I find that taking pictures of the items gives me that “it’s nice to be reminded of that time”. Then i can get rid of the item and still keep the nostalgic reminder.

Trash. Generally I’d say recycle, sell, or give it away, but there are times the best thing to do is just to throw it out

For me, it’s about understanding the value having it provides. It’s ok to have something for sentimental reasons, but it just having been present in your life doesn’t make it meaningful. If you keep a piece of clothing you can’t or won’t wear again, what does having it do? My dad passed and I kept one of his favorite flannel shirts because it evokes so many memories for me. But it’d have been silly for me to have kept all of his socks just because he wore them.

Personally I keep books and CD’s. I have lots from my teens and early adulthood. I like them, and I also like having a library that my kid can look through as he gets older. Clothes and furniture I’m not sentimental about though. Only keep what you’re actually going to use, sell, donate or throw away the rest.

When you see something that brings back nostalgic feelings, you don’t want to get rid of it. But in the end, if you haven’t touched it in 20 years and it’s just taking up space, you’re not gonna miss it when it’s gone. Get money for it if you can, donate it, or throw it away. I never regretted getting rid of stuff I forgot I even had.

Go through it, keep what is truly sir use and definitely try to sell or donate what you can, especially physical media since even without a lot of monetary value those are items that typically aren’t being made any more so are of a finite number. There are those of us that like collecting physical media and have the space to store and enjoy it so helping it get a second life is a better choice than just dumping it in a landfill to rot (almost literally) forever.

Otherwise the key is to relish the nostalgia of going through it but don’t let it color your decisions on what to keep too much. It’s okay to hold on to some things that truly matter to you just for sentimental reasons, but you shouldn’t try to keep it all. My wife and I each have a plastic tote in our basement of keepsakes, we try to limit sentimental things to just that one tote each to help keep it manageable.

I recently had to clear out my room in my childhood home and found all the schoolwork I ever produced until I left for college. I went through it, and ended up tossing everything except school photos as well as a couple of big written assignments I still remember doing.

So I guess my advice is to just stack-rank it and only keep a few particularly sentimental items.

Donate it to a library, shelter, thrift store, or similar. It gave you joy, but now it doesn’t. Let someone else have the experience.

I would go through regularly and part with an item that held least significance. And repeat monthly till I pared it down to a small collection.

Donate books to literacy place, or drop them randomly in the little libraries (if your city supports those citizen made structures).

CDs are a dollar at the thrift store, but if you have an artists set you might get a fan on Craigslist or kijiji or marketplace that wants them.

The word “worked” is doing a lot of heavy lifting here.

If your goal is to justify throwing things away, there are whole self help ecosystems built to help you to toss it all, from self transformation regimens to grief processing and everything in between. Find one you like and read, listen and engage about it on social media till you believe what it says then just throw all your stuff out.

You could also not do that and listen to your CDs and records, read your old books and either store your old clothes to give to your kids or use them as patch material for clothes that do fit.

It’s a question of forgetting your past or integrating it into your present.

I also digitize what I can. Then I separate what I actively use from the rest, separate those items into categories, pick out one or two (or three) of my favorites in each category, and donate the rest to a thrift store in hopes someone else can make better use of them. Still not foolproof though, on the shelf next to me is a keyboard and bin of cables that I haven’t touched in ages.

Go through the counter argument, what would it take to keep it?

From what you’re saying, you’ll likely need to rent a storage facility for that. They’ll advertise low rates initially, but I’d expect to pay over $100 a month unless you constantly move the stuff across different storage facilities. Then, if you move out of the area, you’ll need to bring this with you.

Once you have a cost to keep it, it will be far easier to justify getting rid of it.

Might be from Marie Kondo, or not, but I use a 1 year rule. Have I used this in the past year? If not I get rid of it, knowing I probably will never use it or enjoy it again, I’m happy to leave it in my memory, to stay or fade naturally. Hardest were gifts at first, by fear of offending the person that offered it, until I realised I don’t always remember what I offer others, and I wouldn’t be offended. Same for the first years of kids’ “artworks”, took pictures then trashed them