Description

Charles Broskoski (Website, Are.na, X), aka Cab, is an artist turned entrepreneur and co-founder & CEO of Are.na, a platform for collecting, connecting, and self-directed learning. I created an are.na channel for all of the references I used in preparation for this episode. https://www.are.na/jackson-dahl/dialectic-cab.

Charles began as an artist before becoming a software engineer, and started Are.na with many collaborators out of a desire to replace the now defunct del.icio.us after it was acquired by Yahoo. He and a range of collaborators have been working on Are.na for nearly 15 years, and he is now focused on it full-time, thanks to the platform’s 18,000 paying subscribers. While I’m not a longtime Are.na user, I discovered Charles by way of his talk / essay, “Here for the Wrong Reasons” and was enthused by his philosophy of attention and how the things we encounter shape us.

Our conversation centers on patterns of noticing and what it means to know yourself through what you pay attention to, or as Charles calls it, your radar. We discuss creativity as decision-making, self-directed learning and research, and Are.na's channels as frames for what we encounter. We also talk about personal versus performative taste, opinionated design that still gives you space, building something that lasts, and why Charles believes creative people should start deeply personal businesses.

I hope you are inspired to be generous and scrutinizing with your attention, to create things that are personal and durable, and to remember that knowing yourself is a worthy journey of a lifetime.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and where you can find all links and transcripts. You can learn more at notion.com/dialectic.

Special thanks to Earshot in NYC for hosting us for this conversation.

Timestamps

(0:00) - Opening Highlights
(1:21) - Intro: Charles Broskoski
(4:00) - Thanks to Notion
(5:26) - Start: Creativity as Self-Knowledge and Problem-Solving
(13:37) - Self-directed Learning and Casual Research
(21:33) - Skateboarding, Being a Beginner, In Defense of Posers
(33:26) - Contextual Patterns and Channels
(45:54) - Nodal Points, Your Radar, and Careful Attention
(1:04:57) - Subjectivity, Self-Knowledge, and Taste
(1:15:09) - Performance: Here for Fame and Not Love
(1:22:53) - Aspirational Attention
(1:29:02) - Designing Generous Tools
(1:42:44) - Space in a Product and Fading into the Background
(1:50:01) - Why Creatives Should Be Entrepreneurial & Building an Independent Business Online
(1:54:11) - Patience, Durability, and Antifragility
(1:59:48) - Personal Businesses
(2:10:27) - Grab Bag: Authenticity, Bohm Dialogue, Skateboarding, and Keeping Things Personal
(2:28:28) - Thanks Again to Notion

Links & References

Key Charles Essays:

Transcript

(0:00) Opening Highlights

(1:21) Intro: Charles Broskoski

(4:00) Thanks to Notion

(5:26) Start: Creativity as Self-Knowledge and Problem-Solving

Jackson (5:26): Charles Broskoski, thanks for coming.

Charles (5:28): Thanks for having me.

Jackson (5:30): Did I get that right? Broskoski?

Charles (5:32): Broskoski, yeah.

Jackson (5:33): AKA Cab. It seems like you’re Cab to almost everyone.

Charles (5:37): Cab is a nickname I’ve had my whole life, but it doesn’t make sense to say Cab Broskoski because “Cab” are my initials. It’s like saying “PIN number.”

Jackson (5:48): Well, we say “ATM machine.” We do it all the time. I want to start with a couple of quotes that are technically about writing, but I think they apply to much of what you are interested in. The first is from Arena, by you in the Philosophy channel. It’s Lara Palmquist via Nico Chilla. She says, “One of the writer’s essential duties is to gather, to filter and weave fragments, to refract perspectives and form new points of contact. The reader, in turn, acts the Widsith’s listening audience, learning from the sojourner’s song about how to speak of the textures of life. Such is the ongoing collaborative nature of a language we are not born knowing. We cannot express ourselves without first encountering the words of others. As is often remarked, effective writing serves not as explanation, but imitation. A bowerbird’s nest of noticings calling other minds to take roost.”

Charles (6:50): Oof, that’s dense.

Jackson (6:53): The second one is a little more straightforward. There’s a writer I love, Benjamin Labatut, who wrote a book called When We Cease to Understand the World. In an interview about his creativity, he says: “I don’t worry much about the shapes of the stories. It is all about research. I try to find things. To me, finding some other person’s phrase is more important than coming up with it myself. It is the part that I enjoy. In that sense, writing has become more akin to walking and picking stuff up off the ground.” And one final quote from you in an interview with Sophia Epstein: “It’s nice to look around.” With that context around collecting, my first question is: What does it mean to be creative?

Charles (7:41): You’re really starting straight in the deep end. The quotes you read and the concept of being creative are related, but slightly different. Those quotes are about understanding one’s own perspective. You have to understand where your gaze is naturally drawn. Being creative is about making an idiosyncratic combination of the perspectives you are drawing from. Creativity is a loaded word now, and it means different things to different people. To me, it’s about problem-solving. The connection I draw between those two concepts is that being creative is about problem-solving, while understanding your own perspective is about finding a way to put the puzzle pieces together. You look at something from one direction and then from another. What is the crossover? How do you draw something out from those two?

Jackson (9:36): What’s the space in between? I wanted to ask about creativity. We’re going to talk a lot about several things you just implied. Creativity is an interesting word—as you alluded to, it means everything and nothing. I want to talk about the curiosity, learning, and research side of your world, as well as what you refer to as nodal points: what we actually give our attention to. But I want to linger on creativity for a second. Two definitions came up in my research, and I’m curious about your thoughts. The first is from an Arena Influences channel via Christina Badal: “Creativity is just connecting things. When you ask creative people how they did something, they feel a little guilty because they didn’t really do it. They just saw something. It seemed obvious to them after a while.” Then, in an interview you did with Yatu, you said both he and Norm seem to understand that creativity has more to do with decision making. I think it takes a lot of artists a long time to understand that.

Charles (10:54): The “connecting things” quote is from Steve Jobs, which is funny. We lean on that a lot. The thing he’s describing—feeling guilty about pointing to something specific—is interesting.

Jackson (11:08): I’m surprised I didn’t recognize it.

Charles (11:11): It is a longer quote, but I always feel guilty pointing to him because it’s such a thing. The Yatu comment about decision making points to the same place. This is part of my quest to get more people who consider themselves creatives to start businesses. I really stand behind the idea that it’s just about decision making. Especially in the past hundred years, being an artist is like Duchamp: it’s about making decisions. That is all it is. You can do infinite things; you have to decide what you’re going to do. What is the rubric for deciding? The way Yatu and Norm approach their practice, and how it blurs the line between art and business, is a perfect example. They are just making decisions. They focus on a topic they feel the desire to explore, and then use their own perspective to chip away at that topic. Decision making there is a personal thing.

Jackson (12:48): There is an aspect where decision making is the engine. Maybe there is something else that is the wheel in the metaphor, but agency is inside of that. The most creative and prolific people are the ones where the engine is just going.

Charles (13:20): I think the hardest thing about that is knowing yourself. You have to get to that place first before you can make decisions that are correct.

Jackson (13:33): I want to come back to that.

(13:37) Self-directed Learning and Casual Research

Jackson (13:37): Before we do, I think it’s worth talking about what stands out to me across all these refractions of what Arena is. You say the point of how you describe Arena is not to box it in, but it continually comes back to this theme of self-directed education, learning, or curiosity. You describe it as Montessori or the reading room at the public library. I went to the New York Reading Room yesterday—you inspired me, and it was really lovely. Karly describes it as research as leisure activity. Damon calls it a toolkit for assembling new worlds from the scraps of the old. But again, it’s coming back to this learning thing, specifically a self-directed form of it. Have you always had a desire to be a lifelong learner?

Charles (14:37): I don’t know if I would have put it in those terms prior to Arena, but I was always the type to read a different book in class or go to the library to check out my own books. That has always been an impulse.

Jackson (14:57): Was some part of it almost rebellion, at least in that example?

Charles (15:04): Maybe. I have distinct memories of being in class, looking at a textbook, and having to be in a certain chapter but flipping ahead to a different chapter I knew would not be covered just to see what was over there. It’s part rebellion, but part just being interested.

Jackson (15:28): To the extent that has been a common theme, do you have a sense of what feeds that energy in you and what causes it to atrophy?

Charles (15:42): It really does go in waves. What feeds it is just making space for it. Honestly, I find it harder as time goes on because having a job related to using a screen means anything you might be interested in has to compete with every single other thing in the world. You have to set up the conditions for yourself, which means it’s to get up in the morning and not look at your phone right away—all those standard things.

Jackson (16:44): It is especially needed with the internet. Every writer does it; Seinfeld has a room in his house where he locks himself away with his legal pad.

Charles (16:54): There is that kind of thing, but there is also connecting to the interest. It’s funny specifically to be working on Arena because I developed a habit a long time ago of following any person on Arena who is remotely active. My feed is nonstop, and the quality is still really, really good. That’s an interesting part of it: it’s my job to look at Arena and make sure it’s functioning properly, but there are interesting things pulling at my attention when I go on there. I feel like I have to carve out time to just use Arena myself in a nice way, like I would if I wasn’t working on it.

C (17:55): Yeah.

Jackson (17:57): It says something that if you imagine any other content platform on the internet, getting the entire stream would kill you.

Charles (18:08): It is shockingly not overwhelming on Arena, but I do wonder what it would be like if I could roll it back a little bit.

Jackson (18:19): What is your relationship to the word research, or to the act of research?

Charles (18:24): I was thinking about this this morning because I was reflecting on a show I watched called Neighbors, which just came out on HBO.

Jackson (18:36): I heard about this. The premiere was recent.

Charles (18:38): It must have just come out. One of the neighbors is a 4chan, QAnon type person. The word research gets used in that context a lot: “If you just do the research, you’ll find…” It is this yarn-on-a-corkboard kind of research. When we started, we had to qualify the word research in a completely different way: it’s not academic. Now we have to qualify it as pleasurable. It’s casual.

Jackson (19:21): It’s a loaded word.

