Ask Unclutterer: How do you move past a fear of regret when purging clutter?

Reader Oh My (I’m thinking that’s not a real name) submitted the following to Ask Unclutterer:

I believe that the biggest obstacle to decluttering my life is the fear of regret. I have so much junk that I’m afraid to get rid of because I think it will be useful or valuable, and I am sure that once it’s gone I will immediately think of a use for it, or — in the case of collectible items that can be resold — discover I could have gotten more money out of it if I’d sold it someplace else. (As I’m between jobs right now, any loss of potential income really bothers me.)

My question is, how do I deal with regret? Most people seem able to accept that what’s done is done and move on with their lives, but mistakes I’ve made in the past haunt me for years and I don’t know how to get over them. Do you have any advice?

The best advice I’ve been given about regret is to ask myself the following questions before getting rid of an item:

  • What is the worst that can happen?
  • How would I behave if I were not afraid?
  • Would I buy it again if my home burned down?

The first question allows you to play through every possible horrible scenario. Nine times out of 10, the worst that can happen isn’t actually horrible. A common response is that you might have to borrow a similar item from a friend, which is a little inconvenient but not horrible. Obviously, if your life might be at risk if you got rid of something (like heart medication or a cane that helps you walk), don’t get rid of that item.

The second question gets you thinking about how you will respond to even the horrible scenarios. You can figure out how you would deal with these events if you weren’t afraid of regret or making a mistake. Once you know how Fearless You would behave, Fearful You can feel comfortable behaving in the same way.

The third question keeps your perspective in check. If you wouldn’t pay money for the item now, you likely wouldn’t regret getting rid of something. However, if you would spend money to repurchase the handmade quilt your grandmother made you, it’s probably best not to get rid of that quilt. I’d certainly pay money to repurchase my laptop, so it’s not something I would purge. However, I wouldn’t buy an empty yogurt tub if it didn’t have yogurt in it, so into the recycling bin that yogurt tub will go when I’m finished eating the yogurt in it.

Once you know the answers to these questions, you can feel comfortable getting rid of an item if that is the right course of action for that item.

A good rule of thumb is to take care of the things that matter to you (the possessions that you’re using and/or that you treasure, like that handmade quilt) and to get rid of the things that don’t matter to you. Owning things require space for storage, as well as money and time to maintain and manage those items. The fewer things you own, the fewer things you have to clean and store and keep track of and worry about protecting.

If these three questions aren’t helpful for you and fear continues to paralyze you from taking action, I recommend talking with a licensed medical professional about your anxiety. Getting rid of clutter should feel liberating, not debilitating, and a psychologist can help you if there is more going on than just dealing with your stuff.

Thank you, Oh My, for submitting your question for our Ask Unclutterer column. Be sure to check the comments for even more advice from our readers.

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41 Comments for “Ask Unclutterer: How do you move past a fear of regret when purging clutter?”

  1. Profile photo of

    posted by rutheverhart on

    To me, regret is the same thing as being unable to forgive oneself. Sometimes we just have to say it out loud: I blew it (elaborate how if that helps) and I forgive myself. We don’t have to be perfect in anything, including uncluttering.

  2. posted by Leiah on

    Remember when you were a kid and had all your kid clothes, school supplies, and toys? Do you have any of that stuff anymore? Probably not, because after you grew out of the clothes and got too old to play with the toys, your parents helped you give them away. Thinking of your cluttery possessions as being from another time –a time when you were younger, or a different stage in your life– sometimes helps you let go and move on to where you are in your life right NOW, instead of holding on to the past.

  3. posted by nj progressive on

    I’ve worked in museums and libraries for most of my adult life, places that collect things. It was a natural affinity for me: my parents always had lots of stuff, and I was a packrat, saving bits and pieces of my life. Now I’m paring down.

    The really wonderful stuff, like the beautiful afghan my grandmother made, I keep for both sentiment and utility. But I’m also taking photographs of it (and putting them on a flash drive that will live in my safe deposit box at the bank), so that if the worst happens, and the house burns down, I’ll still be able to appreciate her skill and love.

