In this episode, we explore why getting organized often has less to do with stuff—and more to do with the questions we’re asking ourselves. Whether it's searching on Google, using ChatGPT, or trying to help a loved one decide what to keep, progress depends on how we frame the problem. We talk about the subtle power of shifting from judgment-based questions to curiosity-led ones, and how asking better questions can unlock momentum in our organizing, decluttering, and downsizing journeys.
In this episode, we talk about:
- Why vague or emotionally loaded questions can keep us stuck
- How search engines and AI tools like ChatGPT reflect the power of well-worded questions
- A practical framework to rephrase common organizing questions for better clarity and action
Mentioned in this episode:
- A “Question Makeover” cheat sheet for reframing stuck points during organizing
- Real-world examples of how better questions lead to faster decluttering decisions
- A free download: Better Questions to Ask When You’re Stuck
Review full show notes and resources at https://theorganizedflamingo.com/podcast
Review Transcript:
Hey everyone. Welcome back to Organiz and Cherish. I'm Stephanie, and today's topic is one that I've been thinking about a lot. So much so that we did an episode semi-related to it. Yes, but not really. And then this popped up a couple of weeks ago and I'll talk about it in just a second, and then it came up again when I talked to a client and then I talked about it in our email newsletter.
So it's definitely popping up in a lot of places, and it came up recently also when I was using ai, which is artificial intelligence. If you're not familiar, and it's the new technology, I guess you can say, it's a really powerful search engine. But honestly, I've seen it pop up in so many places lately from conversations with clients just in general to the Google searches that I do and that I help with with other families.
So here's the question and the topic. Are you asking the right question? Because when you don't, things stall and you don't get the results that you want, and the results don't land. And then frustration builds. I've seen this happen not just with organizing projects, but in life, business and parenting, et cetera, right?
So today we're unpacking the power of asking the right question, very specifically when it comes to organizing, decluttering, downsizing, and making decisions with stuff. Because when you don't have the right question, then either you will stall. It's almost like a big bump that doesn't allow you to get over the hill, or it makes it really hard and stressful, or you abandon the project altogether.
We don't want any of that, right? We want to make progress and we want to take action, like actual actionable action that you're, you're seeing the progress, like you're doing the thing, you're helping your loved one, they're making progress and or yourself, so. It all kind of boils down. It all comes back to, are you asking the right question?
Welcome to the Organized and Cherished podcast with the Organized Flamingo. I am your host Stephanie, your compassionate and deficient 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. So here's what I've noticed.
Many of us aren't stuck because we're lazy. We're stuck because we don't know what to ask, and if we don't know what to ask, we don't know where to go or what to do or what to even aim for. This happens in organizing all the time. Someone will say, where do I start? I either have seen it, you know, on social media, or people will just say like, where do I start?
Or when they meet with us, they'll say, I don't know where to start, like, where do, where do I even begin? But that's not quite the right question that I would suggest. You ask yourself if you're feeling overwhelmed and there's no one there to guide you. To get to the right question because if you're listening to the podcast, you might be doing it yourself, and I've got some tips for you on what the right and or more helpful questions could be so that you don't feel stuck, and hopefully you can get yourself out of being stuck.
Okay. Or your loved one. So the better one might be the, the better question to that might be, what do I want this space to do for me right now? Or you could say whatever the timeline is. If you, you have something specific like, what do I want this space to do for me in a year or, or a month or whatever. It shifts the focus from the overwhelming everything to a clear, meaningful intention.
So instead of, you know, being a kid in a candy store where you are overwhelmed with all of the options, and now it's just so you don't even know where to pick or start. And when we were a kid, it was a happy memory, maybe because I have all the candy in the world. But as you get older, all of those options and those big eyes can feel overwhelming with life because now you've got.
A big task ahead of you in addition to just everyday life, and that is where the overwhelm starts to come in. Even when we have tools like chat, GBT or Google Gemini, or even Pinterest, whatever the tool, whether it's AI related, like a search engine, it's helping like a learning model like chat, GBT, like we talked about in, in a few episodes ago.
Or you're doing a Google search or you're using Pinterest. The outcome really depends on what you ask. Asking the right question is the difference between wondering around the internet and actually making progress. It's the difference between you asking yourself, well, what you know, where should I even start?
