I get stuck decluttering certain items because of guilt – pro organisers explain how to do it without the added overwhelm

Decluttering is meant to feel freeing but when guilt creeps in, it can quickly do the opposite. I know that stuck feeling well, standing in front of one of the many overstuffed cupboards in my house, fully aware that something needs to go, yet feeling bad about making that decision.

Whether it's the cost, the sentiment or the worry about waste, guilt is often the reason mess lingers in our homes, as it feels extra hard to get rid of emotional clutter.

So I asked professional organisers to share decluttering methods and checklists that minimise guilt and emotional baggage so you can have a calmer home. This is what they had to say.

How to declutter when you feel guilty about letting things go

The good news is that you don't need to be ruthless, cold-hearted or 'good' at decluttering to make progress. You just need to take a gentle approach to decluttering that works with how you're feeling.

We asked the experts for the best ways to go about it.

The most common things we feel most guilty about decluttering

According to professional organisers, guilt tends to cluster around the same categories again and again. Shannon Murphy, Professional Organiser and Founder of Simpl Living Coconcurs.

'In my experience, people don’t usually feel guilty about one specific item, but rather entire categories of items,' she explains.

Here are the most common categories that may feel particularly difficult to declutter:

• Gifts: 'Gifts often come with a sense of obligation,' explains Shannon. 'Because they were given by someone we know or care about, people feel there’s an expectation to keep them, even if they don’t really like the item or know deep down they’ll never use it. The guilt is often tied more to the relationship than the object itself.'
• Expensive purchases: 'The emotion is usually linked to money. It’s vital to remember the money was wasted at the moment of purchase, not at the point of decluttering,' explain Ingrid Jansen and Lesley Spellman from The Declutter Hub, 'No amount of time, storage, or guilt will bring that money back. Keeping items only creates ongoing costs in space, stress, maintenance and mental load.'
• Sentimental items like children's artwork, inherited belongings, photos and keepsakes all carry emotional weight, making decisions feel loaded.
• Unused items: bring a different kind of guilt, says Shannon. 'People feel bad that they didn’t use them and see them as a waste of money. Letting them go can feel like admitting a mistake, when in reality it’s simply acknowledging that our needs, tastes or circumstances have changed.' These might include clothes you have bought for a different lifestyle or hobbies you never quite started.

Shannon Murphy

Shannon Murphy is the founder of Simpl Living Co and minimalist-minded professional organiser based in West Sussex. Her mission extends beyond merely assisting individuals in decluttering, although that is an important aspect. Her overarching goal is to empower people to adopt a life free from the societal stereotype that buying more will make you happy.

The best decluttering methods if you're feeling guilty

Let's be honest, a big clear-out is not going to be realistic when you're feeling overwhelmed with guilt.

'When someone feels emotionally overwhelmed, the most important thing is to ease into the process. I always advise against starting with the hardest or most sentimental area first if you are tackling it without a professional,' explains Shannon.

Shannon recommends starting wherever feels easiest.

'This is usually a space that involves more practical decisions rather than emotional ones, things like bathroom cupboards, kitchen drawers or utility spaces.'

'Starting small builds confidence and momentum, and once that sense of achievement kicks in, people often feel far more capable of tackling the tougher areas later on.'

Ingrid and Lesley say that exploring what's driving the guilt works really well for their clients. 'Whether it’s sunk cost, a relationship, identity, fear of regret or emotional attachment, when people understand the emotional reason behind keeping something, the decision becomes rational instead of reactive, and decluttering stops feeling like loss and starts feeling like relief and clarity.'

Shannon recommends asking yourself these effective questions as you assess each item when guilt clouds your judgment:

• Did you even know you had this?
• When did you last use it?
• Are you keeping it out of guilt rather than want or need?
• What does your gut instinct say about whether you should keep it? Often, our first instinct tells us far more than overthinking ever will.

How to choose between the sentimental items you're decluttering

When everything feels sentimental, decision-making will quickly grind to a halt, and this is often where most of us might get stuck. Choosing which emotional items to let go of can feel a little impossible.

