The white golf shoes sit on a shelf in my bedroom closet, in a plastic emergency room bag labelled “Personal Belongings”. They’ve resided there for 14 years, since a muggy June day when my 65-year-old dad finished 18 holes of golf. As his friends entered the clubhouse, my father sat on a bench and collapsed from a fatal heart attack.

The shoes, for reasons I no longer recall, wound up in my closet. I rarely think of them until I’m rummaging for something on the shelf and spot the clear bag by a pile of wrinkled T-shirts. I really should get rid of those shoes, I tell myself. And almost instantly I think ... Nope. Can’t do it.

In her Netflix series and bestselling book, The Life-Changing Magic of Tidying Up, Marie Kondo preaches a simple decluttering strategy: if an object doesn’t bring you joy, get rid of it. But what if an object brings you pain? And what if pain is the reason you keep it? Is that unhealthy? Is it normal to keep a 14-year-old symbol of loss? Or just morbid?

I’m hardly alone in clinging to a loved one’s possessions. A friend keeps a tweed hat and scarf that belonged to her father, who died in 1979. “To lose those objects,” she said, “is to lose the connection.”

Another friend, who lost her father 25 years ago, treasures his handkerchief: “It still carries his scent — or maybe I’m imagining it — and the cloth is soft on my cheek. Just like when I was a child and needed to be comforted.”

Yehuda Jacobi, author of the grief memoir Beyond the Opened Door, has kept his mother’s bottle of Chanel No 5 for 19 years. “It is mostly evaporated, but when I smell what little scent is there, it is almost as if she is in the room,” he said.

My dad’s golf shoes do not evoke such pleasant memories. So why keep them? Megan Devine, a psychotherapist in Portland, Oregon, has addressed this question in her own life. In 2009, Devine’s partner drowned, three months before his 40th birthday. The brown T-shirt he wore that day is still in a drawer. “I’ve moved four times,” she said. “It’s not going anywhere.”

Too often, she says, grief is pathologised and treated like an illness. Yet not all pain is bad.

“Those golf shoes are a reminder of what happened,” said Devine, author of It’s OK That You’re Not OK and founder of the company Refuge in Grief. “Sometimes you need evidence that your person lived, evidence that this happened, especially in a culture that wants to erase the person, particularly after a sudden or traumatic death.”

Erase the person? Really? That seems harsh, but when we grieve, we’re often pressured to stop feeling sad and move on with our lives, she says. Remarkably, at her partner’s funeral, people asked Devine when she would start dating again.

“There is a cultural idea that any kind of pain, but especially grief, is something you’re supposed to master quickly,” she said. “And the implication of that cheerleading — Be strong! Push through this! Put the past behind you! — is that if you still miss your person after six weeks, there’s something wrong with you. We don’t talk about grief and pain and sadness as normal, healthy things, so we don’t know how to respond. And when we tell someone, ‘Don’t you think it’s time you’ve moved on?,’ that’s a shaming response based on our own discomfort.”

We also engage in what she calls internalised shame.

“I can hear it in the language you used,” she told me. “‘Isn’t it time I do this? Isn’t this kind of ridiculous?’”

Discarding loved ones’ things can often spur a second round of loss, says Los Angeles decluttering expert Tracy McCubbin, author of Making Space, Clutter Free. “Clients often tell me, when they say goodbye to someone’s stuff, they’re saying goodbye to that person all over again,” she said.

Ironically, our lost loved ones probably don’t expect us to cherish their stuff. Kelli Kehler, the executive editor of DesignSponge.com, lost her father to cancer in 2011 and tells the story of one of his pillows.

“When you have cancer and you have a lot of pain, your comfortable positions become the centre of your life. So this was his special silver pillow,” she said. In the years since his death, her five-year-old daughter had kept the pillow on her bed. One night she got sick, and as Kehler cleaned the mess, she realised the pillow had to go. She felt anxious about it. But she also knew what her father would say: “It’s just a pillow.”

I’m sure my dad would say the same thing about his shoes, but he wore them as he took his last steps on Earth, and those links to final moments carry a powerful, emotional weight.

As time passes, our connection to objects can diminish, as grief counsellor Claire Bidwell Smith has found. When Bidwell Smith was 18, her mother died, followed by her father’s death seven years later. An only child, she experienced despair, depression and anxiety after their deaths.

“As a grief counsellor, I believe that you can never fully be prepared, but I really was not,” she said. “My mom had largely been in denial about how sick she was, which meant that I was also in denial. With my father’s death, it was a double whammy.”

Bidwell Smith kept a variety of her mother’s possessions, including a large ceramic Mexican serving bowl. Two years ago, she broke the bowl while scrubbing it in the sink — and couldn’t bring herself to throw away the pieces.

“It’s like the only proof that she was real, that our time together was real, because it’s so long ago now,” said Bidwell Smith, author of Anxiety: The Missing Stage of Grief. “When these things break, all I see around me are objects from the life I’ve led without her.”

And yet in recent years, as Bidwell Smith and her family have moved to different cities, she has said goodbye to certain objects. “The meaning has dissipated a bit over time,” she said.

She is even ready to relinquish the broken bowl as her family move from California to South Carolina.

In my own case, I think I understand now why I’m so reluctant to give the up the golf shoes. If I give away his shoes, I’m severing a final emotional link to my father’s life. And if I lose that link, it’s like I further lose him. Pain is real. Pain lives on. I can feel it when I see the shoes and the tag on the bag with his name and date of death. I’m not ready to lose that raw reminder. And according to grief experts such as Devine and Bidwell Smith, that’s fine.

As McCubbin said, you have to ask yourself: Why do I value this?

“Maybe every once a while, you need to touch it or smell the leather,” she said. “I know it’s funny coming from the declutter expert, but I don’t think we always have to get rid of something.”

Maybe, Devine suggested, the question is not whether something brings you joy, as Kondo believes, but whether it feels important. For me, the golf shoes still feel important. And so they will continue to sit in my closet, largely forgotten, until I’m again reminded of a special man and a very bad day. And I will welcome the pain.

• Ken Budd is the author of The Voluntourist, a travel memoir