Organizing. and getting rid of, extra belongings can make it easier to downsize, clean a home and entertain guests.

But what should be done with a stack of boxes containing memorabilia stashed in a closet? Or a basement filled with items that represent the past 30 years?

“Clutter is real, and stuff follows us to the end,” says Felice Cohen, author and professional organizer based in New York City who teaches online organization classes to older adults.

“Sentimental clutter is the hardest clutter to part with.”

Sorting through last week’s coupons can be much easier than tackling a bin filled with memories from the past.

“As someone at the beginning of decluttering our large home in preparation for retirement, or at least moving into an apartment, we, like many friends, are dealing with the added, painful issues of what to keep from the home of close relatives who have passed away,” says Joel Poznansky, 61, who lives in Bethesda, Md. “There are questions about items — like overly revealing love letters or divorce papers that raise significant issues — fraught with overwhelming emotions.”

Those emotionally charged items can be tough to evaluate rationally. “Sentimental clutter is the hardest clutter to part with,” Cohen explains.

Strategies for Successful Decluttering

While not painless, approaching a stash or houseful of sentimental things with the following strategies may make the process manageable:

1. Group the memorabilia. “Memorabilia is very overwhelming to deal with, both from a volume and emotional perspective,” says Lisa Dooley, an organizing coach and author of More Space, More Time, More Joy!

To simplify decluttering, gather all keepsakes and mementos and put them in one spot. In addition to the easy-to-find items, empty drawers, closets and other storage areas. “Believe it or not, dealing with it piecemeal is even more time consuming, because we have no idea where it will pop up next,” Dooley explains.

2. Start with what’s easy. After putting it in a pile, don’t tackle everything in one day. Start slowly, such as setting a timer for 15 minutes or half an hour. Take a break and head back to the pile the following day.

You’ll likely spot items that you don’t use or value, such as a broken lamp from your first marriage or stained clothing you don’t remember purchasing. Deal with those first. “If it’s been damaged by water, heat or animals, it is beyond saving,” Dooley notes. “Throw it out now and move on to what you can work with.“

3. Create categories. It’s not unusual for a home’s memorabilia pile to span multiple generations, including everything from antiques to handmade blankets, children’s artwork and an assortment of grammar school yearbooks. Sort the belongings into groups, such as collections, pictures and old documents.

“Classifying items by type provides structure, which decreases the likelihood of becoming too emotionally overwhelmed,” says Sheri McGregor, a life coach and author of Done With the Crying: Help and Healing for Mothers of Estranged Adult Children.

Then, focus your attention on one group at a time. “Going through old photographs is one decluttering category,” McGregor says. “Sorting through a son or daughter’s school mementos is another. So is deciding about heirlooms such as family china or jewelry.”

4. Redirect items. If you come across items you don’t want to keep in the family, selling is an option. But don’t count on receiving a windfall.

“Many of the collectibles gathered over a lifetime may not have much resale value anymore,” says Luis Perez, CEO of Remoov, a San Francisco-based company that helps people declutter. “Baseball cards post-1960s have little to no value at all.”

For belongings you think your children or grandchildren would appreciate, consider giving them as gifts now or marking them to be passed on later. Also, keep in mind that while collections or college textbooks might have personal meaning to you, others might not be interested. “A library card or a playbill from a play you love can mean nothing to your children,” Poznansky says.

If family members aren’t interested, you can try to donate the wares to a secondhand store. Or create a new keepsake, such as a quilt made with T-shirts from places you visited or a collage of old photographs.

5. Set parameters. “If you’re moving to a smaller place, make a comparison to your current situation,” McGregor says. Then, aim to declutter as much as you need to fit the new place, such as 40 % or half of the boxes.

A friend or relative might be able to help you evaluate what to keep and what to pass on. If you’re struggling to downsize, a professional organizer could provide support.

“Some organizers specialize in photo and memorabilia management,” Dooley says. Others focus on the mental health and emotional journey of parting with things and serve as a bit of a life coach.

6. Enjoy the process. “Don’t look at it like decluttering and getting rid of your past, but as a journey through a long life,” Cohen says. Hold your wedding dress in your hands or flip through a photo album and take the time to remember what life was like then.

“Sometimes you just need to remember, to share a story one more time, to be able to part with something,” explains Cohen.

If you’re not ready to get rid of something now, and space isn’t a concern, put it aside for a year. Then revisit the item to see if you’re at a point where you can let it go.

And hold on to special discoveries you come across. “Keep toys you remember your children particularly enjoying — or that you would enjoy playing with with your grandchildren,” Poznansky says.