16: Not Knowing

Game designer Warren Spector once described his dream project: a roleplaying game that takes place within a single city block, packed with all the apartments and shops and weird and wonderful characters you'd expect.

Since then, other game designers have latched onto the "one city block" idea, imagining perfectly miniature worlds trimmed with the precision of a bonsai tree. As opposed to the wide, expansive landscapes that typically characterize RPGs, wouldn't it be nice to have one that resembles a diorama?

As far as I can tell, the city block idea is mostly about emphasizing the depth and richness one can achieve in a microworld, the Warhammer 40K of game design concepts. While it seems Warren was agnostic as to how complete it needs to be, it's hard to ignore the implications. Many iterations of the city block idea seem to resemble what I think of as the "locked room" genre. Escape rooms are one example of this, where everything you need to understand the game is contained within a finite space. To make sense of one's surroundings is to win the game itself. Meow Wolf, an immersive art exhibit near Santa Fe, New Mexico, is another example of a locked room game: you explore a house that seems to have no purpose, but eventually a story unfolds.

But locked room games only work by, essentially, distracting you. They have the immersive feel of an open world, but they aren't truly open, because the designers quickly introduce a plot to focus your explorations. It becomes less interesting to poke around empty drawers (unless you are like me, a completionist) once you know what you're looking for. The city block fantasy, by contrast, hints at the hope of completeness, even in an open-world context. Thus, the impossible dream.

I've thought about how I would make this game, but there's something about the city block's premise that I find fundamentally unsound. In a real city block, your world is filled with incomplete narratives and unlived lives, doors you can't open, people you can't ask questions of, clothes you can't tear off in the middle of the grocery store, even if you technically could. You might never learn why that woman was crying on the bus, why that man from the bar never texted you back, or why your neighbor seems to come home angry every day. And that's kind of the beauty of it. City blocks aren't closed ecosystems, but places where mysteries are forever unsolved, answers are never found, and everything you want to know always seems just tilted out of reach. Life goes on without knowing.

My version of this game, then, would look not like a diorama, but a Polaroid. It'd introduce questions, prompting endless reflections as to what’s going on outside of that frame, or inside the minds of the people who occupy it. No matter how intimately you familiarize yourself with every square inch of the game, these are the only clues you'll ever have to go on. Like the planchette on a Ouija board, the magnifying loupe moves across the board, spelling out one maddening letter at a time, before returning to its original position.

The flawed promise of microworlds, in my view, is that we think we'll know more if we could only focus our attention onto a smaller surface area. But if anything, I think the opposite occurs. Zooming in -- to people, ideas, places -- can make us even more aware of how little we know, leading us to grasp desperately for more, because the intimacy we have never feels like enough.

I have some friends with whom I talk exclusively about ideas, yet I know very little of their personal lives. With other friends, it's the reverse. It's tempting to say that certain friends just don't know me as well, but I think maybe it's just that all friendships can only ever take place on narrow bands of knowing. Even friends who've known me forever experience a different version of me than friends who've known me for a year. Of the things we do know about each other, we know them well, touching all the shapes and contours like a ritual until they feel smooth. What differs an acquaintance from a friend isn't how much they know about you, but how much you value one another. These friendships can still feel "complete" without stuffing more detail into them. (I especially feel this way about internet friends, although coworkers might be another classic example. The people who know the most about my day-to-day are often the people who know the least about how I got here.)

When I reflect upon the relationships I've had that felt most satisfying, I similarly realize that it was never about how much we revealed about ourselves, but how much we showed up for each other. The hardest ones were when what we had didn’t feel like enough, where we felt we needed to know more, do more, be more to each other, scooping up every last bit of ourselves and pouring it into a bag to hand over to another person. I find these relationships challenging, maybe for the same reason that "one city block" is considered an impossible game to make — because we can't ever completely model our inner selves and externalize them to another person. If the expectation is completeness, you'll inevitably hit disappointments as you find more holes, more flaws, more things that are missing. The search for completeness will become all-consuming. You'll keep looking for every last missing piece, gathering them greedily up into the sack, instead of seeing what you have in front of you.

Perhaps this is the Before Sunrise game design fantasy: capturing those fleeting, intimate moments in time that can stretch into infinity. Rather than lamenting what's lost, it's when you realize you can't know everything — that the narrative of your circumstances will remain forever inscrutable — that you've won the game.

P.S. I moved this newsletter party over to Substack, in case you can't tell, mostly because I know I'd have to move off TinyLetter sometime, and Substack seems to be the most writer-friendly brand out there. Anyways, when I imported my old posts, they looked kinda sad sitting meekly in the Substack archive, because they all had this "Things that happened in X" subject line. So now they’re all getting proper subject lines. (Side note: The rebel in me has thoughts on the unintended effects of WYSIWYG editors on our brain spaces...maybe for another time.)


Posts I’ve written this month.

  • “Writing Hypertext” (interview with Kicks Condor): I’m still on a bit of a blogging hiatus while I wrap up book writing (sorry!), but I realized I forgot to share this conversation I recently had with a new internet friend. We talked about blogs, newsletters, and personal websites in the context of public-private spaces. I found it fun and refreshing because well first off, Kicks has a pretty sick website! (Ya gotta check it out.) And secondly, because it was nice to do an interview that’s not about open source ;)


Notes from this past month have been updated. A few highlights:

  • (from a group convo) “Wedding cake” (scientists who want to make things perfect) vs. “cookie” process (engineers who can take those ideas and make millions of them)

  • Science vs. tinkering (discovery through philosophy/theory vs. practice). Problem with tinkering is you can have a collection of practices that work out overall, but they inevitably include some practices that are completely ineffective, and you don’t know which is which

  • Is the scientific method the lean startup methodology of science? (somewhat trolling here, but: both sorta propose that science, or startups, can be distilled down to A-B-C, and also that you can generate innovation through empirical methods. Both are also flawed/incomplete for this reason, IMO. They sanitize the mysticism/tinkering/practice from the process)

  • Request for product: a publisher who just consolidates popular writers’ blog posts into books

  • The LinkedIn problem is a lot like the Patreon problem, now that I think about it. LinkedIn loses out over Twitter or Instagram bc it’s not the place where ppl actually talk to each other, i.e. show what they can do. Without a good social layer, it’s just a glorified resume website. Similarly, Patreon loses out over native platforms (Sponsors, App Store, Spotify, whatever) on funding bc it’s not the place where ppl actually talk to each other. Without distribution layer, it’s just a glorified payments processor


Useful articles I’ve read this past month.

