What To Do When You Aren’t Sure Whether To Keep It Or Give It Away

July 8, 2015

No matter how genuine your intentions to Simplify your life, or how focused your approach, it’s still possible that at some point during your editing process you’ll hit the roadblock of doubt; should you keep it or let it go?

Here, just for you, are some of my Simply-est strategies for helping you find the right answer when you’re on the decluttering fence.

these simple tips are a roadmap out of getting stuck making decisions when decluttering!

1. Let your stuff duke it out.

I find that my clients always have an easier time making decisions about their belongings when I ask them to evaluate single items in relation to larger categories or like items.

Some things you know instantly, and on a one-by-one approach, whether or not you love. When it comes to items that you feel less definite about, it’s helpful to consider how they compare to other, similar things you own in your mind.

If you’re hung up on a dressy top, hold it against the other dressy tops you own. Do you love it as much as the ones you’ve chosen to keep? Are there ones among your keepers that you will inevitably choose to wear over it?

The point is always to establish your spectrum. By identifying which items immediately fall on the LOVE end of the spectrum for you, and which fall on the WHY DO I STILL HAVE THAT BYE spectrum, it becomes much easier to determine which way that item-in-question leans as compared to the others.

2. Screen it further

The most important deciding factor in whether or not to keep something is if it excites you, brings you pleasure, and gives you life-energy, or, on the other end of the spectrum, if it drains you, makes you feel stuck, stalls your progress, and brings up feelings of worry or fear.

But, if you’re finding it particularly challenging to hone in on which of the two sides an item you’re considering falls on, return to these five questions.

these simple tips are a roadmap out of getting stuck making decisions when decluttering!

3. Put it in the donate pile. Immediately.

This isn’t a manipulation or any sort of trickery; I hardly know what the item in question is over which you’re deliberating, so I’m definitely not on a crusade to see it go.

But here’s the thing: the absolute hardest part of the editing process comes just before you decide to let something go. That’s the moment when all those thoughts of worry or guilt bubble to the surface, trying their darnedest to cloud your judgement.

Once you decide to let something go, that decision releases you, and with each passing second and minute after you’ve deposited an item into the donation pile, your attachment to it wanes.

If you come across an item that really stumps you while editing, bite the bullet and put it in the donate pile. It doesn’t have to stay there! It’s more like an experiment in this case.

Give the questionable item a solid 3-4 hours (at the minimum) to simmer amongst the giveaway items. Those hours will be crucial in helping you determine whether your need for and attachment to the item is still real and lasting, or whether it was merely about facing the difficult decision of releasing it, and nothing more.

If, after that allotment of time has passed you decide that, in fact, you still do want the item, go ahead and retrieve it. My clients occasionally do this and–far from being disappointed in them–I’m happy to see them reach a place of clarity.

To Live Simply you need to make thoughtful decisions, not rashly get rid of everything without adequate consideration.

If, in the end, you realize that you’re comfortable letting go of the item you were questing, leave it in the donate pile. Let it go, and move on.

these simple tips are a roadmap out of getting stuck making decisions when decluttering!

4. So like, can’t I just put the ones I’m not sure about in the “Maybe” pile?

I’m not a big proponent of the “Maybe” pile, on the whole.

Here’s why:

Psychologically, putting something in a maybe pile does not inherently bring about any clarity. It only reaffirms for you that you’re on the fence about those items. This means that when you go back to that pile (if you do) you may not have reached any decision about the items within in the interim.

The “Maybe” pile is, more often than not, a euphemism for the “Let Me Deal With This Later,” pile and the “How Can I Avoid This Decision For Another Couple Minutes?” pile.

So although it may cause some trepidation, placing items you’re wavering on in the donate pile now will help you gain much more clarity in the end.


Because the hard truth is that when it comes to belongings, things are either a YES, or they aren’t.

In almost all cases, the presence of doubt and over-thinking and deliberating is illustrative, in itself, of the fact that whatever the thing in question is doesn’t automatically inspire a Yes. Love it.

And since Live Simply is about having only YES/LOVE IT things around you, well, you can bet how this story ends.


Image credits: stock, Apartment Therapy, unknown






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