June 2026

Your documentation is still in your Mum’s filing cabinet

It’s kind of wild when you stop and think about it.

Most documentation is arranged into files, folders and hierarchies. A document goes inside a folder inside another folder and on the surface it’s well tidy. The trouble is that knowledge rarely behaves that way.

A component accessibility decision can affect design, engineering, content and customer support. So where do you put the documentation for it? The more complex the subject, the more awkward that choice becomes.

The modern desktop was developed at Xerox PARC in the 1970s. Early graphical user interfaces borrowed heavily from physical office concepts like documents, folders and filing systems because they were familiar to office workers.

Fifty years later, we’re still using the same mental model. But how many people under 30 have even used a physical filing cabinet?

The filing cabinet we inherited

We rarely stop to consider how much of our digital world is built on this old office metaphor.

I once worked with a guy who saved all his files directly on his Mac desktop. He navigated spatially, placing documents into different zones on the screen and developing a muscle memory for where they were located. I’m not sure he even realised they were saved within a directory structure underneath the desktop folder.

I grew up with the idea of documents inside folders, and as a UX designer, I just expanded on it to create the information architectures of websites.

But imagine if we hadn’t been primed with this tree structure? Maybe more creative and spatial interfaces would have emerged instead.

People don’t browse documentation like librarians

There’s a theory called Information Foraging, which suggests that people follow clues rather than systematically exploring hierarchies.

Peter Pirolli and Stuart Card describe people as information foragers. This is such a rad term for people looking for stuff on the web. Like a badger foraging for small invertebrates, we humans look for signs that useful information might be nearby and constantly decide whether to continue the search.

This may help explain why documentation users often:

The information often exists, but people don’t instinctively find where it has been stored. It made sense to the person setting up the filing cabinet, but because it’s several drawers down, nestled in with the winter jumpers and hiking socks, it was never to be found. We are all familiar with that team’s Confluence wiki.

Knowledge doesn’t fit into one folder

Circling back to design systems, a component accessibility decision might go in any drawer of the cabinet:

But our folder structure forces us to pick one location. The moment we do that, every other route becomes harder.

Researchers have been discussing this limitation for decades. Work on Semantic File Systems in the early 1990s argued that information should be retrievable through attributes and meaning rather than physical location. People usually think about information in terms of topics and tasks, while traditional file systems organise information by location.

AI exposes the problem

Compare this to how AI navigates. Most modern AI retrieval systems don’t rely primarily on folder structures in the way traditional document repositories do.

A design token page can be retrieved because it mentions colour contrast, not because it lives inside:

Design System → Foundations → Accessibility → Colour

The more I work with AI systems, the more obvious it becomes that folders are a storage mechanism, not a knowledge architecture. AI is exposing a problem that humans have been working around for years.

From storage architecture to knowledge architecture

We live in a world of constant context switching. My neurodivergent brain moves continuously between browser tabs, applications, messages and my phone. In that environment, expecting people to remember the one ‘correct’ location for a document feels increasingly unrealistic.

Tree-based organisational structures are so deeply embedded in our tools and workflows that they are unlikely to disappear anytime soon. The more useful question is how we make information within those structures easier to find. Rather than relying on a single home for knowledge, we should make it discoverable from multiple directions.

Modern documentation benefits from multiple paths to the same information:

This idea always brings me back to Chase McCoy’s forward-thinking piece, Design systems as knowledge graphs where he argues that design systems are fundamentally collections of interconnected knowledge rather than sets of isolated assets, and that understanding the relationships between concepts is often more valuable than knowing where any individual piece of information is stored.

I’ve been using Obsidian for note-taking for the past couple of years, and one of its most powerful features is the way tags and links create a graph of relationships. Instead of forcing notes into a rigid hierarchy, it shows how ideas connect, overlap and intersect. That’s much closer to how knowledge actually works than any folder structure I’ve ever used.

I’ve started to wonder whether accessibility has been pointing us in this direction all along (smug face). One of the recurring themes in accessibility is that information should never depend on a single path. We don’t rely on colour alone, shape alone, or visual position alone to communicate meaning.

The same principle applies to documentation. Information becomes easier to discover when people can reach it through search, navigation, links, metadata and related content.

The same characteristics that help humans find information also help AI systems retrieve it:

The goal isn’t to find the perfect place to store information. It’s to make it easy to discover, whatever route someone takes to get there.

Closing the drawer

For years we’ve treated documentation like a filing cabinet. Put the thing in the right folder and give it a label.

But much as it pains me, people rarely wander through my carefully crafted hierarchy, admiring the taxonomy. They search, skim, follow links. And the second finding information feels like work, they’ve checked out and just asked someone.

Once AI has access to your documentation, it doesn’t care where you filed something. It finds information through meaning, context and relationships.

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.

If you have strong feelings about folders, filing cabinets or Your Mum, hit me on Bluesky