I donated about 90% of my things for the first time at 19. I had decided to wander for a while, sleep outside, and at friends houses, at the beach. I said to my friends, take whatever you want. One took the hunting knife collection. One took a lot of clothing. One took a lot of my cds. Etc. I kept a backpack full iof stuff, plus 2 paperbags full. purged about 75% again at 21. Again at 30 about 75% with the konmarie method. Each time I decluttered I had accumulated more of course, but wiith this last time, I am hiping ill be more discerning....
In regards to regrets, really only a few. All are books, mostly kids and young adult. And this is only because I haven't been able to find them again! Some books are extremely rare, but cèst la vie. I figure if I'm meant to read them again, I'll come upon them someday. Otherwise, I hav donated many many other books and don't miss them, hav got a couple from the library to reread.