Here's what I learned from finally going through all my stuff and selling/giving/throwing most of it away. It's all about triage:
Take ample time to sell high-quality in-demand stuff for a good price.
Do this first, if possible. Clear somewhere in your home (and a folder on your hard drive) to dedicate to organizing, temporarily storing, and packing/shipping actually valuable stuff.
Make this distinct - and higher priority - from other downsizing tasks. This one actually pays! Disposing of your previous laptop or iPhone is not akin to getting rid of, say, a Napoleon Dynamite DVD.
Note that you can process and store items in this category together with items in the following category, but do make a distinction for the valuable stuff. Give it more time/attention/marketing muscle.
List anything worth over $20 for sale and hope for the best.
Between eBay fees, credit card fees, postage and handling, and materials, you won't make much even on a $20 sale. But you can learn to create tidy listings (eBay, Craig, NextDoor, FB Market) quickly, and streamline your fulfillment to the point where it's easy and fun and worth it even for the flow of a few bucks here and there. I was once eBay-phobic, but I've made it so efficient that it's now a delight. For details, see my previous posting, "Making eBay Efficient and Fun".
Give lots of gifts.
But don't waste much time hunting for charity solutions. Everyone's rich now. Nobody wants your old shirts. You can donate books to the library, but the "normal" titles will be sold in annual sales for pennies, while the really cool and interesting ones will almost certainly wind up in the trash. Maybe .5% of books are worth something and have a chance of connecting with a buyer. If no one wants to buy it, no one wants to own it. So if you can't sell or gift a book, trash it. Any other solution is just a conscience-salving intermediary step to trashing. (Caveat: if it's something that a typical 15-25 year old might read, maybe find a library in a rough area that might accept the donation, but they will not make proper use of your Shanghai soup dumpling cookbook or anything else "weird". Only stupid books are widely useful.
Photograph anything you hate to let go of.
This is how you push past the tipping point on mementos and curiosities you want to remember but don't need to display or keep close. Tell yourself you're photographing it so you can remember, but really photograph it so you can let go.
Then blithely chuck what's left.
"When in doubt, throw it out." That's your Johnnie Cochran money line. Use it early and often. You don’t need to justify trashing it. Flip that and try to justify keeping it.
Everyone starts out by pricing garbage containers and other industrial-strength solutions. That may be right for some people, but you're likely not to produce that scale of garbage so fast. Try putting it out incrementally with the garbage. If this backlogs you with many large trash bags (I use these for this purpose, because they don't puncture easily and they're unscented) perennially awaiting the next trash day, ok, pursue sturdier solutions.
Before you start, here's a framing: how much would it be worth it for you, in dollars, to get this done? Probably a few grand, if you're honest. Make that your reverse budget; the amount you're willing to waste to get this done. You may need one of those five clipboards - or felt stick-on furniture gliders, or light switch wall plates - one day! If you throw them out, you might need to re-buy them! Well, if/when that day arrives, the money you spend will draw from the reverse budget. Accept that you might waste $XXXX at some indeterminate future date rebuying items you imprudently throw away today. As you toss those things in the trash, make a mental note of it. And notice how satisfying it is to trash more and more stuff. It’s worth a lot!
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