Depends on the clutter. My desk has lots of little dopey things, a million different types of pens, and paperwork I don't really have a place to file yet (I hate to waste a new folder just for one or two pieces of paper that will most likely be trashed after a certain amount of time passes). My room has books and stuff I intend to read (Harry Potter's been waiting a year) and knick-nacks and frames I HAD to have for some reason.

Once I get bored looking at something it goes into a closet, cabinet, box, to the basements, etc. After a few years, I look and evaluate whether or not I truly want it.

I finally tossed out all my "Skinny" clothes figuring if I lost weight at this point, I would reward myself with new clothes because the clothes would be hopelessly out of style anyway I tossed out a ton of crap that a few years ago was soooo important (the mini bottles of bubbles from my wedding? What was I thinking I'd need them for? Emergency bubble making???)

I still have all the drawing books I'd kept from my childhood. My diaries too. But I tossed out a ton of photos that were of people I no longer see or care about.... and photos that had my mom's thumb in the center

I tossed out stuff that was perfectly good but missing parts or pieces or needed some TLC. I wish now that I participated in freecycle.org because someone else could have really been happy to take it.