Facing Sentimental Items While Trying to Get Organized

Sentimental keepsakes, mementos, and memorabilia. It’s one of the toughest categories that I go through with clients, and I talk quite a bit about this in my book, Clever Girl’s Guide to Living with Less. I bet it’s a tough one for you, too.  

sentimental items


So, what do keepsakes look like to the untrained eye?

Ticket stubs, stuffed animals, a baby’s outfits, graduation tassels,
programs, buttons, figurines, t-shirts, jewelry, hats, bronzed shoes,
trophies, pressed flowers, greeting cards, toys, newspaper clippings,
love letters, mixtapes, travel souvenirs, report cards, blankets,
handmade cards, kids artwork, matchbooks, foreign currency,
journals, books, baseballs, china, yearbooks, old IDs, 
day planner/calendars, photos, postcards,
and so on, and so on. 

They’re from our youth, our past (and current) loves, our friends, our careers, our travels, or handed down from our family members to treasure. They’re from great moments, or sad moments, or even from a moment that in of itself wasn’t very special, but the way we remember it is. 

And, they kind of cripple us when we think about letting them go, don’t they? We fear the thought of parting with those items…  as if somehow, we’re either betraying our past self, or someone else or feeling like we’ll lose part of ourselves if we part with an item. (Even though we know that it’s an irrational fear it still lingers). We are afraid we’ll lose the memory itself, and our ability to share our story, without it. 

We love the emotions we feel when we touch and revisit them. Our hearts warm and we sigh for the past. But not always, though, right? Sometimes, they elicit negative feelings: guilt, sadness, regret, heartbreak. Why would we keep things that make us feel bad? Why do we do that to ourselves exactly?

We can all use a little help in getting us through the process of looking at our treasures and deciding we can let go of some of them. I’m not saying to toss it all!  I think we all love our collections and our walks down memory lane and should have some props for our ability to do that. What I want you to do to do is think about your goals for your home and for your life, and whether or not holding on to too many items that have little (no?) other value besides “triggers old memory” take up more your home and real estate than you feel they should, given your goals for how you want to live in the space. 

I want to walk you through a few steps to the process of reviewing and editing down your collection of keepsakes and memorabilia, and I want to help you by giving you some questions you can ask yourself as you go through the process. 

First, since we’re talking about the sentimental, and not the practical, we need some “big picture” philosophical questions to help guide through it. As you think critically about items, ask yourself:

  • What do I gain from keeping this? What do I lose from keeping it?
  • What do I lose from letting it go? What do I gain from letting it go?
  • What would my past-self say if it knew I still had this, and what would my future-self say if it knew I let go of it? (I *love* this one!)
  • Am I keeping it primarily because I want someone else (child, grandchild, etc.) to find it as emotionally valuable as I do after I’m gone? (kids artwork and old report cards, anyone?) And, do I know for sure they will value it as I hope they will?
  • The “5 Why Analysis” is a great exercise to help determine the root cause of why you’re keeping something.  The exercise helps to force a bit more honesty than you might feel on the surface. 

Okay, they don’t ALL have to be big and heavy questions. There are some practical questions we can ask, too:

  • How much space of my very valuable real estate and storage space am I willing to allocate to “items that don’t have a function, but only serve to generate memories when I revisit them”? Can I set a limit to the space it takes, and then prioritize what goes into that space?  
  • Do I have more than one item that reminds me of that particular person/place/moment Would I be okay if I kept only one of those items? Gosh, this comes up so often when going through things like your children’s old clothing or artwork. I know how tough this one is… be critical of yourself with this one! Do you need 10 outfits from when your child was growing up, to help you remember they were that age once? Do you need every rainbow picture that was fingerpainted?
  • Can I rank importance among them? Set up 3 piles, and rank what goes in each:
    • “I could never ever ever let go of this item, and if the house caught fire, I’d rescue it.”
    • “I am glad I’ve kept this. I enjoy revisiting it occasionally if I stumble upon it. If it were gone forever, I’d miss it, but it wouldn’t really impact my life.”
    • “meh, I kept it at the time, but I don’t need it anymore. Sure, I remember a moment when I look at it, but it’s not a critical part of how my life has turned out.”
  • Do I need to keep the item as it is, or could I take a photo of it?  Scan copies of cards or letters? Create a digital scrapbook? Capture it all in a cloud-based collection of images that I can keep for myself or share with others, like Artkive? Or turn into a shadow box?  Or a keepsake quilt? 
  • Is there someone else who’d love to have the keepsake for their own memories? This is a good way to think about family heirlooms… you may have other family members that would love them, too.
  • If someone I care about accidentally came across this item, would it be awkward or upsetting to them

  • Does the item bring me sadness or make me feel bad about myself or someone else?

  • Am I keeping it because someone else expects me to, but it doesn’t mean anything (or that much) to me, personally? i.e., is the primary emotion you attach to it obligation or guilt


So, how do you get started?

1) Start small.  It’s not about tackling everything. It’s about addressing some items and making some tough decisions. One box. One drawer. One bulletin board.  Wherever you keep the stuff that you know I’m talking about. Don’t let yourself get overwhelmed.  Start with one group, finish it, then move to the next.

