
Do you put off decluttering? I get it. Buying new stuff is generally more fun than sorting through what we already have. But decluttering is the “secret sauce” that makes organizing easier and more rewarding. And there’s one important step you shouldn’t skip: looking through everything. You may be tempted to skip this part, but there are some very good reasons not to. Let me tell you why.
The Difference Between Decluttering and Organizing
Just to be clear, decluttering and organizing are not the exactly the same thing. I think of decluttering as “step 1” in an organizing project. I recommend decluttering first because doing so typically reduces the number of items that need to be organized in the first place.
Decluttering is simply the process of sorting through existing belongings and deciding what you want to keep and what you are willing to let go of.
Organizing, or “step 2,” brings order to the items you have decided to keep. Organizing addresses things like containers, storage locations, labeling, systems, and maintenance processes.
Decluttering lightens your load and keeps you surrounded by what you use, need, and love. Organizing arranges these possessions in a manner that is reliable, predicable, and appropriately accessible.

Why We Resist Decluttering
Many people resist decluttering for several common–and very understandable–reasons.
- Decluttering involves making a lot of decisions. This takes energy and focus, which can be draining and, for some people, very difficult.
- It may require us to look at things we would rather avoid. For example, items that belonged to a loved one we are missing or papers related to a divorce or job loss.
- We worry about making bad choices. What if we get rid of something and then discover that we need it or regret letting it go?
- Decluttering often involves physical work. Items may need to be brought down from the attic, pulled out of stacks of boxes, or retrieved from hard-to-reach storage areas. For many people, this is challenging or even impossible.
- We don’t want to be wasteful and “throw everything into a landfill.” Most people would prefer to put useful belongings into the hands of someone who can use them. We also want to recycle or repurpose what’s no longer usable in an environmentally responsible way. But if we don’t have experience with these options, we may not know how to proceed.
Why We Resist Looking Through Everything
It is important to sort through everything when you declutter. That means opening every box, looking at every paper in the pile, and dumping out the small items at the bottom of a bag. I have to admit, I often get pushback on this recommendation.
Frequently, people just want to get this part of the process over with as quickly as possible. Here are some responses I frequently hear when I suggest we review in detail:
“It will take too long to look at all of this.”
“I already know what’s in there and I know I don’t want it.”
“I just don’t feel like looking at all of that.”
“There’s nothing important in there.”
“If I haven’t needed it all this time, it can’t be very important.”
“That’s not even my stuff. Can’t I just pitch it?”
“I don’t want to see what’s in that box.”
“That stack of paper scares me.”
The emotions behind these comments are valid. We may be anxious, worried, tired, overwhelmed, stressed out, or resentful. When a client wants to avoid something, I listen. We stop and talk about it. If a box or area feels too tender to tackle, we can set it aside temporarily and come back to it later.
At the same time, I remind them that I am neither intimidated nor overwhelmed by what I see. I will be there with them throughout the process. Decluttering can be a heavy task, and it is easier when you have someone to walk through it with you—especially a professional who does this work all the time.
A well-trained professional organizer will never pressure you to get rid of things. These are your belongings, and you are the one who makes the decisions. We aren’t there to judge you or second-guess you; we’re there to help you achieve your goals.
We can also help you figure out what to do with unwanted belongings. Many professional organizers have connections with complementary businesses and organizations, such as junk haulers, resellers, auction houses, local charities, recycling facilities, and upcyclers. Knowing that your items will end up in the best possible place can provide significant peace of mind.
Benefits of Looking Through Everything when Decluttering
In summary, decluttering is a way to make more room for what matters most in your life by removing the things that distracts you from it.
Successful decluttering requires that you look at everything. The phrase “getting into the weeds” comes to mind. Yes, this process may feel tedious but it’s the best way to make thoughtful decisions and avoid regrets.
When I work with clients, my first step is to unload, unbox, and unpack things so that the clients can clearly see and review what they have. It is wise to fully empty a space (e.g., a closet, drawer, shelf, box) rather than trying to review items while they are still tucked away in storage.
I also pre-sort as I go, grouping like items together, because seeing items together makes it easier to make decisions. For instance, when you realize you actually have five whisks in your kitchen, it’s easier to get rid of a couple. Or, when you realize your child drew thirty-seven pictures of rainbows this year, you can fairly easily choose the best one and recycle the rest.
Unloading a bunch of items to a sorting surface may feel a bit like jumping off a cliff because it may feel like you’ll never get it put away. Again, this is where experience helps. I know how much we can realistically tackle in a given a period of time. If you are doing this alone, you can always start small, unloading just one drawer or one shelf. Whatever you choose, take it all out.
I believe there are some concrete benefits of taking this thorough approach.
- You avoid getting rid of something important by mistake. It is very common for items to get jumbled together in a box. The box may be labeled “Old Toys,” but may, in fact, contain an old life insurance policy or piece of jewelry. The only way to be know for sure is to look through it.
- You might discover something you lost. This happens all the time. Clients will find an item that had somehow ended up in the wrong place. I frequently hear clients say, “Oh, I’ve been looking for this!” We also regularly find money.
- You may decide to keep one or two things from a grouping and get rid of the rest. Maybe you no longer want (or have room for) your full collection of nutcrackers or scarves, but perhaps there are a couple that you truly love. Sorting through the minutiae gives you the chance to make thoughtful choices.
- You will have peace of mind at the end. You won’t have to worry that maybe you tossed something you shouldn’t have or accidentally donated an important item.
* * *
Taking the time to thoroughly review your belongings is the best way to declutter without unnecessary regrets.
Have you ever been tempted to toss a box or container without looking through it first? Maybe you’ll think twice now.