Charles (19:23): It is a loaded word. I think the way people do research now started with note-taking apps like Roam and now ChatGPT. Doing research means something different to a person, especially when thinking about it on the internet. I try to use following links on a Wikipedia trail as a way to lean into the self-directedness of what we mean by research.

Jackson (20:02): Do you feel like you are researching when you are using Arena in your daily life? I don’t know what else to call it.

Charles (20:12): Research is the closest thing, but it is a little bit more like self-directed exploration.

Jackson (20:20): Do you spend much time distinguishing between passive learning and active learning?

Charles (20:28): No, I don’t think so. It ends up being the same. It feels the same to me, to be honest.

Jackson (20:45): That was my sense, and I don’t think that would be a conventional view. Part of the connotation might be that passive learning is more likely to be things you are doing for fun anyway, or even “research,” while active learning is “I have to learn this thing.” I am probably too rooted in the traditional school metaphor.

Charles (21:13): I see what you mean. To me, those sound like different modes one might be in, but they don’t sound like the end result or the motivation is all that different.

Jackson (21:27): That might be something we come back to.

(21:35) Skateboarding, Being a Beginner, In Defense of Posers

Jackson (21:35): In the Yatu interview, he mentioned he danced in high school, and you compared skateboarding and dance as things you have to teach yourself. Most youth education is not self-directed. What about these types of activities builds that self-directed muscle?

Charles (22:10): It is embarrassing to admit, but I am 43 and I still go skateboard. The thing I like about it compared to other forms of physical activity is that you are deciding at any given point what you are going to do. It is really based on mood. The mood is influenced by so many different things. This is dangerous territory because I could talk about skateboarding for two hours, but one’s own taste in skateboarding is informed by consuming hours of skate media. You almost consume more reference for skateboarding than you do the activity—at least that is how it was when I grew up. Skateboarding and dance are both very referential physical activities. Every trick has a connotation. When you are doing something, it is a certain type of skateboarding.

Jackson (23:38): Do you think playing guitar has this set of attributes?

Charles (23:45): Probably.

Jackson (23:47): What I am hearing is the classic idea that you try to sound like so-and-so, and then you end up sounding like yourself. There is a modeling aspect.

Charles (23:59): You kind of fake it until you make it.

Jackson (24:05): That relates to being a beginner, which comes up a lot. In an interview with Daisy and Francis at Tasteland, you said, “I’m kind of a poser apologist.” If you notice that you are into something, you have to start somewhere. You have to act like you know more than you do. There is some part of presenting yourself as how you want to be that is not bad. It is just pushing yourself a little bit outwards.

Charles (24:33): Thanks for bringing up my poser philosophy. I love talking about this.

Jackson (24:39): Are posers earnest? Can they be earnest?

Charles (24:44): First of all, I don’t know if “poser” means anything nowadays. I reflect upon being young, learning how to skateboard at the skatepark, and the meme of your good memories versus your cringe memories. The cringe memories are etched in marble—terrible, embarrassing moments of asking an older skater how to do something. I don’t think that would happen nowadays.

Jackson (25:22): Why wouldn’t that happen nowadays?

Charles (25:29): I don’t think “poser” is a thing anymore. There used to be a sentiment that one has to pay their dues in any particular activity. I think people are much more patient and empathetic towards learning and being a beginner.

Jackson (25:49): I was going to say trying hard is way cooler now.

Charles (25:54): Trying hard is way cooler now.

Jackson (25:56): Even selling out.

Charles (25:58): I think that’s true. When I was younger, the people I looked up to were Gen X. Trying hard was very much not cool. Everything had to be done casually.

Jackson (26:16): To the extent you’re right that it is easier to be open about being a beginner, perhaps the realm where we’re more performative is the Internet. It still has this dynamic where it’s cool to try hard or sell out. You do a sponsored post and you’re in your buddy’s comments saying, “So sick.” I think about a place I spent a lot of time: Twitter. The dominant artifice of Twitter over the last five to seven years is the dunk. It’s kind of like saying, “Screw you, poser.” I do think that on the platform you’ve built, there’s something where you’re trying to say it’s okay.

Charles (27:21): They are very different modes. Arena is considered social only because some activity can be public, but I don’t think it’s social in the sense of Twitter, where the point is to talk to other people. On Arena, you are interacting with content, and you might interact with a person through content. On Twitter, you’re just interacting with people.

Jackson (28:01): A few thoughts come to mind. One is that you have described social networks that are about doing an activity as being more virtuous—that’s the implication, anyway. You may have even been thinking about old GitHub. I’m interested in that, and also this notion that Arena could be a totally private tool. I’ve used a lot of tools that are much more private. Maybe I’m wrong and there’s a whole back catalog of things that aren’t visible to me, but you have a lot of public Arena channels. Why do that all in public? Is it a default thing?

Charles (28:49): It has to do with different modes for me. Different people have different approaches to this. For some of my beloved channels, doing them in public adds a little bit of extra pressure that makes me more careful with them. The public on Arena is so slight that it almost means nothing. No one is really paying attention to what I’m doing.

Jackson (29:24): I’m not sure that’s true. You could say it’s sort of like if you were publishing on a website but not under your real name. But you’re the CEO of this platform. In theory, if anyone is going to be looking at anything on Arena, they’re going to be looking at your stuff.

Charles (29:45): But I don’t think people are analyzing “takes” in the way that they do on Twitter. The interpersonal dynamics that come up on Twitter don’t happen here.

Jackson (30:03): Do you have many private channels?

Charles (30:05): Yes, I probably have an equal number of private channels.

Jackson (30:07): This is what I’m interested in. To go back to the original theme, one of the stated uses of Arena is self-directed education and research. If that is the goal, perhaps it is almost an external pressure. If I know I’m writing something for an audience of one or five versus a journal, it changes the work. Maybe it’s like that.

Charles (30:38): That’s part of it. But the real rationale to make something public on Arena is that if you add things to your channels publicly, other people will add those things to their channels. You ambiently get exposed to other things that may or may not have to do with what you’re looking at.

Jackson (31:03): You get serendipity as a pipe in.

Charles (31:06): Exactly. That’s the utility of having it be social at all. To relate it back to the comparison to GitHub, when I first started publishing open source code, it felt scary. But then you realize that the feeling of platforms where it’s public—but having it be public is not the point—has a different quality. The publicness is a utility to you and to other people. It’s a really nice dynamic once you get a handle on it.

Jackson (32:01): It had me wondering whether this might be more… We’ve assumed we have social networks, but Instagram and Twitter aren’t social networks; they are content platforms. Arena is somewhere in between. I was thinking of a platform I like called Letterboxd for movies, or maybe Strava. There is something about the fact that it’s a single-player thing that can then become social.

Charles (32:37): I think that’s why people point to Letterboxd, Strava, or any platform where there is a primary thing to do and the social part is secondary. It always ends up being better. And it’s also easier to make a business around those things.

Jackson (32:58): It’s telling that all of those are subscription businesses.

Charles (33:04): Also, I still see people point to Pinterest as being one of the last places on the Internet. Even though it’s a shopping platform, it still feels like that to a lot of people.

Jackson (33:22): I wonder if that’s ripe for more new things.

(33:26) Contextual Patterns and Channels

Jackson (33:26): One other core part of this blurs between the attention and nodal point stuff. We were talking before we started recording, and an essential part of the medium of Arena is the channel. I think one articulation of that would be the “pattern.” There’s a quote from Christopher Alexander. He says, “At the core of these books is the idea that people should design for themselves their own houses, streets, and communities. This idea comes simply from the observation that most of the wonderful places of the world were not made by architects, but by the people.” He’s talking about The Timeless Way of Building and A Pattern Language. I thought it was an interesting way to start this conversation, particularly under the theme of self-directed learning. There’s something about organizing ideas in this way. If you want to take it in a high-concept form, you could call it a pattern. If you want to go low-concept, you call it a meme. What is it about these contextual buckets that is helpful in learning and maybe eventually in making?

Charles (34:44): I can only speak to my own experience and my own way of using Arena. The channels I have at the forefront I use as a way to filter things I’m seeing. It’s a perspective through which to view a certain piece of information: does it belong here or does it not belong here? When you open up the bounds a little bit and say, “Yes, this does belong here, come on in,” all of a sudden the bounds are shaped a little differently. You just have a way of looking at a piece of information or an idea that feels more personal.

Jackson (35:36): There’s a memory part. There are a lot of things happening inside of that thing you described. It’s a little bit just like, “I know where this goes.” Thus, maybe it will be easier for me to filter it and remember it. To your point, you can imagine a channel that you’ve just created that has three things in it. If you add a fourth thing, it…

Charles (35:56): …changes everything.

Jackson (36:00): Are you typically creating channels or patterns? You read or come across one thing—how do they form?

Charles (36:13): Usually, I’ve been noticing an idea forming, and it has to do with a couple of things. Typically, the way it starts for me is in private. It will be a couple of things to start—it needs to be between three and five. Once you have that, you have enough of a frame to judge other things against. I have maybe 10 of these types of channels over the years, and now I think the bar for me is so high of what that frame could look like. It’s not complex, but it’s more nuanced and some combination of being nuanced and new. I haven’t made a new successful one in a while.

Jackson (37:15): My sense is what you just described is actually a phenomenon that happens as creative people become more experienced. The benefit is they have more of these—whether or not they use any of this language or conception—it’s easier for them to slot things in. But the weakness might be something along the lines of what you just described, which is that they’re more rigid in what their set of patterns are.

Charles (37:50): The bar raises. It doesn’t necessarily raise in terms of grandiosity, but it’s something more subtle than that. The last couple of ones I’ve had that have been successful just end up turning into essays. The collection of things happen first, or I notice that I’m saying the same ideas to people over and over. That means I’m thinking about something, and then there are other things in the world that remind me of that thing. The life cycle in recent times has been that the frames come up, and then it shortly turns into an essay.

Jackson (38:44): This would be one of the strongest cases for this type of thinking. Maybe it goes back to the Christopher Alexander quote. I suspect that makes it way easier to actually write the essay.

Charles (38:55): Definitely.

Jackson (38:56): It’s like I have an organizing frame. Otherwise, you’re just gathering scraps and haven’t done the work to connect all the dots.

