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Continuing with what I started yesterday with my post about Simplenote naming — and expanded on by Ian Hines, Dave Caolo, and Stephen Hackett — here is some more about how I name things on my Mac.

When it comes down to how people ‘file’ stuff on their computers I see three main methods people use to file: ((Most mix and match two of these methods.))

1. The Nesters: they create sub-folder upon sub-folder until they end up with stuff like this: Project A > Year > Month > Day > Hour > Minute > File. Ok not usually that extreme, but you know what I am getting at.
2. The Desktoppers: Everything is filed on the desktop for fear that one may ‘lose’ that file forever if it is moved elsewhere. ((I can’t be friends with you if this is how yo file.))
3. The Searchers: Just throw files in one massive folder and then use search methods to find the file later.

I doubt that most of us fit into just one of these categories — in fact most of you are probably hybrids of two of these options. I am a hybrid of 1 and 3. That represents a sweet spot for me, but no matter what, you really need to make sure you are properly naming files and that you aren’t a full 2.

I am a huge fan of Dropbox and instead of keeping a ton of files in just the main top level Dropbox folder I have a series of sub-folders. The main reason for these subfolders is so I can find what I need quickly in the iOS app for Dropbox. (This is doubly important when you have clients looking over your shoulder at your iPad when you are looking for the file. I like to pull up the relevant folder prior to the meeting.)

So inside my Dropbox folder I have a series of subfolders. These subfolders are classified for the various parts of my life (Work, Home, Blog and so on). So I have my office, my back up, my reference, my Simplenote and so on. Most folders residing at the first sub-level of the Dropbox folder are items that are in place for syncing only or strictly for other programs to interface with.

The real business happens inside the folder labeled: Inbox.

My inbox folder is where I keep 90% of all files I am currently working — the only stuff not in the folder are large files that would throw me over my Dropbox limit. Initially I just kept a ton of files in the folder, but as time wore on I realized that to find things quickly in iOS I really needed a few subfolders — but not too many.

I keep one subfolder in Inbox that is called ‘Projects’, inside of this folder I keep others that tie directly into OmniFocus projects that I currently have active. Thus the Inbox structure looks like this: Inbox > Projects > Project Name, where the ‘Project Name’ folder is linked into OmniFocus. I keep other files that are single action in nature in the Inbox folder itself (more specifically scans and the like).

This is as far as I take my subfolder routine. From here all files are named with a rather cryptic looking description — much like how I talked about naming Simplenote files.

TBR_P_2011_02_14_Name

The above is a representation of the basic structure I use for naming a file. What the above name tells me is that the project is TBR (designated always between 2-3 letters). The second piece, the P, tells me that the file category is a ‘Post’. I use a single letter to help designate a general category (P for post, O for outline, D for design). This way I can have two files with the same name, but different types:

1. TBR_P_2011_02_14_Pluto
2. TBR_O_2011_02_14_Pluto

Where the first would be a post with the name Pluto for the project TBR and the second would be an outline named Pluto for the project TBR. Basically I can run a search in Spotlight for: TBR + Pluto and get both files and know the difference between those files. Likewise I could also search TBR + O and see just outlines. This allows for very scannable file names, while keeping them easily searchable.

I do the same for all projects — I even label my website files this way when they are on the Mac.

To Each His Own

I always create a TextExpander snippet for file naming, this way I don’t waste time wondering what day it is and where the underscore key is (both happen more than I like to admit). What I know without a doubt is that this file naming system will not work for you. You need to come up with your own — I am sharing mine with you to help you see how I do it and perhaps you can steal portions of this to help your filing.

Underscores, Hyphens and Dates

I want to mention why I do two things in the above naming scheme that I haven’t touched on. Specifically why I use underscores over hyphens and why I use dates in the file name.

• I have found that underscores make the name much more readable to my eye than hyphens do. Both hyphens and underscores accomplish the needed separation between elements of the name, so there is no right or wrong. You can and should use whatever you like best. For me that is underscores to help me read the file names easier, for you it may be hyphens — just don’t use periods (you will regret that).
• I know a lot of people that don’t put dates in the file names and will rely on the built in date metadata to see when a file was created — personally I found out the hard way that those dates are incredibly unreliable. If you have stored your files on a communal server at any point then you know what I am talking about. Egnyte, the server we use at my office, messes with these dates like you would not believe and there has been several instances where I couldn’t tell when the file was made because of this. It is easy to attach the date if you use TextExpander and if you don’t use it — then at the very least attach a year and month (you can thank me later).

As Detailed as You Need

We need to borrow from Patrick Rhone’s philosophy of ‘enough’ here. Your file naming and folder structure should be nothing more detailed and nothing less obscure than what works for you. A good place to start (and where I would start now) would be with moving everything into one single folder and then naming the files with a very detailed name. From there play with the naming of the files and add back folders only as needed.

I recommend doing it this way because people tend to never remove folders if they start with many and will rarely add more information to file names if they start with abstract names. A big bucket forces good naming and good naming will reduce the amount of folders needed. Plain and simple.

The Desktop

Lastly, if you are a person that files everything on the desktop: stop and stop now. Again, you can thank me later on this one.