  • “Why We Can’t Figure Out Why Infrastructure Is So Expensive” (Josh Barro): A few months ago, I tried to learn how we measure the value of physical infrastructure and discovered it’s deliciously difficult, maybe impossible, for the reason given here: the value of infrastructure is highly contextualized. For whatever reason, I get a weird thrill out problems that inherently defy measurement. I kind of love-hate this idea that infrastructure has been around for forever, we obviously need it, yet we still can’t appraise its value. Sort of like a six year-old dancing in bare feet around a group of scientists.

  • “When Alchemy Works” (Anton Howes): We think of alchemy as a fool’s endeavor today, but it turns out there are a handful of examples of alchemy actually “working”. A tale about the dissonance between understanding from observation and understanding from theory. Also, apparently a bunch of governments banned the transmutation of gold, fearing its repercussions, because they took it so seriously. Who knew?

  • “Who Would I Be Without Instagram?” (Tavi Gevinson): A thoughtful reflection from a woman who grew up child star-famous on Instagram. This isn’t your typical “woe is me” influencer take; rather, it caught my eye because it’s written in the tone of someone who is thoughtfully chewing their bite of salad over lunch before answering your question. In addition to giving a firsthand account of the breaking up of traditional media, and the interplay of platforms and creators who build their brands on them, I particularly liked Tavi’s description of splitting into public, semi-private, and fully private selves. I think short-term we tend to see this as problematic, but long-term, we’ll all learn to manage, and perhaps even relish, the ability to create and manage multiple versions of ourselves. (“Point the atomizer ray-gun at me next!”, we’ll scream.)

  • “Randomizing His Life” (Max Hawkins): Someone recently told me about this guy who rolled the dice on his life for a few years in order to break out of his default world and experience new things. That meant living in randomized cities, taking randomized Uber rides, eating a randomized diet, and adding randomized events to his calendar. Bonus: he made a bunch of these tools available for other people to use.

  • “Minimal Maintenance” (Shannon Mattern): A piece highlighting the costs of maintenance, and how it can be a limiting reagent to growth. I have an almost allergic twitchy reaction to the concept of “degrowth” as a good or even necessary thing, but something in here made me think about what open source developers often do in practice, on a per-project basis. The whole system grows, but each open source project becomes more disposable, more throwaway, to reduce the costs of maintenance. So one way I can understand Shannon’s argument is to think about pruning away the marginal costs of maintenance in order to allow the whole system to grow; in this sense I don’t think it’s really “degrowth” we’re observing at all, but perhaps just a transition to modularity to meet the scale of demand.


Relevant books that I’ve read this month.

  • The Hidden Dimension (Edward T. Hall): I thought this book was going to be about the influence of social behavior on building design. It is, but there’s a lot more biology in here than I expected. The “hidden dimension” refers to the unconscious physical distance we each like to keep around ourselves -- explored through the expression of all five senses -- and how it plays into the design of our living and working spaces. Normally I love this kind of crossover, but I found myself getting impatient for some reason here, especially since I assume a lot of the science is outdated (it was published in 1966).

  • Recursion (Blake Crouch): I was just looking for something fun to read, but this ended up reminding me of the tyranny of ideas post I wrote. Among other things, this story is about whether it’s possible to undo technology once it’s invented. It’s a slow (yet entertaining) burn, but the deeper you go, the more it builds on itself, until you suddenly find yourself being like, “I don’t know how you got me here, Author, but good on you”.

15: Modernization


I'm just getting back from Indonesia, where I spent part of my childhood. It was my first trip back in twenty years, so I was curious (and a bit nervous!) about what I'd discover when I unearthed this memory lockbox from the soil and cracked it open.

Jakarta's roads are like a system of pneumatic tubes, where everyone zips around in their silver capsule of choice. Nobody seems to go outside at all anymore; the sidewalks are eerily devoid of people. They're all tucked away inside buildings, cars, and motorcycle helmets, making faces that nobody will ever see as they grimace and honk their way through the traffic.

I keep thinking this place is a dystopia, more than any other city I've been to. It's rapidly sinking, there's nothing for tourists to see, and even the government announced they're moving the capital elsewhere. I think about the electric scooters I recently rode in Los Angeles -- another car-heavy city -- and realize that micromobility would be a joke here. You can't walk anywhere, much less ride a bike. Sitting in the backseat of our car in stop-and-go traffic, my mom and I remark somewhat jocularly that this is actually a pleasant experience, getting around like this, but I know it's only because we're shielded from the elements by a reflective hunk of metal. Our comfort indoors is a sign that this city has failed at coaxing its denizens outdoors.

And yet, I felt so comfortable there. Jakarta felt like being nestled into a warm basket of knitting yarn, tangled up in motorcycles and cars and blue glass and red-shingled roofs and humming and buzzing, interspersed with frequent punches of jungle greenery and polite but insistent honking. It felt cozy, even amidst all the chaos. Maybe especially because of the chaos.

Mom and I can't seem to agree on whether Jakarta has gotten better or worse. When I look through the eyes of my childhood self, I'm pleased by how clean and safe it seems. I try to explain why I think it's gotten better by pointing to the absence of things: No more hordes of beggars wandering between cars in the traffic. No more orange becaks zipping through the streets, spewing black smoke. No more men standing ominously by the road who make you pay them to "direct traffic". No more children selling themselves as extra passengers to meet carpooling rules. No more red taxis that rob passengers.