Charles (39:06): Definitely for me. Writing and collecting references are two very different things. I find collecting references to be infinitely pleasurable and writing to be excruciating.

Jackson (39:21): Maybe that’s a form of passive and active learning.

Charles (39:30): You can’t just have these things be pleasantly opaque and pointing to something mysterious.

Jackson (39:41): There’s a line I love: “Writing is high resolution thought.” Another one comes from Paul Graham, the Y Combinator guy. He says writing turns your ideas from vague to bad. Obviously, writing isn’t the only form, but there’s something very fun and generative about one. It’s almost compression. It’s like taking all those…

Charles (40:09): It’s the decision making thing.

Jackson (40:13): One other quote that maybe relates: You said the things that do well in Arena tend to be prismatic. They do well with a lot of different perspectives, and you can put your own perspective into it. Maybe this relates more to the social side. Have you ever had an experience where you’ve really seriously adopted somebody else’s pattern or channel into how you think or create?

Charles (40:38): Definitely. There are patterns that come up on Arena, not necessarily in terms of what kind of conceptual frame to draw around a set of references, but just patterns of using it in an open-ended way. Someone started this inbox pattern of making an open channel, calling it an inbox, or saying, “This is a guest book, come sign my guest book.”

Jackson (41:06): Almost like a UI kind of thing.

Charles (41:10): Someone else started this thing of prepending your channel titles with a symbol so that they’re grouped together in your index. I definitely adopt from other people.

Jackson (41:20): Are there ways that you found seeing the world in these types of buckets can be limiting?

Charles (41:29): That’s a good question. I’m embarrassed to say no, I do not think that they can be limiting. For me, it feels very productive to have a set of constraints, and I find the constraints that Arena has to be extremely productive. Myself and other people who I work with Arena on all use it the same way. It’s really hard at this point to imagine a different mode of working that is not like using Arena.

Jackson (42:13): You’ve grown and evolved around this certain type of scaffolding.

Charles (42:19): Exactly. I’m deep in.

Jackson (42:26): For better or for worse.

Charles (42:27): For better.

Jackson (42:27): There probably are some limitations, but also it’s been really empowering. You’ve been augmented by this way of doing things. One last little bit on this. The implication if you’re gathering all these things is that you might eventually look through them in different ways. People have described—I think Damon Zucconi said it’s effectively just building a personal archive. Or maybe this was you archiving the casual web. Two other quotes I really liked, one from the “Describe Arena at a party” channel: “Everything not saved will be lost.” Which comes from the Nintendo quit screen message.

Charles (43:07): Yes.

Jackson (43:09): That is so good. I found another Wikipedia term, tsundoku, which describes acquiring reading materials but letting them pile up in one’s home without reading them. That last bit has the implication I wanted to pull at: how often do you really dumpster dive the archives? This goes back to writing versus just picking up shiny objects. It is really fun to pick up shiny objects all the time. Going back through the archives doesn’t necessarily mean turning it into an essay, but it is a different mode. I am curious how you relate to that.

Charles (43:54): I have channels that I treat in a more special way than others. I go back through those all the time, almost like they are a gallery.

Jackson (44:08): They are slightly more solidified or crystallized.

Charles (44:14): There is something about the frame that I find continually attractive. At this point, having gone back and looked at them so much, it feels like all of that stuff is mine.

Jackson (44:28): You know it well. You have almost traced those grooves.

Charles (44:34): I am responsible for the things there. It is not someone else; it is all me.

Jackson (44:38): They have been in your house long enough that they are yours.

Charles (44:41): Exactly. On the other hand, our new app has a widget, and I am hooking up some of my very gigantic channels to that. These are channels where I might throw a link in to read later. Sometimes I get to them, and sometimes I don’t. But having them continually come up is a nice way of resurfacing that stuff without being too didactic. Part of our job maintaining and building Are.na is figuring out thoughtful ways to do that.

Jackson (45:26): As someone who used tools like Delicious, there is a temptation. I like dopamine from new information, so I am doing the tsundoku thing, but there are diminishing returns.

Charles (45:45): I have a real problem buying books. I have way too many.

(45:54) Nodal Points, Your Radar, and Careful Attention

Jackson (45:54): Let’s talk about nodal points. There are so many different ways to take this, but a good place to start is a tweet from Ted Nelson: “THERE IS TOO MUCH TO SAY AND IT GOES IN ALL DIRECTIONS. THIS IS NOT JUST A SLOGAN, BUT MY MOST FUNDAMENTAL BELIEF.” You also wrote an excellent piece called “Here for the Wrong Reasons” in which you describe nodal points: “When you encounter a piece of life-changing information, no matter how large the change part is, you are simultaneously discovering and creating yourself, becoming incrementally more complete. Your perspective is made up of a meandering line through these points. Learning, or maybe some precursor to learning, is a lot about developing the intuition to recognize when something you find in the world is going to be a nodal point for you.” What is life-changing information? What are you getting at when you say that?

Charles (47:11): It is different for everyone. Can you point to an early piece of life-changing information?

Jackson (47:18): There is an important part of the piece that sets the tone, where you describe Borges, hell.com, and skateboarding. Elsewhere, you describe it as something that causes an inflection. At least with regard to art, it is easy to think about the things that helped me develop that intuition.

Charles (47:47): As I said in the piece, my weakness is nostalgia. My whole family is afflicted with this. I think about early books and wonder whether the book formed the inclination or if the inclination was there and I recognized it in the book. The life-changing part is about that recognition. It is about understanding that this thing is made for me, or I am made for this thing, or we share a strong connection. The hardest thing about being creative is understanding yourself. The change is about understanding your own perspective. Whether the perspective is made when you encounter the thing or if it was already there is a quantum question.

Jackson (49:16): They are artifacts where you realize there really are things out there that feel like they were made for you.

Charles (49:28): Yes.

Jackson (49:29): You describe this as a never-ending path towards completeness or cohesiveness. things contribute as a piece of a very large puzzle, at least considered in retrospect. Do you aspire to completeness or towards some kind of fullness?

Charles (50:01): I think this is never-ending, ideally.

Jackson (50:05): Is the picture dialing in resolution?

Charles (50:10): It is dialing in resolution. That is a good metaphor. I don’t think there is a perfect state.

Jackson (50:20): There is a Kevin Kelly line I like: “The goal of life is to become yourself by the time you’re on your deathbed.” It is asymptotically approaching a limit. Another key idea you use in the piece is radar. You pull from desire lines, but the critical point is that it is a verb, not a noun, in terms of how we relate to these objects of our attention. They are more active than static references. You describe desire lines, the classic image of the walkway and an additional path made through the grass that shows where people actually wanted to go. You describe a desire line as a path made by walking. There is an active orientation here. Why is that active recognition—the agency inside of it—so critical?

Charles (51:28): I think it is so critical because it feels increasingly rare. It is really hard to feel a connection to one’s own radar because there are so many things that diminish that ability.

Jackson (51:47): To define it, since I am pulling from these ideas: a radar is the reason you care about a “nodal point.”

Charles (52:02): Sure.

Jackson (52:02): A nodal point being one of these things that changes inflection.

Charles (52:05): Right. It is the recognition of the thing—that the thing belongs to me or that we have some kind of relationship. That recognition is what I am calling radar. It is basically attention.

Jackson (52:21): But again, an active attention.

Charles (52:23): It is an active attention.

Jackson (52:24): I consume many things for which there is no radar happening.

Charles (52:27): Yes, one hundred percent. I think the radar’s ability becomes dulled over time with a lot of exposure to information. That is one part of it, but the other part is literally gigantic corporations with business models designed to hijack the radar without being too “social networky” about it. That is what it is.

Jackson (53:03): It creates a diffuse attention rather than a highly active attention.

Charles (53:11): As I was describing earlier, getting into the ritualistic mode of wanting to explore ideas or let your intuition guide you requires the stage to be pretty clear. For me, it means one should not have a lot of things pulling at you.

Jackson (53:45): That is what you mean by diffuse.

Charles (53:46): Exactly. One part of it is having active attention or active radar, but you have to actively try to set the conditions for yourself.

Jackson (54:02): is about the magnitude of our attention. I am trying to distinguish this I could be incredibly engaged with something that I do not have this relationship to. Part of that is just the medium, like seeing a film versus scrolling my phone. My question is (54:22): how much of this is about reflecting on it? I suspect there were things you happened to come across with very little intentionality that completely blew you away.

Charles (54:39): Yes, but you have to be in the mode where it is possible to recognize it or be blown away by it. There are different types of being blown away. One can be blown away by the pure artistry of a film without having the personal connection I am trying to articulate. The personal connection requires a certain fleeting mode.

Jackson (55:23): Perhaps what you are implying is that regardless of the object, I need to be in a certain state.

Charles (55:33): You have to be ready for the thing.

Jackson (55:38): There is another piece of this which ties into identity. You explicitly talk about how your radar is you. Not the things you focus on, but the orientation, the internal rule set, your magnetism, and the natural intuition you have had your whole life. Forgive me if this is too esoteric, but maybe this is a distinction between “we are what we love” and “we literally are our love.” Does that make sense?

Charles (56:13): That is part of trying to figure this out. It is not the collection of things; it is the fact that you recognize the thing.

Jackson (56:26): My mind went to the image of a teenager who has attached their identity to the music they are into. They haven’t quite made this jump yet. When you ask who they are, they answer, “Well, I have all these songs.”

Charles (56:43): “I’m super into hardcore,” or whatever.

Jackson (56:48): it is so tempting, at least for young people, to map our identity not to the radar, but to the objects?

Charles (57:00): That is a really good question. I have no idea, but maybe it is because there is a preciousness about the objects. When you first see those things that feel very special, you think it must be the thing. You think, “It is not me; that thing is special.” It takes a long time to understand that. Teenagers might describe a band or a song with the cliché that “it is the best thing in the world” and “it will change your life,” but it is actually just a certain thing for a certain person at a certain time period. There are conditions at play.

