [23:10] And, and so when I reflect on everything that's happened in my life, all of the actually really good moments unfolded in ways that I didn't anticipate for, didn't plan for and, and [23:23] maybe didn't even have the imagination for, which, you know, I think is really beautiful. [23:29] How do you know when you're actually encountering reality? [23:33] Like, um... [23:34] Much of modern life... [23:38] We sort of live like a bubble-wrapped existence in some sense, at least in terms of reality, in terms of stake. We don't face death very often. It's a very extreme example. [23:48] and [23:48] Obviously, there are times in life where you really get slapped in the face. You have something you desperately want and you don't get it or you lose or whatever. You have the job you want. Like... [23:58] But I think in a lot of the cases it's like a little more subtle.

[24:01] Mm. [24:02] Does that feel true to you or does it feel like you're kind of, or maybe it's only true in hindsight. Like I definitely find like, [24:08] There are, again, there are the glass shattering moments, but a lot of time it's like I realize like a year later or something. Yeah, I think they're both. I think it's both. I mean, I think there are moments where you're just really shell shocked or you're there's moments where you're really let down by something, someone or you just didn't get that. You didn't get the thing you wanted. [24:29] where it's only with time passing that you kind of reflect back and be like, okay, I didn't get what I wanted, but I got something far better. Um, [24:37] I think having that mindset is important. [24:42] Prior to the past four years, I think I had a very rigid mindset of, or I'm a big planning personality. Prior to the... [24:49] Until four years ago. Yeah, maybe four or five years ago. Whenever I started writing. Writing publicly. Writing publicly. I had a very big planning personality. [24:59] process is actually me learning how to not plan for things and be surprised by the unexpected. [25:07] Is that, I was going to ask, like, what is your strategy of... [25:10] introducing more reality? Is it that? Is it just not planning? Because that's almost a passive openness to reality. But maybe there's probably another orientation. It's like, how do I... I don't know, it's the Henrik line, make contact with reality. Yeah, make contact with the world and make it yield something. Yeah, how do you do that?

[25:44] Perhaps there was some truth in them. Perhaps there was something I have yet to learn and have to incorporate into the work to make it better. [25:53] And so having sort of an intellectual honesty as well is really important. Well, and that often relies on... [26:00] Like you have to externalize it to [26:02] be totally intellectually honest sometimes. Yes. Like it's very hard to realize... [26:08] You're in the fantasy world. Right. It's not good thinking alone, you know. Right. [26:13] Back to the boy and the heron. You so well... [26:16] You make such an excellent point. That's what that film is about, basically. The dreamland is pretty appealing. It's almost like, why are you leaving? I think it's really easy to lull myself into... [26:33] believing my fantasies. [26:35] Unless I'm forced, like... [26:38] And I don't know, one example is I've been fortunate to have friends who are like, [26:41] smack you across the face. [26:46] There's a, you alluded to it earlier, there's a David White quote I think we both quite like a lot. He says, whatever human being desires for themselves will not come about exactly as they first imagined it or first laid it out in their minds. What always happens to the meaning between what you desire from your world [27:00] and what the world desires of you. [27:02] It's this frontier where you overhear yourself and you overhear the world. [27:06] Maybe this relates to the notion you were pointing out of... [27:09] I think it's changed maybe four or five years ago with the writing, but, uh, [27:13] You had said it's important, referencing that, I think. It's important to overhear the world rather than narrate it in advance. And there's an element of the planning thing about that.

[27:24] Again, this is back to the more subtle part of it. [27:28] Um... [27:30] What does it feel like to like overhear the world? [27:32] Yeah, well, maybe this is a naive or innocent point of view, but I do see the world as sort of benevolent. And sort of narrating it internally in your head actually closes you off to any sort of external information or external redirection or any sort of feedback. And I think it's always dangerous when you close yourself off to feedback or you live in like a sealed chamber. [28:02] talk to people, and even when you're getting bad feedback, it's actually kind of benevolent. Like, people are telling you, you know, that something's not registering, something's not working, and... [28:14] Yeah, I remember this moment in art class. I used to paint a lot. We can talk about that. But before I wrote, and I used to paint acrylics, and my art teacher came up behind me and [28:25] I was like, oh, you know, this painting, it could be so much richer and deeper if you had these different, if you added these different colors to it. And I was like, great, let me just try it out. And the art teacher came to me later and said, you're the least defensive person ever. [28:41] I've met. Like you just are like ready to try things out. And I'm not sure if it's going to work out, but. [28:47] you were ready to put new colors on the painting. And I always think about that line of like putting new colors on the painting as a framework.

[28:55] which I think to view the world. Are you that way with things outside of painting? [29:00] Or with writing? Yeah, I think so. Yeah. Huh. What do you think that does that come from that experience? Like what were you? Have you always been like that? [29:08] Yeah, maybe it's a sense of egolessness. It's not necessarily true that I have no ego, but I think everyone does if we're honest to ourselves. But I think trying the best to be... [29:22] So egoless in the pursuit of beauty or in pursuit of craft, I think, is very important. And you have to balance that with sort of your opinionation about what you should be doing as well, of course. Yeah. [29:35] There are some aspect of like, okay, don't take yourself too seriously sometimes. [29:40] Yeah. [29:41] As I was doing a prep for this, I was finding myself kind of continuing to swing on this pendulum. And I think this is starting to get at it, which is... [29:48] What you just said... [29:50] Thank you. [29:52] has this lightness and this almost like Zen-like quality of just like, go back to like the reality is better than fantasy and I should just be really, really open to it and I should be loose and egoless. And yet you are, [30:06] are a person who, and certainly someone who writes about intensity and deep effort and seriousness. There's a bit where you say... [30:16] Uh, beauty is effort. Effort is monstrous and ugly, but it also is the source of everything beautiful in this world. And then somewhere else in writing and in life, you need to gnaw on the bone. This kind of goes back to the reality thing, meaning get under the skin, get into the crevices. Writing has become bloodless and fake, but people create the real. And so,

[30:34] Am I making up this tension? No, there's definitely a tension. [30:39] But, like, you're, like, that story about the painter, like, that would, people who don't know you very well would be like, wow, Nicola must just be, like, so, like, la-di-da, kind of, like, very vibes-based, like... [30:51] Um... [30:52] and we'll talk more about this later, but in some sense, you have a creative life. [30:56] primarily in writing, that is probably a little bit more that way. But still, you write about [31:01] Timothee Chalamet and intensity and seriousness. And then you have a... [31:03] Professional life is an investor that's much harder. Maybe it's hard and soft. [31:09] Yeah, those two things seem so at odds. Yeah, well, I think that you put it really well, which is I have multiple identities. And the reason why they feel at odds is because sometimes those identities conflict or come into friction with one another. I don't know if you read the short story Borges and I. [31:27] No. Borges is an Argentinian writer. I think you'd really like his short story. And it's about him and having a separate writer self and then himself. And they're sort of like circling around each other. And one wins, but who is it? Wow. And I don't know. I read that and I really related because there is these two parts. And there's always these dueling parts of me, which is one of this very serious, intense side and then this more playful, light side. [31:57] disambiguating those identities has been really helpful to get at that, to separate out that tension as well. [32:03] Are you taking that on from almost like a persona sense? Yeah.

[32:08] I don't know, people talk about, when I'm writing, I'll take on a persona, or when I'm performing, I'll take on a persona. When I'm at work, do you feel that duality in your... [32:15] when you're at work versus when you're writing versus when you're in your, the rest of your life or is it a little bit subtler? I do feel the distinction. Yeah. And it's something I'm, I'm working to bridge. [32:26] And so the implication there is that it should be bridged. Like, is some separation good? Maybe. I mean, maybe. I don't have answers here. But yeah, I do think that there is, maybe you can successfully have them separate. And my personal endeavor is to bridge them slightly more. [32:45] Hmm. [32:46] Thank you. [32:46] Yeah, I think maybe... [32:48] not to try to attempt to answer my own question, but it does seem that both aspects of that for you [32:54] the playfulness and lightness and the, [32:57] intensity. [32:59] kind of are about loving what is real. [33:02] Like they're different. [33:04] Cuts on that, maybe? But they both are in service of that, it seems. Mm-hmm. Yeah, I think there's... [33:11] There are a bunch of books by the German author Hermann Hesse. [33:16] I love and all his books are about duality. If you read any of them, like Siddhartha, Glassbeard Dream, and Narcissus and Goldwyn. Narcissus and Goldwyn is probably the most relevant here, but it's about these two monks. One of them is very aesthetic and lives in the tower and becomes this really, you know, intellectual and teacher, professor of sorts. And the other is sort of this, you know, man of the world.

[33:42] goes into the world, engages in acts of sensuality and violence and all of these sort of raw things. [33:50] And at the end of the novel, they come back together and have a conversation. [33:53] And really, when I left that, when I read that novel, I was like, wow, like, this is us, like, this is everyone else. [34:00] This is me, first of all, and this is everyone I've ever known, which is there's one part of you that's in the tower and there's one part of you in the world. [34:07] And you're constantly dealing with between the two. Yes. And he doesn't pass any judgment as well. It's not like, oh, one is better than the other, but one is each is its own integral nature. And you have to fulfill your integral nature. [34:23] Maybe that's a non-answer, but... I love that answer. I'm probably stretching it, but it reminds me a little bit of My Dinner with Andre, if you've ever seen that film. I haven't. It's not quite the same, but it's a similar element of sort of duality and not... [34:37] It really doesn't seem that the director is... [34:40] taking too much of an opinion, which is maybe the critical part. [34:43] Yeah. And that certainly describes Siddhartha too. Um, [34:48] On the seriousness, kind of like effort, commitment thing... [34:53] You have a bit where you say, when you meet someone with devotion and care for their craft, they have thinner barriers between their soul and the external world. Their soul shines lightly on the surface of their being. [35:04] Again, I know I'm hitting this over and over again, but that duality is there again, which is like, [35:10] That's kind of a surprising description of a very serious person. Their soul shines lightly on the surface of their being. I think in that piece you're referencing Chalamet. This was a year ago or so when he was doing it. And I both agree with you, but it seems so... When you think of a seriousness, it's like...

