Beyond the Sessions is answering YOUR parenting questions! In this episode, Dr. Rebecca Hershberg, Dr. Emily Upshur, and I talk about…
- How to support a sensitive, gentle child in becoming more confident using his voice with peers.
- The difference between helping your child build self-advocacy skills and trying to change their temperament.
- How to teach kids simple, effective boundary-setting tools that actually work in fast-paced peer interactions.
- Why “old soul” kids may naturally learn polite, sophisticated communication, but still need help practicing more direct forms of assertiveness.
- Playful ways to practice boundary-setting and self-advocacy skills at home through games and role play.
- How to know when to step in as a parent and when to allow kids space to navigate social challenges on their own.
- Why it’s important to match a child’s communication tools to the intensity and energy of the situation they’re in.
- The importance of checking whether a child is actually distressed before assuming a social interaction is a major problem.
This episode will help you feel more confident supporting your child’s self-advocacy skills while still honoring their unique temperament, sensitivity, and personality.
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.
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
- Learn more about Dr. Rebecca Hershberg on her website and by following @rebeccahershbergphd on Instagram
CHECK OUT ADDITIONAL PODCAST EPISODES YOU MAY LIKE:
🎧 Listen to my podcast episode about how you can parent your child to not be a people pleaser
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. We’re going to answer a listener question and I have two of my favorite people in the whole wide world, Dr. Rebecca Hershberg and Dr. Emily Upshur. Thank you for coming on.
Dr. Emily Upshur (00:58):
Hi.
Dr. Rebecca Hershberg (00:58):
Always. Always such a highlight.
Dr. Sarah Bren (01:01):
It is. Shall we jump into our question?
Dr. Rebecca Hershberg (01:04):
Yeah.
Dr. Sarah Bren (01:05):
This is addressed to all three of us. Hi, Dr. Bren, Dr. Upshur and Dr. Hershberg. I’d love your perspective on supporting my fear old son and becoming more vocal about his boundaries with peers. He’s a very sensitive, calm, observant child, truly one of those old soul kids. He kind of makes you look like the parent of the year, but I’m very aware that this is largely his natural temperament rather than some parenting magic on our part. With that being said, he’s on the more timid side, slow to warm up, not drawn to the spotlight, and unlikely to raise his hand or assert himself loudly in a group, which we intentionally try to honor as part of who he is. Once he feels comfortable though, he does great. He has friends, enjoys playing with others and is often sought out because he’s easy and going and adaptable.
(01:49):
What I sometimes notice and where my concern comes in is that other kids don’t always respect his physical or emotional boundaries and he doesn’t always have a strong enough no to stop more outgoing or dominant peers. For example, a group of kids were playing a running game where they were physically blocking him from moving forward. He clearly didn’t like it and did say stop a few times, but it wasn’t enough to override the behavior and eventually parents stepped in. I try not to intervene too quickly and when I check in with him afterwards, he doesn’t seem to stress or anxious about these interactions. He still loves playing with his friends and doesn’t avoid social situations. That said, I worry about situations where I’m not around and boundaries might be crossed further. I’m trying to find the balance between not being overprotective and still equipping him with tools to advocate for himself.
(02:32):
How can I support a child like this, sensitive, gentle, not naturally loud in developing confidence around using his voice and holding boundaries without pushing him to be someone he’s not? How would you recommend talking to him about this at home? Are there skills we can practice that feel empowering rather than alarming? So thoughts on this mama’s concerns. Totally get it.
Dr. Rebecca Hershberg (02:55):
Totally get it. And also I’m so impressed with everyone who writes it. This is clearly the best mom. I mean, she’s just so thoughtful about this. She’s already done our work for us. I feel like normally I’d be like, “Well, you need to toe the line between not wanting him to be someone he isn’t, but also empowering him.” It’s like she already said that part.
