How to Deal With Sentimental Clutter Like an Organizing Expert

Weeding through stacks of sentimental clutter can be time-consuming and emotional, but it doesn't have to feel like getting a root canal. As someone who's spent over a decade helping people declutter their homes and lives, I'm rounding up my best tips to help you tackle your memorabilia.

But first, what is sentimental clutter? Sentimental clutter typically includes items like letters, photos, heirlooms, and mementos — anything kept because of an emotional connection rather than functionality or necessity. Of all the categories of belongings I've helped people edit and organize, sentimental clutter tends to be the most difficult for people to confront. This is due to internal conflicts and questions such as:

The struggle is real, but I promise this daunting task can be less painful than you think if you follow these simple steps.

How to Organize Sentimental Items

Commit to a Time Frame

Decide how much time you want to spend decluttering and stick to a specific time frame. Play to your strengths: some people prefer blocking out an entire weekend to overhaul their storage spaces, while others do better with an hour or two each day over several weekends.

There's no "right way" — only the way that's right for you. If the project feels overwhelming, start with just 15 minutes a day. This small, manageable chunk of time will help you break out of procrastination and get into action. (See: my 15-minute decluttering wins.)

Set Yourself Up For Success

To ensure an efficient decluttering session, gather some basic supplies: a recycling bag, donation bag, and a few bags or boxes for items you'd like to give to friends or family. If you have heirlooms of value, you might want an additional box for the things you'd like to sell or consign. Keep a pad of sticky notes and a pen handy to label items that need to be sent off.

Set a Physical Boundary

Creating a clear physical boundary for how much you want to keep can help you make those tough decisions. Think in terms of available shelf space or the number of bins you have room to store. When my mom surprised me with a dozen storage bins filled with my childhood mementos, I decided to whittle the collection down to just two bins for our basement. This constraint made me edit ruthlessly, and I was able to keep only the best and most meaningful items.

Determine What Makes the Cut

Before diving into the decluttering process, set clear parameters to decide which items should stay. For example, if you're sorting through a box of photos, you might choose to ditch duplicates or images that are yellowed or stuck together. For childhood art, consider taking digital photos of your favorites and recycling the rest. If you're tackling yearbooks and school awards, maybe you decide to keep just one from each school year. Deciding what you want to keep ahead of time will make the process more efficient.

Ask Better Questions

As you sort through your sentimental items, try to avoid questions like, "Could this be useful one day?" or "Did someone give this to me?" These questions are rooted in guilt, obligation, and fear, and they can justify keeping almost anything. Instead, focus on questions that help you keep only what supports your current space, values, and lifestyle. For example:

The goal isn't to be careless or get rid of everything, but to focus on keeping things that are truly meaningful and functional for you in the present.

More Memories, Less Clutter

It's easy to feel like letting go of an item means losing the memory associated with it. The good news is that memories don't live inside your stuff — they exist in your mind and heart. If you're a visual person, consider snapping a picture of sentimental items before parting with them. The photos can serve as a reminder of the people, accomplishments, or experiences you want to remember. All the memories, none of the clutter. Win!

One and Done

If you're facing large collections from your past, consider keeping just one token item. This strategy is a great space-saver if your storage areas are cluttered with boxes of comic books, baseball cards, vintage clothes, or other collectibles. Get creative: some clients have turned pieces of their childhood collections into art installations, quilts, or framed items in shadow boxes to display in their homes.

Digitize and Declutter

If you're struggling to make tough cuts, digitizing your old letters, photos, art, and mementos can be a great alternative to storing physical items. Find a bulk scanning service in your area or, if you have the time, scan and save them into organized folders yourself. Label folders with broad categories like "Letters From Dad" or "Wedding Photos" so you can easily find what you need. No time to DIY? Services like Artkive can turn a massive pile of kids' art into a beautiful keepsake book.

Pass It On, Pay It Forward

When it comes to valuable art or heirlooms, remember that they're not doing anyone any good collecting dust in your basement. If you find nicer items that you don't have room to store or display, check in with friends and family to see if they'd like to keep them.

If no one in your inner circle is interested, consider donating them to your local community. Theaters, churches, community centers, non-profits, and schools are often in need of donations. Don't waste time dwelling on the sunken cost; it feels great to free up space in your home and even better to be generous and make a positive impact.

Display the Most Meaningful

It's always struck me as strange that we often store our most precious items in dusty attics, basements, or garages. Decide which sentimental items are most meaningful to you and find a way to display them in your home so you can enjoy them every day.

My father's favorite mac and cheese recipe is framed in our dining room, and it brings me joy every time I see it on my way to the kitchen. If you're looking to invest and have an item that's not easily framed, The Heirloomist is a service that turns your most precious memorabilia into modern art.

Some resources for storing and displaying include:

Going through sentimental clutter can be tough, but it doesn't have to feel like emotional torture. Stay focused on keeping and displaying the items that add value to your life. The rest is just clutter.

Shira Gill (she/her) is a globally recognized home-organizing expert and author with a minimalist philosophy. She's inspired thousands of people to clear clutter from their homes and lives through a process she developed that applies to anyone, regardless of budget, space, or lifestyle. Shira is the bestselling author of "Minimalista," "Organized Living," and her new book "LifeStyled," and has been featured by 100+ media outlets. Shira is a PS Council member.