Hey pal, these are good questions. Some years ago I shifted to a minimalist style at the encouragement of someone in my life. It was very anxiety provoking at the time, but brought me a lot of emotional freedom and relief.
When I moved from the UK back to the USA, I moved with two suitcases and I shipped one large box. Now, that is a little extreme, but it vastly simplified my life. I now have a house and have resisted filling it with random stuff because it feels good to have the physical space and airiness and also to not feel a great deal of emotional attachment to things.
For me, it requires a number of large purges of things over time - there is only so much you can do at once. Maybe pick one room at a time and work on it. Get a friend who has a clutter free mentality to come help you - I do this for my friends and in my office and get somewhat ruthless (when asked to be that way!) in helping to question the need to have particular things. Get some trash bags and boxes. Go through everything in that room and one by one, work your way through the objects in the room. Sometimes it helps to start with the easy stuff first. With each thing, I like to think about 1) is this useful? when did i last use it? 2) does this object bring me joy? 3) is this something I genuinely want to carry forward with me in my life?
I try to only keep things that really give me real joy. I don’t keep things because they remind me of something or someone, or because it is something I used to like, or because I have it, or because “I might use it someday”.
So I o through everything one by one (with the help of an objective and disinterested friend who does not keep clutter themselves) and separate them into 1) what you can throw away (trash bag) 2) what to donate (another bag/box) 3) what you feel is too hard or unsure to get rid of (yet another bag/box) and 4) what things really bring you joy or you use on a daily basis (keep). With the (3)s, I box those things up and stick them in a basement or under a bed or whatever and just leave them. Some things are too hard to just get rid of. So I let things sit there for 6 months or a year and then go through those boxes. I usually think “huh, this thing I thought I needed, I didn’t go looking for in that time and didn’t really notice it was done, maybe I don’t need it after all” - then it is gotten rid of, put on the shelf or put back in the box.
A hard thing for me was getting rid of lots of books. I used to be the person who felt an attachment to a lot of books. Then I was moving a lot it was a pain in the ass to be moving boxes of books, so this person in my life really challenged me about whether I needed them or not. Libraries have books, I switched to kindle for a while, etc etc. Now, I own probably less than 15 books. I only have that many because it’s been a part of my recovery to read reference books about alcoholism and trauma etc (before this, I had probably 4 books). I only keep the ones I know I will go back and reference from time to time. Everything else I donate or lend out after I’ve read it.
Hope this all makes sense and feel free to message me if you want more advice or to bounce ideas.