I have been thinking about stuff, getting prepared for my upcoming NSGCD teleclass. While some chronically disorganized people are likely to have an emotional attachment to their belongings and would find this exercise very difficult, those with normal organizational abilities might find it useful or thought provoking.
One could use the categorizing concept of Hot or Cold - hot being more inclined to using or wanting it. Cold being more likely to be discarded. You could also use the Love it, Hate it approach. Loving it being a keep and hate it a toss. Another option would be the Numbers 1 - 5. One (1) being a keep it, and five (5) being a toss it.
Those mid-value "warms" and "3's" are likely to be difficult, but to take it further - would they be among your take with you items if you left your environment due to an impending flood or raging wildfire approaching your neighborhood?
Many years ago I read the story by T. Coraghessan Boyle (T C Boyles) - Filthy with Things. The New Yorker (February 15, 1993): 76-87., where a woman came in and worked to declutter a fully packed household - and declared that her client's needed to clear out their home, get it inventoried and could only have 100 things brought back in.
What would your 100 "stuff" things be?
Would they be practical or creative?
2 Arm chair
4 loved works of art
1 bottle of favorite perfume
5 favorite books
or would you put together a mix of both?