Why Your Documentation Is Still Stuck in Your Mum's Filing Cabinet

Documentation is still in your Mum's filing cabinet

Why Your Documentation Is Still Stuck in Your Mum's Filing Cabinet

I argue that our reliance on folder hierarchies is an outdated metaphor from the 1970s that fails how humans actually forage for information. Instead of forcing knowledge into single locations, we should build systems with multiple discovery paths using search, tags, and links. This approach not only helps people find answers faster but also aligns perfectly with how AI retrieves meaning through context and relationships rather than physical storage locations.

The future of documentation isn't a bigger filing cabinet with better labels. It's a connected body of knowledge that can be discovered from multiple directions by both humans and machines.
  1. BLKNSLVR

    This is one of the 'killer apps' of AI.

    My workplace has a number of multi-hundred page "User Guide" documents that are an absolute chore to read through for anything actually useful to the scenario-of-the-moment because they're so granularly detailed that, even if you find the right section, it might be difficult to relate it to the scenario because there's so much detail that the context gets lost.

    If we could get them ingested as an LLM context, and then make a customer-accessible interface, it would be a great value-add for Customers as well as Employees.

  2. MomsAVoxell

    I worked on an educational title in the 80's which taught people what computers were, and how to use them. It focused on the basics - what is memory, how does a computer use it, what are files and folders.

    I had a few thousand happy customers and would hear from folks whose computing competence had been lifted by the titles I worked on .. that they finally 'got it' when the difference between memory, storage, files and folders was finally clear to them.

    It is incredibly frustrating to realize that these apps I wrote in the 80's are still entirely relevant today. Too many times I've been in someones business office, and observed some new generation folks not quite understanding where things are stored, how they're stored, why and when to the use ~/Documents and ~/Downloads and ~/Desktop, and so on. Some folks just put everything on ~/Desktop and wonder why they can't find anything. Some folks thoroughly enjoy being coached through creating their own organization systems, for the first time, at the filesystem.

    For the past 30 years I've been printing to PDF every interesting web page I've ever read. I now have a collection of 80,000+ .PDF files, in one folder, a huge collection of my personal knowledge and interests. It is immensely rewarding to "ls -l | grep <some interesting subject>" and get a sorted list .. to see also how I have revisited certain subjects over time ..

    And now I'm faced with the issue that I just really want to data-mine this archive, so .. of course […]

  3. euroderf

    Trees can point upward too. There's incoming references. There's metadata tags/facets.

    And there's multitrees, that might or might not help.

    https://interactivity.ucsd.edu/articles/In_Process/MultiTree...

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2026-07-11