Part of me living my life backwards has been about doing what Ciji Ware's excellent and comprehensive book, Rightsizing Your Life: Simplifying Your Surroundings While Keeping What Matters Most, discusses in detail: figuring out what works and why, and finding ways to let go of the rest.
It's the right prescriptive for People of a Certain Age (middle) who are headed into a new age (old), and that's who this book is written for. Aside from the general resistance to change, we are tremendously attached to our stuff here in the U.S., and by our personal mid-century marks, we tend to have accumulated quite a bit of it. As has been pointed out for eons, you can't take the stuff with you when you go; as people find when they're either forced by circumstances or drawn by new desires (fewer stairs, less dusting, more oceanfront), you can't fit it all into a beach condo, either. Plus, there's the dusting.
I love stuff as much as the next guy, but I've come to understand that, regardless of the cost of acquiring it, the price of having it is freedom. You don't really own your stuff, by definition, you can't. You're only renting. But your stuff can definitely own you, and does, when you silently agree to be the caretaker of stuff that no longer serves. (There's also the issue of acquiring stuff that never really served, or that served only to distract you from that big, empty hole inside you, but that's beyond the scope of this piece.)
The sweeping concept of this book is simple: as you move through the various stages of your life, stay awake to your needs and wants, and keep only what serves. If you can absorb the full meaning of that line and figure out the rest for yourself, godspeed. If not, Ware's book is filled with practical information about how to determine what's serving, as well as detailed information about the proper disposal of what's not. There are sections on editing down everything from wardrobe to cookware to photos, plus resources for help with physical removal of stuff. There are ways of doing it on the cheap or the medium or the high end. There are timelines and how-tos for people with the luxury of time, and those with change breathing down their necks. There's discussion on how to handle the move and, should you need to, handling another move. (Apparently, this happens more than you might think: sometimes life intervenes swiftly, and other times the downsizing bug really takes hold.)
Ware is a seasoned journalist, and it shows in the finished project. Rightsizing Your Life is a complete how-to manual, a great all-in-one reference guide, with the luxurious added bonus of being (hallelujah!) well written. It's a couple of years old, publishing date is 2007, but it's sadly timely, in light of the forced "rightsizing" a lot of people are finding themselves in with this difficult economy.
If you're facing a move and feeling overwhelm at the mere thought of it, or simply a logical Virgo type who likes the idea of a companionable checklist of sorts, this book is for you.
UPDATE: I should perhaps make it crystal clear that the primary audience for this book is the person or family of relative means, "rightsizing" to a simpler lifestyle that is still fueled by relative means. In other words, the American upper-middle class. If you're in doubt as to whether it's the right book for you, I'd encourage you to check out a copy from the library, browse it in the bookstore or just read the reviews on Amazon.com, which are pretty accurate.
Rightsizing Your Life: Simplifying Your Surroundings While Keeping What Matters Most, by Ciji Ware (Springboard, 2007)