If you know me, you know that I’ve moved A LOT. By my count, I’ve received mail at 19 addresses since I moved out of my parents’ house in 1997.  Given that I’ve moved at least once a year for most of my 20s and 30s, it really is shocking the amount of stuff I have.

Over the last few months, I’ve been starting the process of downsizing in anticipation of yet another (in town) move, this time with someone with a significantly more minimalist lifestyle. I’ve identified things of value that I can sell, many of which I’ve been moving around with me for up to 10 years despite less than annual use. I’ve been setting aside books for his neighborhood’s Little Free Library, and have been mending, donating, or tossing clothes that no longer work for me. Today I gave my roommate my vintage find of 2012: several boxes of mint condition nylons from the 40s that were incredibly cheap, but could only fit me if I removed several inches of my femurs. No point in keeping pretty things in a box.

Inspired by 10 Excuses We Make To Keep Our Clutter, I’ve decided to take on my biggest challenge: nostalgia. Since moving out, I’ve hauled with me several boxes of letters, photos, and other memorabilia.  As a lifelong letter-writer and creature of extreme sentimentality, I have a hard time tossing anything of emotional value, and have never figured out a good way to decide what stays and what goes. Every so often, I’ll figure out a way to weed some of the stuff, but that doesn’t stop the flow of stuff INTO the boxes.

After recycling a few things last night, I sorted out a small shopping bag full of letters for scanning. The particularly precious letters – like those from my grandparents – will go back into storage, but many will likely be recycled. I’m not sure what my process will look like exactly, but I’ve been using that as an excuse for years, and so decided to start with the less precious items while I figure out a sustainable and durable process for the rest.

This post about Digitizing Old Letters suggests a potentially useful workflow: scanning letters into Evernote, using OCR to translate as much as possible to searchable text, and transcribing the rest. I’ve been trying to figure out how to incorporate Flickr into my process, particularly for friends who send mail art. I’m limited by what I can do on the cheap – using the scanners we make available to patrons at work – but that’s better than nothing.

I would love your advice if you’ve tackled this challenge for yourself – or if you’re a pro who digitizes and stores things for a living. And I will report back here as I figure out a process that works for me now, and for a future sentimental me who wants to revisit the correspondence of her youth.