    As a museum person, I understand the power of tangible objects. I love holding the real thing in my hands. But I’m taking photos of things, keeping them in a special album on my laptop, and getting rid of the things that aren’t a part of my day-to-day life. I just don’t have the space or the psychic energy to keep them all. I was afraid of the regret, too, but I’ve somehow managed to get past that now, and am ready to move on.

    The hardest decisions are the family objects. I don’t have kids, so what happens to those things (furniture, art work, decorative objects, jewelry, fine china and silver flatware) that I’ve grown up appreciating and enjoying. I’ve decided to give a few things (mostly original art work) to museums and historical societies, and most of the rest will be sold.

    The next hardest decisions are which projects to abandon — sewing, knitting, art projects, because I don’t believe I’ll ever be able to do them all. I’m a process person, not a product person, so I’ve always had more ideas that I could ever act upon. But I’m finding that the more decisions I make the easier it gets.

    The easiest things to eliminate from my life: objects that remind me of problems and conflicts (books related to a career shift that didn’t work out, items from a great aunt who was always critical of me). Why keep something that reawakens pain and regret?

    The important thing is to start lightening your load, wherever you can, to whatever extent your heart will allow. Letting go is part of living.

  4. posted by Anne on

    My advice would be to do a “test run” where you choose two or three objects that you think you probably would be OK throwing away but aren’t 100% sure. Throw or give these objects away and then wait a month or two. Then think back to the objects and think about whether it bothers you that they are gone and can’t be recovered. I would bet you wouldn’t care, and that you’d feel more confident about throwing things away in the future. And if you *do* regret throwing the stuff away, at least the damage is limited to a couple of items. Another tip is to take photos of things before you throw them out. Often simply being able to see what the object was like is enough. And another good tip is to reduce collections to one “representative” item. I had a collection of dolls when I was a girl and just kept my favorite. The same goes for my childhood books. I don’t mind giving the others away so much if I keep one to remind me in the future.

  5. posted by Re on

    For things you think may be collectible or valuable check e-bay. Most of my “collectibles” are not worth enough for me to even to bother to try to sell them. This should help put your mind to ease when getting rid of some items.
    Also, I think of decluttering as a muscle you can exercise. The more you declutter the stronger the muscle gets and the easier it gets. You can start out small and keep working at it.

  6. posted by Jenny on

    Ask yourself if you would rather live with the potential for regret at giving an item away, or the certainty of living a life full of clutter, and all the negatives that go along with that.

    This is probably best used in conjunction with Erin’s first question. If the worst that could happen is still better than a life weighed down with clutter, get rid of it.

  7. posted by Will on

    I know this is probably anathema to the true unclutterers, but I go with a two-step method. If I can’t make my mind up to toss something I put it in the back bedroom for a month or two. If I don’t end up using/needing/wanting the thing by then, I know I can toss it without worry.
    If I end up taking it out of quarantine, it’ll stay for a while.

  8. posted by Heather on

    I keep a donate box and add these “I don’t know” items to it. If I don’t retrieve it again before our monthly trip to Goodwill I must not need it.

  9. posted by Susie Fire on

    I’m so glad you posted this! I find myself getting bogged down with regret because I spent so much money on all the clutter.
    My exercise to get me going on de-cluttering is one of gratitude. When I find that I’m getting down on myself for having SO MUCH stuff, I take a deep breath and say “I am grateful to have the resources to have this, and I am grateful to have the resources to give it to someone else who will use it!” That helps keep my energy going in a positive direction :-)

  10. posted by A.L. Noble on

    Will, I saw the 30-day-delay-then-give-it-away idea somewhere else a couple years back, and it was useful! I don’t know that the idea needs more validation than that. It *proves* to the doubting part of the mind that “See, I didn’t even think of this thing for a whole month – so I really don’t need it.” Quarantine can be very helpful!

