
Are you ready to shed some belongings, but are hitting a roadblock with the sentimental ones? Recently I had the opportunity to speak to a group of seniors on this topic. I began by reviewing the various kinds of items that tend to carry emotional significance, grouping them into four major categories:

These types of possessions tug at our heartstrings, making it hard to decide how to proceed. Often, we end up stashing them away in remote storage locations, such as attics, basements, garages and storage units. While this alleviates our short-term desire to purge our living space, it often backfires in the long run for a couple of reasons:
- Items we can’t easily access are rarely seen or enjoyed
- Offsite storage is expensive
- Important memories may be lost or damaged
- We risk creating a burden for family members after we are gone
Another common solution is to pass emotionally-laden pieces down to family members. While this may make us feel better, such an approach is also not ideal because:
- We risk making others feel guilty about letting go of items that were special to us
- We often crowd their space
- We put the burden of decision making on someone else
The better course of action is to intentionally curate our collection of sentimental possessions, aiming to keep those pieces that have the most meaning, instead of keeping everything that might have some meaning. Furthermore, it is helpful to be aware that not everything that has value to us will have equal significance to our family members. For instance, one attendee shared that she has a folder of letters she received from colleagues when she retired a few years back. She enjoys periodically reading them, but the rest of her family probably would not as they don’t know the people or situations that they reference.

Legacy items – those we seek to pass down – should be ones with which family members can connect. In contrast, memorabilia we are keeping primarily for own benefit can be simply labeled, “Feel free to discard,” a kind and helpful instruction to those who will be managing our estate.
The question remains, how do we decide what to keep? Here are a few questions to ask:
What does this item mean to me?
Simply being part of our past is not a good enough reason to keep something. Focus on those that spark the best memories.
Is there a story associated with this piece?
The best memorabilia have great stories attached, much the way a piece of art is more valuable when we know its provenance.
Is there anyone in the family who wants this?
We should never assume that “someone will want this.” Today’s young people often live in tight spaces or have differing tastes.
Is the item in good condition?
If not, we should consider whether it can (or should) be restored, and if we want to invest the time, money and energy to do so.
What is the best way to preserve the memory or the story?
Sometimes the best way to preserve a memory is not by simply keeping a possession. For example, a photograph of grandpa in his favorite recliner is more practical than holding onto the fraying, sagging recliner itself.
As you might expect, there are no “right” and “wrong” answers to these questions. Rather, the goal is to thoughtfully prioritize.

Lastly, the practical issue emerges of how to shed those items that are sentimental. It can be difficult to throw away or donate something we feel emotionally tied to. Our group brainstormed a couple of suggestions:
=> If it is something with practical value, use it.
One woman shared that she has three sets of china in her home: her own, her mother’s and her grandmother’s. These take up a lot of space in her home, and her daughter has already told that she doesn’t want any of it. One idea was simply to start using it, and even though it may have a gold trim, to go ahead and put it in the dishwasher. A set of china that is chipped or missing pieces is easier to let go down the road.
=> Find an appreciative donation recipient.
Multiple people have furniture that is not “au courant,” but is still in good shape. Organizations such as Habitat for Humanity Restore can often use pieces like these to furnish homes for people who are in need. It is easier to let go when we know our pieces will go to good use.
=> Utilize technology to capture the memory.
One woman shared a grass skirt, flower ley and ballet slippers that her granddaughter wore in a performance when she was little. The woman is holding onto it for now because she loves looking at it, but she knows that someday she will let it go. We suggested taking a photo of her and her granddaughter holding the outfit, and then writing a few lines about her memories of that event.
=> Recycle.
It may come as a surprise to know that most reputable junk haulers today will donate or recycle as much as possible of what they collect before heading to the refuse center. This process not only saves them money on dumping fees, but it is good for the environment. Fabrics can be taken to textile recyclers, auto parts can be dissembled and used, glass and metals can be recycled, paint can be treated and reused, and even some plastics can be used to create products like flooring, furniture and more. If our sentimental pieces are no longer usable, this can be a good option.
=> Digitize them.
While old papers often have significance, they are subject to deterioration and decay. We are fortunate to have the option today of digitizing old photos, documents, movies, slides and cassettes. Companies such as EverPresent and LegacyBox will take boxes of memories and return them to you on disks, thumb drives or other digital media.
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Simply talking with others about our memories can also be a healthy way to prepare to shed items. Knowing we’ve had “one last chance” to reflect and enjoy them can sometimes be enough to open the door to letting go.
Do you have a tough time letting go of sentimental possessions?

