Files and Folders

I started writing this post talking about how I was using DEVONthink, and, as often happens when you write things down, I started thinking critically about how I interacted with the application. I took a folder full of screenshots, walked through some usage scenarios, and checked and double-checked what I was actually doing with the application. Then I exported everything to the Finder.

As of right now, I’m not using DEVONthink. I’ve gone back and forth over this for literally years. I get enthralled with the idea of building this perfect database, where every bit of information I need is at my fingertips, organized and indexed exactly as I want it. Then after a week or two of day to day use I realize that I’ve duplicated everything that I do with the Finder and a handful of other apps in DEVONthink, and decide to simplify.

One of the best things about DEVONthink is that it doesn’t modify your data, it simply organizes it and adds a layer of intelligence to help you manage it. The main selling point is it’s integrated “AI”, a parsing engine that looks for similarities between documents and can present you with connections between topics you may have missed. In this way, DEVONthink is more of an intelligent research assistant than a document management application like the Finder. Unfortunately, over the past several years of going back and forth, using it and not using it, I’ve never found a practical use for the AI.

I wrote earlier this week about how if you want to remember something you should write it down. Personally, I’ve found that I’m not good at this. I’m far more likely to find a way to record information using my Mac of iPhone than I am a notebook, simply because I’ve always got one of the two with me. I am however making a deliberate effort to give myself time to think clearly, stepping away from the computer and staring out the window for a while.

Computers excel at storing and searching information. Humans excel at making abstract connections between disparate bits of information. The best AI in the world can’t help me if I either don’t trust it, or if I don’t understand the connections it’s trying to make. My own brain is far better at making connections if I only give it the materials it needs. In other words, if I actually read and make notes on the information I’m saving. Using several “anything buckets” over the years I developed a bad habit of saving things after skimming through their contents, thinking that I would have it if I ever needed it. In practice though, instead of searching my own personal archive, I would almost always just search DuckDuckGo or Google again. My perfect database becomes a crypt of partially read web archives.

My entire job is managing information. What commands to type in where to get the desired result. Which buttons to click and what code to push to enable my team to get their work done. Every day the Internet is building and rebuilding itself, and my team does their part to help make information available. I even went to grad school for Human Computer Interaction, and learned only that the best way to manage information is “whatever works for you”. Sure enough, what worked for me in grad school was to have a top level folder named “ISU”, and a sub-folder underneath for every class I was in, and then a folder under each class for each assignment, as well as a folder for the videos of all the lectures. The organization was simple and easy to understand.

Again, when I looked through my DEVONthink system, I found that I had recreated everything that the Finder did. I had a database for each major topic or area of life, and folders and subfolders that further refined the topic till I reached the files. For example, my “Research” database contained an “Operating Systems” folder, that contained folders for “Linux”, “BSD”, “OS X”, and “Windows”. My Linux folder contained a folder named “Shared Internals”, and underneath that a folder named “Kernel”. Inside the Kernel folder were documents pertaining to the internals of the Linux kernel.

While I’ve read most of the documents in my database, too many of them I’ve only skimmed. What would be much more useful is a Zettelkasten. A Zettelkasten can be thought of as a Wiki with short articles. The point being that while I’ve been spending a lot of time organizing files, what I really want out of my computer is knowledge.

If you haven’t figured it out by now, I’m still working through all of this. I haven’t found the one true way to organize your data that I can recommend to everyone. What I learned in school still stands, how you organize your data remains up to you. Whatever works best for you is what you should do.

I think it’s good to have original source material on hand, but that source material is only useful if the information it contains is extracted and incorporated into a personal knowledge base. This has been my mistake for too long, to think that simply by saving and skimming over original source material I can increase my knowledge and effectiveness. Tools like Evernote and DEVONthink encourage this kind of digital hoarding by making it easy to save data, but the truth is that there is still no substitute for doing the hard work required to learn. You have to read, reflect, think it through, and write it down. Maybe on paper, maybe not, but without the intermediary step of synthesizing the information you’ve collected into your own personal system, it’s just more junk that needs to be cleaned up.