I round up bags and bags of stuff to go, then when I get around to it, I drive up to the charity bin or to St Vinnies, and have to take the bags from the boot. I find that whenever I do this, I feel a last minute sense of panic that I am getting rid of something I shouldn't, and I often do a quick rummage through the bags, take a couple of things out of each, and then take the bags to the shop or bin.
The silly thing is that invariably when I get home and see my 'rescued' items in the boot, I wonder why I did it. I always think later that I didn't really need to keep these things.
I am not sure where this panic comes from...maybe just the fear of regretting what I am tossing...
I do. Sometimes I will really look at something before I put it in the Goodwill box. Then I might change my mind and take it out. As I'm putting other items in the box I'll put it back in. Or keep it out and then it'll go in the next round. Yesterday dh and I took a large trash bag full of clothes and shoes and a small box containing vhs tapes and cds. I'm conscious that in the back of my mind some of the items may be a question mark but when we drop them off I put them out of my mind and drive off quickly. I think we develop a real emotional attachment to our stuff which can be unhealthy. But of course there are times when we think that perhaps we really could use such and such. I try not to get rid of my things impetuously so that I'm not sorry for it later although it has happened.
One thing we've found helpful for our son is to bundle stuff up and put it in our storage shed for a while. Then, since no one misses it, or even remembers that much of what's in it, it's fairly easy to toss it.