Shannon encourages her clients to think in terms of “top-tier” sentimental items. 'Ask yourself: what holds the strongest emotional connection from that time or that person? Not everything can be top-tier,' advises Shannon.

'By choosing the most meaningful pieces, you honour the memories without being weighed down by volume.'

Ingrid and Lesley concur that quality over quantity is key. 'Touch the item and work out whether it creates a genuine emotional response. One meaningful object can hold the same emotional value as 20,' they explain.

'Sentimental items exist to bring happiness and connection, but when you keep too many, that emotional impact becomes diluted, and the specialness is lost.'

However, you don't have to make these decisions all at once. It works best if you take your time. A 'maybe' box is also a good idea for those things that feel too hard to decide on. Items you're unsure about go into the box and are stored out of sight. If you don't use them after a set period, letting go feels easier.

Shannon adds that, 'the reality is that very few people are going to take everything down from their loft or storage spaces regularly to reminisce. However, if sentimental items are curated into a small collection, perhaps a couple of boxes, they’re far more likely to be revisited and enjoyed.'

Reframing decluttering so it feels less wasteful and more intentional

Let's face it, keeping something unused in a cupboard doesn't really make it more useful, as it just delays its usefulness. And Shannon says that decluttering said items feels far more intentional when they are given a clear next purpose.

'Selling items can be particularly powerful because you know the person buying them genuinely wants and will use them,' explains Shannon. 'Donating to charity is also a great option and helps reframe decluttering as something positive rather than wasteful.'

Ingrid and Lesley agree that 'Platforms like Olio, charity shops, community groups and donations give belongings a second life.'

They say decluttering then becomes redistribution, not waste. 'You’re choosing purpose and usefulness over storage and stagnation, allowing items to be used, loved and valued instead of sitting unused and forgotten in your home.'

Shannon adds that the only time she would consider decluttering wasteful is when it’s part of a cycle of mindless or habitual overbuying. 'Decluttering itself isn’t the solution to overconsumption; awareness and intention are. We have to consider our environmental impact and look at how and why we’re bringing things into our homes in the first place,' she explains.

Ingrid Jansen and Lesley Spellman, The Decluttering Hub

Ingrid Jansen and Lesley Spellman, The Declutter Hub, are the UK’s top decluttering experts, with a leading podcast (2.5M+ downloads) and a 50,000-strong Facebook community. Their new book, Reset Your Home: Unpack Your Emotions and Your Clutter, Step by Step (Bloomsbury), out February 2025, shares their proven method for emotions-based decluttering and lasting organisation.

How to let go of children's things without the guilt

I'll be honest, this is the bit of decluttering I find the hardest. As a mum, every tiny cardigan, scribbly picture or well-loved toy you should probably declutter seems to carry a memory with it, and even when an item is clearly outgrown, I still feel a flicker of guilt about being the one to decide it's time to move on.

Ingrid and Lesley explain that 'children are our most precious people, so emotions run high, but simple maths helps. You cannot keep every toy, drawing and outfit for every child you have without overwhelm.'

Shannon adds that 'children’s items often carry a similar emotional weight to sentimental possessions,' so she suggested focusing on the items that evoke the most significant memories, rather than trying to keep everything.

She advises that taking photos of certain items can be incredibly helpful; 'a photo can trigger the memory just as strongly as the physical object, without the need to store it.'

She also recommends involving children in the decision-making process where appropriate. 'This helps them develop their own decluttering skills and understand that memories don’t live in objects, they live with us,' she explains.

Ingrid and Lesley agree that decluttering teaches children a vital life skill. 'If something comes in, something leaves. This builds healthy habits, boundaries and emotional resilience around possessions from an early age.'

Storage and organising essentials

Well, there you have it. Decluttering doesn't have to be ruthless to be seriously effective.

And getting rid of some of the items that you feel guilty about will give you back much-needed space, so it's worth the extra emotional effort to sift through them.