Whenever possible, Frank Lloyd Wright designed homes without garages, basements, or attics. His reasoning was that if you give people a place to put clutter, they keep it. It's the same with digital files: People hang onto the things they don't need because they can.
Having unnecessary clutter in a home makes it ugly. Trying to work at a messy desk rather than a neat one is distracting. There is a cost to clutter, even when it's digital. The more unnecessary stuff you have, the harder it is to find what you need and want. More importantly, storing and backing up files is not "free" by a long shot. There is a real cost in energy, money, and physical space for servers, not to mention the cost of all those things to the environment.
If you want to be more organized with your digital stuff, you have to get comfortable with deleting a lot of it. The accumulation of stuff you don't need prevents you from organizing what you need and care about.
Make Deleting Your New Habit
Deleting digital files can be an uncomfortable or even painful process, and you might avoid doing it out of fear. One key to making it easier is to make it a habit: The more you do it, the easier it gets. But creating new habits is hard. So here are a few very specific tips and tricks.
Cull Your Photos Right After an Event
Digital photos might be the number one offender when it comes to the files people keep but don't need. Even a modest phone might have 128GB of storage, which you can pack with thousands of photos.
Make a habit of going through what's on your phone right after an event if you took any photos at all. For example, if you're on a plane coming home from a vacation, use that time to go through your pictures and cull some of them. Go through your photos if you're unwinding on a Sunday after a day out with friends on Saturday. You likely have multiple shots of the same thing, so pick the best two or three and delete the rest. Delete any that are blurry, ugly, or just plain weird. You might tell yourself you'll edit them later, but will you? Send them to the trash.
Use the '4 p.m. Friday' Trick
If you work a standard set of hours, assign yourself a task of deleting files at 4 p.m. on a Friday (or the last hour of your particular workweek). Why then? You're probably tired from the week, which makes it a perfect time to tackle a task that requires little focus. In other words, you get to be productive with little effort.
Trash emails that are junk. Throw out files on your desktop or in your online storage service that aren't relevant anymore. Close tabs for web pages you will never read. Make 4 p.m. Friday your time to rummage through your stuff and clean it out. Not everyone enjoys looking back through their old junk, but I actually do. For me, it's just as satisfying as, say, reorganizing my bookshelf.
Trash at the End of the Month/Quarter/Year
Putting files into your computer's trash bin doesn't actually delete them, and closing tabs on your browser doesn't wipe the browser's history.
Decide how often you're willing to clear the trash and put a repeating event on your calendar for it. I recommend doing it monthly, quarterly, or, if you're really lax about it, yearly. A New Year's Eve dump is better than nothing. iPhone users should know that putting photo files into the trash means they will automatically delete them after 30 days.
Deleting the trash is the real final step in letting go of the things you don't need.
Feeling Stuck? Ask Yourself, 'Will I Miss It a Year From Now?'
The hesitancy to delete often comes from the fear that I might need it, though. Ask yourself, will you really need this photo, file, or email a year from now? Two years from now? Be honest and don't hedge your answer.
If the chance you might need the file is close to zero, just delete it. What happens when you don't is you effectively lose it in the clutter, and then it's much harder to delete it two years from now when you're sure you no longer need it because it's in a heap of other stuff you don't need, and it all feels so overwhelming that once again you do nothing about it. Deleting files as you see them is simply more effective.
Learn to Love Letting Go
The hard truth about being organized, especially with digital stuff, is you really have to delete ruthlessly. So many people believe they want to be more organized, but then they never delete anything and nothing changes. Getting in the habit of clearing out files permanently is, quite frankly, the trick to it.
So get in the habit of letting go. You might even find that you grow to enjoy it.