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.)
What things do you use a lot? What things do you need to survive physically? What is important to you emotionally? What makes you comfortable? That's how I decide what I need to keep.