3 Questions for Decluttering Sentimental Items

william morris - useful or beautiful
{via Pinterest via E17 Art House}

Please know: decluttering emotional areas and sentimental items is hard. Often really hard.

It takes longer and is more emotionally draining than decluttering the kitchen drawers or wardrobes. You are making a deliberate and awesome choice to start freeing yourself and your home from the weight of these things, but be patient with yourself. Take time. Don’t let go of certain things if you are really having trouble with it.

You know the best answers for your own life. Sometimes you have to go with your gut. Sometimes you have to be brave.


Today, choose a small area to start. Perhaps:

  • one storage box of keepsakes
  • a shelf of knick-knacks
  • a cupboard of old toys or clothes from your grown-up children

Somewhere that tugs at the heart strings when you think of it.

Then, grab a garbage bag and a donate box. And simply start.


For each item you pick up, ask yourself these three questions:

1. Does This Item Mean Something to You?

Often we keep things because we think we “should”. Or because it is representative of good times, fun holidays, our now-grown children, or people we love. But does the actual item, the thing you’re holding in your hand mean something to you?

If not (and you may be surprised by how many of these things do not mean anything on close inspection) then the decision to remove it from your home should be simple. Decide whether to donate it or throw it away.


2. What Emotion Does This Item Bring Out?

If it does mean something to you, then ask yourself the above question.

Study that emotion for a moment.

What is it? Why do you feel it?

Would you still feel that emotion without the physical item? (If yes, then your decision has again been made. Decide to donate or throw away.)

Do you have multiple items that rouse the same emotion? What if you kept one or two that are truly meaningful, instead of blindly keeping everything?

If there is no strong emotional attachment, then again, you can more easily decide to remove it from your home.


3. Would you Display the Item in Your Home?

We all keep things that we wouldn’t display in our home. And it’s not my intention to have you remove everything that you wouldn’t hang on the wall. But asking yourself this question forces you again to really examine why you’re holding on to the item and what the item itself means to you.

If you wouldn’t display it, then really examine your reasons for keeping it. (Remember, there is no right or wrong here. But the intention is to pare down and simplify these sentimental things.)


Once you’ve asked yourself these questions and decided whether to keep the item, donate it or throw it away – you can let go and be proud.

Let go of the guilt of removing it from your home.
Let go of the weight of the thing you are keeping.
Be proud that you are surrounding yourself and your loved ones with things that are truly meaningful


If You’re Really Struggling…

If you’re really having difficulties letting go, you can box up the firm maybes, write the date on the box and 6 months later, if you haven’t missed or needed anything in the box, donate it, unopened.

(Avoid this if possible though – you are more likely to hold on to things unnecessarily if you know there is a second-chance rule.)


There is no easy way to declutter and simplify sentimental items, but these questions should help as you move through your storage. Also know that it does get easier. As you begin to feel lighter and happier in your newly simplified home, it will not be so difficult to let go of things. Promise!

And if you’re struggling, please let me know in the comments or via email. It’s hard, and I’ve been there!

20 Responses to 3 Questions for Decluttering Sentimental Items

  1. As a teen I collected unicorns, and loved Cinderella. We were poor, but my mother still bought me many expensive porcelain unicorns, which she paid for in installments. She also purchased many beautiful Cinderella collector plates for me, paying the same way.

    Anyway, many of them ended up getting broken while packed in a box after I moved out. That was years ago, I am in my 30’s now.

    So, what would you do with these items? I don’t really want to display broken items, plus I grew out of unicorns, but the items represent something to me, that my mother cared enough to get these things for me despite the fact that we didn’t have a lot of money. I didn’t even ask her for them.

    So it’s hard to just toss it but I am seriously trying to declutter and only want items we need or are beautiful to be in my house…

    Really torn here. Love your blog and love that I discovered it via Joshua Becker’s site! Thanks!

    • Colleen, I think that the most important fact here, is that your Mother CARED enough to buy you things that she thought would make you happy. I think that the memory of the gesture, can hold you up.The thing itself, is just a thing. It is not the love, or the sacrifice, that your Mother made to get it for you.If you appreciate the sentiment behind the knick-knacks, then you can rid yourself of the clutter. without ridding yourself of the memories.

      • Also, some people choose to keep fond memories like that as stored (usually digital) pictures. It can serve the same function, in a sense, as a journal. I like to keep a picture journal, myself.

        But in the end, it’s obviously up to you, Colleen. Maybe you take pictures and get rid of them all. Maybe you get rid of all but the one that is most whole/least broken, perhaps as something you might be able to give as a present to one of your children on some occasion.

        Or perhaps you follow Carolyn’s advice to the letter, and realize that this is such a big memory that you’re not going to forget it, even if you just get rid of all of them.

        So review your options, and take some time to think. Just try to think calmly. :)

  2. My dad used to build things with wood — shelves, cradles, wall hangings, cedar chests for my girls’ graduations, etc. He has been gone 16 years. Like my mom says, “We can’t keep every single thing Dad touched.” I have been taking pictures of things Dad made, and keeping them in a photo album. I write approximately when he made it, for whom, what the reason was, etc.

