There is no “organize” button on the computer. There is no “tidy up” menu that neatly puts all your files and folders away in a manner both logical and simple. When making the decision to clean up your digital house you have to tackle it in the same way you do your real home. Methodically.

And just like the process of organizing your physical home, organizing your digital house has its own set of pros and cons that are not always that different from the ones you experience when tackling a particularly cluttered room.

CON: If you are the type of person who gets overwhelmed, be prepared to feel overwhelmed. Chances are you have kept a few small things well organized, a few more loosely organized, and the rest are in very generic folders and scattered about all over the place. You may have duplicates, triplicates, or even more of the same file. (I’m not counting back ups.) You may have vacation photos from just one trip scattered about in three different places. It’s the same thing as having your clothes in three different rooms. How are you supposed to go through them when you don’t even have them all together?

Unlike the KonMari method which tells you to save organization for last, I think you have to organize your digital clean up as you go at least to a certain degree. That doesn’t mean it has to be your end-all style of organizing, but you need a loose system. For example, I have a folder labeled “Funnies and Quotes” where I dumped all the comic panels and memes I’d saved. This kept those in one place and one place I could find easily. Once they were gathered up from all over, I furthered my organization by creating sub-folders for types of comics and memes, making it easier to always find the one I want.

In the same way the KonMari method tells you to gather all items of one category before you start going through them, use a loose organizing system of folders to gather your files. You can fine tune your organization later.

PRO: You might be feeling overwhelmed, but you can very easily break up the task of organizing your digital life into dozens of much smaller, much more achievable goals. Some of my goals include “organizing Dropbox” and “finish going through my Watch Laters on YouTube”. Some of the bigger goals like cleaning out two very, very messy email accounts might look like “go through 50 messages a week and decide to archive or delete”. (Those were 50 messages I’d left sitting around in my email, mind you, I didn’t get to count anything new showing up that week.) This makes for quite the long list, but I knew when starting this project it would take me at least a couple of years of work to achieve if I wasn’t going to set aside large amounts of time every week to do nothing but sort digital files.

Here’s a tip: always end the week more organized than you began it. Did you receive 60 emails? Go through 90 of them. Spend 10 minutes sorting out your photo files by year or event instead of 10 minutes surfing the same Facebook posts you saw 30 minutes ago. This might feel small, and it is, but it’s a wonderful feeling to end every week just a little bit more organized than you began it.

Another tip (especially for those who get bored quickly with these sorts of tasks) having a list of all the sorts of organizing you plan to do makes it easy to bounce from task to task.

CON: Bouncing from task to task means it might be a much longer time before you can start marking things off your list, even though you’ve set goals that are much smaller than the end goal. Remember the main goal though? Always make progress. End every week at least slightly more organized than you began it. And on rough weeks if that means you deleted 10 files you don’t remember why you kept and nothing else… that’s progress. Do more on the good weeks and less on the bad. Burn out is the only enemy.

PRO: The flipside is that although it may take you a very long time to start marking things off your list, if you’ve been bouncing from task to task, chances are when you do start marking things as done, you might mark several off all at once in quick succession. This is where I’m at after a year or so of doing this. I don’t think I’ve marked any one full task off my list yet, but I’m *this* close to marking off Dropbox and both email accounts, and not terribly far away from finishing up a couple of other problem folders on my desktop as well! Over the next few months I suspect I’ll mark 5-6 things off one right after another. I know I’ve made progress every week, so I haven’t felt too bad about never marking anything as ‘done’. Still, it’s going to be awesome when that list gets just a little bit smaller.

Other Reading: Tidying Your Digital Life: The Initial Assessment

*Image taken from Pixabay, creative commons license, user geralt