We've moved a lot over the years. I use the opportunity to clean out things, but we always end up running out of time and just throwing stuff in boxes to get it from one place to the next. Or it's stuff that we think we want to keep but won't have room for it in our new location. That happens when you move from a 2000 square foot house with oversized 2-car garage... to an apartment with no garage... to an even smaller space with no garage and no storage space at all. Some of those boxes have been moved several times without being opened. Eventually, those will come back to haunt you.
Recently, several things occurred which made it necessary to clean out both our storage building on-site and a storage unit that we rented. I actually started going through those boxes. You know when you open a box and say, "why do we even still have this?" I hate when that happens, and it happens all too often.
This time I got more hard-nosed about it. There are hobbies I have parts and supplies for, and I'm just not interested in them anymore. There are items that I kept because someone gave them to me, souvenirs and mementos from trips we took, and possessions from what our lives used to be. Several truckloads of things have been taken to an indoor flea market for resale or Goodwill or ReStore (Habitat for Humanity store with hardware parts and pieces). I've also given away several boxes of miscellaneous fabrics and crafts supplies and have more to go. It's liberating to free yourself from "stuff," and I'm glad that others who can use it are happy to have it.
A few years ago, an elderly friend of mine realized that some of his friends had died and left their possessions in a mess, and their children had to sort everything out and figure out what to do with it. He said he's going to start cleaning everything out, because he doesn't want that to happen to his son.
The older I get, the smaller I live. If I get to the end and have only memories, some photos and a few clothes and books, I'll be fine with that. The best legacy I can leave my daughter is that I lived well and left her with no baggage.