Dr. Sarah Bren (03:18):
Yes. Yeah, no. So I am in full agreement with you. She’s done so much of the work for us in the sense that she’s paying attention to these polarities and she’s really thinking about middle line. I think she says something else that’s really important that she’s tracking, which is he isn’t distressed. She’s checking in and he’s not expressing distress. So this doesn’t feel like an alarmist question like, “Oh my God, this is a big, big, big problem and it’s a big, big, big solution.” It’s just she recognizes that there’s some places where a skill for self-advocacy and speaking up and stepping outside your comfort zone to maybe set a boundary that there could be some skill building scaffolding around that, but still not necessarily like, “Okay, this is a big problem that we need to create a solution for.
Dr. Rebecca Hershberg (04:18):
” Yeah, exactly. I think that’s true. I think the recognition that he is who he is and that that’s not going to change is so important. I think what occurred to me when I was reading or when you were reading the question, I should say, I remember when my kids were in preschool and they were learning to set boundaries and that they were told, “Use a loud voice.” And so they were told if someone was sort of doing something you didn’t like or in your space and they taught them to like, “You can’t see me obviously because you’re just listening,” but to put their hand out and just say, “Stop.” Just like one word.
Dr. Sarah Bren (05:02):
I love that that was education for your kid. I don’t think that’s typical, unfortunately. I actually think that that’s phenomenal.
Dr. Rebecca Hershberg (05:10):
Oh, it was amazing. I remember at one time, sorry, tangent, my nephews were playing with my kids and I overheard my kids, they were about to play like, I don’t know, football or something, whatever it was. And I heard one of my kids say when they were little, “Okay, but first let’s go over our boundaries.” And then I paused and the other kids, of course, my nephews looked at him like, “What are you talking about? ” And he was like, “I don’t want anyone pulling my hair or touching me. ” It was the ritual that they would go before playing anything physical, they’d go over their boundaries, but be that as it may, I just wonder if just some very basic, with sort of no judgment, I think oftentimes we over talk these things, like sort of no long conversation, no, it’s okay to … I don’t get the sense this kid is actually internally troubled at all. She mentions he loves his friends, he loves social interactions. She just kind of wants him to be a litle bit more assertive when he doesn’t like something.
(06:08):
And I honestly feel like just talking about a really concrete thing like the voice volume or like using your arm, just that it’s okay to just, because we teach our kids and to be polite and to say, “Hey, excuse me, would you mind whatever?” And just there are situations where it’s okay to just hold out your arm and say, “Stop. I don’t like that. ” And to maybe just practice that a few times at home and give quote unquote permission. And I imagine that might help some of this.
Dr. Sarah Bren (06:41):
Yeah. What you’re saying actually makes me think about this thing I teach a lot when I would be doing like distress tolerance support for like adults even, but also with kids. But I’ll often say, like for example, if you’re really, really upset and you have an urge to scream or throw and someone’s trying to help you calm down and you’re trying to replace that behavior with like, “Oh, just drink a cup of chamomile tea.” It doesn’t match at all. It won’t work. If I’m at a 10 and I have an intervention that works for like a level three, it doesn’t really work for that thing. A couple of camel tea might really help you calm down if you’re at a three and you want to go to a two or a one, but if you’re at a 10 and you need to bring it down a couple notches, like you need something that matches that intensity level and I think that that’s a helpful kind of framework for this as well.
(07:40):
If you’re trying to teach a kid how to have assertiveness skills and how to ask for what they need, certain context, you might be teaching them how to interrupt you appropriately when you’re trying to talk to your friend and they want to get your attention. In that case, you might want to teach them, “Hey, if I’m talking and you need to get my attention, you could put your hand on my arm or you could say, excuse me, can I talk when you’re finished or whatever.” That context, that intensity level matches that setting and that dynamic like a little kid talking to a grownup who has all this language stuff that they have to work with, this big toolbox. But if you have a five year old who’s trying to navigate his way on a playground with other five year olds who are moving really fast and they’re moving really intensely because they’re also like playing and really like, woo, big eight, nine, 10 level energy, to have a tool in his toolbox to like place his hand on an arm and say, “Excuse me, can I have a turn to talk when you’re finished?” That’s not going to break into that level of energy with these kids.
