I've accumulated a lot of stuff over the years, and a lot of that stuff had taken up seemingly permanent residence on my bookcase and in my closet. On a whim, I started cleaning out my bookcase. I don't know what came over me to start, but once I did I knew this wasn't going to be a one time deal.
When I do these big cleaning sprees, I usually separate into three piles: keep, trash, and donate. The donate pile is the one I usually have the hardest time with. One reason is that I have a hard time deciding whether to keep certain items, or if it's okay for me to part with them. The second reason is that it's hard to gauge whether certain items are in good enough shape that they would be worth donating, or just throwing it away.
The hardest for me is usually books. I have always been an avid reader, and so has my family. We're not big ebook people, so we have a lot of physical books. A lot of them I haven't read in years, just because they were from when I was a kid or a teenager, and they were simple stories that don't really interest me now that I'm at an adult.
Good news for me is that I'm weird about books. I don't like creases, bends, or folded pages, so the majority of my books are in excellent condition, so they can go to people that will actually read them.
Also good news for me, I have a lot of younger cousins. So all those books from my childhood, can go to them if they want them. And whatever they don't want, will hopefully be able to go to the public library.
It's good to be able to take an inventory, and decide what you want to keep and what you're okay parting with. You can acknowledge that something once entertained you, but you won't really get any more pleasure for it, and hopefully give that joy to someone else.