Today, the city seems quieter, sleeker, and more predictable, with fewer game pieces in play. Many of the motorcyclists sport Grab (Uber's Southeast Asian partner) or Gojek (a play on ojek, or motor taxis) jackets. There's a bus and subway system now. All the taxis are Bluebirds now, the safest and most reliable company.

But our strongly divergent reactions to Jakarta makes me wonder how much I can trust my own memory. In the same way that dogs love to roll around in dirt and gobble chicken bones off the street, maybe the warm memories that cling to a child's brain are everything that overloads the senses: the smell of sewage, the rubble of broken glass and ceramic tiles in the park, the howling of stray dogs. Maybe I'm doomed to have a forever innocent, childlike relationship to this place, like my dad, whose eyes shine when he talks about his "first love", Berlin, even while telling me in the same breath about the Russian tanks pointed at his window.

Because then we go to the J.W. Marriott, and they search our car and our bags and make us walk through a metal detector, and my mom reminds me that this place got bombed -- twice -- since we've been here. We have lunch across the street from the Ritz-Carlton, and we realize that got bombed, too. We revisit our old house, the first one we lived at, where we were once robbed, men bursting through the doors with guns and machetes. Now it's been torn down and a big, sturdy-looking mansion is in its place. "This area's shaping up!" I remark brightly, stepping over the cracked speed bump and eyeing the broken basketball court across the street, and I really mean it. I didn't even remember there were paved roads. But then our driver casually remarks that an entire family was killed in their home right around the corner from here, not too long ago, and now I'm not so sure.

Maybe this city is better than the childhood version of me remembers, but it's still objectively bad by any adult's standards. Maybe. I really can't tell, no matter how hard I look at it. I keep trying to see it through the eyes of a complete outsider, or a native like my mom, both for whom this place seems to provoke more troubled emotions. Would I feel the same way about Jakarta if I weren't clouded by nostalgia?

Jakarta is more modern now, but is modernity the same thing as progress? And how can any of us know the difference? I feel increasingly uncertain whether my heuristics -- the absence of bad things -- are signs of progress, rather than just anachronisms, no different than if I were to time travel and reopen the capsule of my life in the 1990s here in the United States. It's easy to demonstrate that our standard of living has improved -- we have iPhones, Google, Uber -- but without the counterfactual, how do we know that our rate of change is beating the market? Maybe these are cosmetic distractions from a social game that doesn't ever fundamentally change.

I don't mean to imply that modernization isn't worth striving for. I'm not pessimistic about the future in any way, but I find myself craving more precise terms, like "improved safety" or "increased access to opportunities", that give us a concrete basis for comparing the past to the present to the future, because memories are so subjective. It's too easy to construct a narrative about how things are getting better or worse, without knowing what those words really mean.

When I wrote briefly about progress in here a few months back, someone responded with the question: "Progress towards what?" Progress is a dangling participle; it needs something to modify to make it meaningful. Without it, progress suggests that we know what the world is "supposed" to look like, but maybe that ideal is an intangible concept, like Gatsby's green light stretching interminably into the distance. Maybe what the world is supposed to look like is exactly as it is right now.


No new writing this month! I’ve been enjoying a little break.


Notes from this past month have been updated. A few highlights:

  • Wish it were easier to try new notetaking apps without transferring everything over. Like some universally recognized format (like HTML, RSS) that I could store all my notes in, and then I could export it and upload it to different notetaking app interfaces until I find one I like

  • Is maintenance just a subcategory of curation? What is the relationship between creator, curator, and maintainer roles wrt a single piece of content (or community)

  • Stoicism is the new David Foster Wallace

  • A Pattern Language, but for elements of social architecture online (e.g. The Comments Section, The News Feed, The Like, The Replies Between Mutuals, etc - the evolution and function of each, when one element is more or less useful to employ than another, etc)

  • An amusement park where you get to play with heavy construction equipment

  • I wonder if "influencers" are actually sort of recursively-defined communities? Ppl (otherwise unassociated with one another) gather around a single point of focus, but the act of them all being there in itself creates a meta-community that then also influences the influencer (in terms of what they put out). It’s not quite collaborative between members like a typical community, it’s something else


Useful articles I’ve read this past month.

  • “Recap of the `funding` experiment” (Feross Aboukhadijeh): I try to avoid including “current events” in here, but this writeup was really good. Feross did an experiment where he ran postinstall ads for one of his projects, StandardJS. The public reaction was predictably mixed, and Feross decided to stop running the ads, but he documented his reasoning and process in this post. I admire that he went for it, despite the pushback, for the sake of moving public discourse forward about how open source developers can and should make a living. Need more experiments like this.

  • “You will probably not understand this” (Sabine Hossenfelder): On the gap between what people in research think they’re saying, versus how people actually receive it. After reading this, I realized that doing research makes me feel like I’m a two year-old who is desperately trying to communicate, but can’t yet form words. Also, I discovered Sabine’s blog through this article, which is a quirky little corner of the internet! Physicists are cool. Here’s a piece she did about why the multiverse is religion, not science.

  • “How Life Sciences Actually Work: Findings of a Year-Long Investigation” (Alexey Guzey): Alexey spent a bunch of time talking to people in life sciences about the state of their field and wrote up his observations. I so love anthropological deep dives like this. Also, props to Alexey for the intellectual honesty in concluding that scientific progress isn’t slowing down, given that the opposite is a popular position right now.

  • “The Twitter Transparency Paradox” (Rick Paulas): Rick muses out loud on the topic of journalists who are active on Twitter, and how it can help or hurt their brands. (Apparently 25% of verified accounts are journalists or publications!) I’m interested in the ongoing “unbundling” of news firms into individual journalists who build their own followings, as I think there are useful parallels between that and open source (there’s a similar transition happening from funding projects -> funding individual developers). Also recommend reading Sonya’s email to Rick, which he cites in the post.

