4 Thoughtful Questions to Ask When Decluttering

This list of decluttering questions always helps me when I’m feeling confused or overwhelmed. If you struggle to let go, keep reading for my top four questions to ask when decluttering.

Marie Kondo famously inspired a worldwide movement with the question, “Does this spark joy?” But it’s not always that simple. Decluttering is personal and sometimes you have to approach clutter from multiple angles before you find the perspective you need.

With that in mind, here’s a list of decluttering questions I used on my own journey from shopaholic to minimalist. Store them in your ‘decluttering toolkit’ and pull them out next time you’re struggling with stubborn clutter.

"4 Thoughtful Questions to Ask When Decluttering" in a white box with a white dining table and wicker dining chairs in the background.

4 Questions That Will Help You Declutter Your Home and Life

Question 1: How does this add value to my life?

When decluttering, I like to begin by thinking about my goals.

  • What will this space look like when I’m finished decluttering?
  • What will I be doing in this space?
  • And perhaps most importantly, how do I want to feel when I’m there? 

I keep this vision in mind while working, and use it to guide my decluttering decisions. If I get stuck, I like to ask myself, “How does this item add value to my life? Does it support my vision? Or is it detracting from it?”

This mindset helps me stay focused on the big picture, which is essential while decluttering. Trust me—I know how easy it is to get lost, obsessing over tiny details, like how many coffee mugs to keep! But at the end of the day, what really matters?

Thinking about my values and vision for my home (and life!) is a reminder that my ‘stuff’ is here to serve me, not the other way around. The things I own need to earn their place or they need to go.

Remember, things don’t have to be fun to add value to your life. After all, dental doesn’t exactly bring me joy, but it does serve a clear purpose. Just make sure that value isn’t over-inflated. Sometimes we keep things ‘just in case’ for situations that may never happen.

Question 2: What’s the tradeoff and is it worth it?

When I was in university, my economics professor told me that everything in life comes with tradeoffs, and often think about this often, especially in relation to decluttering and minimalism.

Whether conscious or not, we trade time, money, and energy for the things we own. It starts with the initial cost of purchasing an item—but it doesn’t end there. 

There are also ongoing costs such as maintenance or storage, environmental costs, social costs, and even your mental health. Research has shown that clutter can have biological and neurological effects, triggering stress, anxiety and more.

In the addition, there are also opportunity costs. Every dollar (or hour) you spend on stuff is money (or time) that you could have spent on something else. This begs the question, “Is it worth it?”

It’s not always black and white. The decision to declutter is rarely about right and wrong. Instead, it’s simply two different options, with two different outcomes. You might need that sweater one day, or you might not.

You can’t tell the future, but you can acknowledge the tradeoffs and make better-informed decisions about clutter. When all the costs are clearly laid out, it becomes easier to see when it’s time to let go. 

And as an added bonus, if you create the habit of reviewing the tradeoffs before you buy something new, you cut back on mindless shopping and reduce your costs even further.

Question 3: How much do I need to be happy?

For many people, the greatest challenge to minimalist living is knowing how much is enough. What do you really need to be happy? If you can’t confidently answer this question, you’ll spend your entire life chasing an elusive idea of ‘more’, never feeling happy with what you already have

This applies to most things in life, from our careers to our closets. Collectively, we’re taught that we need to be working towards something, but to what extent?

Without a clear definition of how much is enough, we’re never satisfied. After all, you can’t win the race if there’s no finish line.

The good news is you can transform your life, breaking free from feelings of “never enough” and “I can’t keep up“, by simply setting boundaries. Sit down and make intentional decisions:

  • How many winter coats do you really need?
  • What about dinner sets?
  • Or spare towels? 

(You can take this even further by thinking about things like what does it mean to be successful, but that’s a discussion for another day.)

For now, just focus on your decluttering, and make things easier by setting rules for yourself. It might sound restrictive at first but in reality, it’s actually very liberating. Instead of going through the exhausting process of deciding what to get rid of, you’re making the much easier decision of what to keep.

An image of a minimalist dining room with a white dining table, wicker dining chairs, and a chandelier.

Question 4: Why am I struggling to let go?

Finally, my top tip for anyone struggling to declutter is to take a break for self-reflection. Cozy up with a favourite beverage, get out a pen and paper, and start the hard work of exploring your feelings. 

I know this isn’t traditional decluttering advice, but in my experience, the clutter in our homes often mirrors the clutter in our minds. An old dress, for example, can be so much more than just an “old dress”. If you feel stuck, ask yourself questions like:

  • How did you feel when you would wear that dress?
  • What did you believe about yourself?
  • What were your hopes and dreams at the time?

The things we own are often a reflection of what we believe about ourselves, which complicates things. We develop what seems like irrational attachments to physical possessions because they represent something bigger in our minds.

In this situation, you might find that you need to let go of old thoughts and beliefs before you can declutter your home and life. It’s not easy to do but at the same time, it’s a wonderful opportunity to reconnect with your true self.

The Next Step to Decluttering Your Home + Life

If these questions have inspired you to learn more about decluttering, then I invite you to take the next step. 

Subscribe using the form below and get your copy of Mindful Decluttering—my free decluttering guide and workbook— and learn how I finally decluttered my life after years of failed attempts.

You might also enjoy reading:

The Simply + Fiercely Show With Jennifer Burger

The Simply + Fiercely Show is a podcast for women who want to clear their clutter and create space for freedom and joy. If your life keeps getting bigger—but not better—then it’s time to declutter from the inside out. LISTEN NOW

What questions do you ask while decluttering? Let us know in the comments!

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9 thoughts on “4 Thoughtful Questions to Ask When Decluttering”

  1. Please tell me on what schedule you add items to this site…..I hope to get some good ideas from you!!!!
    I have started to declutter – well several false starts, but never see to get very far – plus my son messes up my email and I do not know how to retrieve what has been lost. Thanks for any information you can give me!!!!!! MAS

    Reply
  2. I have inherited/bought too many really valuable things that would be foolish to put in a yard sale or give to Goodwill. How do i get them appraised and then get rid of them responsibly?

    Reply
  3. Always thoughtful and thought-provoking, Jennifer! You are my favorite in a youtube world of minimalists because your gentle and intelligent methods and manner get to the root. Thank you for your guidance.

    Reply
  4. You are absolutely correct! Been there, done that wish I had learned this at a younger age.
    Your informal is so helpful. I am finally ready to answer the tough questions, which will save me money going forward with a plan. Thanks so very much!

    Reply

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