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Are you thinking about downsizing, but dreading the sentimental stuff? The kids' artwork. The Christmas ornaments. The wedding dress packed away. You're not alone. For almost everyone, sentimental items are the hardest part of downsizing.

I know, because I've been there. When my husband and I sold our house to live aboard a sailboat, everything we owned had to earn its place. The practical things were easy. The sentimental things took real heart work.

And I'll be honest, I wasn't a natural at this. When we first downsized to a house half the size, I dragged my feet the whole way. I was very attached to my stuff. By the time we sold that house for the sailboat, something had shifted. I kept a handful of real keepsakes and let the rest go with much less grief than I expected. Letting go is a muscle. The first round is the hardest.

Here's what I learned: letting go of sentimental clutter isn't about being ruthless. It's about deciding, on purpose, what you keep, what you pass on, and what you release. You get to make those choices. Nobody gets to make them for you.

If letting go feels heavy, start with permission. My free Reclaiming Slip includes a whole section on letting go, so you can make these decisions with a little more peace. Get your free Reclaiming Slip now.

What we kept (and what we let go)

Before the tips, here's what this looked like for our family. Our rule was simple: keep what's irreplaceable and important to us, on a small scale.

• Photos: We kept them. I scanned our older prints with the Photomyne app (I still have more to scan!), and we made digital photo books we can actually flip through. I have one tub of pictures that still need to be scanned.

• The kids' artwork: Most of it went. I photographed the best pieces and kept a few originals for each child. The ones that made the cut: 3-D paper turtles, the sea creatures with beans and a pop-up book I couldn't part with.

• The kids' mementos: We kept a favorite outfit or two, a few toys and a blanket for each of them, and their baby books.

• Christmas: We kept our homemade stockings and ornaments. We bought each of our kids an ornament every Christmas growing up, so we gave them their collections to start their own trees.

• My wedding dress: I still have it. Maybe I should let this one go but someday it could become a dress for a daughter, or a granddaughter. That's a keep with a purpose (and it doesn't take up much space).

• Furniture and paintings: Sentimental furniture went to family members' homes, and we may take some of it back someday. Paintings by my husband's grandfather went to a family member who treasures them.

• Everything else: Each family member has one keepsake tub. My son has a few more tubs that hold a nativity manger he made and a few classic toys we're saving for his kids someday. My daughter also has some other items stored that don't fit in her apartment. We also kept some camping gear that can be used by the family.

Right now there's a card from my son and daughter on my nightstand. I love seeing their handwriting. I didn't keep every card they ever gave me, and that's exactly why this one gets to be out where I can see it, instead of buried in a box.

All of the items we kept fit in one small storage container on family property. We added venting and racks, and it costs us nothing to store. The kids were young and didn't have homes of their own yet, so giving them a place to keep their things until they settled was part of our plan from the start.

5 gentle tips for letting go of sentimental items

1. Sort your sentimental clutter into three piles

The first step is always the hardest. Once you start, it's rarely as bad as you feared. Sort into three piles:

• Keep: the items you look at and think, "No way. This stays."

• Pass on: items you're ready to give to family or donate, under the right conditions.

• Release: items you can let go of without hesitation. The attachment is gone, and that's okay.

If you're stuck on something, ask: does this hold real meaning for me today, or am I keeping it out of guilt or habit? Answer honestly.

Parting with sentimental items can be difficult. By being selective about the items that you keep, you can make sure that you keep items that truly mean something to you and bring you happiness. Just remember that if you're keeping things to pass down later on, they may not hold the same meaning to someone else.

2. Give your keep pile a second look later

Your feelings about things change over time, and that's allowed. Every few months, revisit your keep pile. Some things will still feel essential. Others will feel lighter to release than they did before.

You also don't have to keep a whole collection to honor it. One special photo can stand in for items you pass on. One favorite piece of jewelry can carry the memory of the rest.

