Have you ever stood in your attic or basement, decluttering box in hand, motivated to finally make progress decluttering your stuff, but then begin hesitating over actually making decisions?

Maybe it’s a certain category of items (books, hobby supplies, sentimental items). Maybe it’s items that just carry a heavier emotional weight than others. Or maybe you find yourself unsure about decluttering anything and everything.

Well, your situation and response are not unique. The process of removing clutter can be both physically and emotionally draining. But that doesn’t mean you should stay there—stuck.

There may be some items that are more difficult than others to minimize, but that doesn’t mean we should give up on the process—especially if there is a better life available to us after the work is done.

So, to get you started, here are five questions to ask yourself when decluttering feels tough:

1. Does this item align with my present, or am I holding onto it because it was part of my past?

Marie Kondo says it this way, “The space in which we live should be for the person we are becoming now, not for the person we were in the past.”

Life is a journey, and the seasons of our lives change continually.

An item that once held great significance or brought great joy might not hold the same value now. Whether it’s a hobby-related item from a pastime you no longer pursue, or mementos from a chapter of your life that has closed, it’s important to evaluate whether these items still have a place in your current and future life.

Holding onto too much of our past can sometimes prevent us from making the most of our present and future. I’m thankful for my past, I’m just not moving in that direction—and neither are you.

If the item no longer aligns with who you are and where you’re heading, perhaps it’s time to let it go.

2. How often do I use or enjoy this item?

The true value of an item lies not in its cost, its rarity, or its ‘potential’ use, but in the enjoyment and value it brings into our life.

If an item sits unused and unappreciated, it’s not contributing value. Even worse, it is taking away from our potential.

So, whether it’s clothes we never wear, gadgets we never use, or books we never read, unused items can take up space and energy. There’s nothing wrong with holding onto a few items that aren’t used regularly, but boxes and boxes of unused things become a drag on our potential.

So, if the item isn’t used or enjoyed regularly, it might not be as valuable to keep as you think.

3. If I were shopping now, would I buy this?

This question can provide a fresh perspective and help us make new, objective decisions.

Imagine you’re at a store, looking at the item for the first time. Would you buy it? If not, why?

This can help us realize that we might be holding onto items due to a sense of obligation, guilt, or the endowment effect, rather than their actual value to us.

If you wouldn’t choose to bring this item into your life today, it might not be worth keeping.

4. Would allowing someone else the opportunity to use this item breathe more life into it?

Think about the book you’ve read and loved, the dress you wore once, or the tool you rarely use. These are all items that could be life-enhancing to someone else.

In fact, the very thing you are struggling to declutter and allowing to collect dust on your shelf may be the very thing someone in your community is praying for—especially when you think of items that can be used by young families with young children struggling to make ends meet.

If you’re not fully utilizing or cherishing something, consider gifting it a new life with someone else. This thought can make letting go easier and more fulfilling.

In this way, decluttering stuff can be about more than just discarding, it’s redistributing for better use of resources.

5. Is the emotional or financial cost of keeping this item worth it?

Every item we own comes with a cost. It could be a financial cost, like maintenance or storage fees, or an emotional cost, like stress or guilt.

It might be a photo album that brings up painful memories, or an expensive item you never use but feel guilty getting rid of.

We often underestimate the mental and emotional burden of clutter—it can drain our energy, distract our attention, and weigh on our minds.

If the cost of keeping the item outweighs its value to you, it might be time to let it go.

Sometimes we want to keep items from a past season of life that we loved… other times we hold on to items from a past season of life that we wish had turned out differently. In either case, the emotional distraction is a wage that we pay every time we see the item. Free yourself.

Like I mentioned earlier, decluttering can be difficult at times. And different people struggle with different categories of possessions to minimize.

And while these five questions may not solve every difficult decision you have to make on your journey to owning less, I believe they form a strong foundation for starting to think differently about your stuff—especially those items that are hard to part with.