[35:29] Yeah. Well, maybe my thesis is that maybe my thesis is my unspoken thesis is that it is through seriousness that you find playfulness or there is through seriousness that you find this level of, I guess, skating through the world. You know, like if you think about Miyazaki, right, I write about Miyazaki a lot and I care a lot about his work and he's a great inspiration to me. [35:59] available and there's this one amazing interview where he says like I was thinking about how to make the dragon move. [36:06] And he's like, I actually went to a restaurant and I looked at the eels wriggling around and I thought... [36:11] You ever seen an eel move like that? It's amazing. And he's just constitutionally unable to not care. And I think that is what makes his film so light and beautiful. And when you watch a Miyazaki film, [36:25] It's got all these dualities inside of them, too. Right. There's all these children who have to grow up too early. There are these like wars and famines and fires and, you know, lost children and the like. But at the end of the movie, you come away feeling like, oh, that was a beautiful, playful, light movie. [36:43] expression of art. So I think maybe my [36:48] Maybe my thought is that there can be both. There always is both. [36:51] Thank you. [36:51] Thank you. [36:53] I think you're really... I've been wrestling with this a little bit, and it's come up in conversations where it's like... [36:58] where we had this moment maybe that circled around the figure skater, Alyssa Liu, and the whole thing was like,

[37:07] It's like... [37:08] Having, like, the intense person gets crushed by the person who's having fun. It's like Novak Djokovic. I like hitting the tennis ball. There's all these stories. I was just talking to Nick Thompson about this. [37:18] ultra runner uh killian jernay i think and he's like everybody's pissed because he's just having a blast out there right yeah [37:24] and [37:25] This also relates to like find the thing that feels like play to you that feels like work to everyone else. And I've had this conversation with a bunch of people in real life who are kind of like, but like how much of it should be like play? Should it be 20%? Should it be 60%? Do other people who it feels like a play to a hundred percent. And then meanwhile, may it's not true for all creatives, but certainly writers, you talk to writers, every writer's like, I hate writing, but also it's so excruciatingly meaningful. And so I'm like, [37:49] I really struggle with this is like, should it feel easier or should it feel intense and hard? Yeah. [37:54] And I think... [37:56] I think your answer is... [37:58] My sense is, to go back to Alyssa Liu, my sense is Alyssa... [38:02] is someone who is deeply serious. 100%. That doesn't mean it's toxic, but it also doesn't mean it's like, [38:09] All loosey-goosey, easy all the time. Right. But the expression of it is playful. Yes. Right? When you see her on ice, she's just clearly having so much fun. Maybe I'm projecting onto her. But also because she's done the work. She put in the work. Because she's done the work. And so then on ice, she can sort of relax in some ways because her body and her muscle memory is carrying her through that... [38:28] Peace. [38:29] Yeah. [38:30] Yeah, I mean, we could talk about this all day. The challenge, I guess, is like, I don't know if you've seen, have you seen Miyazaki and the Heron, the documentary they most recently made? And it's, I'm sure it's like any of them, like,

[38:40] He's amazing. There's a line in there where he's like, "If we don't create, there is nothing." But [38:47] I don't think he's having fun. Like, he is deeply burdened. [38:51] And so I think people usually swing to one way or the other. And that's like the thing that my sense is you were right. I think Alyssa Liu on the ice for the Olympic gold was really, truly like living it present in it. Maybe that's specific to a performer or whatever. [39:07] And yet... [39:09] I think she did the work on the interim. Maybe it's just getting to the point where you're able to put in all this intensity and then let yourself... [39:17] Like drop, drop the weights. [39:20] Yes, exactly. Well, it's there's this Joan Didion. I read the Joan Didion collected interviews last week. And one of the lines I saved in there was salvation comes from extreme and doomed commitments. And it's a banger. It's such a banger. But also like, you know, when and she's asked later, there's an interview where that line is said. And later the interviewer is like, oh, so you think it's a doomed commitment? She said, no, I think it's salvation. [39:47] She was talking about her marriage, right? Marriage, children, and writing. And so she's like, no, I think that's salvation, actually. But it's both. But it's both. It's both, right? It's a commitment. It's also salvation. [40:00] You were referencing that same bit, and you say, I've always related deeply to a romantic ethic. For a while, writing was a sort of long-haul dread, a seasickness that wouldn't abate even when I reached land.

[40:11] Do you still feel that way? [40:13] I... [40:14] I go in waves. I go in waves. I'm sure you feel that way too, but there are moments where writing just feels effortless and easy, and there are moments where I know that, oh, I have to dig and excavate something. [40:29] And it's going to require some level of concentration and effort. I'm currently writing a piece about Robert Caro and sort of power broker and also his process. And something I really admire, but I actually have to do the reading, which is, you know, man, it's a slog. But it's really meaningful. [40:53] Yeah. [40:53] Yeah, you have a... There's an old piece you wrote, I think quite old, about peaks and troughs. And I forget the specific phrasing you're using, but you're talking about it sort of just like, yeah, like I... [41:06] my first guest ever, the podcast, Jason Louie, he says, confidence in the memory is success. And I think there's an element of that. It's like knowing, I gotta do this log again, but I've been here before. I know what's good on the other side, which maybe makes it a little easier as you progress. Oh, yeah, totally. Do you find that [41:21] the amount of slug [41:23] is pretty constant or is it, are you getting lighter? Like, is it getting more and more easy? [41:28] over time. [41:28] It's getting easier to accept. Right. It's the paradigm. Yeah. [41:40] Oh, it's funny. It's really funny. Um,

[41:45] Thank you. [41:46] How has... [41:48] Again, very much on the same note. But how has, on the note of doomed commitments, like how has commitment... [41:55] to yourself, [41:56] to your writing. [41:57] Um... [41:59] Maybe on the note of sort of making yourself proud, like... [42:03] How have you used, actually, maybe a specific... [42:06] kind of silly reference that maybe captured what I'm getting at is, is, uh, you'd reference Murakami on his routine. And he says, the repetition itself becomes the important thing. It's a form of mesmerism. I mesmerize myself to reach a deeper state of mind. [42:21] Maybe it's a simple question about habits. Maybe it's a deeper question along the lines of what you're getting at, but how have you... You're someone who has... [42:27] You don't write professionally. [42:29] at least currently. [42:31] and you have a deep, deep [42:33] commitment to it without some kind of super, like you don't have, you don't write daily necessarily, you don't write weekly. And yet you seem to have a real commitment to that. [42:41] How does that happen? Is that, did it start with more scaffolding and now it's lighter? Yeah. [42:45] Does it still have a lot of scaffolding? [42:47] Yeah, I think it's part of my identity now. And I think that's how all change happens, where you integrate it into part of yourself or part of your identity. It's interesting because I've been writing online publicly for four years now. But I've been writing since I was maybe like 10 years old. And in lots of embarrassing outlets. You know, I was like, what, Pad, Blogspot, WordPress, Wix, like all of these weird Tumblr. You know, I was on all these weird Internet sites, like writing things.

[43:17] all these things. And so it's sort of a continuation of that younger child in me that was always writing. And I also wrote a pretty big poetry portfolio and thought poetry was the craft. And I still think that there are some poetic sensibilities in the writing, but they're not so condensed in form. But it is sort of a, how do you develop good faith, right, in other people? You develop good faith by trusting that another person is going to say what they're going to do [43:47] time and do the thing to the best of their ability. And I think that really applies to yourself, which is how do you have good faith in yourself is that you actually do the thing you're going to say you say you're going to do. I think that's been a big, you know, [44:01] contributor to... [44:03] continuing the writing because I've told myself I'm going to show up here and [44:08] I don't want to let myself down the way I wouldn't want to let a friend down. Do you have a relation to yourself with... [44:15] with most things, with only writing, with some things, [44:21] Multiple things. [44:23] Writing creativity, I'm quite serious about writing. [44:26] work as well as an investor. I'm also quite serious about fitness. So... [44:32] Maybe those three, yeah. [44:33] Creatively, you reference poetry in painting both. [44:36] are those kind of like moons circling the sun of writing? Or do things kind of come and go? Like, did you ever have that commitment level with painting or other things? [44:44] I tried. I think that there's only one really, maybe this is, you know...

[44:50] Maybe it's not true because there's been a lot of artists who are multidisciplinary. But I do think if you actually want to get really good at one particular medium, it benefits you to spend more time in that medium. And painting is just a very long time. [45:05] You need a lot of patients to paint a lot. [45:08] I mean, you need a lot of patience to write a lot, too. Yeah. So writing and painting, it's just like, okay, then I have time for nothing else in my life. Right. [45:18] You also, you wrote a recent piece, um... [45:21] kind of referencing this Michael Nielsen idea and this idea of [45:25] One of the questions I was thinking of as you were speaking is like, [45:29] Thank you. [45:30] The good thing about commitments and good faith is that at some point it stops being like a habit or something or something you're really trying to do and it starts to become an identity. I am someone who writes. [45:39] In this... [45:40] kind of piece in the, in the, in the, I think in some of what Michael's referencing, he's talking about sort of like the lightness of identity of a writer. Um, [45:48] Thank you. [45:49] You say, when you free yourself from what Nielsen calls the tyranny of writing as primary identity, you can be free to choose for yourself what kind of writing you want to do and surface your other multiple identities, scientist, researcher, investor, designer, founder. And then you say, instead, I chose the word sustaining creative aliveness because creative aliveness is the process of discovery, collection, synthesis, and then finally expression. [46:08] And so it's funny, like, [46:10] it seems like you do really have a deep [46:12] identity level commitment to being a writer, or being someone who writes maybe. And yet, it seems, maybe even now, and we'll talk about it in a little bit, like,

