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.)
Most of my items have utility, how do I proceed in shedding possessions?
Why do you want to get rid of things you'll need?
I have a lot of stuff. It's all useful but surely I don't need it all.
I guess ease of replacement, likelihood of needing again soon, whether or not you can do the same job with some other item or combination of items