  11. posted by Rebecca R. on

    If you are out of work right now, look at the extra clutter as income–even if it brings in just a little money. When my husband was out of work, he was so depressed he didn’t go through all the stuff he had (like toys and comic books) that could have been purged and sold on ebay or other places. Now our entire dining room table is covered in boxes and boxes of comic books, that are worth money, but now that he has a job, he says he doesn’t have time to deal with them–even though he says he wants to get rid of them. I would advise to use this time off wisely, since when you get a job again, you might not feel like decluttering.

  12. posted by shona~LALA dex press on

    I use the 6-month box method + that frees me from any regret, which seems to be what a lot of people are mentioning above, although the duration varies.

    I like the rule that if you would buy it again you probably should not get rid of it. I just went through this very process with my car that was almost totaled by my ins. co. after a recent accident. We contemplated becoming a single car family if the decision went in that direction. In the end I could not fathom being without a car + started imagining what my next car could be.

    It also helps not to have sentimental attachments to objects, which happens to be my case.

  13. posted by Jodi on

    I find it helpful to give those items to someone I know will need them. Single moms and low income families often NEED the useful things. When you are able to bless someone with those “I might regret this” items you no longer look back with regret, but with gratitude in knowing you helped someone else.

    And its hard to regret giving something away when every memory of your clutter is remembered along with the grateful tears of some of the people you have blessed.

  14. posted by Marie on

    I understand. I have collectables and vintage items I’ve gotten from flea markets and yard sales. I decorate my home with them, but in the past 3 years I’ve collected too much! I know I should resell them for $$$, but what if I sell them too low? I try to remember that I’ve gotten great deals before, so if I sell an item too low, it’s just someone else getting a great deal. I can live with that.

  15. posted by Cindi on

    There has been a lot of very good advice in the article and the comments!

    I’ve seen my mother struggle with the fact that the collections that seem valuable to her are, in fact, worth very little to antique dealers etc. She has been completely frustrated by knowing that she can’t store them any longer but can’t get the $ that she feels they’re worth.

    For myself, getting rid of (most) things has been answered by two other questions in addition to whether I will truly use it anytime soon. 1) does this cost me more (in storage fees or anxiety as a result of the clutter) to store than they would to replace, and 2) if I actually needed to use it, would I be able to find it or have to go out and buy a new one anyways?

  16. Profile photo of

    posted by ninakk on

    I have participated in the Apartment Therapy home cure a few times and have always liked the Outbox concept. If you are uncertain about some object, place it in the Outbox (bag, basket, whatever) and give it a bit of time. If you still feel you don’t want to get rid of it, take it back and also give a proper home for it. On the other hand, if you don’t desire it once your time is up (two weeks is usually long enough to create some distance if distance is to be created, but longer is fine too), let go of it. It is very rare that I take something back, but I like the Outbox since it gives me a proper detachment time. Stuff I’ve donated, I’ve never had regrets about.

  17. posted by Leslie on

    As a child, I can remember being very attached to my stuff. Until I spent a couple days in the hospital-they had dismal children’s toys. The following weekend my dad and I packed up all those children’s toys I couldn’t bear to part with and we made a large toy donation to the children’s playroom.

    As a child, it was a no brainer. Someone else needed these things more than I did. Today, I strive very hard to keep that same attitude when it comes to my stuff. As an adult, it is much harder as I also weigh the cost involved in addition to use and emotional attachment.

  18. posted by infmom on

    My parents were narcissists and anything that didn’t matter to them could not possibly matter to anybody. They were great ones for throwing out and destroying other people’s stuff without blinking an eye. I think this is the main reason I cling to more things than I should.

    My husband, though… I think he’s a borderline hoarder. His father was the same way. You can’t “waste food” and you can’t get rid of anything that “might come in handy someday.” Everything that can be recyled must be recycled, even if it means it sits around here for ages waiting to be cleaned up enough to recycle.

    Case in point: Since our daughter moved to her own place nearly five years ago, we have had several sets of single-bed-sized sheets in the linen cupboard. We do not have a bed that size in the house. Every time I say we’re going to give those sheets to a thrift store, he comes up with some reason we have to hang on to them. The latest was “I can take them to my next first aid class to be torn up for bandages.” Of course, he’s not going to be taking any more first aid classes any time soon.