3. Keep the memory, not the object

Photograph sentimental items before you let them go. This is exactly how I handled most of our kids' artwork: I photographed the best pieces and kept only a few originals. Stuff like this likely means more to you than to your kids. For example, my mom gave me some grade school items of mine a while back and they didn't hold any memories for me so I didn't end up keeping them. They held memories for her, not me. She could have easily shared this memory with me through a digital photograph that wasn't taking up space in her closet.

For old printed photos, a scanning app like Photomyne makes quick work of it. Then turn your favorites into a printed photo book. A book showcasing meaningful items is easier to enjoy than boxes in the attic, and you'll never have to dust it.

I photographed the things that were hard to let go of, or that I felt guilty about. Not just artwork: stuffed animals, baby blankets, the outfits I remember them wearing. And when my kids were little, I turned some of their paintings into thank-you cards. The grandparents loved them, and the art got shared instead of stored.

4. Ask your family what they want, and be ready for their answer

What's meaningful to you may not mean the same to someone else. So ask. Invite family over, together or one at a time, to choose anything that's special to them. Our sentimental furniture and my husband's grandfather's paintings all found homes this way.

Be ready if they say no. It can sting, but it's not a rejection of you or your memories. Also, when your kids are young they may not be into family heirlooms or have the space to store them. This might lead to keeping an item for a while longer hoping the answer will change or hoping they'll have space for it some day. If you go this route, be selective about what you keep so you don't use this as an excuse to keep everything.

Remember, someone outside your family may treasure that item and give it new life. There's real joy in seeing that happen too.

5. Give your grown kids their childhood things (or a tub of their own)

Ask your grown kids which childhood things they want. If they want them, set a date and pass them on. We gave each of ours their Christmas ornament collection.

If they're not settled yet, it's okay to hold some things for them, with a limit. Each of our kids has one keepsake tub. When we went through my son's old bedroom things together, much of it didn't hold meaning anymore. What did went into his tub.

And if they don't want something? Don't hold onto it out of guilt. Take a picture, then let it go.

Closing

You don't have to keep everything to keep the memories. Eventually, it feels freeing to know that every nook and cranny isn't full of just stuff. Rather, everything has a meaning, a purpose and a place. It feels lighter to know the important things are kept on purpose.

Choose what matters, find good homes for the rest, and set a limit that protects your space. Letting go gets easier with every decision.

Ready to give yourself permission to let go? The free Reclaiming Slip includes a whole section on letting go. Download it and take the first step toward the lighter life you want. Get your free Reclaiming Slip now.

Frequently asked questions about sentimental items

How do I start decluttering sentimental items when it feels overwhelming?

Don't start with them. Clear the easy things first, like expired, broken and duplicate items, so you build momentum. Then open one box of sentimental things at a time and sort it into keep, pass on and release.

Is it wrong to feel guilty getting rid of gifts or inherited items?

No. Guilt is normal, and it isn't a reason to keep something. Ask whether you're keeping it out of love or obligation. If it's obligation, photograph it, offer it to family, and let it go knowing the memory stays with you.

What should I do with my kids' artwork and school papers?

Keep a few favorites, photograph the rest, and turn the photos into a book. We kept a handful of originals for each child and gave each one keepsake tub.

How do I keep the memory without keeping the object?

Take a photo, write a line about why it mattered, and put the photos in a book you'll actually open. A photo book is easier to enjoy than boxes in the attic.

What if my grown kids don't want their childhood things?

Ask them, then believe their answer. Give them what they want, hold one tub each if they're not settled, and let the rest go without guilt.

Should I keep my wedding dress?

Only if it has a purpose for you. I kept mine because it may become a dress for a daughter or granddaughter someday, and it doesn't take much space. Today, I'd be alright with letting it go. If it's only taking up space you don't have, it can be repurposed, donated or sold.

How long does it take to sort sentimental things?

Longer than the rest of the house, and that's okay. Go at your own pace, and revisit your keep pile every few months. It often feels lighter the second time.

Keep Reading

• Prepare for Living in a Small Space: Declutter Now

• 6 Great Benefits of Downsizing Your Home

• How to Declutter Your Stuff: Start Here Now

• How to Start Living a Simple Life Today