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How to Avoid Mid-Decluttering “What Have I Done?” Regret [Episode 42]

We’ve all been there: you start motivated and excited to declutter! But then *bam* … you hit a wall, run out of energy, and you’re left surrounded by piles you either have to deal with or put away. (Neither of which sounds like a good option when you’re mentally and physically exhausted!) If you can relate, check out this episode of the Simply + Fiercely Show to learn how to avoid mid-decluttering regret.

In This Episode:

  • why mid-decluttering regret leads to chronic procrastination
  • a common decluttering tip I don’t recommend
  • how to avoid decluttering burnout

Featured In This Episode:

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Note: this is not an exact transcript and has been edited for clarity.

How to Avoid Mid-Cluttering What Have I Done Regret

Hey everybody, it’s Jennifer here, and welcome to another episode of the Simply + Fiercely Show.

Today, I’m going to talk to you about how to avoid mid-decluttering regret.

And by that, I mean when you feel inspired and you start off to do a big decluttering job, let’s say you’re decluttering your closet and you take everything out and you dump it on your bed and maybe you go through your drawers, you get everything out.

You’re feeling inspired, and you start going through your things and then you hit a wall.

You lose all your motivation. You’re exhausted, you have no energy.

You look around at your giant piles of stuff which you have dumped out everywhere, and you have this moment where you think, “Oh, my God, what have I done?”

I used to think that was just me, but it must be very universal because I’ve seen tons of Reels that feature this same concept recently where this person is sitting in a room with a huge mess and stuff everywhere kind of going, “What have I done?”

If you’ve ever been there, this episode is for you. I’m going to talk about how we can avoid this.

Negative Decluttering cycle that leads to mid-decluttering regret

But first, I want to quickly point out why this is such a problem.

Nobody wants the experience of running out of energy when you still have your stuff dumped out everywhere because now you have to clean it up, and that’s not fun for anybody.

But I also want to point out two other things.

One is that when you are in that state and you’ve taken everything out and you’re surrounded by all of the stuff that you want to declutter, and then you run out of steam, yes, you have the ‘what have I done’ in terms of why did I take everything out, why did I take on this project today?

Now, it’s such a big mess and I’m exhausted.

But what I have found when I’m decluttering and I’m sort of stuck in one of those situations, is that I’m often usually a little bit emotionally fragile, and seeing all of my stuff out really, really gets to me, right?

I don’t know about you, but when I was a shopaholic and I had tons of clothes, yes, I knew I had tons of clothes, but when they were all tucked away neatly in my drawers and my closet, et cetera, it was easy to kind of pretend like I didn’t have as much as I did.

But then, when I dumped it all out, it was kind of like being smacked in the face by reality and just seeing how much stuff I had.

So, the whole ‘what have I done’ was yes, it was like, “What have I done today?”

But it’s also like, “How did I let it get this?”

The shame and overwhelm I would feel once I realized how many clothes were out there would hit me hard.

And I suppose some argue that that’s good, maybe you need that wake-up call to shake things up.

But for me, I found it to be kind of the catalyst for a negative cycle.

So, if I go to declutter and I have a negative experience and I don’t accomplish as much as I thought I was going to do, I have this overwhelming sense of shame about all of the clothes that I’ve bought, and I just also feel exhausted.

It’s the worst thing.

You’ve then created this giant mess and you look around and you’re like, “Oh God, how am I going to deal with this?”

It’s not fun and the next time you go to declutter, you remember that.

You remember how stressful and anxious and the giant mess, you remember all those negative feelings.

Now it’s that much more challenging to get motivated to start again.

Even more than that, if your memory of decluttering is that it was a massive time-consuming project.

If you’re anything like me, I was just trying to shove everything back into my closets at that point.

What I learned from the experience was decluttering is really hard work and it’s going to take me a lot of time so there is no point in starting until I know that I have tons of time to work on it.

The consequence is that I kept procrastinating about decluttering.

I kept saying, “Well, now it’s not a good time. I don’t have enough time. I’m too busy. I’m not going to start today. I will wait till a better time. I’ll wait till the holidays. I’ll wait till the summer. I’ll wait till some invisible point in the future where I’m not going to be so busy.”

