Lukas Mathis recently wrote a response to a proposed interface redesign for the iPhone from Bruce Tognazzini, who basically created Apple’s original Human Interface Guideline. You don’t have to read the whole thing if you don’t want to, since most of it is not specific to my entry. The section titled, "Hierarchies Are Often Problematic," is a good explanation of why I don't bother with more than minimal categorizing and filing anymore.
In just my Documents folder I've got about 500 items, many of them subfolders. I have saved documents on various different subjects, which are sometimes cross-references to yet other documents. Some of these are articles, text files, or PDFs downloaded from various internet sites, but at about half of that mess is self-generated content, some of it stuff created on my first computer.
If I relied on a hierarchy to find things, I'd either have to make up my own category system — something like a personal Dewey Decimal System — to reliably and quickly find what I’m looking for, or I'd spend several minutes at the very least trying to get to a particular file. And I’d still probably fail to find it a lot of the time. I used to spend hours categorizing things, making nested folders like Japan > Swords > Smiths > Galleries > etc. It took too much effort and time to maintain, and some things don’t fit nicely into categories.
I've quit doing that and have been using OS X’s Spotlight and keywords for the last few years. I don’t think I’ve used the Finder to look for anything in at least a year. Basic navigation from one folder to another when I already know where things are stored, yes, but I haven’t poked through the system to find anything in those old hierarchical folder nests I made prior to having a decent search system available.
Browsing is better for some things, so I do still make bundles of items in categorized folders, but I don’t spend anywhere near the amount of time on that as I used to because sub-categorization is mostly a waste of time. I use search and keywords to get me in the ballpark, and browsing to locate the file I was looking for.
Particularly with music, there are way too many files for me to want to screw around with categorizing, nesting, and filing things, which is why I don't even bother with the file structure and simply use iTunes as a front-end for searching and categorizing.
There are almost 4,000 music files in my library, representing about 350 artists. It's totally not worth my time to organize that. Tasks like sorting and categorization are exactly what computers were invented for, which is why I let the computer do the work instead of spending tens of hours on it myself. Any changes I make in artist, album, or song title are updated in the file structure, so if I want to organize things, all I have to do is clean up my iTunes tags. Even with those tools for categorization I've had to spend some time putting in tags and labels that are meaningful to me, but that represents much less time than doing all of it by hand.
As we accumulate more and more information on our computer systems, effective interfaces become even more necessary. Way back in the early days of the Internet, I realized that search was going to be a massive problem. And it was. The reason Google is now well on the way to becoming a tech behemoth is because sorting through the incredible amount of information on the Internet to find the few bits you’re looking for is the single most difficult and important task everyone needs to have done.
Our home systems will obviously never become as large as a worldwide network, but most users already are coming up against the limits of their capability or inclination to organize the information they do have. I reached my limit with self-organization years ago, which is why I had to find more effective ways of doing things. Creating better, more intuitive and effective tools for search and organization will continue to be a very important task for software engineers for a long time to come.