8 Questions to Help You Let Go of Your Hard-to-Let-Go-of-Things

She’d had an easy enough time getting rid of the crib, the pack n’ play, and the baby swing. They were bulky, and she was happy to get her space back.

As her children grew, even their clothes were relatively easy to part with, because most of the time, those clothes had been worn to threads. Grass stains and ripped knees weren’t too tempting to keep.

But her kids were getting older now, and after years of trying for a third baby, Shana and her husband had finally decided that their window for a third child had come and gone. They were a family of four, and Shana—who had always pictured herself as the mom of big, wild brood—was slowly wrapping her mind around that idea.

Deep in her gut, she was at peace with where her family was. But a small part of her still mourned her lost dream, and she was okay with that, too. (After all, happiness and loss can coexist.)

When You Just Want to Hold On

It was these feelings that explained the things tucked away at the top of their closets and the back of their attic.

The wood blocks and tubs of colorful Legos she’d watched her son and daughter play with for hours and hours during their toddler and early childhood years? Maybe she’d save those for the grandkids someday.

The boxes and boxes of art, school projects, and sports memorabilia? Who knows what the kids will want to have someday, she told herself.

Six of her daughter’s favorite stuffed animals and fifty of her son’s treasured Pokemon cards? Even she could admit she was far more attached to those things than either of her kids were.

For months, her husband had been gently prodding her to clear out some space. He offered to go through everything himself, but Shana couldn’t let him do it without her. Items that weren’t sentimental to him certainly were to her.

The Turning Point

It was when her best friend’s mom passed away unexpectedly—leaving Shana’s friend and her siblings with a house full of things to sort through—that Shana really started thinking. She planned on having a LOT of years left, but life suddenly felt a little more fragile than it had just a few weeks before, and she decided she was ready to at least start letting go.

{10 Clutter-Clearing Strategies that Will Gradually Make Your Life 100 Times Easier}

8 Questions to Help You Let Go of Your Hard-To-Let-Go-Of Things

The next time you’re in Shana’s position, holding on to something (or many somethings…) because your heart is tied up in the process, try asking yourself these questions to assess the real cost of storage and your real vision for your home and your life.

1. Would I rather store this item indefinitely—or borrow or even re-buy this item if the need were ever to arise down the road?
2. What could I have done with the time I’ve spent organizing my things, searching for items that have gotten lost in my clutter, or debating about what to keep and what to pass on?
3. If I reduced what I own and stopped spending so much time managing my things, what would I like to do with that time going forward?
4. Does my home visually represent the person I’m trying to be?
5. Will this piece that’s meaningful to me mean the same thing to the person I might one day pass it down to?
6. Does getting rid of this item mean I’ll be getting rid of the memories associated with it?
7. Is there a different way I can document or honor what this piece means to me without actually holding on to it?
8. Who will sort through my belongings after I’m gone, and what can I do now to lessen that burden? {9 Hard Truths About Clutter You Need to Hear}

Shana made some great strides the summer after her best friend lost her mom. She made space at the top of their closets, and she narrowed down her collection of sentimental things to just one chest she kept at the foot of her bed.

But most importantly, she felt a lightness she didn’t know she’d been missing.

“What I know for sure is that when you declutter—whether it’s on your home, your head, or your heart—it is astounding what will flow into that space that will enrich you, your life, and your family.” Peter Walsh

Need More Help Letting Go?

In my work with hundreds of women on a mission to declutter, I’ve found it so interesting that different perspectives—different questions—get to the root of the issue for each of us. Sign up below to get a PDF of even more questions just like these… You never know what could be the turning point for you!

I’d love to add to this list! Do you have any questions you ask yourself when you’re debating what to keep and what to let go of? What thoughts or perspectives have helped you let go in the past?