One of the toughest aspects of sorting through our possessions is deciding which of our most sentimental items to keep. Clothing of a loved one, photographs of a special memory, knick-knacks from a favorite vacation… these items are especially difficult to part with because of the stories that accompany them. Nonetheless, each item we own requires cleaning, storage, maintenance and/or insurance. Therefore, sorting and culling our sentimental belongings is worthy of the emotional roller coaster it entails. Here are a few questions you can ask yourself to help you decide what is worth keeping and what isn’t.
Am I keeping this because I think I should…because I think someone else would be upset if I let it go?
If the primary reason you are keeping an item is guilt, then it is time to let it go. The giver of the item most likely intended it to bring joy, so if it isn’t bringing joy, consider giving it away.
Do I have a place to display and enjoy this?
We collect items because we like them (beautiful dishes, coins, linens, etc.), but then often put them in a box for safekeeping and never look at them. If you have a collection, honor it by finding a way to display it. If you have no place to display or use it, ask yourself if you will in the future. If not, then consider passing it on.
Is this item so out of date that my children or grandchildren won’t want it?
Often we hold onto objects with good intentions of passing them on to the next generation, but end up keeping things that family members don’t want. Storing, moving, and carting objects which won’t be appreciated is a waste of effort, especially since there may be someone else who has great need of the object today.
Is this damaged or in a state of disrepair? Do I have the ability, money, and determination to pursue getting it fixed?
Some belongings are worth keeping, even if they are not in mint condition. In fact, when it comes to antiques, a patina can actually add value. However, most objects lose value and utility as they age. Items that are fragile require extra care and maintenance as well. Keeping an item that can’t be used for its intended purpose is only rarely a good idea. If you don’t want to spend time and effort protecting a delicate piece or getting a broken item fixed, consider letting it go.
Can I capture the memory of this item in an alternate way that better fits my lifestyle?
With high quality photography and scanning widely available, many items may be better preserved through a medium other than a box. Consider photographing the items (e.g. children’s artwork, favorite vintage clothing items, etc.) and making a photo book at a site such as Shutterfly.
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Ultimately, sentimental items are only worth keeping if they regularly and consistently add value to our present lives. Letting go of an item doesn’t mean you no longer love the person it came from or fondly remember the experience that it represents; it simply means that the object’s physical presence is no longer beneficial.
Do you struggle to let go of belongings with sentimental value? What object(s) are you holding onto that you know you should pass along?

This is definitely a hard thing to decide one way or the other, but love your reasoning of adding overall value to our lives and will definitely keep this in mind in the future. Thanks Seana 😉
Janine Huldie recently posted…Surf’s Up This Summer with SurfSweet Gummy Worms’ Sand Pails
Overall value is the rubric for anything we keep, but I know it can be especially hard with items wrapped up in emotion. Still, I see people who have whole rooms full of sentimental items, often interfering with quality of life and usability of the space. All stuff should enhance our lives… if it doesn’t, let it go!
The emotional attachments we can have for our things can prevent us from letting go. Especially when these things are sentimental and remind of us times past or loved ones, letting go can be even more challenging. You’ve shared a wonderful list of questions and possible strategies for handling them. The one about keeping something for the kids or grandkids is an interesting one. I don’t know about you, but I’m seeing that the younger generation of baby boomers’ kids wants less and not more things. The objects we consider treasures, they don’t want. It’s worth having those conversations with your family, which might help with being more realistic about what they value and might want.
Linda Samuels recently posted…Why Do We Hold On to Treasures, Clutter, and Stuff?
I run into this issue with children and grandchildren so often. Items like fine china, which for generations were considered treasure, are just not so popular anymore… especially the floral china. It can be very disappointing to find out that your beloved item isn’t wanted. However, dealing with reality ultimately helps us make smarter decisions than living with false expectations!
Sometimes for me, it’s only about memory keeping. There are things that I would never remember if I didn’t see them, and then when I do, it’s like it opens up a whole world in my brain.
I suppose that’s why I love photography, writing, and even social media. Memory keeping! And without too much clutter!
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Your gift of photography enables you to capture memories in a beautiful and powerful way, Tamara. A coffee table book filled with images of sentimental treasures is something most people would really enjoy. I heard about an organizer with a side business taking special photographs of a beloved family home before a relocation, and either framing the images or making a book… little things like doorknobs or growth charts or special trees in the yard. Such a wonderful way to hold fast to the good memories!
I’ve gone through this process with my kids as they outgrew toys but had a difficult time giving them up. We took photos off the child with the toys and then it was easier for my children to donate toys that were sentimental to them.
Great example of creative problem solving, Susan! Now the kids can look back at these photos over time, and really hold onto the memories of these items they loved:)
I’ll never be able to let go of items our kids created, but — OK, if you push me — George Brett is just a person (even superseded by recent Royals teams) just like Mike Schmidt is a person. Some memories are truly personal (a daughter’s poem to her father) and others are meaningless (the aforementioned sports analogies). Great wisdom here, as usual (!).
It’s all about discerning what brings you the most joy as you look and reflect. We can’t keep it all, so we need to figure out what we most want to surround ourselves with. Fortunately, there are many alternatives for keeping a memory other than holding onto a physical item, such as a video or photo. Thanks for the comment!
I have a few sentimental items that I love because they bring me pleasure to see them. That being said, I do know that it is only me that is attached to the item and the happy feeling they bring me. These items mean nothing to my children because my memories are not theirs. I suppose when I’m gone, they can keep or dispose of them. I have other items however, that were given to me to keep that I really have no attachment to and as I read this, I do question why I keep them stored in a box in my attic that I never use or look at unless I need to move them to get to something else. Time to clean the attic 🙂
The attic tends to be a repository for most of us, doesn’t it? You make an excellent point about items your children will feel no attachment to. I suggest clients give their children permission to let go of these items after they are gone… makes it easier for the children if they don’t feel Mom would be sad if we passed these on.