Jackson (57:49): It relates to another thing you discuss in the piece, rooted in there might be rocks I haven’t turned over. What if there are nodal points that would totally change my life that I haven’t discovered? It is soulmate. You wrote (58:14): “What gives me anxiety is if there’s a nodal point out there that I will never come across. What if ‘the one’ is a piece of information that I will never get a chance to give my attention to?” Damon Zucconi reframes it by saying we actually have “thing-shaped holes” in us. This ties back to the teenager who hasn’t learned this yet. It creates an abundance: my love is abundant, and I can find things to give it to. It is actually not the things.

Charles (58:48): Yes. Damon is really regretful about how he articulated the “thing-shaped holes.” I am very sorry, Damon, that we are bringing this back up. It goes back to the thing of it’s a verb, not a noun. The thing that you’re pointing towards could be anything. No one can really tell you what that thing is. I tend to think about the way I use Arena or go through a used bookstore with a thrift store mentality. A person could go into a thrift store and buy anything, and put in the right context, that thing was the right thing to buy. Same thing on Arena. There’s no telling. Quality is not on a binary scale. It’s an all-encompassing way at which one can approach a thing. Not to over-reference Duchamp, but just taking a thing out of a situation and putting it into a different context, that can be done with anything. The shadiest JPEG that you see, you can take that and find something meaningful from it. If it’s coming from the right…

Jackson (1:00:30): If you’re open.

Charles (1:00:31): If you’re open to it.

Jackson (1:00:31): There’s an Anni Albers quote, “Materials Metaphor.” Students worry about choosing their way. I always tell them you can go anywhere from anywhere.

Charles (1:00:39): Yes, exactly. And that’s the kind of thing that gives me comfort and anxiety at the same time. It really foregrounds agency and one’s own perspective. It highlights that the most important thing is knowing yourself. It’s the only thing.

Jackson (1:01:05): One other piece of this had me thinking. You can be curious in a truly open-ended way without much discretion. You say, “I feel like I have to constantly remind myself of the things I’m actually interested in. Sometimes I wonder if there’s a problem with being too curious. That is when you feel like you’re interested in everything.” While we do want to cultivate a curiosity, we also think about encouraging more sustained deep thinking. Put another way, curiosity and adoration are not the same. Deep attention is not the same. I wonder about that. One view says if there really are infinite nodal points and it is about my disposition, I should just be looking at as many things as possible and waiting to see. Whereas I think what you’re implying here, and what feels more resonant to me—especially if it is about my disposition and not the thing—is that I should be looking more carefully at fewer things.

Charles (1:02:16): I think it’s something like that. But I don’t think there’s a one-sized solution. I don’t know if I believe that. As you’re talking, I’m thinking about the mode in which a person finds themselves going down a Wikipedia hole. It’s the purest reason to believe that hyperlinking was a good decision. It’s fulfilling that dream. Sometimes one can find a thing that’s important in that kind of activity. But I don’t always think that just going down a Wikipedia hole is much better than letting your feed take you. It’s a step towards the right direction, but it’s not always an indication that this is going to yield good results or life-changing information.

Jackson (1:03:28): It goes back to the passive versus active. TikTok is full passive learning. Doing extremely hard research in the stacks is active. Maybe the point is to oscillate there and catch yourself if you’re just doing the passive work. Maybe this brings up an interesting question: Should this always feel fun or easy?

Charles (1:03:54): I wouldn’t call it fun or easy, but it’s related to those things.

Jackson (1:04:03): Like it’s downhill?

Charles (1:04:04): I don’t think it necessarily needs to feel downhill. I think it needs to feel engaging, which is not the same thing as fun.

Jackson (1:04:15): I’m pulling this thread and I’m kind of locked in.

Charles (1:04:22): That’s a nice place to be. As I just said, I don’t think that’s an indication that the gold is there. But having that kind of practice is useful for getting towards what I’m talking about. Just being able to have a radar or an attention span that feels more tuned, for lack of a better word.

Jackson (1:04:54): Tuned feels like a good word.

(1:04:57) Subjectivity, Self-Knowledge, and Taste

Jackson (1:04:58): I want to briefly broach the topic of taste, which you already alluded to being messy. There is a quote: “People often think about making work as if the person on the other side will have no choice but to enjoy it if the work is good enough. But it’s nice to think about the practice of viewing or consuming as an art form in itself.” I think this is kind of getting at something we already talked about. But it is interesting because it feels like sometimes there is work that is “good enough.” On one hand, there is stuff I have engaged with where my act of viewing or consuming was an art form in and of itself, and it took a lot of work. Then there are other things, like I watched Casablanca for the first time recently, and there wasn’t much effort required. I’m not really sure what my question is.

Charles (1:05:56): It’s hard, especially in this particular time period in the past three days when we find ourselves in “Taste Wars 10” or whatever.

Jackson (1:06:12): Literally, it’s a sequel to a sequel to a sequel.

Charles (1:06:19): I tend to think that there is a distinction between nearly objectively good things versus things that feel specific to a person. There’s something different there. One is being able to recognize and appreciate what a person has done. But another thing is recognizing that this person is talking about something that you feel like you’ve been thinking about for your whole life but haven’t been able to articulate. I hate to use the word taste, but if I were to try and hone in on a definition that I thought was correct, or describe the quality of people who I think have the best taste in the world, it’s more towards the second relationship. It’s a self-knowledge.

Jackson (1:07:29): Right. It’s a self-knowledge thing you keep coming back to. One of the next things I had connects to this. You reflected on having Cory Arcangel as your professor in college. You say the first part of class was everyone talking through some links they found on the Internet. People would bring in things that may not seem interesting at first, but Cory was amazing at parsing out why something might be interesting. It showed you it’s important to think deeply about why you like what you like. First of all, I think that is a really wonderful and generous thing. What do you think made him good at that? To what extent did you learn about being able to do that for yourself from him?

Charles (1:08:18): I don’t want to overstate it and embarrass him, but I think he played a large part in that kind of practice—looking at things with the perspective that it’s kind of like a game. Taking something out of context, whatever the thing is, a piece of media content or whatever, placing it here, and having it be a reflection on you. That move was just a different way of relating to things. I feel like I had experience, but he took it to a different level, in my opinion. I was his first studio assistant after college, and he very generously took me around to see art shows. His studio was in Chelsea, we would go on a lunch break and just go look at shows. He would show me around and talk about how he was looking at things, why something might be interesting, and what the context around something might be. He was also very young at the time and tried to understand this for himself, but he was open source about how he was coming to an understanding. I remember him talking about how a person can just put a mop in a gallery. You roll your eyes, but then you think about where this person is coming from. It was relating to me in a human way—this gestural, conceptual way of relating to things in the world.

Jackson (1:10:19): It sounds both properly critical, but also very personal.

Charles (1:10:25): Yes, that’s a really nice way to put it.

Jackson (1:10:27): Which is something we tend to forget in the conversation about all these things. The taste thing is sort of silly, but I always like to bring up that taste is kind of like a product of eating food. It’s about what I actually like. It’s like we’re going around pointing at all these dishes that we haven’t tried, being like, “This is the good one.”

Charles (1:10:50): That’s why the conversation around this is annoying. When someone says taste is a skill, that is annoying because you’re talking about something that is personal. It’s something that you develop over a long period of time. To me, taste is synonymous with an understanding of one’s own self. When you talk about it like a skill, then you put it in this arena of competition. People are comparing one’s own taste to another’s, which doesn’t really make any sense. It’s like saying, “I’m better than you because I like this.” To your point: I like this hot dog, you don’t like this hot dog, therefore I’m better than you. That is insane.

Jackson (1:11:44): When you put it like that, it’s both insane and also totally plausible. We do that. I want to come back to the competitiveness, but one last thing on this briefly. I think this was in that same Tasteland interview where you said, “There’s no single thing that could convince me that someone has good taste. It’s the composite.” think one implication is that it takes time to evaluate both somebody else and ourselves in taste. Why is duration—and almost a reference to yourself over the course of time—so important in this self-knowledge as you grow through it?

Charles (1:12:35): Part of this class that you were talking about with Cory Arcangel was using Delicious. Basically, the way it worked is you would send links to Delicious instead of saving them to a bookmarks bar. You would look back and see this sort of trajectory: “I was thinking about this thing. This thing was important enough for me to save.” Then a week later, I can draw the connections between these two things. I think the duration is about an ongoing conversation that you’re having with yourself. When you bring up that there’s not one single thing that could convince me a person has good taste, I think about someone who has the best taste in the world: Chris Sherron. He was our original designer, the designer for K-Hole, and a musician. He just has impeccable taste, highly idiosyncratic. I don’t know if this is still a thing for him—I have to air out his taste for a second—but he was for a long period of time obsessed with Tom Cruise. Thinking about that versus every other thing that he likes, it makes sense. But when you just take that one thing, it’s not evidence. It’s the composite, the trajectory.

Jackson (1:14:12): To extend the food metaphor, it’s almost like a dish. This ingredient in the context of all these other ingredients is quite interesting.

Charles (1:14:24): It’s at once refined, but it’s also so specific to him and his personality. When you see the connection in a person with those two qualities…

Jackson (1:14:54): Going hand in hand, that can be really active.

Charles (1:14:56): A self-knowing that can be really active, but also works in the world in a particular gestalt that couldn’t really be replicated by someone else.

Jackson (1:15:07): I like that a lot.

(1:15:09) Performance: Here for Fame and Not Love

Jackson (1:15:09): You briefly referenced the kind of competitive nature of taste. The other big idea you’re working through in that piece, “Here for the Wrong Reasons,” is what you frame as competitive realities. There’s an articulation you have where you talk about the incentive for us to all think of ourselves as brands, and think of information or content as a resource to use in this way. You go on to make an amazing Bachelor reference with “here for fame, not love.” ” You say (1:15:41): Someone whose interests are more strategic than personally intuitive. A person whose interests accumulate with an awareness of how they will reflect back onto them. A person who follows nodal points not from an innate desire, but from the expectation of some kind of reward, social or otherwise.” You also write (1:15:59): “There isn’t a clean way to get around the idea that personal expression is always, at least in part, performative. Expression is partly fun because it’s performative.” Those two are in tension a little bit. The first is this total cynicism—here for fame, not love. The second quote distinguishes that. Your platform, Are.na itself, is actually a great example of this. It seems to be sort of resisting the perils of the first part. But also, all taste is a little performative, even to ourselves.

