Letting go of possessions before planning to downsize

I've been trying to organize my thoughts about possessions into a neat package.
It's almost as messy as the objects themselves.
Much of our possessiveness of things seems to relate to wanting to hold on to past feelings and memories-not a bad thing (some memories are truly rich)-but it does cost time. energy and space, which also could be used for today's life.
I find it almost puzzling to look at old family pictures, realizing that when I'm gone, so one will know or see the people and memories I see. Fortunately photos don't take up that much room. A few of them may go to a historic research collection where they will represent a certain era.
I ask myself often "Would this space be better used for something I can do today? If I look at this object honestly, is it of any larger value beyond my feelings?"
This also means I need to ask "What do I want to do with the rest of my life? What can I honestly expect to do? How important is remembering the past? (YouTube offers many walking tour videos of the old town where I grew up. Some times I recognize the old brick sidewalk! That also takes time!)
Time to clean the back porch. We can enjoy the space.

If you're in the process of cleaning out 50 years of possessions, I have a few suggestions ... before starting, Get Valuables like Jewelry or Important things you Absolutely plan to keep Out Of The House & put into a Secure Place (possibly Locked up).
First: invite an Appraiser in to look over your things. Chances are after 50 years some of your belongings ought to be valuable "Collectables", & worth a few $$$. After you've done this, pull out the things you plan to gift to family or special friends, & either give it to them, or stash them somewhere "out of the way".
Then invite the rest of the family & close friends in to select things they may appreciate as a remainder of YOU. If you have books, think about the fact that some of them May Just be 1st Editions, or books that are "out of publication", hence: Collectable = of greater value now than when they were new. (My Husband went thru his Parents bookshelves, selected books he Loved, or he knew his Parents Loved. Among their books (in our house all of the bookshelves on either side of our Fireplace) are 1st Editions we've inherited from them ... F. Scott Fitzgerald, Hemmingway, & a number of Other Collectables, most now +- 100 years old. Our Grand-daughter TREASURES her Great Grandparents 1st Edition copy of The Great Gadsby. (& I might mention its' present-day value is +- $300.00). Next you may choose to invite Family & close friends to come choose books They might like. Neighbors too may be invited to come look over what's left. If you still have "Stuff" to dispose of, selected a weekend & have a 2-day "Garage Sale". One TIP: price things a little higher than you'd like because Garage Sale People almost ALWAYS "haggle the prices down". Don't be Astonished with how quickly such things as kitchen utensils or linens sell for. Oft-times dining room & bedroom furniture sell pretty well, especially to young couples who can't afford to buy New, or recognize the quality of older furniture over what's being manufactured & sold today. All Together your 'out-of-pocket' expenses were minimal, & you might be was astonished at how much $$$ you put in the bank when it's all over. Spring & Fall are the best times to do this ... if there's a college or University near-by, Be Sure to put a Notice (with a list of Some of the things that'll be available-for-sale) on Bulletin Boards there. You'll draw buyers who walk out with Surprising, Unusual items, & Guess What, generally College-crowd buyers don't "Haggle over price" like the Antique dealers & other Garage-Sale shoppers Do!
When you're finally to the point where "You've Had Enough", Habit For Humanity is a good place to consider as your "Last Call". After they've left you shouldn't have much left to haul off to The Junk Yard.
I know I've offered a Lot of Options ... Hope you find at least 1 of these suggestions helpful.

@celia16. Before you get that truck, if you have a garage, Why Not ask a neighbor if you can park your car at their house for a couple of days, then stuff out to your garage. About a week before your "Sale Weekend" Post some signs at local Grocery stores, College Bulletin Boards, your local Library, & anywhere else with a free "Post-Board" announcing your Garage Sale.
I did it about 10 years ago & cleared $250.00 in 2 days. The stuff that was left I boxed up, called Habitat for Humanity, & donated to Salvation Army.

If you're in the process of cleaning out 50 years of possessions, I have a few suggestions ... before starting, Get Valuables like Jewelry or Important things you Absolutely plan to keep Out Of The House & put into a Secure Place (possibly Locked up). Give away the things you know others might like.
First: invite an Appraiser in to look over your things. Chances are after 50 years some of your belongings ought to be valuable "Collectables", & worth a few $$$. After you've done this, pull out the things you plan to gift to family or special friends, & either give it to them, or stash them somewhere "out of the way".
Then invite the rest of the family & close friends in to select things they may appreciate as a remainder of YOU. If you have books, think about the fact that some of them May Just be 1st Editions, or books that are "out of publication", hence: Collectable = of greater value now than when they were new. (My Husband went thru his Parents bookshelves, selected books he Loved, or he knew his Parents Loved. Among their books (in our house all of the bookshelves on either side of our Fireplace) are 1st Editions we've inherited from them ... F. Scott Fitzgerald, Hemmingway, & a number of Other Collectables, most now +- 100 years old. Our Grand-daughter TREASURES her Great Grandparents 1st Edition copy of The Great Gadsby. (& I might mention its' present-day value is +- $300.00). Next you may choose to invite Family & close friends to come choose books They might like. Neighbors too may be invited to come look over what's left. If you still have "Stuff" to dispose of, selected a weekend & have a 2-day "Garage Sale". One TIP: price things a little higher than you'd like because Garage Sale People almost ALWAYS "haggle the prices down". Don't be Astonished with how quickly such things as kitchen utensils or linens sell for. Oft-times dining room & bedroom furniture sell pretty well, especially to young couples who can't afford to buy New, or recognize the quality of older furniture over what's being manufactured & sold today. All Together your 'out-of-pocket' expenses were minimal, & you might be was astonished at how much $$$ you put in the bank when it's all over. Spring & Fall are the best times to do this ... if there's a college or University near-by, Be Sure to put a Notice (with a list of Some of the things that'll be available-for-sale) on Bulletin Boards there. You'll draw buyers who walk out with Surprising, Unusual items, & Guess What, generally College-crowd buyers don't "Haggle over price" like the Antique dealers & other Garage-Sale shoppers Do!
When you're finally to the point where "You've Had Enough", Habit For Humanity is a good place to consider as your "Last Call". After they've left you shouldn't have much left to haul off to The Junk Yard.
I know I've offered a Lot of Options ... Hope you find at least 1 of these suggestions helpful.
The money I made I donated half to my church & half a local Charity.

@blm1007blm1007
My adult daughter's church has an annual Books, Beans, and Brownies Sale. Come browse the book sale, grab a bowl of bean soup, and take some brownies home from the sale. That is where all the excess books that I have will go. When I moved to this house 11 years ago, I didn't have room for one bookcase in this new house so I'm already eliminated that many books. I'm beginning to realize that a lot of the books that I have not yet read probably won't get read; a considerable number no longer interest me. Those can go to their book sale. My daughter visits about every other month so I'll have some boxes of books ready to go back with her on her next trip.