When a new model gets released, I immediately point it to a giant folder filled with a ton of context and start asking really hard questions.1
And once I started using Claude Cowork I noticed that (unlike Claude Projects) there was no longer a file limit.
Hallelujah!
But unfortunately that didn’t mean I could just use bloated file and folder structures — LLMs still struggle with large numbers of files due to their limited context window.
And this problem is exacerbated by knowledge work because you’re constantly incorporating new information.
I’ve learned that LLMs and agents use a “brute force” approach to navigating large amounts of context. It can work, but it also will cost you a lot of tokens and can miss a lot of your critical information.
Thankfully there’s a solution, courtesy of Anthropic researcher Andrej Karpathy.2 Karpathy came up with a simple yet elegant approach to creating a self-improving “company brain” using folders, markdown files and Claude skills.
