Ep. 256: Why You Can't Declutter Certain Things (And It Has Nothing To Do With Organization)

As I do so often…I want to start with a question today.

Have you ever picked something up…something you've picked up a hundred times before and immediately thought: I should probably get rid of this.

And then put it right back where you found it?

Maybe you've done that a few times.

Maybe you've done it every single time you've opened that same closet for the last five years.

Maybe it's a box in the basement that's been there so long you've stopped seeing it. Except you haven't really stopped seeing it, because every time you walk past it, something in your chest goes tight.

Maybe it's baby clothes.

Maybe it's your mom's dishes.

Maybe it's a box of craft supplies from that hobby you were absolutely going to start.

Maybe it's paperwork from a job you left, or files from a business idea that never got off the ground, or equipment from a season of life that ended and you're not sure how you feel about that.

Whatever it is, every time you see it, the conversation starts.

"I need to deal with this."

"I should make a decision."

"Why haven't I handled this yet?"

And then nothing happens.

The item stays.

The guilt stays.

The low-level mental noise stays.

And you start to make it mean something about yourself.

Maybe you're too sentimental.

Maybe you're just disorganized.

Maybe you're indecisive.

Maybe you're the kind of person who can never finish what they start.

And here's what I want to say to you before we go any further.

None of those things are true.

The reason you can't make a decision about certain items has absolutely nothing to do with organization.

And once you understand what's really going on, everything changes.

That's what today's episode is about.

Let's get into it.

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Transcript

Well, hey, welcome to our clutter conversation today. So we have these clutter conversations every Tuesday, but the clutter we talk about is way more than just stuff. We talk about things like emotional clutter, invisible clutter, mental clutter, identity clutter, things you never even knew were clutter. We talk about it all here. And hey, I'm Jennifer Roskamp, and I am your host, and I'm a certified strategist and life coach.

And I'm so glad you're here. And if you are not new here, you can probably hear there's a whole lot of sickness going on today. But you know what? Here we are. We're all about being real here, having the hard conversations. Yeah, I am fighting a cold from Bolivia of all places because my daughter was in Bolivia and she brought this thing home. So here we are getting through it. But if you're new to my conversations here, the conversations that I have are for midlife women who are.

essentially done feeling stuck, done surviving on fumes, and ready to actually lead their own lives, not just manage them. We talk about real stuff here. There is no toxic positivity. There is no surface level fixes. There is just honest conversations and practical tools that actually work in real life. And again, if you've been around for a while, you know that this is a space where I don't pull punches.

I call it like I see it. And today I'm gonna call out something that I think most decluttering advice completely misses. Because I don't think clutter is actually about clutter. I think it's almost always about something deeper. And when we treat the stuff like the problem, we miss the whole point. We spin our wheels, we feel worse about ourselves, and the clutter doesn't actually go anywhere.

And so today we're talking about emotional attachment, what it is, why it shows up in our stuff, and what it actually costs you when you leave it unaddressed. And at the end, I'm gonna tell you about a workshop that I created that goes much deeper into all of this because I wanna give you a real path forward, not just something to think about. So let's jump in. Well

I wanna start with something personal first because I think it will set up everything that I'm about to teach you. A few years ago I was going through a particularly hard season.

My kids were getting older and the house felt like it needed a refresh. And I decided I was going to do a serious declutter of the basement. I had all the energy. I had the bags. I was ready. And then I opened one specific bin. It was full of things from when all of my kids were little. There were little league trophies, there were drawings, there was a pair of shoes that one of my kids wore when they learned to walk. There was some artwork from

Preschool stuff we had done. There was a birthday banner that I had made for one of their parties. None of the things in that bin were trash. But realistically, I didn't need it. I knew that. And so I stood there for probably 10 minutes and I was picking up things and I was putting them down. And I was feeling this weird mixture of grief and guilt and love in something that I couldn't even name. And then I closed the bin and I walked away. I felt embarrassed.

After all, I coach women on moving forward, on making decisions, on not staying stuck. And I could not make a simple decision about a bin full of stuff. Except, here's what I realized later. None of these things, they were not a simple decision. It never was a simple decision with any of this stuff. That bin wasn't just a bin, it was a whole chapter of my life that I wasn't sure I was ready to close.

