Description

Nicole Seah (X, Substack, LinkedIn), aka Nix, is a writer at Starting From Nix and investor at Costanoa Ventures. She recently launched New Ontologies, where she profiles founders and companies thinking ambitiously about the future. Her first piece is live now, on Ando: the team building a chat platform for the era of agents.

Nicole balances identities with poise, moving between the literary and the practical. I spoke to her about different kinds of beauty and how it takes us out of ourselves, Nietzsche’s case for tolerating strangeness, and choosing reality over fantasy. Then we discuss duality and balancing intensity and lightness, and talk through Borges, Hesse, Miyazaki, Alyssa Liu, and Joan Didion. Nicole argues that freedom comes from not collapsing yourself into a single identity. I asked her about the drive behind New Ontologies, her obsession with *techne, and Rebecca Solnit's "cosmology of self.” *We then skate across a range of ideas, including memory, appetite and desire, and friendship and why other people’s unknowability is part of what makes them wonderful.

I hope this conversation inspires you to look for and love what is real, to be patient with and attuned to the multiple people inside you, and to give freely of your creative life.

Full transcript and all links and references: dialectic.fm/nix.

**Dialectic is presented by **Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. Inside Notion by Brie Wolfson & Camille Ricketts for Colossus. You can learn more at notion.com/dialectic.

Timestamps

00:00 - Opening Highlights
01:14 - Intro to Nicole
02:04 - Thanks to Notion
03:48 - Start: Beauty — Effort, Attention, Strangeness
19:59 - Fantasy and Reality
29:41 - Multiple Identities, Intensity, and Lightness
49:08 - New Ontologies: Profiling Founders Building the Future
1:08:57 - Memory, Lineage, and Process
1:18:41 - Appetite and Honesty
1:23:47 - Friendship, Proximity, and The Unknowability of the Other
1:41:18 - Closing Notes: Solitude, Noticing, and Generosity
1:53:40 - Thanks Again to Notion

Links & References

Transcript

(0:00) Opening Highlights

(1:14) Intro to Nicole

(2:04) Thanks to Notion

(3:48) Start: Beauty — Effort, Attention, Strangeness

Jackson: (3:48) Nicole Seah, thank you for joining me. This is a long time coming.

Nicole: I'm excited to be here.

Jackson: (3:54) I'm excited for this. We've had many long, meandering walks and conversations, so I'm excited to capture a little bit of that in Hi-Fi. I want to start with beauty. I'm going to turn one of your lines back on you: How has pursuing beauty rearranged your life?

Nicole: (4:14) I think a lot about the quote by Iris Murdoch which says that beauty is a version of unselfing. I've always loved that term of beauty taking you out of yourself. One way beauty has rearranged my life is through reading beautiful works of literature. The sentence-by-sentence construction is gorgeous to me. I read a lot of translation as well. Seeing the choices the translator makes, but also the choices the author makes in parallel, is something I draw a lot of inspiration from.

Jackson: (4:58) You have an amazing piece on different types of beauty. I want to get into the details of that, but I have a couple of excerpts first. You start the piece in a complicated orientation to beauty. You say, "Only later I'd 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. 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." This was against the backdrop of a trip to Seoul, which is a very specific place in that world. 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." That is the same essence of the Murdoch reference. One interpretation I have is that there is beauty as a target—to make something or oneself more beautiful, or to effortfully make words or a podcast more beautiful. Then there is beauty as perception, which is a generous orientation towards recognizing the world is beautiful. Do you think those two things are at odds with each other? How do you think about intentionality in those two forms of beauty? The second one feels much more like the world is just happening to me and I'm perceiving it as beautiful, while the other feels very effortful. Does that distinction make sense?

Nicole: (6:53) It does, but I would say that both are actually quite intentional. The second is purposefully paying attention to the world. It's a frame of mind where I think a lot about ordinary magic. A lot of poets write about this. Some of my favorite poetry is about regular people and regular days. One aspect of beauty is noticing the ordinary and watching it come alive with a new sheen. Simone Weil said attention is the greatest form of prayer. They are both intentional, just with different frames. One is very inward-oriented and the other is more external, where I'm perceiving the world, taking in these inputs, and making something out of that.

Jackson: (7:47) Does that type of attention take effort?

Nicole: (7:52) I do. Sometimes a mountain range is just inherently beautiful, but I think some perceptual change is required for you to see the regular world as beautiful.

Jackson: (8:14) There is a Nietzsche idea you get into in the same piece. There is a cut on two types of beauty: easy to perceive and difficult to perceive. Nietzsche is talking about music and the way some things are easy to access. He says, "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 anew, presenting itself to us as a new, ineffable beauty. That is its thanks for our hospitality. Love, too, has to be learned." Elsewhere you say, "Tolerate strangeness long enough to be changed by it." You talk about developing a taste for difficult beauty or the ability to tolerate mental discomfort as one of the most important human skills to have. To consume novel things, to accept boredom and sadness, to be patient, and to override the aversion of being changed. I'm fascinated by this tension around something being strange and having to sit with it until the beauty inside changes us. It's so non-intuitive.

Nicole: (9:50) I think it's the frontier of the world coming together and the unfolding that happens between you and the world. There are lots of ways that, for example, Nietzsche talks about music. There's another piece by Zadie Smith that I really like called "On Attunement." It's about how she hears Joni Mitchell's song "California" for the first time. If you've heard "California," it's a bit of an odd song. It's in a different register and a different tempo than people are used to. She describes a moment underneath a cathedral when she hears the song and it completely flips for her. It's about context and engagement with the song in a difficult moment in her life or a moment of reflection. I think that's true for books and different types of media as well. Context matters so much. Sometimes we think everything is stable and in a contrived state. You might see or read something once and it doesn't hit then, but it requires patience and endurance to look at it again—to turn over the stone again and give things second chances. I'm a big believer in that.

Jackson: (11:13) That's a romantic and beautiful idea, and certainly one that most people will connect to. I had my own experience of that with Joni Mitchell. I already liked her, but I had heard "Both Sides Now" many times. I was on a walk one day and fully listened to it for the first time. I realized it was one of the best things ever written. That is a little different than the Zadie Smith example where she actually had an aversion to the music.

Nicole: (11:36) She had an aversion, yeah.

Jackson: (11:37) We have finite attention. The classic example is reading a book or watching a film and not connecting with it, then years later you come back to it. Time is doing a lot of work there. To go back to your point, I've changed. How do you know when to give something more? Assuming that some beauty is not easy, how do you know when to persist?

Nicole: (12:09) When it's challenging.

Jackson: (12:13) When it's challenging versus being numb or neutral.

Nicole: (12:14) Dispassion is probably the signal that there's nothing there. But if you feel there's something there and it's uncomfortable or abrasive—if you don't like it at all—then maybe return to it. There's some emotional register there that you're not quite aware of.

Jackson: (12:35) Are there any experiences, artistic or otherwise, that come to mind where you've had this kind of switch, almost like a horseshoeing?

Nicole: (12:45) There's actually a really good example. I took art history in college, and my professor was fabulous. She was very moved by art to the point where she would cry in the middle of our lectures. I was so energized by it.

Jackson: Was it a big class?

Nicole: It was a small seminar. There is a big structure called Donald Judd's Boxes in Marfa. It's a row of boxes in the fields of a barren land. She started bawling her eyes out in the center of class. For a long time, I didn't understand it and was shocked by that reaction.

Jackson: (13:33) Almost like, "Come on, are you really crying?"

Nicole: (13:35) Exactly. But there was a moment when I looked at some photos of those boxes when the sun was setting and the light was reflecting off of them. I read the backstory of why Donald Judd put those boxes there. It's about dualities like man-made versus artificial. I thought there was so much more texture there that I didn't pick up the first time. It changed my mind to see someone have a really emotional reaction to it. I also think that's why we enjoy friends' recommendations and trust people to show us what hits for them. You can adjust your view that way as well.

