I used to be a pack-rat, and in a horrible way. I would save programs that had my name on them, not because the event was special, but just because the piece of paper had my name on it. When I moved out on my own for real (to an apartment, not just a college dorm), I decided that I wanted to have all my stuff in my house with me. Then I realized how much stuff I had, and spent a month getting rid of a lot of it.
This first round of simplifying and decluttering was easy; there were tons of books I didn't particularly like, clothes I didn't wear or attach sentimental value to, and slips of paper with my name on them that I could get rid of with ease. I got rid of a third of my stuff with no guilt at all, and moved the rest over to my tiny apartment.
Over the next few years I was able to slowly go through a box at a time and downsize my collections. I religiously read unclutterer.com to keep myself motivated and inspired. Occasionally if I had fond memories of something but didn't need it in physical form I would take a picture of it. My Scottie dog sweater from second grade makes me smile, but I get just as much happiness from looking at a picture of it as I do from holding it, so I donated the sweater and kept the picture, which takes up no space at all on my hard drive. This picture taking habit served as a useful crutch, and I was steadily making my way towards a streamlined household that only contained things I loved, used, and could store and care for in a respectful manner.
Then I got evicted. It happened with little warning, when I had no safety net, and for reasons that had very little to do with my qualities as a tenant. My apartment was the first real home I had made for myself, and losing it hurt. A lot. Worse, compounding my problem of having no money, no place to live, and very little time to solve both of these problems, was the fact that I still had boxes of stuff left to evaluate.
With everything happening at once I got rid of stuff. A lot of stuff. I opened all the boxes before I donated them, but that was about it. I panicked, and made a bad situation worse by getting rid of stuff that I used and loved. Moving from a hundred and fifty square feet of apartment to fifty square feet of storage unit and whatever could fit in my car made me freak out and get rid of clothes, books, and project materials that I wasn't really ready to part with.
In an effort to clear out my life's problems, I made a list of everything I needed to live. A tiny wardrobe, a few cooking necessities, and the barest bones of hobby material. Artwork, fun-but-impractical clothing, childhood treasures; none of these things made the list, and so a lot of them got donated. My bright orange coat that made me look like a pumpkin when I wore it was donated, despite the fact that I loved wearing it, and was even designing a leaf hat to enhance the pumpkin look. A juicer that I didn't use on a daily basis was listed on freecycle, even though I was steadily increasing my juicing efforts. A typing table that was tiny but faithfully useful was given away, even though it left me with no place to write.
After the purge, when I had finally settled with my fiance at his parents' house, I started to feel guilty and remorseful. Yes, I got rid of some stuff that I would have gotten rid of anyway, and the fact that I managed to take time to donate or recycle everything brought me some comfort, but the fact of the matter was I'd gotten rid of too much too fast. My anxiety and depression turn this into a worse problem than it actually is, but the crappy situation of losing things that were useful and loved remains.
And here is where this post falls apart, because here is where I am right now. I have a lot less stuff, but now the worry of not having it is replacing the worry of having it. I'm slowly beginning to realize that it was never about the stuff in the first place. I'm worrying because I still really don't have a home, years of work to improve my life was blown to hell in less than a month, and things that enhanced and improved my life are now gone. I can (and do) replace some of the best things on e-bay (let's just say I'm knitting myself a green leaf hat for winter), and the rest I'm starting to realize wasn't that important to begin with. Sure, my Chi hair straightener will cost a lot to replace, but the likely-hood that I'll ever need to do that is small, since I wear my hair short now. And in the case of sentimental objects, I try to remember that releasing them back into the universe to give others joy is a lot better than losing them in a natural disaster, or even than letting them molder away quietly in a box sealed for safekeeping.
If I could do it all over again, I'd definitely do things differently, but I'm living well now with what I have, I'm doing well replacing gnawing guilt with simple regret, and I'm learning to love myself regardless of what I own or what bad decisions I've made. Plus, I'll always have pictures of my favorite dinosaur friends.