It was the years when my kids needed me in a very specific way. A way they don't need me anymore. It was the version of myself that was a young mom, figuring it all out, running herself ragged and loving every single second of it. The metals, they weren't just medals, they were memories. The shoes, they weren't just shoes. They were evidence that a season of my life, it mattered so much. And it happened. It happened.

And when I understood all of that stuff, I stopped beating myself up for not being able to just make a decision. Because what I was actually navigating, it wasn't clutter, it was attachment. And those are completely different things. So here's the core thing I want you to take away from this conversation. The item that you're struggling to get rid of, it isn't difficult because of what it is. It's difficult because of what it represents.

That's a completely different problem and it requires a completely different approach. Think about it this way: an expired coupon, it doesn't feel heavy. You toss it without thinking. A broken phone charger, that's gone. There is not a second thought about it. A random coffee mug that you got at a conference five years ago? Easy. It just goes in the donate pile. But your kids' baby clothes? Well, now that's different. Your mother's dishes.

Even the ones you don't use, even the ones you don't really like, that's different. The box of supplies from the hobby that you were gonna start when you finally had time for yourself, the thing that you bought when you were trying to do something just for you, that's different. The difference isn't the object, the difference is the meaning attached to the object. Baby clothes represent a season of life. Your mother's dishes represent a relationship.

Maybe one that's changed, maybe one that ended, maybe one that was complicated. The under what about the the hobby that you never started? That hobby represents a version of yourself that you had hoped to become. It was a possibility. It was a dream that you put on hold to focus on other things. And when you now sit here and you try to make a decision about that stuff, using the same logic.

That you would use for an expired coupon. Do I use it? Do I need it? When was the last time I touched it? Well, you are applying the wrong tool to the problem. It's like trying to fix an emotional wound with a band-aid. The band-aid isn't wrong, it's just not reaching the right place. And that's exactly why the item stays year after year. The conversation, it loops, the guilt, it builds.

And you walk away feeling worse about yourself than you did before. The truth is, you're not indecisive. You're not disorganized. You're not bad at decluttering. You're trying to make a decision that isn't really about the object. And until you understand what it's actually about, you're gonna keep hitting the same wall. Now, I wanna break this down a little because emotional attachment, that's what we're talking about.

And emotional attachment to stuff isn't all the same. It shows up in different ways. And recognizing which one you're dealing with helps you understand what's really going on underneath. So the first kind of emotional attachment, let's call it a certain kind of grief. It's attachment. It's grief attachment. This is when an item is connected to a loss, the loss of a person, the loss of a season, the loss of a version of yourself or a life.

That no longer exists. Baby clothes, they often fall here. So do items that belong to people who have passed away. Items from a marriage that ended, items from a career that you walked away from, items from a home that you grew up in. Grief attachment doesn't mean that you're stuck in the past or that something is wrong with you. It means that the item is carrying the weight of something real that happened.

Something that mattered, and your nervous system, it knows it. So the second kind is identity attachment. This is when the item represents who you were or who you thought you were going to be. The guitar that you bought, when you were gonna finally learn, the running gear that you bought, when you were gonna finally get healthy, the art supplies, the sewing machine, the journal with three entries in it.

These items can feel especially loaded because they're not just about a past season. They're about a version of yourself that you wanted to become and maybe still want to become, and maybe aren't sure that you'll ever actually become at all. So I want to sit with this one for a second because I think it hits a lot of midlife women, particularly hard. See, in midlife, there's this really uncomfortable collision between.

Who you thought you'd be by now and who you actually are. And for a lot of women, the stuff in the closet becomes a physical representation of that gap. The sewing machine isn't just a sewing machine, it's the creative woman that you are gonna become once the kids were older. The exercise equipment, it's not just equipment, it's the version of you who is finally gonna prioritize her health. The stack of books that you haven't read, that stack is not just books.

It's the curious intellectual woman that you've always wanted to make space for, but never really had the time or the energy or the bandwidth or the capacity. And so letting go of these items can feel like admitting that version of you, it's not coming. And that's a kind of grief all on its own. It's this quiet, complicated grief that we don't talk about enough. And so instead of dealing with that grief, you keep the item.