Jackson: (14:19) I wonder about this because it relates to something else we'll talk about. I know a movie you like a lot is The Boy and the Heron. It's a good example of a phenomenon I've had many times. The first time I saw it, I watched the dub. Robert Pattinson was really going for it as the bird, and I love Miyazaki, but I really didn't know what was going on there. Then I read an amazing review by film critic David Ehrlich and watched The Wind Rises. Without additional context from other people, I may have watched The Boy and the Heron years later and connected to it then. Instead, I watched the sub two weeks after reading that review and a few other things. Then I really connected to it and loved it. I had this complicated relationship where I felt like I was cheating because I needed somebody else to show me how to see. I wonder how you relate to that versus when it happens on your own, whether on a long time horizon or just from standing in front of a painting for ten minutes until you cry. It feels more earned. Am I just in my head about that?

Nicole: (15:35) I don't think of instinct as anything earned. It's earned to spend time and engage. Engaging could mean staring at something for ten minutes, or it can mean talking to people. I think of attention and learning much more as communal things. For a long time, I thought of it as a hyper-individualistic endeavor, but now I'm much more open to the fact that when I want to understand something or learn a new concept, it's always through community. It's always through hyperlocal experiences of that thing. I would say that is also earned.

Jackson: (16:17) Maybe I'm clinging to some sense of needing originality.

Jackson: (16:23) To go back to your communal idea, it would feel more valid to talk with a few friends who all saw The Boy and the Heron. If I outsource an opinion from a professional critic, it feels different. When you're doing this communally, how do you maintain a sense of your own interiority and ideas versus the risk that anything you consume quickly makes your thinking very relational? You don't get the aspect of going through something on your own. Do you have a relationship to it? Maybe you're oscillating. For a simple example, you read a novel or a book, spend some time thinking about it, and then you go to the book club and journal. It feels like you want some amount of the relational and some of the isolated. You don't want to overly rotate to one. I'm wondering how those two things blur together.

Nicole: (17:40) The danger point is if you don't actually feel anything toward a particular piece of work, but because everyone tells you you should feel something, you've labeled it as meaningful. Whereas 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.

Jackson: (18:01) It reminds me of Celine Nguyen. She talks about Proust, and a different cut on this would be that you don't have to like this for some arbitrary reason because you're supposed to like it. But also somebody like Celine saying this is fun and gossipy might be a portal in for your own experience. I really love the idea that attention is actually about putting in the time.

Nicole: (18:30) I love Celine's work. An important part about what she's doing is expanding the market for literature through sharing her perspective on things. I do think that's very powerful. Maybe you do need someone to guide you, and there's nothing wrong with being guided sometimes as well. I don't have any shame regarding where I come to things or how I get to things. It's always about how I feel about this thing at the end of the day. Have I learned something along the way about myself or about the world? I think that's a much more honest and meaningful way to come at it.

Jackson: (19:13) There's also less ownership.

Nicole: (19:15) There's so much less ownership and less pressure.

Jackson: (19:17) It comes back to the idea that the most beautiful things relate to introspection. I talked with Henrik Karlsson about introspection and he has this Nick Cave example. He talks about pushing ourselves to introspect with yourself as the subject, not as the object. It feels like beauty is something similar. It's not, "Who am I?" or "How can I be beautiful?" It's just, "What am I noticing?" When you take that orientation, I'm sensing in a lot of your answers this very outwardly directed orientation that is less concerned about whether it's your idea or somebody else's idea.

(19:59) Fantasy and Reality

Jackson: (19:59) There's a related idea to beauty where you write about fantasy and reality and the ways that we cling to fantasy when reality is actually far more rich, real, or beautiful. "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." "I expect when I look back on all the notes I collect this year, I'll see the inverse of fantasy. That what lasts, what feels right looks nothing like what I first imagined or dreamed about. There are no more fantasies to cling onto. There is no past, no backward place for my longings, only forward into the night, led by the beacon of beauty." That is a really sweet sentiment. How have you learned to love what is real?

Nicole: (21:14) I was referring to several different novels in that writing. One of my favorite character arcs involves a young man who goes for glory and victory on an insane quest, and through that quest realizes that what he dreamed about and fantasized about for so long was not real. He has to return to reality and live reality. I'm always interested in that inflection where you see something and think it's real, but you realize it's a mirage or it wasn't what you hoped for.

Jackson: (21:53) It wasn't what you hoped for.

Nicole: (21:54) Right. That's a very important life inflection point where you start to realize the things that you dreamed about or hoped for are not coming true, but you can actually chart a new path. It opens you up to a new aperture of thinking. Fiction is always a really interesting, very extreme version of reality. Maybe we don't go on an insane quest into the Wild West, but we do go on these little quests where we hope and dream for things. There's some fundamental truth to the fact that we don't always get what we want.

Jackson: (22:43) The texture of the story is deeply real.

Nicole: (22:46) Exactly. When I think about everything that I love and care about, whether it's a beautiful piece of work or a person, it's always the moments where they chafe against the edge of reality that I realize they're human and flawed. I'm also human and flawed, and that makes it deeply relatable. When I reflect on everything that's happened in my life, all of the really good moments unfolded in ways that I didn't anticipate, didn't plan for, and maybe didn't even have the imagination for, which is really beautiful.

Jackson: (23:29) How do you know when you're actually encountering reality? In much of modern life, we live a bubble-wrapped existence. In terms of stakes, we don't face death very often. 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 the job you want. But in a lot of cases, it's a little more subtle. Does that feel true to you, or is it only true in hindsight? I find there are glass-shattering moments, but a lot of the time I realize it a year later.

Nicole: (24:13) I think it's both. There are moments where you're really shell-shocked or let down by something or someone, and you didn't get the thing you wanted. Then there are other moments where it's only with time passing that you reflect back and realize that while you didn't get what you wanted, you got something far better. Having that mindset is important. Prior to the past four years, I had a very rigid mindset. I was a big planning personality.

Jackson: (24:48) Until four years ago?

Nicole: (24:50) Maybe four or five years ago, whenever I started writing publicly. I had a very big planning personality. The process is actually me learning how to not plan for things and to be surprised by the unexpected.

Jackson: (25:06) Is your strategy of introducing more reality simply not planning? That seems like an almost passive openness to reality. But there's probably another orientation that's like the Henrik line: make contact.

Nicole: (25:22) Make contact with the world and make it yield something.

Jackson: (25:25) How do you do that?

Nicole: (25:26) I think it's saying your ideas out loud and testing them. There have been moments where people have shut down my ideas, and it's always really humbling. But in hindsight, I've always been really grateful for those moments because perhaps there was some truth in them. Perhaps there was something I had yet to learn and had to incorporate into the work to make it better. Having intellectual honesty is really important.

Jackson: (25:57) That often relies on externalizing it to be totally intellectually honest. It's very hard to realize you're in a fantasy world.

Nicole: (26:05) Yes. It's no good thinking alone.

Jackson: (26:12) Back to The Boy and the Heron, you make such an excellent point. That's what that film is about. The dreamland is pretty appealing, and you wonder why you would ever leave. It's really easy to lull myself into believing my fantasies unless I'm forced out. One example is that I've been fortunate to have friends who will smack me across the face. There's a David Whyte quote I think we both like a lot. He says, "Whatever a 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 is the meeting between what you desire from your world and what the world desires of you. It's this frontier where you overhear yourself and you overhear the world." Maybe this relates to the notion you were pointing out about your exchange four or five years ago with the writing. You had said it's important to overhear the world rather than narrate it in advance. There's an element of the planning thing in that, but again, this is back to the more subtle part of it. What does it feel like to overhear the world?

Nicole: (27:33) Maybe this is a naive or innocent point of view, but I do see the world as benevolent. Narrating it internally in your head actually closes you off to any sort of external information, redirection, or feedback. It's always dangerous when you close yourself off to feedback or live in a sealed chamber. It's much more useful to actually see the world and talk to people. Even when you're getting bad feedback, it's actually kind of benevolent. People are telling you that something's not registering or something's not working. I remember a moment in art class. I used to paint a lot before I wrote. I painted with acrylics, and my art teacher came up behind me and said the painting could be so much richer and deeper if I added these different colors to it. I was ready to try it out. The art teacher came to me later and said I was the least defensive person she'd met because I was just ready to try things. I wasn't sure if it was going to work out, but I was ready to put new colors on the painting. I always think about that line of putting new colors on the painting as a frame in which to view the world.