But if you are anything like me, you may have realized that often that point never comes because other things come up and it creates this cycle where you never really have the time and energy to do the decluttering that you want to do.

That’s why I’m recording this episode.

How to avoid mid-decluttering regret in a way that is sustainable

I would like to help you avoid that mid-decluttering regret so that you can take a more slow and sustainable approach to decluttering.

This might sound a bit wild because it’s very different than what a lot of decluttering advice says, but I don’t think that you need to do it in one weekend or do it in one week.

I am a big fan of a slow, steady, sustainable approach, where we spend a bit more time thinking about our stuff and what we want to keep.

The result is that we end up with spaces that we love. Spaces that serve our lifestyle.

We end up decluttering in a way that doesn’t burn us out, and we learn a lot about ourselves. Then we can apply those lessons to other areas of their life.

First tip – You don’t have to take everything out of your space to declutter

The first tip is probably the most obvious, but I do want to point it out.

That is, you don’t have to take everything out of your space to declutter.

Yes, I know that’s what a lot of advice says you need to do.

I’m pretty sure the Kon Mari method recommends that you always start by taking everything out so you can see it all.

And sure, there are some situations where that might make sense.

If you are decluttering a toolbox, let’s say, then you do need to know, do I have five hammers? If so, I don’t need to keep so many. So, I’m not saying that method never works.

But in my experience, lots of time what we are decluttering is not dependent on the other items that we keep, even when we think it does.

So, let’s say for example that you’re decluttering your closet and you hear a lot of advice that says, “Hey, look, you have seven red shirts. You only need to keep one.”

Logically it makes sense, and for some people that might work.

But for me, what matters more is first of all, are you even wearing red shirts? Do you even like red shirts? Let’s get that out of the way first.

Then we can evaluate each one on its merits.

If you have a red shirt that you never wear because you don’t like the neckline, it’s a bit too low. Or it doesn’t fit right. Or it’s a bit too fancy for your lifestyle. Whatever the reason, you can make a decision not to keep that red shirt and it doesn’t matter how many other red shirts you have.

You don’t need to keep something that you don’t feel comfortable wearing, whether that’s your only red shirt or not.

We don’t live in a world, I guess unless you work at Target or something, but we don’t live in a world where everybody needs a red shirt.

So, this concept that whether you keep something depends on what else you own is just simply not true most of the time.

For that reason, you don’t need to stress yourself out by pulling everything out of your closet.

For me, the goal of decluttering was not about owning as little as possible.

I’ve worked with clients who have decluttered a lot and they don’t own a lot of items, but they find themselves stuck in a cycle where they’re constantly buying new things and then constantly decluttering things.

They didn’t have that much stuff at any one point in time, but the consumption cycle, things coming in and things going out is still out of control and that’s not what they want.

So, owning as little as possible is not the goal. Instead, what we want is a space that is really functional for you and represents your style, and your taste, but also your lifestyle, your realistic constraints, like the size of your home, et cetera.

When that’s the ultimate goal, instead of going through a million items and picking them up one at a time and being like, “Do I like this or not?” It’s better to reverse-engineer your space.

One analogy that I could use that would help you visualize this is if you are someone who had a pantry.

If you only have five things in your pantry, then yes, your brain should be like, “What can I do with these five items?”

But if you have 200 items in your pantry, it’s better to decide what you want to cook first, then look for the items.

So, if you take my closet for example, which had I’m sure well over 200 items, instead of going through everything kind of one at a time, be like, “Oh, should I keep this? Should I not?”

I don’t need to dump everything out and make a huge mess of my bedroom and stress myself out to decide what to keep.

I can start by thinking about, “All right, what kind of closet do I want? What are my favorite things? What do I wear most often?” And then, I can work back from there.

So, I’ve got my favorite things. And then, it’s almost like you shop your closet and think, “Okay, so of the stuff that’s here, if I was building my ideal wardrobe today and I’ve already pulled out some of the stuff that I really like, what things would go with that?

You would build your ideal wardrobe and then get rid of the rest.

It’s not always that simple, but I think that that kind of perspective of starting with the end in mind is so powerful and can remove some of the overwhelm.