Not because you're going to use it, but because keeping it means the possibility, well, it's still alive. I'm not saying that that's wrong. I'm saying that it's worth understanding. Because sometimes the possibility is genuinely still alive. And the item serves as a real reminder of something that you still want to pursue. But here's the thing: sometimes the item is just a way of avoiding the harder question. And the question is this: what do I actually want now?

Not who I thought I'd be, not who I used to be, but who do I want to be in this season with this life, with the energy and time and bandwidth and capacity that I actually have? Now that's a question that's worth asking. And the stuff in the closet will keep drowning it out until you finally ask it. So the third kind is guilt attachment. This is when you feel like getting rid of something, but

you feel like doing so would mean something bad about you. You can't donate the treadmill because then you're officially the person who wasted money on a treadmill. You can't let go of the sentimental gifts because then well then you're ungrateful. You can't clear out you you're you can't you can't clear out, boy, that was rough. You can't clear out your kid's artwork because then you're the mom who doesn't value her kid's creativity. Grief attachment, it's sneaky.

Because it disguises itself as either love or responsibility quite often. But what it's really doing is using the item as a way to manage your self-image. And as long as you keep it, you haven't officially confirmed the thing you're afraid is true about yourself. And the fourth kind of attachment is hope attachment. This is the someday stuff, the clothes you're hanging on to for when you lose the weight, the equipment.


That you're keeping for when life slows down. The supplies you're keeping for when you have more time or more energy or more capacity. Now, hope attachment, it isn't bad. Having hope isn't bad. But when the stuff becomes a substitute for actually addressing what's in the way of the someday, well, it becomes one more thing quietly draining your energy. Most of us have items that fall into more than one of these categories at once.

And that's exactly why decluttering feels so hard. You're not sorting objects. You're sorting identity and grief and guilt and hope all at the same time. Now I want to talk about the real cost of leaving all of this unaddressed because I think a lot of women minimize the power that is here. A lot of women think it's just stuff, it's just a bin in the basement. It's not a big deal.

But here's what I know after years of working with women on this very thing. The decision never goes away. Every time you walk past it, your brain registers it. Every time you open the closet, the internal conversation, it starts up again. Every time you think about organizing your space, those unfinished decisions, well, they rise to the surface.

And the cumulative weight of hundreds of unfinished decisions, maybe even thousands by this time, across every room and every closet, every bin, every drawer is absolutely exhausting. It's not physical clutter that you're carrying, it's mental clutter. And mental clutter is one of the biggest contributors to the kind of low-grade overwhelm that midlife women tell me they are feeling every single day. I hear this every single day.

The kind of overwhelm that makes it hard to focus, the kind that makes the deal feel heavy before it even starts. The kind that makes you feel behind even when you're technically keeping up. You walk into your home and instead of feeling peace, you feel the weight of everything that's unresolved. And it's not just the stuff, it's the unfinished decisions pile up in the other areas, too. It's the relationships that you haven't addressed.

It's the conversations that you keep putting off. It's the choices that you know you need to make, but you keep avoiding them. Emotional clutter and physical clutter, they feed each other. When your outer space is cluttered with things that you haven't processed emotionally, it's very hard to think clearly. And when you can't think clearly, it's even harder to make decisions. And so it makes total sense that the pile is.

Growing and that the overwhelm grows with it. And here's the other thing that I want to call out here. Women often tell me that they feel shame about their clutter, real shame, like having a messy or cluttered space. It means that something is fundamentally wrong with them. And I want to be clear: the clutter is not a character flaw, it is a symptom. It's telling you that there's something underneath that hasn't been processed.

There's a decision that needs clarity. There's a feeling that needs to be acknowledged. There's a season that needs to be grieved or released or honored. But we don't talk about it that way. Most decluttering advice treats it like a logistics problem. You just need more bins or better labels or a different system. And you try those things and they help, maybe temporarily, but then the clutter it comes back because the root of the problem.

was never addressed. You are not a disorganized person. You are a person who is carrying more emotional weight than most decluttering advice is equipped to help you with. And that changes the approach entirely. So let's talk about why the standard decluttering advice it doesn't work. Now, again, I want to spend a few minutes on this because I think it's important.

