10 Gentle Questions to Help You Declutter Your Stuff

When I first began simplifying, it was mainly out of frustration. I read minimalist blogs and realized I could create a happier relationship with my things. I could be more intentional about what I owned and only keep things that align with my well-being and desires.

Over the past ten years, I’ve been intentionally decluttering my stuff and lifestyle, making significant changes. I traded my car for a bike, moved to San Francisco, started and ended a successful tech career, took a lengthy sabbatical, and processed early traumas with shadow work.

Once you’ve found a process for letting go, you can release anything not supporting you. I’ve found (and millions of others have too) that owning less feels better, despite all the marketing messages.

My decluttering process helped me trust my inner sense of “enough.”

Initially, my decluttering snowballed into letting go of about 75% of my things. Minimalist philosophies and influencers inspired me to address my closets, wardrobe, bedroom, bathroom, and bookshelf items. At first, I felt worried about having everything I needed. But the physical, mental, and emotional space felt fantastic.

The best way to enjoy your favorite things is to only have your favorite things,— Courtney Carver, founder of “Be More with Less.”

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1. Does this spark joy?

Marie Kondo, a well-known professional organizer, made this a popular question. Using her advice, I’ve done a few things while asking this question:

• Start with a single category
• Gather items in the open to sort
• Work with silence or nature-sounds
• Hold each item to my heart as I ask the question

This approach helped me notice how I truly felt about something. I felt shocked by the emotion a simple black crop top brought up, for example. But I realized my response reflected my relationship with the person who gave it to me. That shirt did not bring joy. So I let it go.

Instead of people-pleasing, I could prioritize my needs in my space. Give yourself the gift of a joyful home.

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2. Have I used this in the last six months?

I’ve found this question listed in several minimalist blogs; it feels like addressing “low-hanging fruit.” If you’re not using something, do you really need to keep it around?

This approach helped early on, especially with clothes. Sometimes it felt trickier with home items that fulfill a specific purpose, i.e., hobby-related things, old journals, or an extra yoga mat. I kept imagining scenarios when I’d need and want these items.

Create a “pending” box when you’re not sure. You can always put the date on the box, add a reminder to your calendar for a future date, and see if you can remember what’s in it. If you can’t, it’s probably time to let it go.

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3. Would I repurchase this item?

This approach helps when I find myself making justifications for things. Sometimes getting rid of something feels like a failure. Expensive items can be even more difficult to declutter.

Last year, I re-explored my style and bought a few pricey clothing items. Later on, I noticed I wasn’t enjoying them as much, and I knew I couldn’t return them. Though letting go kind of sucked, I knew having a closet full of favorites mattered more.

Plus, donating or selling to pass the gift forward feels beautiful.

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4. Why am I holding onto this?

This question helps when you feel stuck or unsettled about something. For me, my stack of old journals felt unsettling. Though I didn’t like how much space they were taking up, I couldn’t bring myself to let them go.

Reading a few articles about others’ experiences with used journals, I realized it was more about my relationship with the past. I wanted to hold onto proof of the heartache I’d been processing and all the progress I’d made. Courtney Carver, founder of “Be More With Less,” inspired me to recycle my journals. It was time.

Recognizing the emotional link to physical items helps you make more informed choices.

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5. Am I keeping this out of guilt?

Whether it’s a sentimental item, a gift, or something expensive, guilt often plays a role. But if your guilty feelings start to outweigh the joy, it’s probably time to declutter.

In 2020, I bought a weighted keyboard for hundreds of dollars. Despite my years of private lessons, I hadn’t been playing much and wanted to get back into it. Though I did enjoy the keyboard, I stretched myself too thin with all my hobbies and felt guilty that I wasn’t playing enough.

Ultimately, I decided I’d rather have the open space than the guilt. Plus, I sold it for a great price on Facebook’s marketplace. The buyer had recently begun his piano-playing journey, making the transition a happy one.

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6. Does it support the life I want?

It’s a simple question and a great reminder. Your things are here to serve you, not the other way around.

The books we keep on display are a great example. Visible words around your house have a notable impact. If your book titles aren’t reflecting your deeper desires, maybe it’s time to let them go.

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7. How does this item make me feel?

It’s a simple question that reminds us that we deserve to feel amazing in our home space. That means letting go of anything that doesn’t feel right.

Here are a few things I used to own that I let go of:

• pretty clothes that felt stiff
• wall art I didn’t love
• a large instrument I wasn’t playing
• a floor rug I didn’t love
• gifts that didn’t bring joy

I learned that having open space felt better to me. It feels wonderful to only own my favorites. Trying to impress people with your clothes or home items never works out well anyway.

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8. How many clothes do I need?

Before my minimalism adventure, I wanted to own a different dress for every day of the year. But once I got comfortable with outfit repeating, I kept honing in on my ideal wardrobe. You really can’t mess up, as long as you have clothes to cover your body.

Whenever I need to reassess and organize my closet, I consider how many items I need for my lifestyle. Like a meal plan, I make a two-week breakdown of needs. Then, as I let go of the things I don’t need, I keep a few favorites guilt-free, even if they’re impractical. Every day, I love what I get to wear.

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9. Do I need more than one?

Sometimes yes, and sometimes no. I don’t need multiple incense holders, favorite coffee mugs, can openers, stuffed animals, overcoats, scarves, or razor brands. But, I do “need” more than one set of bed sheets, favorite books, pairs of shoes, and sweaters.

This question helped me focus on quality over quantity. For many things in your home, it’s worth experimenting with. “Just in case” usually means never. Why not pass the gift along if you’re not using it?

Also, sometimes, consider alternatives even if you do use the item. Joshua Becker, founder of Becoming Minimalist, shared an inspiring article with this decluttering tip.

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10. Replaceable in under 20 minutes for under $20?

I credit The Minimalists with this question. I’ve used it a lot, especially in group declutter sessions with my housemates. Having this accessibility perspective helped us make more confident decisions. Then, we can more easily organize what’s left.

Plus, I now enjoy a more calm and spacious, organized kitchen. What easily-replaceable items are you holding onto?

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Pursuing minimalism and organizing my life helped me let go of others’ opinions and regularly clarify what I want and need. I’ve watched myself grow more self-reliant, joyful, and creative.

As long as you’re learning, you can’t fail. By exploring “alternative” choices, I’ve gained personal insight and feel more relaxed with my lifestyle. Plus, I’ve designed a joyful home.

The best things in life are never things. Sometimes we have to clear away the clutter to remember that. We have to let go of everything we’re not before we can discover who we are.

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