2) Set the space limits. If you’ve decided that you’re editing down your collection because the value of your storage and your real estate is more important, know what that boundary is that you’re setting for yourself. One large bin in the basement? One drawer in your nightstand? One under-the-bed box? Whatever it is, have a good sense of the capacity as you start, so that you can help meet your own vision. 

3) Give yourself time, but not TOO much time. The goal is to edit down what you have. You’ll relive some moments while you go, but stay on task, and keep working through the collection. 

4) Clean items you plan to keep. Sometimes, these can be a bit dusty. If they’re important to you, take care of them so that you can preserve them well and longer. 

5) Honor what you’re keeping. Finding things that mean a ton to you, bring you joy, make you smile when you see them?  What about displaying them, so that you can capture that feeling more regularly? 

6) Really want to keep it, because you want someone else to inherit it? Take some time to write down the stories of why the items are important. A trinket someone else inherits without context can easily be seen as expendable. Help your legacy value what you hold dear.

7) Not quite ready to let go just yet? Create a time capsule. Put aside a collection in a bin or a box, and vow to give it real thought about letting go. If you haven’t had a reason to think about the items or go looking for them for 6 months, you can feel more comfortable letting go at that time.  

Here’s a Clever Girl tip:  Sometimes, when I work with a client, I go through items and place them on display for them to select what to keep and what to part with, in a way where they can’t touch them. Why? Because touching an item reinforces an emotional connection to it.    

Do you have a buddy you can trust for this exercise?  Someone who would be willing to go through the items physically (and not judge you for your decisions)? Maybe that’s just the help you need. Maybe you can help keep each other focused as you go through this challenge.  






  1. Autumn Leopold

    What a great post Kathy and so many good ideas in here! I love the idea of taking pictures of the mementos and then letting them go. Then I can make a photo book of them. So whenever I feel nostalgic I can look at the photo book. I have a few areas of things I kept in my life that I really need to do this for. Thanks for the inspiration!

    • clevergirlorg

      So glad you liked this one! I feel like this is such a tough one for women and men, young and old alike!

  2. Janet Barclay

    This is definitely one of the hardest categories to organize. That’s one reason I decided to focus on business organizing rather than residential (before I evolved to what I’m doing now). These are great guidelines!

    • clevergirlorg

      Thanks so much, Janet!

  3. Bev Moranetz

    This is the thing my clients struggle with the most. I do mostly office organizing but we run across sentimental papers every time. I encourage my clients to get a pretty “keepsake” box for their important papers to store in their closet or office. I have one and if I’m having a rotten day, it holds things that will remind why I’m so lucky!

    • clevergirlorg

      Thanks, Bev! You’re absolutely right… Sentimental items can pop up in any room of the home, even in the paperwork! I love your idea of everyone getting a pretty box for those… they don’t need to be in your main filing system, but you want to access them when you need to tap into the memories the most. Thanks for sharing!

  4. Deborah

    Kathy, what a well thought out and helpful post! You deal with the many different emotions our clients deal with (and shhh…me as well!) as well as practical suggestions. This is the first time I have seen this topic dealt with so well and thoroughly. Thanks for sharing!

    • clevergirlorg

      Thank you so much, Deborah! What lovely feedback! So glad it spoke to you… and hopefully, your clients!

  5. Pam Faulkner, Faulkner House Interior Redesign, LLC


    What a wonderful post. I love this because I’ll bet all of us have said nearly all of these things to different clients at one time or another depending on the situation.

    Making a memory box of potentially collectible items like long ago tickets, programs and an autographed album cover from The Beatles is one thing. Making one for every dance, or event is another. Curating is what we can do for our clients and help guide them through the process. It can be traumatic and we can make it less so.

    • clevergirlorg

      Thank you so much, Pam! So glad you found your way to my post and blog… I appreciate your kind words!

  6. Kim

    This is a great post!! Sentimental and emotional attachments are really challenging for people. I love the questions to ask yourself and may use them in the group I facilitate. I think they would really help people to move forward. Thank you

    • clevergirlorg

      Thank you, Kim! Hope it helps you move your group forward!

  7. Regina Sanchez

    This is a great post Kathy and such an important topic that we as organizers have to deal with. Love the questions you pose. They will certainly help clients make a decision to the significance of the treasure they can’t let go of. Thanks for sharing this.

    • clevergirlorg

      Thanks, Regina! So glad you enjoyed this one!

  8. Jocelyn Kenner

    Kathy, brava on a honest and inspiring post. I will be sharing your methodology with several clients and I think you handled a tough subject with wisdom, practicality, and kindness.

  9. Ruth Honeycutt

    This is one of the best posts I have read so far. If it is okay with you I would like to copy and print for future clients dealing with this particular issue. I even plan to use your ideas for myself. Thank you for your insight and wisdom.

    • clevergirlorg

      Hi, Ruth! I’m so glad this one spoke to you! I’ll follow up directly about your copy and print request. Thanks!

  10. Mary Sander

    Kathy, Catching up on past LinkedIn posts.
    Very helpful article, I always think of “clutter busting” as peeling an onion, one layer at a time. With your clear questions an steps the process can be much easier. Thank you for your excellent sharing.
    I will be using these steps soon with my young adult daughters and the items they have left for me to save for them..


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