[46:22] as your kind of creative and professional lives are converging a little bit as you're like writing is sort of this deep identity thing. And it's this tool. Maybe, maybe the broader point here that I think you, you also get at is like, [46:36] Many people silo their creative lives and their professional lives. And writing maybe more so than painting is easier to do. [46:45] bring into other worlds. [46:48] But... [46:51] Yeah, it seems like you're holding this writing thing really, really firmly, but you're also not... [47:00] needing to [47:01] that it define who you, like the person you are, it's like, it's still a tool. [47:05] - Maybe the point that we keep circling back to is that, [47:10] I feel that it's fine to have multiple identities, and writing can be one of those identities, and in service of all these other identities. And you don't have to have this... [47:18] maybe as Michael Nielsen says, tyranny of one identity. I think when you silo yourself into one particular identity, be it, you know, maybe it's an investor, maybe it's a writer, whatever, then you actually close yourself off to all these other things that you're interested in. And it's actually fine to be, you know, multifaceted and multi-identity person. And, um, [47:39] And it's okay for that to be slightly illegible as well. [47:43] Hmm. [47:46] Hmm. [47:47] Do you think that we can form new identities or are we just like – is it more like –

[47:53] I'm [47:54] Harvesting or inventing? [47:58] That's a great question. Man, I don't know. I think it's harvesting. [48:03] Yeah. I think it's harvesting. I think things show up early. You know, I think things show up early. But we maybe neglect that you don't water that or whatever. Yeah, you don't water it. Right. I'm sure that there's a life in which I could have become a painter. [48:15] But... [48:16] I chose not to become a painter. [48:19] Does that life feel... [48:21] Totally gone. Lost to you? [48:23] No, I think at some point maybe I'll harvest that identity. Yeah. It'll be another one in my little box. Yeah, maybe that's an elegant sort of model for much of what we've been discussing, which is like there are all these sort of like seeds and things in your garden. Yeah. And you can like spend all your time, you can like... [48:38] build a big wall in the middle of the garden. You can just spend your time over here. You can kind of have two kind of core parts of the garden, [48:45] Um, you can go back to things and then maybe in the, in the sort of fullness of time and maturity, you eventually you like look around and you realize it's just one card. Yeah. I like that a lot. Yeah. Um, yeah, I, I appreciate you checking me on the, on the, I, I, clearly I'm, I'm, [49:02] I'm trying to force everything into one jumble instinctively or otherwise. [49:09] You... [49:11] maybe to talk about bringing things together, uh, [49:14] very recently, just yesterday, two days ago, launched the beginning of a new project, which I think is cool to see [49:22] at least an aspect of two parts of your identity come together, which is this, like, one, on one hand, like, historically a lot of your writing is, like, more poetic and personal and for a long time was even synonymous. And then you have this other life, which is, like, someone who's deeply committed to, like,

[49:39] on one hand, like technology startups, but I think really like, [49:42] Dreamer is building really impressive big things. You say, I enjoy the work I do with early students software because it's all about telling ambitious stories of technology, failure, reconstruction, and where fantasy confronts reality markets whilst casting a romantic hope for the future. [49:57] This is beautiful. I'd love to just hear about what... [50:01] what New Ontologies is, where it came from. We can talk a little bit about Ando II in a minute, but what is behind this, and how has it felt to find this bridging in parts of your life? [50:13] Yeah, well, in sort of the [50:16] tagline of Neo-Ampologies, the website, the tagline is, how do we have... [50:22] how do we talk more ambitiously about the future? And when I was reflecting on that tagline or reflecting on what this project is, I thought about it as... [50:31] How do we access ambition at different scales? And on one scale, and one way to talk about ambition is this really large moonshot vision of the future. How do we make reality malleable to our inventions? How do we, you know, that quote, which is like, the world is just a museum of passion projects. How do we make those projects come to life? Yes. But... [50:50] I am just as interested in that aspect as I am the more... [50:55] individual aspect of it, which is what's our personal locus of possibility and how do we expand it? And so I think where you see these things add up together is... [51:08] "Wow, okay, I wanna talk about the ambitious future." But I also care about the ambitious future in a smaller way, in a more local way, in a more community-oriented way. I want people to...

[51:19] Wake up and think, oh, hey, I can do this thing. I can push myself a little bit further. I'm living my internal and external worlds are congruent with each other. [51:31] pushing... [51:33] I am expanding my worldview. And I think the way I've done that personally is through conversations with friends, conversations with people building great companies, and basically an understanding that my life is very constrained and there are all these possibilities that I'm maybe not aware of. So that's maybe a long answer, but... [51:51] I think the point of neo-ontologies is to be, to show you like, hey, there's this angle of like, software can be incredibly empowering. And we can use software to create all these new concepts and new, ontology means sort of like new concepts of the world. [52:07] enter this rich intellectual world and, you know, learn a lot about it. But I also care about, um, as you go more granular into the individual, which is, you know, the founder or the person doing this thing, how did they get here? Why are they doing this? Um, [52:22] How can we learn from them? And so merging sort of this larger picture ambition with this more granular ambition is maybe the goal for this project. And maybe that's a lofty goal, but it's something I've been thinking about. Why do you think you're attracted to these types of stories? [52:37] And clearly you've been long attracted to them, like much longer than you were doing this project. I think even on some level, like being a venture capitalist, like there's some draw there. [52:48] Or what is it about like this kind of corner of the world?

[52:51] I've always loved dreamers. I mean, even beginning from the poetry days or the writing about fiction days, it's like, oh, if you like fiction, you like dreaming. You like fiction, you like being immersed in a different world. And I think what these founders are doing are creating these new ideas. [53:10] conceptual frames of reality that are very compelling. And a lot of these frames actually become the future, you know, landscape of technology, you know, [53:23] All of these ideas actually... [53:27] harvest and become much larger things. And I've always been really [53:32] excited about the early days, like the early clay of forming things before they're fully legible. And they will become legible. And so I'm just interested in that moment of change. Well, it's not just legibility, too. There's an element of it's fantasy and reality. Meeting. Yeah, exactly. Maybe it goes back to that, which is like, oh, yeah, we're always looking for when... [53:53] the frontier of when fantasy meets reality. [53:58] There's a, maybe to reference Ando specifically in that piece, the first kind of profile you've done on Ando and Sarah, you say, her story reminded me of a Greek term I like, techne, which I might be pronouncing that wrong. Techni? Techni? Yeah. Comes up all over your writing. Techni, which means craft grounded in practice. A founder builds a particular shape of company out of their techni, all their experiences, personal craft and taste that they bring to the work.

[54:23] I'd love to hear about that. [54:24] as a [54:26] I think your lofty answer was good. The thing that, one of the things that feels very true about your interest is to cause back to all everything we talk about seriousness, but also this project specifically is that, [54:36] Um... [54:38] Even in the like, you and I had a conversation about this. It's in the piece like the care over linguistics and like little forms. And they allude to like all these little things. Like what is it? [54:50] And maybe... [54:51] What what opportunity is there to I would expect that's a theme that will to the extent you keep doing this will continue to show up in new ways. Like what is what do you see there? [55:02] Yeah, well, I think it, um, [55:05] That story was really compelling to me because Sarah is a second-time founder, and I think much of her learning in that reflection of starting a new company was amazing. [55:14] I'm good at these things, but what am I truly great at? And what is my natural leverage in this world? And what's the type of company that should come out of that? [55:23] natural leverage. I don't think a lot of us actually do that really deep work, which is maybe you get pulled into things that you think you're supposed to do or other people have in mind for you. But really, what's your true talent and gift in this world? And how can you put that into practice, put that into motion? And so tech night is a very [55:41] beautiful term and something that I think about a lot. Another sort of related concept is what Rebecca Solnit, a writer, talks about the cosmology of self, which is like everything that you make, whether it's a company, a piece of writing, a podcast, is this amalgamation of your experiences in the world.

[56:01] you know, how you grew up, all the things you read, all of the people you've met. It's a collection of these things. [56:09] brought into the furnace of something and come out the other side. And, um, [56:14] She writes this line, which is like underneath the task of writing a specific piece is making the self who can make the work you're meant to. [56:23] I just... It's like the exhaust. Exactly. It's the exhaust, which is like, you never look at this fully formed thing and be... [56:31] Maybe you do and you think it's wonderful and amazing and this fully formed asset or whatever. But actually what you really see in this very subtle moment is how a person's entire being has gone into this thing. And I think this applies to companies 100 percent. Like look at any like Notion, for example, or Ramp or any of these very large, significant companies are a. [56:55] you can actually trace back the lineage and the sense of this inevitable feeling, um, that it's come from the founder, right? It's Apple Steve jobs with 10,000 lives. Exactly. Exactly. And, um, [57:07] You and I read Christopher Alexander, who's an architectural theorist, and one of his concepts is, you know, all these little patterns are what makes a space come alive. And all these little patterns in, like, everything that you do makes your work come alive, makes your company come alive, makes your… [57:27] Yeah, it makes your work more whole and more you-based. [57:31] if that makes sense. So I'm interested in exploring that.

[57:36] Yes. [57:38] I'm gonna go back to it one more time, 'cause I can't help myself. The Sarah example. [57:43] Second company. Obviously, not quite the same idea, but... [57:46] So much of what you were just talking about is very related to the Ikigai, the idea of how do you find this convergence? And that feels – whereas previously, as I understand it, Sarah's previous company, Alloy, less of – but she's also maybe like you, very intense, driven striver who also cares about these other things, craft and da-da-da-da. [58:10] And so it's, [58:11] My assumption is that Sarah in her previous founding role had more of like separate identities. Yes. And now, and so maybe I'm, maybe that's my own question, but like, [58:22] On one hand, you seem okay with like, it's okay to have different identities and you don't have to force them together. I think for any young person, it's like, how should I be trying to find the thing? Is Ikigai now? Or should I like do my creative stuff and my professional stuff and then eventually converge it? [58:38] And you seem so interested. It's not inherently intentioned. It's not like total paradox, but it does seem that maybe you're just patient. [58:48] with [58:49] Yeah. [58:49] the fact that there are going to be sort of dualities and at some point they'll come together and when they come together, it's really beautiful. [58:55] Yeah, well, I think it's a process of discovery. I think you find Ikigai after a long route of discovery. And you don't have to force it. Yeah. And I'm sure if you talk to any founder, they're probably like, hey, the thing that I landed on, the thing that worked, actually took a long time to get it.

