I Hate Me, But I Love You - Our Guide to Decluttering Objects Tied to Guilt

Decluttering is challenging enough, but when it comes to items with sentimental value, gifts, or big-ticket purchases, sometimes it’s even harder to let go without feeling a twinge–or wave–of guilt. The theme of keeping things out of guilt comes up again and again whether organizing with our clients or organizing our own homes. It can feel difficult to impossible to get rid of things that we inherited from a loved one, something we spent a lot of money on, and/or received as a gift from someone we care about. 

As our title suggests, keeping certain belongings can feel like hating ourselves in order to prove that we love others. 

However, learning to release things that no longer serve you can bring a huge sense of relief, opening up space in your home—and your mind. Here’s our compassionate, guilt-free guide to help you thoughtfully let go of these tricky items.

Quick disclaimer: we are talking solely about items tied to guilty feelings here, so stay tuned for a future blog about decluttering items that have sentimental value. We do recognize that some items are tied to both sentimentality AND guilt, however, those items would still be characterized as more sentimental.

First, we must understand why we feel guilt around certain objects–let’s consult with our favorite researcher on guilt, shame, vulnerability, and courage: Brené Brown.

Brené Brown defines guilt as “[holding] something we’ve done or failed to do against the kind of person we want to be.” (Brown) In other words, guilt is often about feeling that our actions and behaviors don’t reflect who we want ourselves to be. When it comes to our belongings, guilt could emerge in several ways:

1. An object could represent a person or ancestral idea we care about, however the object may not fit our personal tastes.

2. An object could be tied to someone or something we love, but the object is not useful for our current lifestyle.

3. An object could represent a large investment that we regret making.

4. An object could be important to our family, and we ended up with it, but it doesn’t fit because it simply isn’t important to us.

5. An object could represent an aspect of life that we think we should have, but it actually doesn’t represent our values.

6. An object could represent a life we strive towards, but never achieve.

All these objects have something in common: they either reflect someone we wish we were, or they reflect something that we know we aren’t. Perhaps they represent a version of ourselves that someone we love made-up. We may feel obligated to hold on to these objects for what they represent to others or what the object used to represent to past versions of ourselves.

Feeling guilty while decluttering is completely normal. 

We often attach emotions to our belongings, especially when they’re tied to memories, relationships, or financial investments. Gifts make us feel obligated to the giver, heirlooms connect us to family, and expensive items remind us of money spent. Realizing this can help you approach the process more mindfully and with self-compassion.

Now let’s talk about how to declutter these so-called “it’s-complicated” objects…

1. Can you separate the item from the person tied to the item?

Remember, letting go of an object doesn’t mean you’re letting go of a memory or a person. Take a moment to reflect on the story behind the item, and acknowledge the significance it holds. Sometimes, writing down the memory or taking a photo of the item can be a powerful way to keep the sentiment while freeing up physical space.

For:

“1. An object could represent a person or ancestral idea we care about, however the object may not fit our personal tastes.”

Try This:

For each item, jot down a few sentences in a notebook about why it represents someone or something important to you. This creates a memory log, so you can revisit the sentiment without holding onto the item itself.

2. Honor the item’s intention

It’s easy to feel obligated to keep gifts, even if they no longer serve a purpose. Remind yourself that the purpose of a gift is to bring you joy simply from the act of gift-giving itself. If it’s only causing stress or guilt to hold onto the item, it’s okay to let it go. The giver likely wanted you to feel happy—not burdened—by their gift.

For:

“2. An object could be tied to someone or something we love, but the object is not useful for our current lifestyle.”

Try This:

If you’re close to the giver, consider letting them know you’re passing it on in a way that honors the gift’s value. For example, “I’ve appreciated this gift so much, and now that I’m no longer using it, I’m sharing it with someone who needs it more.”

3. Reframe high-cost items as lessons, not mistakes

Expensive items can be tricky to part with because they remind us of the money spent. But sometimes, we hold on to them out of a sense of “sunk cost”—we feel we must keep the item because of its price, even if it no longer fits our lifestyle. Recognize that holding onto something out of guilt doesn’t change the past cost. Not to mention it’s taking up space rent-free–is it worth the space it occupies in your home?

For:

“3. An object could represent a large investment that we regret making.”

Try This:

Instead of viewing it as a financial mistake, consider it a learning experience. Ask yourself: “What did I learn from buying this?” Whether it’s a shift in taste, a more discerning shopping habit, or a reminder of what matters most to you, take the lesson and release the guilt.

4. Embrace the idea of “functional legacy” for heirlooms

Heirlooms often come with a sense of duty and responsibility, especially if they’re family items. But if these objects don’t serve you or if they’re stowed away out of sight, it might be time to consider passing them along in a way that preserves their value to someone else.

For:

“4. An object could be important to our family, and we ended up with it, but it doesn’t fit because it simply isn’t important to us.”

Try This:

Consider offering the item to another family member or donating it to a place where it can be appreciated. Alternatively, repurpose it in a way that aligns with your current life (e.g., turning grandma’s quilt into a wall hanging). That way, you’re giving the heirloom new life while preserving its legacy.

5. Donate with intention

Parting with an item can feel much easier when you know it’s going to someone who will appreciate it. Consider donating to a cause that resonates with you. Knowing that your item will have a second life and bring joy to someone else can help lessen the guilt.

For:

“5. An object could represent an aspect of life that we think we should have, but it actually doesn’t represent our values.”

Try This:

Research local charities that accept special items, like women’s shelters, art programs, or vintage shops. Some organizations even allow you to follow the journey of your donation, so you know it’s making a positive impact.

6. Focus on what you’re gaining, not what you’re losing

Decluttering can feel like you’re saying goodbye to a part of yourself, but it’s also an invitation to welcome new energy into your life. By creating space, you’re making room for new experiences, new memories, and a sense of clarity. Focus on the benefits that will come from a more open, clutter-free space.

For:

“6. An object could represent a life we strive towards, but never achieve.”

Try This:

Make a list of what you’ll gain by letting go: more room to display the things you love, a clearer mind, easier maintenance, and perhaps even emotional peace. Keep this list handy as motivation whenever you feel guilt creeping in. Besides, here you can translate “never achieve” to “haven’t achieved–yet.” It’s an important distinction.

7. BONUS: Trust that it’s okay to let go

One of the hardest parts of decluttering is giving yourself permission to let go. Trust that you are not letting go of what truly matters—relationships, memories, values. These reside within you, not within the items themselves.

Try This:

When you find an item difficult to part with, ask yourself if it aligns with the life you’re trying to create. If it doesn’t, let go, knowing you’re making space for things that do.

Sometimes letting go of things means encountering negative emotions like guilt. What’s more important is how we can harness those emotions to finally process our feelings and make positive change in our lives.

By approaching guilt-tied items with intention, empathy, and self-compassion, you can honor the past while creating room for your future. Every item you release is one step closer to a home—and a life—that supports who you are today.

Love yourself, and show others you love them, too (without holding onto physical baggage).

If you’re still struggling with the idea of letting go of things while experiencing negative emotions, it can help to have someone with you to process. Our KonMari-certified organizers are trained specifically to help you navigate this difficult task. Book a free phone consultation today, or check out our services page to learn more about how we can help.

Works Cited:

Brown, Brené. The Gifts of Imperfection: Let go of who you think you're supposed to be and embrace who you are. Simon and Schuster, 2022.