Jackson: (28:57) Are you that way with things outside of painting or writing?

Nicole: (29:01) I think so.

Jackson: (29:03) Does that come from that experience, or have you always been like that?

Nicole: (29:09) Maybe it's a sense of egolessness. I don't necessarily have no ego—I think everyone does if we're honest—but trying your best to be egoless in the pursuit of beauty or craft is very important. You have to balance that with your own opinion about what you should be doing, of course. But there is an aspect of not taking yourself too seriously.

(29:41) Holding Multiple Identities and Balancing Intensity and Lightness

Jackson: (29:41) As I was doing the prep for this, I found myself continuing to swing on a pendulum. What you just said has this lightness and almost zen-like quality of being loose and egoless. Yet you are a person who writes about intensity, deep effort, and seriousness. You say beauty is effort; that effort is monstrous and ugly, but it also is the source of everything beautiful in this world. Somewhere else you wrote that in writing and in life, you need to "gnaw on the bone." This goes back to the reality thing: get under the skin and into the crevices. You've said writing has become bloodless and fake, but people crave the real. Am I making up this tension?

Nicole: (30:37) No, there's definitely a tension.

Jackson: (30:39) People who don't know you very well would think you are very vibes-based. In some sense, you have a creative life in writing that is probably a little bit more that way. Still, you write about Timothée Chalamet intensity and seriousness. Then you have a professional life as an investor that's much harder. Those two things seem so at odds.

Nicole: (31:12) I think you put it really well: I have multiple identities. The reason they feel at odds is because sometimes those identities conflict or come into friction with one another. I don't know if you've read the short story "Borges and I" by Jorge Luis Borges, the Argentinian writer. I think you would really like his short stories. It's about him having a separate writer self and then himself. They are circling around each other and one wins, but who is it? I read that and really related because there are these two parts. There are always these dueling parts of me: one very serious, intense side and then this more playful, light side. Maybe disambiguating those identities has been really helpful to separate out that tension.

Jackson: (32:03) Are you taking that on from a persona sense? People talk about taking on a persona when they're writing, performing, or at work. Do you feel that duality when you're at work versus when you're writing versus the rest of your life, or is it a little bit subtler?

Nicole: (32:21) I do feel the distinction, and it is something I'm working to bridge.

Jackson: (32:26) The implication is that it should be bridged. Is some separation good?

Nicole: (32:31) Maybe. I don't have answers here, but I do think you can successfully have them separate. My personal endeavor is to bridge them slightly more.

Jackson: (32:45) Not to attempt to answer my own question, but it does seem that both aspects for you—the playfulness and lightness and the intensity—are about loving what is real. They're different cuts on that, but they both are in service of that.

Nicole: (33:08) There are a bunch of books by the German author Hermann Hesse that I love, and all his books are about duality. If you've read any of them, like Siddhartha or The Glass Bead Game, Narcissus and Goldmund is probably the most relevant here. It's about two monks. One is very ascetic, lives in the tower, and becomes an intellectual and professor. The other is a man of the world who goes into the world and engages in acts of sensuality and violence and all of these raw things. At the end of the novel, they come back together and have a conversation. When I read that novel, I thought, "This is us. This is everyone. This is me." There's one part of you that's in the tower and one part of you in the world, and you're constantly dealing between the two. He doesn't pass any judgment. It's not like one is better than the other, but each is its own integral nature. You have to fulfill your integral nature.

Jackson: (34:24) I love that answer. I'm probably stretching, but it reminds me of My Dinner with Andre. Have you seen that film?

Nicole: (34:30) I haven't.

Jackson: (34:31) It's not quite the same, but it's a similar element of duality. The director doesn't seem to be taking too much of an opinion, which is the critical part. That certainly describes Siddhartha too. On the seriousness, effort, and commitment thing, you wrote that 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. That duality is there again. It's a surprising description of a very serious person. I think in that piece you're referencing Timothée Chalamet from a year ago. I agree with you, but when you think of seriousness, it seems...

Nicole: (35:29) Maybe my thesis is that it is through seriousness that you find playfulness. It's through seriousness that you find this level of skating through the world. I write about Miyazaki a lot and he's a great inspiration to me. He hand-drew his frames until well into the 70s when CGI was available. In one amazing interview, he says he was thinking about how to make the dragon move. He went to a restaurant and looked at the eels wriggling around and thought about how an eel moves. He is constitutionally unable to not care, and that is what makes his films so light and beautiful. When you watch a Miyazaki film, it's got all these dualities inside. There are children who have to grow up too early, wars, famines, fires, and lost children. At the end of the movie, you come away feeling like that was a beautiful, playful, light expression of art. There can be both. There always is both.

Jackson: (36:53) I've been wrestling with this and it's come up in conversations. We had this moment circling around the figure skater, Alyssa Liu. The intense person gets crushed by the person who's having fun. It's like Novak Djokovic saying he likes hitting the tennis ball. I was talking to Nick Thompson about the ultra-runner Kilian Jornet. Everybody's pissed because he's just having a blast out there. This relates to finding the thing that feels like play to you but feels like work to everyone else. I've had this conversation with people who ask how much of it should feel like play. Should it be 20% or 60%? Meanwhile, you talk to writers and every writer says they hate writing, but also it's excruciatingly meaningful. I struggle with this. Should it feel easier or should it feel intense and hard? My sense is that Alyssa Liu is someone who is deeply serious. That doesn't mean it's toxic, but it also doesn't mean it's all easy all the time.

Nicole: (38:11) The expression of it is playful. When you see her on ice, she is clearly having so much fun. Maybe I am projecting onto her.

Jackson: (38:19) She's done the work.

Nicole: (38:20) She put in the work. On ice, she can relax because her muscle memory is carrying her through that piece.

Jackson: (38:29) We could talk about this all day. Have you seen Miyazaki and the Heron, the documentary they recently made? He is amazing. There is a line in there: "If we don't create, there is nothing." I don't think he's having fun. He is deeply burdened. People usually swing one way or the other. My sense is you were right; Alyssa Liu on the ice for the Olympic gold was truly living it and present in it. Maybe that's specific to a performer. She did the work in the interim. Maybe it's just getting to the point where you're able to put in all this intensity and then let yourself drop the weights.

Nicole: (39:20) Exactly. I read the Joan Didion collected interviews last week, and one of the lines I saved was, "Salvation comes from extreme and doomed commitments."

Jackson: (39:34) That's a banger.

Nicole: (39:35) It's such a banger. She is asked later in an interview about that line, and the interviewer asks if she thinks it's a doomed commitment. She said, "No, I think it's salvation."

Jackson: (39:47) She was talking about her marriage.

Nicole: (39:49) She said marriage, children, and writing. She thinks that's salvation, actually.

Jackson: (39:55) It's both.

Nicole: (39:56) It's both. It's a commitment and it's also salvation.

Jackson: (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." Do you still feel that way?

Nicole: (40:13) I go in waves. There are moments where writing feels effortless and easy. There are moments where I know I have to dig and excavate something, and it's going to require concentration and effort. I'm currently writing a piece about Robert Caro, The Power Broker, and his process. It is something I really admire, but I actually have to do the reading. It's a slog, but it's really meaningful.

Jackson: (40:54) You have an old piece about peaks and troughs. One of my first guests, Jason Lew, says confidence is the memory of success. There's an element of knowing I have to do this slog again, but I've been here before and I know what's good on the other side. That makes it a little easier as you progress. Do you find that the amount of slog is pretty constant, or is it getting easier over time?

Nicole: (41:29) It's getting easier to accept the paradigm.

Jackson: (41:37) On the note of doomed commitments, how has commitment to yourself and your writing helped you make yourself proud? You referenced Murakami on his routine. He says the repetition itself becomes the important thing. It's a form of mesmerism. He mesmerizes himself to reach a deeper state of mind. You don't write professionally and you don't write daily, yet you have a deep commitment to that. How does that happen? Did it start with more scaffolding, or does it still require a lot of scaffolding?

