5 Stress-Free Tips to Help You Decide What to Keep When Decluttering

Knowing what to keep and toss when you're decluttering can be hard, but recognizing a few things about the process can help. If we can do it, so you can you.

Published October 26, 2023
person decluttering

What do four kids, 17 years, and a five-bedroom house add up to? Lots of laughter, lots of love, and lots of memories — but also lots of stuff. When my family moved to a much smaller place, that meant asking the big question of how to decide what to keep when decluttering and sorting. 

You don't have to be moving or have kids in order to want to declutter your space and have a little more peace in your home. These tips and questions to ask yourself might help you figure out what to keep and what to toss as you're starting the decluttering process. 

1. Know That Decluttering Is a Mental and Physical Process

Decluttering is both a mental and physical process, but the mental part is what can often become the most challenging. All of our" stuff" can be intricately tied to our experiences, our memories, and even sometimes people in our lives — and that can make the decision to toss or donate items pretty tough. Finding the motivation to declutter might start with just recognizing that this really is a mental process and there's no "perfect" way to do it. 

I love organized spaces, and I don't consider myself an overly sentimental person when it comes to stuff, but even for the most organized or least sentimental person, decluttering can be hard. Although I've decluttered for years (four kids, after all), it was helpful during this most recent round to recognize that there can still be emotions tied to some of our things — and that's okay. You might even want to let certain items go and still grieve them (or more accurately, the connection or memory or relationship they are tied to) a little bit, and that's also totally okay. 

2. Ask Yourself Some Key Questions to Decide What to Declutter

These six questions helped me as I navigated some of the items my family had accumulated. Whether you're organizing your closet, kitchen, or living room, asking yourself these things might help you sort through your own stuff and decide what to keep as you declutter. 

person sorting papers

Is the Item in Usable Condition (or Can You Repurpose It)?

If it's not usable, it can be good to relegate it to the toss pile. But if you can see a good way to repurpose it, it can be worth keeping. An example was a picnic basket my grandma had given me. The latches were broken, and it wasn't usable for its intended purpose any longer, but it actually made a really cute little storage basket for my perfumes and lotions. 

Does This Item Fit My Life Now? 

This question can be especially helpful if you're struggling with how to declutter when you want to keep everything. Many of the items we hold on to are actually items from previous seasons in our lives and don't really work for where we're at now.

This can apply to anything from clothing to workout equipment to kitchen gadgets to a host of other things. If this is an item that was previously useful to you, but you don't really visualize a good way to use it in your life now, you might want to let it go. 

Quick Tip

As you're decluttering, keep items that fit your life now, or match who you are trying to become, not necessarily who you were in the past. 

How Does This Item Make Me Feel? 

Whether it's a spatula or a sweater, there could be very good reasons why a particular item might make you feel a certain way. You don't even have to go deep into why it makes you feel that way. If it doesn't make you feel good when you look at it, it's a really good candidate to toss or donate, even if it's in great condition. 

What Kind of Memories Does This Item Hold?

Sometimes otherwise good and useful items can have memories that aren't great. Give yourself permission to say goodbye to those things. Alternatively, maybe there are items that aren't all that useful, but they really do harbor good memories and make you feel good when you look at them. During the decluttering process, you'll make space for those pieces that make you feel good and hold good memories. 

Quick Tip

Sometimes, you have a lot of special things that have good memories. If you're struggling with decluttering sentimental items, think about keeping a few of the most meaningful (a special sweater your child wore, but not 30 of their baby outfits, for example). 

Am I Keeping This Item Out of Guilt or a Sense of Obligation? 

For all of us who have a little people-pleasing inside of us, this can be really hard. Whether the item was given as a gift or even as a hand-me-down, you might worry that the person will be upset that you aren't using their gift or the thing they passed on to you. Try to let go of that guilt. If the person who gave it to you really loves you, they want you to be happy, and they'll probably understand if you give the item away when it's not useful in your life. 

If you decide to keep certain items and bring them out when those particular people visit, that's okay, too. Maybe as you're decluttering, you're able to clear out part of a cabinet or closet and make a space for those types of things. Do what works for you and your life. 

Does Holding On to This Item Make My Life Easier or Harder? 

If it doesn't benefit your life, it might be time to let it go. If it's another thing to pick up, organize, or find space for in your drawers or cupboards that won't make your life easier, it might be better off in the toss or donate pile. Decluttering key places can make your life a little happier and easier.     

Quick Tip

 If you're looking for decluttering inspiration, it can be really helpful to look at decluttering less as having to let go and get rid of things and more as making space for what matters in your life now. 

3. Consider Decluttering by Rooms, Zones, or Spaces

Trying to tackle too much at one time and deciding what to keep can feel overwhelming, so it can be helpful to pick something specific to focus on rather than clearing out multiple spaces at once. As you're organizing spaces to keep clutter under control, think about starting with a room, a space in a room, or even one specific thing. If your office is causing you stress, you can start with your desk or even a single desk drawer. If your kitchen feels chaotic, you can start with one cabinet or one counter. 

While it can be beneficial not to tackle too much, sometimes spaces can complement one another and you can work on them as zones — an entryway and coat closet can go together, for example, or you might want to work in tandem on two kids' rooms to sort through clothing and toys. 

4. Set Aside Time to Declutter When You're in a Good Mental Space

person boxing items

The increments of time will depend on what works best for you, but setting aside some sort of timeframe for decluttering can help you make progress and build momentum to get it done. When your schedule is packed, it might be 15 minutes a day. If you have a few hours on the weekend, you can use that to start making a dent in the decluttering process. Consistent progress will yield results and help to give you the motivation to continue. 

But what's also key here is that when you choose the times you try to do it, that you're in a pretty good mental space. If you're frazzled, exhausted, hungry, or tired, it's just going to make the decision of what stays and what goes that much more frustrating. 

Quick Tip

Do things that help make the decluttering process more enjoyable. Put on music you love, put your favorite tea or coffee in a to-go mug to sip on while you work, or even light a candle in your favorite scent in the room where you'll be working.

5. Designate Keep, Toss, and Donate Bins (But You Might Need a Maybe Pile)

Lots of organizational systems recommend having bins, boxes, or bags that you can designate as keep, toss, and donate piles. While I wholeheartedly agree, some of us may also need a "maybe" pile. 

"Maybe" piles can be for things like items that belong to the family as a whole, or that belong to another family member, so you need their input on it. They can also be for things that you like but aren't sure you have the space for. As you continue decluttering and sorting, you may end up putting some items definitively into the toss or donate pile, and that will open up the space for that item.

Giving yourself permission to have a "maybe" pile can ease some of the tension or let you move on rather than getting stuck when you can't talk to a family member about the item right then. Remember, this is your process — you don't have to beat yourself up if it takes you more than one decluttering session to decide. 

Need to Know

One caveat for those of us who can overthink — it can be really good to just make that hard decision to let things go, so use that "maybe" pile cautiously. The more you put in that pile, the longer it can take. So if you want to declutter fast, try as often as you can to make a solid decision for the keep, toss, or donate bins. 

Find What Works for You in the Decluttering Process

I wouldn't exactly label myself a minimalist, but a drawer with some excess space and shirts folded neatly in thirds (my own adaption of Marie Kondo's file folding method) gives me a special kind of joy. As long as we're alive, we're going to have to deal with stuff, and that also means a lifelong journey of decluttering. But by asking ourselves some important questions in deciding what to keep and what to let go of, the process can be a little easier, and we can embrace the peace and joy that decluttering brings.        

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5 Stress-Free Tips to Help You Decide What to Keep When Decluttering