Sometimes clients will ask, "Why am I hanging on to all these things?"
I tell them that it's impossible to know why. Too many factors combine and contribute to why there's clutter, and that makes it impossible to know what they all are. Any "whys" my clients might come up with tend to be stories they tell themselves, fantasies that distract them from their clutter situation.
The only thing worth knowing during a clutter bust is that the presence of clutter is hurting your life. If you had rats in your home, you'd skip the "whys" and call the exterminator.
Most of the time, skipping the "whys" and getting to the what's in front of you is the only thing that's going to make you feel better because it's the only thing you can do something about.
There are a few times that I've seen an examination of "whys" make a difference -- but the answers always come after the clutter bust, not before.
If you find yourself trapped under the influence of "whys," stand up, walk over and pick up something. Feel it in your fingers. Think, "If this was food, would I want to eat it?" See the job, do the job, and stay out of the misery.