25+ Questions to Help You Declutter

So, how was your most recent “Spring Cleaning” efforts?  Were you successful, or did you trudge back in after hours in the hot garage or storage unit, feeling frustrated because you didn’t purge as much as you’d hoped?

Or maybe you felt sick with doubts because you followed some organizing guru’s plan exactly, but it still didn’t feel right?  Somehow their limited criteria or question(s) didn’t seem to fit well with your stuff and situation.

If you’ve had success with someone’s decluttering program, then wonderful!  Their plan was for you.  But if a single emotion-focused question is leaving you numb or confused, and you feel the need for more than one question or way to evaluate your possessions, then you’ve come to the right place!

As a military spouse who moved across country with every new set of orders, I know the stress of trying to weed out the junk.  Consequently, I’ve collected books and magazine articles about organizing and decluttering in my own search for the right questions and criteria to help me decide what to keep or pitch.

There’s a lot of great questions out there.  I’ve even created a few.  Unfortunately, they’ve never been all in one convenient place …until now!  It’s taken several years to collect and organize these questions, but it’s worth the effort to get them together.

They have helped me, so I trust they’ll help you, too!  I suggest you bookmark this page or share it on your social media “wall” or “dashboard” to save it for quick and easy reference any time you need to declutter.  You don’t even have to read it all right now!  (Unless you just want to.)  Feel free to skim through it now, save/share it for later use, and then come back when you need the details for any or all categories.

Just do me a favor, please?  Let me know how this helps you by leaving a comment.  Thanks!

You don’t have to ask all these questions every time.  Some will prove useful in a sequence, helping narrow down all the factors—like a decision tree.  But they’re not listed in any special order beyond being grouped in the general categories of practical, sentimental, and might-need-someday/future-focused (including collections).  Tips regarding paper and emails are scattered throughout.

Practical Considerations

  1. Have you used it in the last 12 months? This is a popular question, but it’s not always appropriate.  Perhaps my version is better:  Did you use it during the last appropriate season/situation?  The nomadic nature of military life taught me this modification.  Sometimes you’re in a situation for a brief time where you can’t use something but could be right back in a place where you would/could use it, and it’s not worth the cost of tossing it only to have to replace it so soon.  Marie Kondo has two great questions regarding seasonal items, particularly clothes: Do you want to see this again next season? Would you be willing to wear this right now if the weather changed suddenly?[1]
  2. Is something less desirable keeping you from using it? Sometimes we have a very nice item that never gets used because we use something else that’s functional but less nice.  A variety of things fit into this category, but china dishes are an easy example.  There’s still plenty of homes with china cabinets displaying beautiful dishes that never gets used while the family eats off ugly plates.  Get the idea?  This is the question to ask when your answer to question #1 sends you into a panic over the idea of discarding something just because it’s not used.  Perhaps you’ve not used what you really treasure because you’ve been using a less desirable version.  If this is the case, then pitch the unfavored version and start using and enjoying what you do like.
  3. Is it broken? Worn out?  Ill-fitting?  Out-dated?  If so, is it cheaper (both in time, money, and/or stress) to just replace it than to fix/update it?  While some things may be worth repairing, most stuff is not.  This depends on your skills and other resources.  An easy fix for one person is a nightmare for another.  If a highly treasured item is broken or otherwise unusable, consider breaking it down even further into pieces that can be reassembled into a creative, decoration or re-purposed into something functional.
  4. Could you rent a rarely used item[2] for equal to or less than what it’s costing you to keep/maintain it? Could you borrow it from a friend/neighbor without too much awkwardness?  This question is best for items that you can afford to wait on using or at least schedule ahead for their use.  It’s a great question if you’re truly interested in getting to know your neighbors and need a good “excuse.”  Be prepared to help your friend/neighbor maintain it.
  5. Is it worth the cost of ownership (maintenance, storage, etc.) in both time and money? This question isn’t just for the stuff in a storage unit.  Think of the things in your home that require any extra special care to clean.  What about the stuff clogging up your cabinets and closets that cost you extra effort to get anything in or out of those places?  Someone wisely said that after a while, the stuff you own starts owning you [making you a slave to its upkeep]!  A closely related question that might bring this point home:  Are you willing to pay professional movers to pack and move this stuff to a new home?  All that excess weight will cost dearly!
  6. Is it still appropriate for your current life season, or has it outlived its usefulness? Menopausal women should not hold on to baby supplies.  That’s an extreme example I trust will sufficiently illustrate this question’s focus.  See Kondo for more insight on the purpose of things.  I don’t agree with her eastern mystic perspective of releasing something so it can basically be reincarnated into something more useful and come back to you, but she does do an excellent job of making us aware that some things, like greeting cards, actually have a very short-lived purpose/life-span and should not be kept forever.[3]
  7. Will it go bad/rot before you use it again? Speaking from experience, things beyond food do decay and crumble when left unused for long periods.  Then it’s doubly sad, for neither you or someone else got a chance to be blessed by it!  Some good examples from the many vulnerable items are rubber bands, elastic bands in clothes, as well as some foams and rubbers in shoes.  And sometimes the ruining agent is an external force you cannot always prevent (moths, rust, mold, etc.).

