4: Ava - Alive in Writing and in Love

Speaker A: Ava is one of my favorite writers. She writes full-time for her Substack, Book Bearer Express. I'm not sure there's anyone I've more consistently recommended to friends and loved ones in recent years, and it seems like the world agrees. Ava now has over 30,000 subscribers. One of my favorite parts of this episode was reading excerpts from Ava's essays over the years back to her. We cover a ton of ground, including writing, consistency, commitment, friendship, authenticity, self-respect, taste, beauty, and much more. Please enjoy. And if you've liked the episodes thus far, please follow and rate them on Spotify or Apple.

Here's Eva. We're here. Speaker B: We are. Speaker A: The queen of Book Bear Express herself, live in San Francisco. Not live. Well, I guess we're live. It's wonderful to be with you. How are you doing? Speaker B: I'm doing well. I'm excited to have you here. Spending more time in San Francisco. Speaker A: This is all part of your ploy. Speaker B: I'm hoping that on this podcast you'll make a commitment to moving to San Francisco. Speaker A: Oh wow. All right, we, we, we have to get through a few things before we get to that.

Okay, I did a little digging. For the viewer's context, or the listener's context, not the viewer, I met you on Twitter because I read your writing and I reached out and I wanted to go back and see what was inside of that. What was that message? I'm going to read— Speaker B: Your cold DM to me. Speaker A: I'm going to read my cold DM and a quote from something you wrote that maybe I think, in some ways, I think really sets the stage for what I think makes you as a person special and makes your writing so special.

So I had said, "Hi, dropping a note to share how much I've enjoyed your writing. I discovered it only recently. Your perspective on the ordinary and seemingly mundane is particularly wonderful. So I really love today's essay." I like this bit in particular. This is you. Maybe to you, something like this isn't worth getting excited over, but I find that people who tend to reserve specialness for very particular things tend to be disappointed by those things anyway. I'd rather be easily excited by everything I like. You, for those of you, excuse me, for people who don't know you, you're primarily a writer.

Speaker B: Your cold DM to me. Speaker A: I'm going to read my cold DM and a quote from something you wrote that maybe I think, in some ways, I think really sets the stage for what I think makes you as a person special and makes your writing so special. So I had said, "Hi, dropping a note to share how much I've enjoyed your writing. I discovered it only recently. Your perspective on the ordinary and seemingly mundane is particularly wonderful. So I really love today's essay." I like this bit in particular.

This is you. Maybe to you, something like this isn't worth getting excited over, but I find that people who tend to reserve specialness for very particular things tend to be disappointed by those things anyway. I'd rather be easily excited by everything I like. You, for those of you, excuse me, for people who don't know you, you're primarily a writer. Speaker B: Yes. Speaker A: Singularly, not singularly, you contain multitudes, but you are professionally a writer and also do do a lot of writing in your kind of life broadly. What makes for good writing?

Starting with the easy ones. Speaker B: Wow, really starting with the easy ones. Speaker A: Or at least what makes for the type of writing that you really enjoy? Speaker B: I'm definitely a sucker for a great prose style. I don't think I could define what good writing is, but definitely great prose, clarity of thought, attentiveness I think is a big one. I really like writers who have this particular attentiveness with which they perceive the world and sort of like get it down on the page. Speaker A: I think that checks out.

You've been writing now in some form on Substack for 4 years? Speaker B: 4 years, yeah. The anniversary of 4 years was September. Whoa. Yeah. Speaker A: Big one. Okay. I'm curious, looking back, both what you think the holistic themes have been or that you continue to come back to, and then also if there's any notable way you've observed that they have changed over the course of 4 years. Speaker B: Yeah, I definitely— I think I started out writing my Substack thinking it'd be a bit more about mindfulness. So like that year, 2020, had kind of been a year where I'd started to get a lot more interested in like psychedelics, meditation, and some of my earliest posts were kind of like born out of a desire to like share more about that.

But I quickly found— I think a lot of people— I think Sasha Chapman had just recently wrote a great piece about this— it's actually very hard to write about mindfulness, or I personally find it very hard. And so I think it kind of started in that place and kind of became more holistically about just the things I'm interested in, um, which I would define as like personality, emotions, psychology, culture, relationships. Speaker A: I don't— I don't— Speaker B: I— Speaker A: you obviously have some cool psychedelic stuff, but I didn't know it was that.

Mine— it also checks out, I guess, for 2020, September 2020. Speaker B: It was definitely a big, like, a, a big focus at the time and something that's still— it— meditation, mindfulness is definitely something I think more about and maybe talk to friends more about than I write about. I think it's like very accurately perceived that sort of like talking about your dreams, like It's only really interesting to people who are in the know and then like, mm, it is sort of boring to everyone else. Or at least I just have not gained the requisite level of skill needed to write compellingly about it.

But yeah, I, I like to think of it as one of the undergirding themes of my work more than something that I explicitly address so often. Speaker B: It was definitely a big, like, a, a big focus at the time and something that's still— it— meditation, mindfulness is definitely something I think more about and maybe talk to friends more about than I write about. I think it's like very accurately perceived that sort of like talking about your dreams, like It's only really interesting to people who are in the know and then like, mm, it is sort of boring to everyone else.

Or at least I just have not gained the requisite level of skill needed to write compellingly about it. But yeah, I, I like to think of it as one of the undergirding themes of my work more than something that I explicitly address so often. Speaker A: Yeah, yeah, yeah, yeah. That makes sense. And you primarily write about yourself and your life. Has that part of it changed materially? Speaker B: Yeah, I mean, I would say that I've never written about myself very explicitly, and that's always kind of been the case.

But like centering the Substack around like maybe like my life and my emotional experience has always been, I think, true from the start. I think that was always sort of the lens through which I found it easy to write. And I think it's been really good as sort of like a theme or a perspective for me because like, you know, You can always sort of write about your first-person experience, so it remains like, yeah, yeah, I didn't want to pick a topic that I might run out of steam on, and I certainly didn't.

Speaker A: Yeah, to be clear, you don't write about like necessarily about the plot of your life. Yeah. But you are very inside of your writing, your feelings, all these things. One thing that in kind of getting more a little into the actual process of writing, You wrote something, I don't know, maybe last year about flow and maintaining flow and protecting flow. And there's a line in there that I think about all the time, which is that your life can be mostly flow. I don't know how that's obviously, I think, more aspirational than anything, but can you talk a little bit about that and your, maybe your writing practice and how writing fits into your life?

Speaker A: Yeah, to be clear, you don't write about like necessarily about the plot of your life. Yeah. But you are very inside of your writing, your feelings, all these things. One thing that in kind of getting more a little into the actual process of writing, You wrote something, I don't know, maybe last year about flow and maintaining flow and protecting flow. And there's a line in there that I think about all the time, which is that your life can be mostly flow. I don't know how that's obviously, I think, more aspirational than anything, but can you talk a little bit about that and your, maybe your writing practice and how writing fits into your life?

Speaker B: For sure. I mean, for context, I was reflecting on this recently since I've now I've been writing the Substack for 4 years. I feel like I actually started the Substack at a time where I had a lot of questions about my own ability to commit. So background context for the listener, you know, I dropped out of college when I was 19 and worked on a startup for a couple years and, you know, that didn't work out. And I sort of like bounced around trying to figure out what I was going to do with my life.

And I sort of very much had the sense kind of in my early 20s where I'm like, Oh my gosh, like, I, you know, maybe I'm just like too ADHD. I have all these like things I find interesting in the world and I've, you know, taken a stab at a couple of them, but like obviously like I haven't fully committed to any. And, you know, am I just going to become this person who has a lot of potential but doesn't really actualize all of it? And then, you know, I'm just kind of doomed to this kind of like fragmented existence of like never mastering anything.

Um, that, that was kind of like something I was very like afraid of. And I think in that sense, like starting to write, which was something I totally fell into, like it wasn't really— I mean, it'd been always something that was a passion of mine, but I did not even start doing it consistently thinking it'd be a career. But I kind of like just writing consistently and then committing to it was a big turning point in my life where I actually started committing to a lot of things. And so, you know, 2021, that was I was a couple of years into what would become like quite a long-term relationship at that point.

I had, you know, started my writing practice, um, I'd started kind of really getting into mindfulness, uh, I'd kind of like gotten, um, much more serious about yoga in the past like year at that time, which is still a big part of my life today. And so like I really look back at that time and was like, oh, like it was really a turning point for me where in that year, 2020, 2021, I started doing a lot of things that are still a huge part of my life today. And I think through that, um, it changed my life in two ways.

One, like, I was able to kind of shed what, you know, what was just a fear. Like, why I feared was kind of like my whole identity. But like, you know, I was able to kind of be like, okay, I don't need to conceive myself as someone who's always like bouncing around but never able to commit to things. Like, I truly just had not found the right thing to commit to yet. And like, so I could kind of let go of some of my anxiety around like, am I this person who's interested in things but can't do things?

And second of all, I think this like flow state thing you talk about, um, I do think the number one argument for commitment is like, you can find flow in doing something repetitively that you just cannot find when you're doing a million different things. Like, I think at this point, like, for me, whether it's yoga or writing or just like living my home, like, I have a particular setup, and I do it pretty much every single day. And I do frequently find myself in flow states when I'm, you know, engaged in these activities, which can be as simple as like, you know, walking to the dog park, getting coffee, coming back and like writing for a couple hours, like going to yoga class in the late afternoon.

Like, and it's just because I identify things that made me feel a particular way and were very generative, and then I just kind of kept doing them. And like, turns out you can just keep doing that and it just works, and there's no reason it has to stop working. And so like, yeah, that feeds pretty well into this other thing. Speaker A: I think maybe the first thing I ever read of yours that I really loved, which is this post on maintenance, which is— it's not exactly, but I think in some ways this counter feeling to the desire the noncommittal desire to have novelty in everything.

You have a little excerpt that I wanted to, to read that I think hits this well, which is, but I try to maintain what I care about most. And the act of maintenance is what helps me sculpt a cohesive self. To know you have to keep showing up forever and still choose to put in your most earnest effort each time feels Sisyphean, but on certain days it also feels like pure relief. Is there an element of this? Obviously you described this kind of amazing idealistic lifestyle of somebody who has rhythms and creative work and flow and all these things.

When that isn't going as well, or when you're rubbing up against the friction of feeling like it's maintenance, or you're stuck in kind of the messy middle of a project, or frankly creative inspiration at all. How do you relate to that? Or do you have an energy source you go to? Do you just kind of trust the process? Are you just better at returning to maintenance out of habit now? Speaker B: I think it's really liberating to just realize that a lot of the time you'll feel like something isn't going well.

I think that's kind of the most important thing for me where, you know, when I think about like, okay, writing a Substack for 4 years, or like I've been working on a novel for like almost 5 years at this point. And it's like, you know, I'm actually with both. Currently in a place where I'm like feeling quite like— I feel like they're both going pretty well. But like for large chunks of, you know, years, I spent like, you know, it's very normal for me to spend 6 months just being like, I don't really like the place Substack is in, like I don't feel inspired.

And that, I think, coming into that and out of that has just made me realize like that is sort of what your relationship to doing the same thing and again and again sort of is, right? Where like In the beginning, you might be like, okay, I felt bad about this for 3 months, maybe this is a sign to stop. And I think like once— Speaker A: 3 months is a pretty long time, all things considered. Speaker B: Not that long, but it's not, it's not. Speaker A: No, that's the other side of it.

Speaker B: Like, it seems like a long time, but like, I think like when you're— for example, if you've done something for 5 years and you're like, okay, like I've, you know, cycled in and out feeling good and bad about this for like most of that time, and like it's very normal, and then you're kind of like 3 months is nothing. Even feeling bad about something for a year is like nothing, you know. I think just having the perspective that like, you know, something I think should always feel rewarding and meaningful, but like the actual practical thing, it's okay if it just doesn't feel like it's going well.

That I think can be very discouraging. But for me, like normalizing that to myself has been the biggest thing where like everyone feels this. This is a normal thing to feel about your work or your hobby or anything you're working on. Actually, like feeling demotivated and frustrated with something is just part of the process. Speaker A: Our mutual friend Jason, who was on episode 1 of this podcast, has this line that confidence is the memory of success. And I suspect part of what you just described is knowing that there have been— yeah, 3 months, if you're starting out, 3 months is an infinite amount of time.

