Steps to Take When Decluttering Items That Bring Up Emotions

Change and Transition, Grief: Death and Dying - End of Life Planning, Photos and Picture Organizing, Sorting Add comments

Do you find it hard to declutter the past, family items, memorabilia and such? You’re not alone.


Decluttering emotional areas and sentimental items is hard, often very hard. It takes longer and is more emotionally draining than decluttering the bathroom drawers or closets.

When I work with people to declutter the past they will often literally just stop moving and do what I call “trance.” They drift away and can’t pick up any more items. Their minds glaze over and all decision making stops. And, that’s why I’m there. To help them move past the past, one item, box or heap at a time.

Why it’s so hard

You are making a deliberate decisions and sometimes pain-filled choices to let go and start freeing yourself, and your home, from the weight of these things and the past. 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.

Start small

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

Sorting Containers

1. Things to keep (you may need to return to this box again and cull out at least one more time if you’ve kept too much)
2. To give to others (maybe to children, grandchildren, back to where it belongs)
3. Donation
4. Real trash

For each item you pick up, ask yourself these 4 questions: 

1. If my house burned down, would I miss this?

Actually, would I even know I had it? Asking this shocking question several times during any decluttering project really does help get our perspective in balance. We hardly remember that we have 80% of the stuff in our homes, especially from the past. So, if you really wouldn’t miss it or care about it, let it go. Burn Your House Down is also the title of my book and workshop on organizing.

2. Does this item mean something to me?

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, then the decision to remove it from your home should be simple. Decide whether to donate it or throw it away.

If the item has any life left in it, meaning someone else can use it, donate it.
Let the thrift store decide if it can have another go round or is truly trash worthy.
Don’t send stuff to the landfill that doesn’t have to be trash “yet.”

 3. What emotion does this item bring up?

If it does mean something to you, study the connected emotion for a moment.

  • What is it? Why do I feel it?
  • Do I have multiple items that rouse the same emotion? What if I kept one or two that are truly meaningful, instead of blindly keeping everything?
  • Can I take a photo of it and look at the photo from time to time, but let the item go?
  • If the emotion is painful, it’s a good time to release it so that you don’t keep bringing up the pain, grief, loss, regret, anger, etc.

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

4. Would you display the item in your home?

We all keep things that we wouldn’t display in our home. 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 happy with yourself.

  • 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.
  • Bring yourself into the present and the future you really want and desire.

PLAN B: 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. I promise!


If you’re really stuck and can’t seem to move forward on letting sentimental items go, I suggest

1. Help from a Professional Organizer like myself who can care for you in the process of your deciding, and

2. My book Letting Go With All Your Might as it has helped many others with this process. Find out more here (This book is available at most of my live programs too.)

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