[59:12] Even think about artists. I mean, look at Monet. I mean, I was just looking at the Monet Water Lily exhibition, and he painted water lilies 250 times. And it's just incredible, right? But it's like, okay, it just took a lot of time to get right. And I think having that grace... [59:29] is also really important. [59:32] Grace is the right word. [59:34] Yeah, not only something like you probably literally can't force the convergence. Yeah. Yeah. [59:41] I think of Robert Irwin as well, like drawing the lines. Like just, yeah, just... And I almost wonder what, like someone like that, maybe I don't know if Monet did this, but he's like almost trying to like... [59:53] through so much repetition, he's just trying to have the ego part of it fall away. That's probably the main reason we actually can't converge faster, is that we're just like [1:00:03] It's your, am I overhearing the world or am I trying to narrowize it? Yeah. Narrowize it. Yeah. And I think importantly, as we circle around this question of like, okay, there's lots of dualities, lots of identities. You can be multiple things. You can be one thing. All of these different things is that I think it's important to note that, [1:00:20] In my writing, I'm not actually trying to be prescriptive. I am trying to be a peer or like I'm trying to stand next to the person. And like I said, whatever is your personal locus of possibility, I want to expand that in you or like in the reader. And I'm not actually trying to teach someone or say how things should be or tell you that you should merge these identities. It's more like, hey, can you walk next to me while I am, you know, trying to figure this out for myself and, you know,

[1:00:47] can we learn something together? So I think that's maybe the frame I'm coming from. It's interesting. Perhaps this isn't correct, but it reminds me a bit of Joan Didion in the way that she, I was talking to somebody this week and I was observing that like, [1:01:03] In slouching towards Bethlehem, I sort of much preferred... [1:01:06] her personal writing... [1:01:08] and notes and things to even some of their reporting. [1:01:10] But on some level, like... [1:01:13] She tries to convey this aspect of like, I'm not putting myself into this totally, or at the very least, I'm not trying to tell you anything. I'm just kind of observing. [1:01:23] In so doing... [1:01:25] there's a huge amount of self in it. And it's like, yeah, I don't know. It really works well. What do you... [1:01:32] What do you hope this becomes? [1:01:34] New ontologies? [1:01:35] I hope that it becomes... [1:01:38] an archive [1:01:42] or, you know, documenting a very important time in technology, first of all. I think watching the shapes of new companies being built in this time [1:01:50] well, there's some legendary companies that are going to be built in this era. And I just want to be involved in writing those stories, first of all. And then second, I hope that it touches on that ambition thing again, which is – [1:02:02] Okay, I am looking at a person creating something new. [1:02:06] How can I, in my own life, find the agency and the... [1:02:11] hope and the ambition to do something of my own. And it doesn't have to be big. It doesn't have to be a company. But how do I actually push myself to...

[1:02:21] achieve greatness or improve myself in this more personal way as well. [1:02:27] Hmm. [1:02:28] Hmm. [1:02:30] I think it will make you a better investor. [1:02:33] Yes, I think so. Why? I think it's, well, it's something about, so I guess some backdrop is, you know, I spent almost a month with them, kind of in and out of the office and lots of walks with Sarah and... [1:02:47] Uber rides and dinners. And I think the thing that came out of it was actually just watching someone work ambiently. [1:02:55] It's really important. It's a different level of access. It's a different level of access. Almost anyone's getting it, but certainly a VC or somebody's going to get it. Right. And it's just, yeah, it's a different level of... [1:03:06] You know, I think there's always this sense of like... [1:03:09] masking in some ways when you're meeting in a very [1:03:13] contrived state where it's like, I'm an investor and you're a founder, you know, it's just like 30 minutes. I, you know, it's a hard stop. You know what I mean? And I don't really like, I think that the practice of actually not having hard stops is really important. Um, [1:03:30] You know, I've always admired people that actually go the extra mile. [1:03:35] An example is, you know, someone I know, a partner on the team, you know, flew to this very remote part of Canada for this team and pretended, you know, and acted as their intern and, you know, got them coffee and donuts, you know. So it's just it's just one of these levels where people.

[1:03:52] You get to know someone on a very [1:03:53] deep and everyday level, which [1:03:56] I guess gives you patterns or helps you understand what you're looking for in people. [1:04:01] Hmm. [1:04:03] That's cool. Do you have a call for anything, any types of founders or companies you're looking for? Or is somebody reaching out to you? Like, you do not want to be a part of any club that would have you as a member. That's funny. No, I'm very, I mean, I'm. [1:04:17] Looking for the right fit with me as well. What does that mean? I think... I'm even curious what that means in your day job, too. Right, yeah. I think it's more creative leaning. Okay. A little oddball. You know, lyrical, appreciates art, and... [1:04:36] Thanks a lot about... [1:04:37] both the technically interesting parts that I can share about the product, but also the poetic sensibilities that come with that. Why is that not just like... [1:04:50] That's cute, but like, why does that... Do you think that it has any impact on... [1:04:54] Success. [1:04:55] if we were to zoom way out and be like, okay, all the humanity, dah, It's cool. Right, It's cool that Sarah likes to, like, but like either she's going to sell enterprise SAS or she's not. Right. Well, I push back a little on that because, um, let, let's use Ando as an example. Like Ando is like a software product, but it's, it's, it's also in some ways a cultural product, right? You're going to, [1:05:15] Actually, if we think about, you know, Andro is an AI native Slack or a Slack built from scratch for agents. [1:05:21] If you think about it, we spend so much time on this platform every single day. And the way the notifications impact us is actually psychological, psychosocial. It's it's, you know, it's actually like, you know, a really interesting human aspect of it. And so much of what she's trying to do and something I really like is that she's trying to make this experience feel different.

[1:05:42] And in making something feel different, making an interface feel different, it unlocks this sort of agency or experience in a human being that... [1:05:52] is almost close to enjoyment or flow or allows you to step into creativity in a different way. Or certainly prevent the opposite, which most messaging platforms just hijack my... Yeah. Right. And so I do believe that there's something there around... [1:06:10] There's something there about like competitive differentiation, which is like maybe you need a founder who actually understands culture. [1:06:16] Yes, and when there's certainly a... [1:06:21] I love the psychosocial point. [1:06:24] Maybe there's an always has been element of this, but certainly looking forward, [1:06:27] The delineation that the tool you use while you're at work, eight hours of your day, shouldn't... [1:06:34] Like it doesn't matter as long as it's useful. It doesn't matter how it feels. Maybe that was tolerated for a long time, but like it certainly doesn't seem like it will probably be tolerated for much longer. Right. [1:06:45] Um... [1:06:49] Yeah, I'm really curious to see. I mean, obviously... [1:06:52] I'm personally asking that question as an advocate. I'm certainly hopeful that these things matter. Yeah. [1:07:00] But I also do wonder if it's a little bit [1:07:02] romantic. [1:07:04] And maybe it depends on the thing. [1:07:08] A chat app is probably as, like, consumery as you're going to get for a... [1:07:11] an enterprise tool.

[1:07:13] Yeah, well, the way you put it, which is, well, this kind of product, you don't really do [1:07:18] outbound sales on it. And maybe in an enterprise SaaS, if you're selling to maybe insurance carriers, that's maybe a slightly different... [1:07:25] Um, [1:07:26] Right, but why can't that be more beautiful? That can also be more beautiful. Yeah. And use and beauty. Now we have enough abundance. Yeah, yeah, yeah. Use and beauty are not also... [1:07:36] that separate. - Trade-offs. - Right? Which is like, if something's more beautiful, you might use it more. [1:07:43] And so I think there is some link there. How do you think about like, this is so silly, but like, what do you think of like Amazon? Like Amazon is so not beautiful. Right, but it's so useful. [1:07:54] Ubiquity and scale is also so useful, right? Yeah. Yeah. But let's say, well, let's use that example, right? Like if there's an Amazon that has the same ubiquity and scale and has the same, you can buy the same things. [1:08:07] But it's a much more beautiful interface. [1:08:09] Are you wedded to Amazon as a brand? Right. And I don't know if I would use the word beauty, but at least effectiveness. There is a case to be made that you're looking the wrong thing, that Amazon's buttons don't matter. The beauty in that experience is that you can press a button and have something appear. I don't know if it's beautiful. [1:08:27] Maybe the point is that the core of the thing... [1:08:30] is whatever it is that you're perceiving the core of the thing to be has to align with the pattern of distribution or something like that. [1:08:40] yeah I mean to put it a different way maybe it's like

[1:08:44] Did you, this is cliche, but like, did you truly sweat the details on the, on the part that really matters? On the part that matters. Yeah. Yeah. [1:08:51] Yeah. I like that a lot. I mean, well, I'm very excited for the future of new ontologies. Hopefully there will be many more to come. [1:08:58] I want to talk a little bit. I'm just curious to you did a, and I don't know if you put any of this out publicly, but you did some work on memory, uh, [1:09:05] Or this year. Or last year? Last year. There's a specific thing that stood out to me in reading some of your notes around Leighton versus living memory. [1:09:13] And this idea that like... [1:09:14] you sort of frame it as like latent memories that is the potential to be recalled and shared and living memory is relationally created. Um, [1:09:20] How does living memory change? [1:09:23] When you... [1:09:25] Prompt it or activate it on your own in writing versus when you [1:09:29] when it's actually relational. [1:09:31] Is there a delineation there? [1:09:34] Yeah, maybe first to give credit to that idea. It's actually comes from Kie Kretler's work on artificial memory and the, you know, the reading that she's done there. And I love that so much. And I, you know, used it as part of the presentation. I also talked to Kie. So just want to say that first. But her whole point is that... [1:09:53] or maybe her point mixed with my point is that, you know, the study of memory that I did was two pronged. One is understanding the mediums in which writing and writing. [1:10:03] memory and history have changed over time and what has that done? And then the second, which is more of a, like, okay, technology, what does memory mean right now, context management thing. But if we focus back on your question, which is like, how do we think about living memory versus latent memory?

