The Sentimental Organizer’s Guide to Letting Go

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.

10 Thoughtful Questions to Help You Reduce Clutter

Have you started feeling the urge to purge your house this spring? As a professional organizer, I know that decluttering can feel overwhelming. You start with good intentions, but suddenly, you’re surrounded by old clothes, unread books, and sentimental keepsakes, unsure of what to keep and what to let go of. That’s where asking the right questions can make all the difference.

Decluttering isn’t just about getting rid of stuff—it’s about creating a space that supports your life and well-being. These 10 questions are what I use with my clients and they will help you make clear, confident decisions about what stays and what goes, so your home truly reflects what matters most to you.

1. Do I use this regularly?

One of the simplest ways to determine if an item belongs in your home is to ask whether you actually use it. If it’s something you reach for daily, weekly, or even seasonally, it probably has a place in your life. But if you haven’t used it in months (or years), it might be time to reconsider its presence.

2. Would I buy this again today?

Imagine you’re shopping right now—would you purchase this item again at full price? If the answer is no, that’s a strong indication that it’s not essential to your current life. This question helps cut through the emotional attachment and brings focus to the practicality of keeping something.

3. Am I keeping this out of guilt or obligation?

Many of us hold onto gifts we don’t love, heirlooms that don’t fit our style, or items we spent a lot of money on but never use. Guilt and obligation are not good reasons to keep things. Your home should reflect what you love, not what you feel forced to keep. If an item carries more emotional weight than joy, consider letting it go.

4. Does this support the life I want to live?

Every item in your home should contribute to the lifestyle you desire. If you want a calm and clutter-free environment but are drowning in excess possessions, it’s time to align your belongings with your goals. If something doesn’t serve your current or aspirational lifestyle, it’s worth reevaluating.

5. Am I keeping this because I might need it “someday”?

“Someday” is a dangerous word in decluttering. It often leads to a pile of “just in case” items that never get used. Be honest—if you haven’t needed something in a year or more, chances are you won’t. If it’s something easily replaceable or can be borrowed, you probably don’t need to keep it.

6. Does this bring me joy or positive feelings?

Marie Kondo made this question famous for a reason. If an item brings happiness, beauty, or sentimental value, it deserves a place in your home. But if it sparks stress, frustration, or negative emotions, it’s time to part ways. Your surroundings should lift you up, not weigh you down.

7. Is this item taking up space I’d rather use for something else?

Every inch of your home is valuable real estate. Ask yourself if an item is worth the space it occupies. Could you use that shelf for something more meaningful? Could that overstuffed closet be a more functional space if it wasn’t jam-packed? If an item isn’t earning its keep, it might be time to free up that space.

8. Do I have multiples of this item?

It’s easy to accumulate duplicates—kitchen gadgets, black t-shirts, office supplies. If you have more than you realistically use, pick your favorite and donate or discard the extras. Reducing duplicates helps create space and makes it easier to find and appreciate what you have.

9. Could someone else benefit from this more than I do?

If you’re struggling to let go of something, think about who else might need it. That dress you never wear could be perfect for someone who truly needs it. That kitchen appliance collecting dust might bring joy to an avid cook. Donating or gifting items can make letting go easier and more fulfilling.

10. What’s the worst that could happen if I let this go?

Sometimes, we hold onto things out of fear—fear of missing them, fear of needing them, or fear of regretting our decision. But in most cases, if you declutter something and later realize you need it, you can replace it, borrow it, or live without it. More often than not, the freedom of a clutter-free space outweighs the unlikely scenario of regretting a single item.

Final Thoughts

Decluttering isn’t about perfection—it’s about creating a home that works for you. By asking these 10 questions, you’ll gain clarity, confidence, and a greater sense of control over your space. Remember, the goal isn’t just to get rid of things—it’s to make room for what truly matters to you.

Happy decluttering!