  • “A Party Room and a Prison Cell: Inside the Friends writers’ room” (Saul Austerlitz): An excerpt from a book about how the show Friends was written. Reading this piece made me think about the mythology of (hear me out) Bell Labs, and how we look up to organizations who “do things differently”, aka let creative people run loose, but often find that success hard to replicate in practice. One of the big themes in here is how the head writers of Friends “did things differently”, elevating junior writers and treating them as peers. But you could just as easily read this piece as an exercise in controlled governance (the head writers were solely responsible for the emotional content, leaving junior writers free to write pure comedy).


Relevant books that I’ve read this month.

  • The Art of Community (Spencer Heath MacCallum): I’ve been looking for reading about commercial buildings as microcosmic “cities” and finally found this book, published in 1970, through a friend. Within the first few pages, I wanted to reach across the fifty-year divide and clasp hands with the author. MacCallum asks, “Is a hotel a community?” and proceeds to explore the idea of “proprietary communities”, such as shopping malls, airplanes, and RV parks, where unaffiliated individuals are bound by the contracts they make to the proprietor of an organization. MacCallum argues that sovereignty (or "institutionalized force") is merely an awkward transition between “primitive” and proprietary communities, both of which represent the true best form of social organization. (Unsurprisingly, his grandfather was an ex-Georgist.) I didn’t agree with everything in this book, but it left me with a lot of good questions. It made me think about the ways in which big tech companies are also proprietary communities (consider the recent WIRED piece about Google’s internal culture!). It also gave me some missing vocabulary I’ve needed to express how one-to-many communities are structured differently from many-to-many communities (ex. an open source maintainer is often a sole proprietor who allocates scarce resources, like attention, on behalf of all contributors). I desperately want to talk to someone about this book; it looks like I snagged the last copy on Amazon, but it’s also available via Internet Archive here. Perhaps one day some kind soul will republish this book and give it the love it deserves.

  • Just Giving: Why Philanthropy Is Failing Democracy and How It Can Do Better (Rob Reich): Philanthropy is sorely lacking on interesting analysis and discourse, so I was excited for this book. After reading it, I felt that we've arrived at similar conclusions (foundations aren't reaching their full potential; we don’t think critically about the role of philanthropy in society; etc), but maybe for different reasons. Reich leans heavily on arguments about equality and redistributive justice, which I’m not as moved by. Regardless, I find his endeavor to develop a political theory around, and rethink the value of, philanthropy to a democratic society to be extremely important. And I strongly share his view that foundations should focus on funding individuals and pre-market opportunities; I think this is where tech philanthropy will differentiate itself long-term. If you’re going to read one chapter from this book, I recommend Chapter 4.

  • The Hike (Drew Magary): Why haven’t I included fiction in here before? I guess I felt like it didn’t fall under the definition of “relevant books”, but I don’t even know what that means anymore, so whatever. Here's some fiction. This book is about a guy who goes on a hike, takes a wrong turn, and ends up on a bizarre journey. It’s like Fight Club meets Castaway meets The Odyssey. A lot of the scenes are violent, which normally I avoid, but I found myself strangely into it here, maybe because the narrative moves so quickly. Also because I’ve kinda been in the mood for some nose-punching sci fi thriller fiction lately (apparently I have some aggression to get out of my system?). Send me recommendations if you have any!

14: For the love of war

I recently spent a relaxing week in Utah climbing rocks, splashing around lakes, and exploring canyons. Breaking out of my daily routines reminded me how all the things that had previously hardened into stone could come to life again.

Instead of the $4.50 + $1 tip Ethiopian blend served in artisanal earthenware at a third-wave coffee shop, I sipped strong black liquid from a hefty mug every morning and watched horses amble by my front door. Instead of the 4.7-star Uber Eats order I get delivered to my house every day, I ate watermelon, tomatoes, and burrata. Instead of the hyperoptimized 19- and 32-minute daily walks between cafes, I wandered into gas stations in the hot dry desert middle of nowhere and scavenged for Sour Patch Kids and Gatorade. I chewed on jerky and stared out the window at sand and rocks. Lots of sand and rocks.

Driving for hours across Nevada, I looked at my phone to see what music I wanted to play and realized that all my music is now “productivity music”: the stuff I play to strap in to writing sessions, or alternately to cool down between sessions without losing focus, or to turn my brain off after sessions. I enjoy it, but I don’t listen to music for “fun” anymore. It's more like a drug, a cheap form of wireheading to induce my brain to finish the work I need to get done.

It’s not just music, either. So many things I used to do for fun are now just props for getting things done. AirPods in, Spotify on, coffee and pastry in hand, PAX to numb off extraneous thoughts, medium-length walks in the park to process ideas, books to keep the rhythm going, Mario Kart to squeeze my pupils down into tiny, focused dots. My body is a marionette, and I’m my own puppetmaster.

Some years ago, I watched a standup special from Iliza Shlesinger called War Paint. The title comes from a line where she says: “This isn’t a bra, it’s body armor. And this isn’t makeup, it’s war paint!”. That line stuck in my head over the years, because I think it so wonderfully encapsulates the female experience: how these symbols, often mistaken for weakness or deference, are actually declarative acts. If you do them right, people don’t even realize how hard you’re working, like a duck paddling below the surface, and that’s kind of the fun of it. (Hence the age-old debate: “You don’t need to wear makeup!” “That’s because you’ve never seen me without makeup before.” “Wait, are you wearing makeup right now?” “YES.”)

Writing by myself, six hours a day, for the better part of a year requires transforming all the beautiful things around me into stone, then grinding it into dust. During World War II, phonograph records were commandeered into tires, bacon fat melted into bombs, nylon stockings pulled apart and refashioned into parachutes. Music, games, and walks through the park are not really enjoyable to me anymore, even they appear to be indulgent vices. They’ve been repurposed into body armor and war paint to help me get through my day.

