12 Gentle Questions to Help You Simplify Your Stuff

After eight years of minimalism, I still use these often.

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 eight years, I’ve been simplifying 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. Maybe owning less feels better, despite all the marketing messages.

Maybe you can trust your inner sense of “enough.”

My initial decluttering snowballed into letting go of about 75% of my things. 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.”

1. Does this spark joy?

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

• Start with a single category
• Put the items in a single place
• Work with silence or nature-sounds
• Hold each item to my chest when I ask

This approach helped me notice how I truly felt about something. I felt shocked by the emotion a simple black crop top brought up. But I quickly realized that my response reflected my relationship with the person who gave it to me.

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

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

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

This approach helped early on, especially with clothes. Sometimes it felt a bit trickier with home items that fulfill a specific purpose, i.e., hobby-related things, old journals, an extra yoga mat, or meditation cushion. 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.

3. Would I repurchase this item?

This approach helps when I start 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 assessed 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. Letting go kind of sucked, but I knew having a closet full of favorites mattered more.

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

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. I didn’t like how much space they were taking up, but I also 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. I did decide to shred them; it was time.

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

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 simplify.

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, which for me made the transition a happy one.

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.

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.

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 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.

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 (periods happen), favorite books, pairs of shoes, and sweaters (I get sweaty).

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?

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.

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

11. Would a picture of this be enough?

Knowing the item is not the memory helped a lot with letting go of sentimental items. Old stuffed animals, gifts I wasn’t using, or other non-favorite memory-based things took up physical and emotional space.

You might start small with this one: take a photo of something and see how often you go back to look at the image. I never did on purpose. Instead, I’ve been enjoying more space and openness.

12. What do I hope to use this space for?

Six months ago, I moved my queen-sized bed into our guest room. Before I cleaned up, it was full of storage items. I convinced my housemates to let me use the space in exchange for the cleanup and upkeep.

What started as a wild idea turned into an at-home dance studio with space for practicing yoga, writing, and playing.

Don’t be afraid to experiment; many things are reversible. You get to create the space and lifestyle that supports your dreams.

(Bonus!) 13. What wild ideas could I try out?

My home pole dance space has been amazing, and it happened because I let myself explore “crazy” ideas. Here are a few “wins” that started as an experiment:

• Cutting my hair
• Using a bike instead of a car
• Moving to San Francisco, California
• Living in an intentional community
• Learning acro yoga
• Enjoying west coast swing dancing

Embracing minimalism opened me up to more “alternative” adventures. I started questioning my social conditioning and exploring what felt good to me. Though I’ve made many mistakes along the way, I’m learning and having fun.

Pursuing minimalism 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.

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.

Have you started simplifying yet? How’s it going? Any surprising challenges?

I write inspiring, uplifting, and empowering content on transformative topics. Join the Weekly Love News on my website to receive free newsletters each Tuesday in your inbox.