    So, this weekend, I will take all those sheets out of the cupboard, save one or two to make a new back for a quilt that needs it (and do that this week because the quilt has to go back to our daughter) and the rest get stuffed in the DONATE bag to go to Out of the Closet next weekend. Done.

  19. posted by Sinea Pies on

    Parting with our stuff can be such an emotional ordeal. I totally identify with the dilemma. Except, perhaps, for family photos I’ve recognized that everything else is negotiable. Which do I want more? A clutter free home or the “security” of my stuff. I now love clutter-free more!

  20. Profile photo of

    posted by chacha1 on

    I have not regretted a single thing I have uncluttered. Being thoughtful about it, and taking whatever amount of time is necessary, have been the keys. The 30-day rule is constantly in play. And as others have said, the more OUT decisions I make, the less difficult each succeeding decision becomes.

    p.s. if income is a consideration, counseling for anxiety may seem out of reach, but most communities have *some* resources.

  21. posted by *pol on

    It’s a tough one. I think my strength to let go of potentially useful or valuable things for me right now comes from a position of stability. I am in secure place in my life right now (not trying to tempt fate by mentioning it, but it’s true). When my life was in stages of uncertainty or want, it was IMPOSSIBLE for me to give up anything that could be useful. But now that there is FAITH that my life will continue to provide for what I need, it is easy to pass things onto others that may need it more than me (even valuable things).

    At this point in my life I need the space and freedom more than the objects and clutter.

    “Oh My”… until things stabilize it may be difficult to declutter.

  22. posted by Dee on

    When I get stuck on an item I ask myself these kinds of questions and others and if I’m still uncertain I put the item aside. Occassionally I will change my mind, but most of time I haven’t missed or needed the item so I let it go. I’ve found that I bought things or held onto things for someday or the life I might have. Holding on to these things keeps me from having the the space (both in my home and in my head) for the things that should be in the life I have now and want to have. I find knowing I’m creating opportunity to receive by letting things go makes it so much easier to declutter.

  23. posted by The Simply Inspired Home on

    I find i need to be in a good zone when I purge. Too crazy and I have regrets. I find phases are good. Purge some stuff, then wait a while and if I don’t use something for a year or under 6 months then It needs to find a new hone.

    Happy purging my friend.

  24. posted by MessyMom on

    I agree with *pol that part of the reason you may be having trouble purging is due to the instability in your life right now. I have always had a Type A personality and been stressed easily. I never thought I would go to therapy, but about a year and a half ago I did attend a few sessions of stress therapy because I realized I needed to change. It really helped me, mainly because an objective person was pointing out some of the bad patterns I had fallen into and giving me concrete strategies for how to break those patterns. And once I became aware of those things, it suddenly became much easier to purge. We weren’t living like hoarders or anything, but I am amazed at how much stuff I’ve gotten rid of. I have donated many bags of items and filled my trash and recycle bins multiple times. The items that I’ve researched and believe are worth the trouble of selling are getting organized in my spare room for a yard sale.

    I still have some work to do, but I feel so much more at ease in my house. And I don’t spend a lot of money so I never would have considered myself a shopaholic or anything to that extent, but I’ve been surprised at how many times I’ve caught myself about to make an impulse purchase. Now I stop and ask myself, is this really worth having to deal with later?

    I’m not necessarily saying that you should seek therapy, just that if you can be more conscious of both your actions and the motivations behind those actions, it could really make a difference in your decluttering efforts and your life in general.

    I also sometimes turn on Hoarders or Clean House while I’m decluttering because 1) both shows make me feel better about my housekeeping and 2) they serve as cautionary tales. If it seems like I’m keeping too much, I just picture myself on national TV trying to explain why I’ve felt the need to hang onto those items for so long, and suddenly getting rid of stuff seems like the better decision. :)

  25. posted by Miriam on

    Thanks so much for all the ideas and suggestions, everyone – very helpful!

  26. posted by K on

    Great and thorough answer to this question, Erin.