Creative people tend to shy away from war metaphors. They talk about “following your heart” and “expressing yourself”, with the occasional, insolent lapse into hedonistic nihilism. But if making things were light and happy all the time, creative people wouldn’t be so infamously miserable. Making things might be an act of love, but it’s also an act of war.

I guess this might be read as a sort of sad reflection, but I don’t really think there’s room for emotion during wartime. You just do the things you need to do to get through it, and then you pick up the pieces and figure out how to get back to civilian life.
There’s a scene in the first episode of Sherlock where Dr. Watson is captured by a stranger in a suit who calls himself Sherlock’s “arch enemy”. They’re squared off in a dark warehouse, silhouettes illuminated by floodlights. You’re meant to feel afraid on Watson’s behalf. He’s just returned from war, he’s seen some terrible things, and now he’s found himself compromised once again in London. But then Sherlock’s arch enemy points to Watson’s hand. We realize that Watson isn’t afraid at all: quite the contrary. He’s not suffering from trauma, he’s suffering from withdrawal. His hand is steady now, because he craves the feeling of war. This is exactly what he wants.

The danger of war is that it’s fun. We lie to ourselves during wartime, telling ourselves that when this is over, everything will go back to normal, and that’s when we’ll finally relax and enjoy all the things. But after one war ends, another always begins. We're addicted to its taste, the oily way it slides around and clings in our mouths.

On our first day in southern Utah, we went through a difficult canyon: squeezing through walls, shimmying into dark passages, rappelling into quicksand and murky pools up to my waist. I ended up covered in mud, elbows scraped, clothes torn and wet, my shoes squishy and smelling faintly of animal poop. When we finally made our dizzying ascent out of the canyon and began the two-hour hike back to the car, I felt weak with relief, legs stumbling beneath me.

The next day, we unanimously decided to do a shorter canyon to even things out. The canyon was enjoyable, but walking effortlessly between its narrow walls and clambering over the rocks, it felt...easy. Too easy. So much so that the person who was most afraid during our adventure the day before remarked, “You know, something is missing. I’m missing my adrenaline.”

Why do writers write, when it makes them so miserable? Maybe it’s because they feel the need to express themselves. That’s the spiritual answer, anyway. The carnal answer, muffled between sinewy bites of flesh and bone, is that they like it.


Posts I’ve written this month.

  • “Being basic as a virtue”: I wrote about the joys of being basic, and wonder whether it will eventually become a status symbol for knowledge workers.


Notes from this past month have been updated. A few highlights:

  • Theory around why open source software has succeeded where open science seems to have stagnated (haven’t deeply thought this through, but it’s an idea): software developers don’t tend to directly make money off the code they release, they have day jobs. Whereas in science, in the end you’re judged by your publications / citations. Your value is directly tied to continuing to buy into this closed-off system. So they can’t really make the choice to do things differently, unless it’s stuff they’re doing just for fun (is there an equivalent of weekend projects for academia? Research that ppl do just for fun, in addition to their day job?)

  • Twitch / gaming figured out moderation faster than other social platforms for a lot of reasons, one I think being that e.g. Twitter etc started out as a many-to-many use case and then slowly is trying to backwards adapt to the one-to-many use case. Whereas livestreams were one-to-many from the beginning, with a more clearly defined space to moderate (eg. rooms or streams), vs this big wild frontier of e.g. all of Twitter

  • Two social use cases that I want to see more of: 1) “One-way mirror” (creators put stuff out there, but audience doesn’t participate back) - YouTube videos / Insta w/o comments, newsletters, etc. 2) “Fly on the wall”: Conversations bw mutuals in public (audience doesn’t participate in the convo, but they get to witness a conversation they wouldn’t otherwise be able to join) - podcasts, twitter mutuals, wechat, etc are examples of this

  • I think what I find cool about the antilibrary thing is it shifts the idea of books from being a conduit of information -> being an asset. You can value a book for the ideas it contains, and/or, you can value it for its aesthetic appeal, social signaling, etc. Books don't need to be consumed to transmit value


Useful articles I’ve read this past month.

  • “Intellectual Dark Matter” (Samo Burja): A piece about knowledge (lost, proprietary, and tacit) that we know exists, but isn’t necessarily visible for various reasons. "What is knowledge" is maybe one of my favorite topics that I feel guilty spending time on because I worry it has no obvious practical application, but I can’t stop thinking about it anyways.

  • “Building a Memex” (Andrew Louis): After I wrote about thinking out loud last month, a friend shared this cool project with me, where Andrew is building software for an externalized brain. I’m not sure what the project’s status is, but I had fun digging through his newsletter archive. It’s a treasure trove of trivia and interesting thoughts about externalized brains. (So meta!)

  • “Why I’m Stopping the Fan-Supported Podcast Experiment” (Tim Ferriss): Tim experimented with donations instead of ads for his podcast, but switched back to ads. In a funny way, his audience prefers ads for the same underlying reason that subscriptions often work elsewhere. Tim has a close relationship to his audience, and they want his product recommendations, so they love ads. I think this experiment highlights how there isn’t a one-size-fits-all solution to funding content. It's easy to hate on ads, but what works for a given audience really just depends on their underlying motives and behavior.

  • “The Reality of Depending on True Fans” (Kevin Kelly): You’ve likely come across KK’s “1,000 True Fans” essay, where he argued that creators don’t need a mass audience to make a living off their work. I hadn’t seen this related post before, which includes a statement from a musician named Robert Rich about what it’s like to have a thousand true fans. While Robert agrees that creators can survive with small audiences, he also talks about the downsides, and how it can be not-so-great to feel like “a tadpole in a shrinking puddle”. Thought it was a good, honest reflection to balance out the optimism of micro-scale patronage mechanisms.

