604 – Why Your Perfectionism is Keeping You Stuck in Clutter

(and What You Can Do About it) Part 1

Do you hesitate to start a decluttering project because you feel like you don’t have the time or resources to finish it?

You might be struggling with an underlying cause of clutter which is perfectionism.

Kathi Lipp and three-time co-author and frequent co-host Cheri Gregory start a two-part conversation about the straight line between perfectionism and clutter. Cheri speaks from an HSP (highly sensitive person) perspective and someone who struggles with perfectionism. Listen in as Kathi and Cheri discuss the connection between perfectionism and clutter, as well as:

  • How to get away from all-or-nothing thinking
  • The myth of form over function
  • What procrastination might be telling you

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An Abundant Place: Daily Retreats for the Woman Who Can’t Get Away

Are you overcommitted, overstressed, or just plain overwhelmed? These devotions will give you greater peace and perspective, and a plan for managing your busy life.

Have you reached the point where one more thing on your to-do list is one too many? Do you find yourself praying, “Lord, I don’t think I can handle any more stuff?”

Kathi Lipp and Cheri Gregory have been there. They want to encourage you, but even more important, they offer helpful solutions to make your everyday life easier. Get good advice on how to plan ahead, set boundaries with others and yourself, and be more intentional about self-care without the guilt.

Let Kathi and Cheri help you find a place of more joy and abundance, one devotion at a time.

Order your copy of An Abundant Place: Daily Retreats for the Woman Who Can’t Get Away here.

In this episode, Cheri asked us to spend 15 minutes reflecting on these questions:

When was a time you overdid it with perfectionism? Was it worth it in the long run? Did it serve you and your people?

Share your answers in the comments.

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Meet Our Guest 


Cheri Gregory

Through Scripture and storytelling, Cheri Gregory delights in helping women draw closer to Jesus, the strength of every tender heart. She is the founder of the Sensitive and Strong Community Cafe: the place for the HSP Christian woman to find connection. With Kathi Lipp, she’s the co-author of You Don’t Have to Try So Hard, Overwhelmed, and An Abundant Place. Cheri speaks locally and internationally for women’s events and educational conferences.

You can connect with Cheri at CheriGregory.comSensitiveAndStrong.com, on Cheri’s Facebook Page, and on Instagram.


Kathi (00:01.427)
Okay, this is Cheri Gregory, understanding the link between perfectionism and clutter. Five, four, three, two, one. Well, hey friends, welcome to Clutter-Free Academy, where our goal is to help you take small, doable steps to live every day with less clutter and more life. And if you have followed any of my writings, if you followed this podcast for any length of time, you already know my guest.

Her name is Cheri Gregory. She is a co-author with me on three books. I always wanna say two. I don’t know why. I don’t forget about the books, I know about them, but I feel like we’ve done some of our deepest work together. Cheri and I wrote Overwhelmed Together, You Don’t Have to Try So Hard, and An Abundant Place, our devotional together. She…

Cheri Gregory (00:38.137)

Cheri Gregory (00:46.424)

Kathi (00:56.999)
I’m gonna let her describe a little bit of her work because her work has changed over the years. And I think she is doing what she most loves to do. She is my go-to person for HSP issues, which is highly sensitive people. And I just adore her. So Sherri, welcome back to the podcast.

Cheri Gregory (01:19.199)
I’m just going to take and receive all of that. Yeah, I mean, what I do these days is I hang around highly sensitive persons in Sensitive and Strong, my membership, the Sensitive and Strong Community Cafe. I just got done doing my master class, Growing Sensitive and Strong, and it was hilarious because the first night as we were introducing ourselves one by one, oh yes, I found out about you through Kathy Lipp.

Kathi (01:22.157)

Cheri Gregory (01:42.682)
Oh, yes, I found out about you from Clutterfree Academy podcast. Oh, I found out about you from reading Kathy’s books. So my people are big Kathy Lip fans.

Kathi (01:46.28)

Kathi (01:49.415)
Oh, that makes me… Well, I’m big fans of their people. I’ve told you many, many times. HSPs are my favorites. I just did a whirlwind tour of San Jose. I had exactly one day and everybody, I almost have the people I met, either they were on the ADHD spectrum, ADHD, yeah. Feels like I was missing a letter there. Or they were my sensitive…

my highly sensitive people. So just explain what HSP is. This is not what this podcast is about, but kind of will be touching on some issues. So what does HSP mean?

