Bring back the old-school way of managing computer folders and documents yourself!

One of my pet peeves in software is the black-box application that calmly sucks in all of your files and does everything for you, until the day you want to swich apps. This is the iTunes model, followed by many other products.

I am of the opinion that rather than allowing an application to shuffle your life randomly, why not do it the old fashioned way and move your documents into folders of your choosing?

This article discusses some of the advantages of old-school folder management and gives a few hints along the way.

Why bother?

By creating your own well thought out folder structure, you gain the following advantages:

• You can find something fairly easily without needing to launch the special app.
• You can copy reasonable subsets of your document sets to friends or for backups.
• Someone else can find something without needing the special app.
• You can place files in a common network drive that others can see, from PC, Linux, or Mac.
• You do not lose all of the metadata about your files if the document management app ceases to exist.

People have been managing their documents this way for decades, so this is not anything new. What is new, however, is that folks don’t necessarily see what flexibility they give up when they allow the computer to squirrel things away on their behalf.

What kind of folders?

In short, pick some categories of documents that you will be filing, and optionally pick a timeframe which to partition the folders. This mirrors what we do with paper folders, doesn’t it? We create dozens of manila folders with tabs, and optionally create subsets of these files by date (e.g. Receipts, 2009).

One key difference helps us: Computer folders enjoy one feature that their physical counterparts lack—they can be nested several layers deep.

A few examples are probably in order…

I like to keep several kinds of scanned documents relating to day to day home paperwork. Over time, it has become clear that I scan lots of receipts, health insurance papers, banking papers, bills, and … everything else.

As such, I created the following top-level folders: Banking, Bills, Health Insurance, Receipts, and Miscellaneous.

Over time, they start to get stuffed to the gills with things, especially the Bills and the Receipts folders. My answer to this was to split them out by date. Within each category folder I have subfolders by date. This is because some categories need lots of years, while others might not need to be broken down by date at all.

Digital photos are a different creature: I feel that the date of the photo is the most important piece of information, and subject matter is secondary. For this reason, I store my photos in a series of top-level folders labeled with the years.

With photos I have a three-level system: Year, Month, and Subject. For example, within the Photos folder there is a 2009 folder. That contains a 2009-02 folder, and that one contains a folder called Cats. There are many ways to arrange these, I have chosen this approach.

I like iPhoto as much as anyone, and I use it for my photos. The difference is that, for me, iPhoto only holds a copy of each photo—the original photos are all stored on a NAS using the file structure I describe above.

Put a little thought into it and come up with a system that works for you.

Closing thoughts

We are looking for ease of use here, as well as avoiding lock-in to some proprietary app. We also want it to be easy to back up specific bits of the data and share specific bits.

By looking at my example above, you can see how easy it would be to find a bill from 2009. By following a specific naming convention, you can see that each document is fairly descriptive as well. You don’t need DEVONthink or its brethren to tell you how to find the Allstate bill from June of 2009. In addition, the folder names are now easily searchable by my operating system, as are the filenames.

This might create extra work for you in the beginning, but do you really want to be at the mercy of someone else’s application?

Oh, and about making those folders? There are applications out there that can generate a bunch of folders for you following your own chosen rules. One I use is The Big Mean Folder Machine.  I wouldn’t want to depend on an automatic system for daily use, but as a one-time jump start, tools like this can work wonders.

Don’t forget to back up your files!