I’ve learned that pre-sorting into categories is often an easier way to do decluttering. Once you see one group together easier to know what to let go of. Often you don’t know what you have because it has not been stored together.
It’s always so helpful to group like things together, right? Anything we can do to ease the process.
I’m with you 100% that decluttering is one of the first concrete steps in the organizing process. And as you said, by determining what you want to keep and letting go of unwanted, non-essential, no-longer-relevant items, organizing will be much easier. Maintaining the newly organized things will be easier, too, because you will have fewer things to care for.
It’s a win-win all around.
You mentioned pacing and decision fatigue. Those are important aspects of decluttering. Knowing how much energy someone has to focus and decide is essential. Taking breaks can help, or coming back to continue decluttering on a different day works, too.
Decluttering really does ease the entire process of getting and staying organized. Doing a thorough decluttering makes the process more successful as well.
Everyone has different goals and availabilities. It’s important to customize your approach so you can achieve your own goals in a sustainable way!
Great Post! I totally agree. We are moving and one of the things I love about moving and packing is that you get to go through everything and make decisions on what you are bringing into your new home. I know many people just want to pack up everything and deal with it later. Usually later never comes though unfortunately.
That’s so true, Kim. How many clients have I helped who had boxes that had never been unpacked from the previous move? If you can possibly do it, look BEFORE you move!
I also agree, Seana. Decluttering is a vital first step in the organizing process. One reason I advocate having short two-hour sessions with my clients is that I know decluttering involves lots of decision making and that can be tiring. Like you, I know how to monitor and manage pacing so that we go through somethings, declutter, and organize them before it’s time for me to leave. I also like the way you mention letting someone decide not to make decisions about some emotionally-laden or difficult boxes. Those, as you say, can be put aside and revisited at another time.
The goal is always to make the process as positive as possible for the client. I say in my proposals that I move at a pace that is comfortable for them.
When you do tackle an area, go ahead and look at all!
Decluttering is definitely the first step in organizing and maybe the least fun. It does require a lot of decision making. I was working with a client yesterday who unearthed a very nice-looking clock that she had bought probably 20 years ago. It was in good shape. It was one that needed winding. She didn’t like it anymore. So, easy decision, right? “But I spent $400 for it!” I am asking if she wants to try and sell it. No, she doesn’t. Finally, it went into the donation pile. But regrets over the money she spent did make it hard.
Having someone with you to talk through the process often helps.
I totally agree. Having another person nearby can make all the difference. It helps to bounce thoughts off of someone else, especially someone who isn’t judging you and who isn’t invested in getting the items out the door.
I can relate to this post. When I was doing hands-on organizing, I would hear this all the time. I would warn them that paper files need to be gone through one at a time- yes, tedious, but so valuable. Then, in that one moment, they find $800 in gift cards, a will, or an insurance policy that should have been stored in their safe; they realize the importance. Thanks for bringing this conversation to light. Many people think just throwing things away without checking them out is freeing, but is it really? What if you need to buy or find the important document later?
You’ve gotta get into the weeds!
I’ve been with clients finding those gift cards as well. Such a fun moment!!
When you talk about resistance to decluttering, you mentioned, “Decluttering involves making a lot of decisions.” So does organizing. But I think the big difference is that organizing requires decisions that are reversible. Don’t like the mugs to the left of the sink? Switch them for the cabinet on the right. But decluttering makes many people feel that they must embark on *irreversible decisions*, and that strikes fear into anyone who worries they’ll make (as you acknowledge) the wrong (or a “bad”) decision and feel pain or distress over it later.
As for all of those expressed fears you reference, I know some clients fear that it will take so much extra time to look that it will cost them more (of organizer time), but I always make the point that looking inside is the only way to guarantee you’re making wise decisions about which you can be confident. I go so far as refuse to work in situations where we DON’T look in every box or pocket before letting go of something. I still recall working with a woman whose elderly mother had gone to rehab and would not be moving back into her home. The mother assured the daughter there was no need to go through the drawers in a chest or china cabinet, but I insisted, and we found irreplaceable financial and genealogical documents. The truth is, whatever you fear lies in the to-be-downsized pile, it’s never as bad as you fear, and always better than missing a potential windfall or essential document. (And there’s almost never a scary fact buried that you didn’t really already know.)
I try to use my enthusiasm for the decluttering process, likening it to hunting for buried treasure or excavating a civilization as an archeologist, and humor about what we find, to stir up a desire to declutter. It doesn’t always create a passion for decluttering, but clients at least come to recognize the advantages.
Excellent points, as always!
Ooooh, that’s so good, Julie. Exactly. It’s that feeling of permanence that strikes fear in the soul.
And I love your point that there is almost never a scary fact buried that they didn’t know about. I can understand not wanting to “waste” money on organizer time, but after someone has worked with a PO, they start to see that we stay so focused and get so much done compared to what they could do alone that they stop pushing back.
We’ve all had those experiences like the one with your client’s mom’s place. You just have to look at everything! I’ve found jewelry in old teacups (placed there to be “safe”). This approach leads to peace of mind and wise decisions.
Much of this felt very familiar from my time as a professional organizer.
I once had the opportunity to work as part of a team on a whole home project, and the lead had to explain to one of the helpers about getting rid of unneeded items before organizing them. I was new too, and it was eye-opening for me.
Another time, I was working with a business owner in his home office, and he told me to dispose of an entire box of paperwork. I was shocked and discouraged it, but he insisted that there was nothing in there that he needed. I hope he was right!
I would have had a hard time with being told to get rid of the whole box too, Janet. I consider it “best practice” to look through it all. That gives me, and I think the client, confidence. However, if he insisted, there isn’t much you can do!