Oh, I have the best de-cluttering secret to success - my mom. She loves decluttering and organizing (thank goodness). When I ask her sort a room, a closet, a drawer, whatever, she makes 3 piles:
1. Keep
2. Maybe
3. Ditch

This helps me see the items in smaller chunks. Sometimes her criteria for sorting into the 3 piles differs from mine, but it gives me a starting point and is less daunting and less emotional. It can really help to have a helper.