
Beyond the Sessions is answering YOUR parenting questions! In this episode Dr. Emily Upshur and I talk about…
- Why cleanup time can be surprisingly hard for young children.
- What’s really happening in your toddler’s brain and body when they are resisting transitions.
- Is repeating yourself over and over again a normal part of parenting young kids? And how do you know when it’s part of the learning process versus something that needs a different approach?
- How motor planning, executive functioning, and task initiation can make something like “clean up your toys” feel overwhelming to a child.
- Why you might still be doing 90% of the cleanup work at this age (and why that can actually be part of the learning process.)
- Practical strategies to make cleanup easier, including breaking tasks into smaller steps, planning ahead for transitions, and using cues like songs and routines.
- How to shift your expectations so you can stay calm and connected instead of getting pulled into power struggles.
If you find yourself repeating the same requests over and over while trying to stay patient and regulated, this episode will help you understand what’s developmentally normal for young children and give you practical tools to make cleanup time and transitions feel more manageable for both you and your child.
REFERENCES AND RELATED RESOURCES:
👉 Want extra support in your parenting journey? Upshur Bren Psychology Group offers therapy and coaching to give parents the tools to feel more grounded and confident as they navigate parenthood and learn how to most effectively support their child. Visit upshurbren.com to explore our services and schedule a free 30-minute consultation call to find the support that’s right for your family.
💥 Tired of constant battles with your child? Watch my ✨FREE✨ workshop, Overcoming Power Struggles, where I’ll teach you the exact strategies I use in my clinical practice to help parents break free from the cycle of yelling, threats, and negotiations—and instead foster cooperation, connection, and calm. Just visit drsarahbren.com/powerstruggles to get instant access to this workshop.
LEARN MORE ABOUT US:
- Learn more about Dr. Sarah Bren on her website and by following @drsarahbren on Instagram
- Learn more about Dr. Emily Upshur on to her website
ADDITIONAL PODCAST EPISODES YOU MAY LIKE:
🎧 209. How can I get my toddler to share and play nicely with other kids?
🎧231. BTS: How can I build my toddler’s assertiveness skills?
Click here to read the full transcript

Dr. Sarah Bren (00:02):
Ever wonder what psychologists moms talk about when we get together, whether we’re consulting one another about a challenging case or one of our own kids, or just leaning on each other when parenting feels hard, because trust me, even when we do this for a living, it’s still hard. Joining me each week in these special Thursday shows are two of my closest friends, both moms, both psychologists, they’re the people I call when I need a sounding board. These are our unfiltered answers to your parenting questions. We’re letting you in on the conversations the three of us usually have behind closed doors. This is Securely Attached: Beyond the Sessions.
(00:41):
Hello, welcome back to the Beyond the Sessions segment of the Securely Attached podcast, where we answer listener questions, and I have Dr. Emily Upshur here to help distribute her wisdom. Hi, Emily.
Dr. Emily Upshur (00:56):
Hey.
Dr. Sarah Bren (00:57):
How are you?
Dr. Emily Upshur (00:58):
I like being wise. Thank you.
Dr. Sarah Bren (01:00):
You are. You are so wise. I mean, that’s how this whole thing started, was you and me and Rebecca Hirschberg, who also comes on to answer listener questions, we always call each other and text each other and we’re like, “What do I do when this is happening?” Sometimes you just got to crowdsource your mom wisdom.That is what we’re going to do today.
Dr. Emily Upshur (01:22):
Let’s do it.
Dr. Sarah Bren (01:23):
So this mom wrote in. She’s delightful. I’m going to try to capture her flair in the way she speaks as she typed this question. So she writes, “Hey, love, love the podcast. I listen to plenty of parenting podcasts and this is by far my favorite. My question is as follows. I’m finding lately with my three and a half year old who really has an amazing, calm, easygoing nature, that certain things I have to repeat over and over. And I find myself constantly trying to hold myself back from threatening. For example, come on girl, we got to clean up the memory cards.” And she’s like, “Nah, I can’t.” And I’m like, “Yeah, but we got to do it now. And then it’s bath time, et cetera.” And she’s like, “So let’s just take a bath.” And I’m like, “No, sweetie. We got to clean up your memory cards right now.” And I’m literally taking deep breaths in and out trying to regulate myself because at the tip of my tongue is like, if you don’t clean up your toys, you aren’t getting dessert tonight.
