The most difficult part of simplifying your life is decluttering sentimental items. It’s the final boss of all types of decluttering because it’s really hard to stay grounded when you’re dealing with the complex emotions associated with your possessions.

Sentimental items often hold significant emotional value because they are connected to important people, events, or periods in your life. They serve as tangible links to the past. These items can evoke feelings of nostalgia, love, happiness, and even sadness, in different quantities—and sometimes even at the same time.

Decluttering, especially when it involves letting go of sentimental items, is not just a physical task but an emotional one. It's about more than just clearing out space; it's a conscious decision to curate our belongings and, by extension, our what feels like our memories and sense of self. Many people find this process daunting because it challenges them to confront their attachments and the emotions tied to these objects.

In this post, I’ll cover why it's so hard to part with sentimental items and offer practical strategies for navigating this process. Whether you're downsizing, simplifying your life, or just trying to create a more organized home, understanding the complexities of letting go can make the journey a little easier and more meaningful.

Why It’s So Hard to Let Go of Sentimental Items

To start, let’s take a look at why it’s so hard to let go of sentimental items:

1. Emotional Attachment

Holding onto sentimental items can be a way of holding onto the past. It can be comforting to keep reminders of happy times, loved ones, or significant achievements. Letting go of these items may feel like letting go of the past, which can be unsettling.

2. Sense of Self

Sentimental items can be closely tied to your sense of identity and personal history. They may represent accomplishments, efforts, relationships, or significant life changes. Letting go of these items can sometimes feel like losing a part of yourself.

3. Fear of Losing Memories

Many people worry that getting rid of an item will mean losing the memories associated with it. Physical objects can serve as tangible reminders of past experiences, and there is often a fear that without them, the memories may fade.

4. Guilt

You may feel guilty about discarding gifts or heirlooms because it might feel like you are disrespecting the person who gave them to you or the memory of a loved one. This guilt can make it particularly challenging to let go of sentimental items.

5. Cultural and Familial Expectations

Cultural norms or family traditions may place a strong emphasis on preserving family heirlooms or other sentimental items. This can add a layer of obligation or pressure to keep these items, making it harder to let go. This is similar to guilt—and can involve guilt—but comes from an external source.

6. Fear of Regret

There is often a fear of making the wrong decision and regretting it later. The concern that you might miss the item or need it in the future can create anxiety. This is especially difficult in sentimental items as we see them as unique and irreplaceable.

7. Avoidance of Grief

In some cases, holding onto sentimental items can be a way of avoiding the full process of grieving a loss. Letting go of these items can feel like letting go of the person or relationship they represent, which can be a painful experience.

8. Comfort

Sentimental items can provide a sense of comfort and security, especially during times of change or uncertainty. They can serve as a link to stable and positive times, providing emotional support.

The first step to getting rid of sentimental items you no longer want is to get to the root of why you’re holding onto them. This can help you approach the process of decluttering with more empathy and self-awareness.

Strategies for Letting Go of Sentimental Items

I see decluttering, especially that of sentimental items, as a practice rather than a one-and-done situation. As we’ve discussed, these complex emotions require time, patience, and a lot of introspection. As much as it would be great to magically declutter everything in one go, the reality is that decluttering is a muscle that needs to be built.

Below you’ll find the strategies I have in place to help me in my decluttering practice, specifically when it comes to sentimental items.

1. Get Clear on Your Why

Reflect on why you're decluttering. Whether it's to create more space, simplify your life, or reduce stress, keeping your goal in mind can help you make decisions about what to keep and what to let go of. Write it down or find an image that represents your why and stick it somewhere within sight while you’re decluttering. Whenever you find yourself struggling, remind yourself of that “why.”

2. Set Limits on How Much Stuff You’ll Keep

Decide how much space you're willing to dedicate to sentimental items. For example, you could limit yourself to one box or one drawer. This can help you prioritize the most meaningful items. One of my favorite things to think about (as you’ll also hear me wax poetic about in the photos module in my digital decluttering course) are those scenes in movies where someone discovers a small box of keepsakes that belonged to their parent or grandparent; each item is just that much more precious.

3. Start with the Easy Stuff

You don’t have to declutter everything immediately; this is a practice. Even within your sentimental items, some are more sentimental than others. Begin with less sentimental ones, and put the tough ones aside for later. This will help you build momentum and get used to the process of letting go. As you gain confidence in your practice, you can move on to increasingly emotionally charged items.

