Decluttering Grief: Why Letting Go of Stuff Hurts So Much and How to Make It Easier

Decluttering is often portrayed as liberating, a way to simplify, free up space, and make life easier. Clear the closets, clear your mind, right? But for people facing major life transitions, the experience can feel anything but freeing. Downsizing after retirement, becoming an empty nester, or coping with the loss of a family member often brings up waves of unexpected emotion. Sorting through a lifetime of possessions stirs up memories and emotions that can paralyze your decision-making process.

If you’ve ever felt a lump in your throat while packing a box or an overwhelming sense of loss when parting with belongings, you’re not alone. Experts in mental health and home organizers alike agree that decluttering during big life changes is as much an emotional process as a practical one. Here’s why it feels so hard, and how to move through it with more clarity, self-compassion and support.

Why letting go hurts so much

Decluttering after a big life change can feel like reliving the loss you’re already navigating. Dr. Gregory Gasic, neuroscientist and co-founder of VmeDx, says there’s a reason for that. “Our stuff is emotional. It’s a piece of who we were, of the people we loved, and the roles we played. When we’re asked to let go of it, it can feel like losing a part of ourselves or saying goodbye all over again”, he emphasized.

That old armchair in the corner? It’s not just a chair. It’s the spot where you read bedtime stories and cuddled with your kids when they were little. Your wedding China you haven’t used in years? It’s a link to celebrations with people you might not have around anymore. Letting go can feel like erasing a part of your and their story. That’s why so many of us end up stuck, keeping things we don’t use but can’t seem to part with.

Kristie Tse, psychotherapist and founder of Uncover Counseling, reminds us that this is completely normal, and offers a good way of getting past it. “Our belongings often represent memories, relationships, or even aspirations we’ve held onto over the years. Recognizing that the value resides in the memory, not the item itself, is a crucial first step toward letting go.”

Steven Buchwald, managing director of Manhattan Mental Health Counseling, adds that this process is about more than just things. It’s about identity and meaning. “When retired or after a loss, people experience a crisis of meaning. What then? What now? The past is safer; our belongings enable us to remain there. Downsizing is a way of re-scripting your life history, drawing back from what no longer serves you to make space for what truly matters. It can be made easier by a therapist who helps you write a new script that honors loss but opens up space for meaning, rebirth, and expansion”.

Easier said than done, right? Which is why it helps to know you don’t have to do it all at once, and you don’t have to do it alone.

Why downsizing feels so overwhelming

Part of what makes this process so draining is the sheer scale of it. When you’re staring down decades’ worth of closets, drawers, and keepsakes, it’s easy to feel paralyzed. Add in deadlines (like a move) or the emotional weight of a fresh loss, and, suddenly, even filling a single box can feel impossible.

Laura Price, owner of The Home Organisation, sees this all the time. “Understanding the size of the project they face when it comes to decluttering is very important. Too often people leap in and try to take on far too much too quickly because they don’t understand how physically and mentally tiring it can be to sort through all of your things”, she explained. “Doing this with plenty of time in hand means you’re much less likely to suffer from those feelings of overwhelm and anxiety as your deadline gets closer.”, added Laura Price.

So, if you’ve ever abandoned a decluttering session halfway through, exhausted and frustrated, you’re not the only one, and you’re not failing. You’re simply human. The good news is there are ways to make the process gentler, more doable, and even healing.

Six ways to declutter without feeling like you’re losing everything

Being overwhelmed and feeling a sense of loss related to decluttering, particularly after a major change in your life, happens to almost everyone. Nonetheless, it’s a process we must go through, and usually more than once in a lifetime, so it’s important to have tools do to it in a healthy, positive way.

1. Slow down and honor the memories

This isn’t a race. Give yourself permission to pause and reflect. Dr. Gasic suggests creating small rituals to help you find closure. “Talk about the memories behind certain items. Take photos, write notes about them, or pass them along to someone who will value them. These small rituals ease the process, give a sense of closure and help you”, he added. When you shift the focus from “getting rid of things” to “honoring their place in your life,” the whole process feels less like a purge and more like a transition.

