Ep. 252: Why Decluttering Feels So Hard (And Why Forcing Yourself Through It Isn't Working

I want you to do something with me right now.

Close your eyes for a second. Actually, don't close your eyes, you're probably driving or folding laundry. But picture this.

Imagine every single item in your home got dumped into one giant pile.

Everything.

The expired coupons shoved in the junk drawer.

The junk mail you keep meaning to deal with.

The stained kitchen towels you're not sure why you're still keeping.

The tangle of broken charger cords that you have no idea what they even go to anymore.

Your grandmother's wedding ring.

Your child's first baby blanket.

Now imagine I looked at you and said: every single item in that pile is equally difficult to deal with. Every decision requires the same emotional energy. Every object deserves the same amount of your time and attention.

You'd look at me like I had lost my mind.

Because that's ridiculous.

Of course it isn't.

But here's the thing…that's exactly how most women walk into a room when they're trying to declutter.

If you’ve got any amount of clutter, this is a conversation you’ll want to listen to. 

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Transcript

Well, okay, so here's what often happens when you're faced with boxes and bins and piles. Your brain makes a split second decision that everything in the bin or in the box or in the room or in the pile is going to be hard. Everything is gonna be emotional. Every item is going to require deep thought and long deliberation and probably some tears. And so before you have touched a single thing.

Before you have moved one item, made one decision, filled one bag, you are already exhausted, already overwhelmed, already defeated. Does this sound familiar? This is gonna be what we're talking about today. Why decluttering feels so hard, and more importantly, why forcing yourself through it the way you've been trying to do it thus far isn't working.

So if we haven't already met, hey, I am Jennifer Roskamp. I am a certified strategist and life coach and founder of the Intentional Midlife Mom and the Intentional Mom. And I am so glad that you are here. Now, if you've been around for a while, you know that this is not a place where we have surface level conversations. You know that I also don't hand you a checklist and just send you on your way. When we have conversations here, we go deeper than that.

And when I work with women on clutter in their homes, in all kinds of ways, I go deeper than that. Because the clutter in your home is is rarely, if ever, just about the stuff. And so today we're gonna be, I'm gonna be proving that to you again. So by the end of our time here today, you're gonna have a completely different way to approach clutter, one that actually creates momentum instead of burnout.

One that works with your brain instead of against it. One that doesn't require you to just white knuckle your way through a room and come out the other side crying and exhausted and a complete mess, wondering why you even started in the first place. Hopefully that sounds exciting because I know it does for me. So the first thing that I want to address though is the biggest mistake that women make when they approach decluttering.

Now again, we kind of talked about this in the intro a little bit, but the problem is is that every we we assume that every single item requires the same amount of emotional energy, the same amount of mental bandwidth. And it just doesn't. Some decisions that you have to make about what's in the pile or the box or the bin, those are actually going to be obvious decisions. You pick up something and you immediately know, yes, this is something that I need to keep, or no, this needs to go.

Easy done. On to the next thing. Some decisions need little thought. You hold the item and you think about it for a minute, and then you know that it needs to go wherever it needs to go. And some decisions, not many, but genuinely some decisions need more time. And that's why when I work with women on decluttering, I give them three simple categories to use when they're deciding what to do with their stuff.

So the first category is yes, right? An easy yes. Yes. Keep it. This is this belongs here. Done. The other category is obviously the opposite. It's the no, right? It's the this this doesn't belong here, and I know it. And I've probably known it for a long time, but this needs to go. That's the second category. The third category is the not now category. And that category essentially says,

I need some more time on this one. I need some more time to decide. This is not a surf. The things that are in the not now category are things that need more thought, more deliberation, more bandwidth. And so many women, though, what they do is they treat not now the stuff that they're not deciding about right now, up to this point. They treat a not now thing as a failure. Like if they can't make the decision.

Right now, in this second, they've somehow failed. They they're avoiding and they've proven that they can't do this. But for me, the way that I teach not now, which we're gonna go deep on that here, but it's not a failure. It's actually wisdom. Because the truth is, not every item deserves a forced decision.

Not every item when you go into a decluttering, you know, little episode, right? You're gonna spend a half hour working on your clutter. Not every item needs to be handled today. Sometimes, not now, is simply you recognizing honestly and with clarity that you don't have the emotional capacity or the mental bandwidth to process that particular item right now in this moment.

And that is completely okay. That is different from how you have probably handled the hard things before. So I'm gonna say it again. When you are using my three categories of yes, no, and not now, you do not have to make every decision about every item today. You only need to make the decisions with those three categories about the things that you're ready to make decisions about today.

Now, know that this single reframe has unlocked more progress for women that I've worked with on clutter than almost anything else. Because the moment that you give yourself permission to have a not now category, a not now pile, a not now bin, the pressure releases enough for you to just be able to keep moving. And the best part is you actually made a decision.