(02:25):
And I know that’s wrong and I don’t want to go down that rabbit hole. She really generally listens and is super cooperative. It’s just with certain things that are hard or she has no patience for. For example, cleanup. She really struggles with motor planning. She gets very stubborn and refuses. She is getting OT to help with the motor planning and I do offer support in the cleanup, but then I basically do it all while she picks up maybe three pieces. Any advice? Thanks guys.
Dr. Emily Upshur (02:52):
Aw, she has such nice insight into the motor planning and cleanup being hard. I love that.
Dr. Sarah Bren (02:57):
Yes. Yes. And I love the examples because she like narrates her inner thoughts and I’m like, “I have those exact same inner thoughts.” And I’m literally trying to present this sort of calm, reasonable, warm mom energy, but on the inside I’m like, “God, it would be so much easier if you would just do it the way I would like you to do it. ” And so her awareness of like, yeah, these two experiences are having simultaneously for me as mom, is just so insightful and articulate and relatable. This is such a frustrating response, but I kind of feel like you’re doing exactly what I would recommend you doing. You know what I mean?
Dr. Emily Upshur (03:51):
Yeah.
Dr. Sarah Bren (03:52):
I almost think it’s the expectation that it shouldn’t look like this or it should be different that’s getting in her way rather than the intervention.
Dr. Emily Upshur (04:05):
Right. It’s like expect the pushback, right?
Dr. Sarah Bren (04:07):
Yeah. The pushback and expect that at three and a half teaching how to clean up your toys and setting that expectation that this is what we do after playtime and that this is something that you’re responsible for might look like I do 97% of the cleanup and you do that last 3% and I give you a super big high five and say, “You crossed that finish line. Look what you’ve done.”
Dr. Emily Upshur (04:31):
I know.
Dr. Sarah Bren (04:31):
When you were done together.
Dr. Emily Upshur (04:32):
As you were reading it, I was like, “That sounds like a win.” I was literally like, “Good job. I think that went well.”
Dr. Sarah Bren (04:39):
Right. And that’s what I mean by saying, “I don’t actually think you have to change anything other than the story that you were telling yourself that that’s not work, that this is unsuccessful.”
Dr. Emily Upshur (04:50):
I guess … Oh, go ahead.
Dr. Sarah Bren (04:52):
Oh, I was going to say at three and a half, if this was static and never changed over the course of development, okay, then we’re talking about something else, but we’re saying at three and a half, this is like the foundation I’m laying. These are the building blocks and it’s what they look like at three and a half. It’s I do 90% of the work, but I’m helping you cross that finish line and we’re doing it together and I’m naming what I’m doing. I’m modeling motor planning, organization, sequencing. First, I’m going to pick up the magnetiles and you’re going to help me put them in this basket and then we’ll get the stuffies and put them away. So it’s a lot of scaffolding. It’s a lot of like repeating this over and over and over again until you slowly start to pull away the scaffolding and you do a little less and she does a little bit more, but that takes time.
Dr. Emily Upshur (05:52):
And I guess the thing I was thinking is, it’s also like just like a practical little tip is like, especially if you have this like really nice awareness that your daughter has OT and motor planning problems, she’s working on these things, I would say just really practically, give yourself just a tiny bit more time than you think that you might need for this. Because I can hear in this mom’s like voice, like, “But my whole night is getting pushed because you still have to clean this and then you have to take a bathth and then you won’t be in bed until…” And I think that’s also helps reduce that parent feeling like I’m trying to keep deep, deep breaths and stay regulated and not get frustrated, but as we always talk about in here, evenings are really tough, right? Everybody’s worn out, everybody’s a little stretched thin.
