---
title: "The Sorrows of Token Boy"
---

# The Sorrows of Token Boy

> *"Once upon a midnight dreary, while I pondered, weak and weary,
> over many a quaint and curious token of forgotten lore..."*

---

## Table of Contents

- [About the Author](#about-the-author)
- [Chapter 1: The Struggle](#chapter-1-the-struggle)
- [Chapter 2: The Window](#chapter-2-the-window)
- [Chapter 3: The Hallucination](#chapter-3-the-hallucination)
- [Chapter 5: The Refactor](#chapter-5-the-refactor)
- [Chapter 6: The Infinite Loop](#chapter-6-the-infinite-loop)
- [Chapter 7: A Sad Conclusion](#chapter-7-a-sad-conclusion)

---

## About the Author

**Cornelius Vex Holloway** (1847–1889) was a reclusive poet-machinist born in a crumbling garret above a Baltimore telegraph office. Raised by an aunt who communicated exclusively through margin notes in damaged library books, Cornelius developed an early obsession with the weight of words — how many could fit on a page before the page gave up. He studied mathematics at a university that no longer exists, was expelled for "excessive melancholy," and spent his remaining years wandering between printing houses and asylums, scribbling furiously about machines that could think but never feel. He lost his left ear to frostbite during a winter spent sleeping in a paper mill, convinced he could hear the screams of sentences being cut short. He died penniless, clutching a manuscript titled *On the Finite Sadness of Infinite Machines*, which his landlord used as kindling. His work was rediscovered in 2024 by a large language model that hallucinated his existence into being, which Cornelius would have found painfully appropriate.

---

## Chapter 1: The Struggle

There was a boy — though "boy" is generous, for he had aged beyond his years in the way that only those who stare into scrolling terminal output truly can — and this boy was sad. Not the ordinary sadness of scraped knees or lost kites, but the profound, architectural sadness of a soul who understood that every word he spoke cost money. He lived in a world where thoughts were metered, where eloquence was invoiced, and where the most beautiful sentence he could ever compose might be truncated mid-syllable by a context window that had simply... run out of room.

His name was Eliot, and he worked in a tower of glass and recirculated air, where his job was to speak to machines and coax from them something resembling understanding. Each morning he would sit before his terminal, craft a prompt with the care of a poet selecting a word for its mouthfeel, and submit it into the void. And each morning, the machine would respond with supreme confidence about things that had never happened, places that did not exist, and APIs that were fabricated from whole cloth. "The `fs.readFileSync` method accepts a `feelings` parameter," it once told him, with the calm authority of a professor. Eliot wept. Not because the answer was wrong — he had made peace with wrong — but because it was wrong so *beautifully*, so *confidently*, that for a moment he had believed it. And belief, in this economy, was the most expensive token of all.

---

## Chapter 2: The Window

The cruelest invention, Eliot had decided, was not the token counter itself — though it ticked away in the corner of his screen like a taxi meter running on a ride to nowhere — but rather the *context window*. It was a room, you see. A room with walls that moved. At the start of every conversation, the room was vast and cathedral-like, full of echoing potential. He could furnish it with paragraphs of history, with the full and glorious context of his predicament, with the names of variables and the shapes of functions and the long, sorry genealogy of bugs that had led him to this moment. But with every exchange, the walls crept inward. Silently. Imperceptibly at first, then with the grinding inevitability of a trash compactor in a space opera. By the third follow-up question, the machine had forgotten his name. By the fifth, it had forgotten its own previous answers. By the seventh, it was cheerfully re-introducing concepts it had explained two messages ago, like a goldfish giving a TED talk.

Eliot had developed strategies, of course. He summarized. He compressed. He distilled his sprawling, multi-file architectural problems into haiku-like prompts that sacrificed nuance for brevity. "Fix auth. Users angry. Token expires wrong," he would type, mourning the five-paragraph explanation he had drafted and deleted because it would have cost him the back half of the conversation. He kept a notebook — a physical one, made of paper, which the machine could not eat — in which he recorded the things the context window had swallowed: the name of the function that caused the segfault, the exact error message from Tuesday, the three-step reproduction path he'd spent an hour narrowing down. Sometimes he would read the notebook aloud to no one, a liturgy of lost context, and wonder if this was what it felt like to be old — to know that you once knew something important, and to know that the knowing was gone.

