Un-clutter My Heart

My home has two kinds of clutter--the large objects that we have bought or acquired that are fantastic but have no place in an NYC apartment, and the piles of paper and assorted small objects that manage to self-generate on a fairly continuous basis. I have just about given up on the big ones. My main responsibility is keeping the small ones at bay. Which, believe me, is no small task.
 
Each night (or every few), I tackle a pile. The items, which range from mail to old school papers to hair ties to pieces of toys or games, are redistributed--sent back to their original owners for reorganization. The problem is, while the "original owners" may be willing to claim a hair tie or some stray Legos, the majority of the items tend to remain unclaimed, so it is up to me to decide what little treasures escape the garbage.
 
Easy, right? If no one wants it, just toss it. This may work well for toy parts and rubber bands, but what about last year's essay that got an A+? What about the cartoon that took hours to draw, or the paper evidence of a game that occupied my son and my sitter for hours? What about the manuals to random items and the discount flyers for the ten musicals we want to see but might never get around to? Nobody wants any of this, but if I am not the guardian of our past, present, and future, who will be? And so, the piles get chipped away, or moved to other piles, but are never quite gone--the daily self-generation makes sure of that. So the clutter remains.
 
Many years ago, I heard a "clutter consultant" (I think they are mostly called professional organizers now) speak about how clutter in your life could really get in the way of your getting things done. I get it--there are many things I'd rather do with my time than sift through papers and piles. The question is, where do necessity and history end and a clutter-free space begin? Would I give up items that make me smile in order to have a clear dinner table? Can I remember enough of my kids' growing up not to have props to refresh the memories?
 
I like smiling, and I like memories. So, while I'm sure I can get a lot better at moving through the present-related clutter, I suspect I'll be holding on to some of the stuff from the past. If I have to share my space with a first grade cartoon or a fourth grade essay, so be it. I'll clear my table, and my head, some other way.