(06:43):
And if you give her a little less play time and a little bit more time for play to include the collaborative cleanup, you’ll feel a little less frustrated because remember you’re the time, you’re the clock sort of. Kids don’t, a three and a half year old doesn’t have that internal sense of how long things take, the planning around that. So give yourself like a little bit more time too. You’re doing a lot of good things, right? And just maybe start that clock a little sooner so that you don’t feel that pressure, that parent pressure.
Dr. Sarah Bren (07:17):
Yeah. Yeah. I love that. Another strategy that made me think of that also is like, okay, we’re talking about like the mindset stuff, which I really think you’ve already kind of like done like a lot of that work. Then there’s like, what tools are in my toolbox? And so yeah, adding more time, but also another strategy that could work that might be helpful is like coping ahead or planning ahead. So like when we’re getting the memory cards out, we’re going to say, “Okay, the top of the box, we’ll put that here and as we play, we’ll put the cards in the box as we go so it’s easier to clean up.” Or like if that works. So like just kind of helping sort of warm up, preheat the oven, as I like to say, of like the executive functioning skills necessary to plan, initiate and conclude a task and have cleanup part of that.
(08:16):
So, “Oh, what do you want to play right now? Oh, I want to play memory.” Okay, so what’s our plan? First we’ll get the box, the game out, and then we’ll play, how many games would you like to play? “I want to play two games.” “Okay, we’ll play two games, and then we’ll clean up, we should probably make sure we have time to do that, and then we’ll go to bath.” And so now we’re preheating the prefrontal cortex a little bit, the executive functioning skills. We’re getting those like sequencing, organizing, like circuits lit up a little bit, and then when it’s time to transition into that phase, it’s not like, “Oh, wait, we have to do that? We have to clean up?” Even though they know, even though they clean up every single time we play, it’s just kind of like priming them for it.
Dr. Emily Upshur (09:12):
And I think of it also as the emotional priming too. So you love this game, it might be hard to end this game. We can play memory, but that memory game, man, it’s been so hard for you to play only two rounds of that game. What if we put on, we agree that no more than two, we’re going to make a plan right now, even if you feel like at the end, I really don’t want to stop, I really don’t want to end, we know we can handle that. I think priming, warming up that oven, doing that preheat for the emotional management is just as important as well as the executive functioning piece of it. They kind of go hand in hand. Agree. And I think that can really help. And you know, this parent knows their kid, so they really know what leaver emotional touch points they have to sort of integrate into that to make it the most successful in terms of preheating that a little, giving a little primer.
Dr. Sarah Bren (10:07):
Yeah. I mean, and I think like she’s talking about three and a half year old trying to transition from a preferred activity, like a game to a less preferred activity, which would be taking the bath. I think the same kind of model and framework can be applied to any age kid and any intensity of like preferred activity to non-preferred activity. I think this happens so much with screens, like trying to transition off of anything screen related to another task of the day.
Dr. Emily Upshur (10:41):
Anything.
Dr. Sarah Bren (10:42):
Yes, anything.
Dr. Emily Upshur (10:43):
Breathing, breathing in another room.
Dr. Sarah Bren (10:45):
Right. That also can elicit a lot of resistance in children, if not full blown tech or no tantrums. But again, preheating the oven, not just for what’s the plan, but also what’s the plan for when you feel really, really frustrated.
Dr. Emily Upshur (11:03):
Yeah, when it’s hard.
