The Dark Side of Decluttering: Have You Ever Regretted Getting Rid of Something?

We talk about getting rid of stuff all the time and laud the benefits of getting more and more things out of our homes. Freedom! Negative space! Less to clean and organize! While these are all most definitely positive effects of shedding excess, it’s possible that in our maybe-too-hasty pursuit of an ideal that may or may not be your own, we have some casualties, we lose things forever at our own hand and then feel the pang of missing them.

For a few years after college, I had a small storage unit in San Francisco. My grandmother had passed away, and the things I (and my mother) had kept from my childhood and from my college years could no longer be stored in her basement. In the emotional fog of losing someone I loved, I had to sort through my saved belongings, and not all of my decisions were good ones. I tossed things in an effort to not be bogged down, but then made keep-this choices that still make me scratch my head in disbelief.

Those ill-kept things were stashed in a tiny storage unit owned by a local family and operated by a cantankerous man who made you consider just leaving all your stuff in storage so you didn’t have to face him. I was spending $40 a month (when I was pulling in hardly any money) to hang on to things that I either could have replaced when I needed them (I paid to store a mattress!) or had no clue if I’d even really want down the road. I was buying time to decide, I guess, if the things from my past had a place in my unknown future.

Three years (and almost $1500 later), I found myself about to get married and move across the country to Atlanta. It was time to purge that unit and see what was worth paying for to move.

At this point, all the stuff was almost imbued with a sense of importance because it had been “waiting for me.” Luckily, and with the help of a very sensible friend, I was able to cut through this particular line of sentimental nonsense and recycle the boxes and boxes of New Yorker magazines I had in there. It turned out it was worth putting the mattress on the moving truck to Georgia, but so much of the things I couldn’t let go of at first turned out to have no place in the new life I was starting and… I got rid of most of it.

Here’s the crazy thing: The things that, years later, and to this day, I regret tossing aren’t things that I kept in that storage unit; they’re things I got rid of before they even made it into storage. Inexplicably, I miss my high school translations of Latin poetry. And I miss my elementary school yearbooks. Those two, very specific things.

More recently, I regret apparently tossing a magazine page depicting a ring I fell in love with when I was fifteen. My husband and I just celebrated our tenth anniversary, and he gave me a ring we had made based off of that ring’s design. I found images of it online, but I would have been thrilled to find that original page, torn out with my wistful teenage hands, in the bin of memorabilia in my garage.

Are there things I saved that I’d miss if I had tossed them then? For sure. Hand-written notes from my older relatives come to mind. Are there things I carted across the country that I subsequently got rid of? Absolutely. My diaries, for one. (Lest anyone be horrified, it most certainly did not spark joy to read them and, frankly, I didn’t want my kids ever reading them. While the act of writing was probably healthy at the time, recycling them felt goooood.)

So how do we know what to keep and what to get rid of, particularly when it comes to the sentimental stuff? How do we keep what’s important without hoarding junk that overshadows what will remain truly valuable to us? How do we make objective decisions about sentimental things when our subjective responses to them fluctuate?

Ultimately, does it really matter that I don’t have my yearbooks or Latin poetry translations? Of course not. But I want my little twinges of regret to inform my decision-making. How I decide now for a future self is something I’m still thinking about. If you know the secret, I’d love to learn.