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I've started over with near zero possessions several times in my live so I'm not particularly attached to any of them.
I used to be unable to get rid of books but when I finally broke through that barrier (moving to Hawaii and my parent saying they weren't willing to to store them for me) I've never had a problem again.
One method I recommend for people is to put all the junk they think they're willing to give up, but just can't pull the triger is to put it all in moving boxes. On each box write a date six months or a year into the future and then store them somewhere.
Whatever is still in that box in six month or a year is something you obviously don't actually use, and then just take the boxes to Goodwill without even opening them (you probably won't be able to remember what is in them without checking).
If it has been taken out of the box over that time, then you can keep it.
The only reason to keep something you don't use is for decorative, sentimental, or investment reasons. If it is in your closet, it isn't decorative. If it hasn't come out of your closet in five years the sentimentalism isn't as strong as you'd like to think, and most people incredibly overestimate the investment value of minor collectibles.
Of course, that hasn't much to do with two Monopoly cards in an office drawer. In a school library environment I thikn the bookmark idea is a good one. Otherwise just toss them.
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