My problem is that I am rather a Jeckyl and Hyde person, and also somewhat of a control freak when it comes to my own things. So I have never had any problem passing on clothes and useful things to friends and charity shops , especially the toy things as my son grew out of a particular interest or whatever. I did rather regret having given 3 lovely large toy vehicles which were very sturdy and could be ridden on, a fire engine, a digger and a lorry, to the kindergarten when I had my grandson to consider. But as I say they were not a problem.
When I had to leave my own house and move to this smaller flat, and give up my piano etc., it was a big wrench, although I chose to do it, knowing that my independance was the most important thing of all, but had to get rid of so much stuff that once I had moved it took me something like a year to even be prepared to get rid of anything from here.
However now I know I need to be thinning things down and so forth, but that does not include my precious books, which when I am dead they can do as they want with. No, it is the whole range of things such as letters or diaries that hold so much of my life and just looking through one, brings me back to countries and people I remember. Even things like special recipes and cookery things that I readily agree, that it is extremely unlikely I shall ever want to , or need to , cook now. BUT I dont want family to come and start going through things , as I want to know everything that is being thrown out and I miss my lovely husbands way that worked well for me.
So he would go through a drawer or a cupboard, but everything he was preparing to throw out, would be put on a tray or on the table for me to check over. That worked well, as occasionally he would have thrown out some important spare bit for something or other, but usually I only had to look things over and then could say thats fine, chuck them out. That way a lot of stuff was sorted but I still had peace of mind and that final say so as to whether something went or not. It may not work for others but it was very good for me , and stopped me getting too anxious about it all.
I now have to be in the right state of mind to tackle things, as I am on my own, and with my back problems etc etc., it is frustrating that I can be having a decent sort out and have to stop for a while, when I am in the mood to clear stuff. Still this is the time of year rather than spring cleaning for me, as the darker evenings , and the less good weather mean that I am at home more and can tackle things more often. I need to be in the right mood, and then do get a fair bit sorted, whereas on another day I take so long to decide about stuff it is pathetic.! So I have now devised my own way over those things that you just cant make up your mind whether they are worth keeping or not. I put those things in a black plastic bag and stick it far back in a cupboard. After a couple of months , if I havent rooted anything out or gone looking for something I get rid, without looking through again!
Another thing we have done that went well at one time. In a womens group I go to , we gave a fair bit of notice and agreed to bring up to 5 items to the meeting, that we wanted to swap. Then we had 2 people looking at the items and they and the owner agreed its worth. So we had raffle tickets, which were easy to acquire. So for example you might have a cashmere sweater that you no longer wear, but in good order, so that would probably get 5 tickets, and a simple pair of gloves 1 ticket etc. Then when we had taken in all the available clothes. everyone could go round and use their raffle tickets to "buy" another item. Firstly we only allowed people to choose one item so that everyone got a fair chance to get something they wanted, and then just carried on until everything was chosen . Anything still left could either be retrieved by the original owner or given to go to the charity shop. All the items had to be clean and in good order or we would not accept them at the beginning. Result - quite a lot of fun trying things on and some decent bargains, and people felt good about themselves for sorting something out!
Sadly the only person who can sort out paperwork is me, and at the speed I am working at the tortoise will have passed me and been round twice !! Ah well I have made a start, and need to hope for that good combination of a determination to clear a lot more, and there to be very little or nothing going on, and no excuse to avoid starting. Then usually I leave the bag of stuff in the hall for an evening, just so that I can look at it and know that I have at least cleared that out, as when I look in the room I have been working in I often cant see much difference!!