Why is Decluttering So Hard? 7 Reasons You're Struggling to Get Rid of Your Stuff

Posted in Organization on Sep 14, 2022, tagged with decluttering

Why is Decluttering So Hard? 7 Reasons You're Struggling to Get Rid of Your Stuff

Decluttering makes cleaning your home and staying organized easier—having fewer belongings means less stuff to clean and keep organized—but the act of decluttering itself can be more challenging than any of us expect. 

So, why exactly is decluttering so hard? If you’re struggling to get started or you’re stuck staring at a fresh pile of “decluttered” belongings, you’ll be thrilled to learn there are multiple factors that go into why parting with your prized possessions can be so hard, including:

  1. The reason why you’re decluttering
  2. How we view our belongings
  3. They are associated with good memories
  4. They are associated with bad memories
  5. It was free
  6. We spent too much money on them/the item(s) are aspirational 
  7. Consumer culture

Now, let’s dive into these different factors and see how they complicate clearing out your stuff. 

1. The Reason Why You’re Decluttering

While there are many reasons you may be decluttering your belongings or someone else’s, the circumstances surrounding the act of decluttering can be stressful on top of an already stressful and emotional situation. This is especially the case if you’re decluttering ahead of a local or long distance move or you’re downsizing yourself or a loved one to prepare for a smaller home.

If you’re the one moving, your reason for relocating may be positive, such as a new job or another exciting opportunity. But even though the reason might be a good one, you often won’t be able to bring everything you own with you, especially if it is a long distance move or the timeline is short. Parting with items before you are ready to part with them is an emotional experience that can be difficult for the many reasons outlined below. And if the reason you’re moving isn’t joyful, decluttering your prized belongings can add even more stress to an already difficult time. 

When it comes to transitioning a parent or other loved one into a retirement community, long term care, or nursing home, decluttering can place a lot of additional strain on everyone involved and trigger powerful emotions and even early grief. While your loved one may not be dying or even sick, downsizing is an acknowledgement that they are getting older and their lives are changing. They’re moving into a different stage of life and getting rid of many special items, and these types of transitions are never easy.  

How to Overcome This Hurdle:

In some cases, seeking the help of a professional organizer can help you (or your loved ones) work through the decluttering process, especially if you’re moving long distance, relocating on a short timeline, or downsizing yourself or a loved one. Learn more about the benefits of working with a professional organizer: 

2. How We View Our Belongings

Sometimes, getting rid of things is difficult because we’ve imbued the item with emotional meaning. It has become part of us and our identity, or the identity of someone important to us, and as such, it is valuable and hard to part with. 

Time and care spent on an item are essential ingredients in making something yours. If an item has been in your possession for a long time or it’s something you care about, it is harder to part with, even if it’s not unique. It’s unique and special because it is yours. 

How to Overcome This Hurdle:

The KonMari method works well here—keep what is still useful or sparks joy, and get rid of everything else after taking a moment to thank it for its contribution to your life.

3. Good Memories

It’s hard to part with items that are tied to your best memories, whether they’re ephemera such as concert tickets, menus, or notes, or more substantial tchotchkes such as figurines or items you collected while traveling. 

If you aren’t someone who scrapbooks, these items can just sit around in boxes for years. This is ok—not everything needs to be on display!—but it’s important to get them organized. Sort through these items and figure out which ones are truly important to you and which ones might be important to others in your life, then recycle or donate the rest. 

How to Overcome This Hurdle:

Once you have sorted, take a page from the Gentle Art of Swedish Death Cleaning by Margareta Magnusson and place these items into designated boxes clearly labelled so that, after you die, people know who gets what, or whether or not they can just chuck them.

4. Difficult Memories

While you might think getting rid of items that trigger painful memories would be easy—after all, wouldn’t you be happy to get rid of and forget those moments?—it can be just as difficult to part with them as it is to get rid of items that trigger happy ones. Depending on the circumstances, it might even be more difficult to get rid of them. 

How to Overcome This Hurdle:

Getting rid of items that trigger difficult memories for you often requires working through your feelings around the situation, and sometimes you just aren’t ready or you may need some professional guidance to navigate the situation.

5. It Was Free

There is some interesting psychology that takes place when we receive a free item, whether it is something you picked up at a conference or something given to you by a friend or family member trying to declutter their own belongings. 

How to Overcome This Hurdle:

According to Psychology Today, not only is it difficult to turn down a free item, “when we take something that's free, we typically feel obligated to use or hang onto it.” Keep this in mind when you are decluttering and try to free yourself from the guilt of getting rid of free items.

6. Expensive and Aspirational Items

It’s easy to get caught up in the moment and overspend on something. And then, due to bad return policies or love for the item, you don’t return it. Maybe it’s too expensive or nice to use every day, but eventually you will use it...then for whatever reason, the right event or situation never arises, and it sits unused for years. Sound familiar?

How to Overcome This Hurdle:​​​​​​

It may seem pretty straightforward that you need to get rid of this item, but it just cost so much money. In this instance, you may be better off selling the item in order to recoup some of the expense. If it was an aspirational purchase, you may need to come to terms with that before you can get rid of it.

7. Consumer Culture

We live in a society where we consumers are intensely studied and scrutinized by scientists and marketers in order to convince us to part with our money in exchange for goods and services. 

In many circumstances involving a purchase, your decisions are subtly (and sometimes not-so-subtly) influenced. In-store or online, you have been placed in a very carefully orchestrated environment designed to encourage spending. According to Psychology Today, marketers work to address a “consumer’s core needs: control, pursuit of happiness, identity, and social belonging.” And they accomplish this so effectively that, once you have purchased an item, it can be more difficult to part with it later as a result of their efforts. 

How to Overcome This Hurdle:

Since we have very little control over many facets of this interaction, this can be one of the most difficult hurdles to overcome. Simply being aware of the influence can make it easier to separate yourself from these belongings and ultimately part with them. Eventually, considering this dynamic and how it affects you before you make a purchase can help you resist accumulating items you don’t need.


There are many reasons why getting rid of belongings can be difficult:

  1. The reasons that prompted the decluttering
  2. How you view your belongings
  3. The memories associated with them are good
  4. The memories associated with them are bad
  5. It was free
  6. It was expensive or aspirational 
  7. Consumer culture and psychology

Coming to terms with and moving past these snags can be challenging, but knowing why it is hard to part with an item can make it easier to decide what to do with it. 

For more advice on decluttering and organization, try these other Outside The Box posts: 

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