Your decision is not now, but you will return. And now I'll be explaining more about the not now concept next week Tuesday in our conversation. But for now, know that choosing not now is actually making a decision rather than avoiding making a decision about these hard items as you have in the past. In the past, again, you've come across your item.

And you have said, and it has felt hard, right? You know, I don't have the ability to make this decision right now. So I'm just gonna throw it back down and avoid it. That's been what you've done, because that's what every woman does with the hard stuff up to this point. But what I am doing now is giving you permission to say, you know what? I recognize I don't have it in me right now. And so I'm going to set it down for now and say, not now.

But I will return. That's what this category does. Okay, so

Once women stop believing that every decision they have to make about the stuff is going to be hard, they usually make a different mistake. They decide to prove how serious they are by starting with the hardest thing in the house. The attic, the storage room that is full of boxes from 20 years ago, the baby clothes, the bins of sentimental items that they've been dragging from house to house for a decade or longer. And I genuinely

Have a hard time understanding that logic. You would never tell someone who decided to start running to go ahead and sign up for a marathon on day one, right? That would be torture. That would be that would be setting them up to fail before they even got started. Yet women do this to themselves all the time when it comes to decluttering. They go straight for the heaviest emotional weight in the house and then wonder why they're burned out before they ever get through the first box.

But here's what I want you to do instead. I want you to start with the easy wins. Things like expired food in the pantry, broken items that you've been meaning to toss, duplicate kitchen gadgets, obvious trash, the junk drawer that's full of things that don't belong to anyone. Why? Why what why would we start here? Because success creates confidence. Confidence creates momentum.

And momentum creates action. So think about building strength up in the gym, right? Nobody walks into the gym on day one and goes straight for the heaviest weight on the rack. We know that that would not end well, right? But we know that you do build strength through repetitions, through consistent, manageable repetitions over time. And then gradually you can handle more.

Decluttering works exactly the same way. Every easy win that you collect, every day that you every bag that you fill, every shelf that you clear, every decision that you make without it costing you everything, well, that is repetition. You're building your decision-making muscles. You are proving to yourself that you can do this. And then when that muscle is stronger, the harder stuff.

gets more manageable. Not necessarily easy, but more manageable. So please start with the easy stuff. It is not cheating. It is actually a very legitimate, very smart strategy in terms of how to attack your clutter. Now, I want to just kind of take a pause here and talk about something a little bit more deeply because sometimes we get this far into the into the decluttering conversation and women are nodding along.

Yes, start easy. Yes, build up my momentum. Yes. And then they walk into the room or they haul out the bins and they still can't move. And if that's you, I want to offer you something different. Sometimes the clutter, oftentimes, the clutter is not a problem. Sometimes the reason why you're still paralyzed is because you are already dealing with too much.

Here's what I mean. Think about what you're managing right now, just in your life, right? Work stuff, family stuff, maybe aging parents who need more of you than they used to. Maybe it's your marriage that's going through its own season of difficulty. Maybe there's health concerns yours or someone that you carry about, care about. Maybe there's emotional exhaustion that runs so deep you don't even know how to name it. There's the invisible mental load of tracking all the things, every need, every deadline, every

Transition happening in your household. And then you look around your house and you tell yourself, Well, I should be able to do this. But based on what? Who says you should be able to do that? Who decided that on top of everything else that you are managing, you should also have the bandwidth to tackle your home and the energy and the focus and the follow-through to do that? Here's the truth bomb you probably need to hear. Sometimes the clutter itself, the stuff.

Isn't what's hard. Sometimes what makes it hard is that you are already overloaded and overburdened, and therefore doing next to nothing with all of that stuff boils down to nothing more than just the wrong timing. And this is why I talk about capacity management so often in the work that I do with women. Because women try to keep solving capacity problems with productivity solutions.

They think if I just had the right system or the right method or the right bin or the right labels or the right checklist, I could get this done.

But in the case of being overburdened, it doesn't matter. It's not a system problem. The root cause, what's keeping you stuck with the stuff, is a capacity problem. And these two things are not anywhere close to the same thing. So before you beat yourself up for not being able to just push through and make it through that box or bin or pile of clutter, I want you to ask yourself something. What if the issue isn't that you're struggling with the clutter?

What if you are simply asking too much of yourself right now? That question isn't permission to give up, by the way. It's just permission to be honest. Because when you know what you're actually dealing with, you can make a real plan. Instead of forcing yourself through something you don't have the capacity for, you can find the version of progress that actually fits your life right now. Now, know that this next

little piece that I'm gonna share with you might be the most important thing I teach about decluttering. And it goes against everything that you've probably been told. Most women stop decluttering when they are exhausted, when they are frustrated, when they are overwhelmed, when they are emotional and on the verge of tears and surrounded by pot piles and wondering why they even started in the first place. In other words, they stop at the absolute worst possible moment.