Cheri Gregory (02:28.547)
The easiest explanation is it basically means sensory processing sensitivity, which means we are more easily overwhelmed than the average bear, often by external sensory stimuli. And more recently, I have learned by interoception, which means the stimuli that our own bodies produce. And since you can’t get away from your own body, that can be especially overstimulating. But yeah, it was it was not.

an accident that I wrote a bit about being a highly sensitive person and overwhelmed because that is the number one thing that my highly sensitive people tell me they’re dealing with is just feeling overwhelmed all the time.

Kathi (03:03.863)
Yeah, it’s been so interesting to see your journey on this. And today we’re talking about something a little different, but definitely has some overlap. And that is the link between perfectionism and clutter. And the reason I wanted to bring you on, Cherry, and guys, if you hear little tippy-tappies, I’m just gonna be really honest with you. Moose feels good. She’s going through chemo again, and she feels good for about 90 minutes each day.

Cheri Gregory (03:18.602)

Kathi (03:32.839)
And right now happens to be the 90 minutes while we’re doing a podcast. So you know what? We’re just gonna let it be and be okay with it. And if you’re a long time listener, you’re excited that she’s feeling good for these 90 minutes. And if you’re new, this is just how we roll. So you know what? Right now she kinda does. I will admit, I had Roger bring me dinner and bed.

Cheri Gregory (03:35.15)

Cheri Gregory (03:49.734)
Miss Moose gets to do whatever she wants right now.

Kathi (03:58.915)
so that I could, that’s where she’s most comfortable when she’s feeling her worst. And so I’m not moved. I it’s like waking the baby. That’s not happening in our house. Yeah. So we did something really interesting in Clutter Free for Life, our paid program that has led us to this call. And what we did is we gave everybody who signed up for the Year of our Lord 2024 for the paid program

Cheri Gregory (03:59.679)
I’m gonna go.

Cheri Gregory (04:03.458)
Yeah. 100%.

Cheri Gregory (04:16.492)

Kathi (04:27.483)
a 15 minute coaching call with either me or one of the other coaches, Deanna, Grace, Lisa, or Tanya. And I think I’ve probably had about 30 calls and maybe three of them have not said, well, I struggled with perfectionism. And yeah, talk about, I always knew that there was a connection for a lot of people between perfectionism and clutter.

Cheri Gregory (04:31.576)

Cheri Gregory (04:45.511)

Cheri Gregory (04:50.902)

Kathi (04:54.839)
But I don’t think I realized that the line was straight through as much as it is. And so, of course.

Cheri Gregory (05:00.37)
Yeah, yeah. Okay, so can I ask you a question? Okay, so first of all, kudos that you are obviously such a safe person for people to be confessing that because perfectionism is not something people regularly routinely confess. Like they’ll say, oh, I’m a procrastinator, ha ha, but perfectionism does not have any laugh track behind it. So I’m curious, did they give you examples of what they meant by being a perfectionist?

Kathi (05:11.002)
Oh, yeah.

Kathi (05:16.12)
Right. Yeah.

Kathi (05:22.974)

Cheri Gregory (05:29.342)
or struggling with perfectionism and clutter? What kind of things did they tell you went with that?

Kathi (05:34.723)
It’s the same sentence for everybody. I don’t start because I can’t get it all done.

Cheri Gregory (05:37.652)

Cheri Gregory (05:41.411)
Oh, okay.

Kathi (05:42.739)
Yeah, it is what and I hear that all the time or people will say Kathy 15 minutes as you guys know When we’re talking about decluttering I tell people to declutter for 15 minutes because I feel like our the decider part of our brain Is really good for 15 minutes. Sometimes it’s really good for up to an hour But we’ve all had those days where it’s like i’m cleaning out the garage today And you know in the beginning

Cheri Gregory (05:46.781)

Cheri Gregory (05:51.431)

Cheri Gregory (05:59.323)

Cheri Gregory (06:09.565)

Kathi (06:12.315)
you’re getting so many decisions made and by the end you’re just rearranging clutter. So we had some, it’s almost always I don’t have enough time to do everything so I’m not going to do anything because you know in their brain why even get it started and I say you know you may not notice a ton after 15 minutes I bet you will but you may not notice a bunch after 15 minutes but

Cheri Gregory (06:16.099)
Oh, oh, absolutely.