Most decluttering advice is built on a very logical framework. Things like do you use it? Do you love it? Does it spark joy? Have you touched it in the last year? And I'm not saying that those questions are wrong. Hear me clearly. For practical stuff, those work fine, but they fail, they fail and they fall completely flat when emotions are wrapped up in the mix.

Because here's what's here's what's happening. When you're standing in front of something that carries emotional weight and you ask yourself, do I love it? Well, the answer, it's complicated. Do you love the item? Well, not necessarily. Do you love what it represents? Probably. Are you afraid of what it means to not love it anymore? Well, possibly.

Can you even access what you actually feel in this moment because there's so much layered on top of it? Probably not. And when you can't answer the question clearly, you just default to keeping the item because keeping it, it feels safer. And with all of that going on, it is safer. Keeping it avoids the grief. Keeping it doesn't require you to make a decision that feels permanent. And so you walk away again.

With the guilt still in place and the item still in place and the mental loop still running. Smart women who make confident decisions at work, they freeze in front of a box in the basement because the decision that they're trying to make isn't really about the box. It's about what's inside the box grief, identity, fear, hope. You cannot logic your way through these things. You need a different kind of tool.

Which is exactly why I built what I built. And I'll tell you about that in just a minute. But first, I want to give you something practical. So before you try to make any decision about a difficult item, I want you to try something. It uses one of my favorite words, curious. So here's what I want you to do: get curious, not judgmental, not pressured, not trying to force yourself into a conclusion. Just curious. Here's how it works.

The next time you pick up an item and you feel that familiar pull, the one that tells you that this is harder than it should be, instead of asking, should I keep this or get rid of it? Ask these three questions. Question number one What does this item represent to me? Not what is it, but what does it mean? What season does it carry? What person does it remind you of? What version of yourself?

Is it connected to? Just honestly answer that. Don't try to solve anything yet. Just notice what comes up. Question number two: What emotion am I trying to avoid by keeping this? Now, this is the harder one, but it is the most important one. Are you avoiding grief? If you let it go, does it mean that the season is really over? Are you avoiding guilt?

If you let it go, does it confirm something that you're afraid is true about yourself? Are you avoiding fear? If you let it go, are you closing a door that you're not ready to close? Just name it. You don't have to do anything about it right now or anything with it right now. You just have to name it. And question number three: What would it feel like to make peace with this? Not necessarily let it go, but make peace with it. Because here's what I've learned.

Sometimes making peace means letting it go. And sometimes making peace means keeping it intentionally with full awareness of what it represents and why it matters to you, and doing so without the guilt. Both are valid. Friend, the goal is not just to empty the bin, the goal is to make the decision from clarity instead of avoidance.

And I want to say something else here too, because I think that this needs to be said. You are allowed to keep things. You are allowed to keep your mother's dishes, even if you never use them. You are allowed to keep the baby shoes, even if your kids are teenagers now. You are allowed to keep the things that bring you comfort or connection or joy, even if it doesn't make sense by some external standard of practicality. The problem isn't keeping.

Things. The problem is keeping things on autopilot without ever actually choosing to keep the item, without ever examining what they mean or what they're there for, or what what what keeping them is doing to your mental and emotional space. There's a massive difference between saying, I'm keeping this because I've chosen to, because it matters to me, because I've thought about it and this is what I want, and saying,

I'm keeping this because I can't make a decision about it. And every time I try, I feel terrible. And so I'm just going to close the lid and walk away. One of those choices is intentional, and one of them is avoidance. And the thing about avoidance is that it always has a cost. Every decision you leave unfinished is a small drain on your capacity. Now multiply that by

Dozens of unfinished decisions sitting in closets and basements and bins and drawers all over your house. Now suddenly we don't have a small thing. There's a significant portion of your mental and emotional energy quietly leaking out of every single day with these things. Clarity. It doesn't come from thinking more about it. Clarity comes from understanding what's actually underneath.

And then moving forward from there.

So here's where we are. You now understand that clutter isn't just a logistics problem, it could very well be an emotional one. You understand that the items you can't seem to let go of are carrying meaning, grief, identity, guilt, hope, and that no amount of bin-buying or organizational systems will fix that. You understand that the unfinished decisions are costing you real energy, real mental space.