And then their brain files that experience away. It stores that experience as evidence. And then the next time you think about decluttering, that evidence gets pulled right back up. And you're reminded of things like that last time was miserable. Last time was exhausting. Every time you work on clutter, you cry for over an hour in the spare room surrounded by all the baby clothes and the pile of things that you couldn't decide about. And so when that's what you're recalling.

You avoid it and the clutter grows and the cycle continues. So here's the new rule that I want you to adopt. When you are working on decluttering in any way, stop while you are still winning. Walk away. Be done. Be done while you still feel good about what you've done. Stop when you have energy left. Stop when you are still making decisions about the stuff.

With confidence. And I know that this sounds counterintuitive, right? You finally got started. Why would you stop before you're done? But I want you to think about a party. There's a huge difference before but between leaving a party while you're still having a great time. You're laughing, you're energized, you're glad you came, versus staying three hours too long and leaving miserable, overstimulating, and regretting the whole thing.

Which version of those two scenarios, which scenario makes you want to go to the next party? Well, obviously it's the first one. And decluttering works exactly the same way. When you stop on a high note, high note, when you stop while you still feel capable and successful and in control, your brain files that away too. It remembers, huh, that wasn't so bad. You know what? I think I could actually do that again. I actually felt good afterward. And that right there.

Matters enormously for your future motivation because your next clutter session starts where your last one ended emotionally. If your last session ended in tears and frustration, that's where you're starting from next time. But if your last session ended with a bag by the door and a sense of accomplishment and feeling proud of yourself, well, now that is your new baseline.

So the goal is to stop while you are still winning. So let's now talk about what's actually happening in your brain when you declutter, because this is where it gets really important. Every single decluttering session becomes evidence. Evidence for one of two stories that you are telling yourself about who you are and what you are capable of. So story number one is: decluttering is awful, decluttering is exhausting.

Decluttering is overwhelming. I hate doing this. I always fall apart. I can never finish. This is too hard for me. I guess I'm just gonna have to live with it. Story number two is this I can make decisions. I can handle some discomfort. I can trust myself. I can make progress. I am capable of doing hard things. Every decluttering touch point you have.

Is reinforcing one of those two stories. It's one or the other. So I want you to ask yourself: what kind of evidence are you collecting? Because your future motivation is being built right now. Every time you push through until you're crying and call it a failure, that is evidence for story number one. Every time you stop while you're winning and feel good about what you did, well, that's evidence for story number two.

And here's why this matters beyond just decluttering. The woman who trusts herself to get off the couch and do hard things, that's not just a woman who has a cleaner home. That's a woman who shows up differently in every area of her life. She's the woman who follows through on what she says she's gonna do, who makes decisions without spiraling, who believes literally to her core that she can be trusted. You are.

Building that woman one session at a time when you make sure sa story number two is the story that you are having every single time you work on decluttering. So I want to take a minute too to address something that I know is probably sitting in the back of your mind. Because even after everything that I've said here today, even with the new categories and the easy wins and the stopping while you're winning, some of you I know are still thinking.

But I need to finish. The basement isn't going to declutter itself. The garage is out of control. The spare room looks like a storage unit. I need to make real progress. And so if you're thinking things like that, here's what I want you to hear: that thinking is exactly what's keeping you stuck. When the goal is to finish, when the goal is to complete the entire room, when the goal is to finish the entire floor, the entire house.

You have set yourself up to fail before you even begin. Because no matter how much you get done in one session, it will never feel like enough. And instead of celebrating what you did accomplish, you will focus on everything that's left. And that is so discouraging. That is so demoralizing. And the next time feels even harder. So what if we changed then the goal completely? What if success today?

Or the next time you work on your decluttering looked like 10 decisions. What if it looked like one shelf cleared, one donation bag filled, 15 minutes of focused effort? Because progress creates momentum. Perfection creates paralysis. I would so much rather see you make 10 solid decisions the next time you declutter and feel great about it and come back again tomorrow, the next day.

Then I would see you two attempt to do the entire basement in one brutal six hour marathon, but burn yourself out completely and not go back in there for six months. Ten decisions today, ten decisions tomorrow, ten decisions the day after. That adds up to something real. That adds up to a woman who shows up consistently and can and performs consistent action, even small, quiet, unimpressive action.

Those women will always beat the occasional dramatic overhaul that you can't ever quite recover from. You just need one solid plan. Now, here's the thing that most people miss entirely about decluttering. It's not actually about the stuff, right? Yes, the clutter is real. Yes, the piles need to be dealt with, but what you are actually practicing when you declutter, what you are actually developing has very little to do with those objects themselves.

You are practicing decision making. You are practicing self-trust. You are practicing follow-through. You are practicing the ability to tolerate discomfort without running from it. You are practicing respecting your own limits. The clutter is just what where the practice happens. It's it's like the gym. It's like the the road that you're logging miles on. It's it's the weights themselves as you're in training.

