Decluttering: How to Decide What to Keep?

Lying before me on the floor are 3 pairs of winter boots.

Each pair is tempting me – my trendy ankle boots, my timeless black booties, and my coveted vintage riding boots. Practically I know I only need one pair … but how do I decide which one?

Maybe I should keep them all …

This was me five years ago when I was just getting started with my minimalist lifestyle. I knew my life would be better with less stuff, but I was struggling to decide what to keep and what to let go of. My decluttering attempts were slow and painful (and often complete failures) because I constantly faced overwhelming decisions and I didn’t know how to handle them.

I know from the many emails I get from readers each week that I wasn’t alone in feeling this way. The number one questions I’m asked, time and time again, is how to decide what to keep?

I’ll try and answer this today by sharing what I’ve learned about decision making – and this goes well beyond decluttering; from your closet to your career, here are a few tips to make difficult choices easier.

Do you struggle to make decluttering decisions? From your closet to your career, here are my tips for making decisions about what stays and what goes.


The first and most important thing I do when I’m a facing a difficult decision is to pause and step back from the situation. This is because when we’re facing difficult decisions (about anything – not just clutter) it’s easy to get lost in our thoughts and to lose sight of the big picture.

For example, when decluttering I’ve often struggled with:

  • guilt about past mistakes (ahem … like spending $200 on a dress I’ve never worn!)
  • self acceptance (accepting I’m beautiful because of who I am and not because of my 100 pairs of shoes.)
  • external obligations (feeling obliged to keep or do things because I don’t want to let anyone down.)
  • deep emotions (letting strong memories overwhelm me and cloud my judgement.)

These feelings often make it difficult to think rationally and can turn simple decisions into difficult ones! (After all, deciding to clean out our closets or say goodbye to our junk drawers should be easy … in theory.)

Pausing and taking a moment to remove ourselves from the situation creates space to make rational decisions and to think about the big picture.


Speaking of the big picture, one of the most powerful things I’ve learned to do is use boundaries to help me make decisions.

Let’s look at my wardrobe for example. Five years ago, I decided to embrace minimalism and my closet was my first challenge – and what a challenge it was! I was using my entire second bedroom to store my huge collection of shoes, handbags and clothes. Decluttering my closet felt like an impossible task – and at first, it was.

I made several attempts and failed over and over again – until I decided to change my approach.

Instead of haphazardly making decisions as I went, I decided to step back and decide what I wanted most for my wardrobe. I looked at the items I loved and wore most often for inspiration and I took note of patterns: I loved neutral colours, I preferred a skinny silhouette, and I always chose to wear comfortable and low maintenance pieces.

Using this information I decided ahead of time what things I would no longer keep, including:

  • maxi skirts, flared jeans, or anything voluminous on the bottom.
  • anything white or dry-clean only (I’m not good at laundry!)
  • bright colours (I feel more ‘me’ in neutrals)

[Click here for the full details on how I simplified my wardrobe.]

What I was did was create a vision for my wardrobe and then use this vision to define boundaries.

Doing this took the stress and emotion out of decision making, and it also helped with decision fatigue (the overwhelm we feel when faced with too many choices!)

This simple system can be applied to so many areas of your life.

  • If you’re decluttering your bedroom, decide the purpose of your space and then define what belongs.
  • If you’re decluttering your schedule, ask what you want to get done and then define your priorities.
  • If you’re thinking of changing careers, ask why you work and what you want to achieve, then define your search criteria.

With any decision, focusing on your vision and using it to define boundaries can help you make better choices.

If you’d like to learn more about setting boundaries, then I invite you to get your free copy of Mindful Decluttering by subscribing below. In Mindful Decluttering, I share step-by-step how I decluttered my home and life. (It also includes practical advice, personal stories, and a troubleshooting guide to help you overcome your decluttering challenges!)


Even with your big picture in mind and clearly defined boundaries, you might still struggle to make decluttering decisions. When this happens, it’s often because there’s a fear that needs to be acknowledged and addressed.

Usually, this fear manifests itself as a general fear of ‘making the wrong decision’, but if we dig deeper we can usually get more specific:

  • I’m afraid to get rid of my black jacket because I might need it to put together an outfit.
  • I’m afraid to get rid of my extra dinner plates because I might have company over.
  • I’m afraid to quit my job because it might mean I can’t get another one later.

From the trivial to the important, specifically acknowledging your fear will help you make a better decision. Now that you know what’s holding you back you can address it.

Consider the worst case scenario.
Then the best case scenario.
Then the likelihood of each scenario happening.

Armed with this information, we’re better equipped to face our fears and make a decision. After all, acknowledging the worst case scenario might be borrowing a dining set from your neighbour might give you the perspective you need to move forward.


Finally, when faced with a tough decision, sometimes we need to accept isn’t a clear right or wrong answer. You might not be able to predict how many saucepans you’ll need in the future, or if you’ll regret saying goodbye to your high school yearbooks, or if two sets of pillowcases are really enough.

But this isn’t a bad thing; instead, it’s an amazing opportunity. When there is no ‘best’ decision, we’re given an amazing opportunity to redefine ourselves.

As the philosopher Ruth Chang tells us in her TED Talk:

When we create reasons for ourselves to become this kind of person rather than that, we wholeheartedly become the people that we are. You might say that we become the authors of our own lives.

To me, this means that when decluttering (or making any difficult decision), we have the opportunity to redefine who we are. Instead of worrying which pair of boots to keep, we can decide to be someone who throws any pair of shoes on her feet on the way to new and exciting adventures.

What are your top decluttering tips? Or what are your biggest challenges when making decisions about clutter? Let me know in the comments! xo

Photo credit: Me!

Author: Jennifer

Hello there! I'm Jennifer and welcome to Simply + Fiercely, a community of people striving to live simpler, more intentional lives. As a former shopaholic and workaholic, I know how it feels to live a life that doesn't feel true to what's in your heart. Fortunately, I've transformed my life and gone from feeling cluttered and confused to living a curated life filled with purpose and joy. Now I'm here to help you do the same. 👉🏻 Click here to get started!