Cheri Gregory (06:39.222)

Kathi (06:41.923)
After three days of 15 minutes, you are going to notice a difference. But it’s having to get started that I think is really frustrating for people.

Cheri Gregory (06:51.37)
Yeah, yeah. All right, so I am in the midst of reading a book on boundaries and I’ll send you the link to it later, but it says something really interesting at the beginning and here’s a sentence I’m gonna run by you. We can’t master something that’s a continual practice. And let me just adjust that for this conversation. We can’t be perfect at something that we’re always going to be exercising.

Kathi (06:56.888)
Mm. Okay.


Kathi (07:11.751)


Cheri Gregory (07:17.418)
And so what I’m hearing in people who don’t want to get started is they feel like there’s going to be a point when they are completely done. And so if you’re going to ever get to that point where everything is perfect, then you should wait until you have time to do the whole thing and then stand back, sing the hallelujah chorus and enjoy it always being that way. Right. But if we recognize that this is a.

Kathi (07:25.377)

Kathi (07:30.024)

Kathi (07:41.18)
Right. Okay.

Cheri Gregory (07:45.39)
practice, that this is an exercise, this is an ongoing part of our lives, then there is no destination. And that’s part of what we need to take away is the sense that there is a finish line or a done point. And I’m really sorry for those who are listening if that’s super discouraging, but it simply means that as long as you are doing and you know, I push back against the 15 minutes, you know, I’m an overachiever. I’m not.

Kathi (07:46.933)

Kathi (07:51.215)

Kathi (07:54.547)

Kathi (07:59.255)
Mm-hmm. Yes

Kathi (08:04.64)

Kathi (08:11.667)
Yeah, right.

Cheri Gregory (08:13.57)
15 minutes, Kathy, I’m going to do 15 hours, you know? But the practice of doing those 15 minutes is a habit of self stewardship, of taking care of yourself by taking care of the things that belong to you. And like you said, those first few days, you might not notice an awful lot of change, although you know what?

Kathi (08:17.122)
I… Right. Yes.

Kathi (08:29.686)

Cheri Gregory (08:40.17)
I mean there was a time years ago when I injured my back I could only do five minutes at a time and then I had to be on the couch for 55. Let me tell you when I put those blinders on I was able to be pretty darn proud of those of the little bit of space I cleared in five minutes. What do you see, Cathy, what do you see in those who have overcome this sense of I can’t start because I can’t finish it all in the same fell swoop?

Kathi (08:44.77)


Kathi (08:56.683)
Well, and…

Kathi (09:07.187)
Well, I don’t want to say that they don’t believe me, but I think they kind of don’t believe me. And it’s, you don’t know my circumstances, you don’t know my situation, you don’t know who I live with. And so one of the things I’ve been saying to people is our circumstances are different, but our challenges are remarkably the same.

Cheri Gregory (09:14.623)

Cheri Gregory (09:19.246)

Cheri Gregory (09:23.606)

Cheri Gregory (09:36.638)
Yes. Ooh, so good.

Kathi (09:39.291)
Yeah, you know, you know, I love some alliteration. It’s the only way I remember anything. And that, you know, people don’t feel like they’re being helped, which I agree with. And also, it’s not that people, especially adults, in your family should be helping you. This should be a family task, but oftentimes it’s not. And when your mother-in-law comes over, she’s not looking at her son and saying, why haven’t you picked up the house?

Cheri Gregory (09:41.886)
Oh yeah.

Cheri Gregory (10:07.902)

Kathi (10:08.715)
You know, we just know that right and so a lot of people I don’t think You know trust the process because the only results they’ve ever seen have been when they’ve killed themselves To get it. We also Believe in form over function. We believe that if it looks pretty it’s gonna work and

Cheri Gregory (10:22.536)
Mm. Mm-hmm.

