I had been dreading this moment, although I was unsure why. In fact, I’d forgotten what I would find inside the boxes. I just knew they had been there all this time, taking up physical and mental space — like uninvited guests at a party.
I stood there for a while, feeling the cold basement floor beneath my feet, facing the boxes. It felt like a Wild West showdown. The heat of anticipation brought feelings to a boil. Nostalgia, regret, and remorse bubbled to the surface.
I took a deep breath.
Then, I began.
What Minimalists Get Wrong About Sentimental Items
Until that point, I had studied and applied minimalism for several years, but I had never actively decluttered sentimental items. Mostly because I never saw any valid reason. For me, minimalism isn’t necessarily about owning less. It’s more about the intentional curation of belongings. This includes eliminating non-essential stuff, sure — but also keeping things that fertilize beauty, appreciation, and gratitude.
In this sense, a case could be made that sentimental items are necessary: they symbolize values, capsulize memories, and tell life stories.
And yet, when I searched for a guideline on dealing with sentimental clutter, I was confronted with conflicting advice. For many minimalists, it seems oh-so-clear that you should declutter all of your sentimental items. It’s a logical step in the decluttering process. And so, without much reasoning, they jump straight into 7 effective ways to clear out sentimental clutter.
I wasn’t convinced.
For one, this type of advice propagates mindless downsizing — as in: decluttering just for the sake of decluttering. At worst, this bulldozer method can lead to an unwanted sanitization of your life — an environment devoid of inspiration, emotion, and art.
Second, and more importantly, these purist guides evade a far more important question. And that question is: Why? Why should we declutter sentimental items in the first place? As in: what might we achieve by decluttering sentimental items?
I wanted to find out. Which brings us back to my showdown with three boxes of sentimental clutter. Unexpected consequences ensued.
Box 1: What-if Reminders
The first box held my stuff from twelve years of school.
On top rested a folder with drawings and paintings — a decade of art classes. In a knee-jerk reaction, I was reminded of my art teacher’s advice on the last day of high school. “You have a gift, you know,” he told me. “Ever thought about studying art or architecture?”
Unsure what to do with this memory or the pictures, I put them aside and dug deeper.
Here were my applications for study programs in engineering. (Five rejections, one acceptance.) Here were the prototypes of a board game I created with a few friends in eleventh grade. (We called it Greedy Pirates, but it never set sail.) Here was a questionnaire for job orientation. (I skimmed the creativity section, where I answered most questions — like: “I enjoy coming up with ideas” — with “strongly disagree.”)
I got lost in these memories like a kid in a colossal candy store. My 18-year-old self came back alive — and with it, all the doors that had been open to me then. I started plotting what would’ve happened if I had, in fact, studied architecture. Or if that one successful application for my engineering degree had been a rejection. Or if we had released Greedy Pirates into open waters.
Going through all these sentimental items imprisoned me in an alternate reality. They made me question my decisions, my career, my sanity.
But eventually, it struck me.
All these things didn’t actually happen. I went down a different path. And at the time, I must’ve had very good reasons for my choices.
Sentimental items can give the illusion that something is wrong with our lives. That we need to hit rewind and rewire our entire string of decisions. But who says life would’ve turned out better that way? Perhaps there’s not as much wrong with our current version of life as we thought.
The entire box went to the recycling bin.
Box 2: Sentimental Souvenirs
The second box was much smaller than the first one and held souvenirs. I would’ve preferred to keep them on my shelf all these years. But after high school, I moved all over the place — often with lean luggage and little patience. And so, the souvenirs landed in a box. In a basement.
I can’t tell you why I had amassed so many souvenirs in the first place. But it had something to do with luck. And vanity. And attachment.
See, growing up, my parents took me to many places: from Portugal to Greece to Hawai’i. Not just that: I also received enough pocket money to buy a souvenir from each place we visited. And so, I found myself digging through a treasure chest of trinkets: there was a knight figure, a small lighthouse, a tiny totem, colorful stones, and more.
These things felt like screw-top jars full of memories.
If I got rid of these, I thought, I would lose all my memories of these trips. It would be inadequate. And ungrateful, too. But then I paused. Did these souvenirs really contain memories or gratitude? As I pondered this, I couldn’t even remember the exact day or place I bought these items. And besides: if the memory was truly valuable, why would I need a mass-produced piece of plastic as a reminder?
I was tempted to put all the pretty souvenirs back in the box where they would be safe — sealed away from the world like a time capsule. But then I realized this would start an infinite loop of absurdity. A few years later, I would reopen the box, look at the souvenirs, and put them back again. Then, some years after that, I would do the same: open, look, put back. The cycle would start anew. And I would get stuck in it like Bill Murray in Groundhog Day.
Reluctantly, I recycled what could be recycled and donated what could be donated. There was this one moment of pure guilt in which I thought, “I imported these items from all over the world just to get rid of them. I’m a terrible person.” But the truth was, these souvenirs were better off in any other place than this dusty basement box.
