Week 9 – Memorabilia and Sentimental Items

It’s Week 9 of the 2022 Clever Girl Organizing Challenge! We’re in the home stretch, the final 3 weeks and they’re all meaty and valuable categories, so stay with us!

For a lot of people, this may be the toughest we’ve faced. Even Returning Challengers likely have work to do here. But the work we’ve done up until now has strengthened our muscles and decision making, and I know we’re ready! 

Don’t forget the two guidelines I’d love for you to keep in mind before you start your work:

1) Have the tools you need before you get started — trash bags, recycling, donate box, and “goes somewhere else” box (so you can set things aside and keep going, not be tempted to return things to a different space while you’re working).

2) Keep up on that BEFORE and AFTER picture taking! I see people saying “Shoot! I forgot to take a before picture” and then they know they’re missing out on expressing to everyone just how tremendous their transformation was. 🙂



So, what are the categories and spaces you might consider this week to tackle? Remember, you don’t need to do ALL of this! I want to give you ideas of where your time might be best spent, based on YOUR needs in YOUR space. Think about what you have, what you know you haven’t looked at in a while or what you know causes some strain on your storage systems. Most importantly, think of who you are, your current and foreseeable lifestyle, and what items just don’t align with that any more (if they ever did)!

This week is about facing our past, and making considerations about what parts of our past do we actively take forward with us into our future. It’s not about asking you to let go of it all, or even of any of it. As with everything in this Challenge, it’s asking the question of ourselves: “What do we own, and why do we own it?” It’s about actively answering that question, not just holding onto things because we always have before, or because it fits in our storage or isn’t in our way. It’s about actively reviewing and validating these items and actively recommitting to owning them, or deciding that it’s okay to leave some things in the past, and it doesn’t change who we are or the future ahead of us. 

In some cases, this week is also about considering the way or the place we store things. We might rehome some items into better storage options, smaller containers, different spots that make it easier (or harder) to find. We might decide to display items that we loved and were packed away and forgotten about, and we might decide to pack away items we don’t feel the need to see every day anymore. In some ways, if things are just inventoried and organized better, especially if they’re important and how you care for them may impact their longevity, you’ll feel like you’ve made a big impact on this weight. 

Take this week, and if you need it, next week, to come up with a plan and start reconnecting with your mementoes and memorabilia, and making some reflection on what you own and why own it. Consider that there may be ways of slimming your collection, like taking photos of items before letting them go, keeping a percentage of items from a category while still keeping a core collection.  Head to the “Why is this so hard?” section for a LOT of questions to help you frame up why things feel so sticky for you, and how you might move forward with some of the hard work of letting go, if that’s your goal. 

What are some example categories that fit here: 

  • Photos – printed or digital
  • Greeting cards and letters you’ve received (the meaningful message-filled ones as well as the ones I call “autographs”  or the ones you know were just attached to a present so you knew who the gift was from)
  • Event Mementoes (like concert tickets stubs, news clippings, event programs, receipts) 
  • Items that you associate with moments you wanted to remember at the time (SO many examples, but a few might be: graduation tassels, corks from champagne bottles, pressed flowers, high school varsity letter, etc.) 
  • Your Kids Artwork / Schoolwork 
  • YOUR school papers and artwork from your youth
  • Religious items
  • Old journals
  • Travel Souvenirs
  • Gifts we’ve received 
  • Home movies
  • Old planners and calendars
  • Baby Items (yours or someone else’s) – teeth, hair, hospital bracelets, bronze baby shoes, baby clothes, etc.
  • Old IDs (personal, work, student, whatever)
  • Keepsakes you’ve found along the way that spoke to you – rocks, shells, coaster, matchbooks, quirky items, postcards, etc. 
  • Awards, Ribbons, and Trophies
  • Celebrity items – photos, autographs, sports mementos, etc. 
  • Hobby/Collections – coins, stamps, sports cards, trading cards, models, dolls, stuffed animals, stickers, etc.
  • Items that were SOMEONE ELSE’S memorabilia that you’ve inherited. 

I’m sure you can add even more as you think about your own life!

Remember, you’re making decisions based on the value the items play to you in your current and foreseeable future and recognizing that anything else is probably clutter, and clutter is getting in your way of using your home the way you want to. This is why we’re doing this work; to cut down on the cost of clutter in our lives. 


Each week, we have 3 levels for you to engage in. Pick the one that feels like it will work with your time, energy, and needs for the week. You can always rally later in the week and do more! If you’re managing your time closely and can’t do a lot in one session, see what you can do in a 20-Minute Attack. Set a timer, stay focused, and see what you can accomplish in less time than it would take to watch a sitcom! And let us know what you path you’re on each week with the hashtag #tackleit and then the week we’re on, for example: #tackleit  #week9

This week, I’m not going to list out different options under each category from the list above; they’re just going to be based on your ability to set your own goal and size up your energy and your needs. 

All Aboard (This is the normal challenge level):
PICK 4 CATEGORIES OR COLLECTION SPACES (drawers, bins, cabinets, boxes, etc.) 

