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When it comes to decluttering, sentimental stuff is often the hardest area to handle during your downsizing journey.

Things like movie stubs, high school yearbooks, report cards, love letters, and more are difficult to let go of because of the tidal wave of feelings and memories that are attached to them.


Listen to Justin address this topic on Episode 633 of Optimal Living Daily.


At first, you might have just one small box of sentimental belongings. But when that collection starts growing and taking up more and more space in your home, it starts to feel like clutter. And when clutter abounds, it gets in the way of how much quality time you spend with yourself and your loved ones.

As you'll see in the following two stories, while sorting out sentimental items is tough because everyone has a different relationship with their own items, it’s not impossible!

Grab our checklist with steps on how to let go of your sentimental stuff.

#1: Lee’s Journey: Parting with Sentimental Stuff

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Lee Rankinen | Photo from @OLDPodcast

LEE SAYS: According to my wife, Joc Marie, I am the “least sentimental person” she has ever known!

Despite that, I somehow managed to move in and out of 7 apartments before I was able to part with the following items:

  • an old shoebox filled with photographs from summer camp and high school
  • dozens of very rarely worn t-shirts
  • a gold necklace that I hadn’t worn in 7 years

I told myself that I wasn’t keeping these items for sentimental reasons. I didn’t see a problem when they weren’t taking up too much space, and there was a possibility that I might use them again. (Because who doesn’t take a 5-year break from wearing a t-shirt only to put it right back into the rotation?)

After almost a decade, I was finally able to part with each of these items when I created a process to re-evaluate the items that I owned.

Lee’s 5-Step Process

Now that you’ve heard Lee’s story, you’re hopefully a little less intimidated to start your own decluttering project of sentimental belongings.

Here is the actual process that Lee used when it was time to say goodbye to some cherished items:

  1. Create Ground Rules. Determine what is important to you before you start decluttering and what evaluation process you are going to use to analyze each item. Don’t get rid of sentimental items “just because.” If you have an item that is sentimental but still brings value to your life, then you shouldn’t excessively worry about getting rid of it.
  2. Start Small to Gain Momentum. Start with a kitchen or bathroom where you’ll be less likely to run into sentimental items that can stagnate your process. Use the momentum you create to tackle bigger projects.
  3. Ask for Help. Lee found it immensely helpful having his wife with him and giving him support to let go of t-shirts from high school and college that reminded him of good times. The person that helps you through this process doesn’t have to be a minimalist or an emotionally detached robot — they just have to be someone whose opinion you value and is able to be honest and understanding with their feedback.
  4. Have Fun. The process of removing sentimental items that no longer add value in your life should not feel negative or overly serious. As Lee and Joc Marie were going through his shirts, he would snap pictures of some of the t-shirts to share with some school friends who he knew would enjoy seeing them. Being able to appreciate these sentimental items one last time made the decluttering process a memorable experience.
  5. Complete The Process As Soon As Possible. The faster you can complete this entire process, the more successful you will be. If you can dedicate an entire day or weekend to the decluttering process, you’ll be able to stay properly motivated to completion.

#2: Allison’s Journey and Her 4-Step Process

Allison Anderson is a vlogger who’s aiming to declutter her life and travel the globe. In her own words:

“Everybody is different — approaching your sentimental item stash in your 20s is probably very different from approaching that stash in your 70s.”

There are some things that she thinks about when decluttering sentimental items which she shares in this great video.

Allison’s process consists of four steps:

  1. Identify Why You Feel Sentimental. Most items we consider sentimental bring about powerful emotions or memories, which is why they are so difficult to let go of. That being said, you should remove items that you have negative emotions attached to. Emotional baggage is something you and your home can afford to say goodbye to.
  2. Repurpose Items. Instead of hoarding and forgetting about items stashed somewhere, try to use or display the items that mean something to you. One creative way to repurpose old clothes is to cut a small piece from each piece of clothing and sew them together into a throw or quilt. You could also sell, re-gift, or donate items to people who would gain value from them.
  3. Digitize the Item. Being able to digitally store memories is a great way to remove physical items and clutter from your life and allow you to access those memories anywhere and at any time. This works well for photos, tickets, IDs, etc. Create an online photo album of all the sentimental items that you decluttered, and you’ll be able to view those items without needing physical space to store dozens of items.
  4. Have a Guilt-Free Box. This is one special box that’s dedicated to the sentimental items you just can’t seem to part with. You shouldn’t be losing sleep or suffering from prolonged anxiety when it comes to decluttering. In this box, you can keep whatever you want without needing to justify why. When the box gets full, reevaluate. Decide if you’d like to get another guilt-free box, or organize so that there’s space in the box for new items.

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Memories Are Forever

“Some memories are unforgettable, remaining ever vivid and heartwarming!”
– Joseph B. Wirthlin

Remember that you should feel good with what you’re keeping.

Once you come to terms with the fact that the positive emotions are elicited by the memory — and not the actual item — it’s easier to move forward with the decluttering process. Letting go of the items doesn’t mean you’re erasing treasured memories or emotions.

One invigorating way to cherish a memory is to let the memory live on in action.

Let’s say there’s a gift or item from a late friend or relative that you’ve decided to keep and display. Be sure to talk about what a wonderful human being he or she was. Try to incorporate some of their qualities into your own life. By doing that, the good memories will live on for the rest of time.

Or maybe you have a box of handwritten notes and letters you exchanged with friends or romantic partners in school. Even if you decide to no longer keep those notes and letters, think about why they meant so much. Is it because you enjoyed writing and sharing experiences through the written word?

If so, you could check out organizations like The Letter Project, a movement dedicated to writing letters to girls around the world who are in need of extra love and support. You can cherish memories and make a real difference to someone else’s life — and create new, beautiful memories — all at the same time.

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