And just aimlessly starting with that one drawer that you think is the easiest or the one closet, and taking everything out and being so overwhelmed that you started a project with zero goals. That now you are in a worse place than before because now you have to clean up the mess and you didn't even get to downsize, declutter, or organize or make it functional.
So how do we learn to ask questions? You know, in school or academia, there's a big emphasis on forming good research questions. So if you're an academia person or your teacher, you know this all, all too well. But in day-to-day life, that skill doesn't always carry over. Why? Because in real life. It's a little messier.
Emotions get involved. Time runs short. We start saying things like, I just need to get rid of stuff instead of asking which items here support the life I'm building. And sometimes we don't ask because we're afraid of the answer. I've noticed that quite a bit with many of our clients. It's almost like if they ask, why am I keeping this?
It might unearth a memory that they're not ready to deal with. Or the realization that they've been putting something off for a while and that's okay. That's part of the process. I mean, I go through this, I got those questions are great for me, but the magic is here, or one of the magic pieces are here.
Even if you're not ready to act, asking the right question plants that seed and it softens the resistance, like it makes it more manageable and it starts allowing you to be real and honest. So let's talk about some search engines and AI for a second, because right now in our era, you know, this is a recording from 2025, but learning models, artificial intelligence, just asking questions or just getting information is much easier right now and it's giving us answers and it's guiding us through it and now has a personality.
So it's just so much easier. To find information that we otherwise, otherwise would have been a lot more difficult. So Google has trained us to ask questions, right? Because that's really kind of the history for us as the regular folk, if you will, of search engines. Google just dominated that space forever.
They've trained us to ask the questions that when you start typing and it says, did you mean, or it auto completes it for you? So it started training you. It's been around for a really long time. Learning models, artificial intelligence. All of these search models that are very advanced are, are now easily accessible to us like Cha, GBT, and Gemini.
These models have been around for a long time. It's just that we either were not aware that we were using them or they were stripped down to the very basics so that we did not feel overwhelmed. Like the Google search engine. Right. It filters based on your wording. The more specific that you are, the better the results.
So it slowly but surely has been trying to train us to do good questions, but at the end of the day, it filled out the blank. It filled it out for you, so you didn't really have to think because it made it easy. Now with all of these new Chacha, Petit, and Geminis of this new era, these tools don't just respond.
They adapt to your questions, but they still depend on your input. Hi, cherish friends. Life can get overwhelming, especially when you're juggling caregiving, clutter and everything in between. That's why I created the Organizing 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 organize and cherish.com and sign up for the email newsletter. It's free and you can up 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. So a, a couple of examples are like, if I ask chat d PT now help me organize my house. Well, that's vague, but if I say help me organize my garage that has camping gear, tools, and old paint cans, I have one weekend to work with. Now we're getting somewhere. Now it's specific in the question directs the strategy.
When you ask something very generic, I'm sure if you are using any of these models like a lot of our community members are, and that's why we're diving in there with you. Okay, we're we get it. This is a very easy tool to use. We want to make sure that you use it to its full capacity and that it works for you and it doesn't make it more problematic like your, your space or your projects aren't more problematic just because now you are, you are asking it all these questions and it's giving you these tasks and ideas, and now it's just.
Another Pinterest board that you're never going to get to because you talk, you talk to this chat, DPT Gemini, whatever you use, and it's talking back and you think you have a plan. I ha I did a whole post about this, right? In a whole, actually the, our AI conversation a few episodes ago. I. Was all about that.
Like are you just collecting more digital notebooks and ideas and Pinterest and magazine clippings like you used to, but you're not actually taking steps and now because you are asking it specific question or not specific questions and it's guiding you through and seeing what, what it is that you mean.
Now you are just talking to a virtual friend, but you're not taking action. Again, give it specific question, a specific action. Then we're getting somewhere. Now it starts to give you more of, okay, based on what you told me, this is what I, you know, the plan, like the actionable plan. So that's why the question directs the strategy and we, I don't want that to be missed.