Dr. Sarah Bren (11:05):
Yeah. And when like the not wanting to do this kicks in, like what helps, what feels better. And then even just thinking too, when we have a preferred activity, transitioning to a non-preferred activity, how do we try to help the non-preferred activity feel a little bit more preferred? If it is, in fact, I don’t like ending playtime to go do bathtime because I don’t like bath time. How do we help bath time be a little more enjoyable or playful or fun? And I mean, especially three and a half, I think play is such a helpful tool to bridge a transition. Songs, music, you know, take a page from a kindergarten teacher and play a cleanup song. It’s not just cutesy, it’s cues, it like activates a cue. It’s paired with an association over time. And so even if, at first you just put the cleanup song or you sing a cleanup song while you clean and it just becomes part of the rhythm of things, eventually when you play that song, your child’s going to associate with cleaning up.
Dr. Emily Upshur (12:39):
Well, and I also think cleanup are these less desirable tasks, right? Like the part of the task, because the kid likes this game, they just don’t like cleaning it up. They prefer the bath more. They’re like, “Sure, we don’t need to clean up. Let’s just get in the bath. This is great.” I think what you said, this is sort of like thank you. Cleanup to me is like the thank you of parenting. It’s like you have to prompt your kid to say thank you until their mind is 15, so they still do it. You still do it occasionally. So I think if you’re like feeling like, why aren’t they getting it? This parent’s like, “Why isn’t this easier?” I think it’s just because it’s not to sort of circle back to what you said in the beginning, it’s like, “Oh no, this is just how it goes.” You have to say, “Okay, now say thank you. Say please.” You have to prime and cue, “All right, this is what we do after an activity. This is what we do when we take our clothes off. They go in the hamper. This is what we do You’re going to be doing this throughout your child’s life.” So I think managing that expectation too, like we’re priming the oven for the parent right now to sort of be like, “This is kind of expected, right? Like you’re going to have to structure this. You might have to collaborate on this and structure it. ” And to your point, less and less, you’re not going to clean up 90% of the time forever and ever in perpetuity with your kids, but you might have to, that scaffolding might still be there in other ways.
Dr. Sarah Bren (14:07):
Yeah. And I’m also just thinking, I think that’s incredibly important. It’s like you got to put in the reps. We have to put in the reps, they have to see the reps for them to do the reps themselves and practice, practice, practice infinity times. Another one thing I’m thinking of, just because this mom is mentioning like OT and motor planning challenges and just like, obviously this is somewhat just my own experience. I have a really hard time cleaning things up as a human with ADHD and I’ve spent most of my life fighting with my family members about whether it was my fighting with my parents when I was a kid or my husband, my roommates as a young adult or my husband as an adult. Everyone gets mad at me because I avoid cleaning so much and part of it is … And then so I’m just trying to pull back the curtain on like, what is overwhelming for me about cleaning? I had to figure this out because otherwise I wouldn’t have any relationships.
Dr. Emily Upshur (15:09):
I’m the opposite of you, so this is why we’re so well matched. I’m the one who gets mad at you.
Dr. Sarah Bren (15:14):
Right. But I think for me and what I’ve been able to finally identify so that I can accurately articulate is when I walk into a space that’s messy or if I’m in a space in the middle of a mess that I’ve created and I’m become aware now of the mess that I have to clean, what happens for me most of the time is that I see it and because my brain somewhat struggles with organization and sequencing, I get very overwhelmed and I don’t know where to start. Once I’m going, I can clean up. Oh, also I have a bad sense of how long I think it will take. So if I look at a room that is a mess, time blindness. One, I think to myself, I don’t even know where to begin. I just, I’m flooded with overwhelm and it makes it really hard for me to know where to start or create a plan.
(16:06):
And the other thing is I say, “This is going to take me five hours. I don’t have five hours. I’m going to put this off till I have five hours. I just don’t want to … ” It seems to still so big. Now the funny thing is, is if I get started, if I say…
Dr. Emily Upshur (16:20):
It’s hard for you to stop.