If you've been doing this for a long time and you have a 3-month dry spell, that's a different thing. And I suspect a huge part of this was finding getting to the point with writing in 2020 or earlier in your life or whatever it might have been where you at least knew, one, I can find flow in this, and two, on some level I'm good at this, I like this or whatever. And that makes it a little easier when you feel like you're in the middle of the storm or it's really tough or whatever.

Speaker B: Yeah, I was just discussing with a friend who's also a writer that many writers have kind of the setup I have, which is they have one more long-form project that maybe not a lot of people have seen, or they don't get a lot of validation on, and they have kind of like a personal blog or a Substack where they do freelance, you know, articles or something. Like, I think it's very common, probably not just in writing, but I imagine like in many kind of like creative professions, to sort of have some way of getting feedback or getting validation even when you're engaged in something else that's like sort of like this black hole.

So I find that, yeah, I think I think everyone needs confirmation that they're doing something right occasionally. It's very hard to continue without that. Speaker A: Yes, I agree. Okay. I want to ask you some questions about audience and specifically the kind of like professional side of what you do. Obviously you are a writer. I think if Substack was banned and the novel, you weren't allowed to, somebody told you you weren't allowed to write professionally. My suspicion is you would continue to write. Every day. That said, especially given the nature of what you do, which is this, again, not necessarily like about the details of your life, but very personal writing.

I think my experience of your writing is somewhere between, sometimes it feels like journaling, sometimes it's a little bit more performant and it's like an essay. Sometimes it's self-help. Sometimes you're teaching. Sometimes you're just reflecting on your own experiences. Sometimes it's entertainment. There's, there's all of these things kind of swirling in there. And obviously your audience size has also changed. And now you're at a point where there's tens of thousands of people probably subscribe to you and people paying you and all these different things. One, I'm curious just how you relate to something you love so much creatively also being work.

Oh, it's a classic story, music, whatever. People, some people are fine with that. Some people really struggle with that. Has that been challenging to navigate or has it been? Pretty coherent? Speaker B: I think that for the most part, like, I really like what I write about, and I'm lucky to have a job that, like, truly is joyful for me. So I think— I, I feel like I definitely think of myself as, like, having it easy just because I'm genuinely writing about something I find very engaging, and, like, I get to do something that's, like, you know, a lot more authentic, quote unquote, to me than, like, a lot of people find their day jobs to be.

Speaker A: Yeah. Speaker B: At the same time, I Actually, I ran into this very sweet reader who was asking me about like whether my writing style has like changed as I've spent longer on the Substack. And I definitely think there's an element of, you know, you do write for your audience, or at least like I am influenced by my audience, right? So like I think there is like a level now of like I want to write something that my readers will like and I have some understanding of what they're interested in.

And you know, you're trying to cater to like what is useful or interesting or compelling to them. Yeah. Which is, obviously different from like writing on a Tumblr for yourself, right? And so I think there is sort of more of a shift over time to like wanting to deliver, which I think is sort of inevitable for anyone who's a creator or like basically makes money from their audience. Speaker A: You've also written about this, maybe the tension between actually living and the desire or the temptation to record or capture your life.

Um, maybe this is something that you've gotten better at over time. I think anyone who does anything creative, this— there's a little bit of this. I don't know, I'm, I'm now recording conversations with my friends. Has that— is that a part of that, or is that something that's gotten easier over time? Speaker B: Yeah, I don't think I write, um, like, you know, one-to-one about life events, so I think it's sort of easy for me, like, in that sense, where, like, you know, for people who are, like, journalists or something, like, you actually have, like, assignments where you might go to this event or something, you literally need to write about it.

Like, I usually don't have anything like that going on. I write more about like emotions or themes. I think I'm lucky in that, like, I never usually in a situation am like, I have to write down the dialogue I'm overhearing, or I have to like write down notes about like this hotel or something. Writing versus living, I— hmm, yeah, I do think that it can sort of— I, I always say I think the most tiring thing about like doing something like Substack is that you truly cannot take time off. I mean, you can, but like I think most Substack writers would agree with me that from like a revenue point of view, like people don't like it when, when writers take breaks.

Right. And I think there is kind of this pressure where like, you know, I don't write on a crazy schedule or anything, but the thing is like, I don't really feel like I can stop. There's probably like a couple, a few weeks a year where I'm like, okay, you know, Christmas week or like I'm just really busy with some personal thing. I'm like, whatever, I won't write for a couple weeks. But like most of the time I really do feel like I need to stick to my writing schedule no matter what.

Speaker A: So twice a week? Speaker B: Twice a week. Sometimes once a week. But I think, and it can feel like, oh my God, like, okay, let's say it's like Thanksgiving week and I'm just like sitting around. I'm not reading anything interesting. I'm not like thinking anything interesting. I'm not like feeling any emotions are particularly worth writing about. And then it can be sort of funny to be like, okay, like I don't feel like a wellspring of inspiration right now, but like the post must go out, you know, like it, the post must go out.

So like you really, I think the challenging thing is that, you know, I think you do have to be professional about it and There's nothing wrong with being professional about it, but I think sometimes people underestimate it. I think this is even outside of writing. I think the content grind is sort of just like this, right? Where like a lot of content creators will say like, you know, everyone thinks it's not real work, but once you realize like you have to keep producing content all the time, all the days of your life, like it actually does end up feeling kind of, it becomes just something that you hold yourself to and need to do.

Speaker A: Yeah. Especially when you're, well, I'll, I will say your, your Thanksgiving, your Slow Thanksgiving week post this year was really, really great. If people want to go, it was called December. Oh, one of my favorites in a while. One element of that last bit too with the content creator stuff is like anything personal, you're going to have a different— there's pros and cons. Obviously if you're a journalist, you go, you have to go interview people that you talked a little bit about that. But on some level, like what you do is vulnerable.

Obviously I think you found what seems to be a pretty good balance there in terms of how vulnerable to be and how much you write about. I am curious how you think about, or how you even experienced wide vulnerability versus narrow vulnerability, meaning, um, the type of vulnerability that comes across writing to theoretically thousands of people online versus talking to a friend. I would, my suspicion is most people who read you would say you're incredibly vulnerable, at least in some dimension. Again, you're not talking about people or specific events, but that's a different kind of vulnerability than talking to your friend about a relationship or whatever it might be.

Speaker B: Yes. I mean, I find this very funny because, and I don't know if you think so, Jackson, people actually often give me the feedback, like in real life, that they wish I were more vulnerable. Speaker A: In your writing or just in general? Speaker B: In my personal life, like with close friends, for example, or in relationships. Like, I have been told kind of, um, I, I forgot if we talked about this, but like, I think things have gone like, okay, like, you're a little bit opaque. Like, I feel like you're more comfortable like hearing about other people's problems and talking about your own.

Like, you know, I've definitely been accused of being afraid of vulnerability, you know. Uh, and so I, I, I do find it kind of interesting that I sort of have a career of being in some way like professionally vulnerable. Speaker A: In your writing or just in general? Speaker B: In my personal life, like with close friends, for example, or in relationships. Like, I have been told kind of, um, I, I forgot if we talked about this, but like, I think things have gone like, okay, like, you're a little bit opaque.

Like, I feel like you're more comfortable like hearing about other people's problems and talking about your own. Like, you know, I've definitely been accused of being afraid of vulnerability, you know. Uh, and so I, I, I do find it kind of interesting that I sort of have a career of being in some way like professionally vulnerable. Speaker A: Yeah. Speaker B: But like, that's not really, to be honest, like that's not like a label I would apply necessarily to my own. It's not necessarily like, I think to me it feels like I'm like unqualified to claim like my writing is vulnerable or like, you know, to say something like, am I vulnerable or not as a person?

I think that's sort of more of like an adjective that other people can place on your work. But it's not something, I don't sit there and go like, well, is this piece of writing particularly vulnerable? Like that's not really an axis on which like I think about I don't know, my work for myself. I think probably maybe like I think a little bit about like sincerity. I think that's sort of important to me, and I think the two are linked for me. Like, I think one thing I do care about is like that my writing is emotionally honest, even if I'm not disclosing the details of my life.

I, you know, try to mostly write things as I experience them because like that is important to me, that like I'm accurately portraying something I'm going through. Yeah, maybe the sincerity is vulnerable in a way, but like, I, it's, I think it's sort of hard from the inside to, to say, is it vulnerable? Is it not? Like, I find that hard to assess actually. Speaker A: Well, and there's, this comes in different, vulnerability comes in different flavors. There are probably artists out there who, if you spend time with one-on-one, you would experience them as almost as like a brick wall.

And yet their art is like profoundly vulnerable and meaningful and I don't know, I certainly relate to being someone who asks other people lots of questions and also does a performative, maybe not entirely performative, but like, I'm fairly open in some ways, but there are different ways we like almost pick our spots on vulnerability. And I think that's probably fine. Speaker B: Right, I mean, I certainly think like the act of making art is very vulnerable. Speaker A: Yes. Speaker B: Right, and so like, it is, yeah, I think maybe saying like, writing is very vulnerable for me.

Is my writing itself vulnerable? Like, is a piece vulnerable? I think that's hard to assess for me, but I think I'm comfortable saying like writing is something like, I think the creative act for anyone is just very vulnerable. And so I think that's definitely a way in which I feel very vulnerable, like putting myself out there. And I think that maybe is easier to talk about than like, you know, is the Substack vulnerable? That's harder to say. Speaker A: And it gets to the sincerity thing too, which I think you nailed.

You've obviously met people because of your writing, including this interviewer. Um, and you've done meetups with your audience. You've done some matchmaking stuff. Has your audience become— one, it's grown also a ton, but has it like, has it taken more of a shape in your mind? Like, do you, do you think about who your audience is? You, you maybe alluded to this briefly earlier, especially now that you've started to put more faces to it or you're starting to see people's names more. Speaker B: For sure. I mean, I feel, hmm, like, I think one thing that I was really surprised by as I started to meet more people who read my writing was like how many of them are just people I want to hang out with.

And many of them— Speaker A: it's a bad signal. Speaker B: I do, I do hang out with them, you know. And so I feel like incredibly comfortable at like meetups or through all the things I've done through my Substack, just because I like really like my readers turns out. And like, that's been like a really pleasant surprise. Like, I just, I think when I started writing my Substack, I didn't really know who the reader was. And it's really only in the past year or so that I really started meeting like a lot of people who read my blog.

And yeah, turns out I really like them. Um, I'm a big advocate of the idea that like putting out personal writing is like one of just the best ways in the world to meet friends, partners, people you admire, work. Like, it's like, it's unilaterally, I think, one of the most powerful things you can be doing. Speaker A: Yeah, well, you, you give some vulnerability and you get a lot in return. Speaker B: Definitely true. Speaker A: You— do you have this, like, are there any broad strokes, sweeping kind of categorizations or themes on the audience that you would, that you've noticed in terms of the type of people, like the caricature of the, the Book Bearer reader?

Speaker B: Yes. Speaker A: Excuse me. Speaker B: I think one funny thing I like to say is that like people are so socially astute that at meetups I actually have the problem of like, I feel like not enough people talk to me because I feel like they're all so conscious of like not swarming me that like people are too considerate. Speaker B: Yes. Speaker A: Excuse me. Speaker B: I think one funny thing I like to say is that like people are so socially astute that at meetups I actually have the problem of like, I feel like not enough people talk to me because I feel like they're all so conscious of like not swarming me that like people are too considerate.

Speaker A: So like alone in the corner. Speaker B: Yeah, you know, like really considerate, really conscientious, like very emotionally intelligent. I would say 20. Well, it's biased because I think younger people are more likely to come to events. But like, I would say like 20 to kind of like late 30s is like most of the— that's kind of the age range for people who at least I've met in person. Um, though there are people who are older and younger. Actually, a lot of them are Asian, which is what's kind of interesting to me because, I mean, I obviously am public about the fact that I'm like Asian Canadian, Asian American, but like, it's— I don't explicitly write about, for example, being Chinese like that often on my Substack, but it's been really interesting realizing like a really large portion of my readers are, you know, for example, Asian American.

So that's been really cool to see. And then there's really like a mix of professions. I'd say there's a lot of people in tech because that was sort of my original Twitter following. But there's tons of people who are like teachers, lawyers, like there's quite the spread actually. Location also, apparently there are people all over the world, which is really cool. And the gender balance is I'm very proud of this. Almost exactly 50/50. Speaker A: Wow. Speaker B: Yeah. Speaker A: That's quite rare on the internet. How do you know how you're getting, or excuse me, how do you know if you're getting better at writing?