  • “We are in a golden age of illegal sports streaming and it’s showing us how copyright infringement can result in better content” (Ryan Regier): I don’t watch sports, but I’ve been secondhand witness to the pains of streaming sports online among my peers (ok, ex-boyfriends). Anyways, don’t ask me how I ended up on this Medium post, but I liked the conversational style. It felt like sitting at a bar and asking a Canadian dude about his views on illegal sports streams. I particularly enjoyed reading about Velocityraps, a mysterious person in Egypt who streamed NBA games internationally to hundreds of thousands of people and took Bitcoin donations. To the author’s point: “This is a fascinating revelation about illegal streamers. Even though people can acquire content for free from them, they still give them money.”


Relevant books that I’ve read this month.

  • Closure (why the lucky stiff): A wonderful compilation of essays, vignettes, and drawings from a Ruby developer who unexpectedly quit programming and disappeared from the internet overnight, returning only once to transmit this book. Told through some very amusing, autobiographical-but-not-true stories. I referenced it in this month’s blog post,

  • The Crowd (Gustave LeBon): The back cover tells me that this book influenced such “masters of crowd control” as Freud, Hitler, and Mussolini. Hmm. Yikes. I’ve been feeling sort of bored with the “mobs are bad” narrative, though, so I tried to learn something new from this book. Here are two unexpected takeaways that I had: 1) In addition to great evil, crowds are uniquely capable of great heroics (ex. space race, railroads, cultural norms and traditions). 2) It’s not that “smart people” manipulate the masses. Everyone regularly switches modes between individual and groupthink, regardless of intelligence, and nobody is above crowd behavior. (P.S. This book pairs well with Eric Hoffer’s The True Believer.)

  • The Ph.D. Grind: A Ph.D. Student Memoir (Philip Guo): I never cease to be amazed by how much Philip’s publicly recorded about his life and work process. It's so delightful to peer into someone else's brain. This is a book he wrote about his experience getting a Ph.D., and a cathartic read if you’re in the midst of a long and lonely grind.

13: Thinking out loud


I’ve been thinking about a certain interpersonal dynamic between friends, the one where someone wants to talk at length about whatever’s happened to them recently, or perhaps reflect upon a past experience. They go into storytelling mode, where their eyes glaze into a faraway look, their expression becomes fixed, and they speak in animated, yet measured tones.

You don't interrupt someone in that mode. [1] As a friend, you know it's time to stay silent and refrain from commentary. This isn't a dialogue, it's a brain dump. You just sit, nod, let them do their thing, and hold all questions til the end.

Similarly, I keep a journal, but I also have a therapist. Our sessions don't really resemble a conversation, so much as me rushing to pour out all the words from my head into some glass vase, and her occasionally nodding and asking guiding questions before our time runs out.

Why have a therapist when I can just brain dump onto paper? Because there's something to be said for thinking out loud: not just to yourself, but in the presence of others. [2]

I tend to assume that writing serves one of two purposes. We either write (i.e. type) privately to ourselves, or we write to communicate with others. The former gets ossified into “personal knowledge management” systems (notetaking apps, voice memos, blogging tools), the latter into social media (Twitter, Instagram, YouTube, group chats).

But thinking out loud is neither of these things. When we think out loud, we’ve made a deliberate choice to externalize our thoughts, but we're also not really trying to have a conversation.

I often hear people say that they use Twitter as a notebook of sorts: a way to record their thoughts out loud. I definitely don’t use Twitter this way, but I do think of blogging, newsletters (hi!), and note-publishing as a form of journaling in public. I explicitly don’t want to write for others, but publishing my thoughts is still part of the process. I’d feel incomplete if I kept those thoughts stowed away in private documents, and the reason has nothing to do with getting likes or views.

Personally, I tend to use Twitter and Instagram as scrapbooks, where I collect bits and bobs that fit a certain aesthetic I like, which is why I use both platforms pretty sparingly. But this is yet another version of thinking out loud. Why tweet screenshots of something I’ve read, when I could just save them on my phone?

Regardless of which platform we use to think out loud, it feels like there’s some underlying set of needs that we’re trying to fulfill, which neither journals nor conversations completely address. Here's a few that I came up with (if you think of others I’ve missed, please share!):

  • Rubber ducking: Analyzing, working out an idea by articulating it to someone else

  • Brain dumping: Recording, remembering, creating an “externalized brain”

  • Scrapbooking: Collecting, curating, arranging ideas

  • Signaling: Feeling heard, connecting, emitting a beacon for likeminded people (arguably this is a form of communication rather than thinking out loud? I think of it more like passive signaling, e.g. wearing certain types of clothing)

  • Playing: Having fun with ideas, externalizing the silliness in our heads. Being funny requires having someone who’s listening, even if you're not explicitly trying to talk to them

Thinking through this list, it seems that different people each use different social, collaboration, or personal productivity tools to meet these needs. I'm hard-pressed to think of products that are explicitly tailored to the "thinking out loud" experience, and it feels like we’re lacking certain features within our existing tools. What would those look like?
I think there are two parts I’m interested in. One is this idea I keep coming back to: creators behind one-way mirrors, where people can read and receive your stuff, but not necessarily interact with you. Externalized thoughts are more experimental than what you might post to social media, so they need to live somewhere quieter than in full public view. RSS, newsletters, and podcasts accomplish some version of this.

The other part is that I want to reduce the friction of getting stuff from my brain out into the world. When I’m thinking out loud, sometimes I feel like my fingers can’t type fast enough. Text-to-speech / transcripts for audio memos, lightweight publishing process, simple reading format, and easily searchable history would all be very helpful.

Longer term, making it easier to think out loud gets us closer to creating externalized brains. I really love the idea of externalized brains a way of giving other people raw material to play with, learn from, and reinterpret for themselves. I don’t think social media gets us there, because what I say to an audience is different from what I say to myself (the curse of the fortune cookie). I want to find more ways to say things to myself out loud, and I want to be able to access that equivalent for others, as a way of getting to know the people I follow, or am otherwise interested in, more fully.
[1] If you’ve ever watched Avatar: The Last Airbender, I like to think of this as entering the Avatar state.
[2] “Learning in public” is another version of this that I like.