MiniChallenge (for people with limited time or energy this week)
PICK 2 CATEGORIES OR COLLECTION SPACES (drawers, bins, cabinets, boxes, etc.) 

LevelUp Challenge (for people with more time, energy, or greater need)



Our Memorabilia is from our past. In some cases, it’s from ALL of our past: our youth, from our former (and current) romances, our friends, our college days, our careers, our travels, or handed down from our family members to treasure. They are mementos from people who have left our lives or passed away, tokens of their identity and our relationship with them. 

They are from great moments, or sad moments, or even from a moment that wasn’t very special, but the way we remember it is. They’re from moments that, at the time we said, “I want to mark this occasion, and I’m going to hold onto this item to do so.” They are our “stuff alibi” that shows the trail of where we’ve been. 

Our collections and our hobbies, the leisure pursuits we’ve enjoyed over the years, can be keepsakes and memorabilia. Collections have been built not only in our hunt and search for treasure, but with gifts others have thoughtfully added to our collection, even if we weren’t actively growing it ourselves.

Keepsakes and memorabilia can be everywhere, but their mere existence isn’t a problem. So, when do sentimental items become a problem?

We love the emotions we feel when we touch and revisit them. Our hearts warm and we sigh for the past. We can get lost in our memorabilia for hours! But there can be a point where we know that we are just holding on to too much of it. Maybe it’s driven by space needs, or just knowing how much is around us that is weighing us down, or how much work it will be to deal with when we want to move. It could be preventing us from moving on after a loss or after a change in life. We may even address these things because we just don’t want our loved ones to have to deal with all this stuff after we’re gone

If we have a goal of reducing what we have, and our sentimental items are part of it, we get there by saying to ourselves, “I enjoy the memory that this item conjures up for me. But I can live without it, especially if it helps me get to my bigger goals for my life now. I can let go of this.

It is when we can’t bring ourselves to say that statement, when we just can’t let those items leave our lives, that we recognize our barrier is going up, and it is preventing us from letting go.

At first, the barrier feels like a general unwillingness, and it can be strong enough to not look past it. However, the barrier, deep down, once again, is usually fear:

  • We are afraid of feeling like we’ll lose part of ourselves if we part with an item.
  • We fear the thought of parting with those items, as if we’re either betraying our past self, or someone else.
  • We are afraid we’ll lose the memory itself, and our ability to revisit or share our story, without it. (Or that others won’t be able to tell our story after we’re gone, and we hope they would.)
  • We believe we’ll want to continue to revisit these emotions time and time again, and fear that, without this keepsake to hold in our hands, we won’t be able to recapture the joy. Not being able to recapture joy seems like something to avoid!

All of those scenarios, those emotions, we tend to want to avoid. Forever.

We all love our collections and our walks down memory lane and should have some keepsakes for our ability to do that. I’m not suggesting that we shouldn’t hold onto meaningful things. Think about your goals and decide whether holding on to too many items that have little or no other value besides “triggers old memory” take up more of your home than you feel they should, given how you want to live in the space. 

Since we’re talking about the sentimental, and not the practical, we need some “big picture” philosophical questions to help guide you through it and help you understand the role each item plays in your life. These are meant to help you see the difference between items being memorable and items being important. Just because something triggers a memory doesn’t mean it is also important to you.

As you think critically about items, ask:

  • What do you gain from keeping this? What do you lose from keeping it?
  • What do you gain from letting it go? What do you lose from letting it go?
  • What would your past-self say if it knew you still had this, and what would your future-self say if it knew you let go of it?
  • Are you keeping it primarily because you want someone else (child, grandchild, etc.) to find it as emotionally valuable as you do, maybe even after you’re gone? (kids’ artwork and old report cards, anyone?) And, do you know for sure they will value it as you hope they will? (We’ve talked about this in a previous week around “Perceived Value to Someone Else”)
  • Are the memories and the keepsake even yours, or are they the memories of someone else, that have ended up in your hands through gift or inheritance? Is the item important to you, or is that person important?
  • Does the item bring you sadness or make you feel bad about yourself or someone else? Sometimes, our memorabilia bring up negative feelings: guilt, sadness, regret, heartbreak. Yet, for whatever reason, we still feel committed to holding onto these things to rekindle the memories of our life’s experience. Is holding onto things that bring about negative feelings really a good thing for you and your home?
  • Are you keeping it because someone else expects you to, but it doesn’t mean much to you, personally? In other words, is the primary emotion you attach to it obligation or guilt? (yep – there’s that GUILT again!)
  • If someone you care about accidentally came across this item, would it be awkward or upsetting to them? 
  • Do you really know WHY it is so important to you? Are you just accepting an easy, on-the-surface answer, or is there a deeper meaning behind your attachment to this, and you’re not facing it?