[1:10:20] I think part of it is understanding, like, how does memory get transmitted communally? So an example of this is, [1:10:29] In the past, writing used to be on all of these different mediums, like stone, papyrus, tablet, and all of these... [1:10:38] history and words used to be moved around physically. You'd have to like physically be in the room. And with the mention of, you know, things like the printing press became [1:10:48] this dissemination of a large corpus of knowledge that you could access anywhere. And, you know, Walter Ong and Marshall McLuhan kind of frame it as, okay, now you're going back into the individual, you can sit alone and reflect on the things that you've written, reflect on the things that you've done. And so maybe the point that I'm trying to make there is sort of like, there is this one form of historical memory that was a transmission, a communal, you know, expression [1:11:18] sitting alone in a room and sort of [1:11:20] cogitating and thinking about things in the past and synthesizing them, bringing them [1:11:24] to the present. Um, [1:11:27] And they're just two different forms. It's funny. That makes me think about, like, that's happened to, like, most of media. Yeah. I mean, it's still an example. You think about, like, a film used to be this really almost spiritual experience of, like, we're going to go project something on the wall of the cave. Like, we're going to. [1:11:41] You're going to sit in a room with a bunch of other people and they project a magical story on the wall. And now we sit in our beds on our phones privately with our private screens. There's an element of that, too, that I think probably extends beyond just the memory implications, which is like the...

[1:11:56] Yeah, the way that so much of that experience, even when you're just looking at a phone with another person. [1:12:03] It was like such a different experience. Yeah. Yeah. [1:12:05] Yeah. Well, there's this, I think you'd like this metaphor, but there was this, in one of the books that I read, I'm forgetting the name, it's probably in... [1:12:14] Elizabeth Eisenstein's printing press book was this example of the cave. And one of the caves, one of the historical caves that they were... [1:12:25] looking at or looking into, and I think Werner Herzog talks about that as well in his films, is that you go into a cave and it hasn't been touched. But when you do analysis on the cave, actually, some of the drawings were like, [1:12:38] 10,000 years old and from somewhere like 5,000 years old. You know, like there was a continuation of something. Yes. And lineage. Yeah, like a lineage. And I think that's really powerful. Right. And I think writing works this way, too. Or we return to the point of like, oh, how do we think about writing as memory, which is that [1:12:58] I think that writing is not a static thing. It's something that people continue to iterate on. They think about your idea and they relate back to a different idea. Like the example of Michael Nielsen, he wrote a piece on developing creative identity, which I remixed and said, hey, this is how I think of creative identity for myself. And so this remix culture or this more communal sense of memory is something that I'm quite interested in thinking about. I think we're losing it. [1:13:23] Thank you. [1:13:25] I think we're losing it.

[1:13:27] I don't know if I'd say we're losing it. I think... [1:13:31] I think there's a lot more... [1:13:33] Remixing happening. It's true. [1:13:38] What was my... [1:13:40] Intuition pointing out there. [1:13:42] Yeah, it feels like one aspect of that muscle, like it's easier for anything to be... Maybe what I'm pointing out is we have less collective techs. [1:13:51] Hmm... [1:13:52] There's maybe a different idea. [1:13:54] But I'm thinking of this, like, canon of the cave, of the thing in the cave. Yeah. Well, maybe if you think about it, where – look, now we have all of these AI tools. [1:14:10] collection of [1:14:11] texts. [1:14:12] or collection of prompts and responses are siloed in these little channels that are just between you and an AI thing. Oh, I see. There's another aspect of which is actually a model trained is sort of a version of this corpus. Right, yeah. It's different connotations. Yeah, yeah, yeah. There are two different orientations. What broadly did you learn or conclude? A ton of this work was specifically around LMS and AI. [1:14:39] in memory. What it... [1:14:40] And even a lot has changed in six months. I think so much of the, at least the technical side of the work was about context windows and so on and so forth. Now they're just getting bigger. But what have you concluded and maybe what perspectives do you have in your personal use of memory with these tools and what's good or bad or what direction things should kind of be pushed? Yeah, well, it's funny, you know, after I completed that research, it was a three month sort of project on memory. I thought, well, maybe this is going to be relevant, maybe not.

[1:15:10] Ando is context management. And how do you feed the agent the right thing at the right time? How do you create new, how do you, you know, the longer context window isn't actually better. We're thinking about retrieval and all of these different ways to make language more ergonomic for agents. Right. And so it was funny because it was a weird recurrence. Exactly. Where it's like, oh, dang, like maybe something, you know, maybe things always appear when they're meant to. And so actually a lot of the learnings were extremely practical, which is I don't think I could have understood the Ando product [1:15:40] that research and understanding of context engineering. Um, [1:15:44] from a technical standpoint, which I think is interesting itself. In terms of this, like, broader, I guess, memory as a medium kind of work that I've been doing, um, [1:15:56] It's just been pushing me to think about how do I include community more in the writing? How do I continue to remix things and to make writing more open and accessible to other people so that such that they can remix things? And so maybe that's my orientation towards it, which is creating more. [1:16:13] open spaces for creativity. It reminds me of Tyler Cowen talking about like [1:16:17] writing for the LLMs. Have you seen this? No, I haven't. What's it about? He just is like... [1:16:22] I'm trying to like now he's giving some interview and he talked about like visiting Iceland. And then later in the interview, he's talking about this. And he's like, yeah, now they all know what I think about Iceland. [1:16:31] which is, like, more useful for me, but also, like... [1:16:34] I'm like, maybe I think what he's gesturing at is like you're kind of like bending the, well, [1:16:39] Maybe one aspect is maybe you're influencing them, but I think maybe actually better to your point is you're you're adding to the lineage or something. Yeah, yeah, yeah, exactly. And by externalizing like, um.

[1:16:51] As someone who's done a lot of writing in your life, most of which hasn't been public, [1:16:54] Something has changed in the way that you've contributed to this... [1:16:59] project of humanity or whatever, like, uh, not, not to be overly lofty, but there is something to that. I think. [1:17:05] Yeah, it goes back to also, I think distribution is important because it helps you reach that one right person for which that writing can hit them at a particular time. [1:17:14] And they can integrate it into their life. There's been so many short stories or books that I've read where I read it at a particular time, and it influenced the way that I did my work. I was telling you earlier about Robert Caro, and Working, Researching, and Writing is the name of his book. It's sort of like a side book, because if you think of Robert Caro's books, you think like Power Broker and then LBJ and all these different books. [1:17:44] Thank you. [1:17:44] interviewing Sarah Ando, how do I go about talking to these people [1:17:49] And he talks about this moment where he's sitting in the library with all of the stacks of like, you know, back when there were files, right? He goes into this dungeon of files and he sits along the files and he and his researcher go... [1:18:01] each of the files, each of the phone books and try to call up different people. And when I read that, I was just like, [1:18:06] Dang, I'm just like... [1:18:08] not digging deep enough. I'm not gnawing on the bone hard enough. Like I need to be pushing it. Right. And so I think there's like moments like that where, you know, a piece of writing, [1:18:18] can change one person's life. And that's like really has long-term butterfly effects.

[1:18:25] Thank you. [1:18:27] Very good reminder to nudge towards... [1:18:31] externalizing thing. I mean, yes, it ties to something we were talking about way back in the conversation of just like, [1:18:36] Yeah, the benefits of making something real. Yeah, exactly. Exactly. [1:18:40] Thank you. [1:18:41] Totally different category of thing, but something that really stood out to me in a piece of yours you were referencing a [1:18:47] a series of quotes from Caroline Knapp's Appetites. [1:18:51] Hmm. [1:18:53] And it is specifically a kind of like a feminine cut on desire and ambition and appetite. This is Caroline. The primarily underlying striving among many women is the appetite for appetite, a longing to feel secure and safe enough to name one's true appetites and worthy and powerful enough to have them satisfied. The question of appetite and specifically what happens to a female appetite when it is submerged and rerouted. Female appetite moves in guilty, circuitous ways. Where are the lines between satisfaction and excess, between restraint and indulgence, between pleasure and self-destruction? [1:19:23] Deemed to inhabit a realm of essential sparseness, sensuality, and strong emotion not completely absent, but muzzled and kept least in the yard. Wanting is a frightening thing, especially when you lack models for it or permission or a sense that your desires are good, valid, and satiable. [1:19:39] or is it really? It's so good. Amazing. And obviously there's a specific, I'm quite interested in the specific feminine part of this, but I think there's also a meta thing, which is I talked with Henrik and I had had a few conversations recently about just like desire in general and wanting, and like how often are you really letting yourself into this like, [1:19:55] almost like childlike desire.

[1:19:59] version of this that I think relates to some of the seriousness and, and, and effort and, and, and that conversation. But I'm, I'm curious how you relate to this, maybe even having since read it and, and letting your appetite grow in a way that feels, you feel connected to and healthy and feels like aligned versus maybe a more, [1:20:17] ravenous or ego-based ambition or desire or something. [1:20:22] Yeah, I think that book was very instrumental in helping me understand that if you submerge desire or you, yeah, if you reroute it, it always just comes out in some weird way. You know, like if you're like she's talking a lot about, you know, um. [1:20:36] appetite and food in some ways. But that's the whole separate conversation. But I think in terms of allowing yourself to feel desire, allowing yourself to say, I want more than this. [1:20:49] It's like it goes back to the point of like, hey, look, like you grew up thinking that all of these things. [1:20:55] Things are... [1:20:57] inbuilt constraints, and then you actually learn that they're not inbuilt constraints. I think that's like a really important thing. And we've talked about before, which is like, how do you [1:21:07] understand that you can be differently free and, you know, free in different ways that you're not originally. And some of that's true, just like mere exposure to things that you're interested in. So let's say one example is, for a long time, I desired having friends in creative circles. [1:21:22] It's just like, oh, I have this really interesting creative part of my life and I don't feel like I have, you know, I have community there. And so much of like writing the blog is being like, hey, like.