Posts I’ve written this month.

  • "Hidden cities": A post about internet subcultures that are semi-public, but don't necessarily want to be found


Notes from this past month have been updated. A few highlights:

  • (from convo with a friend) Vine as Pompeii: a ruined city, but preserved for all time

  • Intellectual labor is the new working class ("mining of ideas"), the new luxury is gonna be to not engage in anything that drains the mind at all. "Basic as high-end" -> non-intellectual / non-status signaling as high status. Kinda relates to vgr's stuff on mediocrity. But I think it goes one step further: mediocre implies self-awareness and choice, basic says you never even had to try. The god of mediocre is sloth; the goddess of basic is an ingénue

  • Seeing the state of someone’s desktop is kinda like seeing the inside of someone’s home, with all the value judgments that come with it

  • Thinking about what a Freudian interpretation of left-right politics would look like, i.e. “rebelling against public space as parental authority”

  • Shorter feedback loops as a means of grasping towards the future we so desperately crave, but actually longer feedback loops might be better to make actual progress, bc shorter leads to incrementalism? i.e. is accelerationism just a form of incrementalism?


Useful articles I’ve read this past month.

  • “Why I’m Leaving Medium” (Tiago Forte): Fantastic read on the value of paywalls, based on Tiago’s experience, which summarizes my feelings on how paywalls are frequently misunderstood. Paywalls aren’t about monetizing the content itself. They’re a filtering mechanism for creators, who use them to make their readership more meaningful. (Also pairs nicely with the Something Awful piece below! SA became a paid community not to make money, but to filter out the trolls.)

  • “Fuck You And Die: An Oral History of Something Awful” (Taylor Wofford): Something Awful marked a time in my life that I’d like to believe bears no resemblance to my present day, one in which I ate way too much Domino’s and actually had Photoshop skills. (To be clear: I’d still eat Domino’s every day if I could.) Given that I knew nothing about Silicon Valley-flavored “tech” back then (ah, what a time), it’s shocking to realize how much SA influenced internet culture more widely. Also, lots of good nuggets here re: how early online communities are capable of enforcing norms and sanctions in ways that social platforms can’t really do today.

  • “Everything is Fertile” (Nick Cammarata): I loved this personal essay about finding novelty in the mundane, and how our own minds provide more opportunities for adventure than any external stimulation.

  • “The Dark Forest Theory of the Internet” (Yancey Strickler): Yancey’s take on how online social activity increasingly takes place in private or semi-private spaces, and how they resemble physical spaces more than social media. I’m not quite sure that Liu Cixin’s “dark forest” theory applies here (vs. simply, say, “dark matter”), but I still love seeing more people talk about the weird, growing social space between public and private. (I’m probably just salty because I’ve been honing my own “dark forest” theory on an entirely different topic, so maybe this means I need to expand my repertoire of metaphors beyond sci fi bestsellers.)

  • “Load-Bearing Internet People” (Eric Raymond): This was maybe more of a personal ‘whoa’ moment than anything in the content itself. Eric Raymond, who wrote “The Cathedral and the Bazaar” -- a piece that defined a generation of open source as something accomplished through the collaboration of many, rather than one -- recently published this post about how some individual developers are more “load-bearing” than others. I can’t describe the feeling I had when reading this, but it was sort of queer and warm and strange all at once. The times, they truly are a’changin.


Relevant books that I’ve read this month.

  • In the Beginning...was the Command Line (Neal Stephenson): Once upon a time, Neal Stephenson fell in love with an operating system named MacOS, who eventually stomped on his heart. After wandering about in a “Jungian fugue” and questioning the purpose of operating systems at all, he found love again, this time with Linux, who he met unexpectedly in Palo Alto thanks to a Dilbert cartoon. This is his love letter to an ex, in which he explains why he doesn’t need her anymore, because as mesmerizing as he finds each toss of her glossy mane and chiseled exterior, he’s better off with Linux, who, despite possessing the rude, hulking mannerisms of a barmaid, knows how to treat him right.

  • Perplexities of Consciousness (Eric Schwitzgebel): I want to find a counterargument to the premise of this book, because I liked it too much. Schwitzgebel argues that our self-reported experiences are the least reliable way to anchor ourselves in the world compared to our physical environment (as he puts it, “the uncharted wilderness is behind your eyelids”). Until now, I think I’ve explicitly operated on the reverse: I tend to see our external reality as malleable, while our subjective perception can’t be argued with. After reading this book, I’ve tried to invert my locus of thought: external is “known”, while my internals are fuzzy and unknowable. (An example of unknowability: I’d previously assumed I dream in color, but when I really think about it, I’m not sure that my dreams, nor consciously recollected memories, can be described with color at all.)

12: Lines and fixed points


Sometimes when people say things to me, I picture their sentences diagrammed on a blackboard, with soft gossamer trails of hidden meaning streaming out beneath, like a bubble wand dipped into solution and dragged across its underbelly.

We use language as a consensus layer to interface with other people's minds, but every spoken word contains a stack trace of alternate meaning. If I want to understand someone better, I just listen for the echoes in the words they express, tapping to hear the hollows, tracing with my finger the shapes of each muffled sound scrabbling around itself, then chiseling them into my mind, like a Rosetta Stone.

The content we create is no different. There's the object you ultimately end up with, which you can share around with others, but it was made by remixing elements that already exist. Information is like energy: it's neither created not destroyed, but merely transmuted through a series of chemical reactions into new stable forms.

Once I started thinking of content this way, it felt as though all the points were scattered around me into lines, the sun striking a glass vase at just the right time of day, sending rainbows dancing about the room. We tend to value code, words, and media based on what we can see: the stable item, the cabochon jewel gleaming opaquely in the palm of one's hand. But rotate it, cut it into facets, and hold it up to the light, and a thousand new worlds reveal themselves.

