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.

Do you have a question relating to organizing, cleaning, home and office projects, productivity, or any problems you think the Unclutterer team could help you solve? To submit your questions to Ask Unclutterer, go to our contact page and type your question in the content field. Please list the subject of your e-mail as “Ask Unclutterer.” If you feel comfortable sharing images of the spaces that trouble you, let us know about them. The more information we have about your specific issue, the better.

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