25+ Questions To Ask If You’re Stuck Letting It Go

Mar 25

In my years of helping people declutter, we occasionally work with those who have a deep emotional attachment to items…or they just struggle with “what if I need this later??” thoughts. Most of the time, when a person contacts us they are ready to part with the stuff that’s causing stress. But there’s times when families struggle to let go of something…or many somethings. In those situations, which I am not immune to myself (really…who is?!), I have a list of questions that can help move along the process. If you’re stuck letting go, here’s 25+ questions that might help in your efforts.

With spring cleaning and decluttering on the mind, I thought it was time to share these with you!

Don’t get me wrong, I am not the type to push someone to let go … even if I know eventually down the road they will. Somewhere in that session, they will let go of other items so I know we will end up with space to work with. I just give it time and gently ask questions that are appropriate – for the personality type and situation.

If you’re stuck in the letting go process, here’s 25+ questions to ask yourself!


Will I have more space to do the things I want?

Does this item help me achieve my goals in life?

Would it impact my daily life not owning this item?

Is this really worth the space it’s taking in my home?

Does this drain my energy? Make me feel depressed or overwhelmed?

Did I bring this into my home?

Am I keeping this out of guilt?

Is it hard to replace if I need it again?

Have I been hanging onto this “just in case” I do need it?

Would someone who has much less appreciate this more?

If I keep this, will I remember I have it and not purchase another one?

Am I saving this for someone else? Would they really want it? Have I asked them if they want it?

Am I really going to make the effort to give it to this person?

What is the worst thing that would happen if I let go of this item right now?

If I could buy this again right now, would I?

What could I focus on if I didn’t have this? Or didn’t have all of this clutter?

What have I not been able to accomplish because I have been holding onto this?

Is this trying to fill a need? A void?

What’s more important – this item or my space?

When was the last time I used this? Wore this? Needed this? Looked for it?

Am I keeping this because this is MY memory? Or someone else’s memory?

And here’s a few really simple questions…

Do I like it? Love it? Need it?

Do I have a duplicate of this?

Is it in good enough condition to actually use?

If this item is broken or needs mending, will I actually take the time to repair it?

As you declutter I hope these questions will help you if you’re stuck or need help making decisions. Here’s a new video from our YouTube Channel with me touching on these questions as well!…


Back soon with more guys!



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  1. jennibell says:

    Great post – thank you!

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