3 Reasons Why It Feels Scary Letting Go of That
We all tend to acquire things and then hold on to them; letting go is difficult! Some of us have a greater tolerance for the amount of clutter in our spaces than others. When the volume of things we’ve acquired starts to impact our lives, making it difficult to do the things we love or causing tension in our relationships, we may decide to take a look at how much we have and begin to sort and release some of them. Even when we think we’re ready and motivated to let some of the abundance go, it can feel overwhelming to make decisions and release our treasures.
Here are a few reasons why it can be tough, along with some ways to practice letting go so that it becomes easier. (Notice I didn’t say easy.)
When it feels like we’re losing out on our investment
Most things cost money. Many of us work very hard to earn our incomes, and we attempt to maximize our purchasing power. Sometimes, we invest a considerable amount of time researching a purchase or searching for a specific item. The more time we spend researching or looking, the greater our attachment to the item becomes even before it’s in our possession.
Letting go of an item that we’ve acquired through this type of effort, whether through donation or resale at a lower price, can feel like we’re losing out on our investment.

So, how do we take on this feeling of losing out on an investment? We practice dealing with this loss by starting small. Donating a blouse that I waited to purchase until it was 40% off and only cost me around $25 is going to be much easier than selling the vehicle I researched for three months before buying, which was below book value. Practice makes progress, so we start with things that have smaller levels of attachment to them as we begin, and then we move to items that are “stickier,” as I like to call it.
It’s also important to recognize that there are times when a firm, helpful decision feels bad (remember how you felt after going to the gym for the first time in January…yet you went back again, right?). We must challenge our assumption that when something “feels bad,” a term called emotional reasoning, it means we need to avoid the action associated with it.
When letting go of an item feels like we’re losing a memory
Many of us save items that have very little monetary value because the items trigger memories for us. I still have a keychain that served as a ticket to a homecoming dance I attended in high school. When I take down my small box of memories and hold this keychain, I’m transported back to a darkened lunch room, and I can remember dancing with friends and getting dressed up.
Sometimes, we rely too heavily on the presence of items to trigger memories. Sometimes, we forget an experience until we stumbled across an item that triggers a memory. When both these conditions exist and living our lives freely is compromised by holding onto memory triggers, it may be helpful to practice letting go.
Holding onto a few key items from significant events isn’t an issue. Many people have the hat their infant wore coming home from the hospital, a copy of their wedding invitation, or the “lucky” socks they wore when they led their team to that big victory. Yet, holding onto receipts to remember that coffee date with our good friend or picking up free pamphlets at every stop on our last vacation can create clutter.
We can practice letting go by choosing a few items that are newer (and thus less sticky), thinking about the experience we have associated with the item, and retelling the story of the event and the people involved. By putting the item out of sight, such as in another room, we can return and retell our memory without the item in our hands or our line of sight, reaffirming our ability to recall the event the item has triggered. Each time we practice the memory without the trigger of the item, we strengthen the memory, making it less likely that we’ll forget it in the future.
It’s essential to note that very few people possess such high-capacity memories that they recall everything. (Check out this article about eidetic and photographic memory.) Most of us are bound to forget key details when the phone bill is due without a reminder, or even where we put that oddball phone charger we found hidden in the couch.
When we’re not sure if we can find/replace the item in the future
In a culture of fast fashion and mass-produced, low-cost items, there is something about certain unique items that makes them difficult to release. Artists number their prints and only produce a limited number, hoping that this scarcity will increase the value and the desire to acquire and preserve their work. Books go out of print. Automobile manufacturers cease to build specific models of vehicles (goodbye Taurus and Malibu!).
Sometimes, the items aren’t as rare or unique, but our concern is that there could be a change in our ability to purchase an item in the future. Many stock up on hobby supplies in the last year or two in the workforce before retirement because they recognize their purchasing power will be reduced in retirement. These are real concerns that can make it difficult to part with items. Yet, if we save every item that we might not be able to reproduce, reacquire, or afford in the future, our lives and homes are destined to become unmanageable.
How do you take steps to manage better? We challenge our current use of items. If something hasn’t been used in years and we’re holding onto it for the potential of future use, we’re better served by acknowledging the uncomfortable emotions about how we didn’t follow through on our plans. (This is something that comes up for me about books. My books tend to tell me not-so-nice stories: how I was going to read them.) We also need to have a clear sense of our values and identity. Identity based upon possession without the use of an item is a house of cards. Saving items that don’t align with our values will ultimately cause distress and impair our ability to make informed decisions. At times, we need to take the time to determine our values before deciding what to keep and what to release.
Key Takeaways
Everyone has some level of attachment to the things in their home; that’s why those items are there. When items become superfluous and cause personal distress or conflict in our relationships, it may be time to consider practicing letting go.
Practicing letting go is like any other skill. It takes practice. We start small with items that evoke some level of distress and release them, learning in the process that we can do more than we often believe we can. Over time, we can increase the amount of distress we can tolerate through this practice. The goal isn’t to release everything or to make only uncomfortable decisions. The goal is to lead lives in safe, open spaces for what matters most to us.
Do you think you have too many things and find letting go difficult? Consider learning more about my background and how I can help.
