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Decluttering Regret + How to Overcome Your Fear of Letting Go [Episode 33]

“But what if I need that someday?” If you’ve ever struggled to declutter because you’re afraid to make the wrong decision — or if you’ve already experienced decluttering regret — this episode is for you. I’m sharing my own experience and a new perspective that just might help you move forward.

In This Episode:

  • My experience with decluttering regret (it’s probably not what you’re expecting!)
  • Why I don’t believe in toxic positivity and what it has to do with decluttering
  • How to overcome your fears and/or make peace with your past

Featured In This Episode:

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

Decluttering Regrets and How to Overcome Your Fear of Letting Go

Hey everybody, it’s Jen here, and welcome back to the Simply + Fiercely Show. And yes, I know I say that same catchphrase at the start of every single episode. I laugh at myself when I listen back to my work because I really feel like I should say something different or perhaps a bit more creative.

I wanted to record this episode for you today because I am so passionate about this topic. That’s another thing I say all the time, but I am bursting at the seams because we are going to be talking about decluttering regret and this is something I have so much to say about.

We’re going to break down how to overcome the fear of decluttering regret, and I’m going to share my personal experience with it. If you’re a regular listener, you know that I am a big believer in the power of storytelling.

I hope that sharing my perspective will help if you’re struggling with decluttering regret right now or if you are holding back because you’re afraid of it.

I’m getting ahead of myself a little bit, let’s start with the basics.

What is decluttering regret? (…What does that fear look like?)

What am I talking about when I keep saying decluttering regret? Well, decluttering regret is that feeling you have when you get rid of something and then at some point in the future, you regret getting rid of it.

This is something a lot of people struggle with to the point that they struggle to declutter anything because of this fear.

You’ve probably heard somebody say, or maybe you’ve said the words yourself, “But what if I need it someday?” That’s that fear of decluttering regret.

The fear of making the wrong decision or making a mistake. That fear of regret leads to paralysis and what happens is you hold onto the item, and you avoid doing anything because you don’t want to make a wrong decision.

Informal poll on Instagram

Out of curiosity, I did a little informal poll on my Instagram stories today, if you want to follow me, it’s @simplyfiercely.

This poll obviously isn’t like a scientific study, and it was a pretty small data pool. But I asked if this concept of decluttering fear or regret holds you back from decluttering.

·        33% of people said it was something they often struggle with.

·        53% of people say that it’s something that they sometimes struggle with.

And then I also asked people how many times have they experienced this decluttering regret in their own lives, and the answer was 67%.

The myth that decluttering regret doesn’t happen is not true

The reason I’m bringing this up is because I feel like there’s this myth in the decluttering community that decluttering regret doesn’t happen. People say, “Oh, you’re so afraid that you’re going to miss it, but I promise, if you get rid of it you’re never going to regret it.”

If you genuinely have this fear or you’ve experienced decluttering regret it’s almost like your feelings get brushed under the rug because we just don’t talk about it.

So, I want to talk about it because if you’ve been following my work, hopefully, one thing that you know about me is that I don’t like to pretend that hard feelings don’t exist, okay?

If you know my story, decluttering was not easy for me. I am not a type A organised personality. I am very sentimental. I feel very attached. And even now, I probably love stuff a bit too much for someone who calls themselves a minimalist.

What I’m trying to say is that I understand how and why decluttering regret happens. I think that acknowledging that it’s a valid point of view and offering some perspectives on how to work through it is much more constructive than just saying, “Hey, don’t worry about it. You’re never going to regret it.”

I’m going off on a tangent here, and I’m not pointing fingers or saying any particular person is saying this, maybe I’ve even said it myself, in which case I do apologise. But there’s this general kind of feeling that decluttering is the same as cleaning your house, and you should just be able to do it. You should be able to buckle down and get it done.

Or if you’re struggling with sentimental items, you shouldn’t because your memories live in your heart and not your stuff.