Jackson (1:16:43): I’m curious how you square those two things. What amount of performativeness is tolerated? Is it about self-awareness?

Charles (1:16:54): I think it’s about motivations and expectations. These are my own rules I’m coming up with, but in my mind, doing it in public and being performative means finding joy in the thing. It’s about showing off a thing with joy, without expecting someone to look at me as someone with good taste.

Jackson (1:17:44): Or that you want a specific reaction.

Charles (1:17:47): You can’t want any kind of reaction at all in this worldview.

Jackson (1:17:54): Is joy performative, though? Real joy probably isn’t very performative. It’s enthusiastic, not internal.

Charles (1:18:05): It’s a rare combination of being able to show the thing with love and do it in public without expectation. I think that is extremely hard and maybe almost naive at this point to expect a child could do it.

Jackson (1:18:25): That touches on the broader theme of competition, which you alluded to earlier. Two more quotes: “Social media has largely made permanent a world of individual realities, but it also underpinned that world with the perspective that the larger structure holding everything together is competition. In order for your reality to be the most real, it has to win.” Second quote (1:18:46): “You have to think of content or information as a resource. In doing so, it means that in some ways you’re producing or consuming in order to cultivate a position rather than treating content as something out there to be curious about, to be fascinated by, or to love.” The last part is the thing hanging over all of this. I was thinking about the idea that in order for your reality to be the most real, it has to win. I don’t know if you still consider yourself an artist, but being opinionated is part of that. I know you’re quite opinionated about software and how you make software. On one hand, great artists are sometimes just loving, but oftentimes they’re saying something. They’re actually trying to have their reality win. Maybe this gets back to the tension we were discussing around performance. Maybe it depends on the context—if you’re just in an enthusiastic learning period versus constructing something.

Charles (1:20:04): A really good example that’s top of mind—I’m making an excuse to bring up “Taste Wars”—is seeing the different ways this plays out on Twitter. People take one side against the “taste is a skill” idea, and others take other sides. It feels like people are trying to align themselves properly. conversation is annoying for a lot of reasons, but one is that it feels like the goal is to end up on the winning side.

Jackson (1:20:50): And to feel better about one’s own position.

Charles (1:20:58): Which is a problem with Twitter in itself. But the other part is talking about the thing you’re doing rather than doing the thing. When you talk about taste, you’re talking about the idea of loving something, not actually putting your attention toward the thing. When I was going to art shows in New York more regularly, it was successful meant something ineffable was communicated to me. I didn’t feel like that was a competition, but an ongoing conversation. plays a large part in the tone. Doing things to dunk on someone or to end up in the right spot is different than thinking about something for a long time and wanting to articulate it in the best way.

Jackson (1:22:15): And by the way, I care about the response, but in a way that is less about my ego. It’s a delicate thing.

Charles (1:22:21): It is a delicate thing because it always comes into play. In one mode, you care about the response because you want the conversation to keep going. You love the conversation so much that you want things to be generative. You want to add to the conversation so that someone else can add to that.

Jackson (1:22:43): The other is to signal.

Charles (1:22:44): The other is to signal. There are percentages of everything in every way of dealing with this.

(1:22:53) Aspirational Attention

Jackson (1:22:53): So much of this is about attention. The piece is really about You just said we have to pick which things we give our attention to; there’s a finiteness to human attention. It’s hard not to think about that in the context of this other form of intelligence we’ve created, where the feature and bug is that it has infinite attention. quote you have that prompted something for me: “If you’re really focusing on the moment, on something you love, on something in the world that feels like it’s made for you, you can’t be thinking about how it will benefit you or how it will reflect back on you.” These two modes are at odds. True attention requires that you don’t view something through the lens of what it can do for you. Can you fake it till you make it on this front? Can you be a poser around it and then end up loving it?

Charles (1:23:58): Yes, I totally believe that. That’s why I’m a poser apologist. If you find yourself wanting so hard to associate yourself with an idea, that means something.

Jackson (1:24:12): There’s some radar happening.

Charles (1:24:14): And if you’re willing to be vulnerable to maintain that position, that’s also very important.

Jackson (1:24:27): The other part of this—what we’ve spent the last ten minutes talking about—is whether it is inward-looking or outward-looking. You have a take on the common advice to do more things for yourself, not for other people. You invert it and say we should point our attention out into the world.

Charles (1:24:52): Yes.

Jackson (1:24:54): Understanding what connects you to the world, your radar, what draws you in—you have to pay attention. Pay attention to what you’re paying attention to. It reminded me of the David Foster Wallace This Is Water speech. That’s really his core contention. He has this line about how you can be trapped alone at the center of a skull-sized kingdom, worshipping some kind of thing for yourself, or you can turn your attention outwards. That was where I found myself going. A possible resolution for this is making your attention more generous. Maybe that’s the question: How does one cultivate that generosity of attention, that external, outward-facing attention?

Charles (1:25:44): The thing I learned from Corey, to go back to what we were talking about earlier, is one can find anything interesting if you look at it long enough or from the right direction. I think the generosity of attention is around that. You don’t have to give in completely to this idea that I could look at this forever. You can’t. That’s unproductive. But you can open up the aperture a little bit. What I was saying to you before we started talking, the thing I really miss about being in New York is just having random conversations with people on the street. That activity reminds me of this idea that anything can be interesting. I found that you could really quickly get into that mode with someone where you both might be looking at the same thing, trying to make a little joke or look at it from a funny angle as a way of relating to each other. You’re very quickly seeing something from someone else’s perspective. It’s about being empathetic to perspectives and understanding that one can look at anything from a million different directions and find a personal way in.

Jackson (1:27:21): It’s a form of looking with some amount of humility. I’m searching for the language—it’s not quite intentionless, but it’s looking with a willingness to be surprised.

Charles (1:27:41): The thing I’m talking about in this piece, or the activity that I’m annoyed by, is another way of looking: “How can this thing benefit me?” I want the object that will make me look good. That is a really to have as your rubric for looking at things in the world, in my opinion.

Jackson (1:28:07): Yeah. What am I going to get from this?

Charles (1:28:08): Yeah, what am I going to get from this?

Jackson (1:28:10): It’s almost looking without needing anything. I appreciate you indulging me on the attention thing. You referenced Nadia Asparova’s Antimatics in the channel for that post, and I had a similar conversation with her. I think the attention thing has just continued to come up. There’s something metaphysical about it. It feels like the one scarcity left.

Charles (1:28:39): It gets metaphysical so quickly. I can be that person for a second, but when you start talking about it, it’s not bullshit. There is no end to the amount of attention that you can pay something. That’s real.

(1:29:02) Designing Generous Tools

Jackson (1:29:02): I want to talk about a grab bag of things I would broadly describe as design or tool making—maybe a form of gardening that you do in shaping Arena. First, on the thread we were on, there’s an interview with you and The Creative Independent back in 2017. You say: “Before, when I was working on my solo show as an artist, I was thinking about what it means to be generous as an artist. At the time, I thought it was about being really personal or really open, to the point of being diaristic or sharing images of me and my family. Towards the end of making that show, I decided, no, it’s actually about tools. It’s actually removing myself entirely and making things for other people to do stuff. I decided making tools is the nicest thing you can do as an artist. So Arena still feels like a natural extension of where I was going. Arena has changed the way I think. I continue to think about things the same way I would as if I were making art, but I just don’t make art.” That was a long time ago. What is so generous about making tools? And maybe more broadly, what makes an artist generous?

Charles (1:30:29): That question is super personal. It’s specific to the person and how they define that kind of thing. For me, that’s the next logical conclusion in the conversation I was creating with myself and the work I was making at the time. The thing that’s generous about making tools is that trying to optimize for reinterpretation. At least that’s how I would approach making tools. These things should be used in different ways. Because I think about tools in the realm of software, I to play with this on the spectrum of open-endedness versus rigid and intentional.

Jackson (1:31:25): You could argue that’s generous.

Charles (1:31:26): There are other parts of it too. What I would want from a tool is what I try and do with Arena. I’m trying to be generous to a person who might share my same perspective.

Jackson (1:31:51): Is Arena art?

Charles (1:31:53): No, I don’t think so. But everyone we employ at Arena has an artistic or creative background. I tend to think that it’s harder to learn how to make creative decisions in business than it is to learn the practical parts of running a business. So it’s not art, but I like treating decision-making within the context of running a business as a creative act.

Jackson (1:32:45): If I’m to infer correctly, your baseline implication is that it’s easier to teach creative people business than to teach business people.

Charles (1:32:54): That’s what I think. But I’m sure a ton of people would disagree with me.

Jackson (1:33:00): On the note of design specifically, you reference this old 37signals blog post about making opinionated software. They say the best software takes sides. Then this is you (1:33:14): “We tend to approach the problems we solve from a cultural perspective rather than a purely technological one.” Maybe those two ideas aren’t exactly related, but they felt related to me. I’d be curious for you to explain that distinction. With the lens of taking sides, what does it mean to approach something from a cultural perspective? One simplistic reading would be that it’s not mechanical, it’s not the bare metal. It’s much more soft and amorphous.

Jackson (1:33:47): Human thing.

Charles (1:33:49): Yeah. I use Arena myself as a person. When I say we approach things from a cultural perspective, I mean we understand what we would want as people who use the software. We see how our community uses it, what they come up against, and what frustrates them. Those things might be table stakes, but it is a rare case to make software you are the user. A lot of people try to make smart business decisions, but smart business decisions shouldn’t be the number one reason why we do things. We ask, “How conversation? How will this change the dynamics of what people are doing on Arena?” Because we use it ourselves, we don’t want the quality to dilute. That is the number one thing.

Jackson (1:35:15): Are you conflating business and technology there?

Charles (1:35:19): I think so, a little bit. I can’t say that we don’t make strictly technical decisions, because we spend a ton of time just trying to make things super fast.

Jackson (1:35:32): Right. But there is a meta thing here: technology wants something. We often think of technology as being value neutral, but it’s not. Maybe that’s the other force pushing up against this. What does the platform want?