Now, if you're not using all of these AI tools, the same applies. Asking a specific question will get you specific details and much easier to handle in smaller bites, actionable steps. So let's go deeper. One of the ways that I help people move forward, whether it's with a junk drawer or a storage unit, is by reframing their questions.
And again, whether you're a digital user or not, these types of cheat sheets that I use will be helpful. So you can, if you're using the the Gemini's Chat, GPT learning models, feel free to use these as prompts to help you in your organizing dec cluttering and downsizing journey. If you're not, you're not comfortable, you're not there yet, you don't want to, then these are still helpful for you to be asking yourself and or your loved ones just in real life, everyday actions.
Okay. So like, instead of asking where do I start, ask what do I want this space to do for me right now? And you could insert the timeline that you need or want instead of the right. Now another question that I, I have seen people ask a lot is, should I keep this? Well, I mean, there's so many ways we can answer that.
I, I don't know, should you so ask this instead, what would make this worth keeping? Another question that comes up a lot is, is this trash? Instead, you could be asking, could this item serve someone else if I'm not using it? That is, especially those questions important, are important. If you are a giver, if you're looking for the right person to pass this onto, super helpful, why can't I get this done?
And another way to ask that is, what's the smallest step I can take so that you can get it done? So see how the question just becomes more actionable. So these kinds of shifts change the tone of the subject. They invite curiosity instead of cri criticism, which is super important in moving forward for you and or a loved one, they move us towards solutions that actually fit our lives, not someone else's vision of Heidi.
So if you're helping a loved one declutter, this works, like I said, you know, just as well. Um, but there's also the element of being curious to get the story from them in a much more efficient manner. So, for instance, I. You can be asking something like, what story does this piece tell? Or would you feel okay letting this go if we took a photo or shared the me memory another way.
So it's kind of like, how do I reframe the question so that it can be helpful, which is the power of the question. And remember, we all, we have our in a free, uh, resources corner over on our website. We have questions for that you could be asking you and or your loved one in a more compassionate way. To move your project forward, to actually start making progress, to start decluttering, to start downsizing in a way that feels good, it's efficient, it's meaningful, and again, you, you are actually taking action.
Let's do a quick reality check because not every question is helpful. Some questions keep us stuck. So for example, why am I such a mess? Why? Judgment is disguised as inquiry right there. Not helpful at all. Those kinds of questions pull you away from action, but here's how to flip it. If a question feels heavy, flip it as if you were helping a friend.
So instead of saying, why can't I make any decisions, ask yourself what decisions feel easiest to make today. Small shift, big impact. I do this with our weekly clients quite a bit. We do immediate nos. When I can sense or feel, or they tell me that they're overwhelmed with decisions, they don't know where to start.
If I can feel or see or hear them saying, where should I start? I don't know where to start. We immediately go towards, okay, no worries. Let's go to the easiest space or easiest area, or things. You can make a decision on right now that feel, that feels good, that's easy. Like immediate nos. Usually, you know, a pantry or the areas where there's a lot you can take out that's like empty bins.
Empty boxes, expired food, like really expired food, not just like from two months ago. Those are just immediate nos. So we can get through that and build momentum. So as you head into the rest of your week, I want you to try this. Pick one area you've been avoiding. Like your entryway, maybe a closet, a paper pile.
Those are, those are big. Write down three new questions about it. Choose one and let that be your guide. Not the whole task, just the better question. So if you want help coming up with organizing questions that actually move you forward, I've got, you know, the quick download for you that is attached to this episode in the show notes called Better Questions to Ask When You're stuck.
Totally free. Totally helpful. These better questions to ask when you're stuck can also be put in your chat GPT model. If you're, you're, you're in the tech world now, like you, you are moving forward with all of these friend chat, chatty G friends, um, or Gemini. Okay? So feel free to get the questions and put it in, in your learning model so that they can start to guide the, the model towards how you want to start asking questions to move your project forward because you don't.
Need the perfect answer. You just need the right question to get unstuck to move it forward. Alright, let me know if this is helpful. How's it going? Do some check-ins with me. I always love to hear and cheer you on on whatever project you're working on. Alright, until next time, happy organizing. Thank you for listening to the Organized and Cherish podcast with the Organized Flamingo.
If you enjoy 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.