I have made two cross country moves in the past decade as well as downsizing from a 1,000 square foot apartment into a 360 square foot one (thank you, San Francisco.) In the process I have learned one quick tip for being brutal with clutter:
Don't start by taking things away; instead, clear the decks and add them back in.
It is incredibly difficult to create the emotional space needed to honestly assess our stuff (but, I really like that mug!) and the process can be taxing. By focusing instead on the items that we use the most and adding only those back in it becomes easier to see the bigger picture and let go of what not longer fits in.
What are your tips for letting go?