Real capacity. And you've got a starting point, the three questions. A place to begin getting curious instead of judgmental. But I also want to be honest with you. Understanding that emotional attachment exists in one thing. It exists in your understanding, but that's only one thing. Now, knowing how to actually work through it, to move from awareness to action.

To make decisions from clarity instead of guilt or fear, that's a whole different thing. And awareness without action keeps you stuck just as surely as not knowing anything at all. So I want to invite you into something. I'm going deeper in everything that we talked about today in a workshop called Break Free from Emotional Attachment to Your Stuff. And it's designed to take you well beyond this conversation we're having here today.

Inside this workshop, we're going much deeper. We're gonna look at specific types of emotional attachment, the ones that I introduced today, and we're gonna work through how to identify which one is at play for you and why. We'll explore the real reasons that certain items feel impossible to release, not the surface level reasons that you've been telling yourself, the actual reasons. We'll do work around grief, the identity questions.

The guilt spirals that keep you locked in indecision. And I'm going to walk you through a process, a real practical process for moving from stuck to clear. Not cleared out, not perfectly organized, but clear. On what you actually want your space to feel like. Clear on what you're actually holding on to and why. Clear on what you're ready to release and what you're choosing to keep.

On purpose with intention and without guilt. This is not a workshop about bins and systems and labels. This is a clutter workshop about understanding yourself well enough to make decisions that actually stick. Because when you understand the attachment, the decisions get easier, not painless, not overnight, but clearer. And clarity is where momentum begins.

Now, if you've been carrying the same unfinished decisions for years and you're finally ready to understand what's actually going on underneath all of them, I would love to have you in the room for this workshop. Visit midlifeclutterhelp.com for the details you need on how you can join us. Now, I want to give you four takeaways for today to make sure that you have really fully embraced everything we've talked about. Takeaway number one.

The clutter isn't the problem. The unresolved meaning is. Most decluttering advice treats it, treats the clutter as a logistics issue. But when you can't seem to let something go, it's almost never about the object. It's about what the object represents: a season, a relationship, a version of yourself. Treating it like an organization problem will keep you stuck. Takeaway number two.

There are four kinds of emotional attachment and recognizing yours changes everything. We've got grief attachment, identity attachment, guilt attachment, and hope attachment. And each show up differently and each require a different kind of honesty. The first step isn't making a decision, it's understanding which kind of weight and which kind of attachment you're actually carrying.

Takeaway number three, unfinished decisions are costing you more than you think. Every item you've avoided, every item that you have avoided making a decision about is a small but steady drain on your mental and emotional energy. Across an entire house full of those unfinished loops, well, that's going to add up to a significant portion of your capacity.

Capacity that you need for other areas in your life. Addressing the attachment isn't just about the stuff. It's about getting your energy back. The fourth takeaway is to get curious before you get decisive. Instead of forcing a decision that you're not ready to make about an item, ask, what does this item represent? What emotion am I avoiding by keeping it? What would it feel like to make peace with this?

Curiosity creates clarity. And clarity is where is where real momentum begins. So before I I let you go, I want to leave you with this. The meaning and the object are not the same thing. I'm gonna say that again. The meaning and the object are not the same thing. That old tote in the basement, the one that you've been walking past for years, it's not full of clutter.

It's full of chapters. It's full of seasons. It's full of a different time in your life. And you are not required to make a snap decision about any of it. But you are allowed to get curious. You are allowed to ask what's really happening underneath the avoidance. You are allowed to stop making this mean something negative about who you are because here's the truth. The fact that you

Feel deeply connected to the things that have mattered to you is not a character flaw. It's evidence that you are a person who lives and loves with her whole self. The work isn't about becoming someone who can throw things away without feeling anything. The work is about learning to sit with the feeling long enough to move through it and then decide what to do from a place of clarity instead of guilt.

You can do that not perfectly, not all at once, but one item at a time, one honest question at a time. That's how the mental clutter starts to lift. That's how the weight starts to ease. That's how you start to feel at home in your own home again. Make sure to check the notes down below for how you can join us for this workshop. This is one that you are not going to want to miss.

And so until next time, friend, keep showing up. Keep asking good questions. And remember, you can always start again at any moment. Until we talk again, lead yourself well.