Obviously you have a massive following, relatively, quite a large following for a writer online. You have your personal relationship to writing. It's been up and to the right from a growth standpoint. Is that something you're thinking about or do you just have an internal compass that's a little bit more implicit of I'm looking back at the last 6 months or 12 months and my sensibility, or are you not even thinking about the writing in that way? Speaker A: Wow. Speaker B: Yeah. Speaker A: That's quite rare on the internet. How do you know how you're getting, or excuse me, how do you know if you're getting better at writing?

Obviously you have a massive following, relatively, quite a large following for a writer online. You have your personal relationship to writing. It's been up and to the right from a growth standpoint. Is that something you're thinking about or do you just have an internal compass that's a little bit more implicit of I'm looking back at the last 6 months or 12 months and my sensibility, or are you not even thinking about the writing in that way? Speaker B: It is really complicated because I think it is natural. I want the Substack to keep growing and I want people to like find my writing and I wanna feel like I'm doing a good job.

At the same time, because for me in some ways my Substack is also an outlet as well as a, it's a small business slash it's my job, but it's also my outlet. Speaker A: So it's art on some level. Speaker B: Yeah, I really struggle to like balance between wanting it to kind of feel like, you know, my original inspiration was like sort of the blogs I grew up reading, right? And I always wanted to kind of retain this like fun, lighthearted nature to it, right? Like I didn't want to turn into something where I felt like I had kind of sucked all the like spontaneity out of it by like committing to You know, I sort of wanted to feel like, okay, there are other places where I can, you know, be a perfectionist about my writing and like, you know, be very exacting about the way my prose is and like, like I can do that somewhere else.

But I sort of actually did not explicitly want my Substack to be that for me. But it's also hard, right? Because I want it to be good. So I think I am still trying to figure out that balance. I would say the sort of the way that I think about it now is like I feel like I've identified over the past few years, like, topics I'm really interested in writing about, such as friendship. And I think one way I track the success of the Substack is being like, okay, like, you know, if I'm writing about friendship, do people seem engaged?

Like, do I feel like I'm, like, going deeper into the topic? Am I, like, writing about it from angles that are interesting to me and seem to kind of, like, be compelling to the reader? And so I think I try to track it from, like, a Okay. In terms of the things or topics I'm writing about, like, am I sort of going deeper on those and still writing about in ways that are interesting to me? That's sort of the metric right now. Speaker A: That's cool. Do you think much about distribution specifically?

You're, you're, you're past the threshold from a, obviously you can make a living doing it. You're growing organically. People are telling other people about it, but also as an artist, as a creative on the internet, like distribution is really important. Speaker B: Yes, I think about it a lot actually. Um, I feel like the thing I always say to people is I would recommend like putting writing online to anyone. Like, you know, you— everyone should be keeping some kind of personal blog. Uh, however, I would not recommend like making a living as like a writer online to everyone.

And I think the, the distinction really is like, do you want to think about distribution, right? Because like anyone who wants to make a living as a writer is thinking about money, frankly. And thinking about money just means thinking about like, I'll think about things like, okay, should I, you know, cross-post part of the Substack to Twitter? Like, how should I format it? Speaker A: Can I post the link? Speaker B: Yeah. Should I do like, should I do subscription sales at certain times of the year? Like, should I be like, there's all these things that you sort of think about from like, how do I make sure other people hear about my writing?

How do I keep my readers happy? Like, how do I like, make it so that paying for my content is like worth their time, you know? And I think like, yeah, frankly, I think there are probably a lot of people who are great writers who are just like, I hate thinking about this, you know? And like, that's just not compelling to me at all. And like, yeah, that's okay. Like, I think that's very valid. But I feel like for people who want to do the whole internet writing thing, I think thinking about that is really important.

And I do like thinking about it. It's very funny. I I have talked a few times with James Clear, who wrote Atomic Habits. Speaker A: Yeah. Speaker B: He's obviously like the best at this and he, he's just like a, a really awesome person. But I remember like, you know, kind of asking him about like why Atomic Habits like, you know, has been as phenomenally successful as it is. And he's like, you know, like the thing is I'm like obsessed with all the different parts of kind of like distribution process and most people just don't care about that at all.

And like, Yeah, I think in general, distribution doesn't have anything to do with quality of writing, right? So you can be this amazing writer who cares nothing about distribution, but I think caring about distribution is probably hugely linked with how much your writing gets read on the internet or something like that. And for better or for worse, that's sort of what it is. Speaker A: Yeah, not only that, but there's the effort part of it, but there's also just the frankly, like the form factor fit part of it. There's types of writing that isn't gonna do super well with an excerpt on Twitter.

And I don't know, obviously your writing isn't like built for that, but it does do really well in that context. And that probably helped her. I don't know. I was talking to my friend Jordy recently. He'd started this new thing called Technology Brothers. It's like a podcast and they have, they've done this amazing job where they just print out tweets and read them. And like talk about it on Twitter. And it's the perfect format for Twitter. James Clear is obviously a master of this. He has a really successful newsletter. I think some of this too is like, maybe you have different products or different outputs for different contexts.

Your novel obviously has none of, you don't have to think about any of this. Maybe eventually you'll have to. And so maybe that's like the way you kind of like find the middle ground versus a daily or, excuse me, not a daily, a weekly Substack or biweekly Substack feels a little easier to do in a way where it's short enough, it can be shared around, you can read it. I'm not going to read 20,000 words twice a week, probably, but I probably will read 1,000 or whatever it might be. Speaker B: Yeah, I think some of the art I love the most is art that, like, does not sell, right?

Like, I really like poetry. And, um, I think Emily Nussbaum once said— she, uh, she's a very successful television critic, I think, for The New Yorker. I don't know if she's still there, but she, you know, was for many years, actually won a Pulitzer for it, but she, I think, mentioned once that like she used to be a poetry critic and she had to stop doing it because it's so depressing to criticize writing that people work so hard on that doesn't like commercially sell at all, you know? And like, I, I love poetry, right?

So like, I think I have a lot of appreciation and like love to consume art that really isn't like viable, you know, as sort of a product on the market. And I don't think that art should have to be viable as like a marketable thing whatsoever. But then there's kind of like also the matter of like how you personally as an artist make your living, right? And so like, I think anyone who does creative work sort of has to reckon with it, right? Where it's like, okay, well, can you like have a day job that's not related to your art or your writing and just like make stuff that doesn't have to make money on the side?

Or, you know, do you have, you know, one way of like making money through your writing, but then you have like another form of writing that doesn't have to make money? I think it's like everyone's always trying to find a balance. And with my Substack, like, I feel comfortable saying like, okay, like, yeah, like, for now this is like my primary form of income. It is important to me that like, yeah, like, I want people to like it, I want people to subscribe, all of that. Of course there's a part of my psyche where I'm like, okay, like, I also want to write in ways that like I don't even have to show anyone, right?

Or like it doesn't have to sell a single copy. And like, I think that's— it's okay to sort of have attention. And that's like, I think everyone sort of confronts attention and creative work, and it's like always just about trying to find the balance between like, can I make a living, but can I also have like space to do things that simply don't need to be like marketable in any way? Speaker A: And the cool thing too is if you compound a little bit and you grow, you eventually get to the point where you can say, hey reader, I want you to trust me.

You claim you like my taste. I'm going to take you somewhere you maybe didn't think you would normally go. And I think you've done a cool job of that too as you've navigated different things. One topic that at least you, you certainly write about, and I think the pie chart of our conversations, uh, not on podcasts is, is incredibly full of really like what makes people tick, what, like social psychology, like what is it about people? How do we see people more clearly? Is there a reason you think you're so, or maybe both of us are so intrigued by that?

Speaker B: I think we're both people who really love people, you know, and I think in our friend group, like, that is also— I think we're also friends with people who like just thinking and talking about people. I think for me it's always been like a fascination of mine from childhood, and I think that's a big reason why I read novels, right? Like, novels fundamentally are Novels are mostly writers, uh, making observations about like their own, other people's psychologies. I think that's one way you could like— yeah, you can think about a lot of different novels.

So, uh, for me, I think people are just endlessly fascinating, and it's just so interesting to try to understand like why do people do the things they do, why do they change sometimes and stay the same other times, like why does XY date Y, like why do people fall in love and fall out of love. And I feel like you share those preoccupations too. I think It's just like endlessly— people are so complex and I think there's something about their complexity that really excites me as opposed to, I don't know, like I, I could be more excited about the complexity of the economy or something, but like somehow we are both really excited about the complexity of people.

Speaker A: Yes. You mentioned change. This is also something we've talked about and you've written a lot about. There's an excerpt of something I think from a while ago that I thought was interesting, which is you say, I was telling my therapist that all the writers I like are one, super self-aware, and two, unable to change themselves despite being self-aware. I want to be able to write about interesting things, but I also want to be able to change myself. Is that impossible? There's obviously personal stuff in there. Maybe more broadly, do you— do people really change, or is that just an illusion?

Are people kind of who they are? Speaker B: I definitely think people change. Yeah. Speaker A: What is that? Have you always believed that, or is there Have there been things in your life and relationships in the last decade that have evolved that view? Speaker B: I think the story I always tell people is that my parents have changed a lot. And so like, I really have, you know, your parents affect you so much. And just seeing my parents change really made me believe that people can, because I got like, you know, the very front seat view of it where, you know, when I was younger, my parents were very classic sort of like, you know, Asian immigrant parents, like, uh, very discipline-oriented.

Like, I had a curfew of like 6 PM until I was in college. Like, you know, I played piano, um, you know, I did math competitions, all these things. And my parents really were sort of bought into that style of parenting. And as I've gotten older, they've just like mellowed out so much. And like, not only has their parenting style changed, but like their entire sort of like demeanor, personalities. Like, I think they've actually gone a lot more into mindfulness, like themselves, you know. Um, you know, my mom and I talk about this, and like, even my dad has become so much more accepting.

And I think just seeing that in my family just makes me really believe that on like the order of decades, like, everyone can change. Speaker A: How do you, how do you reconcile that? So I think I agree. On the other hand, I kind of also believe that like, at least in certain ways, we very much are who we are. And, and in some ways, like, life is about sort of like finally getting to the bottom of either accepting yourself for who you are, seeing yourself for who you are. Kevin Kelly has this idea I love, which is like you're trying to become yourself by the time you get on your deathbed.

And yet also we totally can change. We totally can grow. It's almost like there's this tension of certain, certain things that are unchangeable that you have to just sort of accept. But also, obviously, people can grow, especially over the course of decades. Speaker B: Yeah, I definitely am very sympathetic to the idea of like we are all just becoming ourselves more fully. Like, I think that's a really beautiful idea, and I really like the idea of like, you know, we're just ultimately vessels, right? And so it's kind of like our purpose moves through us, not the other way around.

But I think I'm just really wary about being too prescriptive about who you are because I, I think that like saying like, this is how I am and I can't be any other way, like sometimes that's liberating, but other times it can be very defeatist, like you say. And so in general, in myself and in people I love, like, I just try to encourage like some level of, okay, well, like, you're saying, you know, that's just the way I am. Like, is that actually true? Like, does that feel like the shape of your soul, or does that feel like something that's convenient to say?

Yeah, yeah. Speaker A: Is that an internalized story? Yeah, totally. And that feels like maybe where the line is, where being able to see yourself clearly in that way is actually like the root of self-awareness and being able to really know. But so often we layer other narratives on ourselves or failure or success or whatever. And you're like, oh, I don't know. Speaking of James Clear, one of the sort of super simple identity things that he talks about that I love is just like, don't say you're trying to, I don't know, be on time.

Like say you are someone who isn't late. And like, that's a very different, and oftentimes we have these narratives running in our head that aren't even like totally conscious. And I think breaking through that to your point is like an amazing kind of way to actually have material change. Speaker A: Is that an internalized story? Yeah, totally. And that feels like maybe where the line is, where being able to see yourself clearly in that way is actually like the root of self-awareness and being able to really know. But so often we layer other narratives on ourselves or failure or success or whatever.

And you're like, oh, I don't know. Speaking of James Clear, one of the sort of super simple identity things that he talks about that I love is just like, don't say you're trying to, I don't know, be on time. Like say you are someone who isn't late. And like, that's a very different, and oftentimes we have these narratives running in our head that aren't even like totally conscious. And I think breaking through that to your point is like an amazing kind of way to actually have material change. Speaker B: Yeah, I have very complicated feelings about like identity and how beliefs around identity affect who you are and your behavior.