Cheri Gregory (10:33.326)

Kathi (10:35.139)
I can get my room looking pretty really quickly, but you know, one of my big things is you can’t organize clutter, because as soon as you touch it again, it’s going to explode, implode, whatever it’s going to be. And so we have to look at the function of a space. And none of us really have a master plan of what

Cheri Gregory (10:38.26)

Cheri Gregory (10:41.42)

Cheri Gregory (10:45.113)


Cheri Gregory (10:53.869)

Cheri Gregory (10:59.392)

Kathi (11:00.671)
We have to make good small decisions over and over and over again to get a space to feel good. And then finally, I think the last thing is we have been sold a bill of goods by these decluttering and organizing systems, magazines, books, that, you know, everybody, it’s clean for a second, it looks nice for a second, it looks organized for a second, and then somebody actually tries to use it. And they don’t take the after picture.

Cheri Gregory (11:05.5)

Cheri Gregory (11:15.85)

Cheri Gregory (11:27.826)
Yeah. Mm hmm. Yeah.

Kathi (11:31.239)
I think those are a lot of the problems. Yeah. Well, so here’s my next question for you, because I know that you have also, you know, you’ve had your struggles with clutter. You and I have talked about those extensively. What do you think some of the misconceptions about clutter and perfectionism are? Because I think, for me, I think the one that I hear,

Cheri Gregory (11:33.174)
Hmm, absolutely. That makes sense.

Cheri Gregory (11:43.414)

Cheri Gregory (11:46.897)

Kathi (11:57.671)
is my mom was a perfectionist and it didn’t look like anybody lived at our house. And that’s their perception. Well, and you had a perfectionistic mom and nobody looked, it didn’t look like anybody looked at your house as a child, right?

Cheri Gregory (12:04.332)

Cheri Gregory (12:08.107)

Cheri Gregory (12:12.33)
Oh no, I mean she literally had white couches and white carpet, but after she passed and we started opening the cupboards, oh my goodness Cathy, she was a hoarder.

Kathi (12:22.003)
Oh, oh, OK, I knew about the closet. I don’t think I knew about the cupboards.

Cheri Gregory (12:25.234)
Yeah. Oh, yeah, everything was absolutely packed to the gills. So it looked perfect. The outward facing looked perfect. But every anything that was behind closed doors was chaos. I was even shocked. But it was all about keeping up the appearances, not necessarily the utility. I mean, putting in white carpet and white couches right as we were producing grandbabies. Come on.

Kathi (12:33.335)

Kathi (12:39.777)
Okay. So.

Kathi (12:53.299)
Right. So I think most people think when they think about perfectionists, they think about a house like your mom or at least what appeared to be your mom’s house. You know, why everything is perfect as soon as you use something it gets put away that kind of thing. But you and I have both experienced the other end of perfectionism and clutter.

Cheri Gregory (12:58.647)

Cheri Gregory (13:03.538)

Cheri Gregory (13:17.474)

Kathi (13:19.551)
You know, what, how has that, how has your idea about perfectionism and clutter changed over the years?

Cheri Gregory (13:27.658)
Well, one of the things that’s really closely connected to perfectionism is procrastination, right? And so one of the things that I have learned that’s been so important, the whole idea of doing 15 minutes at a time has been really important in terms of breaking me away from the all or nothing thinking.

Kathi (13:34.986)

Cheri Gregory (13:49.582)
is that when I used to do those, because you’ve heard me, I’ve called you up before and been like, oh, I’m gutting my office this week, I’m gutting my whatever this week, I’m always using the word gutting, right? But it’s that all or nothing thinking. And one of the things I finally had to realize is that actually my brain and body remembers the way I treat it. And so when I don’t keep it doable for a human brain and body, which is that 15 minute chunk,

Kathi (14:00.066)
Ha ha

Cheri Gregory (14:19.794)
then my body is going to avoid allowing me to do what injured it last time. Because when we do these hours long days long things that kill us like you said because they do they kill our brains they kill our emotions they kill our relationships they are they’re hard on our bodies um what kicks in after that for me is procrastination and I used to think oh I’m being lazy oh I just need to push harder I need to try harder and I finally realized no actually this form of procrastination

Kathi (14:28.034)

Kathi (14:40.369)

Cheri Gregory (14:49.254)
is my body saying, no, we remember how you treated us the last time. We will not let you do to do that to us again. And so I’ve started actually, this is kind of a recent thing for me. I’ve started to actually trust my procrastination a little bit. I don’t mean massively, I just mean, oh, what are you trying to tell me? What memories are you holding on to that maybe I need to learn from? And recognizing that it has this incredibly self-preservation and protective purpose.

