Why do I have so much stuff? I hate it all. Should I give it all away? Ugh or set it on fire (probably not very eco-friendly but very emotionally satisfying)
What shit is worth holding onto? (This seems like it might be a pretty deep question. Discuss.)
Does it have a practical use that you can forsee? Does it have emotional sentiment? Do you like it? If no to all of these, give it away.