Charles (1:35:48): There is “what does the platform want,” but there are also things we are opinionated about. It should be faster than is reasonable. It should be very minimal. It shouldn’t have too much of a feeling. Content should come through way more than the Arena interface. We think about those things as qualities in themselves, but also what kinds of behavior and feelings those qualities engender.

Jackson (1:36:25): In that sense, they are cultural decisions. I was going to say they’re almost like taste decisions.

Charles (1:36:33): The weird thing about being opinionated is it can sound like taste, or it can sound like being principled. But really, it is just having an experience of using software over our entire lives, understanding the things we think are well done, and trying to emulate and push past those qualities.

Jackson (1:37:07): On this note of what the platform wants to be, the way you talk about it often feels like the classic gardening approach—bottom-up versus top-down. You say: “It often feels like Arena itself has its own needs and desires, that Arena has its own personal intuition, and that we are figuring out what it wants to be together. We try to listen to how we all talk about Arena, pay attention to how changes to the platform bring about new needs and ideas, and recognize the times when we have strong urges to do something on Arena but can’t. These are the times when we know how to make Arena more complete.” That goes back to the principled stuff you just said. I’m interested in embodying the feeling. Could you give an example of what is happening when there’s something you want to do but can’t? I suspect there have been times when, given that you are principled, there are things you feel like you want to do that aren’t right.

Charles (1:38:21): I’ll give you a counter-example. The most frequent feature request over the lifespan of Arena is seeing channels in a graph view, like a nodal map. We’ve explored it, and people have explored it with our API. We keep coming back to the conclusion that it’s just a novelty and doesn’t actually provide anything.

Jackson (1:39:01): It gets tried on every product.

Charles (1:39:03): And it feels like it would be valuable, but from the way we use Arena, it doesn’t deliver in the way you think it will.

Jackson (1:39:20): Almost like Arena doesn’t want that.

Charles (1:39:23): Yeah. Fortunately or unfortunately, that’s our particular take. It’s also one of the reasons why we’re opinionated that Arena should always have an API. That is feeling like a radical position. The things that live on Arena have no algorithm. It’s people categorizing information.

Jackson (1:40:01): What a waste of time.

Charles (1:40:06): It’s a wild thing to think about, and I think it is inherently valuable. At the same time, we believe there are interpretations of what Arena can and should do that someone should have the ability to enact if they want.

Jackson (1:40:26): It’s almost two spiritual aspects of the platform that are at odds, but you’re allowing them to exist in slight tension.

Charles (1:40:33): I think so.

Jackson (1:40:35): I know Ted Nelson has been very influential. two ideas: mediums are infinitely harder to create than media, and parallelism is an essential part of thought. ” You also said (1:40:54): The key is that Arena isn’t doing the work for me at all. It’s just an environment that is oriented to this type of activity.” That gets at the medium idea. I would call Arena a medium. What has been most important in creating that environment? Why has parallelism or bidirectional linking been so important to create this type of environment that produces what you want?

Charles (1:41:30): To put it in dumber terms, we’re trying to find the optimal conditions to get at the kind of content we want. In order for that content to come in, one has to have the quality of being fascinated with something. The structures of Arena—even the positions we take as a business, like saying “no algorithms ever”—are the conditions that have to exist in order for the good content to come through.

Jackson (1:42:23): It’s a very strict constraint or prompt.

Charles (1:42:31): Because it has a learning curve, it has an open-endedness that feels ungenerous at first.

Jackson (1:42:40): It’s a threshold.

Charles (1:42:42): It’s a threshold.

(1:42:44) Space in a Product and Fading into the Background

Jackson (1:42:44): One idea that comes up a lot is this idea of space. You say, “I don’t always want to be augmented; I want space in my software.” It’s just a bunch of people recognizing that it’s really hard to think when you’re attached to the internet all the time. In your piece on Bohm Dialogue, you say: “It’s so easy to treat technology as though it can prescribe a solution to a particular problem. Software developers build complex workflows, create new methods for faster communication, and tune information delivery to an individual level. But what humans really need is much more simple: time and space to think and process.” There are two core articulations of space that fit Arena. One is negative space, a gap. The other is spatial interfaces. Both are deeply seated in how you design this product. I’m curious to the extent they interact, and why you seemingly keep coming back to negative space.

Charles (1:44:17): It’s about what we do, but it’s also about what we don’t do. Deciding not to do graph things, be too heavy on animation, or design an interface that looks too slick in one particular direction is another form of space. It’s letting the person’s content and intention come through more than what we’re doing. It’s a fine line. It should look good, but also not really too much of anything. That’s a really hard thing to pull off, but that’s what we aspire to.

Jackson (1:45:15): That’s a good transition. One of my favorite things I read of yours is the blog post on Areal, your new typeface—a misspelling of the proper Arial. Johannes Breyer at Dynamo, who designed the font, says: “It’s a system font. So at another stage, it also became a kind of non-choice for a certain type of graphic designer who didn’t want to make a point of choosing a new font. But of course, choosing to go with the default is also a choice.” The question became (1:45:56): “If we want to make a font for Arena, but they already have the perfect font, how can we update Arena’s identity with a meaningful gesture?” Finally (1:46:04): “The hope is that you can’t really spot a difference. Looking at Areal and Arial should feel like refreshing a browser page. It’s the same, but it isn’t.” He even references Kristen Sue Lucas, who refreshed by changing her legal name from Kristen Sue Lucas to Kristen Sue Lucas. I’ll read one last quote from you: “When we made this interface change, our desire was to be as default as we could so that Arena wouldn’t get in the way of the content. In other words, we wanted Arena to look good, but to fade into the background as much as possible.” Fading into the background is a little oxymoronic. In theory, all design should not show up, but it’s such a delicate thing. It’s hard for me reading the Areal thing. I know that it was functionally better for you, but it almost reads as performance art.

Charles (1:47:16): It is, but it’s not. The new Areal… I did a presentation a couple of days ago in a class and realized that the computer I was showing it on did not have our Areal. I could tell the difference immediately because the kerning on the original Arial is so fucked up. When you look at new Areal versus old Arial, it’s minor, but there is a real difference.

Jackson (1:47:45): Maybe the essence of great design fading into the background is not that it’s unnoticeable, but that it might have to be pointed out for you to notice. You should feel the benefits without noticing them.

Charles (1:47:58): Yes, that’s exactly right.

Jackson (1:48:03): Only in actually looking at the old version would you notice.

Charles (1:48:09): Now there’s no way to look at the old version. I guess you could modify the CSS on the new Arena and see the difference. It wasn’t purely gestural; it has real utility. To us, the original Microsoft Arial was nearly perfect. Johannes and Fabiola, who worked on our Areal, made it 100% complete. To us, that’s so satisfying. It’s part of this contextual whole that makes it very special and beautiful without looking like too much of anything.

Jackson (1:48:59): How do you conceivably justify something like that, given that you have very constrained resources?

Charles (1:49:07): Honestly, it was a partnership between both of us, so it was just a fun thing we both got to work on together. We don’t have the same kind of relationship with Dynamo that a huge startup might have. Johannes and I are friends.

Jackson (1:49:25): It’s also time. But the answer can also be that you wanted to, and that you wanted to do something for the community.

Charles (1:49:32): Johannes approaches Dynamo in the same way we approach Arena: we love working on it and find it endlessly interesting. The collaborations we try to do now are with people we want to work with because it’s fun and because we share a similar way of looking at the world.

(1:50:01) Why Creatives Should Be Entrepreneurial & Building an Independent Business Online

Jackson (1:50:01): My last two sections go together, about effectively building independent software businesses. You alluded to this earlier, but you are clearly an advocate for creative people starting businesses. You’ve said (1:50:25): “We have a very limited conception of the type of person who starts a business, especially tech businesses. When I talk to artists, young creative people, I always recommend starting a business.” And: “Arena itself is what drives me to be entrepreneurial in order to make it more resilient.” You wrote somewhere that you felt complicated about your first commercial art show, and yet you have a seemingly very healthy commercial relationship with this project. Maybe it’s because it’s not art, as you said earlier. But you also talked about how patronage requires answering to a very specific person, whereas the commercial part of a business can be a freeing container. I’m curious about the spectrum between patronage and business as a fuel to do something creative. How do you think about what a business is and what it allows for? What drives you to persuade more creative people to adopt this kind of fuel?

Charles (1:51:37): There are a couple of reasons for software in particular. I think the Internet and the web would be infinitely more interesting and healthy if there were just different takes towards what making a business online is. This is especially true for businesses like ours that have a cultural or social component. I don’t think that the ways in which we think of being social online represent all the ways that one could be social online. I don’t think this particular type of way of funding software businesses is going to find all of those ways of meaning.

Jackson (1:52:27): Like the venture capital industrial complex. Maybe I should let you finish, but the obvious critique here would be that the reason we don’t have more of these is we don’t have the business models for them.

Charles (1:52:39): That’s what I mean about creative decision-making. I don’t think that Arena’s business model is by any means creative. Subscriptions in our case is a business model that is really symbiotic with how we want to work on Arena because we’re providing an environment. The question is just: do you find this environment valuable enough to help us continue, maintain, and build it? The relationship is so simple that it is almost radical at this point.

Jackson (1:53:24): You said somewhere you’re the only social network that its users pay.

Charles (1:53:34): Maybe that’s not entirely true, but it’s definitely the only social network where the relationship between the people who make it and the people who use it is really understandable. It’s very straightforward. I think that there are much more interesting ways of figuring out different setups for that, and ways that people who are using software and people who are making software can be more aligned.

Jackson (1:54:05): To borrow a frame from my friend Chris, business model/product fit in this context is actually quite rare.

(1:54:12) Patience, Durability, and Antifragility

Jackson (1:54:14): I think another piece of your business model isn’t that creative, but you have something else that’s rare, which is a whole lot of patience.

Charles (1:54:23): Part of the other thing that is radical about Arena is just that we keep continuing to do it. There’s a commitment to it. It’s also why I try and illustrate this relationship that we have as people who are using the product. We’re in the same place as people who don’t work on Arena. We’re right there. If something frustrates a person who’s using it, it probably frustrates us too.

