I'm coming to believe one of the hallmarks of functional adulthood is learning how to throw things out and not regret it. This is not as difficult as it seems. Learning to do this is one of the most personally liberating and empowering things you will ever have.
When I first started publishing as Genji Press (the precursor to Infinimata; many of the older books were republished under the new label), I lived in a wretched four-bedroom split-level that had the advantage of being in a very nice, walkable neighborhood. I used one bedroom as an office, and it was a shambolic mess of such proportions I don't know to this day how I could even sit down in it, let alone get anything done there. I had a giant workstation with two monitors, tons of toys in diorama cases, and five bookcases arranged in such a way that they turned the interior of the room into a rabbit warren. Plus a closet jammed with paperbacks and boxes of other bric-a-brac. Plus end tables repurposed along a wall for more storage. It was, I told myself, a friendly mess; a symptom of a lively, active imagination.
It took a long time to realize I hated living like this, that I had always hated it, that I had clung to this because I thought it was "who I was", and that I had simply ended up loving it out of no other way to deal with it. That mess only looked like my friend. All it really did was rob me of the ability to triage my life. Marie Kondo was right: none of this sparked joy.
All that changed when we sold our house and moved. Moving is expensive, and the less we took with us, the better. We discarded, I think, a good three-fourths of what we owned. We took no furniture, since we were just going to buy new stuff in the new place.
What surprised me was how easy it was to start letting stuff go once we got the wheel turning. Once I started actually separating things, I tried a trick I'd learned from someone else once: the default should be to let something go. I would ask myself: 1) When was the last time I interacted with this thing in any way? and 2) What were the conditions of the interaction? If the last time I interacted with it was a year ago, to take it down from the shelf and move it around because I was running out of room, then that was a good sign I wasn't going to miss it. I let got of a lot of things this way, without blinking.
If you're really, really torn about something — so much so that you end up stalling the process for minutes at a time — set it aside and come back to it. But again, if you encounter something that you know you touch and use daily, keep it. (Just glancing at it on the shelf doesn't count.)
So once the wheel got turning, I let go of a lot, and I did it without blinking. I think of all the things I let go, I only regret letting go of maybe two or three specific things, and even now I can't think of what they are. I just remember the tinge of regret. But if I can't even remember what that regret was attached to, then I suspect it wasn't important.
Most people I know of get hung up on things that have sentimental value. For this I had to be doubly vigilant: What was the sentiment, and why did I value it? I have many photos of my family, but my two absolute favorites, one of my wife on the phone and another of my parents at their wedding, are the only ones I keep right at hand. The rest can live in a box or on a hard drive.
What I came to understand, after much sifting, was that not all sentiment is positive or constructive; sometimes we hang onto things because we think we are obliged to remember them, or because we fear no one else will remember them. Sometimes we are right, but it's too easy to believe these things reflexively. We feel we are the appointed dream-keeper for that particular dream. We worry that a life without the furniture of such memories in it will be a mere empty room. But I wonder how true this is, and what benefit it really has for us. The more sincere you are with yourself, the easier it is to see that the number of things you can be truly sentimental about is very small indeed. Maybe a shoebox or two, in my case.
After we resettled, my office (a 12'×12' room) consisted of a single L-shaped desk, a three-drawer filing cabinet, a smaller rollaround cabinet that tucked under the desk, two small shelves affixed over the desk, and three IKEA Billy bookcases, two with glass doors. After we recently moved again (a short distance, just across town), I kept most of that arrangement. But in both cases, I'd become newly vigilant about what was worth keeping.
One significant change was this: I didn't give myself a lot of opportunities to hang onto stuff, or places to squirrel it away. The little shelves were for storing immediate-use things. The filing cabinet never stored more than a year's worth of papers. (I got into the habit of keeping digital copies of things, and transitioning to paperless for my bill-paying.) And if the bookcases got full, I would have to pull them apart and find things to let go of.
A lot of what I let go of during that time was highly specialized material that I had to be honest with myself about how often I was going to use it or to what end. I didn't own it because I actually cared about the subject, but because I wanted to act like I did, and that the longer I lived, the more I saw there were not that many opportunities for me to care about them in a constructive way. All they did was sit on a shelf and wink at me, so to speak. They were not "me". They were not even some aspect of "me" that actually existed. They were just some idea I had of "me", an idea that had no reality save for whatever I maintained in my shabby little room.
I also developed another good heuristic for what to keep, physically. If I could find a digital edition of something at a decent price, and the presentation for the item was not a concern (e.g., not an artbook), I'd get the digital edition and ditch the physical one. That freed up room generally, but also freed up room for things that could not exist as anything but a book on a shelf! This part I've talked about before, but I grow more appreciative of it with time. It gives you more opportunities to figure out what's actually important, and what's just symbolic.
What all this helped clear up for me, though, and give me a standard going forward, was that I did not want to make any more excuses for living in the middle of a landslide of personal possessions. I didn't want to pretend I cared about things I actually didn't care all that much about, because the dimensions of my life no longer supported such care. I didn't enjoy hauling (figuratively, literally) the weight of so many things that were supposed to be "me", but really were more just reflections of some idea of myself that had no substance. Maintaining the weight of such a charade was depressing. Realizing I didn't have to do that anymore was liberating.