[1:21:33] I'm creating this community like or I'm looking. It's a search query for other people who are creative. Yes. Allowing myself to express that desire is not very shameful. It's actually quite empowering. But if you yeah, if you don't, then there's always this feeling that you keep coming back to or it haunts you in some ways. [1:21:52] I love that. [1:21:53] It's... [1:21:55] On the note of allowing yourself to want more, like... [1:21:58] There's a recursive nature to this where, or reflexive, like my friend Steph Ango, he has this [1:22:04] blog post nibble on your appetite will grow. [1:22:06] which is kind of like more of a general thing. But there's an element of that in this too, which is like, okay, do I want to have a creative life or do I have creative friends who are like, and could I, am I allowed to have that? And then by the way, you write a blog post and you like, [1:22:20] oh wow, there's people like, and it compounds on itself. Yes, yeah. I think it's like an underrated element of, one of, not this whole can of worms, but like one of the underrated parts of agency is that it like, it compounds. Yes. Like by being agentic makes you more agentic. Confidence is the memory of success. Yeah, yeah, exactly. [1:22:40] Oh, yes. Yeah, it makes me wonder about... [1:22:44] What are the ways that all of us probably... [1:22:48] What are the things I... [1:22:49] might want or desire that I've like not. It's like, yeah, you're allowed to have this, but... [1:22:53] We wall ourselves off in interesting ways. Yeah, which is maybe another way to put it is like, what's the truth of the matter? What's the deep down truth? And I think we use a lot of different things to mask that deep down truth. And engaging with it in a non-shameful way is actually...

[1:23:12] really relieving. Like one example is, I think the past few years since being in venture or having more interesting, honest conversations with different people, it's like, oh, actually, I could have just said the thing that was underneath the thing. What's the question under the question, right? And oftentimes, you put the question on top of the question, so that, okay, eventually, we're going to meander down to the question. But like, let's get to the bottom of the question and answer it. It's great for everybody. It's great for everything. It's great in business. It's great in personal relationships. It's just [1:23:42] Make it real. Yeah, make it real. It just comes back to this, yeah. [1:23:46] You brought up differently free... [1:23:49] I love to talk about friendship. You have some amazing writing on friendship. Maybe specifically on that note, [1:23:54] There's like a tension between [1:23:56] In some other place, you had suggested your closest friends should make you feel free and safe. [1:24:02] Which is beautiful. And yet, I think it's in the context of the differently free part, you had said, relishing the company of people who sometimes make you feel, by comparison, uninformed, closed to new ideas, disordered, defensive, rigid, fearful, unambitious. This is an acquired skill. It kicks up shame. It humbles you. It dares you to grow. Yeah. [1:24:20] which is [1:24:21] Yeah, definitely true. Like, relate to that. A beautiful part of the differently free thing. And yet, like... [1:24:26] that can be quite alienating. Sometimes being around people who are differently free doesn't make you feel more free. It makes you... [1:24:34] it's deeply humbling and also it almost makes you like, have you noticed patterns in the people who sort of, the ways that they're differently free expands you, even if it takes a little time versus like,

[1:24:47] - Wow, the gap between us is so big, it's almost like, [1:24:50] Alienating? Yeah, it's a great question. I think when I say they should humble you and dare you to go, I don't mean that in a... [1:24:59] direct sense. They shouldn't be like, "You're really bad." It's more like, "Wow, this is out there." Yeah, this is out there. Like, "Oh, watching Jackson do his podcast inspires me that I can do a podcast." You know what I mean? Like, it's sort of, well, I mean, I'm not there, but just by, I think, inspiration through witness is what I'm talking about. Rather than this sort of like, [1:25:20] conflicting, conflicting, more antagonistic relationship with another person. Yeah. It's bringing it down to earth, even if it's really great. Like seeing somebody up close, as we've talked about, like seeing somebody up close, like [1:25:33] does make it more real and thus like... [1:25:36] On one hand, you see the amount of detail required and the effort required, but also like it is real. [1:25:40] It's not this imaginary... [1:25:43] Well, again, going back to the effort piece, right, is if you were looking at someone from the outside, you'd be, you know, you'd be so intimidated by the things that they've created. Because you don't actually see the inner working of, you know, how much effort they're putting in. I think a lot of my friends that I really admire, I've just seen them put in so much effort and force, applied at this very specific angle, and eventually works. But I saw the journey from, you know, the beginning to get there.

[1:26:13] You have to compound. You have to compound. And you have to try, right? Yeah, a little bit. You have to show up. You have to show up. Can the same person make you feel really, can do this, like this freedom thing, and make you feel really safe? Are those like different roles? [1:26:27] I think they can come in the same person. That's not intuitive. Yeah. I mean, it's... [1:26:33] AND I THINK THAT'S A GOOD THING. [1:26:33] Well, one thing that I also write about is, you know, it takes two to think, which is creative partnerships. And there's lots of examples that I look up to, like Amos Fersky and Daniel Kahneman. [1:26:45] Even Joan Didion and her husband, John, were a creative partnership in some ways. [1:26:51] C.S. Lewis and J.R.R. Tolkien, you know, in Oxford and all those things, which is sort of like, oh, for a long time, I was reading this book. [1:27:00] you know, um, [1:27:02] biography of C.S. Lewis and Tolkien. And in it was that for a long time, we were each other's only audience. [1:27:09] Right. But they were also really challenging to each other. I mean, honestly, the friendship was challenging. Like if you read the actual end to that, they end up having a bit of a tiff and, you know, a bit of conflict there because of religious beliefs, because of writing beliefs. But I'd argue that they're probably different. [1:27:27] They probably did both. They're probably like, I'm your biggest supporter. I'm your number one person that I'm going to read this and encourage you. Deep trust, but not low standards. But not low standards. And I'm going to push you and it's going to be hard. Yeah. Yeah. I think you're so right. I think you're so right. [1:27:42] Couple other things I'm friends. Uh,

[1:27:45] Friends, you help us see ourselves. [1:27:47] In Winterson's The Passion, Henri says this about love, but I think it's just as resonant about friendship. It is though I wrote in a foreign language that I am suddenly able to read. Wordlessly, she explains me to myself. Like genius, she is ignorant of what she does. Then each friend represents a world in us, a world possibly not born until they arrive, and it is only by meeting this that a new world is born, the diary of Anae Nin. [1:28:14] Maybe there's an open-ended part of this, or maybe it would be better to get specific. I know you've referenced and you've talked to me a little bit about your friend and former collaborator, Justine. [1:28:22] But I'm curious what, yeah, what does it feel like to have somebody who can do, a friend who can do that for you? Yeah. So for some context, Jesse and I went to college together. We lived together for four years. And we wrote a blog together. My first sub stack ever. That's not actually, many people don't know about this sub stack. It was called Kopi Club. Kopi? Kopi. I grew up in Singapore and Kopi is a local drink there. [1:28:52] world. And I think [1:28:56] So much of what Justine said [1:28:59] helped me see [1:29:00] was, number one, sheer encouragement. I think she always believed in me in a way that maybe didn't make sense at the time. A little bit illegible. [1:29:09] And the other thing is that when we were writing together, it truly felt as though we were...

[1:29:17] improvising together. So there's this line that Patti Smith writes about her friend Sam Shepard when she's learning how to improvise with music. And he says, hey, after one beat of the drum, stop getting so rigid about it. You can just add another beat. The music hasn't ended. We can keep going. And I think so much of what Justine and I's friendship [1:29:36] is so... [1:29:39] that quote is so relevant because I think whenever I was stuck or lost or a listless, Justine would say, hey, let's, [1:29:45] Let's keep going. And I think that was a very beautiful thing. We wrote 30 pieces together. And that's a lot. That's a lot to write with another person, let alone by yourself. Yeah, what an amazing, truly, truly one of the great attributes is... [1:30:01] is when someone makes you feel like things are possible. [1:30:03] Yeah. [1:30:05] Like there's road ahead. [1:30:08] It makes it easier to step. Yeah. And also, I mean, one other part is... [1:30:13] Oh, I want to... [1:30:15] impress my friends. I trust their judgment. I want them to feel proud of me as well. [1:30:23] It's a good reason to have high standards. Exactly. Yeah. [1:30:26] Again, maybe this applies to Justine or maybe not. Maybe just broadly... [1:30:30] Hua Su in Stay True. Friendship rests on the presumption of reciprocity, of drifting in and out of one another's lives with occasional moments of wild intensity. [1:30:40] This points to something that I certainly feel deeply, which is... [1:30:44] Friendship is this strange relationship we have where like, there's no obligations. There's no rules at least. And so most relationships, at least the farther and farther you get away from like the kind of confined school, like parts of your life. Um, or like there's this old, old essay I always reference. It's like your best friend could tell you on a whim they're moving across the country. And if you protested, it would be weird. And like, if a romantic partner did that, you'd be a sociopath, whatever. Um,

[1:31:09] - Yeah, how do you relate to that? How do you relate to that, again, maybe with people in your life who you aren't in active proximity with, which is obviously so important. [1:31:17] Yeah, well, I think you're pointing at something which is... [1:31:20] really deep and true about friendship which is that it's sort of under theorized as a [1:31:25] connected tissue. Anyone can sort of be a friend in some ways. Are we friends yet? People can be friends and collaborators and all of these different things. But I think it's actually about, I don't know, like soul resonance. I feel that if I understand someone's [1:31:47] character and soul and what they are put on this earth to do, that bond is actually very difficult to sever. [1:31:53] And so even when I reflect on, Justine lives in London, and we rarely, like honestly, we see each other maybe like in person once a year. I'm actually seeing her in two weeks. [1:32:04] We really don't have a lot of surface area, but there's a lot of density. There's just a lot of density. You and I see each other not that regularly, but when we do, we're going on three-hour walks. So it's sort of... [1:32:19] depth of friendship rather than breath. [1:32:23] One of my theories is that people deeply underrate proximity in relationships. Um, [1:32:28] And so you can talk yourself into like, oh, we had this really meaningful walk or whatever. And then when you, well, part of maybe what I'm getting at is I've had, I've gone back into proximity with old, very close friends. And I thought we were as close as ever. And you realize when you get back into extreme proximity, you're like, oh, this is a little different. Right. Yeah. I think it can be maintained with a very close friend here and there. How do you think of mental proximity? So like, I get physical, right? But like, you know, you live next door to each other.