These things are usually said with good intentions and some of it has elements of truth. But I found that if you don’t feel that way, if your experience is different, then hearing everyone else say that it’s supposed to be easy or that you won’t regret it almost feels like you’re being gaslit.

Because if decluttering isn’t easy, if you do feel regret for getting rid of things, or if you do feel emotionally attached to your stuff, it’s like, “Well, what’s wrong with me?”

I’ve talked about this before in other episodes, one of the biggest hurdles I felt early on my decluttering journey was feeling like it was supposed to be easy.

Then when it felt impossible for me, because that’s how it felt in the start, I was like, “Oh my God, what’s wrong with me? Why am I so stupid? Why can’t I just do this? I’m a smart, educated woman. Why is it so hard to declutter?”

So that’s what I’m really mindful of. I’m mindful of the kind of shame that some people feel about clutter. Honestly, I could record a five episode series about the impact of shame on decluttering, but we’ll hold that off for another day.

What I just want to say is that I don’t want you to feel discriminated against, or as I said, gaslit by the people that you are looking to when you need support.

The Clear Your Clutter program

On that note, I wouldn’t be doing my job if I didn’t mention that this is the exact opposite of the way that I work with my clients in my group program Clear Your Clutter.

Clear Your Clutter is an 8-week group program that I run twice a year. The next enrollment is in January, around mid-January.

One of the cornerstones of that program, something I’m so proud of and what many of my clients give me positive feedback about, is my emphasis on compassionate curiosity.

It is a judgement free zone. There’s no toxic positivity where we try to pretend like our emotions don’t exist and there is no one size fits all solution. Instead, I meet you where you are with your clutter.

I could go on and on about the program, but I know that’s not the point of this episode. I’ll just say that if you listen to the podcast and what I’m saying resonates with you, this is very representative of the work that I do in my programs.

I help you find new perspectives. I help you create a new relationship with clutter so that when you’re letting go, it feels more like empowerment, something that you’re feeling a bit excited to do, as opposed to punishment where you’re sort of forcing yourself to get rid of things. A bit like toxic diet culture. You know what I mean? We’re anti that.

We are about compassionate lifestyle change. So, if that is something that you are interested in learning more about, you can learn more here – Clear Your Clutter.

Jen telling her own story on the impact of decluttering on mental clarity and personal growth.

We have established that decluttering regret is a real thing and it’s something that many people struggle with. So what do we do about it?

As I said, I believe in the power of stories, so I think that the best way to answer this is to tell you about my experience with decluttering regret. And here is the truth. I have experienced decluttering sadness. I have felt kind of nostalgic or kind of wishful for something. I’ve thought, “Oh, isn’t that a shame that I’ve gotten rid of that?”

But I have never experienced decluttering or regret, and here’s why.

When I decided to record this episode, I started by sitting down and took 10 minutes and tried to think about things that I have gotten rid of in the past that I feel a bit sad about. Off the top of my head, I was able to come up with a few things. I’m feeling very sad now just thinking about this.

When I was in high school, I saved up what felt like an extraordinary amount of money for a 16-year-old to buy these J. Crew leather boots.

I’ve been living in Australia for almost 20 years, but I grew up in America in the ’90s. Back then the joy of my life was when the J. Crew catalogue arrived.

I saved up for ages for these beautiful leather boots, got them, and then never wore them. I didn’t have the confidence to wear them. They weren’t really my style at 16. I don’t even know what happened to them, but when I got rid of them, they would’ve been brand new, never worn.

I think about them now and my foot size has not changed. Lots of my other sizes have, but my foot size hasn’t. But oh my gosh, those boots, I wish I had them now.

I also have a memory of thrifting. I used to be a huge thrift shopper. Is that what they call it in America? I can’t even remember. Like, just secondhand shopping. I remember once finding a vintage coach leather bag. It was the old style where it was just nice, simple leather without the logo and everything, like an over shoulder bag. I have no idea what happened to that.

