How to Declutter Years of Sentimental Objects in Your Home, According Organizing Pros

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When your forever home becomes the backdrop for holidays, birthdays, celebrations, and all the little moments in between, it’s such a special feeling. While each of these occasions brings new memories, they also bring new stuff into your space, not to mention everything you accumulate from daily life. 

Add all of those up over several decades and, without a strict and consistent decluttering policy, it’s easy to find you’ve accumulated closets and drawers full of sentimental items. It may be heartwarming to look back on those on occasion, leafing through old mementos, but what do you do when it’s time to really decide if you need all these things?

Perhaps you’re downsizing from a four-bedroom house into a two-bedroom apartment or packing up your life to move closer to adult children. Maybe you’re staying put but feeling overwhelmed by the amount of stuff in your home, craving simplicity and minimalism as you move into a new chapter. All of a sudden, all of those memories can feel like a burden. How do you know what’s worth keeping and what can be passed along (or thrown out!)? 

To help you make these big, loaded decisions, I talked to several decluttering experts, who shared their tips for downsizing, decluttering, and holding on to your most meaningful memories in the process.

Rather than diving into a closet full of heirlooms and your children’s greatest memories, Meghan Brodie, owner of The House Finch, a professional organizing business in Richmond, Virginia, says to build momentum. 

“We suggest starting in a space with fewer sentimental items, like your kitchen or bathroom,” Brodie explains. “Declutter these rooms first and build your confidence to tackle the more challenging spaces!”

Gretchen Moen, chief clutter cutter at Cut the Clutter RVA in Richmond, Virginia, suggests looking at the places with the lowest emotional attachments, which can also be physically smaller, like a pantry or spice cabinet. This lets you start the process in approachable bite-size chunks. “It doesn’t have to happen all at once. Even 15 focused minutes can make a meaningful dent. Small steps really do add up,” Moen says.

Kristin Gorin, co-owner of Get Organized RVA, warns that sentimental items will spark trips down memory lane and slow you down, so be prepared. “This can bring up a lot of emotion, both positive and negative, and delay progress,” she says. Gorin recommends starting with items that are sentimental but less emotionally charged, like vacation souvenirs rather than your grandmother’s hand-knit blankets. “Save the difficult categories for when you have emotional support with you, such as a loved one or a professional organizer.”

Whether you’re going through your shoe collection or your heirloom silver, know what you need to do — and do it. 

If you’re moving to a new place, your first consideration should be practical. How much space will you have compared to your current home? This will help guide the big items and, eventually, the small ones, too. “Determine the space available in your new living arrangement, and then choose which furniture pieces to take first. From there you can start thinking about smaller items and what you will have room for,” Brodie says. 

As you start going through every item in your home, sort them into categories, like photos, books, and collectibles. “Categories make it easier to see the volume of things, and it’s much easier to make decisions about what to keep and what to purge,” explains Karen Windholz, professional organizer at Sort Toss Repeat in Virginia. 

Then, sort everything into action items: Brodie recommends using colored Post-Its to mark each item for move, sell, donate, or trash. “Quickly go through each category. Don’t overcomplicate it. You will realize that you have been holding on to too much stuff that is actually not even sentimental anymore,” Windholz says.

If you find yourself getting hung up deciding what’s worth keeping and what can go, Gorin suggests “letting the container be the limit.” She picks a container, then holds her clients accountable to only keeping the items that will fit within that container. 

Gorin recommends asking questions to move the process along. “When was the last time I used this? How many do I realistically need? Can someone else benefit from this item because I don’t need this many? Does this item have significant signs of wear?” Your answers can quickly let you know if you really need this item.

Don’t try to do too much at once or you’ll find yourself buried in stuff. Whether you’ve been in your home just a few years or 30 years, the memories packed into the space will feel like a lot, particularly as you try to downsize a significant portion of your belongings. “Decision fatigue is real. When you have a lot of micro decisions, it’s easy to feel overwhelmed,” says Gorin. 

The sentimental side of decluttering is where most people find themselves stuck. Windholz suggests embracing the mindset that you are decluttering to let go of the things that are holding you back. She explains, “Only keep the important things, remember that if everything is important, then nothing really is. Start small and with the least sentimental items. Once you start purging, letting go of stuff will feel better than holding on to it.”

Often, “stuff” comes with loaded memories. A painting may have belonged to a late aunt or perhaps your mother crocheted that small hat for your daughter when she was an infant. “Our sentimental items remind us of loved ones that have passed, different eras in our lives, places we’ve traveled, and our accomplishments,” Gorin says, adding that this is where people can consider the quantity of the items they’re choosing to keep for sentimental purposes. 

“Rather than saving an entire china set that someone has never or rarely used, keep a teacup and saucer that reminds you of that loved one (and use it!) and donate the rest.”

Windholz adds that her role is often to help clients create boundaries around sentimental items. There is only so much space available when downsizing, and this allows you to give more meaning to a smaller subset of items. “Curating a collection of sentimental items is more valuable than having boxes full of old stuff.”

Brodie echoes this sentiment, with a side of it’s just stuff. She says, “If these items are tied to specific people, pick one to two pieces that really give you warm feelings about that person. Just because something belonged to your grandmother doesn’t mean you have to keep it!.”

It’s not unusual for people to get caught up in the feeling that decluttering feels wasteful. All of those items just going in the trash?! It doesn’t have to be that way! 

You can pass these items along, though be careful that you’re not sticking someone else with your trash — and forcing them to do the labor of letting it go. “If you no longer love something or have the space for it, offer it to relatives or friends; ensure they have the space, though, and actually want them,” says Brodie. “The last thing you want to do is create a burden for someone by dumping your unwanted goods in their garage.”

If there’s no one in your friends and family circle who needs your items, yet they still have useful life left, the donate pile is a great way to feel better about letting items go. “If they don’t want an item, don’t be offended, find a local nonprofit to donate to or offer it up on a Buy Nothing Facebook group,” says Brodie.

You can also hold on to your items while giving them a second life with a smaller footprint by digitizing them. Remember, a picture is worth a thousand words. “Scanning photos, letters, or artwork allows you to preserve those memories without needing to store every single piece. And often, you end up enjoying them more when they’re easy to see and share,” explains Moen.

Depending on the size and scope of your decluttering project, or whether you feel too emotionally invested, it’s not a bad idea to consider bringing in a professional or a friend who’s less attached to your situation to get you over the finish line. They can help you put space between yourself and the items, helping you decide what you’re keeping because it is actually meaningful versus out of obligation. 

“We are a neutral party that will not have the same attachment to the items,” says Gorin, who adds that you should be gentle with yourself. “This is hard work. It brings up decades of memories. When done thoughtfully and intentionally, it can bring people into their next era of life by curating their new home and putting in organizational systems that work for their new, current lifestyle.”