[1:32:58] other's orbit. [1:32:59] It has to be a non-intentional. [1:33:02] That's my answer. So if you're in an active group text with, [1:33:05] multiple other people? [1:33:07] It doesn't really work on a one-on-one. I have two of my best friends who I now live in the same city as, who largely, Brenner and Andrew, who are big parts of me doing this podcast, needed a kick in the ass, basically. Uh... [1:33:18] We, for the first five years of our friendship, we didn't live in the same city, but we had a very active group text, which is different than like, "Hey man, we should catch up." [1:33:26] Which is great. Intentionally matters. Hey, I'm thinking of you. But I suspect... [1:33:32] Again, maybe with your very best friend or a person you like. But for most of the other relationships, if you don't live in the same city, you need to have some kind of. Right. There must be some kind of rhythm, maybe. There's some threshold as well. Yeah. Yeah, there's some threshold that you have to meet to even, I guess, consider yourself close. Or, you know, enough exposure therapy to that person. Right. The physical version, this is like, you want to go on, like, we're going to run some errands together. Or we're going to sit in the car and not talk for an hour. Yes. Like. [1:33:56] That's a level you can't really get to with only intentionality. Yes, 100%. Yeah, sort of like blank space time or white noise. White noise time might be the one. Yes, yes, yes. Not a question, but I just thought it was so... [1:34:11] cool and lovely. Any thoughts to share on Linda Montano and Taicheng Shea and their tying each other together? Yeah. Oh my gosh. I loved that art piece where they actually tied a physical piece of rope to each other for 365 days, which is just insane. And they weren't allowed to touch? Yeah. And they weren't allowed to touch. And they weren't lovers also? No, they're just friends, I guess. I hope they can call each other friends. It'd be awkward

[1:34:41] Yeah, yeah, yeah. Talk about proximity, right? And, um... [1:34:46] Yeah, it's very... It was a really big... I think a lot of these, like, performance art pieces say something very true about the nature of, like, connection. And so... [1:34:56] part of that piece was actually just exploring what they did there. And there was this like a piece of paper that they signed, which is like, we will never be apart, which I think is, when they were finished, right? When they finished. Yeah. Yeah. Yeah. Yeah. [1:35:09] Thank you. [1:35:10] That would be quite crazy. [1:35:12] for some reason it makes me think, have you ever seen... [1:35:18] It's not related in any way, so I don't even know why I bring it up. Maria Abramovich. I have, yeah. Well, which one? The one where she's sitting in the thing in her old collaborator. Yeah, yeah. It's like this – maybe the reason I thought of it is the extreme antithesis of these two former incredibly dense – it would be like these two people if they were in love. They didn't see each other for – [1:35:37] years 30 years or something that is a moment yes yeah well i think maria abramanovich's work is like really about human nature i mean she also does this one where she's like you can do anything to her or whatever um and you see some people do some things where you're just a little shocked and um it's really about oh what do you do when the human um when all these like uh false pretenses of civility go away and um what happens and maybe it's a little dark right i think there's dark [1:36:07] Hmm. [1:36:08] related to friendship, love, uh, [1:36:11] You say...

[1:36:12] Complexity means appreciating the critical difference between love and attachment, between fantasy and reality. We experience friction when we're faced with the inherent mystery or a knowability of another. Ties to our conversation about reality and fantasy. You referenced, or excuse me, you recommended me a short story called Closer by Greg Egan. Why? [1:36:33] Is the unknowability of the other so important? [1:36:36] So beautiful. [1:36:38] Yeah. I mean, I'm curious to hear what you thought of the short story. But basically, the short story by Greg Egan, it's a book, Axiomatic. It's a science fiction set of short stories. And the book Closer is about this couple where one of them wants to constantly get closer to the other person. And so what they do is this sort of... [1:36:58] transformation where you can take someone's brain and put it into another person and you can inherit all of their memories and therefore become the same person, essentially. Or union, like become a union. Closer and closer. Closer and closer. And the moral of the story there is actually that... [1:37:12] It's the fundamental unknowability or the mystery of another person that interests us. Yeah. And that you can, I think it's a very romantic idea to constantly be surprised by, [1:37:24] by another person and to also be seen in a different way by another person. There's this quote, which is not in Greg Egan, but that marriage is like one long conversation. And I think part of a conversation that keeps it going is that you don't know what the other person is going to say next. And there's some surprise.

[1:37:44] There's lots of relationship theorists who talk about this dynamic as well, which is like, how do you keep the mystery and also the familiarity? Those are two... [1:37:53] poles of tension that you need to keep in the relationship. But I thought that short story just did a really great job of talking about, oh, hey, what happens when... [1:38:02] you don't fully know another person. Isn't that beautiful? Isn't it hard to actually know everyone, know everything about someone? [1:38:11] Yeah, you can surprise another person. You can also surprise yourself, I think, is the moral there. Yeah, especially you can surprise yourself by way of them. Yes, yeah. [1:38:22] Yeah, the thoughts I, I mean, one, it's, it's, it's a recommended, it's, it's short, and people can read it. It's a really beautiful, beautiful example of the way that reality is more beautiful than fantasy. Yeah. [1:38:34] I think in a sense, you had some other quote, you had said, "True resonance arises from the feeling that what you are seeing is real. It was forged through a complicated interconnectedness and friction with the world. Ironically, the apex of absolute beauty or symmetry or pleasantness lacks real intimacy. It's flat. You take a doll and feel nothing but the uncanny, but look at a face you love in all its quirks and think it in an immatably beautiful." [1:38:59] Maybe it's a silly thing, but my reaction in part to your prompt about Closer is, um, [1:39:05] There's an old idea from a friend who he says in a relationship you have to decide whether you'd rather be bored or annoyed. [1:39:11] Hmm. Yeah. And it's not quite the same. But I think there's an element of this which is like, yeah, you want both. The implication is you want to both be deeply seen and known and have more and more intimacy, which by definition, intimacy is knowledge. Right. And yet.

[1:39:29] As someone who definitely doesn't want to be bored, we need to be surprised. Yeah. And reality is surprising, even if it's abrasive. Again, maybe to the same theme. [1:39:40] Yeah. And I think it's very important to have the mindset of you can change and you will change, actually. And anticipating change is also really important. [1:39:52] I think you maybe saw this. I really love this one particular piece by John Repetti called "Yet Byron Never Makes Tea As You Do", which is about his wife. And I've quoted it so many times. I hope John Repetti is not annoyed at me. But he talks about, you know, seeing his [1:40:09] the chip in his wife's shrunk tooth and being, you know, so enamored in that moment with the, you know, story of the tooth. And he's like, well, if you actually look from the outside, it might look like an imperfection. But to me, it was, you know, proof of humanity sort of. [1:40:24] The title, "Yet Byron Never Makes Tea As You Do," comes from this poem by Virginia, a line in Virginia Woolf's book or novel. And it's, [1:40:33] in the poem or in the novel, the point is, "Oh, you're telling me that you do all these things like Byron, but [1:40:41] Byron never makes tea as you do when you spill the pot and you like mop it up carelessly and you like put the pot in a different place like and all these little quirks are like a little bit annoying, right? Like you didn't pour the tea perfectly, but that's what makes you you and you. [1:40:56] So inimitably you that if you were gone, I would weep. And I just thought that was so beautiful. And so I keep sharing it because I think it deserves to be read. And just like it's a beautiful piece.

[1:41:07] One of my favorite bits of that. Love begins not with me, but with the other. With the little eruption of the real that I experience in the other. Yeah, it's so good. Eruption of the real. [1:41:17] Just a few more things. [1:41:21] You have a line, you say, I spent a lot of time alone, finding myself in the chasm between solitude and loneliness, loneliness, I should say. [1:41:29] What's the difference between solitude and loneliness? What is that chasm? [1:41:33] Yeah, I think the chasm comes from, you can feel like really alone in a crowd of people. [1:41:42] and you can be surrounded by people and still feel alone and lonely. [1:41:49] In terms of solitude, you can feel really held and seen by a lot of people and you're just actually doing your own thing. [1:41:55] It's like, oh, I have a really vibrant, beautiful community of people that love me and care about me. But I'm just going to do my own thing. And I think that's the difference, which is like, oh, do I have people who really understand me? [1:42:06] and get me and hold me and I trust them. [1:42:10] So that I can be free and alone. Yeah, and choose to be alone. And choose to be alone. And what is the chasm? Is that you're sort of like dipping in between those two? Yeah, where it's like, oh, sometimes you forget. Yes, I was going to say. Sometimes you're like, I'm just this hyper-individual person in the world. And then you realize like, oh, no, actually, all of this, I'm built up of all of these things. [1:42:33] Other people. [1:42:34] I'm basking in the grace of all these other people around me. [1:42:37] It's funny, I thought you were going to go the other way, which is when you sort of like are willfully in solitude and you forget and you get lonely. Yeah, maybe you do. Well, I think that's also true. You spend enough time alone and maybe you start to feel alone. You're like, I chose this. I chose this. I promise I chose this. Yeah. Yeah. It's why I can never really go on a silent retreat. It's just like I love solitude, but I think that's a little bit too much solitude.