Nicole: (42:47) It's part of my identity now. That is how all change happens, where you integrate it into part of yourself. I've been writing online publicly for four years, but I've been writing since I was ten years old in lots of embarrassing outlets. I was on Wattpad, Blogspot, WordPress, Wix, and Tumblr. It's a continuation of that younger child in me that was always writing. I also wrote a poetry portfolio and thought poetry was the craft. I still think there are poetic sensibilities in the writing, but they're not so condensed in form. How do you develop good faith in other people? You develop good faith by trusting that another person is going to do what they say they'll do and show up at the right time. That applies to yourself. How do you have good faith in yourself? You actually do the thing you say you're going to do. That's been a big contributor to continuing the writing. I've told myself I'm going to show up here, and I don't want to let myself down the way I wouldn't want to let a friend down.

Jackson: (44:13) Do you have a relationship with yourself like that with other things, or only writing?

Nicole: (44:21) Multiple things: writing, creativity, work as an investor, and fitness.

Jackson: (44:33) Creatively you reference poetry and painting. Are those moons circling the sun of writing, or did you ever have that commitment level with painting?

Nicole: (44:44) I tried. If you want to get really good at one particular medium, it benefits you to spend more time in that medium. Painting is just a very long process; you need a lot of patience to paint.

Jackson: (45:09) You need a lot of patience to write a lot, too.

Nicole: (45:11) Painting feels like I would have time for nothing else in my life.

Jackson: (45:16) You wrote a recent piece referencing Michael Nielsen's idea. One question I was thinking of as you were speaking is that at some point, commitments and good faith stop being a habit and start to become an identity. I am someone who writes. In that piece, you speak about the lightness of the writer's identity. 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 in service of your other multiple identities: scientist, researcher, investor, designer, founder. Instead, you chose the phrase "sustaining creative aliveness" because creative aliveness is the process of discovery, collection, synthesis, and finally expression. It seems you have a deep identity-level commitment to being someone who writes, yet writing is also a tool. Many people silo their creative lives and their professional lives. Writing, perhaps more so than painting, is easier to bring into other worlds. It seems you are holding this writing thing firmly, but you do not need it to define the person you are.

Nicole: (47:05) The point we keep circling back to is that it is fine to have multiple identities. Writing can be one of those identities in service of all these others. You do not have to have the tyranny of one identity. When you silo yourself into one particular identity—whether it is an investor or a writer—you close yourself off to other things that you are interested in. It is fine to be a multifaceted and multi-identity person. It is okay for that to be slightly illegible as well.

Jackson: (47:43) Do you think that we can form new identities, or is it more like harvesting and discovering what is already there?

Nicole: (47:57) I think it is harvesting. Things show up early.

Jackson: (48:09) But we maybe neglect them or do not water them.

Nicole: (48:11) Exactly. I am sure there is a life in which I could have become a painter, but I chose not to.

Jackson: (48:20) Does that life feel totally lost to you?

Nicole: (48:23) No. At some point, maybe I will harvest that identity. It would be another one in my little box.

Jackson: (48:27) That is an elegant model for much of what we have been discussing. There are all these seeds in your garden. You can spend all your time there, build a big wall in the middle, or have two core parts of the garden. You can go back to things. In the fullness of time and maturity, you eventually look around and realize it is just one garden.

Nicole: (48:53) I like that a lot.

(49:08) New Ontologies: Nicole's New Project Profiling Founders and Companies

Jackson: (49:08) I appreciate you checking me on the identity concept. Clearly, I am trying to force everything into one jumble. Recently, you launched a new project which brings two parts of your identity together. Historically, your writing was more poetic and personal, and for a long time was even synonymous. Now you have another life as someone deeply committed to technology and startups, specifically dreamers building impressive things. You said, "I enjoy the work I do with early-stage software because it's all about telling ambitious stories of technology, failure, reconstruction, and where fantasy confronts reality and markets while casting a romantic hope for the future." That is beautiful. I would love to hear what New Ontologies is and where it came from. What is behind this, and how has it felt to find this bridging in parts of your life?

Nicole: (50:13) The tagline of the New Ontologies website is: "How do we talk more ambitiously about the future?" When I was reflecting on that tagline and what this project is, I thought about how we access ambition at different scales. On one scale, ambition is this really large moonshot vision of the future. How do we make reality malleable to our inventions? As the quote says, "The world is just a museum of passion projects." How do we make those projects come to life? I am just as interested in that aspect as I am in the more individual aspect: what is our personal locus of possibility and how do we expand it? Where these things add up is that I want to talk about the ambitious future in a smaller, more local, and community-oriented way. I want people to wake up and think they can push themselves a little bit further. I want their internal and external worlds to be congruent with each other as they expand their worldview. Personally, I have done that through conversations with friends and people building great companies, and through the understanding that my life is very constrained by possibilities I am not aware of. The point of New Ontologies is to show that software can be incredibly empowering. We can use software to create new concepts. New ontology means new concepts of the world. You can enter this rich intellectual world and learn a lot about it. But I also care about the individual founder or the person doing this thing. How did they get here? Why are they doing this? How can we learn from them? Merging this larger picture ambition with this more granular ambition is the goal for this project. It is a lofty goal, but it is something I have been thinking about.

Jackson: (52:34) Why do you think you're attracted to these types of stories? Clearly, you've been attracted to them much longer than you've been doing this project. Even as a venture capitalist, there's a draw there. What is it about this corner of the world?

Nicole: (52:51) I've always loved dreamers, beginning from my poetry days and writing about fiction. If you like fiction, you like dreaming and being immersed in a different world. I think what these founders are doing is creating new conceptual frames of reality that are very compelling. A lot of these frames actually become the future landscape of technology. All of these ideas harvest and become much larger things. I've always been excited about the early days—the early clay of forming things before they're fully legible. They will become legible. I'm just interested in that moment of change.

Jackson: (53:44) It's not just legibility. There's an element of fantasy meeting reality.

Nicole: (53:48) Exactly. Maybe it goes back to that. We're always looking for the frontier where fantasy meets reality.

Jackson: (53:56) To reference Ando specifically, in the first profile you've done on Ando and Sarah, you say her story reminded you of a Greek term you like: techne. It comes up all over your writing. It means craft grounded in practice. A founder builds a particular shape of company out of their technique. All their experiences, personal craft, and taste are brought to the work. I'd love to hear about that. One thing that feels very true about your interest is the care over linguistics and forms. They allude to Tadao Ando. What is the opportunity there? I expect that is a theme that will continue to show up in new ways as you keep doing this. What do you see there?

Nicole: (55:02) That story was really compelling to me because Sarah is a second-time founder. Much of her learning in starting a new company was reflecting on what she is good at, but also what she is truly great at. What is her natural leverage in this world, and what type of company should come out of that? I don't think a lot of us actually do that deep work. You get pulled into things you think you're supposed to do or that other people have in mind for you. But what is your true talent and gift in this world, and how can you put that into motion? Techne is a very beautiful term and something I think about a lot. Another related concept is what Rebecca Solnit talks about as the cosmology of self. Everything you make—whether it's a company, a piece of writing, or a podcast—is an amalgamation of your experiences. It's how you grew up, the things you read, and the people you've met. It's a collection of these things brought into the furnace and coming out the other side. She writes that underneath the task of writing a specific piece is making the self who can make the work you're meant to.

Jackson: (56:24) It's like the exhaust.

Nicole: (56:25) Exactly. It is the exhaust. You never look at a fully formed thing and just think it's a wonderful asset. What you really see in that subtle moment is how a person's entire being has gone into it. This applies to companies 100%. Look at Notion, for example, or Ramp. Any of these very large, significant companies have a lineage and a sense of this ineffable feeling that has come from the founder.

Jackson: (57:02) It's Apple and Steve Jobs with 10,000 lives.

Nicole: (57:04) Exactly. You and I read Christopher Alexander, and one of his concepts is that all these little patterns are what make a space come alive. All of these little patterns in everything that you do make your work and your company come alive. It makes your work more whole and more you. I'm interested in exploring that.

Jackson: (57:36) I'm going to go back to it one more time. The Sarah example of a second company is very related to ikigai—the idea of how you find this convergence. Sarah is an intense, driven striver who also cares about craft. My assumption is that in her previous founding role at Alloy, she had more separate identities. Now, you seem okay with the idea that you don't have to force them together. For any young person, the question is whether they should find ikigai now or do creative and professional work separately until they eventually converge. You seem patient with the fact that there are going to be dualities. At some point, they'll come together, and it's really beautiful.