4. The “Maybe Box”

Speaking of putting things aside, if you know you don’t want something but you’re also not quite ready to let the item go, put it out of sight for a little while as you learn to declutter. I have a “maybe box” for this. It’s an intermediate drop zone where I can put items that need a bit of a cooling-off period. Part of the thinking here is that you’ve already acknowledged that you want the item out, and you’re getting used to the idea without actually committing. I would advise you to limit the size of the maybe box and to go through it and actually get rid of stuff once it fills up.

5. Understand It’s Not the Item

The memories associated with an item are more important than the item itself. You can keep the memories without keeping every object. The memories live inside us and are only sparked by the object. If you’re worried about forgetting, a photograph of the item or a written note about its significance can be enough. This way, you can preserve the memory without holding onto the physical object. I find this thought especially useful when dealing with the guilt that comes with decluttering; it’s not the item, it’s something within me.

6. Repurpose or Transform the Item

The sad reality about a lot of our sentimental items is that they sit in the back of closets, basements, or attics gathering dust. That makes it hard to enjoy them and their memories. Consider turning sentimental items into something useful, something you actually want to display or at least not store so far out of sight. For example, you could create a quilt from old t-shirts or compile letters and cards into a collage.

7. Give It to Someone Who Will Appreciate It

If certain items are in good condition and might be valuable or meaningful to someone else, consider gifting them. Knowing that the items will be appreciated can make it easier to let go of them. Of course, don’t push these items on people who hesitate or don’t want them (I see family members do this way too often).

8. Get Support

If you find the process overwhelming, consider getting help from a friend, family member, or professional organizer. They can offer a fresh perspective and support you through the decision-making process, which is exhausting.

9. Practice Gratitude and Acknowledgement

Acknowledge the role these items have played in your life, express gratitude for the memories they represent, and then release them. It’s a simple mental exercise, but it can really help lift a lot of the discomfort that comes with letting go. On top of that, it helps give closure and once again, helps you deal with the guilt of letting go.

10. Be Kind to Yourself

Decluttering sentimental items can be emotionally taxing. It's okay to take your time and to be gentle with yourself throughout the process. This practice can bring up a lot of unresolved emotions you might not even realize you had. You might cry, laugh, shout, hate, or love. All of these reactions (and more) to decluttering sentimental items are valid and part of the process of letting go.

The Benefits of Letting Go of Sentimental Items

I’ve spent most of this post talking about how hard it is to let go of sentimental items, and that might be a bit discouraging. The benefits of decluttering sentimental items might be few in number, but their impact makes the often painful process so worth it.

Emotional Freedom

Letting go of sentimental items can be a liberating experience. Often, we don't realize the emotional weight these objects carry until we start releasing them. By decluttering, we free ourselves from the physical reminders of the past that may no longer serve us. This act can alleviate feelings of being overwhelmed, reduce stress, and create a sense of emotional clarity. The space we clear in our physical environment often translates into mental and emotional space, allowing us to focus on the present and future with a lighter heart.

Preserving Important Memories

It's important to remember that decluttering doesn't mean erasing memories. By choosing to keep only the most meaningful items, we honor our past in a more intentional way. This process encourages us to reflect on what truly matters and helps us cherish the most significant moments and connections. By curating a collection of truly important items, we preserve the essence of our experiences and make it easier to revisit these memories when we want to.

Creating Space for New Experiences

As we let go of the old, we make room for the new. Decluttering sentimental items is not just about discarding; it's about making space for new opportunities, relationships, and experiences. Holding onto too many things from the past can sometimes prevent us from fully engaging with the present. By decluttering, we create a physical and emotional environment that is conducive to growth and new beginnings. This newfound space can lead to a more open and adaptable mindset, welcoming change and nurturing personal development.

Final Thoughts

Decluttering sentimental items is an incredibly challenging process, but it can also be deeply rewarding. It's important to approach this practice with compassion and understanding, both for yourself and the memories these items represent. Use this practice to get to know yourself more deeply, to explore the tender side of your soul.

The fact that you have sentimental items is a beautiful thing; it shows that you care. While I still encourage you to let go of excess, it's perfectly okay to keep some sentimental items—especially those that bring you joy and comfort. The key is to find a balance that allows you to cherish the past without being weighed down by it.