“Do not lay up for yourselves treasures on earth, where moth and rust destroy…”—Matthew 6:19 NKJV

  1. Do you really need that many of the same/similar item? How many of your duplicated items do you realistically need/use?  Surprise!  The correct answer is NOT always one!  Now, if you happen to live in very small quarters where everything is basically within reaching distance no matter where you are, AND if you always are able to wash your dirty dishes as soon as you finish using them so they are available for the next meal, then you may be able to get by with having only one of each item.  But in my house, it’s a good thing to have 2 pairs of kitchen scissors and more than one fry pan!  And of course, any home with 2 or more people where one person has a food allergy or contagion, etc., then duplicates are critical.  The emphasis here is on “really” and “realistically.”
  2. If you keep this, will you have a good (ergonomic, logical, uncrowded) place for it? Organizing guru, Peter Walsh warns that if you disrespect the limits of your space by putting too much stuff into it, “your relationship with that space will sour.”[4]  You’ll hate the extra work required to pull anything out or put it back. The goal here is to help you actually use it and not lose it in your own home.
  3. Is it the most useful? The most beautiful/most loved?  Better yet, is it both?  Make William Morris’s goal your goal:  to surround yourself with only the most beautiful and only the most useful.  The criteria of “most useful” means getting rid of anything that has only a single use/function—especially if it’s a rare use—when there’s something else that can do that job and do other jobs you need done.  Before you run out to buy a multi-functioning piece of equipment, make sure that you will actually use the majority of those other capabilities.  Sometimes a simple, single-purpose tool is better than a cumbersome multi-parts gadget.  Regarding usefulness, you may also benefit from asking these 2 questions: “Does this make my life easier?  Is it getting me any closer to a specific goal?”[5]  This last question reminds me of Matthew 19:12; sometimes we must let go of even good things for the sake of something greater.

