Challenge: Eliminate Possessions

Okay I need some sort of small challenge to eliminate some possessions. Any ideas?
We can move to a larger house or start moving out some of our things. Moving is always an option but purging is always a good thing to do.
I know if you have not worn something in a certain amount of time that it should be tossed. I also know that we use and wear only 20% of what we own.
Why is it so hard parting with possessions? Clothes are easier for me that gifts of another nature to dispose of. Clothes are worn, outgrown and styles change.
Other possessions are clung to thinking they will be one day be needed.
Any idea for a challenge that others can do also?
I am willing to take on more than one.

For example:
attack the linen cabinet
donate some shoes