I run into this issue almost every time I start decluttering (unless I'm in a particularly ruthless mood, in which case almost nothing is spared).
My problem is the actual discarding of the item in question. For example, I know I don't need to keep every single drawing my kids make or every single project that comes home from preschool, and I don't want to either. I would never wear my wedding dress again even if it did fit (it looks far better in the photos than it does in the box under the bed). I would not be upset if I went looking for most of this kind of stuff and realized it was gone. But the thought of actually putting those items in the trash or donation box kills me.
I am a huge proponent of buying clothing and furniture second-hand, so the idea of donating or selling things I no longer need is appealing and we do donate to Amvets or whomever on a regular basis. I know rationally that others can benefit from stuff we are not using and I want to give back to the thrift stores that I rely on. It's not a case of "I don't need it but I don't want anyone else to have it" at all. But certain things, even some that hold little or no sentimental value, remain in the house because I can't bring myself to physically cast them away.
Sometimes it's a case of what-if-I-need-it-someday, sometimes it's a gift I dislike but feel guilty getting rid of, but not always.
Does that make any sense? If these things were to just vanish on their own without my having to take them out the door I could live with that. I've even given my husband a box of stuff with directions to make it disappear sometime when I'm not looking, and that worked out fine. I know the stuff is gone and I'm even relieved about it (less crap to be custodian of), but I can't do the actual discarding.
Who knows what psychological problems this reveals about me - heh!
