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!


Shifting to slow, simple living is a complicated change to make. Sign up for the free 20-part Slow Home BootCamp to kickstart your own Slow Home journey. Find out more and sign up here.

Leave a reply