  27. posted by Maya on

    I definitely agree with the people who have recommended some form of time-out/box up strategy. Whenever I have an item that I can’t look at and immediately decide to toss, setting it aside for a few months to see if I think of it/need it/use it is helpful. I can’t think of anything that I’ve gotten rid of that I’ve actually regretted.

    The other thing about regret is that the issue might not really be the item itself. If the item is a symbol of something that you wish had gone differently or that you wish you could relive, than a change in mentality helps enormously. Think about the good that came out of that decision/item and enjoy it. And when worrying about if you could have sold it for more, realize that is a “grass is greener” attitude that will never bring you happiness. By selling it you made some money from it, and that is a good thing.

  28. posted by Debora on

    The one thing that helped me get over the fear of throwing things away was something I read in a book: did you ever regret throwing something away? Probably so. Does it still keep you up at night? Probably not.

    A time out box would never work for me. I know that if I keep the stuff I intend to through away even for one extra day, I’ll find a reason to keep it. Everything goes out of the house the same day.

  29. posted by Allison on

    Something to remember regarding concern over getting enough money out of the item is that sitting in your home, it’s getting you $0. So the difference between selling it to A vs. B is probably much smaller than the difference between selling it to A and not selling it at all. And in the end, selling it now and having $x today is possibly worth more than selling it later and having to store and care for it in the meantime, even if you get $x+y later. I find that once I get rid of an item I really don’t want any more, any concern over its perceived monetary value quickly dissipates as I completely forgot about the item once it is no longer interfering with my life by taking up space.

  30. posted by kath on

    I go through that myself every time, and then I remind myself that once I get rid of something, I usually don’t even think about it again and just let it go. The only things I sweat over anymore are the family heirlooms. What I have decided to do about that is to see if any other family members want the item for themselves or their children, and if not, then I can get rid of it without thinking twice about it. It drives me crazy to see people get rid of things that another family member would love to have, so I try to be sensitive to that. Please do not donate grandma’s wedding gown to Goodwill until you know that nobody wants it! The same goes for jewelry and furniture. Again, if no one claims those things within a reasonable amount of time, then sell/donate them with a clear conscience.

  31. posted by K00kyKelly on

    I don’t think this question is really about uncluttering at it’s core. You’re putting a lot of pressure on yourself to optimize everything. To get that every last bit out of things – be that money, usefulness, or some other kind of value. Consider that maybe you’d be better off optimizing your time and energy spent. There is a big focus on doing things perfectly in our society. Perfection takes a LONG time. I frequently remind myself of the 80-20 rule. You get 80% of the way there with 20% of the effort. For selling things 80% of the money for 20% of the time listing it. The otherside of it is that is that last 20% takes 80% of the time… is it worth it? Also, if I spend too much energy optimizing I get no result at all because I get overwhelmed and stop. Getting the absolute most out of everything isn’t always possible or desirable.

  32. posted by Alex on

    Four years ago I got married, rented out my house to tenants, and stored almost everything o owned in the basement. I moved into my husband’s house 4000 miles. away. We came back to visit this summer and the renters who had seemed so nice four years ago had trashed the house including all my prized possessions. Everything in the basement was covered with cat pee and I spent days sorting through things. Most of it was now trash. My only regret was that instead of selling or donating it years ago and making any money, I now had to spend money on a dumpster and waste my time and my family’s time. I now have a one and three year old too. I wish I had dealt with this junk years ago and that I could spend my time enjoying this lakefront home with my family. The only thing there is to regret is lost time. Get your junk our and move on to better in the future.

  33. posted by Vanessa H. on

    Sometimes you need an extra step to take away the fear.

    I put my things in clutter limbo before donating them. Limbo can be the trunk of my car or a shopping bag in the closet. I give myself time to miss the item. Usually I don’t miss it. Then when the bag is full or the trunk is getting on my nerves, I drive the item(s) to the Goodwill donation truck.

    Sometimes taking that last step is difficult but I usually make it through. (Once or twice I have still been afraid to take that final step but it’s okay if you have to make two trips to finally donate something.)

  34. Profile photo of

    posted by Rosa on

    For me it’s just been practice. I was more worried about regret I might feel than anything else – starting with the low-hanging fruit and recognizing that I didn’t regret any of it made it easier for me get rid of things that were harder decisions.