The Sentimental Struggle

  1. Does this item register any positive emotion when you look at it or hold it? Is that emotion strong enough to warrant keeping it?  This is my spin on Marie Kondo’s question, “Does it spark joy?”  While I’m skeptical of her position on joy as the ultimate criteria, I do agree that holding things in your hand can be helpful[6]—and no eastern mysticism aspect is necessary.  You may simply decide you don’t like the way the item feels in your hand or on your skin.  So, don’t just stare at that item; exert the effort to drag it out and handle it!  And remember:  joy is deep and rich, NOT a fleeting smile or a shallow positive feeling.  Make sure the feeling is strong and positive.
  2. Can you remember its history (who gave it to you, what it’s for, etc.)? If you can’t remember now, your chances of remembering in the future are slim to none.  May as well get rid of it.  Similarly, if you can’t remember the names of who is in the picture, and there’s no one you can conveniently ask who would know, then you may as well let it go.
  3. Is it the ONLY memento you own to help you remember a person/special event? If not, which memento(s) would be the best to keep?  Which one sparks the most memories?  I believe I got this first question from Peter Walsh on a Clean Sweep  If you have more than one memento for a person/event, keep the one that helps you a) remember the most and/or b) recall the unique memory that you don’t remember until you look at this item.
  4. Could a picture or a small part of it be sufficient enough? This is a good question for 3-D items that are just being kept for memories’ sake, especially large and/or bulky stuff. The goal here is to minimize the bulk while “retaining just enough to allow nostalgia.”[7] I know from personal experience that a picture works well.  A similar question is great for some[8] paperwork we feel obliged to keep:  Could you scan it and save it virtually?
  5. Do you really need this item to help you remember? If so, is it a memory worth remembering?!  Some memories are so strong, you don’t need help remembering.  Conversely, not being able to remember something without help may be the brain’s way of saying, “It’s not worth it!”  I gave up a piece of jewelry once because it reminded me of a bad time in my life.  Whatever monetary value it had wasn’t worth reviving hurt feelings!
  6. Are you holding onto this because every time you think about relinquishing it, you remember how much money you paid for it? “Realize that at this point, the item is not earning you anything.”  “Simply acknowledge that the item provided the value it was supposed to and move forward.”  It helps to remember we often spend a lot of money on things we know won’t last forever (concerts, fancy meals, vacations, etc.).[9]  Just because this item continues to exist doesn’t mean you must retain it.  Another helpful tip here is to divide up that cost by the number of years you’ve owned it/times you’ve used it; thinking of that lower price per year/use can help you feel like you’ve gotten your money’s worth out of it,[10] making it easier to let it go.  Hinnant says visualizing someone else benefiting from it helps minimize this type of sticker shock.[11]  Also, ask question #2; it may help if this topic is a challenge.
  7. Are you holding onto this out of an over-worked sense of obligation? What are the chances that the original owner/giver will notice or care that you no longer have it?  In general, the chances are slim.
  8. Are you holding onto/collecting full sets of something just because they are a set? Be aware that companies sometimes create series of individually sold items just to sell more.  They’re counting on you vulnerably believing you need every piece they say belongs together.  If you truly love every piece in the collection, then fine; use another question to help you pare down.  But if you’re not all that enamored with some of the pieces, don’t feel obligated to buy or keep them!  Be discerningly eclectic in your collecting.  Better a cherished few on display than a full set in storage.  Remember:  only the most useful and/or beautiful/loved.

Foreseeing the Future

  1. What are the realistic chances that you “might need this someday”? “Can I picture a specific situation where I would want this again?  Am I sure I would want this particular item?”[12]  Or are the chances better that someone else could use it right now, and you could be a blessing to them?  Just beware of passing off trash; see #24 below.  When “this” is some kind of paper (mail, magazine, book, or other types of paperwork), take this question to a more specific level by asking, “Will I ever re-read or need to refer to this again?” or “Is there a legal reason to keep this?”[13]  If the answer is yes, then keep it (see Givens); if not, pitch it.
  2. Could you replace it easily/cheaply IF you really did need it “someday”? This is another fairly common question.  The logic here is that if you can replace it for a few bucks, then it’s not worth whatever it’s costing you to store it (and that’s not limited to storage unit rental fees).  I add this extension to the question:  Can you trust God to provide it again?  For papers and emails, an appropriate version of this replacement question: Will I find this info easier/quicker in my own files than I would on the internet?[14]
  3. Is this item worth saying “no” to other things? In other words, finish this sentence:  I’d rather have this than _____________ (fill in the blank).  This question or statement of comparison only needs 2 items for consideration yet works very well with large collections of similar items that need to be reduced.  In fact, you could even use this with a single item by comparing it to the minimum amount you could sell it for or something intangible (more space or freedom from obligatory maintenance).

