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5 Questions to Help You Declutter Sentimental Items - Totally the Mom

5 Questions to Help You Declutter Sentimental Items


Let’s face it. The hardest part of decluttering isn’t the sorting but the emotions we have tied to our stuff. It’s what makes decluttering sentimental items especially challenging.

But there are there are a few questions that you can ask yourself to make the task a bit easier.

Before we dive into those questions, I want to clarify that there is no set amount of sentimental items that you have to strive to declutter. The important part here is to make sure that you are finding the balance that works for you.

If a particular objects causes you to have a negative reaction, if it makes you feel bad about yourself, if it makes you feel sad, if it is a constant reminder of what is no longer in your life, or holds you back from really living in the here and now, then it may be time to reconsider whether or not it is really serves you to keep it.

This isn’t about trying to achieve a certain number of decluttered items. This isn’t about anybody else’s standards. This is about what works best for you, your home and your life.

So, let’s dive in. Here are 5 questions you can ask yourself to help you declutter sentimental items:

Psst…for more decluttering tips,  grab your free decluttering starter guide for busy moms here:

1. What memories am I trying to preserve by holding on to this object, and is the way I  am currently keeping/using the item honoring that memory?

Think about what is actually compelling you to hold on to it. Are you feeling drawn to this object because it reminds you of a person who has passed away or an important event from your past?  Or are you simply holding onto it because it was something that was given to you, or something you’ve always had that you just haven’t considered letting go of?

Evaluate whether this object actually evokes those memories and feelings you’re trying to preserve.

Then consider if the way you’re currently using  (or not using) this object is serving the memory you’re trying to preserve.

This is particularly true if you are keeping something because it is from a loved one who has passed on, or something that is from a different period in our lives (or our children’s lives). We may feel compelled to keep these types of items because we feel like we should. We feel a certain sense of obligation, or we feel guilty when considering letting go of these items even if they really are not serving us in our current life.

Is there a better way that you could utilize this object in order to properly honor those memories?

Is there a way to actually use it, or repurpose it so that it has a function for you? Is there a way to put it on display so that you can look at it and remember the important time in your life that is tied to this physical object?

Remember, as my friend Tara from I Dream of Simple recently shared in her post, 12 key lessons learned from 12 simplicity challenges, simplicity is something that looks different for everyone. Depending on where you are in your own journey,  what you’re comfortable keeping may be much different from someone who is farther along. And that is A-Ok!

2. How often do I ever go through and reflect on these objects and the memories they evoke?

Do you frequently sift through the items and reflect, or do they remain hidden in the corner of a closet or deep in your basement buried in a half-inch of dust?

How often do you  want to be able to go through these items and reflect on the memories that they evoke?

Think about how it would impact your life if these items were lost in a flood or fire.

Before I had gone all in on our own decluttering mission, our basement flooded. And while it was stressful to deal with the aftermath of what was essentially a storage unit in our home, I found that I was actually somewhat relieved to have a reason to get rid of many of the objects I had been keeping down there. Most had little to no effect on our day-to-day lives.

3. How does this item make me feel? What emotions does it evoke?

Dig deep and be very honest with yourself.  It’s very likely that you may have a range of emotions tied to the object, but when you see it, what tends to surface most?

Do you feel sad every time you see it because it reminds you of somebody or some time in your life that you miss very deeply?

If the overwhelming sensation you get from a particular object is the feeling of loss, give yourself permission to let go.

Remember that you are not your stuff and your memories are not the objects in your life. If the things that you choose to surround yourself with do not allow you to find joy, have no purpose or do not serve you in a positive way, then they may no longer have a place in your life. And that is OK.

It is OK to let go. It doesn’t mean you’re trying to forget. It doesn’t mean that part of your life or person is any less important to you. It means you’re choosing to allow yourself to be a more active participant in your present life.

I think this is particularly true when we’re keeping something from a loved one who is no longer with us. We feel obligated to keep the object even though it is a reminder of great loss. And while you don’t want to forget about that person, letting go of that constant reminder of the loss is OK.

If the memory it sparks is more of a reminder of the loss than the person, let it go.  It isn’t serving you.

4. Do you currently have other items that represent the same person or period in your life?

I’ll give you an example. Before I started decluttering, I kept nearly all my kids’ clothes. From baby through toddlerhood, that was such a momentous and meaningful time in my life,  it made me sad to think about getting rid of it. I even tried to justify it by saying that they would serve as hand-me-downs (even though, particularly during the infant years, the sizes never aligned and I found myself reaching for the new stuff more than the old).

But I soon started running out of space to hold the bins, and seeing them didn’t make me feel good. In fact, the overwhelming feeling they evoked was stress, frustration and overwhelm at the idea of storing and sorting through them.

So when I was ready, I finally purged the vast majority of the baby clothes. I allowed myself to keep a few things — primarily the going home from the hospital outfits and a few blankets, but the rest were given away to family and friends, or donated. And it felt so freeing.

Now, I can go into each child’s sentimental bin, look through the items and enjoy the memories from these most special times. I had something the represented some of the most powerful moments of those baby days, I didn’t need to keep multiple things representing that same time in my life.

” If everything is special, nothing is special.”

And by drastically trimming down the number of things I allowed myself to keep, only the most special and meaningful are left.

If I had let myself continue to keep all of it, I would have continued to feel overwhelmed and stressed and not enjoyed the special memories. Because if everything is special, nothing is special. 


5. Does keeping this item from my past allow me to find joy in the present?

Again, do some deep digging and soul searching here.

Are you able to fully embrace the present stage of your life by surrounding yourself with this reminder of your past?

Only you can answer this question for yourself, and there is no right or wrong. But if keeping something from your past is preventing you from fully being able to find joy in your present life (because it evokes negative emotions: reminders of loss, guilt, stress or overwhelm) then give yourself permission to let it go.

Declutter sentimental items in waves

As a final tip, make sure you periodically evaluate your sentimental items. What may have seemed difficult, or even impossible to part with six months or a year ago, might now cause you to wonder why you felt compelled to keep it.

Again, the most important thing to remember when decluttering sentimental items is to find the balance that works best for you. There is no rule that says how many items you’re allowed to keep, nor is there any reason to feel judged for what is special, emotional or difficult for you to part with. Even if it doesn’t serve a purpose for you anymore. Give yourself some grace and permission to revisit a particularly hard choice a few months from now if you need it.

Now I’m curious, do you consider yourself a sentimental person, or are you less prone to have emotional attachments to physical objects? Why or why not?

Ready to start letting more things go? Don’t miss your free decluttering starter guide. Get it here: