Personal files are a constant mess, or a struggle against this state. Same for me. A while ago, I decided to use my coding skills to automate some of the organizing work. It worked so-so. Here is what I learned.

Muscle Memory Trumps Everything

I built myself a little shortcut to create a project folder (when doing something new, my first step is usually to give it its own folder where everything lives): It would not only create the folder, but name it properly, with a prefacing numeric iterator. It would also create a README.md file - a convention programmers often use to give some general information about a project - as well as designated subdirectories for inspiration, experiments, etc.

It works quite well, technically. However, I never really started using it. My usual process for creating folders was just to ingrained (right click > create or mkdir). Maybe the solution would be to overwrite the default commands, but that’s hard. Oh well.

In any case, do not underestimate the strength of muscle memory with stuff like this. I literally forgot how my new shortcut worked after a while, because I didn’t even think about using it for too long.

Processes Over Tools

Another thing I built was a small script which went through all existing project folders, again inserting a README.md - this time including automatically generated information like an overview of existing subdirectories, first and last edit time and so on. The idea was that this skeleton would motivate me to touch old projects again, sort them, continue them. And again, worked well technically. And I did (and do) use it!

But only after several failed attempts to establish some kind of system of when, where and how I would actually work with these files and their projects. At this point, I both have a recurring daily habit of editing at least one of these READMEs, as well as a specific to do to revisit every single old folder, as well as another habit to check whether I am actually diligently doing the aforementioned thing. It works, slowly.

The point is neither the script nor the system here, the point is that the relevance of the habit design dwarfs the relevance of how well the whole thing works technically. I am pretty sure the habit system could work without preexisting READMEs. They mostly worked as an accusing reminder that I still don’t have a system to revisit all projects in the meantime.