But I definitely think that, you know, one thing I try to tell myself is like, be willing to like be surprised by yourself, you know. And just because I have never been a morning person doesn't mean like I can't be a morning person. Like, I mean, that sounds ridiculous, but I really try to actually be very open-minded about things like that, right? Where it's like, you know, something that's like been really interesting to me, or even over the past couple years, is like I used to think of myself as not a group person.

Like, I always thought of myself as someone who's only comfortable in one-on-one settings. And I think through the Substack and through just things changing, my own friend group, I've like become a lot more comfortable with like group settings and even been able to really enjoy myself in them. And like, I could definitely see a version of me where I really just had been like, I'm never gonna try this because this is not me, you know? I think that's the kind of prescriptivism that can be bad, where you close off things that could bring joy because you just decide that's not for you.

Speaker A: Yep. Yeah, drawing boundaries around yourself. Are there any things that you— I think obviously some of this is innate and you have like an implicit ability to see people Are there ways that either you've told other people or even learned yourselves— yourself, excuse me— to better see people, be more attuned to kind of them and what makes them tick, like model their theory of mind, like better be more empathetic? Any of these things? Are there ways that you think you've gotten better at that? Speaker B: I mean, to our point earlier, like just asking people a lot of questions.

Like, I, uh, it's sort of like a joke or a meme because I have a lot of friends who just love to ask questions. I think we all make fun of each other, right? Where it's like, oh my God, like, don't do that thing you do. But at the same time, like, in general, I'm like a huge proponent of like, yeah, like, if you want to know something about someone, like, have you tried asking them? And like, I actually give this advice a lot. Like, sometimes someone will just be like, oh, like, I wish I knew like what my girlfriend thought about this.

And I'd be like, Have you tried being like, hey, it's like, hey Emily, what do you think about this? And often they're like, no, like, I couldn't do that. And, um, I think that, yeah, your life can change so fast if you're just like, I'm gonna go around like asking people about what they actually think or feel about this thing and like just let them answer me on their own terms. Speaker A: Yeah, we make a lot of assumptions. You are enamored by relationships. You have now started to actually work on hopefully getting more people into relationships, both I think broadly with your writing, but certainly also very tangibly with matchmaking.

Do you think that helping people get into romantic relationships is something that is close to or a core kind of like mission of your life. I mean, that's a very broad statement. It seems to me over time you've been gravitating more and more towards that. If in 10 years, like, that is the revolving theory of your work and life and creativity, would that be surprising? Speaker A: Yeah, we make a lot of assumptions. You are enamored by relationships. You have now started to actually work on hopefully getting more people into relationships, both I think broadly with your writing, but certainly also very tangibly with matchmaking.

Do you think that helping people get into romantic relationships is something that is close to or a core kind of like mission of your life. I mean, that's a very broad statement. It seems to me over time you've been gravitating more and more towards that. If in 10 years, like, that is the revolving theory of your work and life and creativity, would that be surprising? Speaker B: No, I definitely feel comfortable saying that, like, helping people I love be in fulfilling relationships, romantic and platonic, is like a core thing I want to do with my life.

You know, like, as you're saying this, I'm like, yeah, why is it that, you know, like, I was telling someone my goal in 5 years is to get all of my currently unmarried friends married. Watch out, Jackson. Uh, and I was like, I was just thinking as you were talking, like, why, why do I want to help them find friends? And it's because, like, most of my friends already have these exceptional friend groups, right? And so I don't really worry about that. Like, the romantic relationships are kind of like what is left.

Repeat. I think we are in an era where people are finding it quite hard to date. I think they're also finding it quite hard to make close friends. But I have a really wonderful friend group and I've been in really wonderful romantic relationships myself. And I think I just like really believe in the power of relationships to make your life better in every way. And it's like really meaningful for me to try to help to— yeah, try to help people find those. Speaker A: Speaking of friendship, I think friendship is one of the more underrated things broadly and definitely underwritten about, talked about, created about in, in writing and art and media.

Fortunately not by you. I think you talk about it a lot and you write about it a lot. Maybe I'll kick us off with something you wrote, which is the idealist in me would like to say that being ambitious about platonic love is how you start to be ambitious about everything else. Including romantic love. The cynic in me points to— out there are 1,001 articles telling people that they should have better friendships and very few telling them how. Obviously you mentioned most of your friends having really rich friendships, but I am curious maybe broadly if you have any thoughts on— and we'll get into The Friendship Theory of Everything and some of these other things, but broadly how you think about friendship, the impact it's had on your life.

And if you were going to give kind of like one high-level take on maybe the ways that people can improve either the quality of their friendships, the amount of them, or even their approach or disposition to friendship? Speaker B: Yeah, I mean, I think friendship is the entry point to everything meaningful in life. I just gave a talk about this recently, so I'm very prepared. So stop me from going on. But basically, I think that, you know, we come into life with basically like social and sort of familial constructs on what good life is.

And so like, as someone who Chinese-Canadian, child of immigrants, grew up in Vancouver, British Columbia. Like, I feel like I was told, you know, like a very kind of prestige-motivated kind of like view of what makes life good. So like, go to like an Ivy League college, like get this, like, you know, get a job in finance or become a doctor, like just do something that's like very professionally valued and stable. And, you know, like that's how you have a good life if you like achieve all these things. And I think, you know, some of that dovetailed with what actually gave me joy, but also a lot of it like didn't, right?

Like I'm fundamentally this very like autonomous, like creative person who like maybe didn't want to climb the career ladder, right? And I think it's through finding a peer group that's also quite unorthodox and like untraditional that I was able to really like find my own meaning, right? Where like by seeing people who I really respected and looked up to follow their own paths, I was able to be like, oh, like some of the things they're doing are things that could also make me happy, right? I think this applies for everyone where if you have a peer group that you really love and also admire, looking at how they live their life and the choices they make can help you make just better choices for yourself.

And so I think that's sort of what, you know, the number one reason I would give to like why you should invest in your friendships. It's just because like they can really not only make you happy through the relationships themselves, but like they can model to you how you should be living your life in a way that's meaningful. I think that, yeah, friendship is like hugely under-theorized in our society as compared to romantic relationships because we sort of expect romantic relationships to sort of like bear many of the things that friendship traditionally did, right?

Where like we want our partner to kind of be not only like a lover but also you know, someone who's a great conversationalist, someone who shares our intellectual interests, like someone who like, you know, does all the same hobbies, and also someone who's like great at like doing domestic tasks and childbearing with us. And like, it's just everything, right? And I think in reality, if you have a strong friend group with people who like satisfy a lot of those needs and give you— it can actually help you be more appreciative of your partner because you're not trying to make your partner everything, right?

And so Yeah, I think in friendship you sort of have the ability to like choose people who you really love hanging out with who don't have to be everything to you, and that actually allows you to really go deep on specific like aspects of like your passions or your interests or just things you share, um, that maybe like you couldn't actually explore with a partner. Speaker A: Yeah, it's like a constellation or mosaic versus the singular. And I think unfortunately so much of this obviously stems from this sort of just pragmatic nature of you.

Great. You have tons of friends. You have two 20s, 30s, early 30-somethings talking about friendship. It's so easy, blah, blah, blah. You and I don't have kids, whatever. Over time, life gets hard. You move away. And I think one of the things that I really admire about how you've talked about it is, granted, you're not in that next phase necessarily, but you've just talked about the reasons to actually make it a higher priority than maybe the average person does. One of the kind of the most succinct, and this gets into the, you're the average of the people you spend the most time with, but you say, you accept that in choosing who you spend time with, you choose who you are.

And I think when you relate to friends in that way, or maybe even with a level of intention or deliberation, as you were mentioning around, I want to be more like X, I want to be more like this person, you, the main way to do that, the best way to do that, I think you and I would agree, is to spend time with someone who is like that. In that sense, are there— and, and I, I would strongly recommend, you've written a lot about friendship. Your, your piece, The Friendship Theory of Everything, is one of my very favorites, both on San Francisco and on, and on friendship.

Um, so I'll link that. But are there any things in particular that you personally really value in friendships? Speaker B: I think just attentiveness is really important. I really think that, to your question earlier about like, do I have any like advice or tips on friendship, like, I think it's just you have to really invest in friendship. And I think a lot of people aren't you should be investing in friendships the way that you invest in romantic relationships. Um, I think I've been really lucky to like find a friend group where like we all like give each other a ton of like attention and energy and time and effort, you know.

And I think that's sort of like what can make it work, right? Where like the truth is like a friendship will fall apart if like one person is just like checked out, right? Like you, you can't hang out with someone who doesn't want to hang out with you, right? And like Obviously people get busy, people get busy, people go through life things, people will be unavailable for periods of time. But I think for any like long-term successful friendship, like it has succeeded because both people attended to each other like for many, many years.

And I think like I've been really lucky to find people who I hope I can do that with. I think I have friends now who, you know, I've been very close to for a decade. I'm hoping I can say in 2 more decades, like, here are the friends who I've been close to for 30 years. Yeah, I think it really is just about finding the people who care as much as you do, right? Where like, I think people are a little bit too negative in the sense of like, they love to talk about like the rule of why things don't work, right?

Like, oh, like book clubs, they don't work. Like, you know, you don't have friends after you become a parent. Like, you know, like all these things, like, you know, and it's true. Like a lot of people, like the default case might be that it just doesn't work. But the thing is like, people do crazy things all the time, right? Like You know, people literally start communes and keep them going for like decades. So it's like it's not this thing where like people absolutely can't make something like a rich friend group that like survives like parenthood or different phases of life work.

It's more just like there are a lot of like examples of why things fail. But I think it's also really important to study like the successful cases, right? And I think for me, like I'm always trying to learn from like the people who I think are doing it really well. And I can't say that I'll succeed, but I want to emulate them. Speaker B: I think just attentiveness is really important. I really think that, to your question earlier about like, do I have any like advice or tips on friendship, like, I think it's just you have to really invest in friendship.

And I think a lot of people aren't you should be investing in friendships the way that you invest in romantic relationships. Um, I think I've been really lucky to like find a friend group where like we all like give each other a ton of like attention and energy and time and effort, you know. And I think that's sort of like what can make it work, right? Where like the truth is like a friendship will fall apart if like one person is just like checked out, right? Like you, you can't hang out with someone who doesn't want to hang out with you, right?

And like Obviously people get busy, people get busy, people go through life things, people will be unavailable for periods of time. But I think for any like long-term successful friendship, like it has succeeded because both people attended to each other like for many, many years. And I think like I've been really lucky to find people who I hope I can do that with. I think I have friends now who, you know, I've been very close to for a decade. I'm hoping I can say in 2 more decades, like, here are the friends who I've been close to for 30 years.

Yeah, I think it really is just about finding the people who care as much as you do, right? Where like, I think people are a little bit too negative in the sense of like, they love to talk about like the rule of why things don't work, right? Like, oh, like book clubs, they don't work. Like, you know, you don't have friends after you become a parent. Like, you know, like all these things, like, you know, and it's true. Like a lot of people, like the default case might be that it just doesn't work.

But the thing is like, people do crazy things all the time, right? Like You know, people literally start communes and keep them going for like decades. So it's like it's not this thing where like people absolutely can't make something like a rich friend group that like survives like parenthood or different phases of life work. It's more just like there are a lot of like examples of why things fail. But I think it's also really important to study like the successful cases, right? And I think for me, like I'm always trying to learn from like the people who I think are doing it really well.

And I can't say that I'll succeed, but I want to emulate them. Speaker A: And good things are hard. Speaker B: Yeah, good things are really hard. Speaker A: Yeah, I think that's a huge part of it is just it simply stops being a priority. And obviously you're not going to be able to have that with tons of people. But I think it's something that, yeah, I certainly aspire to. Speaker B: And it's not like a lot of people's vision. Like, that's the thing. Speaker A: Like, it's good. Speaker B: And I wouldn't say that has to be right.

Like, some people really are like what I need in my life is like my partner, like my romantic partner. And, uh, one of my friends and I were talking about how like, you know, like there are many people who fall in love and they're immediately like, okay, let's move to Montana and we never have to see anyone else again. And I'm not here to say that's not valid, right? Because like your vision of life is your vision of life. My point is like, you know, if you want— if you're someone who's like, I'm always going to really value a close friend group, but I want to like live close to all my friends.

