Paperwork is one of the toughest forms of clutter to vanquish. Often, it’s much more anxiety-provoking and draining than going through a clothes closet or a desk drawer.

To decide what to keep and what to toss, ask:

• Do you actually need this piece of paper or receipt? What specific use does it serve?
• Have you ever used it? If you’ve never referred to a category of paperwork, apparently you don’t need it.
• Will it quickly become dated—like travel or summer-camp information?
• Does the internet mean that it’s no longer necessary? For instance, the instruction manuals for most appliances are now online.
• What’s the consequence of not having it if you do need it?
• Was it once necessary but is now related to a part of your life that’s over? This can be hard to recognize. Do you need that sheet of home phone numbers for the members of a team that you left two years ago?
• Could you scan it, so that you have a copy if you need it?
• At work or at home, does someone else have a copy of this information?
• Look in your paper-organizing gizmos. When I look at people’s work spaces, I notice that they often have file stands, wall-mounted paper organizers, stacked shelves and in-boxes…all full of old papers that no one ever looks at. Unless you’re actively moving papers in and out, empty out those units, and get rid of the units altogether! They’re often just clutter magnets.
• Have you verified your assumptions? For instance, when you took your current position, your co-worker told you, “I always keep these receipts,” so you assumed that you need to keep them, too. But maybe you don’t.

Some additional conversations…

Whenever we clear cutter, it’s useful to ask, “If I had to replace something I’ve tossed or given away, how hard would it be?” This question can help with papers. If you shred a bank statement but end up needing it, you can get the statement online or call your bank. If you toss your diary from high school, you can’t get it back. So think harder about the diary than the bank statement.

Beware of binders! For some reason, I’ve noticed that many people have an urge to put papers in binders. But do you really need those papers at all? One of the biggest wastes of time is doing something well that didn’t need to be done at all.

Along the same lines, I got an email from a teacher who complained about how much time she’d spent shredding old lessons plans and student essays. Why do those papers need to be shredded at all? I talked to a guy who was planning on putting all his papers in chronological order in binders (binders!), then realized that most of the paperwork was related to pet insurance, and he could access his account online. He didn’t need to save those papers at all.

Some people worry about regret—that they’ll sort through the papers, get rid of a lot of it, then wish they’d kept some of it. In my observation, this is rarely a problem. However, if it’s a real stumbling block for you, create a holding box. Put papers in that box for six months—or even a year, if you’re really worried—and see if you ever need to retrieve anything from that box. If you don’t, get rid of the box—and importantly, don’t re-open it first! Or you’ll re-ignite the whole problem of uncertainty.

We want to get organized, but not too organized. Don’t make files so specific that you can’t find anything later, or so that you spend all your time labeling files.

I’ve come up with a system that works really well for me. I have a folder for every month of the year, and any information related to that month goes into that file, whether it’s a party invitation, agenda for speaking at a conference, information about a school event for my daughter, or notes for one of the live shows that Elizabeth and I are planning. That makes it easy to know exactly where to find timely information, no matter what part of my life it relates to, and easy to see when paperwork is no longer necessary.

Bonus: To make those files more fun to maintain, years ago, I bought bright, well-designed folders and had my then-little daughter Eleanor write the days of the month on them. It’s still fun to see her childish handwriting when I grab a folder.

This kind of paper clutter is difficult, but so rewarding! Think of how great you’ll feel when you get that pile of files off the floor, or clean out that curled up, yellow papers. It’s tremendously free and energizing to clear out that stuff.

If you want to learn more about creating outer order, order a copy of my New York Times best selling book, Outer Order, Inner Calm or pick one up at your local bookstore.

Gretchen Rubin is the author of the #1 New York Times Bestseller The Happiness Project—an account of the year she spent test-driving the wisdom of the ages, current scientific studies, and lessons from popular culture about how to be happier—and the recently released Happier at Home and Better Than Before. On her popular blog, The Happiness Project, she reports on her daily adventures in the pursuit of happiness. For more doses of happiness and other happenings, follow Gretchen on Facebook and Twitter.

Image courtesy of Antonino Visalli.