The Four Questions to Ask Yourself When Decluttering Mementos

There’s some parts of a home that are easy to organize. Pantries, closets, and bathrooms may be tedious and time consuming, but they are also pretty straight forward. The area we struggle the most with decluttering and organizing, however, are MEMENTOS: old schoolwork, old artwork, old photos, items that belonged to a family member who has passed, heirlooms, etc.

It’s much more challenging to toss your late grandma’s broken teacup than it is to toss the expired box of cereal in the back of the pantry, and for good reason. These items are so much more than just clutter to us. They symbolize a special time or a special person. When you get rid of these items, it feels like you’re getting rid of a those memories of that time or person as well.


Here are the four main questions I ask clients, when sorting through boxes of mementos alongside them. Of course these questions often lead to long conversations, realizations, laughter, and sometimes tears. This work isn’t always perfectly streamlined, aimed at productivity and efficiency. The process of going through memorabilia, often takes time and thought.

Are you happy knowing that you have this? Does it make you laugh and smile as soon as you see it?

When digging through old boxes of mementos, I notice pretty instantly which items are worth keeping or which are worth donating/tossing just by looking at the faces of my clients as we go through each item. There’s this look of excitement and joy: “Oh my goodness I remember this!; Look -isn’t this hilarious?; This was my favorite when I was a kid!”; “This card meant so much to me”, “This was my grandpa’s favorite piece of art”.  That instant burst of joy is contagious! There’s no shame in keeping these things that make you that happy and excited!

Anything that doesn’t give you this feeling of joy (like your notebooks from your college economics class) just isn’t worth keeping.

Can this item leave a better “legacy” in someone else’s home, rather than in a box?

Would the joy of donating this item and knowing that it will be better used by someone else, make you happier than keeping the item itself? Regardless of where you live, there are likely lots of charities and organizations that will gladly take lots of new or gently used household items. Remember that you can find my Denver-based Donation Resource Guide here.


Are you keeping this just because it was a gift, and you feel guilty donating it?

Ok. So the item doesn’t make you happy, but you feel like you need to keep it out of obligation. A distant cousin gave it to you as a gift, and you feel bad getting rid of it. They spent their hard earned money on it! Or they handmade it five years ago and it took them hours! Remember: This item is not that person. Your grandma's vase is not your grandma. Your sister’s necklace. that she gave you as a gift five years ago, is not your sister. Don’t keep something out of guilt, only keep things out of joy.

Are we respecting this specific memory or this specific person by keeping this item in a box?

If you are sure you want to keep something, ask yourself whether keeping it in a box in the basement, attic, closet, or storage unit is really the best solution.  How can we display your favorite memorabilia (that DO bring you lots of joy, and ARE NOT being kept out of guilt) so that we are honoring the time, person, or memory that this item represents?

Can you display it somewhere, frame it, or use it in your house - so that you get that joyful feeling every time you see it?

There’s so many examples of how to do this, many of which I’m sure you’ve heard of:

  • Turn old T-shirts and clothing (yours or a loved one) into a quilt .

  • Turn your old wedding dress into a blanket, knowing that every stain and fray is just symbolic of your growing, messy, meaningful life together.

  • Take photos of your kiddo’s favorite artwork and get it printed into a photo album, or frame their artwork and hang it in their room.

  • Make a shadow box, framing photos, ticket stubs, letters, and mementos.

  • Display racing medals into Christmas ornaments, so that they are displayed on the tree once a year.

Going through old mementos is challenging and it’s easy to get decision-fatigue. If your weekend plans include finally digging through those old boxes in the attic, remember to show yourself some grace. You don’t need to do it all in one day. Start with just one box. Pour yourself some strong coffee. Play some fun music  - and keep these four questions in mind as you sort.

Have you donated a memento in someone’s honor/name? Or have you transformed your mementos into something functional, so that they could be used or displayed around the house? Share in the comments below!