Like, you can't be befriending people who are like, I want to hang out with my romantic partner, I moved to Montana, you know? So I think there is kind of— Speaker A: yeah, it's a great point. Speaker B: You gotta find people who have that shared vision and really invest in it because like, yeah, a lot of people are gonna want something different from you and like, that is okay and they're allowed to want that. Speaker A: Totally. And, and but also I think maybe I would, I would argue that a lot of people maybe just haven't seen that vision or maybe gotten to fully experience it in part because they haven't invested.

And that's the, that's the case for one other piece of friendship that I, I find so interesting is this sort of like lack of boundary or rules around it. Unlike almost all of the, at least family and romantic relationships, like a lot of our relationships or connections in life have very clear expectations and rule sets. And friendship is like the opposite. There's this Tim Kreider quote I love, which is, he says, the, the same thing that makes friendship so valuable is what makes it so tenuous. It's purely voluntary. You enter into it freely without in the imperatives of biology or the agenda of desire.

Officially you owe each other nothing. And so there's this like weird softness around it despite everything you just said and how important it is and how much people can influence us and all these types of things. There's the added layer of like the expectation setting and friendship in trying to train, change your friends is very different than with a romantic partner. How have you navigated that part, especially of maybe your closest or most intimate friendships? Acknowledging. Uh, the example I always give is like, if you were dating somebody for 4 months and you decided to move across the country and you just told them like, hey, I'm moving across the country, wanted to let you know.

Or same thing with your family, you'd be seen as a sociopath. But if you did that to your best friend of 10 years, it would be normal. And it like kind of explains the, which I think is one of the positive parts about friendship too, but there is this weird grayness to it. Speaker B: Yeah, I think we don't come into friendship usually with a default contract the way we come into romantic relationships. You know, in a romantic relationship, like, let's say, yeah, like, two people are going to become boyfriend-girlfriend, like, there's usually like a very socially normative kind of understanding what that means.

Like, let's say we're gonna see each other 3 to 4 times a week, uh, maybe we'll be sexually exclusive with each other. Yeah, like, you're gonna reply to my text messages, you're not gonna suddenly move across the country without telling me. And yeah, we don't really have those in friendship, which, you know, I think means that you have the freedom to individually come to or negotiate contracts with each of your friends. But I think it can also be like really scary and overwhelming for a lot of people, especially if like, you know, I think the idea of like negotiating what a relationship is, is really frightening to a lot of people for a good reason, right?

Because like that puts so much, like, it's too much agency almost, right? Speaker A: And so like, I think also in just in friendships, it's less normal, so it might feel like a higher— or it would be weird to not have that conversation in a romantic relationship. But if you went to one of your friends, you're like, hey, I want to define things, the default would be like, what? Speaker B: One thing I talk a lot about with some of my friends, like the idea of like friendship scripts, you know, um, kind of as a joke where like people need to know that they can do these things with their friends, right?

Like You're allowed to say to a friend, like, you gotta move to San Francisco. You're allowed to, like, do a 2-person trip with a friend to, like, Iceland. You're allowed to, like, you know, you're allowed to, like, go on a long road trip with a friend. Like, you're allowed to, like, yeah, you're allowed to do all these things with your friends. Like, you're— and most people, I think, don't know that you can, or maybe you feel scary or weird, you know. Like, I have some number of conversations about this because I guess like, yeah, I, I write about this for work and have done workshops around the topic of friendship.

It's like very interesting where I think a lot of what people want to know is like, am I allowed to say this to my friend? Speaker A: Yep. Speaker B: And I think a lot of relationships, uh, a lot of friendships in particular fail because people don't know how to answer that question. Like, can I say like, it really hurts my feelings that you like totally have neglected me after you've gotten this new job? Or can I say like, I don't like your fiancé? Like Can I say, hey, you've been a bad friend to me, like, for the past year?

Like, can I say these things? And I think my instinct is usually towards answering yes, right? I mean, and I think there certainly is a right and wrong way of having conversations, and like, it's important to be tactful. But like, only when you start kind of like opening up these questions and kind of being like, well, I'm here, where are you, that you can really kind of start to address like What do you want out of a friendship? Speaker A: It doesn't mean that we have to be in the same place, by the way.

No, I, I'm— we only have some— there's this old idea I like, which is like the intimacy maintenance matrix of like, you obviously, romantic partner, probably your family, whatever, high, high in the top right of the matrix. And you only have so much bandwidth for high maintenance along with intimacy. That said, like, talking about it is one of the ways that you can actually map each other and, and hopefully be a really good friend. And I think that's The other part of it, it's like a little— it's not taboo, but it's just there's something about friendship that makes it a little weird to be like, hey, here's what I want, or here's what I need, or whatever.

Speaker B: Yeah, I mean, we're all polyamorous with our friendships, and I think actually that creates a lot of freedom, I think, in a good way. Where, to your point, like, one thing that's funny about friendship is like, if you— if your goal is to get married and like be in a monogamous relationship, like, you— I mean, you can— some people do this, but it's like probably not advisable to kind of be like, I want to date this person, they don't want to date me, so I'm just gonna like sit around and wait for 5 years.

Like, probably shouldn't do that. But in a friendship, like, I, I have like met people before and literally thought like, we're gonna be friends. Like, we're not friends right now because they don't know. Like, you know, we don't live in the same place, we haven't really talked, like, I don't have the energy, whatever, but we're gonna be friends. And 3 years later That's like, okay, I got you, you know. And you can just do that with friendship. You can just kind of be like, like, you can just sort of be like, okay, well, the timing is not right now, but it'll be better later.

Or like, you know, with some of my friends, like, they're going through a really hard time and they just like, don't talk to me for 6 months. And like, because, you know, we're all in these polyamorous friendships, I don't have to be like, you're not meeting my needs right now, so like, bye-bye, you know. You can actually have the patience to be like, Oh gosh, like they're going through something really hard, but they're going to come back, right? And I think it— because we have this kind of unstructured freedom, it actually allows us to be like more generous and maybe more patient.

Um, but I think also it's like another thing that's I think possible and like okay to do is you can also like say to someone you're really close to, like, I don't want you to stop talking to me, right? And I think that's something that's considered very like maybe unacceptable in friendship, but I think sort of like underexplored where like I've actually had friends say to me like, "You're a bad texter. Can you get better?" You know, and I'm never going to be a great texter, but like, there is like, I actually welcome that, right?

And like, I think like there's been times when like people have said to me like, "Oh, well, I want you to be more consistently there for me." And like, you know, "It would make me feel loved if you did this for me." And like, I think these are very much like what we consider part of the romantic frame and like, "Oh, it's like weird to ask that of my friend." But I don't think it's weird. I think it's like, okay, if you're really close to someone to just be like, Hey, you're not meeting my need in this way.

Like, are you interested in, like, you know, us having a closer, more consistent relationship? And I think you'd be surprised sometimes at what, like, people are willing to give you if you're willing to ask. Speaker B: Yeah, I mean, we're all polyamorous with our friendships, and I think actually that creates a lot of freedom, I think, in a good way. Where, to your point, like, one thing that's funny about friendship is like, if you— if your goal is to get married and like be in a monogamous relationship, like, you— I mean, you can— some people do this, but it's like probably not advisable to kind of be like, I want to date this person, they don't want to date me, so I'm just gonna like sit around and wait for 5 years.

Like, probably shouldn't do that. But in a friendship, like, I, I have like met people before and literally thought like, we're gonna be friends. Like, we're not friends right now because they don't know. Like, you know, we don't live in the same place, we haven't really talked, like, I don't have the energy, whatever, but we're gonna be friends. And 3 years later That's like, okay, I got you, you know. And you can just do that with friendship. You can just kind of be like, like, you can just sort of be like, okay, well, the timing is not right now, but it'll be better later.

Or like, you know, with some of my friends, like, they're going through a really hard time and they just like, don't talk to me for 6 months. And like, because, you know, we're all in these polyamorous friendships, I don't have to be like, you're not meeting my needs right now, so like, bye-bye, you know. You can actually have the patience to be like, Oh gosh, like they're going through something really hard, but they're going to come back, right? And I think it— because we have this kind of unstructured freedom, it actually allows us to be like more generous and maybe more patient.

Um, but I think also it's like another thing that's I think possible and like okay to do is you can also like say to someone you're really close to, like, I don't want you to stop talking to me, right? And I think that's something that's considered very like maybe unacceptable in friendship, but I think sort of like underexplored where like I've actually had friends say to me like, "You're a bad texter. Can you get better?" You know, and I'm never going to be a great texter, but like, there is like, I actually welcome that, right?

And like, I think like there's been times when like people have said to me like, "Oh, well, I want you to be more consistently there for me." And like, you know, "It would make me feel loved if you did this for me." And like, I think these are very much like what we consider part of the romantic frame and like, "Oh, it's like weird to ask that of my friend." But I don't think it's weird. I think it's like, okay, if you're really close to someone to just be like, Hey, you're not meeting my need in this way.

Like, are you interested in, like, you know, us having a closer, more consistent relationship? And I think you'd be surprised sometimes at what, like, people are willing to give you if you're willing to ask. Speaker A: Totally. There's this old— I think maybe Tim Ferriss, Jerry Seinfeld did an interview years ago and he said if you were to compress the human struggle down into one word, it would be confront. And obviously we talk about confrontation and having hard conversations, again, more in a romantic relationship context. For example, I think friendship is one area where actually, at least in my life, I've, I've been fortunate to have friends who are willing to confront sometimes and tell me the things that I don't want to hear.

And I think maybe all of us, our friendships might be richer for having some bandwidth for that type of thing. One of the other, and it certainly ties right in, one of the other ideas that you talk about a lot and that I really find interesting is is your appreciation of consistency. And I think you've talked about both this in a sort of individual sense and in a group sense, most recently with your, your essay on frames. Maybe to start with the individual piece, um, there's, this is probably a year ago, you say accountability is the most important thing.

Someone who does what they'll say they do, who has self-respect, a relatively small delta between how you act and how you want to act. It's not that that's the only attractive quality, but I know it's the most necessary quality. Without it, everything else becomes redundant. I think you're someone who really values— maybe it's consistency, maybe it's almost like self-alignment. Can you talk a little bit more about that? Speaker B: Yeah, I definitely think that, you know, it's the Joan Didion self-respect thing, right? Where if you can't trust yourself, it's really hard to like, I think, be happy with your life, right?

And I think accountability is sort of the way I understand as the primary way of like trusting yourself, right? Where if you don't have accountability or consistency, it's kind of like you're this person who's like totally unpredictable to yourself, right? And you're kind of like, to me, like always living in this like almost state of fear, right? Where it's like, okay, who knows what's going to happen, you know, with me? Speaker B: Yeah, I definitely think that, you know, it's the Joan Didion self-respect thing, right? Where if you can't trust yourself, it's really hard to like, I think, be happy with your life, right?

And I think accountability is sort of the way I understand as the primary way of like trusting yourself, right? Where if you don't have accountability or consistency, it's kind of like you're this person who's like totally unpredictable to yourself, right? And you're kind of like, to me, like always living in this like almost state of fear, right? Where it's like, okay, who knows what's going to happen, you know, with me? Speaker A: Like, I'm unreliable this week or this month or this year, right? Speaker B: And I think there's like an incredible amount of safety in kind of knowing like, I decided I'm going to do this, so I'm going to do this.

Yeah, I think we talked about this earlier, but I do think, you know, like I described how like starting my Substack kind of like marked this entry into a period of my life where I was a lot more consistent. And I, I really feel like I can say, like, being consistent has changed my self-image and, like, my sense of safety with myself, right? Speaker A: Yeah, yeah. Speaker B: Um, and I, I find that a lot of people who— like, a lot of times when people come to me with some kind of personal dilemma about, like, okay, like, what should my job be?

Or, you know, I don't feel good about my life. It's, it's often— not always, but often— kind of like this question that's really about self-trust, right? How can I, you know, how can I know that I'll really succeed at this? Like, how can I know that this is the right, like, career path for me? How can I know that I can be like a good partner? And like, I think these are ostensibly about one thing, like, okay, like, will my company fail or succeed? But they're really about something else, which is like, can I trust myself to show up in the way that I want to?

