You’ve got your donate box. You’ve got your trash bag. You’re feeling good. But then… you
hit the wall. The “maybes.”
We all have them. The jeans that might fit again. The vase you could use if you ever hosted a dinner party. The book your friend swears you'll love—but you haven’t cracked it open in two years. These are the items that don’t scream “keep me” or “toss me.” They just… sit there.
Lingering.
So what do you do when you’re stuck on the fence? Here's how to stop the cycle of re-stashing your “maybe” pile—and finally move forward with
confidence.
1. Recognize that “maybe” is just code for “I’m scared to decide.” Sometimes it’s fear of regret. Sometimes it’s guilt (“Aunt Linda gave me this!”). Sometimes it’s perfectionism—we want to make the right decision. The key is acknowledging the feeling behind the hesitation. Once
you name it, it’s easier to deal with.
2. Create a “Hold Box” with a deadline. Designate a container or basket specifically for your maybe items. Label it with the date. Then set a reminder on your calendar for 30 days (or 60 if you prefer). If you haven’t reached for those items by then—or even thought about them—it’s
a clear sign they can go. No re-peeking. No reshuffling.
3. Ask better questions. Try questions that bring clarity:
“Would I buy this again
today?”
“If I moved, would I pack this?”
“Is this adding value to my life—or just taking up space?”
One great one I use myself: Would I even notice if this were gone tomorrow?
4. Use a 'One Last Use' test. Sometimes you need to give an item one more spin. Wear the sweater today. Try the kitchen gadget tonight. If it’s
uncomfortable, annoying, or not quite right, your decision just got easier. If you love it and use it, great—it moves to the keep pile.
5. Let go of guilt by reframing. Let’s say you spent good money on something—or it was a thoughtful gift. Letting it go doesn’t mean you’re wasteful or ungrateful. It means you're
clearing space for the life you're living now, not the one you might live someday. Pass it on to someone who can actually enjoy it.
6. Practice 'Maybe Today, Decided Tomorrow.' When you're exhausted from making decisions, stop. Not everything has to be decided right this second. Put your maybe items aside for today,
but schedule time tomorrow to come back with fresh eyes. Don’t let it become a forever pile—just a for now pile with a plan.
7. Celebrate the maybes you do release. Each item you move out of your home is a win. So if you finally decide to donate that knick-knack you were unsure about? Clap for yourself. You made
space—and you strengthened your decision-making muscle.
The “maybe” pile is normal. It doesn’t mean you’re failing at decluttering—it means you’re being thoughtful.
But don’t let that thoughtfulness become a trap. With a few smart systems and some honest reflection, you can clear your maybes, clear your space, and keep moving forward.
On another note...
My carefully curated list...
includes must-have travel essentials that will keep you organized, comfortable, and ready for any
adventure.