Nicole: (58:55) It's a process of discovery. You find ikigai after a long route, and you don't force it. If you talk to any founder, they would say the thing they landed on took a long time to get right. Think about artists. Monet painted water lilies 250 times. It's incredible. It just took a lot of time to get right. Having that grace is also really important.

Jackson: (59:32) Grace is the right word. You probably literally can't force the convergence. I think of Robert Irwin as well, drawing the lines. I wonder what someone like that—and I don't know if Monet did this—is trying to do through so much repetition. He's trying to have the ego part of it fall away. That's probably the main reason we can't converge faster: we're either overhearing the world or trying to narrow it.

Nicole: (1:00:06) As we circle around this question of dualities and identities—that you can be multiple things or one thing—it's important to note that in my writing, I'm not actually trying to be prescriptive. I am trying to be a peer, standing next to the person. Whatever is your personal locus of possibility, I want to expand that in the reader. 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, "Can you walk next to me while I try to figure this out for myself and can we learn something together?" That's the frame I'm coming from.

Jackson: (1:00:52) It reminds me a bit of Joan Didion. I was talking to someone this week and observing that in Slouching Towards Bethlehem, I much preferred her personal writing and notes to some of the reporting. On some level, she tries to convey this aspect that she's not putting herself into this totally, or at the very least, she's not trying to tell you anything. She's just observing. But in so doing, there's a huge amount of self in it. It really works. What do you hope this becomes?

Nicole: (1:01:36) New Ontologies? I hope that it becomes an archive documenting a very important time in technology. We are watching the shapes of new companies being built in this time. There are some legendary companies that are going to be built in this era, and I want to be involved in writing those stories. Second, I hope that it touches on ambition again. I am looking at a person creating something new. How can I, in my own life, find the agency, hope, and ambition to do something of my own? It doesn't have to be big, and it doesn't have to be a company, but how do I actually push myself to achieve greatness or improve myself in this more personal way?

Jackson: (1:02:27) Do you think it will make you a better investor?

Nicole: (1:02:33) Yes, I think so.

Jackson: (1:02:35) Why?

Nicole: (1:02:36) I spent almost a month with them, in and out of the office, with lots of walks with Sarah, Uber rides, and dinners. The thing that came out of it was that watching someone work ambiently is really important.

Jackson: (1:02:56) It's a different level of access.

Nicole: (1:02:58) It's a different level of access. It's access that almost no one gets, but certainly a VC is going to get. There's always this sense of masking when you're meeting in a very contrived state where I'm an investor and you're a founder.

Jackson: (1:03:18) It is a 30-minute window block.

Nicole: (1:03:19) It's 30 minutes and a hard stop. I think the practice of actually not having hard stops is really important. I've always admired people who go the extra mile. For example, a partner on the team flew to a very remote part of Canada for a team and acted as their intern, getting them coffee and donuts. It's a level where you get to know someone on a very deep and everyday level, which gives you patterns and helps you understand what you're looking for in people.

Jackson: (1:04:01) That's cool. Do you have a call for any types of founders or companies you're looking for? Or are you someone where if they are reaching out to you, you do not want to be a part of any club that would have you as a member?

Nicole: (1:04:12) I'm looking for the right fit with me as well.

Jackson: (1:04:19) What does that mean in your day job?

Nicole: (1:04:28) More creative-leaning, a little oddball, lyrical. Someone who appreciates art and thinks about both the technically interesting parts of the product and the poetic sensibilities that come with that.

Jackson: (1:04:47) Why does that have any impact on success? If we were to zoom way out, it's cool that Sarah likes Donne, but either she's going to sell enterprise SaaS or she's not.

Nicole: (1:05:04) I push back a little on that. Ando is a software product, but it's also a cultural product. If we think about Ando as an AI-native Slack or a Slack built from scratch for agents, we spend so much time on this platform every single day. The way the notifications impact us is psychosocial. It's a really interesting human aspect. Much of what she's trying to do is make this experience feel different. In making an interface feel different, it unlocks a sort of agency or experience in a human being that is almost close to enjoyment or flow, or allows you to step into creativity in a different way.

Jackson: (1:05:59) It certainly prevents the opposite, which is most messaging platforms hijacking my attention.

Nicole: (1:06:05) I believe there's something there about competitive differentiation. Maybe you need a founder who actually understands culture.

Jackson: (1:06:17) I love the psychosocial point. Looking forward, the delineation that the tool you use while you're at work for eight hours a day shouldn't matter as long as it's useful—maybe that was tolerated for a long time, but it certainly doesn't seem like it will be tolerated for much longer. I'm curious to see. I was partially asking that question to play the devil's advocate. I'm hopeful that these things matter, but I also wonder if it's a little bit romantic. It depends on the thing; a chat app is probably as consumer-leaning as you're going to get for an enterprise tool.

Nicole: (1:07:13) With this kind of product, you don't really do outbound sales on it. In enterprise SaaS, if you're selling to insurance carriers, that's a slightly different frame.

Jackson: (1:07:27) But why can't that be more beautiful?

Nicole: (1:07:29) That can also be more beautiful.

Jackson: (1:07:32) And now we have enough abundance.

Nicole: (1:07:33) Use and beauty are not separate trade-offs. If something is more beautiful, you might use it more. I think there is some link there.

Jackson: (1:07:46) What do you think of Amazon? Amazon is so not beautiful.

Nicole: (1:07:51) But it is so useful. Ubiquity and scale are also useful. Let's use that example. If there is an Amazon that has the same ubiquity and scale, where you can buy the same things, but it has a much more beautiful interface, are you wedded to Amazon as a brand?

Jackson: (1:08:12) 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 at the wrong thing and 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.

Nicole: (1:08:26) Maybe the point is that the core of the thing, whatever you perceive it to be, has to align with the pattern of distribution.

Jackson: (1:08:40) To put it a different way, maybe it is: Did you truly sweat the details on the part that really matters?

Nicole: (1:08:49) On the part that matters.

Jackson: (1:08:51) I'm very excited for the future of New Ontologies. Hopefully, there will be many more to come.

(1:08:57) Memory, Lineage, and Process

Jackson: (1:08:57) I want to talk about some work you did on memory last year. A specific thing that stood out to me in your notes was latent versus living memory. You frame it as latent memory having the potential to be recalled and shared, while living memory is relationally created. How does living memory change when you prompt it or activate it on your own in writing versus when it is actually relational? Is there a delineation there?

Nicole: (1:09:34) To give credit to that idea, it comes from Kei Kreutler's work on artificial memory and the reading she has done. I loved it so much that I used it as part of the presentation. Her point, mixed with mine, is that the study of memory I did was two-pronged. One is understanding the mediums in which writing, memory, and history have changed over time and the impact of those changes. The second is a context management piece on what memory means right now in terms of technology. Returning to how we think about living memory versus latent memory, part of it is understanding how memory is transmitted communally. In the past, writing used to be on different mediums like stone, papyrus, or tablet. History and words used to be moved around physically. You had to physically be in the room. With the invention of the printing press, there was a dissemination of a large corpus of knowledge that you could access anywhere. Walter Ong and Marshall McLuhan frame it as a return to the individual. You can sit alone and reflect on the things you've written or done.

Jackson: (1:11:04) Got it.

Nicole: (1:11:05) There is one form of historical memory that was a transmission, a communal expression of memory. Then there is a form where you are sitting alone in a room, thinking about things in the past, synthesizing them, and bringing them to the present. They are just two different forms.

Jackson: (1:11:29) That makes me think about how that has happened to most media. Film used to be a spiritual experience where you would sit in a room with other people and project a story on the wall. Now we sit in our beds on our phones with our private screens. So much of that experience changes when it is no longer communal. Even looking at a phone with another person is a different experience.

Nicole: (1:12:05) There was a metaphor in one of the books I read—probably Elizabeth Eisenstein's printing press book—about a cave. Werner Herzog talks about this in his films as well. When you go into one of the historical caves and do analysis, some of the drawings were 10,000 years old and some were 5,000 years old. There was a continuation of something.

Jackson: (1:12:46) A lineage.