And I think a lot of these questions are not actually about the result, but they're about the process. And the people don't even know they're about the process. Speaker A: Yeah, to your earlier point, sometimes the thing ahead of consistency or upstream of consistency is commitment. It's the actual sort of reducing down the decision space and saying, this is what I'm going to do. Yeah, that's, I think that's so poignant. The, the other piece of this obviously is, is consistency with others. You wrote a recent piece about frames, which you kind of defined as like a set of agreements between yourself and other people, the ways that we're going to show up in a relationship.

You talk specifically about male-female excuse me, male-female friendships is one instance of this. I'd love for you to expound on this idea in particular, just because I think it's like, I think it's useful for people to maybe even have more accountability with themselves. But I also just think it would probably like thinking this way might help all of us in our relationships and also maybe even help with some of the boundaries we were talking about earlier of like expectations. Speaker B: Yeah, I think my therapist would refer to this as contracts, but I prefer to think of it as frames where Basically, I think of a frame like between two people, which is maybe the easiest way to explain it, as like, you know, kind of an agreement about how you'll show up for each other, right?

And so like in the male-female friendship thing, like someone asked me a question about that, like, okay, well, if there's some amount of like attraction or if there's like the, you know, natural tension of like the gender difference, like how do you have a successful friendship? Like some people don't believe we can do that, right? And like to me the answer is like, you know, you actually have an agreement between two people about like how you'll act towards each other. And that, you know, encompasses kind of like the very mundane things like, okay, like, you know, when one person texts, the other person will like, you know, to schedule a meetup, the other person will be like, okay, yeah, I'm free Thursday.

And it's about— but it's also about things like, well, where are you hanging out? Like, what kind of hangouts do you do? Like, what do you text about? How often do you reply to each other? Like, you know, what is your affect towards each other when you're actually in person? We have this in each of the relationships in our lives, but I think when it comes to like a frame between two people, like the really important thing is that both people are sort of on the same page and committed to it, right?

So I think in a healthy friendship, both people are like, well, this is sort of the setup that we have, and it works for me and it works for you. And like, if there's any problems, like, we'll work on it together. Speaker A: Or maybe we'll even talk about it explicitly. Speaker B: Exactly. Speaker A: Going back to the earlier thing. Speaker B: Yeah. Or just, you know, maybe we won't talk about it, but we'll just adjust, right? And I think the failure point, which the person was sort of asking me about was like, well, I think it can't work, right?

If like you want to be friends with someone, they don't want to be friends with you. Right? Like it's like, okay, like we actually just want different things. And I think, yeah, I think everyone's probably been in a situation where like, okay, it sort of feels like I want the relationship between us to be this one thing and ostensibly you agree, but it really feels like you're actually not happy, you know? And I think it's just, I think it's like, you know, applies in like a variety of situations, not just male-female friendships.

But I think it's like for anyone, it's like I don't enjoy like hanging out with someone being like, are you not having a good time? Like, is this relationship not— yeah, like no one likes that feeling of kind of like the other person in the relationship is like having a really bad time because they're like frustrated in some way, you know? And so I think like, okay, one, do you have a good frame? And two, like, does it actually work for both of you guys? Is just like really important in any kind of relationship.

And you see this in romantic relationships as well, right? Where it's like, you know, the classic, well, it's hard for a relationship to work if one person's like, we should move in, other person's like, yeah, let's see each other twice a week, right? And that's very normal actually, right? And so there is kind of this question of, well, can they align on it, or is one person gonna be unhappy forever, or are they gonna break up? Speaker A: Yeah. And I, uh, again, maybe a theme here, I think that's a little more common for people to think about it that way in a romantic relationship in a friendship or even a work relationship, any of our rela— I think just applying this model more consistently, or at least reflecting on it, what is this sort of default set of assumptions and expectations I have with this interaction, this thing, I think would probably, one, help us be more successful, but two, hopefully make us more empathetic and like a little bit more attuned to the way the other person is coming to things versus just assuming the default view, everyone's going to see it exactly how I do.

Speaker A: Yeah. And I, uh, again, maybe a theme here, I think that's a little more common for people to think about it that way in a romantic relationship in a friendship or even a work relationship, any of our rela— I think just applying this model more consistently, or at least reflecting on it, what is this sort of default set of assumptions and expectations I have with this interaction, this thing, I think would probably, one, help us be more successful, but two, hopefully make us more empathetic and like a little bit more attuned to the way the other person is coming to things versus just assuming the default view, everyone's going to see it exactly how I do.

Speaker B: Yeah, I think thinking explicitly, especially in platonic relationships, of like, am I— like, is this frame working for me? Is really important, right? Because I definitely see a lot of people online saying things like, you know, I feel like I'm always the one who has to reach out, like, to my friends. Like, you know, they sort of neglect a relationship. And I, I think it's actually really valuable to be like, well, like, why, why is that the case, right? Like, you know, is it because, like, Yeah, like, what is going on there, right?

Like, have you sort of like set yourself up in the role where you'll always initiate? Are you kind of hanging out with people who like don't value you that much? Like, what is going on there? Like, I think there's clearly a frame difference, but like actually why is it happening and can you do anything about it is sort of the important thing to like look at. Speaker A: Totally. One of the things you talked about briefly in the frames piece was like when you notice certain people like have performant bits they do.

And this got me thinking about, I don't know, one of the topics I maybe am most conflicted on, which is authenticity. One of the, another really early thing I read of yours, you basically wrote at the time, this was a few years ago, that you didn't believe authenticity exists. I've made this case to people at different times. I'm not sure if I believe it. And it certainly has to do also with whether or not we can change. And maybe even authenticity isn't totally the right word. Maybe it's originality, maybe it's self-awareness or alignment with yourself.

But especially a few years later, I'm curious what your current relationship to authenticity is, especially as someone who's performing her life to some degree online. Obviously, again, there's, there's boundaries around that. Speaker A: Totally. One of the things you talked about briefly in the frames piece was like when you notice certain people like have performant bits they do. And this got me thinking about, I don't know, one of the topics I maybe am most conflicted on, which is authenticity. One of the, another really early thing I read of yours, you basically wrote at the time, this was a few years ago, that you didn't believe authenticity exists.

I've made this case to people at different times. I'm not sure if I believe it. And it certainly has to do also with whether or not we can change. And maybe even authenticity isn't totally the right word. Maybe it's originality, maybe it's self-awareness or alignment with yourself. But especially a few years later, I'm curious what your current relationship to authenticity is, especially as someone who's performing her life to some degree online. Obviously, again, there's, there's boundaries around that. Speaker B: Yeah, I think it depends a little bit on how we're defining or using the word authenticity.

Like, I think if authenticity means like honesty. I think honesty is something that like, if anything, in the past few years like I've come to like value more in the sense of like, well, is our honest— like, am I being honest in my relationship? Am I honest as in, you know, I'm sort of like accurately and considerately communicating what I really experience in a way that will be like understood and received by the other person? I think that is Like that idea of like being honest in my work and in relationships is something I think about a lot.

Authentic. Speaker A: Again, is that almost like a consistency of internal and external? Because get a part of maybe what you were getting at in, in that piece years ago, um, it was the one about Belle, the, the like anime movie I think that you watched. And then I've talked about a lot too is this notion that like, I think people don't even necessarily know what when they are being authentic. Like, it's this recursive thing where you, you don't totally realize the ways you're sometimes performing to other people, etc. And so maybe the honesty piece is less about what the really core thing is, if that's unknowable, and more about, am I presenting something externally that is fairly consistent with what I'm experiencing internally, or what I perceive myself to be experiencing internally?

Speaker B: Right. Um, I think maybe the way that I understand it is sort of like, you know, we all perform personas for other people, and I think that there's sort of this human instinct where no one likes to feel that the persona that they're being presented with deviates really far from the emotional experience of the actual person, right? And so like, I think it is very jarring, like, for some, you know, if I were to say to you like I, I love, like, you know, this Donna Tartt book. Like, you know, let's say you said The Secret History is your favorite book.

I'm like, oh my gosh, like, I love that book too. And then you heard secondhand from someone a couple days later, like, wait, Ava hates that book. It's just all what's going on about, you know. I, I think there would be kind of the sense of, like, well, Ava in that case, like, knowingly, like, lied to me about something in order to make me feel better, right? And, like, I think we would consider someone inauthentic if they were literally going around like doing that all the time. Speaker A: Sure, but that's, that's like a pretty— I think so much of this is actually more that like it's a, it's in like the much finer print, I guess.

Speaker B: Yes, and I think it's really hard because I don't think anyone is like, like anyone who's like socially normative is not like completely authentic in the way that we would be defining it, right? And so like I think there's sort of this like philosophical dilemma of like sort of like what is the acceptable line, right? I think that's probably— I, I don't remember exactly where I wrote about it, but I think like probably that's why I said like, you know, fetishizing authenticity. Like, I feel like in a way we're like post-authenticity, right?

Where it's like, because we're on social media, like the way that we kind of have to present ourselves, like both in social context but also like online, at work, there's a million different contexts. Like, it is by nature like we are so far from kind of the first-person experience of what we actually feel like necessarily. Like, you cannot honestly represent your inner experience across all these different mediums in like an authentic way. In that way, I think we're post-authenticity. But I think maybe what you're asking is more like, is the concept of it still useful in some way?

Speaker A: Yeah, yeah, yeah. Speaker B: And I think that it is. I mean, I think— okay, maybe what I'll, I'll offer my take, which is I think the feeling of authenticity is deeply linked to charisma. And I think it's hard. Speaker A: This is where it gets fuzzy. Yes. Speaker B: Yeah, yeah. And I think that, yeah, so I think sometimes when we're talking about authenticity, like, we're really talking about charisma, right? Speaker A: This is where it gets fuzzy. Yes. Speaker B: Yeah, yeah. And I think that, yeah, so I think sometimes when we're talking about authenticity, like, we're really talking about charisma, right?

Speaker A: Or even an aesthetic. Like, uh, the thing that happened with like the, I don't know, like indie bands and hipster people in the early 2010s was like you would literally have people describing someone as authentic, describing an aesthetic, not describing anything about that person. It was a completely performed thing. And on top of this, obviously, that you were getting at with the internet is just like, we all have a meta-awareness of everything all the time, which partly not to maybe get ahead of you, but partly why I think your definition around honesty is so useful, which is like, it's a slight tweak on maybe the same thing we're describing.

And again, acknowledging that on some level, yes, people who are whatever charismatic seem self-evident. And so we describe them as authentic, but like it's, It's a little muddled. Speaker B: Yeah, I think authenticity is so powerful because like it's something that we want to feel and we need to feel in order to be compelled. But yeah, I, I, as I think we both know, like most charismatic people are not particularly authentic whatsoever, you know. Um, I, I guess the interesting thing is like maybe I would say I think a lot of people who are charismatic are at least able to be like, they have a level of kind of honesty with themselves, which is what allows them to kind of like portray that feeling to other people.

Like, I think there's a sense of like, in order to be like really effective, I think there's a level of almost like self-honesty that people have, and that's sort of like visible in like how they talk and how they present themselves. Now, are they actually being honest with someone else, you know, or, or being authentic? Like, not necessarily, right? And that's, I think, where it all kind of like breaks down. Is it even possible for them to be like— like, is it possible as a politician to be honest, right? Like, I mean, like, I think it sort of like definitionally breaks down.

But I certainly think like maybe thinking about authenticity as kind of like a level of like self-honesty that can be perceived by other people is still like meaningful and interesting. Speaker A: Yeah, or at least an internal consistency. Speaker B: Yeah. Speaker A: This gets into, uh, in some ways like a topic of the moment and a lot of people have talked about and written about it, maybe especially adjacent to technology in the last year, but I think particularly relevant to you beyond the cliché, which is taste. And a word that you've used that I think is really, um, right and obviously ties to the authenticity piece is interiority.

One of the things you wrote recently was that one of your big learnings of the year was understanding the way someone's interior life translates to what they make. Which in some ways, I don't want to overreach here, but like, if you were going to try to describe authenticity, at least in a creative standpoint, I think it's, it certainly maps there. Using that maybe as a broad frame, there are 3 definitions that you've talked about or ideas you've talked about relating to taste. And I thought it would be fun to go through them.

The first is just like very simply consumption is the entry point and the notion that like by covering a lot of ground, You actually, like, that's kind of actually how you develop taste. One of the things you said is, if there's one thing I know, it's that taste takes a lot of consumption to create. It's the trap of the former lifestyle blogger or the former style blogger who is now all aboard minimalist anti-capitalist train. You bought so many things before you learned out, learned how to pick out the 20 perfect, perfect secondhand items for your fall wardrobe.