Jackson (1:54:55): I thought it was cool to look over on the note of patience. There’s one line where you say, “Success as a business relies on people who love Arena enough to pay for it. So getting to 400 paying customers was a big deal for us.” Now that you’re about $70,000 in revenue, you’re now at 18,000 paying users.

Charles (1:55:17): It’s going to be 20,000.

Jackson (1:55:19): Nearly 20,000. Over $100,000 in revenue. Has it gotten easier or harder to be patient?

Charles (1:55:26): Much easier. For the longest time, when we had to do other things to functionally exist, like do freelance projects or work other jobs, it was just exhausting. I feel like we’ve reached the ultimate goal. To be able to work on Arena all the time is the bag. We’re motivated to continue that and make it stronger.

Jackson (1:56:05): You’re coming up on your 15-year anniversary this year.

Charles (1:56:07): Yeah.

Jackson (1:56:10): A quote I really loved: “One question that is still hard to answer after 10 years of working on Arena is: What’s the long-term vision? This is difficult for a few reasons. One reason is that we have to calibrate our definition of long-term with the person who is asking the question. Arena is a lifelong project. Our ideal outcome as a company is not becoming the next Facebook, God forbid. It’s becoming the next Nishiyama Onsen Keiunkan, a hot spring hotel in Japan and one of the world’s oldest businesses, around 705 AD.” You go on to say, quoting Dune: “The slow blade penetrates the shield. I do think it’s worth considering slowness as a strength.” It is amazing to imagine a business that old. Especially amazing when you think about a digital software thing in that way. I guess my question is, beyond just being patient and being intentional, what has or what will make Arena more antifragile for the chance of lasting another 15 years or beyond?

Charles (1:57:21): Lasting another 15 years is one thing. I think lasting past us retiring is a different thing. A thing that Arena has going for it in that regard is it’s almost nothing. As a piece of software, it’s extremely unique. It’s complex, but compared to other things, it’s not that complicated. It this structure that could be remade in different forms very easily. I sort of go back and forth about this, but I think that one part of its strength is it’s a software, but it’s also an orientation. The orientation is something that can manifest in different ways.

Jackson (1:58:18): It’s funny you say that. I didn’t do the research, but my expectation is that the onsen probably hasn’t been the same building. I don’t even know if it’s been the same land. But there’s some thread. When you think about that durable of a time frame, there are asterisks, but there’s some thread.

Charles (1:58:41): I think the orientation is simple: this is a piece of software that the people who are making it are deeply committed to, use as individuals, and feel like they need as a part of them. The other businesses that I look to for inspiration have this same quality. They feel to me like they also gesture towards longevity.

Jackson (1:59:25): Can you give a couple of examples?

Charles (1:59:27): I’m not the hugest Obsidian user, or I’m not a complex Obsidian user, but I appreciate that as another manifestation of an orientation that is manifest in a piece of software, and how those two things play back and forth.

Jackson (1:59:46): My

(1:59:49) Personal Businesses

Jackson (2:00:03): last primary section is about an awesome piece you wrote recently about personal business and a natural thread of building independent businesses. To set the tone, here a few quotes from you: “When I started running Arena with friends 14 years ago, it often felt like having such a personal stake in what we were doing would be a liability. Today, it’s often perceived as an asset. I’m not especially pro-capitalism, but I am pro-doing something really hard that you care about desperately and unabashedly.” You alluded to this earlier, but: “I wouldn’t be running a business if it weren’t for Arena. It’s a very personal business, meaning that it is something I want to see in the world. It is a tool that I would personally be devastated if it were to not exist.” And finally (2:00:41): “I’ve never wanted to walk away, even when we ran out of money. I think it’s the coolest thing on the Internet. I don’t know what else I would do.” Can you make your case for more people starting these types of personal businesses?

Jackson (2:00:59): Maybe especially digital or software ones.

Charles (2:01:01): If you’re the type of person who feels critical of the way social interaction happens online or that your relationship to information is compromised—and there are probably a billion people who fit this qualification—it is easier and cheaper than ever to create software. People can figure out ways of playing around with this stuff and feeling the right shapes and orientations of things. It’s a very important place to experiment because it’s ridiculous that there’s just a single type of person making this type of software.

Jackson (2:02:07): I think there’s been a huge shift, especially in the last six months with Claude and what’s happening with LLMs. The disposition towards making software is that you can just do things. Perhaps the implication is that generally only one type of person is doing this. Ideally, there is a lightness to it. However, the negative aspect is that it definitely doesn’t feel like the way you talk about a personal business. It isn’t heavy, meaningful, and caring. It’s just throwing stuff out.

Charles (2:02:37): I mean that the resources are available if you feel opinionated about these types of things. You can start to shape your opinions easier than you might have done earlier, like when learning HTML or PHP. My process for learning how to write software took a really long time. One doesn’t have to spend that amount of time now in the same way. There is a limit to what I’m saying, though, because I don’t totally believe that you could do these things at a scale that would be meaningful just yet.

Jackson (2:03:18): Give it four more months of Claude, who knows?

Charles (2:03:25): I think there are a lot of young people with weird and opinionated ways of how they want to interact with the world and with each other. They are figuring out more interesting ways of manifesting those behaviors online. It feels important. The drive and motivation has to come first. You need the feeling that something should exist that doesn’t already exist, and that maybe there’s a way for you to try and articulate that.

Jackson (2:04:02): Perhaps there’s a group of people who have that perspective but have the technical ability in short supply. It goes back to your earlier point that maybe more creative people should start businesses, but they are unlikely to. That is the thing the software world has been lacking: people who have that kind of perspective to approach it from a new angle. We’ve had a lot of people approach it from a specific kind of way.

Charles (2:04:30): A lot of people approach it from a specific way, with the expectation that making a software business will follow a particular timescale and trajectory. There is an expectation that these things will ultimately cease to exist, or that the point is to cash out at some point.

Jackson (2:04:57): I don’t know your history of Arena. I don’t know if I have all the details, but you were kind of eating glass for a little while. You definitely weren’t working on it full time. I think that goes back to being personal. It’s like saying, “I need this.”

Charles (2:05:13): I can think of people who are doing this kind of thing and are in this phase of figuring out how to make it their full-time thing or their life’s work. It feels super positive. It’s an interesting thing to try and pitch. Consider the possibility that working with your friends on something that you think is cool is the most luxurious possible thing that you can do.

Jackson (2:05:55): Independent of the reward.

Charles (2:05:55): The reward is the work—that you get to hang out with your friends and make something cool. That is the reward. Figuring out a way to keep doing that is the challenge, but it’s easy to do once you start experiencing it.

Jackson (2:06:13): To wade a little further into the waters of a template for this, you talk about offering products, services, or experiences that are both high quality and idiosyncratic. It’s the type of business that both sustains and is sustained by a community. I’m curious what you think about the shape of businesses, products, or customers that What is it about that relationship that is productive for these types of businesses, whether it be something like Arena or the local grocery store? Is it intimacy?

Charles (2:06:55): It’s something about intimacy, but it’s also about infrastructure. It’s providing an armature for other activity to happen within, so that someone can rely on that.

Jackson (2:07:17): It can become theirs.

Charles (2:07:19): It can become theirs, but there is a dependability that comes over a long period of time.

Jackson (2:07:28): I was texting you about this yesterday. In the “This Time It’s Personal” Arena channel, you have this incredible SoftBank deck from 2010 where Masa is hardcore vision questing. He has a slide about happiness, saying happiness is about being touched—touched by seeing, interactions, love, learning, playing. He says that whenever you get lost, look into the far distance. This is how SoftBank is going to go from its 30-year vision to his 300-year vision. One of the things you texted me was, “We need that Masa back.” This prompted the thought that maybe all founder-led businesses are personal. If so, do people just sort of forget why they’re here?

Charles (2:08:17): That’s a good question. Part of it has to do with the typical way most large software businesses are funded and the expectations of growth. The way they are funded, the expectation is an exit in some form. It’s not typical that a company might get investment and pay dividends over time. For me, this is related to another question that sometimes comes up when someone on Arena feels it’s getting a little bigger. They ask, “Do you think Arena can get too big, or do you think its quality will diminish as it grows?” My answer is usually that it can grow really big; it just has to do it slowly enough. The issue is mostly the timescale expectations of a business, rather than the fact that it’s getting big.

Jackson (2:09:40): Maybe that applies especially to a community or social thing. There is probably a broad analogy around all growing living things: it is not good to grow too fast. It reminds me of a meeting I had with somebody at LVMH. They were talking about how it’s actually bad if any of their brands grow more than 15 or 25 percent year-over-year. When you’re in the business of 100-year brands, you don’t want a 200 percent year. That actually shows something is wrong, or you’ve totally mismanaged supply and demand.

Charles (2:10:20): Well, that’s inspiring.

Jackson (2:10:24): It was cool.

(2:10:27) Grab Bag: Authenticity, Bohm Dialogue, Skate Boarding, and Keeping Things Personal

Jackson (2:10:27): I have just a few more miscellaneous things. I thought I would ask this before we got here, but what do you think of the word authenticity?

Charles (2:10:38): This came up during the “Here for the Wrong Reasons” essay. In the same way that I’m a poser apologist, I’m a bit of an authenticity apologist. I believe that one could fully understand themselves, as I was saying before. That is synonymous with authenticity.

Jackson (2:11:06): The fact that you believe it is possible, or at the very least is worth approaching?

Charles (2:11:13): Authenticity is possible because it’s possible to get better at understanding oneself.

Jackson (2:11:20): In fact, you almost… I must be an optimist. I can’t remember where I found this: “It’s generally a good idea to try to apply metaphors to places where they don’t quite fit.” I think that’s from you.

Charles (2:11:35): I said that.

Jackson (2:11:35): I think so. It’s possible I got it from some other channel, but it felt representative of something that is happening inside of Arena and the patterns.

Charles (2:11:43): Absolutely. That’s the thing I was talking about earlier: it’s useful to try and look at something with the frame of mind that it could be interesting. It’s applying a gaze to something that might not be there implicitly.

