Helping a loved one declutter can be challenging, especially when they believe everything they own is valuable. In this episode, professional organizer Stephanie Deininger shares practical strategies for having compassionate and productive conversations about letting go.
With over 20 years of experience, she provides insights into why people hold onto items, how to shift the conversation in a positive direction, and when to call in outside help. Whether assisting a parent, grandparent, or even struggling with personal belongings, these expert-backed tips will make the process easier and more intentional.
In This Episode, We Talk About
- How to lead with curiosity to understand why an item feels valuable.
- Practical ways to shift the focus from keeping everything to making thoughtful choices.
- When to seek professional support, including estate experts or mental health professionals.
Mentioned in This Episode:
- Questions to ask a loved one when they struggle to let go of an item.
- Tips for using estate appraisers and online marketplaces to determine true value.
- How to recognize when decluttering struggles may require professional intervention.
Review full show notes and resources at https://theorganizedflamingo.com/podcast
Review Transcript:
Not everything old is valuable, but try telling that to your loved one who insists on keeping every single dish, book, or piece of furniture. If you've ever felt stuck in a conversation where someone refuses to let go because it's worth something, today's episode is just for you. As a pro organizer for over 20 years, I've had countless conversations where I've seen real progress happen without guilt, frustration, or regret, like all of those things.
It is possible. So today I'm going to share five of the ways that we have seen and have proven to be a good way to navigate these conversations. This is based on our own research, our own conversations and expertise. So whether you're helping a parent, a grandparent, a loved one, a neighbor, a sibling, an aunt, an uncle, a friend.
If you are helping any of these individuals, even struggling maybe with your own belongings, then this episode will be great. These strategies work because they are rooted on compassion, curiosity, and respect, which is three things that we have seen work really well when they're combined together. And they actually help move the process moving forward, and they become very efficient ways of dealing with these types of conversations.
Let's get to the tips. I've got five of them for you today. And what I'm going to do is they're not really necessarily any order. They're just five tips. Some of them you can use by themselves. Some of them, you might have to combine a few of them, depending on the type of person that you're dealing with and you know them best.
So. That is where your common sense will come in, where you get to put your own compassion, like your own personal compassion and personality into this. Um, so again, they're five tips. They're not necessarily meant to be done in that order. This isn't a step by step. This is more of five things that we have seen work really well when they're used in conversation.
So let's get to it.
Welcome to the Organize and Cherish podcast with The Organized Flamingo. I am your host, Stephanie, your compassionate and efficient professional organizer. Whether you are part of the sandwich generation, helping a loved one declutter or just trying to simplify life, this is the place for you. Together, we will tackle those overwhelming piles of stuff, uncover purpose in what we keep, And let go with dignity and care, because it's not just about throwing everything away.
It's about respecting memories and simplifying life. Sound like a plan? Let's jump in and get organized. Okay, let's start off with, truly, I know I said that they're not in order. I would say this is probably my number one tip in general when you are helping someone else declutter, downsize, and or organize.
So instead of making this about you, this is going to be about them. So the tip number one really is lead with curiosity. Instead of shutting down the conversation with you don't need this or this isn't worth anything because you're trying to make it quote unquote easier for them, right? Like decision fatigue and you're just trying to move things along.
You might have the best intentions. But that does not, it's not really helpful for someone who doesn't know and hasn't been able to downsize on their own or declutter on their own. So try leading with curiosity. Some of the things that you could be saying are things like, tell me about this piece. What makes it special to you?
We I ask this question all the time. Um, another way to say this is I love to hear the story behind this. Where did it come from? What do you love most about this item? This is when you're coming to a roadblock. I'm not saying ask this question for every single little tiny item, okay? We're not asking about every single rubber band in a junk drawer, every single stamp, every single thing, small or big.
I'm talking about whenever your loved one or the person you're taking care of is having a hard time letting go and there just seems to be a roadblock. Maybe there are more maybes than there are nos or yeses or definite answers. So that's when these curiosity led questions will help you understand a little bit more.
And it works because this shifts the conversation from defensiveness to storytelling, which is really what we want. We want to move away from that, why are you making me do this mentality, the defensiveness. It's like. You're calling me this or, or being judged. You're trying to move forward into tell me more so that you can get to the root of the problem and, or we can move past that and start Dissecting the why and then go from there and almost like, it's almost like that problem solving now we create from this really big roadblock of defensiveness, then we start dealing with smaller problem solving type of questions that we can easily get to instead of trying to deal with like this really big trauma or big, um, heavy feeling of defensiveness.