More recently, a few years ago, I decluttered two cashmere sweaters because I don’t wear them. I live in a hot climate but of course, I go back to visit family overseas fairly regularly and now I’m kicking myself that I didn’t save these cashmere sweaters.

That is just what I thought of off the top of my head. There were also practical things. A few years ago I got rid of a shoe rack, which would be really handy to have right now.

There are also sentimental items.

For those who don’t know, my younger brother passed away when he was 21. I kept a lot of his stuff for a long time. One of those items was this stuffed dog, which he used to call Chippy. It was one of his favourite things.

I decluttered that, I don’t know, maybe eight or nine years ago. And when I think about it, I don’t necessarily feel like it was a mistake, but I feel this nostalgia and I think, “Did I do the right thing? Will I regret it later?” I feel this weird kind of wishy-washy emotional feeling when I think about it.

Despite all these confusing feelings, because they are quite confusing, there’s sadness and nostalgia and annoyance, but I can say that if I’m really honest, I don’t feel regret about anything that I’ve decluttered, and here’s why.

When I look at the big picture, when I look back a decade ago or so, there is so much that has changed in that period of my life that I could potentially trace back to my decision to declutter and simplify.

There are practical things like where I currently live and what I do for a living, but there are also less tangible things like the way I feel about my relationships. I have really strong friendships. My marriage right now is stronger than ever before.

There’s also the way that I feel about myself. Something else I’ve talked about before in the podcast, I’m 42 and I have grey hair. I’m starting to get wrinkly. I’m also heavier than I’ve ever been before. Not to say that those are bad things, but I think we all know that those things don’t fit into the socially accepted boxes of how a woman should look if they want to feel good about themselves, right?

There are a lot of reasons why I “should” feel crappy, “should” in quotes, but right now, I can honestly say that I have so much self-love and so much confidence, which blows my mind because I spent the first 30 years of my life dealing with crippling insecurity. To not feel that way now, it blows my mind sometimes.

What Jennifer learned from decluttering, about herself, her values and what she’s capable of?

I genuinely think if I reflect on all of this, that I can trace a lot of it back to my decision to declutter.

I know that you might be like, “What are you talking about? How can you say that?” I know it’s weird because I am the first person to put my hand up and say decluttering is not a magic pill.

It’s not going to change your life overnight. You’re not going to take a few bags to goodwill and then be like, “Oh, look, everything in my life has changed.” But I also know that when I went through this really intentional process of going through my home, going through my life, and making those hard decisions about what to keep, that whole decluttering process was also a huge learning experience.

I learned so much about myself, who I am, what I value, and what I’m capable of, and I think we can all agree that that is priceless.

That is a huge reason why even if I’m sitting here thinking about those beautiful boots and how I would wear them all the time now, I wouldn’t trade that because I have this experience that I’ve had the past 10 years.

On top of that, obviously, as I said, there’s what you learn about yourself when you’re decluttering.

Let me say first of all, that I’m a bit of a dreamer. I’m an optimist. I’m not like a huge woo-woo person. When I say I believe in magic, I don’t literally believe in magic, but I just believe that we live in this world with so much possibility, so much untapped possibility.

When you create space in your home, in your schedule, in your mind, you are creating space for those possibilities and new ideas.

Again, I don’t mean that in a woo-woo way. What I mean is that, if you are very busy and your life is cluttered and you’re overwhelmed and you don’t have a minute to sit and relax, you have no capacity to think beyond the basics.

What do you need to do to get through each day? Or you’re looking around your home and you’re like, “Oh, I need to be dealing with that. I need to clean that. I need to deal with that pile of crap on my dresser in my closet.”

But what if you could carve some of that back? If you could create that feeling of freedom and ease that comes with decluttering, then who knows what would happen.

I cannot understate the value of time to think about our lives, to think about what’s important, maybe you’d realise, “Hey, I actually, I’m in this job and it pays good money, but I don’t actually like it. I actually hate it and I hate going to work every day. And maybe it is possible. Maybe it’s not too late. Maybe I could go train to something else.”