Nicole: (1:12:47) A lineage. Writing works this way too. Writing is not a static thing; it is something people continue to iterate on. They think about your idea and relate it back to a different idea. Michael Nielsen wrote a piece on developing creative identity, which I remixed to express how I think of creative identity for myself. This remix culture or communal sense of memory is something I am quite interested in.

Jackson: (1:13:22) I think we're losing it.

Nicole: (1:13:25) I don't know if I would say we're losing it. I think there's a lot more remixing happening.

Jackson: (1:13:35) It feels like it is easier for anything to be remixed. Maybe I am pointing out that we have less collective text. I'm thinking of this canon of the figure in the cave.

Nicole: (1:13:59) Now that we have these AI tools, the collection of texts or prompts and responses are siloed in little channels between you and an AI.

Jackson: (1:14:19) I thought you were going to say that a trained model is a version of this corpus.

Nicole: (1:14:30) They are two different orientations.

Jackson: (1:14:33) What broadly did you learn or conclude? A ton of this work was specifically around LLMs and memory. Even a lot has changed in six months. So much of the technical side of the work was about context windows and so on. Now they're just getting bigger. But what have you concluded and what perspectives do you have in your personal use of memory with these tools? What's good or bad, and what direction should things be pushed?

Nicole: (1:14:57) After I completed that research—it was a three-month project on memory—I thought maybe this would be relevant, maybe not. While I was writing the Ando piece, so much of Ando's context management, how you feed the agent the right thing at the right time, and how you create new things came up. 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. It was a weird recurrence where things always appear when they're meant to. A lot of the learnings were extremely practical. I don't think I could have understood the Ando product without having done that research and understanding of context engineering from a technical standpoint, which is interesting itself. In terms of this broader memory-as-a-medium work that I've been doing, it's been pushing me to think about how I include community more in the writing. How do I continue to remix things and make writing more open and accessible to other people such that they can remix things? Maybe that's my orientation towards it: creating more open spaces for creativity.

Jackson: (1:16:15) It reminds me of Tyler Cowen talking about writing for the LLMs. Have you seen this?

Nicole: (1:16:20) No, I haven't.

Jackson: (1:16:20) He was giving an interview and talked about visiting Iceland. Later in the interview, he said, "Now the LLMs know what I think about Iceland, which is more useful for me." I think what he's gesturing at is that you're adding to the lineage. By externalizing—as someone who's done a lot of writing in your life, most of which hasn't been public—something has changed in the way that you've contributed to this project of humanity. There is something to that.

Nicole: (1:17:05) Exactly. It goes back to the importance of distribution. Distribution is important because it helps you reach that one right person for which that writing can hit them at a particular time and they can integrate it into their life. There have been so many short stories or books that I've read at a particular time and they influenced the way that I did my work. I was telling you earlier about Robert Caro and Working, Researching, and Writing. It's a side book, because if you think of Robert Caro's books, you think of The Power Broker or LBJ. That book was instrumental in me thinking about how I go about interviewing Sarah Ando or talking to these people. He talks about a moment where he's sitting in the library with all the stacks of files. He goes into this dungeon of files and he and his researcher go through each of the files and phone books to try to call up different people. When I read that, I felt like I'm not digging deep enough. I'm not gnawing on the bone hard enough; I need to be pushing it. A piece of writing can change one person's life, and that has long-term butterfly effects.

Jackson: (1:18:27) That's a very good reminder to nudge towards externalizing things. It ties to something we were talking about way back in the conversation: the benefits of making something real.

Nicole: (1:18:39) Exactly.

(1:18:41) Appetite and Honesty

Jackson: (1:18:41) Totally different category of thing, but something that really stood out to me in a piece of yours was you referencing a series of quotes from Caroline Knapp's Appetites. It's specifically a feminine cut on desire, 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? We seem to inhabit a realm of essential sparseness, sensuality and strong emotion not completely absent but muzzled and kept leashed 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."

Nicole: (1:19:40) It's so good.

Jackson: (1:19:41) Amazing. I'm quite interested in the specific feminine part of this. But there's also a meta thing. I talked with Henrik recently about desire in general and wanting, and how often you're really letting your deep, almost childlike desire out. There's a version of this that relates to some of the seriousness and effort in that conversation. I'm curious how you relate to this, maybe even having since read it, and letting your appetite grow in a way that feels connected and healthy and aligned versus a more ravenous or ego-based ambition or desire.

Nicole: (1:20:22) That book was very instrumental in helping me understand that if you submerge desire or reroute it, it always comes out in some weird way. She talks a lot about appetite and food, but that's a whole separate conversation. In terms of allowing yourself to feel desire and allowing yourself to say "I want more than this," it goes back to the point that you grew up thinking all of these things are inbuilt constraints and then you actually learn they are not. How do you understand that you can be differently free in ways that you weren't originally? Some of that is through mere exposure to things that you're interested in. For a long time, I desired having friends in creative circles. I had this really interesting creative part of my life and I didn't feel like I had community there. So much of writing the blog is creating this community or a search query for other people who are creative. Allowing myself to express that desire is not shameful; it's actually quite empowering. If you don't, then there's always this feeling that you keep coming back to or that haunts you.

Jackson: (1:21:52) I love that it's on the note of allowing yourself to want more. There's a recursive or reflexive nature to this. My friend Steph Ango has a blog post, "Nibble and your appetite will grow," which is a more general thing, but there's an element of that in this too. Do I want to have a creative life? Do I have creative friends? Am I allowed to have that? Then you write a blog post and realize there are people like you, and it compounds on itself.

Nicole: (1:22:23) Yes.

Jackson: (1:22:24) One of the underrated parts of agency is that it compounds. By being agentic, it makes you more agentic. Confidence is the memory of success.

Nicole: (1:22:37) Exactly.

Jackson: (1:22:40) It makes me wonder about the ways that all of us are not letting ourselves. What are the things I might want or desire that I've not allowed? You're allowed to have this, but we wall ourselves off in interesting ways.

Nicole: (1:22:56) Maybe another way to put it is: what's the truth of the matter? What's the deep-down truth? We use a lot of different things to mask that deep-down truth. Engaging with it in a non-shameful way is actually really relieving. One example is that since being in venture or having more interesting, honest conversations with different people, I've realized I could have just said the thing that was underneath the thing. What's the question under the question? Oftentimes we put the question on top of the question so that eventually we meander down to the real question. Let's get to the bottom of the question and answer it.

Jackson: (1:23:37) It's great for everybody.

Nicole: (1:23:38) It's great for everything. It's great in business and personal relationships.

Jackson: (1:23:43) Make it real.

Nicole: (1:23:43) Make it real. It just comes back to this.

(1:23:47) Friendship, Proximity, and The Unknowability of the Other

Jackson: (1:23:47) You brought up "Differently Free." I'd love to talk about friendship. You have some amazing writing on friendship. Specifically on that note, there's a tension. You suggested that your closest friends should make you feel free and safe, which is beautiful. In the context of the "Differently Free" part, you said: "Relishing the company of people who sometimes make you feel by comparison uninformed, closed to new ideas, disordered, defensive, rigid, fearful, unambitious is an acquired skill. It kicks up shame. It humbles you. It dares you to grow." That is definitely true and a beautiful part of the "Differently Free" thing. And yet, that can be quite alienating. Being around people who are differently free doesn't always make you feel more free; it's deeply humbling. Have you noticed patterns in the people whose ways of being differently free expand you, even if it takes a little time, versus those where the gap is so big it's almost alienating?

Nicole: (1:24:51) It's a great question. When I say they should humble you and dare you to grow, I don't mean that in a direct sense. They shouldn't be telling you that you're really bad.

Jackson: (1:25:03) It's more like, "Wow, this is out there."

Nicole: (1:25:05) This is out there. Watching Jackson do his podcast inspires me that I can do a podcast. I'm talking about inspiration through witness, rather than a conflicting or antagonistic relationship with another person.

Jackson: (1:25:26) It's bringing it down to earth. Even if it's really great, seeing somebody up close does make it more real. You see the amount of detail and effort required, but it is real. It's not this imaginary thing.