So many times people just want to feel like they were heard. They just want to know that they're being understood, that the story could be passed on, told, and maybe they can move on. You may even discover something meaningful about an item that helps you both decide what to do with it. This is really important and really helpful for those of you who You might want to keep some of the things for like a family heirloom.
So this will help you not have to hold on to everything. Because if you are similar to the person you're helping where it's hard for you to make no decisions because sometimes some of you are very good at helping others. But when it comes to trying to figure out what to keep for yourself, you have a hard time.
So when you're asking these questions, this will help you. In your own downsizing and figuring out what to keep and what not to keep as they're passing it on to you. So it works both ways. There is, I'll give you an example of a couple of ways that this has, um, come to life as I was, you know, I journal through, you know, throughout my career and I never really talk about people in particular, like the, the specific people.
I talk more about the instances so that I can learn from some of these experiences. But I once worked with a, a woman whose dad had. A whole pile of old cameras. Some vintage, some not. I'm talking even the recyclable, one time use type of cameras. I mean, all kinds. And then he also had the, you know, more heavier cameras.
He had a lot of them. And he would, they weren't all his. He would collect them as well. So instead of pushing to declutter right away, I asked about them. I asked both about the stories behind what was behind the collection. And it turns out that it all really started with a handful, like just a couple of the cameras and the rest of them were now collectibles because he really enjoyed cameras.
I mean, it was just like a hobby, right? Like sometimes we collect things along the way that we really like and people give them to you. And then now you've, now you have a lot of them. What it came down to is that there were really only a handful of special ones. So that helped us narrow down the fact that we did have to keep them all, that this was a very special collection.
We took a picture, but the valuable ones were only a handful and the rest we were able to give away. We checked and make sure that the film wasn't inside of them. And then there's only a few that had film at that time. So we developed those. Got the pictures back and then the rest we, they weren't worth very much because we were able to look up and ask someone to help us see if they were worth anything and they weren't worth anything so we gave them away, we donated them and or threw them away if they were the one time use cameras.
And then we kept only, there was just a small box of them so that they could decide if they wanted to sell or what they wanted to do going forward. So, that question alone, it, it might. I feel like it takes a long time to hear the story, but sometimes listening to the story will get you to a much quicker place.
and more definitive place than having to hurt someone's feelings and then maybe throw something that you didn't mean to throw away. So lead with curiosity is one of my, you know, one of my biggest steps. Let's head on over to our second tip, which is to bring in a neutral third party. Sometimes hearing it from someone else makes all of the difference.
So who are some of those people that could help? There's estate sale professionals, there's antique appraisers, there's collectors. Um, even tools like eBay, eBay, you can also use like a tool that can help you like a book or an online like an eBay sold listings or Facebook marketplace because you can see the historical transactions of some items.
So then you can see how much things sold for. Um, but then we, you know, we start leveling, you start going up from there. Like some of those are just very simple tools, but then as you move up the ladder. Then you can start asking professionals, hire an appraiser, and then moving on from that order. You know, some of the things that you can be saying to introduce this to someone is I know this means a lot to you.
How about we check what it's actually worth? What do you think? Another way is, would it be helpful to have an expert give us some insight on what people are paying for this? Because sometimes it takes you out of the role of the bad guy or the bad woman, person, you know. It takes you away from having to Be the, the, the person who knows it all.
Even if you do know, the perception can be, Oh wow, you're just, you're just so perfect. You know, you, they get defensive, like you're just so perfect and you know it all. And now there's this friction. So it takes you out of that equation and from you being the, the bad person, the judgmental person in this scenario.
So if an expert says. This China set is in selling, it's so much easier to accept it than to hear it from a loved one, like a family, from you or for someone else, because, like, again, there's just less judgment. You as a person, as a loved one, have probably seen that individual in many different places in life.
And so the person hearing it that you're helping might get defensive over the fact that You might be seeing them as, you know, not taking this serious or that you're judging them and nobody wants to feel that way. So when you add a third party, it might help with that. Look at the prices together too. I mean, this could be a total open conversation.
