Trying to make old files useful agian

Hey MPU,

I’ve been thinking a lot about a file and knowledge management problem that keeps showing up in my own work.

The files are there. The notes are there. The old screenshots, specs, QA notes, spreadsheets, bits of code, and half-finished ideas are all somewhere on my device. The problem is that they mostly just pile up.
When I want to use something from one part of my work in another, I end up searching again. Sometimes I can’t find it, so I make the same thing again from scratch.

Saving things is easy. Creating more things has gotten easier. Getting old work back into use is where my system starts to fall apart.

In Obsidian, this is exactly why properties feel useful. A note can have a project, status, topic, people, and whatever else matters. With Bases, those properties can become different views of the same notes. The note does not have to live in only one mental folder.

That is the part I keep wanting for files. I want to give files properties that explain the context they carry and my relationship to them: why I saved this file, where it came from, which project or decision it belongs to, whether I still need to act on it, and whether it is source mental, evidence, reference, or a finished output.

Finder can show a lot of system metadata, but adding my own properties is limited. In practice, if I want my own layer on top of files, I mostly end up stretching tags too far. Tags are useful, but they do not explain enough on their own.

macOS smart folders point in the right direction. Files can stay where they are, and a saved view can update around them. The problem is that creating and maintaining those views by hand is too much work for the way I actually think.
The moment I want something like “screenshots I captured this month” or “files related to the next launch that still need cleanup”, I’m back to building rules instead of describing the work.

So I started building a small macOS file manager app around that gap.

Right now, the app has two early pieces: property-based views that feel a bit like smart folders, and a way to create those views in natural language. I can describe a file view in plain English and turn it into a reusable collection.


The next thing I am thinking about is chat and agents. I don’t want to manage every property by hand. The app should be able to help assign and update properties, suggest useful collections, and let me keep working inside the context of a collection: summarize the files, ask questions across them, clean up names, or repeat the same file operation later.

I will probably come back here from time to time and show what I’m building. If you have built your own file or knowledge system, I would love to hear where yours breaks down, whether tags or smart folders have stuck for you, and what would make an app like this feel worth trusting.

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Hey, thanks for sharing. It’s a problem worth tilting at. The agent that expands the searchable surface area of the files, and builds a graph between that data to help your index, seems most useful to me.

Thanks for finding it useful just from the pitch. Yeah, one of my goals is for properties to accumulate into a graph over time, and then have a graph view where you can discover new connections.

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Where are the “properties” stored? Extended attributes? I’ve seen systems like this in the past – I think Ironic Software had an app that did this. The risk from the user perspective is access to properties / metadata when the developer stops support, Apple OSs move on, and the user is left behind.

Katie

Hey Katie, that’s great point.
Properties are stored locally, not server.

I have a few formats in mind. SQLite is easy for the app and agents to work with, but not great for users to inspect directly. Plain JSON sidecars are human-readable and portable, but can get messy with lots of files.

Open to other ideas if anyone’s seen a better pattern.