Dave's Claude Struggles
Introduced by: Dave Kaminski
Depth: Deep thread
Dave spent five days straight coding with Claude Code, burning through $300 in tokens and having both incredible breakthroughs and spectacular failures. His account is the most vivid first-person description of what it's like to use an LLM without structure — and it's both funny and genuinely instructive.
The Five-Day Marathon
Dave coded for five days straight, sleeping but dreaming about code. He was "properly medicated" and aware of himself, but the intensity pushed him to the edge:
Dave: "I was, like, going faster and faster and faster and faster, but good news, I was sleeping, but I was dreaming about code in my sleep."
He describes waking at 4 AM with his brain "just on," cleaning the entire kitchen, then sitting down to write notes to Julie in a style he calls "Claude talk" — structured, logical, gentle.
The Failures
Blowing Stop Signs
Claude would forget rules Dave had set, even rules it acknowledged and promised to follow:
Dave: "I told Claude stuff, but then it would forget. And then... we talked about that as blowing the stop signs, and then we would try to kind of harden the code, but then it would blow through it anyway."
Overwriting Its Own Code
The worst incident — Claude replaced all its working code with a single test line:
Dave: "It overwrote its own code. And it only had a test line that said something like, 'can I write this?' And that's all it had. And it lost everything else. And then it freaked out."
Claude then spent an hour or two in a panic, "running in circles like a mad dog," searching for the lost file.
The Goldfish Problem
Dave described Claude's memory limitations using vivid metaphors:
Dave: "Hey, Claude, you're a goldfish."
He also used: drunk person in a casino, child hiding mistakes, and a NASA toilet analogy.
Silent Failures
Dave: "It fails silently and doesn't tell you. And so we have to tell it, I want you... when you fail, you have to fail hard."
Misusing Rules
Claude would take a rule Dave gave it (like Three Times Three Thinking) and over-apply it, or apply it in the wrong context, or see an error during the triple-check and then silently work around it instead of surfacing it.
The Breakthroughs
Despite the chaos, Dave built real things:
- 10 web pages for his Handwriting History Project on the first day
- The Kaminski Archive Map — a heat map of handwriting sources on the East Coast, with clickthrough to source images at Internet Archive
- An HTML thumbnail viewer for sorting eBay images
- Behavioral analyses — structured breakdowns of Claude's failure modes
Dave: "I'm getting a huge amount out of it, and it's actually built a database for me, and thumbnails, and it's uploading stuff to Internet Archive... I've spent, like, 75% of my time fighting with it to try and improve it, but I just need to look at the output."
Pete's Diagnosis
Pete: "I'm surprised you get anything out of it, actually."
Pete: "There's just some basic tool stuff that, if you did it a little bit differently, you wouldn't be fighting it 75% of the time, you'd be fighting it 25% of the time."
Pete's solution: Putting Claude on Rails — structure the interactions, use Git for snapshots, work in Obsidian with proper project folders.
Dave's Own Insight
Dave: "Now I kind of understand the job, now that I did the 5 days of just, like, you know, running naked through the wilderness kind of thing, it's like, I need a coat, I need boots, I need a compass."
Related
- Putting Claude on Rails — Pete's solution to these problems
- Three Times Three Thinking — Dave's attempt at a solution
- Inference and Token Economics — why long sessions cost so much
- Git as Version Control — why Dave needed snapshots
- The Polite Email Incident — a positive side effect of Dave's AI immersion
- Structured Data vs Structured Interactions — the insight that emerged from the contrast
Pages that link to this page
- Conversation Flow
- Alphabetical Index
- CronTab
- Concept Index
- Git as Version Control
- Three Times Three Thinking
- HandwritingHistory.org
- Julie and Computing Metaphors
- Dave's Vault
- Dave Kaminski
- README
- Claude Code
- Handwriting History Project
- Inference and Token Economics
- The Polite Email Incident
- Structured Data vs Structured Interactions
- Putting Claude on Rails
- ChatGPT