Nicole: (1:25:43) Going back to the effort piece, if you were looking at someone from the outside, you'd be intimidated by the things they've created because you don't actually see the inner workings or 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 until it eventually works. I saw the journey from the beginning to get there, and that encourages you that you don't have to be perfect to actually do the thing.

Jackson: (1:26:13) You have to compound.

Nicole: (1:26:14) You have to compound and you have to try.

Jackson: (1:26:17) You have to show up.

Nicole: (1:26:18) You have to show up.

Jackson: (1:26:19) Can the same person make you feel like you can do this—this freedom thing—and make you feel really safe? Or are those different roles?

Nicole: (1:26:27) I think they can come in the same person.

Jackson: (1:26:29) That's not intuitive.

Nicole: (1:26:30) One thing that I also write about is "It Takes Two to Think," which is creative partnerships. There are lots of examples I look up to, like Amos Tversky and Daniel Kahneman, or Joan Didion and her husband John. There was C.S. Lewis and J.R.R. Tolkien in Oxford. For a long time, they were each other's only audience. But they were also really challenging to each other. The friendship was challenging. They ended up having a bit of conflict because of religious beliefs and writing beliefs. But I'd argue that they probably did both. They were each other's biggest supporters and number one readers who encouraged each other, but they also pushed each other and it was hard.

Jackson: (1:27:34) Deep trust but not low standards.

Nicole: (1:27:36) Not low standards. I'm going to push you and it's going to be hard.

Jackson: (1:27:39) You're so right. A couple other things on friends: friends who help us see ourselves. In Jeanette Winterson's The Passion, Henri says this about love, but I think it's just as resonant about friendship: "It is as 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. It's only by meeting this that a new world is born. That's from The Diary of Anaïs Nin. I know you've talked to me a little bit about your friend and former collaborator, Justine. I'm curious what it feels like to have a friend who can do that for you?

Nicole: (1:28:28) Justine and I went to college together. We lived together for four years and wrote a blog together. My first Substack ever, which many people don't know about, was called Kopi Club. I grew up in Singapore, and kopi is a local drink there. The Substack was letters to friends, letters to each other, and letters to the broader world. Justine helped me see sheer encouragement. She always believed in me in a way that maybe didn't make sense at the time; it was a little bit illegible. When we were writing together, it truly felt as though we were improvising. There is a line Patti Smith writes about her friend Sam Shepard when she is learning how to improvise with music. He says, "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." That quote is so relevant to our friendship. Whenever I was stuck or lost or listless, Justine would say, "Let's keep going." We wrote 30 pieces together. That's a lot to write with another person, let alone by yourself.

Jackson: (1:29:55) It is an amazing attribute when someone makes you feel like things are possible, like there's road ahead. It makes it easier to step.

Nicole: (1:30:10) I also want to impress my friends. I trust their judgment and I want them to feel proud of me as well.

Jackson: (1:30:21) It's a good reason to have high standards. Maybe this applies to Justine, or maybe just broadly, but Hua Hsu writes in Stay True that friendship rests on the presumption of reciprocity, of drifting in and out of one another's lives with occasional moments of wild intensity. This points to something I feel deeply: friendship is this strange relationship where there are no obligations or rules. The farther you get away from the confined school parts of your life, the more you realize that your best friend could tell you on a whim they're moving across the country, and if you protested, it would be weird. If a romantic partner did that, you'd be a sociopath. How do you relate to that with people in your life who you aren't in active proximity with?

Nicole: (1:31:17) You're pointing at something deep and true about friendship, which is that it's under-theorized as a connective tissue. Anyone can be a friend in some ways. People can be friends and collaborators and all of these different things. I think it's actually about soul resonance. If I feel that I understand someone's character and soul and what they are put on this earth to do, that bond is actually very difficult to sever. Justine lives in London, and we honestly see each other in person maybe once a year. I'm actually seeing her in two weeks, but we don't have a lot of surface area. However, there's a lot of density. It's similar to us, Jackson. We see each other not that regularly, but when we do, we go on three-hour walks. It's depth of friendship rather than breadth.

Jackson: (1:31:30) What are we? Are we friends yet?

Jackson: (1:32:23) One of my theories is that people deeply underrate proximity in relationships. You can talk yourself into the idea that you had this really meaningful walk, but I've gotten back into proximity with old, very close friends and realized it's a little different. I thought we were as close as ever, but when you get back into extreme proximity, you realize the dynamic has changed. Proximity can be maintained with a very close friend here and there, but it is difficult.

Nicole: (1:32:50) How do you think of mental proximity? I understand physical proximity, like living next door to each other, but how do you think of always being in each other's orbit?

Jackson: (1:33:02) It has to be non-intentional. If you're in an active group text with multiple other people, it works differently than a one-on-one. I have two of my best friends, Brenner and Andrew, who were big parts of me doing this podcast. For the first five years of our friendship, we didn't live in the same city, but we had a very active group text. That is different than saying, "Hey man, we should catch up." Intentionality matters, but for most relationships, if you don't live in the same city, you need to have some kind of rhythm.

Nicole: (1:33:40) Maybe there's some threshold you have to meet to even consider yourself close—enough exposure therapy to that person.

Jackson: (1:33:49) The physical version of this is wanting to run errands together or sitting in the car and not talking for an hour. That is a level you can't really get to with only intentionality.

Nicole: (1:34:00) Blank space time or white noise time might be the term for that.

Jackson: (1:34:07) I thought it was so cool and lovely. Do you have any thoughts to share on Linda Montano and Tehching Hsieh tying each other together?

Nicole: (1:34:20) I loved that art piece. They actually tied a physical piece of rope to each other for 365 days, which is insane.

Jackson: (1:34:30) And they weren't allowed to touch. They weren't lovers, either.

Nicole: (1:34:35) They were just friends. I hope they can call each other friends; it would be awkward otherwise. Talk about proximity! Many performance art pieces say something very true about the nature of connection. Part of that piece was exploring what they did there. There was a piece of paper they signed which said, "We will never be apart."

Jackson: (1:35:10) That would be quite crazy. For some reason, it makes me think of Marina Abramović.

Nicole: (1:35:24) Which one? The one where she is sitting and her old collaborator appears?

Jackson: (1:35:28) It is the extreme antithesis of those two former, incredibly dense connections. It would be like if these two people were in love and didn't see each other for thirty years—that is a moment.

Nicole: (1:35:41) Marina Abramović's work is really about human nature. She also does one where you can do anything to her, and you see people do things where you are a little shocked. It is really about what happens when all these false pretenses of civility go away. There are dark parts to human nature that she portrays quite well.

Jackson: (1:36:07) Related to friendship and love, you say complexity means appreciating the critical difference between love and attachment, between fantasy and reality. We experience friction when we are faced with the inherent mystery or unknowability of another. This ties to our conversation about reality and fantasy. You recommended a short story to me called "Closer" by Greg Egan. Why is the unknowability of the other so important and so beautiful?

Nicole: (1:36:38) I am curious to hear what you thought of it. The story is from the book Axiomatic, which is a science fiction collection. "Closer" is about a couple where one of them wants to constantly get closer to the other person. They undergo a transformation where you can take someone's brain and put it into another person to inherit all of their memories, essentially becoming a union. The moral of the story is that it is the fundamental unknowability or the mystery of another person that interests us. It is a very romantic idea to constantly be surprised by another person and to be seen in a different way by them. There is a quote that marriage is like one long conversation. Part of a conversation that keeps it going is that you don't know what the other person is going to say next; there is some surprise. Relationship theorists talk about the dynamic of maintaining both mystery and familiarity. Those are two poles of tension that you need to keep in a relationship. That short story does a great job of exploring what happens when you don't fully know another person and why that is beautiful. You can surprise another person, and you can also surprise yourself.

Jackson: (1:38:16) You can surprise yourself by way of them. That story is a beautiful example of how reality is more beautiful than fantasy. You also 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, symmetry, or pleasantness lacks real intimacy. It is 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 inimitably beautiful." My reaction to your prompt about "Closer" is an old idea from a friend who says that in a relationship, you have to decide whether you'd rather be bored or annoyed. It's not quite the same, but there's an element of wanting both. You want to be deeply seen and known and have more intimacy, which by definition is knowledge. Yet, as someone who doesn't want to be bored, we need to be surprised. Reality is surprising, even if it is abrasive.

