michael-dean-k/

Paul Graham’s idea of makers/managers is helpful when thinking about AI agents. The cost of being unreasonably productive is that all your time will go into management. I’ve heard people celebrate this, as if elevating above the work itself and only making high-leverage decisions based on taste is the place we want to be. Disagree. Without actually being in the weeds and making thousands of unbearably slow decisions, you won’t develop taste, and (probably) won’t be a great manager either. I guess the ideal (for me) is to be in maker mode as often as possible, and then let my synthetic managers come in to process my deep work. (Currently have a “proseOS” where I can riff 5k words into a daily note, and then agents come in to route my logs to different interfaces). Ideally, you build the manager once and forget about it. But realistically, a maker can find fun in making manager bots and management apps, and it’s quite easy to slip into a managerial goon loop. What I mean is, similar to masturbating with no intention of ever finishing (aka gooning), it’s very possible to make your own task manager app, and a writing app, and an idea Kanban linked to Obsidian, and why not a new personal website, and a 1,000 day calendar because you can, and seriously anything you can think of, and it’s very possible to just numb out over how unbelievable it is that code, markdown, and interface are now liquids that shape around your every intention, but actually, you never quite finish anything. PKM procrastination is timeless, except now it’s multiplied to new levels. The brute velocity of execution means you’re bound to make many little mistakes, which eventually compound into your own megamachine that traps you with endless bugs and feature ideas and system decay. This is all quite dramatic. I love Claude Code and insist everyone IRL and IFL try it. But now that it’s shockingly trivial to build your own personal software for free, I imagine there will be all sorts of unanticipated psychic costs. For one, it’s dangerous if building your own tools is equal to or more fun than the work the tools are for. I’m sure that wears off. But I generally think this all leads to both extremes: individuals who are unbelievable prolific, and individuals stuck in a goon loop who feel unbelievably prolific.

This essay tapped into a striking definition of timelessness. He doesn’t get there until halfway through though, and I found myself disagreeing with—or at least, questioning—a lot of his earlier points (I’ll come back to this). The main point is distilled into this: the best essays are “ineffective” because they reveal the timeless problems that each generation fails to synthesize. Timeless essays speak to the common foils in the human operating system: the blindspots of parents, the lies of institutions, the avoidance of mortality, the ineffability of relationships, the mundanities that are never captured in enough detail. These are different than “discovery” essays, like Darwin’s Origin of Species. The holy grail of an essay is surprise, and a timeless essay is not just sueprising for one generation, it’s surprising for every generation. And so timelessness, then, is a type of “breadth of applicability.”

PG also ventures into a familiar territory of “essay as a mode of thinking.” Where as in the past he used “the river” as his metaphor (2004), this time it’s a tree. You start from an origin, and then you explore many different branches in search of generality x novelty. What is a good starting question? He says a good one is “outrageous, counterintuitive, overambitious, and heterodox.” It doesn’t have to be a complete thesis, but some puzzling gap, and importantly something you care about. You won’t be able to stretch an origin question into cascading insight unless you have a unique angle into it. The origin doesn’t matter too much though, because it’s a recursive process, and you can eventually get to the best question in “a few hops.” I love how he emphasizes that you need to write to explore branches of a tree, and there are many dead ends; you realize how you are mistaken, incomplete, and inelegant (you go from vague to bad). Don’t get discouraged by these; finding your false assumptions is possibly the only way to really begin.

Despite loving his whole exploration of “mode,” I don’t think that means you have to neglect essay as “genre”; he says form/style don’t matter in “the best essay,” and I disagree, obviously. He has Darwin as the pinnacle example of an essay, and I’m really challenged by that (I definitely have to read it now). Is that an essay or a scientific paper, just captured in shortform non-fiction? He seems to imply that the essay is at its best a vehicle for discovery, as a mechanism to bring forth surprising, important, and useful ideas. From the creator of “make things people want,” this isn’t surprising. Even though a new theory of evolution had broad implications for society, I assume the paper itself is technical, intended for a scientific niche audience, which in my mind, makes it more like a scientific paper than an essay. An essay is something that is universal/general enough for the average person to read. An essay, I think, functions like an information transfer system between specialized facets of society; it’s about making your specific niche legible to all the other niches, and I don’t think that was the specific goal of Darwin's writing (even though it was inevitably understood by everyone, it wasn’t through the writing, but from the effects of the writing).

(Added: Another note on Graham’s notion of best as timelessness: he says that timeless esasys are the perennial insights that each generation can’t absob. This implies that the insight is never enough: even if you know something, there is often a lack of wisdom in applying it to your own circumstance. And so really, these unteachable lessons are ones that can only be obtained through personal experience. Does this point to the fact that all essays need to be personal? Maybe bland insights can’t be digested by a reader, but if they are integrated to vivid personal experience, experience vicariously, then might this actually be the best medium to transfer wisdom?)

AI summary of one of my threads:

"Paul Graham founded Y Combinator in 2005 and hand-picked Sam Altman—a founder from YC’s very first batch—as his successor, creating a mentor-protégé lineage that symbolizes the essential partnership between ideas and action in technology. Graham, the essayist, codified startup wisdom into executable blueprints, democratizing knowledge that had been locked in VC oral tradition and proving that clear writing is the mechanism of clear thinking; Altman, the accelerator, absorbed that intellectual operating system and is now applying its core logic—“startup = growth,” “build things people want”—to the ultimate technological lever: intelligence itself. Their relationship frames Graham as perhaps the most consequential pragmatic philosopher of the 21st century: not a thinker who wrote to be understood, but one who wrote to be executed, with Altman and the AI revolution serving as empirical validation of his text. Graham wrote the blueprint for the current world; Altman is using it to build the next one."