Are you holding onto sentimental things because you feel too guilty to get rid of them? Items like old photos of a cousin’s wedding or Dad’s old bowling trophy certainly have history. But the reality is, we often don’t want, need, or have space for them. Yet compelled by guilt, we believe we should keep them anyway.

Keep them and what you’re really doing is punting the decision down the road for another 30 years, probably even to your heirs. You could be cluttering your house with possessions you don’t even look at, and that family members don’t want.

We advise streamlining by snapping photos of items and creating digital memories. After that, here are gentle and meaningful ways to let go of common sentimental articles that you can’t bear to throw away.

Need help with downsizing? Contact our professional organizers today for help!


We have found as many as six generations of family Bibles collecting dust in storage. How did they get there? Probably each generation felt guilty about throwing them out. Don’t be victimized by tradition! Ask family members if they would like to have one. If you get no takers, donate the good books to an area church.

National Flags

People who own national flags tend to believe strongly in their national identity. For them, the flag is a potent symbol. Honor those beliefs by disposing of the flag in a respectful way. If the flag is in good condition, you can donate it to a local Scout troop or veteran’s organization. If they can’t find a use for it, they will dispose of it ceremonially.

Wedding Dresses

When cleaning out the attic of a recent client we found three generations of wedding dresses. Seeing them all lined up was romantic, but in all their years of storage, how many times do you think they saw the light of day? Probably none since they were passed on by their prior owners. If you can’t bear to let go of your own wedding dress, keep it. But if you’re holding on to Great-Grandma’s because you think you should, don’t. Ask family members if it’s something they would like to have. If the answer is no, donate the dress to a charity, or sell it to a vintage shop.


Photos show such intimate moments we can feel pressure to keep them, even when they’re of people we don’t know. But they often just sit in boxes and drawers and rot. Instead, sift through them one by one. If no one living knows the details of those pictured, sell the photo. (Yes, there is a market for old photos, and slides are even more valuable.)


There’s a difference between finding one trophy and 100. We have found Olympic medals and Heisman trophies in houses where Grandpa was clearly an important sports figure. There may be an organization or museum that would love to take an award or collection like that. But if we’re talking a gold-painted metal cup stamped with ‘1956 Bowling Champion,’ give yourself permission to simply let it go.

Sports Memorabilia

What about Dad’s old varsity letter jacket? If he was famous, finding a buyer will be easy. Otherwise, a member of the younger generation might want the jacket. If that doesn’t work, donate the item to a vintage shop or donation center. Believe it or not, someone would love to transform it into a trendy, vintage piece.

Military Uniforms

If you have an old military uniform, you’ll want to keep the patches, hat, and any medals. These can be stored in a cigar box and passed down to an interested family member. To learn where to donate the uniform, call the local office of the corresponding armed services branch and ask about organizations that accept donations.

If you can find a home for sentimental items you can’t bear to throw away, then you can free yourself from guilt and let go of items you no longer use. Remember, if you aren’t actively using them, you’re running a storage business for items that never see the light of day.

For more tips on what to donate, read our blog here.

Learn More About Senior Moving

WayForth is your go-to senior move management company. Our professional movers help with downsizing, packing and unpacking, storage services, and more. Contact today for a consultation!

About the Author: WayForth

WayForth is the definitive provider of comprehensive and personalized moving solutions for life and business. Since 2016, WayForth has led the way in move management, providing solutions to over 15,000 individuals and families. How you move matters and no matter the destination, WayForth serves as a guide making life’s transitions easier to navigate. Call 1.844.WAYFORTH today to learn how we can help with your next move!
Wayforth newsletter

Join the List

Sign up to receive our blogs and stay in the know about industry downsizing and moving tips.

Get access to our e-book

Navigate the most challenging aspects of probate with ease, including sensitive emotional matters, by following our expert guide.

WayForth is a Proud Supporter

June is Alzheimer’s and Brain Awareness Month. Join us and #GoPurple in support of the more than 6 million Americans living with Alzheimer’s.


You’ve got questions – we’ve got answers!