Okay, they don’t ALL have to be big and heavy questions. There are some practical questions we can ask, too:

  • How much space of your very valuable real estate and storage space are you willing to allocate to items that don’t have a function, but only serve to generate memories when you revisit them?  Can you set a limit to the space, and then prioritize what ends up in that space?
  • Do you have more than one item that reminds you of that person, place, or moment? Would you be okay if you kept only one or a small set of those items? This comes up so often when going through things like children’s old clothing or artwork. I know how tough this is; be disciplined with yourself with this!  Do you need ten outfits from when your child was growing up, to help you remember they were that age once, especially if you have a picture of your child wearing it? Do you need every rainbow picture that was finger painted?
  • Can you rank importance among them? Set up four piles, and rank what goes in each:
    • I could never, ever, ever let go of this item, and if the house caught fire, I’d rescue it.”
    • I am glad I’ve kept this. I enjoy revisiting it occasionally, if I stumble upon it. If it were gone forever, I’d miss it, but it wouldn’t really impact my life.
    • Hmm, I kept it at the time, but I don’t need it anymore. Sure, I remember a moment when I look at it, but it’s not a critical part of how my life has turned out.”
    • “Honestly, I have no idea why I kept this in the first place.”
  • Do you need to keep the item as it is, or could you take a photo of it? Scan copies of cards or letters? Create a digital scrapbook? Capture it all in a cloud-based collection of images or videos that you can keep for yourself or share with others electronically? Or turn into a collection in a shadow box? Or a keepsake quilt? Do you need the whole item, like the program from the school musical you were in, or could you edit it down to just the parts that are meaningful?
  • Do you truly have the space to store and display your collection at its current volume? Has your collection taken over space that would be more valuable if used in a different way?
  • Are you able to appreciate the collection with how much you have, or have the special pieces been lost in the numbers?
  • Is there someone else who’d love to have the keepsake for their own memories? This is a good way to think about family heirlooms… you may have other family that would love them, too.

As you walk through these questions, you should start to feel a difference between what you can let go of and what you won’t. It gets easier over time, as you become stronger at finding the clarity in what is important for your future, and not just evidence of your past. It can also get easier over time, if the pressure to reduce your possessions means you need to make deeper cuts into what you’re keeping. When you have no choice, you stop allowing yourself to choose.

If you were to walk away with three important ideas about managing your keepsakes and memories, I hope they would be:

  1. Write your stories down. Not only does this help you capture your memories, but it helps share them with others and pass on the stories after you’re no longer able to tell people about what is important to you and why.
  2. Honor what you’re keeping. If your keepsakes are in a box in the basement or attic and you never look at them, what value are they really playing in your life? If items are important to you and bring you happiness, can you make them more prominent in your life? If something is not important enough to be featured prominently, are you questioning why you are holding on to it?
  3. Remember that our stuff is stuff. It is not our memories. It is not the people we love. Our memories are in our heads and our hearts. 

My hope for you this week is that you’re able to listen to those barriers or these rationalizations/justifications that come up and you’re able to ask yourself: 

What is the real role these items play in my life today, and in my foreseeable future? Why am I valuing these items as more important than the other things I’ve been working hard on all this time, struggling with storage space, cleaning, maintenance of spaces? What am I gaining TODAY by keeping these items? 

    Remember: You’re here because you made a choice to bring your head, heart, and body all in the same direction: to let go of things and have smoother systems in your home. If it was easy, you’d be done by now.




    This week is a heavy one for all of us. Be kind to yourself as you go through this stuff. Share your stories, the fun treasures, even the “I’m taking a photo of this before I let it go” in the Facebook Group. We’re all going to go through this together! I can’t wait to see what you’re tackling and learning what you’re facing and deciding as you go!

    And if Memorabilia isn’t heavy enough, it’s a perfect week to tune into (or watch on replay) this week’s Facebook Live: How to deal with not being on the same page with your spouse when it comes to clutter and organizing. ALL THE TIME I deal with clients who have differences in perspectives and preferences, but MEMORABILIA is a big trigger for both sides of a couple. Whether your the holder-onner or your spouse is, let’s focus on it this week! No magic answers to share, but some perspective to help us navigate through tricky waters. 


     Happy Organizing! 





    TUESSDAY, MARCH 1ST  – 12:00pm Eastern







    Week 1 – Jan 3: Kitchen: Food – Pantry, Fridge, and Freezer
    Week 2 – Jan 10: Kitchen/Dining: What we use to prep, cook, serve, eat, store, and clean after eating! 
    Week 3 – Jan 17: Bath and Bed: Medicines, Toiletries, Cosmetics, Personal Items, etc. 
    Week 4 – Jan 24: BREAK – take a break, catch up, or sneak ahead
    Week 5 – Jan 31: Clothes, shoes, accessories
    Week 6 – Feb 7: Living / Family Room spaces
    Week 7 – Feb 14: Kid stuff / Holiday Decor / Pet stuff (Choose Your Own Adventure)
    Week 8 – Feb 21: BREAK – take a break, catch up, or sneak ahead
    Week 9 – Feb 28: Memorabilia
    Week 10 – Mar 7: Home Office/Papers
    Week 11 – Mar 14: Hobbies / Arts and Crafts / Sporting Goods