You probably know, since I talked about it incessantly, that I recently had my house professionally organized. (By Isolde from Getting It Together Organizing, in case you're looking for your own organizational professional. She was great.)
I never really felt like we did anything that I couldn't have done on my own--it's not that I can't put my stuff away, it's that I don't--but having someone else to help, and impose deadlines made it actually happen. There were, however, a couple of really interesting insights that I think will help me actually stay organized, and they were a little bit counterintuitive.
The first is that it's not all about simplicity. Most organizing books and websites talk about simplifying things and making it all easy. As Isolde noted, that's not the right path for everyone. I like complexity. I like my things tediously sorted, preferably categorized in obscure ways and then filed alphabetically. It wasn't a matter of finding an easy way for me to just shove my CDs away somewhere--I need the value created by having them truly organized to make it worth even bothering to put them away.
The next is that you have to fill spaces deliberately to prevent yourself from filling them accidentally. This is probably what all those zillions of people who buy knick-knacks already know, but it came as a surprise to me. I always figured the ultimate goal was a house where nothing was visible--everything was put away in its place, and all your countertops and bureau tops and everything else were pristine, clean, flat surfaces. But that's not maintainable. If you've got a nice flat surface with nothing on it, it's a magnet for stuff. If you've got a nice flat surface with a vase and some candlesticks on it, you can't throw your purse down there, because, hey, there's already something there. Vases aren't really for decoration--they're to keep you from putting something else where they are.
The last is that you have to recognize appropriate limits for clutter. You are not going to immediately put away everything the second you use it. And some things really do belong in the junk drawer. In my case, this has mainly manifested itself in little tricks to handle some of my ongoing trouble spots--mail, CDs and books.
I tend to toss mail in a zillion random places and it builds up until I get sick of it and throw it all away. Now I've got a little five slot mail sorter. When the sorter is full, I have to take something out--deal with it, file it, throw it away, whatever--to put something new in. My mail isn't piling up, because it's limited by the rack, and because the rack keeps it in one place.
Similarly, I get a lot of new CDs, some I buy, some I get to write about. They tend to accumulate around my house until I finally get sick of it, and spend the time needed to break them down and file them away. But the 'sick of it' point is too far down the path of disorganization, so we created an artificial limit that's a little more reasonable. I have a 20 slot CD rack sitting on my desk. As I buy CDs or pull them out to check liner notes or whatever, I pop them into the CD rack when I'm finished with them. When the rack is full, it's time to break them all down and file them.
Books I buy a lot of, and then read slowly. They tend to wind up all over the place, and I'm never entirely sure if I've actually read all of the books that I own. There's a shelf in my bedroom specifically designated for books I've purchased but haven't read yet. It's a limited space, so once it's full, I know to stop buying new books. But I also know exactly where to find all the books I haven't read yet.
These things seem a bit disorganized--piles of books sitting on a shelf don't look like they're 'put away', but the pile has a purpose, and it has a limit, and that makes it good, not bad organization.