“When you can’t decide whether to keep something, ask yourself, ‘Which is more important, the … item or the space?’ ”—Jeannie Triezenberg[15]

  1. Are you holding onto/collecting something because you think it might, someday, possibly be valuable? Keep what you truly love/can really use.  Many things being collected are never going to be worth more than their cost to you in time, money, and space.  And most of us don’t really have the extra money needed to keep something pristine just for its investment when it does have value.
  2. Are you holding onto something because you think your children will want to inherit it someday? The chances are extremely thin that a future generation will really want your treasures.  Better to ask them if they’re seriously interested in it and then give it to them as soon as you are ready to part with it.[16]
  3. If you didn’t already have this item, would you buy it today?[17] This is a great question for clothes and décor, since these items can be very trend oriented.  If you wouldn’t buy it today, then you should feel free to let it go.  Would you buy it at a thrift store in its current condition?[18]  This question is not only valuable for determining if you should get rid of something, it’s also the best question to determine how to dispose that item you’ve decided to toss!  If you wouldn’t deem it worthy of resale, then don’t donate it—just throw it away!  The only exception to this rule requires this question:  Could a creative person find ways to re-purpose it or a tinkerer use it for spare parts?  If so, then it’s possible it’s worth donating; just be aware that the thrift store workers may not see its potential like you do.  You may have to do a bit of research to find the right person or place to make your donation worthwhile.  But if trying to find the right new home for it becomes too much work and allows your junk to stick around too long, you should just throw it out.  The goal here is to free yourself from that thing, not create more work for yourself!
  4. If you part with this item, what are the realistic consequences of not having it anymore? This question can have either a negative or a positive spin.  The negative version is usually: What’s the worse thing that could happen?[19]  If a realistic answer can be lived with, then let the item go.  The positive version involves contemplating all the good things that will result from releasing something, like getting back some more space, time (spent searching or maintaining), money (storage/maintenance costs, by selling it or a tax-deductible donation), and “satisfaction” (of helping others by giving it away).[20]

“When there is more room for new stuff, there is more room for the future in your life.”—Simplify Your Life, pg. 1

Thanks for reading!


Scripture taken from the New King James Version®. Copyright © 1982 by Thomas Nelson. Used by permission. All rights reserved.

[1] Marie Kondo, The Life-Changing Magic of Tidying Up, transl. Cathy Hirano (Berkeley: Ten Speed Press, 2014), 68, my paraphrase.

[2] Paula Jhung, “The Smart Woman’s Organizing Secrets,” Family Circle (1FEB2001), 120 (120-122) suggests renting v. owning.

[3] Kondo, 60-61 re: purpose, 192-3 re: reincarnation, 104 re: cards.

[4] Peter Walsh, quoted in Andrea Downing Peck, “Get Organized!” Military Spouse (September 2010), 52.

[5] Stephanie Denton, “Secrets of Super Organizers” Family Circle (15FEB2000), 118 (116-18).

[6] Kondo, 38-42, 64-5 re: joy, 41 re: handling each item.

[7] Denton, 118.

[8] Alexis Givens, “You’ve Got (Too Much) Mail” Real Simple (March 2005), 138 (133-142); not everything should be scanned.  Certain originals must be kept.

[9] Denton, 116, both quotes and paraphrased thought.  Also see Kondo, 59-61.

[10] This is a modification of a price-tag perspective tip shared on TLC’s What Not to Wear.

[11] Amanda Hinnant, “Act Like You’re Moving…,” Real Simple (May 2004), 184 (183-188).

[12] Denton, 118.  Also see Kondo, 68.

[13] Nina Willdorf, “Save It, Pal!” Real Simple (Feb. 2005), 40 (35-40).  Has other good, more specific questions regarding paperwork and emails.

[14] Inspired by Willdorf, 40.

[15] Amanda Hinnant, “Pantry Problems, Solved,” Real Simple (April 2005), 180.

[16] “The Best Methods for De-cluttering,” Simplify Your Life promotional reprint, (Danbury, CT), 2.

[17]  Hinnant, “Act Like Your Moving…”, photo caption, 188.

[18] My version of advice from Pam Young, The House Fairy, found in “The Good Fairy of Clean,” by Carolyn Campbell, in American Way (June 2014), “Tip Sheet” sidebar, 61 (58-61).

[19] Denton, 118.

[20] Julie Morgenstern, Organizing from the Inside Out (New York: Henry Holt and Co., LLC, 1998), 62-3.

One thought on “25+ Questions to Help You Declutter

Leave a Reply

Please log in using one of these methods to post your comment:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s