I do that too, not every week, or month, but probably every year. I have yet to regret getting rid of anything. I almost got rid of an old "word processor" (Canon Starwriter from the late 80s, early 90s). It didn't sell at the garage sale, and I opted not to take it to charity. I ended up using it on a few law school exams before they started letting us use our laptops. Saved my butt (and got me some high scores).
But if you feel like you might be off balance, go slow. Try this (I think this came from Suze Orman). Find ten things that are no longer of use to you, or to anyone else, and just throw them away. Then find ten things that are no use to you, but someone else could use, and take them to charity. You can do this once, probably painlessly, and see if that's enough of a taste for paring down your existence. If not, try it a few more times. (Suze's theory is that when you see how much money you have spent on useless crap, you will stop spending so much.)
I like not having a lot of crap around. It allows me to focus on my current deal and spread it out as necessary.
Now you got me itching to pare down. It'll have to wait until I finish my last final for this year of law school this Wednesday night (one down, one to go). I think I better cancel my plans for next weekend so I can join you in being off-balance. Have fun de-nesting-I really recommend it!
(I still take my starwriter to law school exams, as my back up in case my laptop crashes)
Shoshana