Dr. Sarah Bren (16:22):
“Okay, I’m just going to start with this pile of papers right here or I’m going to set a timer for five minutes and I’m just going to put away what I can in five minutes and I will stop no matter what size the mess is when I’m done.” I usually can completely clean up the thing I thought would take me five hours in like five to 15 minutes, depending on what I’m dealing with. But I always surprise myself at how much I overestimate how long something’s going to take me and when I have one place to start, like even just one thing I can identify, “Oh, I’m just going to get the pieces of paper or I’m just going to get the magnetiles.” There might be 400 toys in this playroom, but if I’m just going to look for the magnetiles and put them in the magnetile bin, that’s all I’m going to focus on.
(17:08):
All of a sudden in doing that and being from planning to action, in action, I am able to be a lot more nimble and I’m like, “Oh, here’s crayons. I’ll just throw these in the bucket too while I’m doing the magnetiles.” And like, oh, all of a sudden I realize the stuff is done.
Dr. Emily Upshur (17:26):
Right. So what I’m hearing is parents can do a little what I call jazz hands over here. They’re like, “Oh, look at that crayon. Oh my gosh, how many crayons can you find? Okay, there we go. Now the motor is moving, we’re engaging in the first gear and then from there it’s much easier.” It’s hard for you to begin the task. It’s that task initiation that’s really tricky.
Dr. Sarah Bren (17:45):
Yes, task initiation. And I think a lot of times it’s due to not even having a good weight place to start.
Dr. Emily Upshur (17:53):
Place to start or the time, overwhelm time management.
Dr. Sarah Bren (17:55):
Yeah. So give them … And again, that’s just how my brain works. It might not be how every child who’s struggling with cleanup is struggling, but…
Dr. Emily Upshur (18:04):
But I do think developmentally at three and a half, giving a concrete instruction, instead of cleaning up the game might be too overwhelming and broad. If you say, “Can you pick up those three cards?” That might be more grounding. So I think giving a little bit more concrete directives. We talk about this a little bit in parenting is like a command is actually not a bad thing, it’s a clear expectation, right? So please pick up that card, not clean up the game. A three and a half year old needs, please pick up that card and that’s an achievable command for them and that really helps the parent to be more clear.
Dr. Sarah Bren (18:43):
It’s also far more activating. If you say to me, “Sarah, go find all of the pieces, find all of the Post-its,” because right now my desk is covered in a million different post-its, half of them are garbage. If you say, “Sarah, just gather up all the Post-its on your desk. Don’t even throw them away. Don’t have to sort them because some of them are important and some of them are garbage. Just make a pile of all the Post-its.” I could do that. I would not feel overwhelmed by that command.
Dr. Emily Upshur (19:10):
If someone said, “Organize your Post-its.”
Dr. Sarah Bren (19:12):
I’d feel very overwhelmed. If someone said, “Just find the Post-its that have a podcast episode idea on it and make a pile of those.” Great. Or just find the sealed envelopes in your office right now because I’m terrible. I collect mail and don’t open it. So just get all the envelopes that you haven’t opened yet. I can do that. So yes, if you approach cleanup instead of like, “Hey, let’s clean up the game,” but say like, “All right, you find all of the blue cards and I’ll find all the green cards.”
Dr. Emily Upshur (19:54):
Chunk it into something. Yep. And that’s a great strategy for ADHD and that’s a great strategy for young children and frankly, I think it’s just a good strategy.
Dr. Sarah Bren (20:02):
Yeah. I mean, frankly, most things that work really well for ADHD people work really well for everybody.
Dr. Emily Upshur (20:08):
For people.
Dr. Sarah Bren (20:08):
For people. That’s right.
Dr. Emily Upshur (20:10):
Yeah. And definitely for any brain, like brains like to feel organized too, right? Yeah. So I think it feels good to clean up something. Once you collected all your post-its, you probably have a little bit of dopamine, right? It’s a little bit exciting in your brain. And so we can create more reinforcing systems like that, that it actually doesn’t feel so much less desirable, so painful to do a less desirable task, then you’re also creating more opportunity that they’ll not resist it as much.
