I have a folder in Dropbox with 380 files of notes, running lists, and piece of writing, ranging from finished posts, to running lists, to one-line note snippets. I have nearly 2600 bookmarks in Pinboard, and they’re all badly tagged. My life exists in various chunks of disparate data, largely living in the cloud, and it’s become a mess. Finding things, even with the great search tools in Pinboard and nvALT, is still a challenge. The point of a filing system is to be able to find things when you need them—fast. My system, or lack thereof, has failed me. And every piece of data I add is only making the problem worse. This is my fault, of course. Only a poor craftsman blames his tools. Part of how I got into this mess was first not defining just what belongs, or doesn’t belong, in these buckets of stuff. 

I had this problem once before, and my solution has been to live life in Plain Text (well, Markdown). I built a system around Merlin Mann’s txt system. Combined that with occasional use of Evernote for anything that required images or PDF files, and I was off to the races. My cardinal sin, however, was using nvALT as home for more than just “notes”. I used it to house my writing. When I first realized my nvALT was getting crowded, I set up a rule in Hazel to move anything tagged with #archive in the file name to its own folder. This worked, but I ran into a bug with nvALT when I changed a file name and Hazel moved it out, if I was editing another file name, it would switch the file I was renaming it with the one below it in the list, which only made my tenuous file organization even worse.

As for Pinboard, back when I started with Delicious for bookmarking, I was somewhat religious about tagging everything that ended up in my database. However, it’s so easy to pipe stuff into Pinboard—every Tweet I fave has its attached link saved, as well as everything I save in Instapaper—and so hard to go back in and tag things. I love Pinboard. It’s the best service in its class, as I discovered after trying to use Evernote to store bookmarks for research. However, it does not reward sloppy bookmarking, and a lot of the tools I used to load things into Pinboard were extremely sloppy.

It’s looking like the only solution is to start over again. Drop a bomb on my Notational Data folder and my Pinboard, clear out the years of cruft, and vow to be more disciplined as to what goes where. I don’t want to give up Pinboard, but I suspect my writing and notes workflows might need a revision. I’ve been experimenting with using Trello to track tasks and lists, and I can see it as a great way to offload a lot of the running lists of media and the like to check out into a more structured system. I also could shunt off my Writing to a dedicated space in iCloud and have that all live in Byword. Evernote can take over for quick capture, notes, and reference files.

The “Everything Bucket” app I’ve dreamed of for years isn’t going to work. I’ve tried nearly all the options over the past decade: Yojimbo, DEVONthink, MacJournal, and even Evernote. The way my mind works, and the lackadaisical way I tend to organize things make dumping all my data into one silo a bad idea. I need to make sure that I’m vigilant in policing what goes in, where, and how. I also need to make sure I clear out what’s no longer valuable. I doubt there will ever be an application that can organize my information for me without some intervention. The right tools, however, with the right mindset, will put me in a good place to keep up with what comes in.