Every item that you pick up and make a decision about, it's another repetition. You are strengthening a muscle. The same muscle that will help you make hard decisions in your marriage. The same muscle that will help you set a boundary without caving. The same muscle that will help you say no when you need to and yes when you need to, instead of just defaulting to whatever requires the least conflict. This is why I say the object isn't the lesson. You are the lesson.

The clutter is just the classroom. So one of the things that I come back to again and again in working with women is this idea of being in the driver's seat of your life, not in the backseat along for the ride. The driver's seat. Shout out to all of my accomplished lifestyle friends. You know exactly what we're talking about because we talk about this weekly, usually multiple times a week. But here's what I know about clutter. It will absolutely try to take the wheel if you let it.

It will dictate your mood the moment you walk into a room. It will set the tone for your whole day before you've had a chance to choose how you want to feel. It will pile on guilt and shame and overwhelm onto your shoulders without asking permission. It will tell you that you are failing, that you're behind, that you should have dealt with this already, that there's something wrong with you. Clutter does not get to define anything about you.

You can be the one in the driver's seat. You can be the one deciding where you start. You can decide what area you work on. You can decide how long you'll work. You decide when you're done. That's the smart way to have decluttering sessions with yourself. You don't let the clutter decide. You don't let the guilt decide. And you don't have to deal with that overwhelming feeling that you'll never get on top of this. You get to make the decisions.


Because the moment the clutter starts dictating your emotions and your schedule and your sense of self-worth, you have climbed into the backseat where you are along for the ride that your clutter is taking you on. And it's time for you to start being the one who decides how the clutter is going to get managed. So just to recap the big things we talked about today.

Know that not every decision about this stuff is going to be a hard one. And you don't have to make every decision today. Use the three simple decision categories. Yes, this stays. No, this doesn't stay. And the third one is that not now category where you say, again, I don't have the ability to deal with this, make a decision about this right now, but I will return.

Know that again, that is not failure, that is not avoidance anymore. That is actually wisdom because you have decided this is not for me today. Takeaway number two that I want to make sure you walk away with is to start with easy wins, not the hardest thing in the house. Build your decision-making muscle through repetition before tackling the emotionally heavy items. Momentum is built on small successes.

Takeaway number three, stop while you are winning. End your decluttering sessions when you still feel capable and successful, not when you're exhausted and emotional. Your brain keeps score, and the next session is going to start where your last one ended. The fourth big takeaway is that the goal is not to finish. Consistent small action always beats the occasional dramatic overhaul.

10 decisions today, 10 decisions tomorrow. That is how real change happens. And I want to leave you with this: the goal is not to force yourself through clutter. The goal is to build enough positive experiences with clutter that you stop being afraid of it. Because when every session ends in misery, your brain learns one thing: avoid this, stay away from it. It's dangerous.

And your nervous system cooperates by throwing up every possible barrier between you and that pile, between you and that room, between you and that storage unit. But when you start building a different kind of evidence, when you learn that you can make a few decisions, when you learn that you can stop when you feel successful or trust yourself to come back tomorrow, that's when everything changes. Suddenly the clutter isn't controlling you anymore.

You're not bracing yourself every time you walk by that room. You are not letting it define how you feel about yourself as a person, as a mother, as a woman. So you are able to finally stop white-knuckling your way through it. You stop making the clutter mean something about your worth. And little by little, decision by decision, you get back in the driver's seat because progress is always progress. And you can start again at any single moment.

Now, before I let you go, I want to give you something practical to walk away with. This week, I don't want you to try to finish a room. I don't want you to try to tackle the garage or the basement or the spare room. I want you to pick one small area, set a timer, make 10 decisions, and then you stop. You stop, you will still be winning. I promise, after just 10 decisions, and that's it. And while you're doing it, I want you to pay attention to the evidence that you're collecting.

Which story are you writing for yourself today? Because the woman who trusts herself doesn't appear overnight. She is built one decision at a time. And you can start building her right now. If today's episode hit home, I would love if you would share it with a friend who needs to hear it. And if you're not already following this account, make sure that you hit that button now so that you never miss an episode. We talk about

Clutter every single week on a Tuesday, generally on a Tuesday. You can also follow me over on Substack, where I write about midlife clutter explained and solved. Be sure to check the show notes for a link to where you can go read those free publications that I write. They go a lot deeper and they very much align with what we're talking about here, too. So it's a way to get some more help with all this stuff.

But also with the emotional clutter and the mental clutter and the schedule clutter and the identity clutter, all those things. So thanks for being here today here today, friend. Now, next week, remember, we're gonna go deeper on that not now category. So if you're wondering how that works, make sure to join us next Tuesday. I'll see you then.