Story of my life so far:
1. accumulate stuff, both physically & mentally -- school, work, &c
2. feel overwhelmed by stuff, retire from job
3. attempt to de-clutter life, ongoing
It's not that the stuff isn't mostly worth anything. No, at least at the time I acquired it all, it was worth something to me. Turns out, though, that it's not all worth the same now as it was when I acquired it. I could get all deep & philosophical about this & talk about how we change with age, but it's old news so I won't bother.
The hard part is teasing out the things that matter to me now, and not lose them in a frenzy to de-clutter everything. You simply can't do that, there will always be some clutter. Simplification isn't just a matter of discarding unwanted stuff, it's a whole new mind-set.
I've seen it before in others. Just when you think you're ready to kick back & enjoy everything, you discover that you want to do & be more than that. So, what of all those things you acquired? Well, at least you had the pleasure of acquiring them. And most of what you acquired is useful for someone, somewhere.
Take costume jewellery as an example. Over the years, I've picked up a lot of interesting pieces at craft fairs & from individual makers & as travel mementos. None of it terribly valuable, I've only got a few pieces worth anything. Not even much gold, as I've always preferred silver. So, one of the things I did recently was go through it all and put aside things I'll never wear again. Took the lot to a family reunion & put them out "to a good home". Lots of little girls in the connection (& a few big ones) took up the offer. Feels good on both counts -- I gain some drawer space & they get something they like. Jewellery, if it had feelings, is useful again.
Same thing, only moreso, with clothes. We both went through our closets & drawers with a figurative back-hoe yesterday, and came up with 5 boxes of things that don't fit or we haven't even seen for years to go to the thrift shop. Also a bag of real cast-offs to go to the bin that sells old clothes by the pound for charity. Gain -- more closet space so clothes aren't permanently wrinkled plus good feeling that some less fortunate will get wearable things.
Next? Books. That's going to take a lot longer than the few hours for the jewellery or the day for the clothes.