The Best Decluttering Questions to Ask Yourself When You’re Stuck

Making decisions during the decluttering process can be really hard.

What stays?

What goes?

Will I regret getting rid of this?

Am I just tired and overwhelmed, or is this actually worth keeping?

It’s no surprise that many people freeze when faced with piles of stuff and a hundred tiny decisions. The good news? You don’t have to force your way through it—you can guide yourself with better questions.

How Better Decluttering Questions Help

When I’m working with clients, I don’t just say, “Toss that!” Instead, I ask a lot of questions. These questions help my clients pause and reflect. And the more they pause and reflect, the easier it gets to make decluttering decisions.

The goal isn’t perfection—it’s clarity and progress. These questions will move you toward that goal. And the best part? You don’t need me there to use this strategy. These same questions work just as well when you’re decluttering on your own.

Use These Questions to Declutter with More Confidence

• If this suddenly disappeared, would I even notice? Would I care? Would I replace it?

• Would I buy this again today?

• Do I love it? Like it? Use it? Need it?

• If I were moving to a new home, would I pack this?

• What is it about my future self that is more likely to use it than my present self?

• Do I feel good when I use/wear/look at this?

• How easy or inexpensive would it be to replace this later if I change my mind?

• Is it better to keep this and have it go unused, or let it go and have someone else use it?

• Which is more valuable to me—this item or the space I’d gain by letting it go?

• Would the person who gave this to me want me to feel burdened by it?

• Does this item support my current goals and values?

• If I ran into my ex, would I want to be wearing this? (Yep, this one’s silly—but weirdly effective!)

• When I imagine a clutter-free home, is this in it?

• Does this drain or increase my energy?

• Imagine someone you have a difficult relationship with has the item—would you contact them to get it back?

These questions can help cut through guilt, “what ifs,” and decision fatigue. They offer perspective when your brain is stuck in “I might need this someday” mode.

What Questions Work for You?

Everyone’s mind works a little differently, so choose what works for you here and ignore the rest. And if you’ve come up with your own helpful questions while decluttering, add them to the comments below! 👇

Happy decluttering—and don’t forget, you’ve got this. One decision at a time.