If, like me, you’re north of forty, there’s a good chance you have more papers in your possession than subsequent generations. What in the world should we do with them all? What about those that carry emotional weight? This month, we are talking about sentimental papers and how we can rightsize them without losing a part of ourselves.

As a member of Generation X, I straddle the analog and digital divide. I still have actual letters, written in cursive no less. Can you also remember a time before email and cell phones? Typewriters, word processors, and carbon copies were in our purview. Do you recall the smell of the purple mimeograph ink that would get all over your hands?

Rightsizing sentimental papers is one of the final frontiers we cross with our organizing clients. It’s best to start with the low-hanging fruit and easy wins like furniture, the junk drawer, or other spaces with little emotional attachment. This builds momentum and helps our clients strengthen their decision-making muscles. If we start with the sentimental stuff, like photos, books, and papers, we get bogged down.

Each piece of paper is a decision. If you go through an entire box of paper, that’s hundreds of decisions. (Whew, are you feeling overwhelmed yet?) Most of us have more than one box of papers lurking in our homes, taunting us from the garage, closet, or attic. Of course, it can be difficult to feel motivated to drag them out and begin. (BTW, If you’re looking for advice on handling regular, everyday papers, please check out our previous blog post here.)

True confession: although I’ve rightsized most of my possessions, I still have six banker boxes of sentimental papers and mementos. Over the years, I’ve made passes through them and lightened the load a bit, but not as much as I’d like. One friend who’s a millennial proudly owns only six pieces of paper (her SSN card, birth certificate, etc.). That’s truly impressive, but how do you do this if you’re not superhuman?

Two of my six boxes contain journals and letters from my two-year stint in the Peace Corps. Of course, I intend to write a book about them “one day.” When will that day come? When I’m “less busy?” When I retire? If it were a priority, wouldn’t I have written the dang book by now? One of the hardest parts of rightsizing sentimental papers (at least for me) is identity. By letting go, are we also letting go of who we think we are/were/want to be?

We also want to leave a legacy, to know that we matter. So how do we let go of sentimental papers, yet maintain our sense of identity, and shape the legacy we’d like to leave?

Here are some tips to rightsize your sentimental papers (and preserve your memories):

Emotional Journey

Diving into our sentimental papers is an emotional journey. It can bring up fear, guilt, and nostalgia, among other emotions. So, as you go through the process, take moments to reflect on your life. Consider the lessons you’ve learned and how you’ve grown. This can add a therapeutic element to rightsizing.

Tangible Memories

Try holding onto the idea that physical items (including papers) are just vessels for memories. Instead of collecting physical items, consider capturing the essence of the memory associated with the item. For example, writing about a memory associated with a particular letter might help you capture its essence, and then you can let the physical item go. Consider scanning or burning the writing afterward (so as not to create more sentimental papers).

Story Sharing

Share stories associated with your sentimental papers with family or friends. This might help in preserving the memory and making the process of letting go easier.

Quality Over Quantity

Having a few carefully chosen items can be more meaningful than boxes of clutter.

End-of-Life Considerations

While it might seem grim, considering what will happen to your sentimental papers after you’re gone can be a motivating factor to rightsize. For example, think about what leaving behind a clean, organized legacy will mean for your loved ones.

Ask for an Outside Perspective

Sometimes, it helps to have a non-judgmental friend or family member sit with you during the rightsizing process. They might offer a more objective perspective and help you decide what’s worth keeping.

Set Quantitative Goals

Having a tangible goal can guide the rightsizing process. For instance, decide to reduce your collection of sentimental papers by 50%.

Memory Box

Create a small “memory box” that you allow yourself to fill with your most precious sentimental items. This can help prioritize what’s most important.

Creative Repurposing

Instead of letting these items sit in a box, think of creative ways to display or use them. For example, use letters to create an art collage, or scan them and create a digital scrapbook.

Security Concerns

When disposing of personal papers, consider security. Shredding documents that contain personal information is important to prevent identity theft.

Time Capsules

For some items, consider making a time capsule to be opened in the future. It can serve as a fun activity, especially if you have kids, grandkids, or younger family members.

Moving forward

I’ll let you know when my Peace Corps adventures will be published. Meanwhile, I’m keeping my top three high school English papers, a few favorite awards from elementary school, and a doodle series I created with a locker buddy in the eighth grade.

If you’d like some gentle accountability and non-judgmental support with rightsizing your sentimental papers, please reach out. Our team would love to help.


Whitney's pictureAbout Whitney Zeigler

Whitney is the founder of Big Rocks Organizing and a Certified Professional Organizer©. She enjoys reading, hiking, gardening + rollerskating.