Kim Allen doesn’t like clutter. But when it comes to some of her most sentimental items, she finds it hard to let go.

Near the top of the list is a ceramic creature that her daughter made years ago. It has one eye, a lolling tongue and a crop of blue hair. She displays it in a prominent place near her bathroom sink because it always makes her smile.

But there are other keepsakes that don’t bring the same kind of joy — such as memorabilia and artwork handed down from her relatives — that are only taking up space, physically and emotionally.

“Hopefully I will be retiring at age 67,” said Ms. Allen, who is 52 and lives in Sherrill, N.Y. “Do I really want to deal with all of this excess stuff then? No, I want to be having fun with my friends and family, enjoying the life I worked so hard to build.”

And yet for a long time, Ms. Allen felt uneasy about discarding the family heirlooms.

Sentimental items are among the hardest belongings to part with. The mementos can feel intertwined in our identity, particularly if they once provided us comfort or belonged to a loved one. Getting rid of them can signal that certain chapters of our lives have closed, said Selena Jones, a grief and trauma therapist in Ontario who coaches older adults in the art of decluttering.

“People get caught up in the fear that if they let something go that is sentimental, that they will forget the memory,” she said. But our memories live inside us, she added, not in our things.

If you’re looking to pare down some of your most meaningful items, here are gentle ways to get started from decluttering experts.

Build Your Decluttering ‘Muscle’

To kick off the process, reflect on why you want to declutter in the first place, said Dr. Carolyn Rodriguez, an expert in hoarding disorder and a professor of psychiatry and behavioral sciences at Stanford Medicine.

The “why” will serve as your motivation. For example, maybe you want to avoid leaving behind a slew of items for your children to sort through after you’ve died. Maybe you simply want a room or space to be more functional.

For Lee Shuer, 50, who lives with symptoms of hoarding disorder, making the choice to trim back his sentimental items was an enormous challenge at first.

His drive to collect things began in childhood. When he got his own space, stuff filled his home in Northampton, Mass., spilling onto the porch and choking the hallways. He eventually realized that he was clinging to things that reminded him of people, places and experiences from his past.

“I wanted to make room for my future,” Mr. Shuer said. He envisioned having a space that would be welcoming for friends, family and, eventually, a romantic partner. Now, he helps people declutter their homes, and leads workshops, which he helped develop, for those with hoarding disorder.

Once your motivation becomes clear, Dr. Rodriguez advises tackling the low-hanging fruit: the common areas that you use every day.

By focusing on decluttering the living room and the bathroom, for example, your efforts will be immediately visible and rewarding, Dr. Rodriguez said.

Then work your way up to the items that feel the toughest to discard.

Prioritize the Items That ‘Amplify Joy’

After his mother died, Joshua Fields Millburn, a host of the podcast “The Minimalists,” learned that the fewer sentimental items he had, the more value he got out of them.

“Because if everything’s sentimental, then nothing’s sentimental,” he said.

So rather than putting everything in a “clutter mausoleum,” he said, choose the few things that amplify your joy and consider displaying them, he advised.

Also ask yourself whether you would pay money for any given item again. If not, that’s a sign you should let it go, Mr. Millburn said. If you think you might want to look at it again, consider taking a picture and storing it in the cloud or a special folder in your computer.

Ms. Allen, who has managed to whittle down some of her more sentimental items, faced a tougher challenge when considering her deceased relatives’ hand-me-downs — but eventually she had to admit that she and her daughter didn’t want them.

At first, this made her feel guilty.

Emotions like this “keep us stuck, and it can lead to procrastination,” she said.

Do a Little at a Time, but Do It Consistently

To avoid becoming overwhelmed, Ms. Jones suggested making your task as small as possible. You might pick one room; one type of item, like a big stack of paper; or a pocket of time, such as every Saturday at 3 p.m. Then stick with it. Even if you only spend 10 minutes at a time decluttering, you’ll see progress.

Susan Litt, 49, in Richmond, Va., is continually sorting through the artwork that accumulated from her two children. “You can’t have 10 bins of things for your kids,” she said. “It’s overwhelming.”

Now that her children are teenagers, she asks for their input on what holds meaning and what can go. She also avoids trying to sort everything in one sitting — “that’s too drastic for me,” she said. Instead, she’ll return to the same pile of things in a few months.

Try These Decision-Making Techniques

If you’re not sure where to start, Dr. Rodriguez suggested, pick up an item and ask yourself two questions: 1) What comes to mind when you hold this item? 2) What if you got rid of it?

It’s often helpful to share your answers with a friend or family member, Dr. Rodriguez added. Simply talking about the item and the time period that it represents can sometimes help people let go, she added.

You can also ask a friend or neighbor to hold onto something you are considering parting with for a week, Mr. Shuer suggested. Then see how you feel when the week is up. Was it as difficult as you anticipated?

Steve Wobrak, 67, of Latrobe, Pa., said this strategy helped him to finally give away one of his daughter’s many elephant figurines — years after she died.

“I got some tears out,” he said. Parting with one sentimental item made getting rid of others a bit easier. He soon realized that the memories didn’t disappear, even if the items did.

“It’s OK to have emotional attachments,” Dr. Rodriguez said. “You just can’t keep all of the things.”