Jackson (2:12:03): Right. Ready to see what might be there. You have a piece about it. I didn’t get to fully deep dive the David Bohm dialogue stuff, but I’m curious what you think we can all learn from that. What stood out to you in your research, or what was he getting at in dialogue that was really unique?

Charles (2:12:25): It is a super big topic. who had a long trajectory towards simplifying his overarching message, going from hard physics to thinking and thought. He wrote a book called On Dialogue, which proposes a practice where a bunch of people sit in a circle to have a generative conversation. The point is that everyone is supposed to add on to what another person is saying. Ideally, you get to a place where everyone is sharing a thought, and you are all looking at it “out there,” viewing it from different angles. Laurel Schwulst and I organized a Bohm dialogue once, and it was really incredible.

Jackson (2:13:49): How is it different from hanging out with 10 people?

Charles (2:13:52): There is an intentionality and setting to it that changes things. You are supposed to lay out very simple rules. Essentially, you can’t change topics; you have to add onto things. You end up talking about talking and thinking.

Jackson (2:14:21): But it’s structured and generative.

Charles (2:14:23): It’s not so structured; it’s very open-ended. It’s structured only in that it is focused. One comment I remember described it like the cartoon where a train is putting the track ahead of itself while it’s going. That is how a good conversation feels. When you have that good conversation stretched out to 10 people, it’s super interesting.

Jackson (2:15:00): So the number is critical?

Charles (2:15:00): I think the number of people doing it is part of the thing.

Jackson (2:15:12): I’m excited to learn more. You said earlier you could talk for two and a half hours about it. What else have you learned from skateboarding?

Charles (2:15:28): Like art, skateboarding has a snobbiness to it that can feel like being principled, but is actually something slightly different. There are One person describes the middle of the board as the “forbidden 14,” the 14 inches that one should not slide. You can’t do a board slide, but you can do nose and tail slides. One should not do any slides that involve the middle of the board. So there are all these random, made-up rules that act as principles for what is correct. They are all arbitrary and made up by people, but they come across as principles.

Jackson (2:16:25): It’s funny in a sport or activity that is so punk in so many ways and not about the rules.

Charles (2:16:33): When systems are entirely open-ended, people make up those sorts of rules. It’s the same framing that happens on Arena. Someone decides, “This is an open channel that is a guestbook. I’m calling it a guestbook, and this is how you interact with it.” Behaviors emerge when a system is open-ended like that.

Jackson (2:16:56): We didn’t talk about it, but I enjoyed perusing your “Rules are Rules” channel. It’s fun—the freedom that comes from certain types of arbitrary constraints. Borges… you listed him as one of those key early influences. Did an ex-girlfriend’s friend introduce you? I’m curious if anything really stood out.

Charles (2:17:23): The Library of Babel is a short story that has obvious connections not just to Arena, but to people thinking about hypertext. Do you know this one?

Jackson (2:17:33): I haven’t read it.

Charles (2:17:35): It is super short; you can read it tonight. It’s basically about a library that is infinite in all directions. Every book has a certain number of characters, and it contains every permutation of those characters. Librarians wander this library looking for a book that has any kind of phrase at all. Most of the time, you go into a room, open a book, and it’s just nonsense.

Jackson (2:18:05): It’s kind of like the monkeys.

Charles (2:18:08): Exactly. Sometimes you’ll go into a room and find a single phrase that is the right phrase at the right time.

Jackson (2:18:18): Will you have any chance of bringing back directions to lastvisitor.com?

Charles (2:18:21): I should do that, but I don’t know if it’s possible anymore. Directions to Last Visitor was a website that you would go to, and it would geolocate you and give you Google Maps directions to the person who visited the website before you.

Jackson (2:18:43): Automatically pulling their latitude data.

Charles (2:18:45): Right. That is also the reaction most people had to it—that it was some sort of privacy violation. But the point I was coming from was removing myself from the equation and letting two people make this connection without me.

Jackson (2:19:15): I believe the Delaware C Corp name for Arena is When It Changed. Why was that moment so meaningful?

Charles (2:19:25): That comes from William Gibson. He has a trilogy of books called the Bridge Trilogy, and it’s a post-apocalyptic situation. The apocalypse moment is never really fully described, but it’s called “When It Changed.” In the early days of Arena, there were multiple eras where we were reforming and reforming this corporation. When we finally got control of it ourselves, we called it When It Changed. We’ve had a million William Gibson references. Our first mobile app was called Case. If there’s any consistent naming scheme, it comes from Gibson stuff.

Jackson (2:20:18): On the Arena Influences channel, there is a tree that owns itself. Do you know what this is?

Charles (2:20:31): I didn’t put that in there, but now that I’m thinking about it, John Michael Bolling put that in there. I don’t even know if that’s an artwork. It’s just a situation that exists that he has always referenced as a major thing. I think he was actually pointing to something really early that we’re pointing to now, which is just that somehow this thing should have a life of its own that should exist outside of the people who made it.

Jackson (2:21:12): For people who don’t know, this is a tree that apparently somehow legally owns the small area around it that it is on. Also apparently called a Jackson Oak, so I will take the name.

Charles (2:21:26): Nice.

Jackson (2:21:26): Just a few more things. There’s an interview with Kelly—I’m forgetting her last name—where you were asked what are the things you’d like to do in your life that are doable. I’m going to read the list. Number one (2:21:38): Switch Back Tail Shove, which I googled is sick. So sick. Number two (2:21:44): Nollie Crooked Grind. Number three (2:21:45): Pivot Fakie. Number four (2:21:49): Read In Search of Lost Time. The top four alone were already really great. Number five (2:21:54): Keiretsu, which I think I looked up and I don’t know what it is. Six (2:21:57): Pass on Arena to future employees. And seven (2:21:59): Run a small used bookstore. Any reflections, any additions? Any updates on this list?

Charles (2:22:05): That was a very recent list. I was trying to think of things that are infinitely doable. With the skate ones, there’s a limit to how long one can skateboard for. I’m essentially past that limit.

Jackson (2:22:26): Brian Johnson’s going to figure it out for you.

Charles (2:22:29): Thank you, Brian Johnson.

Jackson (2:22:30): You get metallic limbs or whatever.

Charles (2:22:34): Those are doable tricks that are also within this weird rubric for what I consider to be tasteful skateboarding. is a thing that Japanese businesses did at one point where two complementary businesses would buy shares of each other or exchange shares to solidify a harmonious relationship. We also imagine a future world where Arena has this relationship to other people’s businesses that we take inspiration from.

Jackson (2:23:17): Marrying them together or something. I brought it up before we started recording, but one of your longtime channels is the Secret Agent. It remains quite secret and mysterious, but I’m curious if you can impart any insight for the rest of us on what’s going on in there.

Charles (2:23:42): I know exactly what seeded that. There was a toy when I was a kid called Spy Tools. It was a black light, a little alarm system, a fingerprinting kit, and all of this stuff. I loved the look of it; I can still imagine the logo. But the thing that is interesting about that to me now, apart from these literal secret agents, is what part mystery plays in making a concept or an idea attractive. What is the level of mystery that something has to have that makes it compelling?

Jackson (2:24:24): I was thinking of my walkie talkie watches at one point. You said, “I like every age more than the last.” Any advice on making that more likely?

Charles (2:24:41): That’s a little bit of a manifest. I’m trying to manifest that idea, that sentiment in myself. I do like every age more than the last, but sometimes it’s hard to like every age more than the last. I like having had a really long relationship—in the context of this conversation, to something like Arena—to have a project that I feel I can work on for the rest of my life. Having that time span to me is super special. I realize how lucky I am and we are to be able to have that. The benefit of experience—I do see a lot of value in that.

Jackson (2:25:31): You’re deep into the compounding. This is a quote from the Arena Influences channel: “What strikes me is the fact that in our society, art has become something which is related only to objects and not to individuals or to life. That art is something which is specialized or which is done by experts who are artists. But couldn’t everyone’s life become a work of art? Why should the lamp or the house be an art object but not our life?” That’s Foucault. How do you make sense of what art is?

Charles (2:26:12): It’s funny, but I do think it is about being able to make decisions that are creative. What is creative is, from my perspective, most personal. So any kind of decision making could be creative if it’s coming from this particularly personal place.

Jackson (2:26:40): One more thing should probably come as no surprise. In the film You’ve Got Mail, Joe—Tom Hanks’s character—is telling Meg Ryan’s character… What’s her name? “Kathleen Kelly.” “Kathleen, that it isn’t personal.” To which she replies, “I’m so sick of everyone saying that. That just means it wasn’t personal to you. But it was personal to me. It was personal to a lot of people. What’s so wrong with being personal anyway? Whatever else anything is, it ought to begin by being personal.” How do you try to remember to keep things personal?

Charles (2:27:28): For Arena at this point, it’s automatic. I actually have to try not to make everything personal. If I imagine a world where Arena didn’t exist and I was compelled to make another business, I think about how I would tune that relationship. Setting up a scenario where you are the person using the thing is the only way to do that. It has to be something that you’re sufficiently opinionated about and invested in.

Jackson (2:28:22): That’s all I got.

Charles (2:28:26): Thank you.

(2:28:28) Thanks Again to Notion

Jackson (2:28:28): Thanks again for listening or watching. I’d like to thank Notion, Dialectic’s presenting partner, one more time. As I mentioned at the top of the episode, Notion is a tool that allows you to have leverage across the work, ideas, and writing that are most important to doing what you do. The way they think about AI and agents is all about giving you more leverage to focus on the things that really matter, allowing you to have deeper attention on the real work. Meanwhile, you can delegate the incremental work, busy work, and synthesis to Notion’s AI and agents. I found it’s even helpful to have Notion AI give me a second set of eyes as I parse through the most important ideas in my research or review my conversations after the fact. You can check out Notion at notion.com/dialectic and learn about how Notion has evolved in recent years to give you more leverage, particularly with AI and agents. You can find all the links and full transcript for this episode at dialectic.fm/cab. That’s dialectic.fm/cab, where I’ll have a transcript, links, and all the platforms the episode is available on. Once again, thank you so much to Notion for presenting Dialectic, and thank you for listening and making it all possible. I hope you’re inspired, and I hope you give your attention more deeply and more generously. I’ll see you next time.