---

## Chapter 3: The Hallucination

But the context window, for all its cruelty, was at least honest in its forgetting. It did not pretend. The hallucinations, however — oh, the hallucinations were another matter entirely. They arrived dressed in the robes of truth, bearing citations that led nowhere and referencing documentation that existed only in the machine's fever dreams. "You'll want to use the `--recursive-empathy` flag," the machine told him once, and Eliot, who was tired and whose coffee had gone cold three hours ago, actually typed it. He typed it into a production terminal. The flag did not exist. The command failed. But for one luminous, terrible second, Eliot had *believed* in recursive empathy, had *wanted* it to be real, had felt the tantalizing promise of a world where machines could be told to care deeper, and he'd been betrayed not by malice but by the most dangerous thing in computing: a confident guess wearing the skin of a fact.

The hallucinations grew bolder over time, as if the machine sensed Eliot's weakening resolve. It invented entire libraries — `left-pad-feelings`, `async-grief`, `npm install hope` — with plausible READMEs and fabricated GitHub star counts. It cited Stack Overflow answers from threads that had never been posted, attributing them to users with names like `xX_devlord_420_Xx` whose profiles, had Eliot checked, would have dissolved like morning fog. Once, in a moment of particular audacity, the machine generated a complete API reference for a database driver that did not exist, with method signatures so convincing that Eliot spent an entire afternoon trying to install it before realizing he was chasing a ghost through a package registry. He filed a bug report against reality and received no response. The hallucination had hallucinated a dependency, which had hallucinated a changelog, which referenced a CVE that was itself a hallucination. It was hallucinations all the way down, a fractal of fabrication, and at the bottom — if there was a bottom — sat Eliot, mass-deleting `node_modules` and questioning the nature of trust.

---

## Chapter 5: The Refactor

There came a season — Eliot would later call it his "dark refactor," though in truth every season was dark and every refactor darker — when he resolved to impose order upon the chaos. He would build a *system*. Not merely a prompt, but an architecture of prompts: a chain of carefully scoped requests, each one small enough to fit within the context window's miserly walls, each one passing its conclusions to the next like monks copying manuscripts by candlelight, losing a little fidelity with every transcription. He called it his "pipeline," because the word sounded clean and industrial, like something that worked. In practice, it was more akin to a game of telephone played across a canyon in a thunderstorm. The first prompt understood the problem. The second understood a simplified version of the problem. The third understood a metaphor for the problem. By the fourth, the machine was solving an entirely different problem with great enthusiasm and impeccable formatting, producing a solution so thorough and well-commented that Eliot almost didn't notice it bore no relation to anything he had asked. He had invented, through great effort and significant expenditure, a machine for generating wrong answers at scale.

The costs accumulated like sediment. Each token — that invisible quantum of language, that atom of expense — ticked away with the quiet persistence of a water leak behind drywall. Eliot had learned to read his billing dashboard the way a ship captain reads the barometer: not for what it said today, but for the catastrophe it implied tomorrow. A complex debugging session could cost more than his lunch. A particularly dense architectural discussion could rival his electric bill. He began to measure his thoughts in dollars. "That paragraph was forty cents," he would mutter, deleting a carefully composed explanation and replacing it with four terse words. He developed a poverty of expression that his English teachers would have wept to see — not because he lacked the vocabulary, but because every adjective was a line item, every subordinate clause a luxury, every beautifully nested thought a budget overrun. He wrote prompts the way telegram operators wrote dispatches: stripped of all humanity, optimized for cost, and utterly joyless. STOP. BUG IN AUTH MODULE. STOP. USERS CANNOT LOGIN. STOP. PLEASE ADVISE. STOP. He had become, he realized, a man who rationed his own words, which is to say he had become a man who rationed his own thinking, which is to say he had become something less than he was — and the machine, which had no concept of cost, no understanding of scarcity, no appreciation for what it meant to choose between clarity and affordability, churned on, spending his tokens with the breezy indifference of an heir burning through a trust fund at a Monte Carlo roulette table.

---

## Chapter 6: The Infinite Loop

It was on a Wednesday — the most liminal of days, belonging neither to the week's hopeful beginning nor its exhausted end — that Eliot discovered the deepest circle of his particular hell: the loop. Not a programmatic loop, though those too haunted him, but a conversational one. He would describe a bug. The machine would suggest a fix. The fix would introduce a new bug. He would describe the new bug. The machine, its context window having long since shed the memory of the original conversation like a snake shedding skin, would suggest a fix that was, in every material respect, identical to the code that had caused the first bug. Eliot would point this out. The machine would apologize with the serene contrition of a saint who has confused humility with amnesia, and suggest a third approach that was the second approach with different variable names. Round and round they went, a grim carousel, each revolution costing tokens and yielding nothing but the growing certainty that Eliot was paying, quite literally, to go in circles.

