The Sentimental Organizer’s Guide to Letting Go
Struggling to declutter sentimental items, family heirlooms or belongings from loved ones? This guide helps you organize with heart, simplify your space and still keep the memories.
How to Declutter When You’re Sentimental
Decluttering is hard enough when it’s just about letting go of things you no longer use or need. But when the items are tied to memories, family history, or loved ones who are no longer with us, the process can feel overwhelming. As a professional organizer—and a sentimental person myself—I understand this deeply. I’m still working through my own parents’ and grandparents’ belongings years after their passing, so I know firsthand how complicated and emotional the journey can be.
The good news is that being sentimental doesn’t mean you can’t declutter. It just means the process might look different for you, and that’s okay. Here are some practical steps (and some compassionate reminders) to help you move forward when you’re decluttering sentimental items.
1. Give Yourself Permission to Take Your Time
There’s no deadline for grieving or for letting go. Sentimental decluttering isn’t something you can—or should—rush. I often remind my clients, and myself, that we don’t have to clear everything in one sitting.
It might help to set gentle parameters, like:
One box at a time.
One hour per weekend.
One category (photos, letters, clothing) per season.
This approach prevents overwhelm and gives your heart space to catch up with what your hands are doing.
2. Start with the Easier Stuff
Not all sentimental items carry the same emotional weight. Some things are infused with deep memories, while others are just “extras” we’ve kept out of habit. Begin with the items that feel less charged.
For example:
Greeting cards with no personal message inside.
Duplicate kitchenware or knickknacks you don’t actually use.
Items you kept just because they belonged to someone else, not because they truly matter to you.
These easier decisions build confidence and momentum so you’re better prepared when you get to the harder pieces.
3. Redefine What It Means to “Keep” a Memory
One of the most freeing mindshifts for sentimental decluttering is realizing the memory isn’t inside the object—it’s inside you. The item is simply a reminder.
If you want to preserve a connection but can’t keep everything, consider alternatives:
Photograph it. A picture of your dad’s worn-out work boots or your grandmother’s favorite teacup still tells the story, without taking up space.
Create a memory box. Choose one small, intentional container for your most meaningful items. Limiting the size forces you to prioritize.
Repurpose. Turn your mom’s old scarves into a quilt or have jewelry resized so you can wear it instead of storing it.
This way, you honor the memory without letting stuff take over your home.
4. Ask: “Does This Represent the Person, or the Clutter?”
When I went through my parents’ belongings, I had to remind myself that not everything they owned represented who they were. A stack of old bills? That wasn’t my dad. A chipped mug from the back of a cupboard? That wasn’t my mom.
Instead, I chose to keep things that truly captured their essence:
My dad’s pocketknife he carried every day.
My mom’s handwritten recipe cards.
Family photos that showed them laughing.
If you keep the items that most reflect the person and let go of the rest, you preserve their story in a way that feels intentional.
5. Share the Love
Sometimes the hardest part is feeling like letting go means losing the connection. But passing items along can be a beautiful way of sharing your loved one’s legacy.
You might:
Offer special pieces to family members or friends who would appreciate them.
Donate useful items to a cause your loved one cared about.
Gift keepsakes to grandchildren, nieces, or nephews so the stories continue in future generations.
Letting something leave your home doesn’t mean it disappears—it just finds a new chapter.
6. Create Rituals of Letting Go
Decluttering sentimental items often stirs up grief. Instead of pushing those feelings away, give them a place. Create a ritual to acknowledge what the item meant before releasing it:
Light a candle and say a few words of gratitude.
Write a short note about the memory the item evokes.
Take one last photo and tuck it into an album.
These small acts can make letting go feel more like an intentional choice and less like a loss.
7. Be Gentle With Yourself
Decluttering sentimental items is not just about organizing—it’s about healing. You may feel sadness, guilt, relief, or even joy, sometimes all at once. That’s normal.
Here’s what I tell my clients (and myself):
You’re not “failing” if you can’t part with something yet.
You’re not obligated to keep everything, even if it was a gift.
You’re allowed to keep items purely because they make you smile.
Progress is progress, no matter how slow.
Final Thoughts
As someone who organizes homes for a living, I can tell you that decluttering sentimental items is one of the hardest tasks my clients face—and one of the hardest I’ve faced myself. The process isn’t just about sorting through things; it’s about navigating memory, identity, and love.
If you’re sentimental, you don’t have to change who you are in order to declutter. Instead, honor your emotions while creating space for the life you’re living now. Keep the treasures, release the rest, and remember: the love and the memories aren’t in the boxes in your attic—they’re in your heart.