It could be really fun. This keeps it collaborative and not combative. Now, again, we don't want to be nitpicking. Okay, this is, we're talking about. When they're coming to a roadblock, so if you are seeing that they're having a hard time with a category that's really large, like clothing, clothing is a big one, people tend to accumulate a lot of clothing because they were in different phases of their life, you know, different looks, different feelings, different body types that they went through, so some of it becomes very nostalgic, some of it becomes guilt, some of it becomes that You know, it's been a hard transition to go back and forth, depending, you know, for like weight and personalities and things like that.
So I guess someone was married and then they maybe got a divorce and then they were just in a different place in their life or maybe they had kids and then when they didn't have kids, um, again, weight is another one, self reflection is a big one. And so when they go through a lot of those phases with clothing, that tends to accumulate.
And so if you have a big category like that, look up their style and see what it's selling for. So if this person was really into jeans and they have, you know, a hundred pair of jeans, look up jeans like your jeans reseller and see the ones that are worth the most so that you don't have to go one by one.
Like you don't, you're not looking up every single pair of jean and brand. So try to be as efficient as possible by grouping categories together. Another, then our next step here is to shift the focus to usefulness. If it's truly valuable, should someone be using it? That is a golden question to ask yourself, to ask themselves.
Some of the things you could be saying are, if this is valuable, what do you want to do with it? So if you don't want to get rid of it, what are your plans for this? I'm just curious. Another way to say this would be, would you like to display it, use it, or is it just sitting in storage? Like, help me with what you would like to see done with this thing.
If it's worth something, would you like to sell it or donate it to someone who can enjoy it? So the reason why these types of questions work to shift the focus to usefulness is because it moves the conversation from keeping versus letting go to making an active decision. So now you are seeing and visualizing who is actually going to use this thing, whether it's It's the person that you're helping with, or they can finally visualize the other recipient if they were to sell it or donate it.
It reminds them that items sitting in storage are not being appreciated or used. So it really gives them that perspective of, Oh my gosh, you're right, it's not being used. If they aren't ready to part with it yet, they may at least consider repurposing it or displaying it. So this gives it. the action where it comes out of the box and it no longer just sits there.
So that's one of the reasons this is really helpful. For a while we had, I had a client who had an attic full of, you know, vintage teacups, like tea sets. She really loved doing these and actually for a while she would rent them out to weddings and events and, you know, parties and baby showers and bridal showers and birthday parties and everything from, uh, like Valentine's Day type of parties for Galentine's.
Anyway, so she had a lot of those for a while, but then she also was a collector, so it kind of served both purposes and it actually, you know, ended up making her a little bit of money. So in her mind, it was, this isn't trash and I'm not donating it and it's obviously worth something. But she was ready to move on and when she did move on and actually ended up helping her and then eventually her children when she moved, when she downsized.
And then, you know, her kids were saying, I love this stuff, but there's just so many and I don't have that same desire to rent them out and have these parties like she did. So I ended up helping both scenarios once they were inherited and then before they were inherited. But instead of keeping them all boxed up, she chose one special set of display, which she took with her to her new place.
And the rest of it, she told her children. You know, here they are. It's up to you what you want to do with them. And then eventually I ended up helping their kids figure out what to do with them. It was this realization that there's someone else that could be using this. Someone else that maybe could be running a small little business with these, the way that she did.
And so she could, she could really visualize that. We did document them by taking pictures, so she did have pictures of that. And she also had pictures of the events. That, uh, where these items were, the teacups and tea sets were used. So she had that. We made a book, like a little memory book, and then we called it a day.
So that ended up being the solution for that. Hi cherished friends. Life can get overwhelming, especially when you're juggling caregiving, clutter, and everything in between. That's why I created the Organize and Cherish Weekly Email that goes out every Wednesday straight to your inbox. to help you keep the momentum, inspiration going with tips and reminders of our upcoming events.
All you have to do is head on over to organizeandcherish. com and sign up for the email newsletter. It's free and you can subscribe whenever you'd like. It's my way of helping you simplify your life and respecting memories along the way. Now back to our show. Tip number four is to create a memory preservation plan, which is.
What I just sort of talked about because people often keep things because they fear losing the memory associated with them. So just like the client I just mentioned before, we did create a book with it. We took some pictures, sent it off to a photo album making place, and it was there within a week and she had the book and the memory was kept alive.