2. Think of it as preparing for the next chapter in your life

The word “decluttering” can feel cold in emotionally charged circumstances, as if everything you own is easy to toss. Laura Price suggests we should look at it from a positive perspective, as a much-needed preparation for the next chapter in our life. “Declutter little by little and allow plenty of time. Working through a lifetime of things takes time and rushing the process becomes stressful and overwhelming. It’s much better to do this over the course of several months, working through each room or category of things a drawer at a time”.

This mindset shift can turn an overwhelming project into a slower, more intentional curation of our future space.

3. Find support that won’t add pressure

Family can be a huge source of support when you’re sorting through things after a big life change, but they can also bring their own emotions and their own opinions about what you “should” hold on to. Sometimes their good intentions can make the process feel heavier, especially if they’re attached to items that don’t carry the same meaning for you. That’s where having someone neutral can really help. A trusted friend who isn’t as emotionally tied, a professional organizer, or a therapist can offer gentle, steady guidance without judgment. They can help you figure out what truly matters to you, not anyone else, and make the process feel less overwhelming.

4. Give yourself breathing space with self storage

If you feel backed into a corner to make decisions, a self storage unit can be a lifesaver. Joshua Davis, Senior VP of Operations at StorMark Self-Storage, says this simple step often brings enormous relief. “What helps many people is permitting themselves to take the process slowly”, he notes. “Temporary self storage can offer a practical buffer. It allows people to clear space in their homes without feeling forced to make permanent decisions. That sense of flexibility often brings emotional relief, making it easier to sort through belongings with a clear head and at a manageable pace.” Sometimes, just knowing your items are safe while you work through emotions can make the process far less overwhelming.

5. Listen to your body

Our emotions don’t just live in our minds. They show up in our bodies, too. According to somatic therapist Amy Hagerstrom, that’s why the process of decluttering during a major life change can feel so physically draining. “When clients face major life changes like empty nesting or retirement, their body literally interprets letting go of belongings as losing pieces of themselves”, she says.

That’s why it’s important to notice the physical signs of stress, things like shallow breathing, chest tightness, or stomach tension. When such signs appear, Amy Hagerstrom recommends that we take breaks to ground ourselves. “Taking breaks to feel your feet on the ground or wrapping yourself in a blanket can help your body feel secure enough to continue. Start with items that create the least body tension first”, she explained.

According to her, our bodies need repeated experiences of “I can let go and still be safe” before it will allow us to release more meaningful possessions. Pausing and grounding yourself helps you keep moving forward without getting stuck.

6. Learn how to hold on to the essence of things and what they represent

Kym Tolson, therapist and founder of The Traveling Therapist, knows firsthand how emotional this process can be. When she sold nearly everything she owned to travel full-time, she worried she was losing her sense of self. What helped her get through it was a simple ritual that everyone in the same situation can replicate. “Before decluttering each category, write down three skills or values that category represents about you, then find one small item that captures those qualities to keep. When I sold my furniture, I kept one small lamp because it represented my ability to create cozy, healing spaces. It’s something I still do in Airbnbs and hotels as a traveling therapist”.

Making space for what’s next

Downsizing will probably never be easy, but it doesn’t have to feel like one long goodbye. Ashley Peña, executive director of Mission Connection Healthcare, offers a different perspective, one that centers around healing. “By pausing to honor the story behind each item and involving supportive people, downsizing can become a healing process rather than a painful one. It’s not just about clearing space; it’s about making room for what’s next”.

If you’re facing challenges related to decluttering during a life event, remember to be gentle with yourself. Go slowly. Get help where you need it. And remember that letting go isn’t about erasing your past. It’s about carrying the most meaningful pieces of it forward as you step into your future.