My nephew Oliver clutched his fist and looked up at me with hesitant blue eyes. “Aunt Jenny,” he said tentatively, “I think I might want to give this to Gia.” He uncurled his five-year old fingers slowly, almost apologetically, to reveal a tiny worn silver heart. Gia is Oliver’s first puppy love - a romance that hadn’t yet bloomed at the time I’d given him the heart as a reminder of my love across the miles separating us between Texas and Ohio.

Puzzled, I squatted down to his level. “Oliver, that sounds like a really nice thing to do. What’s wrong?”

He furrowed his little brow, searching for the right words. “I don’t know how to explain it, but when I have special things, I worry if I give them away, I’ll never see them again.”

I smiled as a lump formed in my throat. I was taken aback by his “from the mouths of babes” wisdom. Oliver had captured the crux of the chronic tug-of-war so many of us have with our possessions—and had confessed how we all feel: we just want to keep what matters most to us. But how much is too much?

We all have treasures like Oliver’s that represent a time, place or person in our life. They’re a way we bottle memories. An on-demand fix of a bygone comfort, joy or lesson. As a self-proclaimed sentimentalist, I celebrate surrounding oneself with meaningful things, things with a story. To me, that’s what makes a house a home. Or brings a sense of soul to an office. It’s what creates that cozy, warm apple pie feeling I so adore; an appreciation I’ve noticed has grown stronger as I get older, become more aware of the passage of time, and say “goodbye” to people and places that created my original sense of home. 

At the same time, I’ve also become aware of the slippery slope of a sentimentalist: too much apple pie quickly converts comfort food to an empty-calorie-sugar crash.  Just like too many trappings transform ‘sentimental chic’ into cluttered chaos: a state that makes your house less of a haven, and more of a headache, whose piles and projects endlessly taunt you at every turn. And when it starts to give you that tight feeling in your chest? Ding-dong. That’s your cue that it’s becoming too much - becoming clutter.

Even I, as a clutter coach who helps others prune their lives, have wrestled with this. In the years that my late father progressed with ALS (aka Lou Gherig’s disease), I tucked away more things than was typical. ALS was a terminal illness after all, so my tendency was to proactively stockpile anything that would remind me Dad once he was gone. The struggle was real!  But so is the reality that too many of these possessions will hinder me. Chalk it up to physics or psychology or spirituality, but I know that hanging on to too much from the past will prevent me from moving forward into the future.

So, amid the piles that can seem so daunting, where does one even begin? How do we avert our own apple pie binge?

Take heart. Take a picture. And take a lesson from Oliver.

1. Accept the struggle is natural - not just another bad-habit you should lambast yourself for. Struggling to let go of sentimental items is completely natural, not necessarily pathological. In fact, those who on the surface easily purge every last possession, with no regard for legacy, have their own set of issues brewing inside. So celebrate that you have a history rich with beloved people and memories worth preserving. (Inhale. Smile. Exhale.)

2. Now, let go (there, I said it). Not immediately of the teasured things, but first and foremost, of the belief that you should join the minimalist movement. Or live in a tiny house. Or have perfectly pristine countertops. Let go of the expectation that you should conquer every last bit of stuff in one fell swoop. Instead?

3. Take a small, single first-step: snap pics of cherished items, jot down the memories they capture (perfect grammar not required), and capture them in an old-school album. Many people worry that in letting go of the objects, they’ll be letting of what even prompts them to conjure up a memory. This allows you to preserve the sacred prompts, but in a way that takes up far less physical space.

4. Next, brainstorm some Gias – by “Gia” I don’t a puppy love per se, but special people, places or causes that truly matter to you. Or mattered to the loved one you associated with the item. Google to find charities needing donations in your area, and you'll be amazed at what you find. Ask if anyone might genuinely appreciate or find true value in the treasures.  You will likely find far more ease in reframing the act of “letting go” to “giving it a new chapter.” 

5. Finally, pass it on. Quick gut check: close your eyes, imagie holding a bright red balloon…then letting go. Now, reimagine yourself with that same red ballon, and handing it to someone you know who could use a bit of red-balloon joy in their life. Feel the difference? Passing it on and paying it forward meaningfully is the secret ingredient to letting go. Much like apple pie just plain tastes better when you share it with someone else. Magic a la mode.

Oliver turns six today. When I Facetimed with him I asked about the heart. He explained he’s waiting for his mom to mend the pocket on a special pillow, so he can tuck it in there and give it to Gia that way. While this may well simply be clever six-year-old stalling, I really do hope Oliver gives Gia his heart. I think he’ll feel like a million bucks when he does. The funny part? I can’t actually recall who originally gave the shiny token to me. But what I do know? Is that that there’s plenty more love wherever it came from.

So go on Oliver, pass it on.