Why Do We Find It So Hard to Throw Away Things From Our Past?

At the back of my wardrobe is a box full of memories — people, places and versions of myself I haven’t quite been able to let go of. Inside are letters, a single red rose from an ex, birthday cards, paper concert tickets and boarding passes from before everything went digital. There are old journals, too, and the obituaries of two people I loved: my best friend, who died more than 20 years ago, and my grandmother, my Oma.

When I moved from Canada to London in 2019, these were among the few possessions I chose to bring with me. Everything else stayed at my parents’ house. I open the box when I’m homesick or want to remind myself how far I’ve come. An old letter makes me wonder about someone I haven’t spoken to in years; a journal entry makes me feel protective of the younger woman who wrote it. The things I’ve collected since moving to London remind me of the relationships and experiences I might never have had if I hadn’t taken the risk of starting again.

These things are important reminders, yet we’re often encouraged to declutter our homes, delete our exes’ numbers and make room for the next chapter. From minimalist living to the endless pursuit of self-improvement, we are sold the idea that becoming someone new means shedding everything associated with who we used to be. But what if, somewhere between clearing out our homes and reinventing our identities, we’ve confused letting go with pretending something never mattered?

Our attachment to possessions isn’t necessarily about the objects themselves, explains counsellor Julie Shehata-Morgan. “Belongings can act as external reminders, while also supporting an internal emotional world. Mementos and memories can help, but their meaning can change as time goes by. They can be a comfort at one point and later become a burden.”

Sometimes, Shehata-Morgan explains, holding onto possessions can be a sign that we haven’t fully processed a transition. But that isn’t always the case. “We don’t need to discard something meaningful simply to demonstrate that we’ve moved on.”

I know this to be true because one of the most meaningful things in my box is the obituary of my best friend. When Chantelle passed away, I found myself clinging to anything that made me feel close to her. I kept the obituary because in the aftermath of her death, I felt like I had so little to hold on to. I wanted to preserve every piece of her I could, and having something physical that belonged to that moment in time gave me a sense of connection to her.

For decades, I struggled to accept her death. It took years of therapy, and Eye Movement Desensitisation and Reprocessing (EMDR), before I could look at the obituary and truly see it as a celebration of her life. The words on the page hadn’t changed. I had. Once a painful reminder of everything I’d lost, it’s now something I treasure as a tangible connection to her.

I still miss my friend, but now I think about the person she was rather than just the fact that she’s gone. I haven’t stopped grieving, but instead, found a different way to remember her. An object can hold grief and love at the same time, and its meaning can change as we do.

Shehata-Morgan says people can be hurried through grief by the pace of everyday life and the expectation that they should move forward. But grief doesn’t follow a schedule and neither does our relationship with the things that remind us of what we’ve lost.

For Marissa Field, moving on involved a funeral of sorts. After her mastectomy, she held a ‘bra funeral’ with her friends, ceremonially saying goodbye to the bras that belonged to her pre-surgery body. Secretly, she held onto her favourite one.

Surrounded by friends, she had gone through the ritual of letting go, and yet one small piece of her former life remained tucked away. Before cancer, the bra had been part of her everyday life… afterwards, it became a reminder of the body she had lost and the woman she had been. “Our bodies are incredible testaments to our strength and I want to remember the woman I was while also recognising how much I’ve overcome, physically and mentally,” she says.

Not every keepsake carries the weight of grief. Harriet Smith tells me that she keeps every love letter she’s received and still sleeps in her ex’s T-shirt. She can treasure the memories, she says, without wanting the relationship back. Emily Ferbey, meanwhile, has bought the same candle for every home she’s lived in, creating a sense of continuity through different countries and chapters of life.

The meaning we attach to possessions isn’t always obvious from the outside. What looks like an inability to let go might instead be a way of preserving a connection to a person, a place or a former version of ourselves. Family photographs and inherited belongings can also preserve stories for the next generation. However, an object alone can’t tell us whether an attachment is meaningful or holding us back.

Rather than asking whether we should keep something, Shehata-Morgan suggests considering what it brings up, how we’d feel without it and whether it still serves us.

Objects can offer comfort and connection, but they can also become a psychological burden, their very presence keeping us tethered to painful memories, unresolved emotions or relationships we’re struggling to move on from.

I don’t keep my box because I want my old life back. I keep it because it’s part of the life I have now. The letters from Canada connect me to a place I once called home whilst my London keepsakes remind me that taking a chance opened doors to people and experiences I couldn’t have ever imagined. The obituaries remind me that grief can change shape without love disappearing.

Perhaps the pressure to move on comes from the belief that growth should be visible — in what we discard, the relationships we leave behind and the identities we no longer claim. But not every new chapter requires a clean break. We can outgrow a relationship without pretending it didn’t matter and we can become someone new without erasing who we used to be.

Maybe moving on isn’t about leaving every previous version of ourselves behind, just learning to carry them differently.