DECLUTTERING SENTIMENTAL ITEMS

(My Secrets & Mistakes!)

My Secrets (and Mistakes) for Decluttering Sentimental Items

Spring is around the corner, and for many of us that means clearing out things that no longer serve us. Recently my husband and I were going through a box of memorabilia from our parents. Both of our parents have passed away, which means we’ve inherited not only their belongings, but also the task of sorting through all of it including old letters, passports, business cards, photos, and decades of paperwork.

Over the years I’ve become fairly skilled at decluttering. I wouldn’t call myself a minimalist, but I do prefer a streamlined life. And I’ve learned that the hardest things to declutter are almost always the sentimental items.

As we sorted through those boxes, I found myself grieving a little. Objects carry memories, and letting go of them can feel like letting go of a piece of the past. Old memories, regrets, or painful moments can get attached to objects. Decluttering can come with a real sense of loss and that’s something people don’t talk about enough.

And when you’re surrounded by those reminders, it can bring you down without you even realizing it.

That’s exactly how I felt that day. Looking through those keepsakes put me in a reflective, slightly sad mood. It reminded me that part of decluttering is learning how to let go—not just of things, but of the emotions tied to them.

Interestingly, my dad was the opposite of sentimental about objects. He was a commercial artist who designed everything from greeting cards to packaging. Yet he would regularly go through his artwork and throw pieces away without hesitation.

At the time, we would protest—“Dad, wait! We might want that!” But looking back, I think he understood something important: not everything needs to be saved forever.

Today there’s actually a term for this mindset and it’s called “Swedish death cleaning.” It’s the idea that as we get older, we intentionally go through our belongings so our loved ones won’t have to deal with mountains of stuff later.

That concept has really stayed with me and I want to share with you some of the tips and techniques i’ve done to reduce clutter.

The biggest mistake people make

One of the biggest mistakes people make when decluttering is starting with the most emotional items.

If you’re new to decluttering, start with the easiest things first:

• the bathroom cabinet

• the linen closet

• kitchen drawers

• old toiletries

• mismatched socks

These things usually don’t carry emotional weight, so they’re easier to let go of. Clearing them out builds momentum and confidence.

Simple tricks that actually help

Over time I’ve found a few strategies that make decluttering easier:

1. Set a timer.
Give yourself just five minutes. Declutter one drawer or one small area.

2. Focus on one space at a time.
Don’t tackle the whole house. Start with a single room, cabinet, or shelf.

3. Donate immediately.
Once the bag is filled, put it in your car so it actually leaves the house.

4. Picture the person who might benefit.
This one helps me a lot. When I imagine someone else truly using and enjoying the item, it becomes easier to let go.

Should You Scan or Photograph Sentimental Items?

One strategy people often recommend is scanning or photographing sentimental items before letting them go. I actually used to suggest this myself when I taught a course called Simplify and Declutter Your Life. The idea was simple: take a picture of something you’re ready to release so you can still hold onto the memory without keeping the physical object.

But over time, my perspective shifted a bit.

There is something about the physical object itself that a photo simply can’t replace. For example, if I hold a letter my dad wrote, it’s not just the words. It’s his handwriting. The envelope he addressed. The stamp he chose. All of those small details create a sense of connection that a digital image doesn’t quite capture.

Digital copies can certainly be helpful as a backup. But I no longer see them as a perfect replacement for meaningful objects.

Technology changes, devices break, and files get lost.

So while scanning can be useful, I’ve become more thoughtful about when it actually makes sense.

I know it can be a challenge to inherit other people’s belongings. I have boxes and boxes of photographs from my mom of people I’ve never even met.

At first I felt guilty getting rid of anything that had belonged to her.

But over time I realized that it’s okay to keep what has meaning for you and let go of what doesn’t.

Keep what brings joy

If you have boxes of letters, photos, concert tickets, or journals that bring you joy, keep them.

I’ve kept many of the letters and cards people have written to me over the years including notes from readers and subscribers. Those mean a lot to me, and I love revisiting them.

Decluttering often happens in cycles. You may look at something today and think, “I’m not ready to let this go.” Six months later, you might feel completely different.

That’s normal.

Sometimes it takes seeing an item several times before you’re ready to part with it.

A Simple Test I Use

One thing I’ve noticed while sorting through sentimental items is my immediate reaction.

When I pick something up, I pay attention to whether it brings a smile to my face or a sense of sorrow.

If something consistently brings joy, I keep it.

If it pulls me back into painful memories or emotions I’d rather not carry anymore, that may be a sign I’m ready to let it go.

At the end of the day, decluttering sentimental items isn’t really about getting rid of things. It’s about deciding what memories you want to carry forward with you.

You don’t have to live with only ten possessions. You also don’t have to keep every single thing that ever crossed your path.

Keep the items that make you smile. Let go of the ones that feel heavy.

If decluttering helps you feel a little lighter and a little more present in your life, then it’s doing exactly what it’s meant to do.

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Peggy Hall
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