[1:43:02] Yeah. [1:43:03] A line on noticing. Here's what I like in people: perceptiveness, humility, wit, a feverishness toward good ideas, high conviction, an iterative process of self-understanding, equanimity. It's easy to distill this into language. [1:43:17] but it's hard to notice these things in real life. I think one of life's greatest skills is being good at noticing. [1:43:24] Either how have you... [1:43:26] improve to that or in the people who you really admire who do it [1:43:30] What? [1:43:31] What drives that? It relates to the attention stuff and the beauty stuff, but noticing is a specific word. [1:43:37] Yeah, I will... [1:43:41] have another reference for that but um there's this book that um i read recently called the swim in the pond in the rain by george saunders i have it on my shelf do you have it i think you'd really like it but i mean one of the the main um you know well first like one of the main points that he makes in the book is that oh [1:43:59] every person in this class, it's about his Syracuse MFA class about Russian short stories. He says, every person in this class has come to me already perfect. And I'm just helping them find their singularity. [1:44:09] And the whole book is basically like a deep reading of Russian short stories and why they work and the choices that they make. And why I bring this up, it seems kind of unrelated to noticing. But I think one learning from that book is that. [1:44:23] To notice deeply means to notice how you feel about a thing and like come to a worldview about a thing or about a person or about a piece of writing. And to actually understand the emotional reactions that you have with a thing and interrelationship that you create with anything that you consume or make or any person that you relate with. Noticing that dynamic, I think, is really important.

[1:44:47] Some conversations and some people are, you know, make you come alive and [1:44:52] create a new special world where like there's distinct taxonomies and distinct, you know, characteristics of that world. And in living in that world, you, um, [1:45:01] Living in that world, you experience a new type of feeling or a new type of way of living. So I think noticing to me is noticing the... [1:45:10] interrelationships. [1:45:12] A lot. [1:45:13] Hmm. [1:45:15] Yeah, a little bit even of like noticing the space between. Yeah. Yeah, I think he calls it the supra-personal space. [1:45:23] Not interpersonal, not super personal, but supra personal, which I think is cool. There's a line in Before Sunrise, and they're sitting in this alley, and she says if... [1:45:33] God or magic or whatever is real. Like it's like in the, it's in the, it's like when somebody's sharing something, it's like in the space between us trying to understand someone sharing something similar. Uh, a quote from Jeff Buckley. [1:45:44] I think in a piece of yours about feeling behind, or maybe things going the way we think they ought to. Life has its own rhythm. [1:45:53] and you cannot impose your own structure upon it. You have to listen to what it tells you. It's not earth that you move with a tractor. Life is not like that. Life is more like earth that you learn about and plant seeds in. It's something you have to have a relationship with in order to experience. You can't mold it. You can't control it. [1:46:10] Not necessarily a new theme, but... [1:46:12] Yeah, how do you remember... [1:46:15] Or how do you loosen your grip? [1:46:17] Hmm. I think if you actually look at the through line of my writing throughout time online, which is like four years or five years, maybe four, um,

[1:46:27] I think you'll see I've gone through a lot of peaks and troughs. Yeah. And I'm not afraid to say that. Like, I'm also like, oh, this is happening. And like, um... [1:46:34] And I'm going to write it down. Yeah. And I think the act of documenting and also just like, [1:46:40] little signposts in the journey of life. Yeah. I think is important to remember that you can't control things. Because even when I'm in like euphoria of having written a piece and like, you know, and like feeling like I'm on track with all these things, I remember that, oh, there's moments of like great, you know, great loss and great despair and great listlessness. Yes. And I always have to remember that these minima and maxima. You're setting like anchor points though. You're setting anchor points. Yeah. [1:47:06] And remembering that you can reach the maxima again, I think, is really motivating. [1:47:14] Oh, what a great answer. A little thing from Bob Irwin that you had sent to me that I think... [1:47:20] I [1:47:21] I'll read it. This is from that biography. We talked about him a little bit earlier. There is no such thing as a neutral gesture. Right? [1:47:27] because for that very fact of it being there draws a certain amount of perceptual attention. Let's say it drags away to 0.06. Well, then it's got to give back 0.12 in energy. Some mores are major moves, major gestures. [1:47:42] I mean, certain things are just support. Everything doesn't maximize all the time. There's some trade-off. But I did come to quickly see this thing about there being no such thing as neutrals. [1:47:53] Yeah, it just had me thinking about [1:47:55] especially in the modern era of like,

[1:47:58] Thank you. [1:47:59] It's so easy to do everything. Yeah. And where did detail and craft come in? And just these little subtleties. Yeah, maybe... [1:48:10] made me think of you and it made me [1:48:12] Um... [1:48:13] It just feels like kind of a beautiful philosophy for like... [1:48:16] the little nudges of things, but I was just curious if you had a reaction. [1:48:20] Yeah, I actually, there's a, I have a physical copy of Seeing Is, um... [1:48:25] Forget it. [1:48:44] Because I do think it's important to... [1:48:46] care about what you put out into the world and care that maybe it's making a statement, maybe it's sharing a perspective on the world. [1:48:55] And not having it be sort of a waste of space, if that makes sense. [1:49:00] Yeah, and every little... [1:49:04] Guy just drew lines all day. Every little flick matters. Yeah. A little. Well, small things aren't trivial. [1:49:11] Especially if you're attuned to them or you notice them, but it's, yeah, it's easy. It's easy. If you haven't, [1:49:16] It can be easy to not notice when you've got, when you've loaded yourself into just like focus, yeah, focusing on. [1:49:22] Maximizing output. You mentioned Miyazaki. One of my favorite quotes or anything you've ever sent me, a little quote on Miyazaki and effort. To endure something is obviously exhausting and agonizing, but at the same time, you must also continue to hold what you regard as important close to your heart and to nurture it.

[1:49:52] who cycles between joy and despair over the high or low rating his work receives. [1:49:57] this is related, I think, to what we were speaking about just now with Bob, but... [1:50:02] maybe the thing there is about personal standards and like independent of anybody else. Um, um, [1:50:09] maybe even like an autotelic aspect of it. [1:50:12] I think maybe the most interesting question for you would be about writing, but how do you... [1:50:17] What kind of keeps you... [1:50:20] Pushing. [1:50:21] Hmm. Yeah, that book, that quote is from, I remember the moment we were talking about it, which is in New York on a long run. And I... [1:50:32] I have that saved in my phone and I return to it frequently. And the reason being, it comes from his book, Starting Point, which is about the first 20 years, which is so funny that 20 years is a starting point. Right. I think that's in itself funny and kind of telling. Right. But I think that the other point that's really important there is that like. [1:50:53] You will always know. [1:50:54] You have the knowledge within yourself of the craft that you're making. It's that you will always know how much work that you put in, whether the outside world recognizes it or not. You can always look at the color or the particular hue and know that you chose it specifically. And I think that's when you can actually point to things that you did for... [1:51:14] The end is not the means. The means is the end, basically, which is in the process of choosing, in the process of [1:51:22] creating, you have the standard for yourself that you meet and it makes you proud. And, um,

[1:51:27] I think a lot about sort of creating is always in that middle ground of like making the work. [1:51:33] in the process of making the work rather than the final outcome. Yeah. [1:51:37] Great answer. [1:51:39] Two final quotes. [1:51:42] But as it is, aliveness means impermanence. We are brief bodies. Moment to moment, our cells turn over and our hands touch different surfaces. Our faces change with every smile, grimace, glance, frown. How could I expect us to say the same? I like this line I heard in the song once. Any love I made you feel is yours to keep. Some experiences are sealed into the past, but they were still very beautiful. And then don't covet. Give everything. Give it all. One of my favorite books on the topic is Annie Dillard's A Writing Life, where she writes, [1:52:12] freely and abundantly becomes lost to you. You open your safe and find ashes. Creatives tend to hoard notes and lines thinking they'll be used perfectly once at some point in the future, but writing is a deep well that continues to be refilled by life experience and reading and observations. Use every good sentence you have ever written now. Burn the candles. [1:52:34] It feels very fitting, something that came up repeatedly throughout this conversation. How do you remind yourself to... [1:52:41] to stay so abundant and so generous. [1:52:44] Hmm. I think the... [1:52:49] It's viewing creativity and... [1:52:53] the soul that you put into your work as renewable? [1:52:56] Ursula Le Guin has this line that's

[1:52:59] Love is like [1:53:00] bred, remade, everyday made new. I think the same is true for [1:53:04] creativity. Or there's always going to be more inspiring things to read in the world or to ingest. We forget though. We forget. Like we think like, oh, there's a finite number of interesting people to talk to. I only have so many good ideas. Yeah, yeah, yeah. So many good ideas. But actually, look, there's the deeper you go, the more rich it gets. And so reminding myself that, hey, no matter what I do, I will never reach the bottom of this well, I think is something that really drives me forward. And I think something that's very meaningful. [1:53:32] I think it shows in... [1:53:34] the work and the way you approach things. [1:53:36] It's an honor to do this. Thank you. This is so fun. Thank you, Jackson. [1:53:40] Thank you for listening to Dialectic with Nicole. You can learn more at dialectic.fm slash Nix. That's N-I-X. Also, if you enjoyed the episode, please give it a thumbs up, five stars, subscribe wherever you're watching or listening. [1:53:54] And especially, please share it with a friend if you liked it. Every little bit helps. And it would be an honor to have you share it with somebody who you think would really love it. [1:54:03] I'd also like to thank Notion one more time for presenting Dialectic. In a time when... [1:54:08] The central orientation towards AI is just about automating everything and moving faster and making every individual more capable, some of which are good things. I appreciate the notions orientation is about thinking together, how we can collaborate together [1:54:23] with each other, with teams big and small, and with the AIs to do better work. At the end of the day, the work I want to do, the work I want to be a part of, and I hope the same is true for you, is to collaborate with amazing people and do great work. For me, with Dialectic, that means focusing my time on immersing myself in the minds of the amazing people I get to speak to, like Nicole.

[1:54:41] having these rich conversations with them, and then putting that together in a way that is rich and exciting for you, whether it be the episode or the transcript and lessons and everything else. And I'm using AI on the edges to help streamline that process and focus on doing more of the work I don't want to automate. I'll also link to that great piece by Colossus on working inside of Notion. And as I mentioned, if you're interested, you can learn more at notion.com slash dialectic, or you can reach out to them or me at work at jacksandall.com. Thanks again for listening. [1:55:11] I will see you next time.