Or maybe you’ve been living in survival mode for so long, and when you create that space for yourself, you’d be like, “Actually, this relationship that I’m in, a friendship, a romantic partner, whatever, it’s toxic and not good for me. Maybe I need to draw some new boundaries or change my relationships.”

Again, the possibilities are endless. That’s just a few examples, but sometimes you never know what might come up until you create that space for yourself.

This is why I will never regret it even though I may feel sad about a few of the individual items that I declutter.

Practical tips on overcoming decluttering regret

That’s what I want to offer you. If you are experiencing decluttering regret or if you are afraid to declutter because of it, I’d like you to acknowledge that we don’t know what the future holds.

No one has a crystal ball. I cannot tell you that you will not regret getting rid of something. But I can tell you that if nothing changes, then nothing changes.

So maybe you got rid of something and you’re feeling a bit sad, and it’s okay. Those feelings are valid. But you also don’t know if getting rid of that led to something else and you can’t see that they’re connected. If you can hold space for that in your mind, it makes it a little bit easier to make peace with that change.

Also on the concept of regret, I don’t know about you, but for me, the worst kind of regret is the regret of not knowing, the regret of what if, the regret of not telling somebody you love them, the regret of not saying yes to an opportunity.

Obviously, there are exceptions, like we don’t want to put your health in danger, but most of the time, that’s not the kind of consequences you’re facing. 

So for me, again, I’m a bit of an optimist, but I would always rather try and fail. I would rather take that leap and see what’s on the other side than just stay stuck in a situation that doesn’t make me happy. 

So, if you can associate that kind of mindset, that bigger picture mindset with your stuff, I think it makes it a lot easier to either make peace or to let go.

Now, before I wrap this up, I do want to say that I can just imagine right now that some of you’re saying, “But what does it matter? It’s just one sweater. It’s not going to matter if I just keep this one sweater or this one more book or this one more whatever.” 

I know because that’s probably what I would be saying as well if I was on the other side of this conversation and I want to address that before we go. 

I’ll start by saying, you don’t have to get rid of anything you don’t want to. My definition of minimalism is about alignment. There are no roles about what you can or cannot keep as long as it’s aligned with what matters to you. 

But you also have to ask yourself, “Is it really just one item?” Or is it like that saying, death by a thousand cuts?

We’ve all heard the idea that little steps lead to progress. For example, if you want to get in shape tomorrow, you don’t run a marathon the next day. You start small, you start walking, and then you start jogging. Eventually, with time, you’re going to work your way up to being able to run a marathon. 

That same concept of small steps also works in reverse. Sometimes it’s little things. I mean, again, I’ve done this so much in my own life. We trade away our dreams one piece at a time. 

I used to be in a considerable amount of debt because of my shopping habits. I think most of you know that I used to be a shopaholic and it was always, “One little thing. Just one more thing. What’s it going to hurt?” But all of those things, I look back now and I probably could have bought a house with the money I spent on clothes I didn’t wear. But every time I was like, “What’s one more thing?”

Sometimes you have to spend some time in honest self-reflection. And know that it takes courage to reverse direction, it takes courage to believe that something bigger is possible. 

When I work with my clients, the biggest challenge to everything that we just talked about is sometimes self-belief. To believe that, “If I get rid of this sweater, it might essentially lead to something better, that there is something bigger or just different.” It’s not always better, it’s just different, and it’s possible for you.

Let’s sum things up by saying that I believe it for me, I believe it without a shadow of a doubt, and I genuinely believe it for you as well. 

That is why I do the work that I do, because I remember exactly what it was like to feel like I was stuck, like I was trapped in my life, like I was settling for less than what I knew was possible, and I don’t want that for you. 

So if you don’t have that self belief, feel free to borrow mine. I believe that if you declutter something and regret it, you are strong enough and capable enough to find your way forward. Okay? That’s it for today. Take care and talk soon.

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