Some of the things to say here that if you think that this is the kind of the problem or the roadblock is. I love that this reminds you of grandma or, you know, your aunt or your sister or your brother. How can we keep that memory alive in a way that doesn't take up so much space? So asking them and seeing if they come up with an answer because they might already have something in mind.
Another way you could word this would be, would you like to take a photo of it or keep just one piece instead of the whole collection. So give them some options that they can pick from, but all of them being efficient and a way of letting go. So another way is, you know, like giving them a solution like, can we do this together as a family or as friends?
Like, hey, what do you think about all of us getting together and creating some memory books with about these items? Um, if it's something small like stamps or coins, you know, you can make a book out of it. Keep the ones you like, take some pictures, maybe make a slideshow out of it if you're more of a virtual picture person, video person.
So create a, an event out of making this a memory. And it's almost like the storytelling piece. creating something that's more efficient and not, does not take as much room. Some of the ideas, like I said, it's like taking the pictures, keep one representative item, and or create some kind of scrapbook that could be digital.
It could be also physical, but if you're trying to avoid having more physical stuff, then you probably want to go the digital route. You can also level this way up and hire a storyteller, a professional videographer. Or picture or photographer that is in the business for, of taking pictures for memories.
And actually, I have a quick example for this. I used to deal with more paper in the past, not so much anymore, but, um, this one client very specifically hired us to deal with old letters. And we, and as a side note, another little side note here, I used to work for a company that had its archive library. It was a title company many moons ago.
And I was, I had a project with them to digitize all of their old archives they wanted to keep in their library. And so I'm very familiar with. You know, dealing with paper and archiving and whatnot, but instead of keeping them all, what we've done is scanned the most important ones and created a printed book to pass down.
Same thing with the really big libraries. This is where, you know, you pick the one that's like a representative of the idea or the story you want to tell and, you know, and then kind of get rid of the rest. Now, if you're trying to build a library and a professional archive library, this is a full on project.
We can have a conversation about this on a separate note. If that is what you're trying to achieve, which is to preserve the memory, have it be a collaborative project, event, family gathering, friends, and, and make something out of that. Okay, let's talk about our last tip here, which is to offer a let's pick a few items approach.
Okay, so if they aren't ready to let go of everything, meet them halfway. This is a really important thing to remember, that not everything has to be keep or let go, keep or let go, keep or let go. If you're in a predicament of time, okay, because I understand that some of you have to get rid of stuff, like you have to make some movement.
Sooner versus later, because you have a deadline, they have to move out, mortgages are due, or they have to move to their new place, and like there's just a lot of transition parts here and time is of the essence. So I understand that, but if you can meet them halfway, you might move much quicker with less friction than if you were to try to force them to do something they're not ready to do.
So some of the things you could be saying here are, would you be open to picking a few special pieces and finding a new home for the rest? These are the types of questions where I know we talked about, you know, having them almost visualize where it would go, but this is more of giving them the two options.
Hey, can we pick one or two and the rest we let go? Like there is no middle, let's store it. This is all about. You know, let's, let's finally make a decision to let it go. Another halfway is maybe not always having to pick one. So maybe saying like a different special number. I'm using five because it's five usually ten, like five to seven seems to be a good number that doesn't overwhelm people.
So if we could keep five to seven of the most meaningful pieces, which ones would they be? Um, anything below ten seems to be like a magic number where people feel like. Okay, I'm still keeping enough, but it's not so much that it defeats the whole purpose of trying to let go of things, right? And then the other way you could say this is, if we keep one, gifted one, and sold or donated the rest, which ones would it be?
So just using a different word to have them pick a few. Okay, so this is that, that really is what the tip here is. It's just giving them their own options, but with a limited With a limited, uh, number, so you've kind of already giving them the max amount of number of things they can keep, but having them still be able to, to have choices so that you're not making the ultimate decision for them, because this avoids an all or nothing mindset.
Big friction point here for people. When you hear that you have to get rid of everything, that immediately shuts people down. One of the reasons people don't hire us is because, and then when they finally do, they'll come back and say, I just felt like you were going to make me, force me to get rid of everything.
Um, so it's not about keeping or getting rid of everything. It's somewhere in the middle. And it helps them prioritize the most meaningful items as well, just for their, their own sake. While releasing the less important in a, just in a different verbiage. And once they let go of a few things, they may feel ready to let go of more.
I've talked about this in the past. I've had, um, other podcast episodes about this where You, when you practice the small, the small actions of decluttering and downsizing, it allows you to practice that executive function that some of us struggle with. And then the more you do it, the easier it will get.