Nicole: (1:39:40) It is very important to have the mindset that you can and will change. Anticipating change is also really important. I really love a particular piece by John Repetti called "Yet Byron Never Makes Tea as You Do," which is about his wife. I've quoted it so many times; I hope John Repetti is not annoyed at me.

Jackson: (1:40:04) I have that right here.

Nicole: (1:40:04) He talks about seeing the chip in his wife's front tooth and being so enamored with the story of that tooth. From the outside, it might look like an imperfection, but to him, it was proof of humanity. The title comes from a line in a Virginia Woolf novel. The point is that you do all these things like Byron, but Byron never makes tea as you do. You spill the pot and mop it up carelessly, and you put the pot in a different place. All these little quirks are a little bit annoying, but that's what makes you so inimitably you that if you were gone, I would weep. It is a beautiful piece.

Jackson: (1:41:07) One of my favorite bits of that is: "Love begins not with me, but with the other, with the little eruption of the real that I experience in the other."

Nicole: (1:41:14) It's so good.

(1:41:18) Closing Notes: Solitude, Noticing, and Aliveness

Jackson: (1:41:18) Just a few more things. You have a line where you say, "I spent a lot of time alone finding myself in the chasm between solitude and loneliness." What's the difference between solitude and loneliness? What is that chasm?

Nicole: (1:41:33) The chasm comes from the fact that you can feel really alone in a crowd of people. You can be surrounded by people and still feel lonely. In terms of solitude, you can feel really held and seen by a lot of people while you're actually doing your own thing. You can have a vibrant, beautiful community of people that love and care about you, but you're just going to do your own thing. The difference is whether you have people who really understand and hold you, so that you can be free and alone.

Jackson: (1:42:13) Choose to be alone. What is the chasm? You're dipping in between those two.

Nicole: (1:42:19) Sometimes you forget. You think you're just an individual person in the world, and then you realize that you are built up of all these other people. I'm basking in the grace of all these other people around me.

Jackson: (1:42:37) I thought you were going to go the other way, which is when you are willfully in solitude and you forget and get lonely.

Nicole: (1:42:45) I think that's also true. You spend enough time alone and you start to feel like you chose this. I promise I chose this. It's why I can never really go on a silent retreat. I love solitude, but I think that's a little bit too much solitude.

Jackson: (1:43:03) People talk about things they most regret. What are you most glad you did?

Nicole: Writing online. It has given me a way to see the world that is so fundamental that it's difficult to imagine my life without the role writing has played in it.

Jackson: It probably makes it easier to trudge through the mud when it's feeling muddy. You remember that. Here is what I like in people: perceptiveness, humility, wit, a feverishness toward good ideas, high conviction, an iterative process of self-understanding, and equanimity. It's easy to distill this into language, but it's hard to notice these things in real life. I think one of life's greatest skills is being good at noticing. How have you improved at that? Or in the people who you really admire, what drives that? It relates to the attention and beauty stuff, but noticing is a specific word.

Nicole: (1:43:37) I read a book recently called A Swim in a Pond in the Rain by George Saunders.

Jackson: (1:43:50) I have it on my shelf.

Nicole: (1:43:51) I think you'd really like it. One of the main points he makes is that every person in his Syracuse MFA class on Russian short stories has come to him already perfect, and he's just helping them find their singularity. The whole book is a deep reading of Russian short stories and why they work. To notice deeply means to notice how you feel about a thing and come to a worldview about it, or about a person or a piece of writing. It means understanding the emotional reactions you have and the interrelationship you create with anything you consume or make or any person you relate with. Noticing that dynamic is really important. Some conversations and some people make you come alive and create a new, special world with distinct taxonomies and characteristics. In living in that world, you experience a new type of feeling or a new way of living. Noticing is noticing the interrelationships a lot.

Jackson: (1:45:13) Noticing the space between.

Nicole: (1:45:19) He calls it the supra-personal. Not interpersonal, not super personal, but the supra-personal.

Jackson: (1:45:28) There's a line in Before Sunrise where they're sitting in an alley and she says if God or magic is real, it's in the space between us trying to understand someone. A quote from Jeff Buckley in a piece of yours about feeling behind or things going the way we think they ought to: "Life has its own rhythm, 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 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 or control it. How do you loosen your grip?

Nicole: (1:46:17) If you look at the through line of my writing over the last four or five years, you'll see I've gone through a lot of peaks and troughs. I'm not afraid to say that this is happening, and I'm going to write it down. The act of documenting and creating little signposts in the journey of life is important to remember that you can't control things. Even when I'm in the euphoria of having written a piece and feeling on track, I remember there are moments of great loss, despair, and listlessness. I always have to remember these minima and maxima.

Jackson: (1:47:04) You're setting anchor points.

Nicole: (1:47:05) You're setting anchor points and remembering that you can reach the maxima again. That is really motivating.

Jackson: (1:47:13) There is a little thing from Bob Irwin's biography we talked about earlier: "There is no such thing as a neutral gesture because that very fact of it being there draws a certain amount of perceptual attention. Let's say it drags a weight of .06. Well, then it's got to give back .12 in energy. Some are major moves, major gestures. Certain things are just support; everything doesn't maximize all the time. There's some trade-off. But I quickly saw there is no such thing as neutrals." It had me thinking about the modern era, where it's so easy to do everything. Where did detail and craft come in? These little subtleties made me think of you, and it feels like a beautiful philosophy for the little nudges of things. I was curious if you had a reaction.

Nicole: (1:48:20) I have a physical copy of Seeing Is Forgetting the Name of the Thing One Sees. It's about the ineffable feeling you get when you see or understand something. It's not exactly explainable, but I underlined that line furiously in the margins. It's important to care about what you put out into the world and care that it's making a statement or sharing a perspective, rather than having it be a waste of space.

Jackson: (1:49:00) Every little guy just drew lines all day. Every little flick matters.

Nicole: (1:49:09) Small things aren't trivial, especially if you're attuned to them or you notice them.

Jackson: (1:49:11) It's easy to not notice when you've lulled yourself into focusing on maximizing output. You mentioned Miyazaki, one of my favorite quotes you've ever sent me, on 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. Should you ever relinquish what you truly hold dear, the only path left to you will be that of a pencil pusher: the type of animator whose sense of self-worth is determined by the numerical amount of their earnings, or who cycles between joy and despair over the high or low rating his work receives." This is related to what we were speaking about just now with Bob. Maybe the thing there is about personal standards independent of anybody else—maybe even an autotelic aspect of it. I think the most interesting question for you would be about writing. What keeps you pushing?

Nicole: (1:50:22) That quote is from a moment we were talking in New York on a long run. I have that saved in my phone and I return to it frequently. It comes from his book Starting Point, which is about the first twenty years. It's funny and telling that twenty years is a starting point. You will always have the knowledge within yourself of the craft that you're making. You will always know how much work 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. When you can actually point to things that you did—the means is the end, basically—in the process of choosing and creating, you have the standard for yourself that you meet, and it makes you proud. Creating is always in that middle ground of the process of making the work, rather than the final outcome.

Jackson: (1:51:36) Two final quotes. "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, and frown. How could I expect us to stay the same? I like a line I heard in a 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: "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, 'Anything you do not give 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 at some point in the future. But writing is a deep well that continues to be refilled by life experience, reading, and observations. Use every good sentence you have written now. Burn the candles." It feels very fitting, something that came up repeatedly throughout this conversation. How do you remind yourself to stay so abundant and so generous?

Nicole: (1:52:44) It's viewing creativity and the soul that you put into your work as renewable. Ursula Le Guin has this line that love is like bread, remade every day, made new. I think the same is true for creativity. There are always going to be more inspiring things to read in the world or to ingest. We forget. We think there's a finite number of interesting people to talk to or that we only have so many good ideas. But actually, the deeper you go, the richer it gets. Reminding myself that no matter what I do, I will never reach the bottom of this well is something that really drives me forward and is very meaningful.

Jackson: (1:53:32) It shows in the work and the way you approach things. It's an honor to do this. Thank you.

Nicole: (1:53:37) This was so fun. Thank you, Jackson.

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