Kathi (14:53.019)
Yes, oh, so good. Yeah.

Kathi (15:04.363)
Mm-hmm. Right. Hmm.

Cheri Gregory (15:19.35)
And it’s helped me realize that some of those habits that can cause things to look good. And how many of us before family coming, before a holiday, before a major birthday party, you know, we’re like, okay, we’re all in, we’re going to do that perfectionistic rush of clean everything, spit, polish everything. Oh, by the way, let’s also hand make something and let’s paint something. And, you know, the home improvement kicks in. And then we are

Kathi (15:41.26)

Kathi (15:45.256)

Cheri Gregory (15:47.306)
And for those of us who might be slightly older or have some, you know, have fibromyalgia, or for those of us who are HSPs and our brains and bodies are like, ah, you know, the fact that we used to be able to pull it off when we were 20, doesn’t mean it’s good for us. Doesn’t mean that it has served us well. In fact, you know, I would love to hear from your listeners, Kathy. I would love to challenge your listeners.

Kathi (15:52.575)

Kathi (16:03.219)


Kathi (16:12.983)

Cheri Gregory (16:14.934)
to think about this and then to email you or to reach out to Facebook, whatever, okay? I would love for them to think back to a time that they did that, where at the moment they felt really super proud of themselves, right? Like there’s a high that comes from perfectionism, from pulling it all off, from doing the stash and dash. So everything has been thrown into the back room and everything looks so perfect and they pulled it all off.

Kathi (16:18.711)

Kathi (16:27.862)

Kathi (16:34.728)

Cheri Gregory (16:40.63)
But I’d challenge them to really spend a reflective 10 or 15 minutes thinking about the longer term cost of that. That moment of pride, did it really serve them in the long term? Did it really serve the people that were coming to the house? Did it really serve everybody who lived there? And when I look back at myself, I’m like, wow, that was nuts. Everybody cooperated because I was such a maniac, but the price was way too high.

Kathi (16:48.162)

Kathi (17:08.171)

Well, and I just think about those events, which, oh my goodness, I was the queen of stash and dash. I still work hard before an event, for having a retreat at our house or having a party or something like that, but it doesn’t feel like a massive push for a temporary fix. It feels like we’re actually putting things away

Cheri Gregory (17:36.353)

Kathi (17:40.831)
we’re doing the things that are important, which is really, it’s a big turn in my life. But I also think about how exhausted I was when people finally got there. How, and how I tried to pretend that it wasn’t, that I was just, oh, that this all came naturally. None of it came naturally. I was near death.

Cheri Gregory (17:42.318)

Cheri Gregory (17:53.806)
Hmm. Yes.

Cheri Gregory (18:06.414)

Kathi (18:08.611)
And I wanted people to leave early because I was exhausted. It’s a whole thing. And when we come back, because what we’re gonna do is we’re gonna stop this conversation this week and we’re gonna come back next week. And I wanna talk about, I have some more questions. How do we actually break these habits? And I love what you said about paying attention to the procrastination.

Cheri Gregory (18:31.202)

Kathi (18:36.923)
And as you were talking about, you know, getting ready for company coming over and things like that, all I could think about were the other two points in our book, performanceism and people pleasing. Like we’re trying to make sure that everybody in our family, you know, our moms know that they raised a good girl because their house, the house is clean. We’re trying to make everybody else feel comfortable. Yeah. All those kind of things. And

Cheri Gregory (18:46.85)

Kathi (19:02.519)
how do we break some of those habits? Because no, I don’t want to invite people over to a pit. Let me be very clear. That’s really important to me. But how do we start to deal with the layers so the big push isn’t so big and that we can have, we can not just have people in our house comfortably, but live in our house comfortably. So we’re gonna come back next week. Cheri, this has been a great discussion already.

Cheri Gregory (19:25.337)
Mm, I love it.

Kathi (19:30.539)
but we’re gonna come back with some practical answers in the coming days. Friends, you’ve been listening to Clutter-Free Academy. I’m Cathy Lip. Now, go create the clutter-free life you were always intended to live.

Clutter Free Academy Team

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