I've been cleaning out files, sending some to storage, figuring out what to do with others, and trashing a lot. I can't believe the crap that people keep. Does anyone believe that there will ever be a use for the drafts, redlines, redrafts and comments leading up to a contract that was finalized several years ago? Do they reckon that historians will want to know how that nonexclusive distribution agreement was drafted back at the begining of the third millenium? What fascinating history was behind that choice of venue clause? There's about a one in a billion chance that those drafts could be used to help in contract interpretation, and it is just as likely, hell more likely, that your documents that you saved are going to bite you on the ass. If you're stupid enough to keep this stuff, you're probably not smart enough to negotiate a contract, either.
And another thing. You don't have to print every fracking e-mail you ever sent or received and save it in a file, especially e-mails where you thank someone for their goram e-mail. And when something is done, it usually suffices to keep the final product, whether it's a contract, pleading, responses to discovery, letter or what have you. Nobody gives a frack about your creative process!
Before you make a file or put something in an existing file, ask yourself why the hell you are considering keeping the damned thing at all? What would be the downside if you threw it away? I let throwing away serve as my default, and unless I can think of a good reason to keep something, it's gone, especially if I know that our lawyers or other representatives have the thing in their file.
You don't have to print every attachment to every e-mail and save them in a file. Just read the ones that interest you on the screen, or if you print them out, toss them when you're done, unless you have good reason to keep something.
Just because you had a reason to keep something initially, you don't have to continue to keep it when that reason no longer pertains. Purge your files once and a while! Delete your old e-mails regularly. It's all potentially incriminating in the hands of an unscrupulous (Is there any other kind?) prosecutor.