I am very messy and my house has everything just strewn around so I have to keep very minimal possessions. I get my mail at work so no paper. I do most of my cooking at work so no food mess. I have no desire for pets, books, lots of clothes. I deliberately have no messy hobbies. I read Kindle rather than books. I live in a tiny cabin with a bed, ironing board, small table, office chair, stove, sink, reefer, kitchen cabinets, a built in bench and shelves and a tiny bathroom. It is really cute and on a very expensive property. I have no desire to have people over..would rather meet them someplace.

Put all the cds and vinyl in a laundry basket or six. Likewise any clothing out. Likewise any paper. Try to recycle paper as you see it...whatever you printed out you most likely don't need. Recipes etc...unless magazines are very specialized, take them to the nearest laundromat. People love them. Same for cheap paperbacks, trashy novels etc.

It is OK for something to hurt if you give it away. Other people need it or it needs to be transformed from paper clutter into new books etc.

When you have gathered stuff to donate, do it right away..don't let it linger.

Get rid of cheap and bulky items first..old dishpans, bathmats etc.

Ask for help and accept it. Limit it to one category..sorting through clothing or even just tops at first.