Like how Didion learned to describe fashion, the lifestyle of the wealthy from her time writing captions at Vogue. First, you acquire the vocabulary that gives you the legitimacy, then you critique it. And this notion that basically, actually, like, more than anything else, the people we describe as having amazing taste— I always give the example, like, maybe Rick Rubin, it's just easier for him to listen to the incremental amount of music compared to the normal person, versus this notion that, like, taste is this instinctive thing that you're born with and you just know what's good.

Speaker B: Yeah, I definitely think that for most people, it It sort of dovetails to what we were talking about earlier where it's like it takes a long time to kind of know yourself, right? And I think like having taste is really about like self-knowledge. And maybe some people are born just with self-knowledge, but I think that's very few of us, you know? And I think most people actually have to like work to know what's true to themselves. Yeah, do that through consumption. Speaker A: Yeah, then the next one that I think dovetails right there is, is maybe taste is just following your attention and having the energy at least to do that.

Specifically, what one idea you got at that I found really relevant is like, it's almost instinct versus narrative. And a lot of that, I think the reason taste gets convoluted, especially if we talk about good taste and bad taste, is like it's sort of this narrative running over what you think you feel about things. And versus just like having a very personal, actual, sometimes even like animal reaction to something versus like, oh, I should like this because I'm the type of person who likes this, or people, the people who I think are cool like this.

Maybe I'll read again. You say, I don't think that your taste needs to be original, but I know it needs to be personal. I love it when people choose objects that feel like them. I don't believe in paying other people to tell you what you like. I prefer it when people have opinions about shape and texture, about voices and movement. When someone tells me what specifically makes them feel good, I understand them for the first time for real. Speaker B: I've put way too many of my opinions on this. Speaker A: Oh my God, I'm just bombarding you today.

But I mean, talk about authenticity, which, which I don't, I should let you speak, but I do think there's something really beautiful in this notion that like, it isn't even necessarily being original. That's all, that could totally be like, I got, I stole this idea from somebody else, but it is personal. Speaker B: Yeah, I've been like going on and on about this like line about, I'm pronouncing it wrong, but Miuccia Prada, who, you know, is like the Prada designer, about like how basically there was a profile on her in which like the author's friend said, upon seeing a Prada show a few years ago, like, wow, that woman must have the most amazing interior life, you know?

And I think there's, to me, like, that sort of the thing that's interesting, like someone with a really interesting interior life. And sometimes you can look at someone, you can just be like, oh my gosh, you know, like, what a cool person. And you can somewhat just tell from like their glasses or like their coat or something like they are alive in that, you know. I think that's actually such a hard point to get to where like you can sort of express your internal life that well. I think all of us have obviously our own interior lives, but like most of us are not maybe so in touch with them, you know.

I think it's actually like a lot of work to really get in touch with like your own interiority. And like, you know, we There's certainly not, like, a lot of, like, guideposts in our culture about, like, how you would even go about doing that, you know? Speaker A: I really love "they are alive" in that. That feels like the perfect kind of encapsulation of what, when you see it in someone, it's not really explained, it's felt. Speaker B: Yeah, like, "What does that have to do with you?" is something, like, I often think about when I see something that, like, you know, to me feels like it's in bad case for me feels inauthentic, where it's like, like, what's the connection?

You know, it feels like something that you, that you're just trying on for size and not something that's like a, a heartfelt statement about you. Speaker A: Yes. Okay, the last one that I thought was quite interesting that I think is a lot older, so I'm curious if you're going to remember, but you said, when what you get is what you want, that is taste. It almost has to do again with the, like, self-accountability, maybe. Speaker B: Yes. I mean, I guess speaking to my own experience, like, I think I was critical.

Like, I knew what I didn't like way before I knew what I liked, right? So I, I don't think I was someone with, like, a, you know, preternatural sense of style, like, whatsoever. In fact, I had, like, a very bad sense of style for, like, most of my life, right? And it, it kind of, like, the way that that sort of manifested was just, like, things felt wrong to me, but I couldn't really figure out like how or why. And I think knowing myself better, for example, like now, like when I get dressed, like I feel the absence of that sense of like wrongness, you know?

And so I think a lot of the times like we're just kind of looking for that alignment, right? Like, I mean, I hear this all the time, like, okay, I have a wardrobe full of clothes and like nothing to wear. Like, that's just a way of people saying like everything feels wrong, right? And I think like— Speaker A: They're not feeling alive in this. Speaker B: Yeah, yeah, yeah. But it's like, you know, it's actually really hard to go from that to, I do feel alive in this particular thing. Speaker A: It takes a lot of consumption and a lot of following your attention, a lot of time.

And yeah, yeah. I think that's so right. Has writing or words specifically, as a lover of words, been one way you've been able to kind of attune yourself to what that is? To know it rather than the anti, to knowing this is wrong, to knowing this is right? Because obviously some of it is wordless or beyond words. Speaker B: Yeah, I mean, I guess one way that's helpful is that I think like I always like love reading, right? And so I think from like a pretty young age, like one way in which I was like focused on figuring out why life was like through books.

And so like, you know, I, I learned the first— one of the first things I learned was like, okay, what I like to read or why I particularly really like, you know, find beautiful in words. So like learning to do that in one format helps you do it in another, right? So like, I don't think I'm as intuitive of a verbal— sorry, as a visual thinker as I am a verbal thinker. But like, because I sort of knew I could figure out like sort of my— what my taste in words was, I sort of had this confidence I could do it for like visual mediums as well, right?

It's sort of the sense of like, if you can do it for one thing, you can do it for another, you know? Speaker A: Yeah. Yeah, yeah, yeah. You build more. It's like a little bit the confidence of the memory of success again. It's like you start to have more confidence in your process and your knowing and how attuned you are and how well you know yourself, whatever. Speaker A: Yeah. Yeah, yeah, yeah. You build more. It's like a little bit the confidence of the memory of success again. It's like you start to have more confidence in your process and your knowing and how attuned you are and how well you know yourself, whatever.

Speaker B: Yeah. I mean, I have this one friend who is just really good at learning and it's like really annoying, right? Because he'll like try something and he'll just like very quickly become extremely good at it. And like, I mean, one way of understanding that is maybe like he's just like unusually talented. But I think another way of understanding it is like he's just like found a very consistently successful way to learn, right? And so like, you know, and that applies to like making food, and it applies like physical acts like rock climbing, it applies to like, you know, work things like— he, he just has found a way of like learning and paying attention that translates to every kind of medium.

And like, you know, I'm certainly not there, I don't think most of us are there, but like, yeah, it's a good thing that you can figure out how to do. Speaker A: That's cool. Okay. I have a handful of kind of like grab bag miscellaneous questions for you. Speaker B: All right. Speaker A: One is you sort of sit between two worlds. I don't know if you relate to it that way, but you obviously worked in tech earlier. You live in San Francisco. You have a lot of friends who are in tech.

You are in your own kind of world of writing and Substack, and you write about feelings and emotions and romance and all these things. And yet you're obviously like pretty attuned to the ambition tech AI kind of thing happening. Do you experience— and a year ago or so roughly, you actually stopped writing only and you went and took a tech job for a little while. Do you experience FOMO? Are you like at times, are you seeing all this AI stuff happening? Are you totally at peace with that? Do you feel like you're sitting between the two worlds or just these are all my interests and it's fine and I happen to live in a city where tech's big?

Speaker B: I mean, I am like, I really love technology. Speaker A: Yeah. Speaker B: And I do like consume a lot of like, I like reading about technology. I'm very interested in technology. I think that's like not the area I work in right now. Like it could be something I work on in the future. But for me, I guess the way I relate to it is like, okay, maybe one way of thinking about it is kind of like, I think two things I'm very interested in. One, I'm very interested in like relationships.

And two, I'm very interested in technology. And I currently like write and work more around relationships rather than tech. And that's kind of like where my interests fall right now and kind of what makes sense for my life. And like, I don't know if that will— that could stay the case. It could change. Like, I don't really have any resolutions around it, but to me it's more just like, you know, for a long time in my life, like relationships was a passion, but I didn't work doing it. Yeah, yeah, yeah.

So it's like for me, I think it's easier for me to think of it as like You're allowed to just have things that you care about and are interested in. And like maybe the professional aspect is something that like I'm a little bit less prescriptive about. Speaker A: Yeah. The funny thing is you're kind of— you actually have very similar interests, probably a lot of people you spend time with. You just have the work part flipped, which is funny. Okay. And then related, you love San Francisco. Speaker B: I do love San Francisco.

Speaker A: I promise I'm almost out of excerpts, but I have one more to read or a few more to read. One of them about San Francisco that I think maybe especially describes what I have a sense of that you clearly know very well, which is maybe something unique about the people who live here. Um, and the, in the good weird, um, you say, when I first moved to San Francisco at 19, and I think this is from The Friendship Theory of Everything, when I first moved to San Francisco at 19, I thought it was for the technology industry, but I've since realized that I'm in fact just interested in the type of people who tend to be fascinated with technology.

Or at least some subset of them. My friends are all pretty anti-authoritarian, willful, dogged, and cheerful. As B said, the type of people who believe they can fix the world's problems through sheer force of will. I think my favorite thing about them is that they're all very creative in the literal sense that many of them write and make art, make art, but also in the sense that they're very good at solving problems in unorthodox ways. San Francisco is many things, and I think people from the outside looking in are sometimes critical of technologists.

There's different ways to put it, but this is one of my favorite ways. I think like the really wonderful optimistic vibe of people who live here. What do you love about San Francisco? What do you love about the people here? Speaker A: I promise I'm almost out of excerpts, but I have one more to read or a few more to read. One of them about San Francisco that I think maybe especially describes what I have a sense of that you clearly know very well, which is maybe something unique about the people who live here.

Um, and the, in the good weird, um, you say, when I first moved to San Francisco at 19, and I think this is from The Friendship Theory of Everything, when I first moved to San Francisco at 19, I thought it was for the technology industry, but I've since realized that I'm in fact just interested in the type of people who tend to be fascinated with technology. Or at least some subset of them. My friends are all pretty anti-authoritarian, willful, dogged, and cheerful. As B said, the type of people who believe they can fix the world's problems through sheer force of will.

I think my favorite thing about them is that they're all very creative in the literal sense that many of them write and make art, make art, but also in the sense that they're very good at solving problems in unorthodox ways. San Francisco is many things, and I think people from the outside looking in are sometimes critical of technologists. There's different ways to put it, but this is one of my favorite ways. I think like the really wonderful optimistic vibe of people who live here. What do you love about San Francisco?

What do you love about the people here? Speaker B: I mean, the excerpt has summed it up pretty well, but I think Yeah, I really love my friends, and I think my friends are people who are very thoughtful, kind, yeah, like anti-authoritarian, self-motivated, and like deeply care about their loved ones as well as the world around them. Like, I think they're just very alive to like not just like living in the world, but kind of like what they can do and like how they can contribute. And I just like really Yeah, I really love that kind of as like a personality type or as an orientation towards the world.

And, you know, I'm sure people like that exist in like all sorts of industries, but like, I feel very lucky to have found like, to me, like one pocket of the world where there's like such extreme concentration of that type of people. Speaker B: I mean, the excerpt has summed it up pretty well, but I think Yeah, I really love my friends, and I think my friends are people who are very thoughtful, kind, yeah, like anti-authoritarian, self-motivated, and like deeply care about their loved ones as well as the world around them.

Like, I think they're just very alive to like not just like living in the world, but kind of like what they can do and like how they can contribute. And I just like really Yeah, I really love that kind of as like a personality type or as an orientation towards the world. And, you know, I'm sure people like that exist in like all sorts of industries, but like, I feel very lucky to have found like, to me, like one pocket of the world where there's like such extreme concentration of that type of people.

Speaker A: Yeah. High agency too. Speaker B: Really high agency. Yeah. I think it's hard because, you know, like maybe at one point tech was the underdog, but certainly isn't, right? Like tech is like you know, where much of like basically the power of the world is like concentrated now. And like, I think because of that, like, I think fairly in many ways like tech is really maligned, right? Because it's kind of like this really like powerful, scary force. And like, you know, we don't necessarily have a lot of sympathy for the people who like— Speaker A: by the way, we think we're smarter than you at everything, we're taking over the government.