The hidden beauty occurred to me as I was folding the emptied box into a carton sandwich: Letting go of these souvenirs actually made them more valuable. Paradoxically, the singular parting moment beat the countless times of glancing at these souvenirs on my shelf. It was much like saying farewell to a good friend: it’s an emotional power punch, but for the first time, you can truly appreciate and reflect on the shared memories.
Impermanence catalyzes gratitude.
Box 3: Gifts from Childhood
The third box, at last, was full of various childhood memories.
On top was a pile of cards and letters. From “Happy Birthday!” to “Merry Christmas!” to “Greetings from France!” — there was a card for every occasion. I considered this for a moment and mulled over the time it took for this pile to exist. Picking a card, thinking about what to say, writing the card, stamping it, bringing it to a mailbox — several people had done all this over several years on several occasions.
Awe-inspiring and humbling.
But another pair of items was particularly tricky: A Peanuts DVD collection and a Peanuts calendar. My dad gifted them to me when I tore my ACL at age 11 and was bound to a hospital bed for weeks. I remember watching one episode where Snoopy breaks his leg and gets furious about his cast. I could relate.
But it was a fickle memory. Much like re-remembering a dream long after waking up.
This was because I had completely forgotten that most of these things existed. Someone could’ve trashed this box, and I wouldn’t have noticed all these years. But now that these items had been unearthed and brought to light again, I started clinging to them as if they were holy water in a scorched desert.
The fact that these items were gifts played a role here. After all, getting rid of gifts can feel like the epitome of ungratefulness: someone else spent time and money on you, but you decide to throw it all away.
How dare you?
But wait a minute. What are gifts actually about? Isn’t it that gifts are less about the physical item and more about the gesture, the act of kindness? I, for one, used to think that gifts must serve a lifetime of utility. That they have to linger in drawers and cupboards until I forget their origin. But maybe they’re more like lottery tickets: one-time consumables. Once we redeem their prize, it’s okay to let go of the ticket. (Often, the prize lies in the sweet moment of unwrapping.)
And so, I discarded the letters, scanning the most meaningful ones with my phone. As with the souvenirs, this act of letting go cherished their existence rather than diminishing it.
The Peanuts DVD collection was a tricky one. I put it for sale on a second-hand marketplace — with a baffling result. While most other items I sold on this platform didn’t pay more than a few cents, this DVD collection was about to bring in a whopping $35. I hesitated. Wanted to hold on. Perhaps it’s a collectible? Maybe I can get more money for it somewhere else? Maybe I should keep it after all?
But I had to be honest with myself: I would’ve given that DVD collection away for free if I hadn’t known the price tag. Someone else needed it more than I did. Perhaps a dad who wanted to give it to his injured son.
Ultimately, many sentimental items are much more valuable when we free them from the shackles of our nostalgia and pass them on to a new owner. And with that, give them a new life, a new purpose.
3 Rules for Decluttering Sentimental Items (and One Surprising Lesson)
Is decluttering sentimental items worth it? Well, only you can decide.
It’s a confrontation with your past and, thus, a personal and finicky affair. Besides, there’s nothing wrong with keeping lots of sentimental items. I still shamelessly cling to things like diaries, books, and entrance tickets. And I enjoy them. They add meaning to my life. However, when a sentimental item falls into the category of these boxes, I know that letting it go could help me flourish. Here are the three rules I learned:
- Trinkets of regret — Do sentimental items only remind you of the person you could’ve been rather than the person you could be from now on? Letting go might help reduce regret and make space to grow.
- Time capsules of absurdity — Do you find yourself returning to certain sentimental items, but they never challenge or inspire you? Do they trap you in a time loop of inaction? Chances are, the one act of letting go will help you appreciate these items much more than constantly revisiting them.
- Blank gifts — Are you holding on to gifts because you want to or because you think you have to? It’s okay to let go of gifts if they don’t serve a purpose in your life anymore. Instead of fixating on your own loss, consider the joy the item could bring to a new owner.
But there was something else I learned. Something unexpected.
Looking back, it wasn’t really the process of decluttering that felt cleansing. Rather, it was the process of writing about it. Reflecting on it.
The thing is, getting rid of sentimental items creates dissonance: your emotional side wants to hold on, while your rational side wants to let go. Now, you can try to crowbar your emotional side into alignment by decluttering lots of stuff — conviction through overwhelm. Or, like a mental archeologist, you can excavate the emotional logic behind letting go. By writing about it, for example.
Strangely, our life stories and sentimental belongings make a lot more sense when we package them into paragraphs and punctuation. This also lessens the attachment to physical belongings.
In fact, decluttering sentimental items is much like editing. “Kill your darlings” echoes the time-tested writing advice. Which, of course, doesn’t mean you should obliterate every line you’ve ever written. You don’t want to end up with a blank page. It’s more about assassinating the tiny phrases that seem pretty to you, but in reality, they ruin your piece.
Similarly, the point isn’t to declutter every last one of your sentimental items. Heck, maybe the point isn’t even to declutter. Maybe the point is to grasp sentimental items — their memories and meanings.
Yes, maybe the point is to proofread and edit the past tense of your life story — so you can continue writing it in the present tense.