But going through them did help me in my future decluttering. Here are some of the techniques I've used on myself. If you have others that have worked for you, please share!
Swapping OutI lost my parents when I was relatively young. Some things that may look useless, like a plain drinking glass or an out-of-date standing lamp, are holy relics to me. My early attempts at decluttering ended up with me caressing them for a moment and then just packing them in boxes, labeling them, and putting them in the basement.
Those things are still in the basement. I've realized I can't let go of them just yet, but I'll get there. In the meantime, I look at things that have no emotional hold and say, "If I get rid of this, then I'll have room for momma's clock."
If there are things you feel you absolutely can't get rid of, tell yourself you can keep it if you get rid of something of equal size, or maybe two things that take up the same place, and then find things that don't carry an emotional attachment (like that electric pencil sharpener that stopped working and the lamp that doesn't provide the right lighting for your workspace).
Consider using an online photo service to create a book of memories.
Tip: Make sure you back up your photos and electronic journals.
I found the act of viewing and photographing the things I release very soothing. Capturing it digitally means that I can look at it any time: I don't need to hunt for it in boxes, go to a storage area, or dig it out of the bottom of a closet. The exercise of writing about it -- which I haven't started yet -- will be even more meaningful since I'm a writer.
I'll be writing a different blog entry on releasing (getting rid of) general items later, but emotionally-charged items have another destination you might consider. Is it grandma's old sewing machine? Maybe a cousin or a friend of the family wants it. Now's the time to get in touch.
If not, and it's very old, consider your local historical society or a museum related to the item. For example -- and I'm making this up -- maybe it's an old canning set and there's a museum of food safety. If it's it good condition, they might be interested. And now that you have the photos, it's easy to send them an email and say, "Are you interested in this?" If you live in the US and you file the long-form for taxes and the recipient is a 501(c)(3) organization, you might be able to deduct the value of the item from your taxes.
If you are downsizing because you are in dire financial straits, you can sell it. Now that you have the photos, it's easy to upload them to eBay or email to people you know who might be interested in them.