Speaker B: Yeah, it was— I, I'm not saying that as in like we should feel sorry for people who work in tech and like, you know, like they're also misunderstood at all. But I'm saying that like I think partially because of how successful the tech industry has become, I think like it is really easy to just like caricature all the people who work in tech as like, oh, this one type of guy who sucks, right? And like, at least, you know, because I just happened to move here at a particular age and like fell in with a bunch of people who like work in tech in a bunch of different ways, like I can like say firsthand, like, you know, obviously like my friends are not all this one type of guy who sucks, you know?

And that, that's something I feel very comfortable like attesting to beyond anything else. Speaker A: by the way, we think we're smarter than you at everything, we're taking over the government. Speaker B: Yeah, it was— I, I'm not saying that as in like we should feel sorry for people who work in tech and like, you know, like they're also misunderstood at all. But I'm saying that like I think partially because of how successful the tech industry has become, I think like it is really easy to just like caricature all the people who work in tech as like, oh, this one type of guy who sucks, right?

And like, at least, you know, because I just happened to move here at a particular age and like fell in with a bunch of people who like work in tech in a bunch of different ways, like I can like say firsthand, like, you know, obviously like my friends are not all this one type of guy who sucks, you know? And that, that's something I feel very comfortable like attesting to beyond anything else. Speaker A: I think that's— maybe it's changed, but that's kind of the sense of the novel too, is like a little bit of a novel set in this time in San Francisco.

And I'm— yeah, I think we, we all look forward to that. One writing question: you occasionally use the second person, and I like— Speaker B: I— Speaker A: both of your writing and just, I don't know, there's that chapter in Tomorrow and Tomorrow and Tomorrow in different pockets, like What I guess I'm curious, like, when— what goes into choosing to write in the second person? And is there a reason you think it's so powerful? Speaker B: I have no idea. I mean, I think choices like that— first person, third person— um, I, I have been trying to play around a lot more, especially in fiction, and sometimes in like my own writing too.

Uh, like, I'm sorry, like for the sub staff, it is definitely something where I know there's all like all this theory around it and I've like read some of that. But I think for my own, just like for my own creativity, when I get to like, why am I making this choice? It kind of like frees me up, you know? So it's definitely something where like I try to have some— Yeah, yeah. Like I recently made this change in one project where I switched from writing from first person to like third person.

And like there were, there are these like ostensible reasons for the change. Like for example, I wanted a little bit more distance from the narrator. But I also like had this like awareness of like, oh my gosh, like don't get too— this is the reason why I'm making the change, you know? Because I feel like when I, when I get too like technical about it, at least for me, I find that like it sort of interferes with like the part of my subconscious that kind of like is creative. I was talking to a friend recently that actually this is a big thing for me about learning how to write plot, right?

Where it's like I, I used to be someone who like really over— wanted to overthink it a lot. Like, you know, this has to happen because of this. And like, then I realized that there are all these writers who actually just write like plots on kind of like a sentence-by-sentence like basis, right? Where they're kind of just like writing and they let things happen like chapter by chapter as they unfold. I sort of realized like, oh, like I think my brain is a little bit more like that where like I sort of need to just like let my subconscious do a lot of it.

And if I let my conscious mind do it, I kind of like trip myself up. Speaker A: All right, well, that doesn't help the rest of us, but we'll have to trust the process. Who do you read that most consistently challenges you or like introduces new ideas or learnings or beliefs? Speaker B: Um, I don't know if there's one author I could choose. I mean, should we say living or dead? Speaker A: Yeah, I, I was almost thinking like a little more like modern Substack type thing, but maybe that's the wrong way to go about it.

Speaker B: I really like, um, Elif Batuman's, uh, Substack. She wrote The Idiot, which is this very successful novel, um, and I really like her Substack. I also really like Mary Gaitskill's Substack. She also wrote one of my favorite collection— story collections of all time, Bad Behavior. I feel like I'm cheating because these are not like sort of like native internet writers, um, but like they're just writers I really like. Speaker A: Different question: who is— what's the one thing pre-1950 that you would recommend people read? Speaker B: I really love Anna Karenina.

Uh, I think it's like a must-read for everyone, basically. Yeah, I, I feel pretty comfortable saying you should not die without reading some Tolstoy. Speaker A: Well, you've only recommended it to me like 6 times, so I've got some homework. Speaker B: Um, I don't even remember that, but I'm always going on about it. Speaker A: It's— I think you have good company in that recommendation. We talked a little bit about energy earlier, but Do you have a clear answer for what you think you're motivated by? Speaker B: Um, I think maybe that thing we were talking about earlier about like being myself as a vessel and just sort of wanting to be like a good expression of whatever like life force I'm lucky enough to possess.

Um, I think especially post-psychedelics, I've become a lot more comfortable with the idea of like, for me, and again, like I'm a very much more like subconscious-driven person than like Like, I think I am someone who, like, I don't necessarily need to go know where I'm going as long as I know that I'm kind of proceeding in, like, a way that I'm proud of. Speaker A: It's— I think you have good company in that recommendation. We talked a little bit about energy earlier, but Do you have a clear answer for what you think you're motivated by?

Speaker B: Um, I think maybe that thing we were talking about earlier about like being myself as a vessel and just sort of wanting to be like a good expression of whatever like life force I'm lucky enough to possess. Um, I think especially post-psychedelics, I've become a lot more comfortable with the idea of like, for me, and again, like I'm a very much more like subconscious-driven person than like Like, I think I am someone who, like, I don't necessarily need to go know where I'm going as long as I know that I'm kind of proceeding in, like, a way that I'm proud of.

Speaker A: And it congruent. Yeah. Yeah. Well, speaking of that, what do you think 10 years ago you would be most surprised about your life now or who you are now? Speaker B: Hmm. Okay. I think that Maybe 10 years ago I would, I would have been like, actually like made many of the predictions, many predictions for my life that line up with how I'm currently living. Like I want, I always wanted to be a writer, like from when I was a little girl. Speaker A: Like sometimes we know these things.

Speaker B: Yeah, I always wanted to have this like amazing friend group, but I definitely had this fantasy about living in New York. So maybe you should be like, you moved to New York and then you moved back to San Francisco. Like what is it about the West Coast? Speaker A: You got it pretty right. Speaker B: I think that's a good moral for this podcast. Speaker A: We will get you back to New York, maybe. I don't know. I don't like those chances. Speaker B: Yeah, the West Coast. Like, that's the thing about San Francisco.

Like, it really has uncanny grip on you, which is why maybe one day, Jackson, you'll be back. Speaker A: You got it pretty right. Speaker B: I think that's a good moral for this podcast. Speaker A: We will get you back to New York, maybe. I don't know. I don't like those chances. Speaker B: Yeah, the West Coast. Like, that's the thing about San Francisco. Like, it really has uncanny grip on you, which is why maybe one day, Jackson, you'll be back. Speaker A: What do you most want to hold on to in 10 years from now?

Speaker B: I hope that I'll still be writing. I think that that's like really important to me. Like, I really hope that I'll be writing for the rest of my life and Yeah, also like a lot of the things we talked about today around like having really strong group, friend group. I have been really thinking in the past month especially that I like, a lot of my friends live within like 10 minutes walking distance from me now and I've been really appreciating it, especially just in the holiday season. Like it feels so meaningful to me and like you said, we can't know the future, but like it'd be really meaningful to me if I can say in 10 years like, okay, I still have hopefully the same people that I really love, and they're not like— they're all in California still, or a lot of them are, and they're not like all having moved to like Ohio or like— Speaker A: yeah, I relate.

And I suspect all the youngish parents listening, especially while we were talking about friendship, as long as you are all laughing at us, but that's what you have to aspire to. Okay, just a few more things. One is you've written about uselessness Mm-hmm. As this sort of way to describe the things that don't seem obviously relevant or efficient or effective or important or purposeful. You say artists are inherently vulnerable because they pay attention to things other people don't. The things that you are explicitly told you shouldn't because they're impractical and lead to little or no material gain.

How do you feel about uselessness these days? Speaker B: Well, I think sometimes, like, I feel like, okay, my Substack can be, like, accurately described as— I don't know if I'd say useless, but it's like I write about, like, emotions and relationships. I don't write about them in, like, an academic context or anything, you know, sort of like, you know, maybe it's, like, seen as acceptable to, like, get a PhD on like psychiatric stuff or like to work as a therapist, right? But like, I just like writing about emotions and relationships.

I just do that like for fun because I want to, right? And I don't think that's like a job path anyone like prescribes to their kid, nor was it a job that I knew even existed, but it just happens to be something that I want to do, right? And so I think like my work literally exists because I'm kind of like, well, I want to do this thing, and seems implausible to me that I could like be ever something that supports me, nor could it be like useful to anyone in any way, but like I'm just go ahead and do it because that's what's fun for me.

And so I think, um, I can really advocate for like doing things that just like don't have clear tangible like value because yeah, I, I think some of the things that are truest to you are probably going to be things that you find it very difficult to translate in in a way that's like, I can easily get a job doing this, right? And like, that's why they're worth doing, in fact, like, because you can't do that translation. And like, a lot of times why they'll be interesting to other people is because of that kind of like incoherence, right?

We're like, I just want to do this thing, and I don't necessarily think it's going to work, and I don't know if it's going to be interesting to other people, but I just really want to do it. Like, I think that's one of the most important sentiments ever, like, that can exist in you. And I find it really sad because I think a lot of people stifle that in themselves, right? Where I know so many people who are extremely gifted who sort of like, they sublimate like what they actually want to do into something else, right?

It's like, okay, like I love like reading, so I'm going to become like a lawyer. It's okay to become a lawyer, but it's like, you know, I think there's a lot of people who don't like what they do who do it because it's the only acceptable route that's sort of close to what they actually want to do. Speaker A: Not willing to take themselves on face value. It's almost like they're not willing to take themselves at face value, right? Speaker B: And like, you know, I like, everyone has to make money.

Not everyone's privileged enough to kind of like, you know, go off like and like try to make something that doesn't make money their full-time job. But I think there is this level of like even letting yourself do it for you. Yeah, feels really important. And like we discussed this, like I don't think I would encourage— I certainly would not encourage everyone to go off and try to become like an artist because I think a lot of people might like really hate that lifestyle actually. But I think I feel very comfortable encouraging everyone to do like the creative thing as a means to them.

Speaker A: To do art in a way. Speaker B: Yeah, yeah, yeah. Speaker A: One piece of this, at least to me, is about beauty. I think maybe at least in the world that you and I, or the worlds that you and I inhabit, there's all kinds of people trying to do great things, ambitious things, important things, effective, useful things. And there have been people who pursue beauty, but maybe that's a little less common. I thought this was particularly beautiful. You say, I don't believe that anyone is dead to beauty.

And then you quote Martin Shaw: Beauty kickstarts our attention. The real sublime, to behold it is almost scary because we suddenly have a longing to stand for something. Beauty not as generic but specific, troubling in what it may call forth in us. Then you again: Beauty literally demands replication, as Elaine Scarry points out. Scarry: We wish to procreate with those we find beautiful, continue their genetic lineage. Beauty inspires the desire to confess. Speaker B: Yeah, I'm a big fan of beauty. Speaker A: I think to more of that, my last— I'm going to read one more quote of yours, and you don't have to even say anything else if you don't want to, but there's an interview with Ezra Koenig being interviewed by Rick Rubin.

I listened to last year and he's playing a song called This Life that I really love. And he's just lying. And Rick says that what it captured for him, you get a, you got a chill up his spine, is this beautiful composition that you see in so many wonderful, beautiful things, which is heavy and light together. And I think that's one of my favorite things about your writing is the fact that you simultaneously write about things that are deeply, deeply important, maybe the most important, and yet you can also do it in this way that you could read on a Tuesday morning on the train or whatever it might be.

So I'll quote you now. I read a book on resolving addiction through mindfulness. When you feel like you want something, need it, you're supposed to breathe in and ask, Is this image me? Is this feeling me? Is any of this me? Then you're supposed to realize none of it is you. Okay, so if I'm not the things I want, the things I love, then who am I? If I'm pure presence, then how am I supposed to live? Lightly, apparently. But I don't want to live lightly. I want to live heavily.

That is why I write. Speaker B: That's very nice. Ending quote, Jackson. Thanks. Speaker B: That's very nice. Ending quote, Jackson. Thanks. Speaker A: This is really fun. Thank you for doing it. Speaker B: Thank you.