Pick up a snippet of code, rotate it, and see how it catches the light. Pick up a tweet, a blog post, a paragraph of a book, rotate them, and see how they catch the light. Every object contains the fingerprints of its creator, and it tells two stories: one is the visible thing in front of us, which is identical to everyone, whereas the other is derived from personal meaning.

I think we struggle to properly assign economic value to content because we keep treating these lines as fixed points. Content, like language, is a function of the people who interact with it. It's why liking a post, and following the person who wrote it, are two separate actions. One is a point, and the other is a line.

I was reminded of this when reading about the lawsuit brought against Conan O'Brien for allegedly "stealing" someone else's joke. As Conan helplessly pointed out, given the volume of content that's created today, sometimes two people just come up with the same joke. And so if everyone's writing the same jokes, the joke itself doesn't really carry value anymore. Rather, it's valuable because Conan told it, and not "a man in San Diego". While this poses an existential threat to the idea of intellectual property, I don't think what got us here is going to get us through the next era of content creation.

There was a time when we didn't see a piece of wood as anything but a piece of wood. Once we realized there was more than we could see with the naked eye, it opened up new avenues of exploration. Similarly, we still treat content as dead objects, with no additional value or complexity beyond what every other person can see. But I think if we stop viewing them as commodities to be bought and sold, and instead treat them as dynamic organisms, we'd see there's a lot more that we need to figure out how to value.


Posts I’ve written this month.

  • “The Twitch argument for GitHub Sponsors”: I kinda binged on streamers this past month, so when GitHub launched their Sponsors payment feature, I tried to think about it through lessons learned from Twitch streamers. Namely, can GitHub help attach status to individual maintainers?

  • “The rise of few-maintainer projects”: I wrote a piece for Increment magazine’s open source issue last month. It’s about the transition from open source projects as communities -> individual creators, which contains some nuggets of the longer piece I’m working on.


Notes from this past month have been updated. A few highlights:

  • Generalists are good at identifying and synthesizing and exposing problems, but they don’t usually have enough skin in the game to solve them. I think this is also why interdisciplinary fields have useful but limited application

  • Thinking of group chats not as chats, but as chatrooms: physical spaces where you can drop in and see who’s around. Messaging apps are ostensibly asynchronous, but actually also synchronous?

  • Service dog status is the medical marijuana license of urban pet owners

  • Thinking about how maybe progress isn't actually linear, but cyclical: diff ideas that take turns becoming more/less prominent at diff times. To me, this is not at odds with an optimistic view of the world, in the same way that understanding bull vs. bear markets is neither nihilistic nor cynical, but observational. Also what I don't understand is if progress IS always "going up", is it asymptotic? Is it possible to ever be "done" or is progress always expanding, like the universe? I think it's weirdly maybe EASIER for me to think of it as cyclical, then, rather than linearly upwards

  • Maybe we assume the world is making progress bc we make local progress in our own brains (I learn all these things as a human progressing from age 0 to age 90 or whatever) and extrapolate up to global scale


Useful articles I’ve read this past month.

  • “The Gentle Side of Twitch” (Nicole Carpenter): A look at the people who read books, knit, and paint on Twitch. I liked that she highlights the wide spectrum of relationships that creators can have with their audience: everything from “a musician performing to a stadium-full of fans”, which are more performative, to quieter streams that feel “more like a knitting club”, which are more like a community.

  • “Patronage As An Asset Class” (Simon de la Rouviere): Thoughts on what a “patronage market” could look like. I’m not sure I believe assets need to be tied to physical objects, but I like the idea of building off the COST tax, i.e. people pay based on wanting to preserve future access to a thing (which could be the creator themselves, too!). Not dissimilar to using a counterfactual approach to valuing infrastructure (i.e. value = what would it cost us if this infrastructure didn’t exist), I think.

  • “The Rise of the Microgrant” (James Gallagher): I might just be in the thick of it, but it sure feels like more people are talking about microgrants than they were two years ago. I think ISAs (income share agreements) made “human capital” cool. Whatever the case, it’s been fun to watch, and this post is a solid overview of the ways that microgrants are cropping up in modern form.

  • “A Conspiracy To Kill IE6” (Chris Zacharias): The story of how one team at YouTube secretly dropped support for IE6 without asking anyone, thus nudging global traffic off of IE6 overall. I love stories about browser compatibility, and this one is particularly well-written, like a sci fi thriller!

  • “Journalism’s Dunbar number” (Damon Kiesow): An argument for local journalism focusing on relevance to its immediate community as a means of finding a viable business model. I don’t agree with everything in here, but the overall thesis parallels how I think about the value of patronage: finding high relevance among a smaller group of people, which is fundamentally different model from, say, crowdfunding or display advertising.


Relevant books that I’ve read this month.

  • Watch Me Play (T.L. Taylor): More ethnographies! This one is an ethnography of Twitch streamers. There are a ton of useful parallels to open source in here, particularly around the economics side. It was also cool to read about the author’s process, which seemed admirably thorough. She spent years visiting the Twitch offices; going to conferences and esports events; meeting with streamers, esports players, producers; and visiting streamers in their homes. While her writing is of an undeniably academic flavor (drink every time you read the word “labor”), there were times where I found that framing useful, supplying vocabulary for ideas I'd previously struggled to express.

  • To Engineer Is Human (Henry Petroski): A book about how failure is a necessary part of engineering that drives innovation. It’s a brave position to take, given that the author is writing about civil engineering, where “failure” means bridges collapsing and people dying. I feel like I kinda got the point after the first chapter or two, but it's a quick read, with interesting metaphors and case studies. I kept thinking about Don Norman’s Design of Everyday Things while reading this and wondering how the two would get along. Norman’s position is that UX failures aren’t the user’s fault, but the designer’s, whereas Petroski seems to be saying “Don’t blame the engineer either! Failure is just a part of how we improve technology”.

Loading more posts…