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Simplifying the Sentimental


Childhood photos on a desk with a laptop while a woman simplifies the sentimental by scanning childhood photos.

I finally met my match on this minimalism journey: sentimental keepsakes. There’s a reason Marie Kondo saves this category for last. The hard part wasn’t letting go of things (which was easy) or even making the decisions of what to keep and what to release (which came quickly). The process of reliving the memories attached to every single object was psychologically exhausting. But here I stand (er, sit wrapped in a pastel rainbow afghan my mom made) on the other side victorious: 15 boxes pared down to 5, lighter and freer of the physical and emotional baggage.

It all started with 1 storage closet under the stairs. When we moved into our house, we put all of the keepsake boxes in this closet and went to work renovating the rest of the house. With the house almost finished, it was time to turn my attention to this dark portal to the past. I pulled everything out, scavenged any other keepsakes from nooks and crannies throughout the house, and picked up a few supplies:

  • 4 uniform, clear plastic storage boxes ($5 a piece)
  • 3 black cardboard 10×13 photo boxes ($3 a piece)
  • 3 black cardboard 4×6 photo boxes ($2 a piece)

As I sat myself down in front of the stack of full boxes, I reminded myself of the “spark joy” criteria that served me well in other areas. But once I actually cracked the boxes open and started pulling things out, I realized that that wasn’t quite right for these materials. Instead, I set the filter:

    • Would I shed a tear over its loss if it burned in a fire?
    • Do I want my children to inherit this when I die?

Similarly, I found the previously successful trash, donate, and keep piles weren’t a good fit here. Instead I used:

    • Trash
    • Scan
    • Keep

Belly Cast (Box 1)

I put the belly cast from my last pregnancy in one of the boxes and closed it. Having that most special maternal form commemorated forever to see and touch along with the artwork I created in preparation for birth painted on the round belly is precious to me.

Wedding Dress (Box 2)

I pulled out my wedding dress, which was professionally packaged, and set it aside to keep. As a child of divorce, being able to offer my children my wedding dress as a legacy of love to incorporate into their own weddings (or celebrations of love) one day fills me with all the warm fuzzies. I have no attachment to what that incorporation looks like – they are welcome to chop it up and make a pocket square for all I care. But that gift feels important to me to be able to offer as a symbol of the love they were born and raised within.

Rachel’s Childhood (Box 3)

Then I dove into the trenches of my childhood keepsake boxes. Every object I held in my hands took me right back to that moment in time and I had to relive each and every one. I read every word on page after page of writing assignments and friendship notes. I held each choir and colorguard tournament shirt up onto my body.  I set each trophy and token in the light to take in its majesty.

What I found was that all these things that seemed so important when they were packed into these boxes actually weren’t—they just didn’t resonate with me in the way I thought they would through my 17-year-old lens. Time and distance has granted me a broader view in which experiences are weighted differently.

The process of releasing and keeping with intention objects from my past facilitated a therapeutic process. In letting go of the physical baggage, I was able to let go of the emotional baggage that had weighed me down for so long (I’m lookin’ at you, middle school year books). I’m ready to be done carrying this weight and I feel lighter and freer. In keeping particular mementos, I was able to curate my narrative—interpret my journey by writing my story through a collection of special symbols of my past. Powerful.

I found that a lot of the pieces in those boxes were kept so that I could look back at them in adulthood—so I took the time to do just that. I did become a writer, so I read through my old writings that I’d saved for this occasion. I had that experience and those papers served their purpose. I put one in the scan pile and tossed the rest. I did become a mother, so I took out the ponytail I had saved from when I chopped off my hair in sixth grade and marveled at how similar my kids’ hair is to mine, took a picture, and then threw it away. I have a daughter, so she and I had fun trying on my prom dress (for the record, having 3 children made it such that I could not quite zip up the top of the dress), and then I added it to the trash pile.

Mother and daughter trying on her prom dress while simplifying her sentimental box.

