In complete honesty, one of my very favorite parts of the decluttering process is going item by item and deciding what to keep or toss. (And my next favorite part is loading all the trash and donations into bags and cardboard boxes to get them out of the house!) I genuinely LOVE getting rid of clutter because of the fresh, light, open space it creates, and I rarely struggle during the decision process. But having worked with lots of friends and family in organizing their homes, I’ve learned that I am very much the exception, not the rule. In fact, most people DO struggle with the decision-making step…so much that it’s usually the primary reason people put off decluttering in the first place. Today, I want to share the reflection questions I find most useful when figuring out what should stay and what should go. It is my hope that they help you when faced with tough decluttering decisions in your own home!

Sorting cardboard boxes with signs for Donate and Trash

The 2 Best Questions to Ask Yourself When Decluttering

One of my favorite home quotes of all time is this one:

“Have nothing in your home you know not to be beautiful or useful.”

Why? Because it cuts to the very essence of why we have the items in our homes that we do. Ideally, we should LOVE the look, feel, or function of the items in our homes AND have really practical and concrete USES for them. When either LOVE or USE-FULLNESS is missing for an item, it’s time to consider getting rid of it.

Keep or Toss Flow Chart on a blue clipboard shown with sorting signs

Want these printables? They are part of my FREE “How to Organize Any Space” Guide – Sign up at the bottom of this post!

1 – Do You Love It?

So many of us hold onto things simply because we already own them, even if we don’t particularly like them. Have any of these scenarios ever been you?

  • You reach for a shirt in your closet and think, “I really don’t like the way this fits” or “This color isn’t nearly as flattering as I first thought,” but then you put it back on the rod.
  • You glare at a piece of furniture and say “This hand-me-down couch is so ugly” or “That table just doesn’t fit the way I need it to,” yet you walk by it or pile stuff on it day after day.
  • You dig through your craft stash, find a fabric and think “I will never make anything out of this,” but then you put it back anyway.
  • Every time you open your kitchen cabinet, you reach past a perfectly good mixing bowl to one you like better.

No matter how practical or useful an item is, when we don’t love something, we are much less likely to use it, wear it, display it, etc. And if you’re never going to reach for a particular item, ask yourself: why keep it?

2 – Do You Use It?

All of us have items in our home we never or rarely touch. I bet as you sit here right now, you can think of about 5 in your kitchen gadget drawer alone.

In theory, getting rid of items you have no good use for should be fairly easy and straight forward. If you don’t use it and can’t foresee any situation in which you will use it, it’s a great contender for the donation bin.

But I’ve learned that people who really struggle with too much clutter have trouble letting go of these un-used items because of the “someday I’ll use it”-potential. Even though it’s not something you use now, you might someday. And if someday comes, you’ll be so glad to have it…right?!?

Here is where you have to weigh what’s more important to you:

  • Keeping anything and everything you might have a use for one day, even at the cost of an over-crowded, clutter-filled home.


  • Increased space, function, and order created by removing excess items.

I suggest that almost every time, the “cost” of keeping an item (in precious space, stress, and sanity) is much greater than the cost of replacing the item in the (very unlikely) event you will actually need it.

Where Love & Use Overlap

Ideally, you want to both LOVE the items in your home AND have real, concrete USES for them. In fact, any item that is a clear YES for both criteria is one you can make a solid case for keeping.

Likewise, any item that is a clear NO for both criteria (as in, you neither love NOR use it), it’s the perfect contender for the donation bin.

Keep or Toss Flow Chart on a blue clipboard

However, the decision point becomes much muddier when you EITHER love OR use an item, but not both. This is when further consideration is needed…

Great Follow-On Questions to Consider

As much as I want to provide you perfect clean-cut guidelines or some What to Toss checklists to help you make all your decisions, the reality is decluttering your extra stuff is much more art than science. Only you can truly identify if and when you are ready to let go of your belongings.

But before you talk yourself into keeping something just because you love it or just because you use it, here is another list of questions to honestly and openly consider:

Again, these questions should ONLY be considered for items that you EITHER love OR use…

Keep or Toss Flow Chart on a blue clipboard

Want these printables? They are part of my FREE “How to Organize Any Space” Guide – Sign up at the bottom of this post!

Do You Have Space to Happily Display It In Your Home?

Is the item something you proudly show off, display, and/or make space for in your home? If yes, then your answer is likely to “Keep” it.

Conversely, is the item hidden away, placed in storage, covered up, or forgotten about? If yes, then your answer is likely to “Toss” it.

Is it a Precious/Family Antique or Heirloom?

Is the item something that has value, stood the test of time, been passed down to you, or been in the family for generations? If yes, then your answer is likely to “Keep” it.

Remember – this MUST first satisfy the LOVE or USE key question! If you don’t love OR use an item, I rarely advocating keeping it “just because” it’s a family treasure.

Is It In Good Condition?

Is the item complete, in working order, and/or functional? If yes, then your answer is likely to “Keep” it.

But if the item is missing parts, it doesn’t work, is past the expiration date, or is in need of significant repair in order to make it functional, then your answer is likely to “Toss” it.

Do You Have a Good Reason to Store It For Future Use?

This situation may not apply to everyone but should still be considered: Is there any potential you will realistically use the item in the future? (This is different than keeping items for the “just in case” scenario discussed above.)

For example:

  • Do you move a lot (like we do!), and even though an item doesn’t have a use now, it might in a new home?
  • Are you doing a renovation/makeover in the near future, and certain fixtures, furniture, or large items will be used then?

In these instances, as long as you love or realistically might use the item, you can often justify keeping it.

NOTE: This justification may also apply to seasonal-items.

What Is the Emotional Toll of Getting Rid of the Item?

If Greg were to chime in on this post, he would immediately tell you that I’m about the farthest thing from a sentimentalist there is. And it’s true. When it comes to our belongings at least, there aren’t many things that I have a super emotional attachment to; and most of my decisions are based on utility rather than sentimental reasons. This character trait most certainly helps me declutter with relative ease.

However, if you are someone who does have a lot of emotion connected to the items in your home, AND you struggle with immense guilt when you finally let things go, then you may need to also weigh the emotional cost of your decisions.

If you cannot justify keeping an item for any logical reason, but you feel in your gut that you will immensely regret parting with it, my biggest piece of advice is to wait on the decision for that particular item. Over time, our feelings about items change; and although you might not be ready to get rid of it now, you might be able to down the road completely regret-free.

Does It Spark Joy?

Finally, I would be remiss not to mention the catchy phrase, “Does it spark joy?” by Marie Kondo in her book, The Life Changing Magic of Tidying Up. This phrase has the power to take all the questions I outline in this post and distill them down to a single yes/no answer. If you are unfamiliar with this decluttering concept and/or haven’t yet read my experience using this phrase to guide my decluttering, read the full post here: Does It Spark Joy? My First Konmari Experience

What To Do With Items Once You’ve Decided

I want to emphasize that when I say “keep” and “toss,” I am simply meaning that you keep the item in your home or get rid of it (not necessarily toss it in the trash.) Once you’ve decided what items to keep or toss, here are some other posts to help you decide what to do next!

Sorting signs to be used for decluttering

Want these printables? They are part of my FREE “How to Organize Any Space” Guide – Sign up at the bottom of this post!

For most people who have too much stuff, deciding whether to keep or toss items is usually the hardest part of the entire organization process. Because as much as we want to make rational decisions based on “proven” criteria, so much of what we own is tethered to us emotionally, spiritually, and even logistically. I hope what I have here helps you make tough decisions when decluttering your things so that you can ultimately create the clutter-free, spacious, peaceful home you may be craving.

See You Soon!