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Letting Go: Practical Steps to Overcoming Hurdles

Updated: 5 days ago

In our journey towards a more organized and serene living space, we often encounter hurdles in the decluttering process. Some hurdles are emotional- we feel guilty letting go of things that remind us of special memories or people. Some hurdles are financial- we spent money on these items, and it’s wasteful to get rid of them. Some hurdles are obligatory- items have been inherited or received as a gift so I have to keep them. Some hurdles are “just in case”- maybe we will need these items in the future so let’s keep them. The attachment we feel can make decluttering a daunting task. However, there are some practical steps that can be taken to help overcome these organizational hurdles and to begin the letting go process of the organizing journey. 


1. Know Your Why

What is your organizing goal? What is your motivation to get organized? Is it to be able to find things in your closet more easily? To reclaim your kitchen table as a table and not a dumping ground?  Knowing why you want to get organized will help you stay focused on your goal when faced with the inevitable tough decluttering decisions.


2. Shift Your Mindset

Try changing how you perceive your belongings. Instead of seeing them as permanent fixtures in your life, view them as temporary companions. Their purpose was to serve you for a specific time, and it's okay for their role to end. If the items are in good shape, donating them will give them a second life with someone who really needs them.


3. Start Small, and Start Easy

First, begin with a small area. Tackle one shelf instead of the whole closet, or one drawer instead of the whole kitchen. By starting small, you build confidence and create momentum, making it easier to tackle more challenging areas later on. Second, make sure the area is “emotionally neutral” and not filled with items that you would have a hard time letting go of. Bathrooms and kitchens are a good starting point since those items typically don’t carry great emotional weight. 


4. Go At Your Own Pace

The clutter didn’t accumulate overnight, so it doesn’t have to disappear overnight. Getting over decluttering hurdles can take time, and some people will take longer to make decisions on what to let go of than others. Don’t think you are failing if the project is taking longer than you expected. Slow and steady progress will get you to your goal.


6. The 20/20 Rule & Other Questions

If you are struggling to let go of an item, ask yourself if it can be replaced in less than 20 minutes for under $20. If so, consider letting it go. Other questions you can ask yourself to help make the decision process easier are: When was the last time I used/needed this? Can the item be donated to help someone else? Would I purchase this item if I didn’t already own it? Is it the memory or the item that I want to hold on to? 


7. Create a Maybe Box

For items you’re still on the fence about, place them in a box labeled with a date. If you don’t retrieve any items from the box within six months, donate or discard them. This gives you time to detach emotionally without the pressure of immediate decision-making.


8. You’re Not Losing Clutter, You’re Gaining Space

Shift your focus away from what you’re losing to what you’re gaining. Appreciate the space, clarity, and peace of mind that come from a decluttered environment. If your emotions arise during the process, remember your goal! Take breaks as needed, and even go for a walk to clear your head. Engaging in a few minutes of meditation can help relax and calm if the process becomes too overwhelming. 


Dealing with Specific Types of Hurdles


1. Sentimental Items

Sentimental objects or other emotionally charged items are some of the hardest decision hurdles to overcome. Take photos of these items and create a digital album. Digitizing is a great way to help you preserve the memory without keeping the physical object. Another way is to repurpose the sentimental item into something useful. Old t-shirts can be made into a quilt, and a few cherished children’s art pieces can be framed and hung up. Designate a specific box for items you would like to keep, but once it’s full, you’ll need to decide what stays and what goes.


2. Financial

If you have items with some monetary value, and the time and desire, it might be worth trying to sell online, at a garage sale, or to a thrift store. This can help alleviate the “I spent good money on this” guilt by recouping some financial return. However, sometimes it is best to just accept that the money spent is a sunk cost and donate the items. Keeping things you don’t use or love won’t bring that money back. 


3. Gifts and Inherited Items

Recognize the giver’s intention and appreciate their thoughtfulness, but separate the object from the emotion. Understand that the item itself doesn’t define your relationship with them, and discarding the item does not mean you are discarding their feelings for you. It often helps to have an objective third party involved in the process. If possible, try to prevent an unwanted or unneeded item from even entering your home. “Thank you so much for thinking of me, but I already took the things that remind me most of Aunt Betty.” Donation to a good cause is always a great option. Knowing that the item will be useful and bring joy to someone else makes the letting go process easier.


Embracing a Life with Less


Overcoming the decluttering hurdles that have held you back for so long is something to be celebrated. These small, practical steps not only help you achieve your goal of decluttering but also help to create new habits and a shift in your mindset about releasing items. Remember, the goal of organization is to create a living environment that supports and nurtures your well-being. Letting go of clutter and simplifying your space is the best way to accomplish that goal.



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