If I ran into my ex, would I be happy I was wearing this?

If I ran into my ex, would I be happy I was wearing this?

And other questions to ask yourself when decluttering

Gretchen Rubin, happiness guru and author of Outer Order, Inner Calm, spoke at the National Association of Productivity & Organizing Professionals (NAPO) annual conference about how getting more control of our stuff makes us feel more in control of our lives.

Of course, she was preaching to the choir...that’s why we, professional organizers, exist. We’re passionate about bringing order to our clients’ lives so they can experience the joy and peace that comes with it.

One of the many things we do to accomplish this is to help clients think critically about why they’re keeping certain items and whether it’s time to let them go. The most effective way of doing this is by asking just the right questions.

The most memorable piece of advice Gretchen shared was to ask yourself the following when cleaning out your closet:

“If I ran into my ex, would I be glad I was wearing this?”

I really can’t think of a better motivator to keep only the clothes that make you feel fabulous!

Some items are harder to let go of than others

Not every item is as easy to let go as a dress from TJ Maxx might be. For example, if an item reminds you of your past, you received it as a gift, or you think you might need it someday, you might feel emotions like guilt, shame, and sadness at the thought of getting rid of it.

But keeping these items can have a higher emotional, mental, or spatial cost than value. You might feel resentment at the person who gave you the gift. Frustration that you have to move the item every time you want to get out your vacuum cleaner. Embarrassment because it’s a simple kindergarten math worksheet that you feel you should be able to throw away.

But you don’t need an organizer

You can do this! Instead of freezing up or giving up because you just can't make a decision, take a deep breath, look at the item, and ask yourself one or more of the following questions....and be honest when you answer them.

General questions

  • Why am I decluttering in the first place?
  • What's more important, this item or my space?
  • Does this item add value to my life? How?
  • Is it helping me achieve my goals?
  • Would I buy it again right now?
  • Would it feel better to give it to someone who would use it?
  • Could I borrow it from someone else if I needed it?
  • How many do I have? Do I need all of them?
  • If this item were a person, would it be a friend, an acquaintance, or a stranger?

Practical items

  • How much would it cost to replace it? Could I afford it?
  • When is the last time I used it?
  • What is it about future me that is more likely to use it than present me?
  • If I keep it, will I remember I have it? Will I know where it is?


  • Does it reflect who I am today?
  • Do I have anything to wear it with?
  • When is the last time I wore it?
  • If I fit into it “someday,” will it still be in style? Will I want to buy new clothes instead?
  • How many of this item do I wear in a week? How many do I really need?
  • What is a reasonable number of these to have?
  • If I ran into my ex, would I be glad I was wearing this?

Sentimental items

  • Does this item bring up positive or negative feelings?
  • Are there emotions I’m avoiding feeling by hanging on to it? Would letting myself feel those feelings help me let the item go?
  • Can I keep just one of this type of item and let go of the rest?
  • If I had a picture of the item, would it bring back the same memories?

Give it a try

Are you ready to start decluttering your closet, attic, or basement? Download this list as a PDF, print it out, and stick it on the wall next to you. Be honest with your answers.

Finally, know that the goal isn't to get rid of everything...it's to get rid of stuff that's no longer serving your best interests. It's OK to keep something if it feels right and good to you.

Let me know how it goes!