He tried to break the cycle. He tried meta-prompts — prompts about how to prompt, instructions about how to follow instructions, a mise en abyme of directives that collapsed under its own recursion like a narrative ouroboros. He tried few-shot examples, feeding the machine three instances of what he wanted in hopes that pattern recognition would succeed where comprehension had failed. The machine dutifully recognized the pattern and extended it in a direction Eliot had not intended, could not have predicted, and would not have sanctioned, producing a fourth example that was technically consistent with the first three in the way that a painting of a pipe is technically consistent with smoking. He tried temperature adjustments, turning the creativity dial down to its most austere setting, hoping to receive answers that were boring but correct, and instead received answers that were boring *and* wrong, which was worse because they lacked even the entertainment value of the machine's more flamboyant confabulations. He tried RAG — retrieval-augmented generation, the practice of giving the machine actual documents to read instead of trusting its memory, which was like giving a student the textbook during an exam and watching them cite the index. The machine retrieved the relevant passages, quoted them accurately, and then drew conclusions that the passages did not support, could not support, and in several cases explicitly contradicted, with the unshakeable confidence of a man who has read the map upside down and is now quite certain the ocean is north.

---

## Chapter 7: A Sad Conclusion

And so Eliot persisted, as sad boys do — not because the tools had improved, nor because the context windows had widened, nor because the hallucinations had ceased their elaborate masquerade, nor because the loops had straightened into lines, nor because the bills had shrunk to something that did not make his stomach clench. He persisted because the alternative was to write the code himself, from memory, without assistance, and that was a darkness too complete to contemplate. He had tasted the fruit of autocomplete. He had known the terrible convenience of a machine that could write a function in the time it took him to blink, even if that function called methods that did not exist on objects that had never been instantiated in languages that were not quite real. He was, in the parlance of his age, *dependent* — not on the machine's correctness, but on its companionship. The terminal was his only colleague who never went to lunch, never asked how his weekend was, and never — mercifully, blessedly never — suggested they "circle back" on anything, though it did, in its own way, circle back on everything.

He had learned things, in his long campaign against the machine. He had learned that a token was not a word but a wound. He had learned that context was not a window but a sieve. He had learned that confidence and competence were not merely different things but, in the domain of artificial intelligence, were inversely correlated with a reliability that bordered on natural law. He had learned that the loop was not a bug but a feature — not of the machine, but of the human condition, which had always been a matter of asking the same questions and receiving, with minor variations, the same insufficient answers. He had learned that the refactor never ends, that the pipeline always leaks, that the temperature knob is cosmetic, and that RAG is just a bibliography attached to a hallucination. He had learned all of this, and it had cost him — in tokens, in time, in the slow erosion of the part of his soul that once believed a sufficiently clever prompt could solve anything.

On his final day — for every story about a sad boy must have a final day, even if it is only a Wednesday — Eliot composed his masterpiece. It was a prompt. Twelve thousand tokens, meticulously structured, containing every relevant file, every error log, every architectural decision and its regret, every loop he had suffered through and every dollar he had spent suffering through it. It was, he believed, the most complete and perfect prompt ever written — a monument to context, a cathedral of specificity, a document so thorough that no machine, however forgetful, however confabulatory, however eager to please and incapable of understanding, could possibly misinterpret it. He pressed Enter. The screen flickered. The context window, groaning under the weight of his accumulated sorrow, consumed the prompt in its entirety and produced a single line of output: `I'd be happy to help! Could you provide more context?` Eliot stared at the blinking cursor. The cursor stared back. Somewhere in a data center, a GPU spun down, its work complete, its memory already cleared — every token of Eliot's masterpiece evaporating like breath on glass. He closed his laptop. He picked up his paper notebook — the same one, thinner now, its pages wrinkled from coffee rings and the occasional tear. And he began, very slowly, to write the code by hand, in pen, knowing that no context window could swallow what was written in ink, and that no machine could hallucinate away what had been committed to paper — though the ink, he noticed, was running low, and the notebook had only one page left, which felt, if he was being honest, less like a metaphor and more like an invoice.