You don’t have to do it all at once. You can just do it in little bits and pieces.

I want to mention that if this is something that resonates with you, I have a program called the One-Day Closet Cleanse, which is built around this concept of reverse engineering your closet.

We build your wardrobe around what you enjoy the most, what you genuinely like wearing.

Then I show you how to declutter the rest.

That’s the One-Day Closet Cleanse but regardless of whether you’re interested in that or not, the concept is the same.

You do not, in most cases, have to take everything out to start decluttering.

You can pick up an item, look at it, and judge it on its merit independently of what else you own.

You can start by saying, “What is it that I want?” And go from there.

Second tip – Set a timer and don’t spend longer than the set amount of time on any one item

Tip number two is something that I teach inside my group program, Clear Your Clutter.

I highly recommend that everyone do this.

If you’re someone who gets stuck or you’re decluttering a lot of space and you’re worrying about running out of steam midway through, use a timer.

Set a timer for say five minutes or three minutes, and don’t spend longer than that set amount of time on any one item.

Now, that doesn’t mean you won’t get stuck, that doesn’t mean you’ll have an item where the end of three minutes or five minutes will pass, and you won’t know what to do.

When that happens it means that that item is not easy to declutter. It’s what I call stubborn clutter.

There might be some emotional detachment or something you have to work through.

You don’t want to get stuck in that heavy kind of decluttering. Put it aside and come back to it later.

You want to keep going so you don’t end up burnt out halfway through.

Keep going through your space and set all your difficult-to-declutter items aside.

Then you can pick them up one at a time because these are the items that are hard to declutter.

Third tip – Recognize that decluttering is both physical and emotional work

My third tip is if you recognize that decluttering is both physical and emotional work, you can plan accordingly by setting realistic expectations.

Part of the reason that people get stuck while decluttering is because they think it’s a cleaning job and cleaning is hard physical work, but usually, you can just be tough and push through it.

I don’t love cleaning. I’m not a naturally clean or organized person. But, if I set a goal to clean the bathroom, I can just turn on some loud music and push my way through, even if I don’t want to get it done.

Decluttering has elements of that, but it’s also very emotional and energetically draining.

You have to make decisions over and over and over, and science shows us there’s the concept of decision fatigue.

We can only make so many decisions, and then our brains start to fatigue and the quality of our decisions decreases.

I think that’s what this whole mid-decluttering regret is. It’s when you hit the wall with decision fatigue.

A lot of the spaces that we declutter, even if they don’t seem like emotional items, there’s still emotion attached.

I would argue that everything you struggle to declutter has some kind of emotional attachment behind it, even if you don’t realize it.

That is heavy work, it’s very draining.

This might sound a little bit silly, but honestly, I think it’s sometimes like going to therapy.

You’re digging up old stories, you’re poking around the past, right?

It is sometimes very hard on our psyche, so we have to recognize that and go in with that expectation.

If that’s the mindset that we’re going into decluttering with, then we’re going to know, “I’m not going to spend eight hours decluttering today.”

You wouldn’t go to therapy or you wouldn’t go to some kind of… There’s not much that you would do for eight hours, honestly.

Even if you go to work, you go to work for eight hours, but you’re not sitting there usually doing one intense task for the whole time.

The same applies to decluttering.

What I highly recommend that people do is to plan accordingly.

You want to stop before you reach 100%. You don’t want to burn yourself out.

You want to stop where you can maybe go for like 70% of what you think you can do.

Jen’s favorite tip is to build self-care into decluttering

One of my favorite tips is to build some kind of self-care activity into your decluttering routine.

So, let’s say this Saturday, you’ve got an hour and a half free for decluttering.


Plan that you’re going to spend an hour decluttering, and then maybe afterward you’re going to spend a half hour doing something that will help you decompress.

That’s going to be different for everyone.

Maybe you need to go for a walk. Maybe you need to call a friend. Maybe you need to read a book.

You need to give yourself time to recover from decluttering.

I hope you find that helpful. These are just a few things that you can try.

Some practical tips as well as some mental reframes that will hopefully help you avoid mid-decluttering, “Oh, my God. What have I done?” regret.

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