Taking a picture of some of these things was a great way to sort of keep it and let go of it at the same time. I mean, I want y’all to remember that I was Grand Champion of horseback riding camp, okay? So, I took a nice photo of the trophy that commemorated my most meaningful competition victory and then added it to the trash with the other 10 participation trophies from sports in which I didn’t have a great experience.

Speaking of pictures, I’m from the olden days when you couldn’t see the photos you were taking on the screen, so you would take like 20 pictures, have the roll of film developed, and see like 2 good shots, but keep them all in a paper sleeve or photo album. This was the way of my era. So, I took the photos out of the bulky albums, kept a few shots that made me smile or saved a particular person, place, or experience, and tossed the rest (goodbye random person I didn’t know who walked into the shot at the beach that summer day).

Let’s be real, this is also where that curation of your story for your children to inherit comes in. I’m not ashamed of any of the experiences I’ve had that have led to me being the person I am today and living the life I do, but I also don’t need 20 pictures from that one rave. One shot of me and my friends dancing will suffice (Can I get an amen?). If you had the privilege of being in any of the silly gems I stumbled upon, you may have received a FB message with a fun little surprise photo during this decluttering period (Sorry not sorry!).

I wrote the year and any other pertinent information on the back of the photos, organized them in chronological order into my 2 photo boxes, and labeled the fronts. I organized the family portraits and photos (pre-digital age) the same way in their own set of photo boxes.

Then the scanning began. Joshua Fields Millburn says that if you call it a scanning party it’s less painful but I call bullshit—semantics can only take you so far (I kid – he’s actually been a huge value add for me, so I highly recommend The Minimalists if you’re not already a fan). I resorted to finding some chic drama to binge (thank you Younger) and Sutton Foster kept me company while I scanned a big stack of little Rachels and then little everyone elses (because in the olden days we had to take our babies to the mall and have fancy photos printed out to hang on our walls). After days of scanning, I managed to make it through all of the portrait photos, but still have to scan all of the 4×6 photos. Progress. In the end I brought all of the 4×6 photos and VHS tapes to Costco for digitization. Worth every penny.

Of important note here is that you don’t want to exchange physical clutter for digital clutter. I have a folder on my computer that automatically backs to the cloud titled Pictures. One of the folders within is named Rachel’s Childhood. Every photo and document in that folder is titled with the year and any other pertinent information (1988 Grade1). If I didn’t know the exact year a photo was taken, I made my best guess. All of the other photos are organized and stored the same way.

After getting the photos settled, I placed fabric pieces in clear plastic bags and included a note with a brief story when the significance may not be obvious to someone else. Again, one of my criteria was around curating my story for my children to inherit. Finding a fancy antique lace baby outfit may not make a whole lot of sense to them but a little handwritten note explaining that this was the baptism gown worn by both my father and me is just enough to create a meaningful heirloom and intergenerational family culture. While I’m not religious, my father and I are very close—that affectionate paternal connection is what makes the contents of that bag special. (Now that I’m looking at the note in the photo below, I really need to rewrite it when not exhausted, lest poor writing becomes saved in posterity).

  • A couple high school yearbooks
  • my 4 graduation tassels
  • my favorite baby rattle
  • a few baby outfits
  • my little blankets that I slept with every night of my entire childhood
  • a plaque with my porcelain foot and hand prints that always hung on the wall of our house
  • the afghan my mom made me
  • a teddy bear
  • my high school class and sweet 16 rings
  • the 2 photo boxes

That basically covers the contents of my childhood box, though I may be missing a handwritten note here or there. The point, of course, is not that you should have the same things I do. What’s going to be meaningful for you will be completely different. I then labeled the box Rachel’s Childhood along with the year span and it was closed.

Horseback riding trophy and ponytail hair on a child's head—items photographed and then released while simplifying childhood keepsakes.

Family (Box 4)

Then I turned my attention to the family box, which spanned the year my husband and I joined forces 18 years ago to present. Loads of generic greeting cards, unimportant papers, and irrelevant technology were purged. In this box I placed:

  • the 2 photo boxes for this time period
  • a few love notes
  • my Krav Maga badges
  • our wedding cake topper
  • a publishing medallion

The biggest bulk in this box was actually outdated media! We had so many memory sticks, tiny disks, VHS tapes, DVDs, old camcorder recordings, etc. that we couldn’t even view! We brought these into Costco’s photo center for digitization and discarded the technological relics. You guys, Joshua even had some floppy disks. I just can’t even.