Now I want to add a bonus tip here, and this is more of a disclaimer or a PSA, like a public service announcement, when it's time to call in a professional. So while these five tips help in day to day decluttering conversations. Sometimes, a deeper issue is at play. Here are some of the signs that it's time to call in a therapist, a mediator or a mental health professional.
You know, extreme emotional reaction. So like there's anger, there's a lot of deep sadness or anxiety over small decisions. Definitely time to call a professional because dealing it with yourself will only frustrate you, your loved ones, and everyone involved. There's an ongoing conflict. If every conversation about stuff turns into an argument, it might be time to get some help.
For both of you, so that you, there is that middle person I talked about, um, having someone like a third party, but sometimes you need to elevate it to someone that specifically can mediate this conversation. There's the paralysis or hoarding behaviors. If someone can't make any decisions at all, it might be time to call a professional because hoarding is a mental health disorder that needs professional help.
And I don't want you to have to deal with it on your own, feeling like You, you're not making any progress, like they, you can't get through, through to them. It's frustrating. They might actually need a little, a boost of someone who can help them navigate through this disorder and not be so frustrating on everyone involved.
And you know, strained relationships, if this is impacting family dynamics in a serious way, don't let stuff get in the way of that relationship. Have and ask for some help. that can help you navigate through all this so that you don't have to let your relationship with this person be so conflicted that there's no way to come back from it.
Like you don't want stuff, physical stuff, to be the reason that you all have strained relationships. So if you're starting to feel that way, definitely get a little bit of help. If you're trying to figure out how to word this to them, here are some ways that you can And you can say something like, Hey, I love you.
And I want to make sure we're handling this in a way that feels supportive. Would you be open to talking to someone who specializes in this? Another way it could be, it seems like this process is bringing up a lot of emotions. Maybe having a professional guide could help. What do you think? You know, some of the people that can be help, very helpful with this, our family therapist, geriatric care specialist.
This is for older loved ones struggling with transition. very specific to more of our aging family members and community. And then, of course, we've got professional organizers like ourselves, but more specific that deal with chronic disorganization or hoarding, because those are very specific. And if you need any help with that, I'm certainly happy to guide you towards, um, some great resources.
We also have our conversation action cards. So if you need some more ideas on what to do or what to say when you're dealing with these hard conversations, head on down to our show notes and, um, you can get them in our resources page as well. So, you know, don't forget that there is help that you can be getting.
So remember, as a quick little recap here, it's not just about decluttering. It's about helping your loved one make thoughtful decisions with compassion. And it's the thoughtfulness that will stick because you want less friction, you want efficiency, you want to move forward, but you don't want to end up being mad at each other and having this be a friction point for your relationship.
Okay, that's, but you do have to make some decisions like faster, sooner than later. So we want to somewhere balance those two. Okay, so the quick five tips here were the lead with curiosity. So let them share the story. Bring in a neutral third party. Let an expert give perspective. This actually, you know, a third other third party here is a therapist.
A men, a mentor, a mediator, anybody that's a third party, another, another family member or friend that you both trust, that is also a third party. Uh, number three is shift the focus to usefulness. So is it being used or just stored? Like pose the question in that way so they can see the bigger picture.
Four, preserve the memory in a new way and involve others. So make things that are extra special and lets them move on from the memory that, from the past. Like have them make new memories with this item, combine the two and move forward. And then the faithest to pick a few special pieces. So ver, worded, do the verbiage so that the, the mission here is to keep the best and release the rest, but worded in a way that you have given them some boundaries, but they feel empowered to also pick the ones that they want to keep and not feel like it's an all or nothing.
So I hope that these strategies work in your everyday situations, but if emotional emotions are running high, it's okay to ask for help. So don't forget about that. And remember that the goal isn't to get rid of everything. It's to make intentional, thoughtful choices. You don't have to do this alone. We are here to help.
And if you found this helpful, don't forget to share this with a loved one. And until next week, happy organizing. Thank you for listening to the Organize and Cherish podcast with The Organized Flamingo. If you enjoyed today's episode, I'd be so grateful if you left a rating and review on your favorite podcast player.
It helps others discover our show. For full show notes, resources, and more organizing inspiration, visit www.theorganizedflamingo.com/podcast. Until next time, happy organizing.