It can be really difficult to do this. I gave away several things when I moved abroad that I would have definitely kept if I had stayed in the U.S. But overall it has been really nice not to have all the extra stuff!
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Moving does put that little bit of extra pressure on us that sometimes helps us let go. Periodically, there may be a decision we regret, but my experience is that the vast majority of the time, we are glad we let go. There is true weight of carrying items, whether physically moving them from one place to another, or just worrying that I should be doing something more/better with them. Now you have “space” for new experiences!
I would need to pull out my treasure box and see what’s in it to answer that question – and that probably says something right there. At the very least, I should go through and identify why I’ve kept each item and then decide what to do next. I have already purged a number of things that I’d kept since my childhood (and later) for no other reason than that “I’ve always had it” so I am on the right track. 🙂
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You are typically one step ahead, Janet. But you raise a good point. If we don’t even know what we’ve saved, that means we may not be getting much regular pleasure from them. Every decade it is worth revisiting our collection with our current life stage, priorities, and living arrangements in mind!
I usually go through it only when I’m looking for something in particular, or when I want to add to the collection but the tote is too full. 🙂
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It seems like a disconnect that we store precious items and don’t put them in places to enjoy them. My mom had a collection of paperweights. One of the best parts of selling them was to have people own them that appreciated them. I find it best to send these items out into the universe for this reason.
What a interesting collection, Ellen! My Dad collects corkscrews, which he has displayed on his wall. My sister and I often talk about how to honor this collection it the years ahead. Any item deserves attention… which also honors to the collector! The headline to me is, if you don’t wish to display a collection, consider passing it on to someone who will. THIS can be the ultimate way to honor someoene in our life who collected… by sharing what they treasured with others who share the same vision!
Great questions, Seana! I have been working on going through memoriabilia from my parents and grandparents. I don’t have a lot but I want to be able to use these items so I am modifying them to make them work better in our home. I was able to get rid of 50% of my stuff. 🙂
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I love that you mentioned modifying to make them usable. That can be a truly wonderful way to take something with sentimental value and incorporate it into your current life. Old pieces of furniture can often benefit from this approach. 50% is IMPRESSIVE!! Now I imagine you have only those pieces that are most special and the sources of true joy:)
Yes! I condensed everything into one larger bin. I had my husband to the same with his bin but he didn’t get rid of anything. :/ oh well. The kids bin is still untouched by the kids. At least I am showing them they can do this.
Children watch us more than they listen to us, so way to go!
This is where I struggle. When I have things that are sentimental it’s REALLY hard to get rid of them!
Susannah recently posted…Christianity Isn’t Always Sexy
I think everyone struggles more with the things that tug on our heartstrings. Also, decluttering isn’t about getting rid of your favorite, most meaningful possessions. Reminding yourself that you want to make space to enjoy those items that hold the most value can be helpful. It isn’t easy, though… I know!
This is so true for many people and you give great examples on how to deal with it. I like how you mentioned taking pictures of the items. A great way to keep the memory alive.
Kathy recently posted…5 Wild Emotions When Dealing With Clutter
We all offer these tips, just as you gave ideas for dealing with the emotions. In many ways, our posts this week overlap. Emotions are powerfully at play, and we need to find ways to keep moving forward!
This is a very tough aspect of organizing and you’ve done a great job of balancing the necessary with the emotional. I’m not naturally a sentimental person so letting go of sentimental items is keepsakes is not hard for me. My husband and daughter are complete opposites of me, however, and never want to get rid of anything that is highly memorable. But if it’s hidden away in a box or chest, how is that valuing the sentimental item? I think you made a lot of good points and gave your readers a lot to think about. Well done Seana!
Liana George recently posted…Why I’m Removing “Easy” from My Organizing Vocabulary
Thanks, Liana. I definitely agree that some people are more emotionally attached to physical belongings than other. This process can literally be gut wrenching (as opposed to easy!) for so many. But once you start, and establish some criteria, it can get a bit less stressful. Ultimately, I want everyone to enjoy what they decide to keep!
I’m like Liana in that I’m not a sentimental person either and it’s easy for me to let things go; my husband not so much. I’ll never forget watching a show and hearing the expression: They don’t make a hearse with a luggage rack. It really hits home that you can’t take stuff with you, so honor it and use it while you can!
Exactly… if it isn’t making our lives better now, when will it? It is really a mindset about the purpose of possessions in our lives. But helpful to acknowledge that we all come from different places, so each of us needs to find our way to negotiate our feelings and live our best lives:)
I am all about tossing stuff I no longer need…I rather take a pic or make an album of all the pics I saved. I think having the memory is just as important and having the item that will not be used or taken care of as it should.
So smart, Karen. In addition to being more convenient, it is easier to pull out a photo book and enjoy the memories as opposed to having to haul giant boxes down from the attic!
You make some really excellent suggestions here. It’s really important to make sure your possessions don’t become a lump of clutter and that you rid yourself of objects you don’t need, even if they once held some sort of value to you. It’s sometimes hard, but if you ask yourself the questions you have featured above, it becomes a little easier. Nice work. Thanks for sharing!
It can be hard, Morgan. We often equate the object with the memory, even though they are separate things. These items are particularly difficult because they represent the relationships and memory that we treasure most. Nonetheless, keeping an item is not equivalent to treasuring a wonderful person or memory!