Joshua’s Childhood (Box 5)

Pulling in my husband to go through the tech was a gateway that, along with the finished product he could see of my childhood box, inspired him to go through his childhood box as well. He read every word on every page and tossed a ton just like I had. I helped organize all his photos into those 2 photo boxes for portrait scanning and Costco 4 x 6 photo and outdated video digitization and we placed all of his childhood keepsakes into his box. It was actually a really fun activity to do together and we had some really good laughs. Seriously, it would make a great date night.

Kids’ Keepsakes (Boxes 6, 7, 8)

Each of my 3 children has 1 keepsake box. This system is actually brilliant as they have a defined and manageable space in which to prioritize their childhood keepsakes. In other words, they won’t have to go through this process upon launching. Their boxes contain things like:

  • artwork
  • writings
  • a couple baby outfits
  • a couple baby blankets
  • baby teeth
  • bronzed hand and foot prints
  • some junior ranger badges from trips to national parks
  • the embroidered Peter Pan hat that Bay wore every day for years
  • the Tula Toddler that West rode everywhere in for years

Toy Keepsakes (Boxes 9, 10, 11)

In the last few months, we have also donated a solid 80% of the kids’ toys, materials, sets, books, etc. (you can see a picture from before the mass toy exodus of 2018 here). We actually cultivated a very intentional playscape for our 3 homeschooling children and the letting go of so many toys and materials was less about minimalism and more about a season change in the development of our kids and their play. This is part of the “sweet” to the bittersweet of your children growing up.

Why am I bringing this up in a post about keepsakes? Because we have decided to keep 3 sets (boxes) as keepsake toys that I would like to be able to gift to my grandchildren one day – the most beloved toys of our children that are high quality and have been played with so happily for years on end (like the wooden Thomas Train collection). For now, these toys still live in the playscape but eventually, they will be stored with the keepsakes.

Holiday Heirlooms (Box 12)

Our Christmas boxes also live in this closet. I had already let go of the holiday things that filled me with a sense of obligation or overwhelm instead of holiday cheer at Christmastime, cutting down my stock from 8 boxes to 4. I have such a special affection for wintertime and the holiday season so releasing the clutter to let the treasured sentimental holiday keepsakes sparkle and shine was such a positive experience. While most of this box real estate is taken up by easily replaceable things like lights, there is a box of special keepsakes like heirloom ornaments and handmade stockings that spur winter solstice magic for our family. This box is a keeper.

Childhood keepsakes and photos simplified, scanned, and organized


These are the 12 boxes that we would choose to store even if we launched into nomadic living. We have set 12 seats at the keepsake table for our family of 5. After having a few tough moments feeling defeated by those sentimental boxes from the past, I feel so much lightness, peace, and optimism. The baggage has been released, my story has been curated, and I have a system I feel great about in moving forward. I can sit here in my home feeling genuinely comfortable and confident with my non-sentient entourage. Even that darkest hidden corner closet has been flooded with the light of simplicity.

Comment below with any tools, techniques, or lessons you’ve found valuable for your family on this simple living journey!

  1. Elise says:

    Have you heard of legacy box? I haven’t used it personally but have heard great things about it. It’s exactly what you need for your outdated media… if you haven’t found a solution already.

  2. I need to do this so badly! Thank you for the encouragement!!!!

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I work from an island in the Pacific Northwest, where I live wild and free in connection with my hilarious husband and three growing sailors in our fixer upper on the beach. I authentically live this healing work out loud raising my own neurodivergent family (inner child included) and draw on my decades of education and experience (I've done all the nerdy work so you don't have to) to guide a revolution of overwhelmed parents just like you to feeling at peace within yourself, consciously connected with your children, embraced by a supportive community, and enjoying a values-aligned life you love.

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