    No bad regrets yet!

  35. posted by Catherine on

    I’m planning a (welcome) move after 3 very stressful years so this topic speaks to me. I find getting rid of stuff brings up a lot of emotions and I have to take it step by step. So I’m giving myself permission to really look at and keep some things because they do help me realize how much I’ve accomplished in my time on earth. Not all things are bad — you just have to come up with a balance that works for you. I don’t want an empty, sterile house but I don’t want a stuffed house either.

  36. posted by Cat on

    I always ask myself two questions. Did I know I owned this item? Would I pay money to recover/replace this item if it was stolen?

    At that point, it either goes in the trash, or in a pile to freecycle. I find that freecycle is a wonderful way to get rid of something without feeling guilty about it, in the “it’s going to a good home” mindset.

  37. posted by robyn on

    I find it helpful to focus on the use or benefit that the new owner will get out of my items, rather than dwelling on my feelings about them. If you sell or donate something, it will be used and enjoyed NOW, by someone who really can use it, and will not be sitting in your closet deteriorating over time.

    Look for library book sales or church rummage sales so that two groups are getting benefits…the person who is buying and using your item, and the group holding the sale which gets money to fund their programs. I also agree with the above poster about Freecycle…I always read through the responses and find the person that seems most sincerely happy to get my item. I’ve received some of the nicest emails afterwards from people who are truly grateful for my stuff and it makes me really happy and it’s easier to let go of things that way.

    And a comment on the money value of selling your stuff…with the proliferation of ebay and craigslist, the glut of supply means that it’s really rare that you will ‘make’ money. If there are 100 of X collectible on ebay, then yours is not going to be worth much. I figure if I make a little money to pay for my lunch for a week or for a tank of gas, then it was worth selling. I’m not going to get rich or even recoup my original purchase, but a free tank of gas is worth more now than having something sitting in the back of my closet. Maybe you could plan to save up all the money from your sales to buy something ‘big’ that you’ve always wanted. Some incentive to keep selling things.

    On the flip side of ebay, the ease of finding random stuff can work in your favor as well. If you suddenly regret a sale, you can probably buy back the exact same thing again at a cheap price. Hardly anything, except for family heirlooms, are ‘gone forever’.

    Good luck!

  38. posted by Wanda on

    I have found feng shui to be very motivating–to make room for new, wonderful things in my life, I have to discard old things that are anchoring me in the past. I ask myself “is this what I want for my future, or something that belongs to my past?”

  39. posted by Ideealistin on

    I think the comments have said it all!
    But probably one more thing I find helpful: I have stopped expecting to NEVER regret ANYTHING. If I am not perfect in other fields why is the expectation to be perfect in every single decluttering decisions? We keep so many things for too long, why not some for (maybe) too short? Do I regret some novelty food I tried just to find out it’s not my taste, some overpriced drink I had, a movie that bored me? Maybe in that very moment but these decisions don’t haunt me years later. And the minor misdecisions in decluttering don’t haunt me either. What can happen? There’s one book you feel like reading again later that was decluttered with 100 others, there’s the waffle iron and all the other kitchen stuff you did not use for 10 years and then the next winter your waffle crave seems to kill you? Borrow the book. Or even buy it. Go out and eat a waffle. And keep in mind that you most like would not have kept that one book but all hundred and not the waffle iron but a pantry full of unused machines.

  40. posted by Kitty on

    To the comments about giving to someone who needs it, I use Yahoo Free Cycle and am able to give to someone who really needs items (child has outgrown clothes, parent out of work, looking for size 7 kids clothes, school books, art supplies, bike, etc) and it does feel different knowing it is needed by someone else.

  41. posted by loopsicle on

    I stumbled on this website last night while looking for inspiration/support for the much needed declutter of my space. The original response was great and I’m so grateful to everyone who has shared their experiences and ideas. I now feel calm and ready to take the leap into decluttering. Deep down I know it’ll be so liberating and I’ll probably be asking myself, “What was all the fuss about?!”. Here I go….

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