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Virginia Wells

The Art of Letting Go

How a Checklist of Questions Can Be Your Compass in Decluttering

Are you drowning in a sea of possessions, struggling to find peace in your own space? Maybe you’re not sure what questions to ask yourself as you declutter. It’s OK. You can learn the art of letting go, and declutter your life. But where do you start? The journey is broader than most portray. It’s not as simple as filling a bag with stuff and donating it to charity. If it were that simple, you wouldn’t be here reading this. 

There are many facets to decluttering successfully. One way to support your decluttering efforts is to ask yourself questions. Different people need different questions.  

The Weight of Our Possessions: 

Our possessions, once cherished, can turn into burdens if not carefully curated. As a decluttering expert, I’ve come to realise that the key to successful decluttering lies in asking the right questions. These questions serve as guiding lights, helping you navigate the emotional and practical aspects of parting with your belongings. 

The Acquiring Dilemma: 

When acquiring new items, it’s essential to pause and reflect. What purpose does this item serve? Can it truly improve your life, or is it just a fleeting desire? Did you even want it before you saw it? These are the questions that should echo in your mind as you stand in the store, faced with the temptation of a new purchase. Understanding the true value an item brings to your life is the first step towards intentional living. On the flip side, acknowledge what you might be saying goodbye to with another question. What am I saying goodbye to? Goodbye to the space the item will occupy. Goodbye to time spent cleaning it or around it, and finding a home for it. 

Whether you struggle with acquiring lots of new things, or letting them go once you have them (or both!), asking the right questions can get you on your way from breaking that decision paralysis.  

The Art of Letting Go: 

But letting go can be an emotional journey. Items hold memories and sentiments, making the decision-making process challenging. But fear not; a checklist of questions can be your compass in this sea of emotions. Does the item still add value to your life? Is it supporting the life you want to lead? These questions guide you in making choices aligned with your present and future self. 

Taming the Paperwork Beast: 

Paperwork is a common source of clutter, often lingering in drawers and shelves. But before you keep those old papers, ask yourself:  

Does it have sentimental value? (cards, letters etc). If it does, do you have to keep the paper to recall the sentiment? Can you capture the memory in some other form, and release the papers? 

How often have you referred to it in the past? If you haven’t, and you can’t see a future time you would pull it out, it’s probably safe to let it go. If this feels risky, ask yourself “If I let this go, and needed it in the future, what would I do?” You’re resourceful, you’ll come up with a solution most times! 

By delving into these questions, you’ll sift through the papers with a discerning eye, keeping only what truly matters. 

Sentimental Items: Cherish or Release? 

Sentimental items can be the most challenging to let go of. However, by asking yourself whether the item adds value and if it represents a positive feeling, you empower yourself to make decisions that resonate with your emotional well-being.  

Can you cherish the memory by writing it down in your diary, or remember it through a photo? If you must keep it – where can it be displayed to connect with that memory? If you’re not using or displaying it, is it truly worth keeping? 

Consumables: Use or Lose? 

With consumables (food, or products you use on yourself or around the house), the key is to evaluate their use and expiration date. Will you use it, or is it just contributing to the clutter? Do you use another product instead of the one you’re contemplating tossing? Would you buy it again if you needed this product right now? Are you concerned of wasting it? (I have lots of clients that readily give it to me to take and list on Buy Nothing, as they just didn’t want to waste a perfectly good product that just didn’t work for them). If this is you, can you give it to someone else who will use it, compost it or recycle it? 

By considering these questions, you make mindful choices that prevent your space from becoming storage. 

Embrace the Change with Our Decluttering Course: 

If the overwhelming task of decluttering has left you feeling stuck, unsure of where to start, or paralysed by decision fatigue, we’re here to guide you. The WellSorted Home Course is designed to empower you with a checklist of questions, expert insights, and mindful hints to make your decluttering session a success. Check out the WellSorted Home Course Here 


The art of decluttering is a journey toward a lighter, more intentional life. As you navigate the complexities of acquiring, letting go, and organising, remember that you’re not alone. The power to transform your space lies within you, and our course is here to illuminate the path. Ready to declutter with purpose? Join Virginia Wells (a Professional Organiser) in the WellSorted Home Course to get a comprehensive list of questions to ask yourself and so much more. 

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