    • what a great poem! I love it. it raises an interesting question to me, how can we ever NOT feel connected to God? It is our natural state and then, not only do we sometimes feel not connected to the infinite, but we convince ourselves that we need to spend our lives in search of this connection, we need to spend our lives grasping for it. Why do you think this is the case?  |  

  3. Great questions! I have struggled with simplifying sentimental things over many years and these are the kinds of things I ask myself now.
    A further point regarding #2 – sometimes the emotion is not positive. Sometimes we keep things that make us feel guilty, or in some other way horrible, and yet we feel like it would be even worse to get rid of the thing. I had something that my Poppa made for my Mum, she had given it to me as a child, and I had pretty much ruined it. I didn’t know it was precious/sentimental to her until much later. Up until a few years ago I still had that ruined object, missing the piece that would make it repairable. Why did I keep it? To hide my guilt about ruining it? To beat myself up? Or just because I didn’t know what to do with it since it was broken and it felt wrong to put it in the trash? (like Colleen’s unicorns). In the end I sat for a long time and thought about the item and then forgave my younger self for being a kid, acknowledged that I couldn’t change the situation, and tossed it into the trash. I feel better for doing that. Not that I’ve forgotten about it, but I don’t have a useless lump of wood tormenting me all the time!

  4. Good reads. I have a cow collection and I bought them cause I liked them. I still like them, but they hold no sentimental value, just cause I like them. I use them to decorate for the various seasons. I’m sure I could use natural objects to decorate and get rid of the cows. Maybe keep one or two cows and sell the rest. Taking pictures is certainly a good idea. Thanks for all the tips!

  5. Thank you for the tips! I am in desperate need of decluttering. I have a box of things I’ve kept from my boyfriend over our years of dating like hand written letters, cards, ticket stubs, etc. I think I will scan them and turn it into a photobook or something. I also have held on to the Playbills of every musical I have ever seen, but I guess I can hold on to the memory of having seen it and get rid of those too.

    • I met a woman who was buying porcelain odds and ends (which I was selling because I’m a hoarder and my husband is a minimalist) who told me that she. Buys porcelain plates, ornaments, bowls, anything really, and then breaks them in order to make mosaic pieces from them. Seems like a goodwayofusinf some shards of sentimental pieces in one large piece? Just a thought…..

  6. I’ve been looking for information about getting rid of sentimental items but I haven’t found anything that gets close to addressing my problem. My mum died 2 years ago and we didn’t have a close relationship – however, as I have discovered when a parent dies it presents new levels of awareness of the quality of your relationship with them. My mum gave me away when I was eight as she couldn’t cope with looking after me. Until I was eight she regularly beat me up and was not the most
    nurturing parent in the world (!). She was an artist (not famous) and as I’m the only child I had to clear out her stuff, which included numerous paintings and drawings she did.

    I have been struggling to decide whether to get rid of them or not. I don’t want to put them up in my house as my memories and association of them remind me of my mum and the fear and terror I felt. But I am worried that if I sell / donate them, I may regret it a few years down the line.

    I know I could put them in a ‘maybe’ box but they’ve already been hanging around in my spare room for two years!

    Any advice or comments from those of you with a similar experience would be gratefully received!

    • Hi Kate,

      I am very sorry that your mother wasn’t kind to you. Your decluttering predicament is tough because not only is your mother deceased, but she was also very abusive to you.

      Here are my thoughts: Art is a very personal as it is creative self-reflection. That being said, I think you need to let go of some of that artwork. If you are scared that you may regret selling/donating her artwork, I suggest that you go through each work of art that you have from her and select no more than three pieces to keep. If you wish, take photographs of the pieces of art before you rid them from your home.
      Try to select ones that you either really like or select pieces that don’t evoke such a feeling of terror. Keep those 3 pieces of art you decide to keep out of sight. Come back to them in a few years and decide again if you want to continue to hold onto them or not. If after a few years the 3 pieces that you’ve kept still evoke strong feelings of terror, then I would suggest departing with those last remaining pieces too once and for all.

      Not to get too personal, but have you ever sought out any kind of help for the abuse that you’ve suffered? I know that sometimes we hold onto stuff that isn’t healthy of any number of psychological reasons. I had a bad period in my life in 5th and 6th grade, and I’ve noticed that there are certain items I have that I am strangely drawn to, so items that bring back my “bad” memories I am finally choosing to depart with. Best of luck to you.

  7. You really make it seem so easy with your presentation but I find this topic
    to be really something which I think I would never
    understand. It seems too complicated and extremely broad for me.
    I’m looking forward for your next post, I will try to
    get the hang of it!

  8. This is good advise. Going to attempt to try this. My mom will be gone three years soon and I not only have my stuff, but family heirlooms as well that he had. I am having difficulty deciding about some of these things. I have some collections too. It’s true, how many varies does one need on a shelf? I’m 60 and know eventually, if not already it’s too much. I guess for me perhaps I have this stuff because stuff I still have and loved ones; Dad, Mom and my husband have passed. Just a brother and a few cousins left. No children. Enjoyed your article. Also we have a good Australian friend in Australia. Was in Sydney in 1971 for a short good time.