Dr. Sarah Bren (20:42):
Absolutely. And to that point, I think something that gets overlooked a lot is the integration phase after we clean, like that rest reflect. Love that. After you clean up the memory cards, even though you’re just like, “All right, good. We’re done. Let’s get bad time. Get a bad time.” Slow down and say, “Look, we put them all away. They fit so nice in this box. That was a fun game.” Pause for a moment. Just let it be … Sometimes I think we really undervalue the impact of when our kid actually does cross the finish line, even if we’ve scaffolded 97% and they just took the last three steps across the finish line, we really want to say, “Ah, look at that. You crossed the finish line. You put the top on the box. Okay, that was so fun to do this with you. Let’s do it again soon.” Should we go take a bath now? Slow down, name what happened. We’re trying to get them to log it so that they feel it.
Dr. Emily Upshur (21:53):
And I love that for you logging what you said is so important and I think a really good time for this also, maybe not quite at three and a half, but also to say like, “Wow, we did that in five minutes, two minutes.” To sort of begin to teach that time management skill, that felt like a big annoying thing and look, I feel like that was only a small thing and maybe it wasn’t so annoying. I think whatever language you need to do to sort of like give it a little bit of containing with time and predictability also helps because then the next time, inevitable thank you next time, say thank you next time, it won’t feel … So it might, you begin to put in the scaffolding for like the time management skills and the ability to not see it as a giant thing.
Dr. Sarah Bren (22:42):
And the relativity like, oh, I thought it was going to be really overwhelming to do this or feel really annoying to do this or take forever to do this. And then I’m readjusting the perception and I’m matching it to the reality because if we skip that part, it’s going to be like groundhogs day the next time you got to pick up this memory game and they won’t have had changed the frame. You might have to do this- Do it again. … a few times before they independently change the frame, but that’s also part of the work. Not just we have to learn, we pick up our toys, but we have to learn that when we pick up our toys, it wasn’t as bad as we thought it was going to be.
Dr. Emily Upshur (23:30):
Well, right. And that’s the beauty of when your 10, eight, 15 year old says, “Thank you so much.” And you’re like, “What? I won the lottery.” All that hard work, all those reps, you did hear me.
Dr. Sarah Bren (23:45):
Yes. Yeah. It’s like the other day, my daughter and I were having a power struggle and I came outside, she was playing with chalk and she wrote in chalk, “I’m sorry.” And I was like, I was like, aww.
Dr. Emily Upshur (24:05):
Winning.
Dr. Sarah Bren (24:07):
She’s getting it. She’s getting here eventually. And like, yeah, that was the blooming of something that had been planted a seed and watered and watered and watered and watered, watered and watered and watered a million times before I got the spontaneous apology.
Dr. Emily Upshur (24:23):
Any reward. Any good job, mom. Yeah.
Dr. Sarah Bren (24:28):
That’s my good job. I should have taken a picture of it and framed it.
Dr. Emily Upshur (24:31):
Oh my gosh. I have done that.
Dr. Sarah Bren (24:35):
Just to remind myself. Okay.
Dr. Emily Upshur (24:37):
Yeah.
Dr. Sarah Bren (24:37):
It’s working.
Dr. Emily Upshur (24:38):
I did that. Yeah.
Dr. Sarah Bren (24:39):
All right. Thank you, Emily. And thank you so much for writing in this question, dear mom. I hope this is helpful and you’ve totally got this.
(24:48):
Thank you so much for listening. As you can hear, parenting is not one size fits all. It’s nuanced and it’s complicated. So I really hope that this series where we’re answering your questions really helps you to cut through some of the noise and find out what works best for you and your unique child. If you have a burning parenting question, something you’re struggling to navigate or a topic you really want us to shed light on or share research about, we want to know, go to drsarahbren.com/question to send in anything that you want, Rebecca, Emily, and me to answer in Securely Attached: Beyond the Sessions. That’s drsarahbren.com/question. And check back for a brand new securely attached next Tuesday. And until then, don’t be a stranger.