I really hate clutter and constantly going around my home purging the items that my husband and/or kids seem to want to hold onto. But I do get the sentimental value of certain things and for those, I am equally at fault I suppose. But I do love your suggestions here and may consider having some put into digital media as suggested if possible. So, thanks for sharing about these companies that do just that!
You are so right that it is a “constant going around the house and purging!” The digital storage is a great option, especially for items that are beginning to decay.
Sentimental or emotional belongings are the hardest to declutter. I love your suggestions! My favorite is attaching a note to memorabilia that means something to the owner but will mean nothing to anyone else giving them permission to discard. Thank you for these great tips, Seana!
Diane N. Quintana recently posted…How to Help a Friend De-Clutter
Permission to discard is a beautiful thing! We sometimes offer that voice with clients, right Diane? Why make it harder for loved ones to let go of stuff that we would have been happy to have them shed?
Love these suggestions! This is a topic that has been on my mind a great deal. Thanks for your thoughtful approach.
Are you in the middle of decluttering some sentimental items? This can be our own belongings, or those owned by a parent. It is always one of the toughest categories to manage, so having some perspective before we begin can be very helpful!
This is the toughest one for me. I feel like all of my grandparents were packrats and it was tough for my parents to sift through. Now my kids have six grandparents and my parents have so much stuff. Cassidy’s day is in the process of moving so is getting rid of a lot and Cassidy struggles with it because we don’t have use for much. The sentimentality is probably the toughest part for me.
It is hard, Tamara. We are lucky if we have loved ones who meant so much that we struggle to let go of things that remind us of them. Fortunately, you have amazing photography skills and I imagine you can put together some pretty impressive digital/photo treasures that will hold the memories while freeing you of some of the stuff!
I was talking to someone about this topic over the weekend. The legacy items are so important to determine in an older person’s home. They were so frustrated because they couldn’t find the words to explain that they didn’t want to deal with their stuff when they passed. I suggested approaching the loved one and to express the feeling of overwhelm they are dealing with just looking at these items. Then, after they respond, ask them, “what are your favorite items that you want to pass on to your grandchildren/children?” Writing down these items in a document attached to their Will works nicely. My mother did this with a silk rug and her jewelry because these were the items she wanted to go to us. But, when it came down to it, my brother didn’t have the room for the rug so he gave it to me. We had it for many years until it was ripping. He ended up picking out other things that he needed in his place.
Sabrina Quairoli recently posted…4 Areas of an Organized Closet Made Simple
That is such an interesting story, Sabrina! This issue of passing items down can become fairly complicated. We want to honor the giver’s intentions, while also staying true to our own priorities and needs. It sounds like your family worked out a solution that really “worked” for everyone. Thanks for sharing:)
The sentimental stuff is the hardest. You gave some great guidelines to help with the decision making process. We are seeing a lot of people lately who are struggling with this issue. It so hard. Thanks.
Yes, I have also been working with this quite a bit. Many people face it when they are trying to downsize, and the reality that perhaps your family members do not want your precious items can be painful. The more we talk and think, the better decisions we will make.
I love how you’ve categorized the types of sentimental possessions that are challenging to let go. The questions for evaluating each group are also helpful. But in particular, the ideas for how to let things go by giving them “safe passage” is another essential that you brought up. When it comes to those items we are emotionally attached to, letting go goes more smoothly when we can find a source that will take them and appreciate them as much as we did. While the process can still be difficult, it is a process. I have found that once clients get into the organizing, editing, and decision-making mode, they eventually become ready for letting go of the harder stuff.
I have found the same thing, Linda. It is usually difficult to even think about letting go of these items when we begin, but it gets easier over time. Today I worked with a client who had linens that she didn’t need. When we began, she felt an emotional attachment to all of them (baby sheets, little boys sheets, etc.). She didn’t want to shed any of them. By the end of our session, she had decided to donate many of them. It was a process, but we moved at her pace, and she felt great with the result.
I realized last summer how much of my furniture and other household items have history, whether they came from my parents, grandparents, or in-laws. They are all special to me for that reason, but I don’t imagine they’ll be much interest to anyone when I downsize or pass away. In a way, that makes me sad, but it really is just “stuff” isn’t it?
The emotional value of our stuff comes from us. If the items pass on to someone else who doesn’t have that same connection, that particularly significance will no longer be relevant. I agree that at some level that can make us sad, but on another level, it is freeing. We can enjoy our belongings while they have value, and then release them without guilt.
My aunt made a lovely shadow box with sentimental items that honored the memory of her husband. She displays it where she can see it every day. She also donated musical items to a local junior high school. The music teacher appreciated them so much that he even posted a plaque in honor of this donation in their music room. She kept and shared!
What a wonderful story… the school gets the instruments and the inspiration for the gift is honored. I just love this story Olive!