(08:46):
So also helping kids kind of have a toolbox where they know how to discern what’s the, to your point, Rebecca, like when do you say, “Excuse me, can I have a turn?” Versus, “Hey, I want the ball now. I want it next or stop just a hand.” It needs to match the setting and the level of energy of the people who you’re interacting with and the level of skill with the people you’re interacting with. So if you’re interacting with a five year old who’s moving really quick, you don’t have time and they’re not going to process a long sentence explaining your boundaries, they just need a hand.
(09:30):
And so I think that’s actually like unstated a lot of the time of like, we got to give kids both the quick and dirty version of how to set a boundary and the longer, softer, more sophisticated way. But I think these like super mature old soul kids that can talk to grownups, they get a lot of the learning around the long, complex, socially sophisticated boundary setting that happens with adults or with like calm, mature people that are regulated and we might not always remember we should actually be very explicit in teaching them some of the quick and dirty boundary settings for other hot, fast, quick, loud five year olds or three year olds or whomever.
Dr. Emily Upshur (10:17):
But I think they’re going to require practice because what I’m hearing this mom say is, “Sure, and that’s not my kid. So how do I bring them up to speed or how do I practice that part that might be applied to that playground stuff?” How do I help him practice that?
Dr. Sarah Bren (10:36):
Well, I think one way to practice it would be to play games with it. Even games like red light, green light, things that help you practice having a quick response and like physically moving your body, like I might say, “Okay, let’s play this game. We’re going to play red light, green light.” You stand over there and you come to me when I say green light, but when I say red light, you have to stop. And when you say red light, we can have them practice things like, put your hands out, say stop and like you can do the red light. You want them to be doing the red light, green light for you. So you play it with them where you’re the light and then you switch and let them be the red light. And when they are the red light, they’re going to have their arms out.
(11:18):
They’re going to say, “And red light, stop.” And you can get them to practice these things with you and then you can talk to them about how you could use those skills even when you’re not playing this game. How could you use this skill if someone is like, “You want to get someone to stop quick?”
Dr. Emily Upshur (11:37):
I think the other thing, as you’re saying that though, I’m thinking is this is like five year olds in the wild on the playground that she’s observing this, they’re all together at this age it’s still really possible to do sort of a small hosted play date where you can practice some of these skills in a smaller setting with less children. I always encourage parents to do a little bit of their stretching stuff like if you’re trying to stretch your kid to be something a little bit out of their comfort zone or even the tone of voice, the language, the physical interactions, it’s good to host because you get to sort of do a little coaching on the side and so then when they go to the playground, because doing it alone or even doing it on a one-on-one play date doesn’t really practice in the setting that you’re … But if you have two or three kids over, you can sort of get a little closer to that in the wild on the playground experience.
Dr. Sarah Bren (12:32):
But I also think in order to do that, you have to recognize if you have to like check in with your kid and actually see if it’s something that is a problem for them because, and I think this mom explicitly recognizes this. She’s checking in and saying like, “He’s not bothered by this. ” She’s just anticipating scenarios that he could be potentially bothered or benefit from some skills around this so he can get his needs met more effectively, which is great, but if a kid really isn’t bothered by it, they might not be particularly motivated to practice this. So I think you have to help them perhaps explore I’m thinking of a scenario where like if I’m talking to a kid who’s pretty chill about stuff and I’m like, “Yeah, did it bug you when that other kid kind of like knocked you back when it was your term for the slide and kind of went in front of you?
(13:24):
” And they’re like, “Nah, not really. ” They’re like, “Okay, I get it because you’re pretty flexible, but could you think of a time when like maybe it would bother you? ” What’s your threshold for getting pissed basically? And even if it’s not that the thing that happened, even just imagining with them, like what would it kind of take for someone to do that would be like, “No, I’m really not okay with that. ” And maybe they could say like, “Well, I wouldn’t like it if they pushed me and I fell down.” Like, “Oh yeah, has that ever happened?” “Oh yeah, the one time or no, it hasn’t. “Be like, ” Okay, so if it did happen, you could say like, “What do you wish you could have done then?” Or if it hasn’t happened, you could say like, “Well, what do you imagine you would do in that situation?” So you can try to almost like play out scenarios based on not what has happened, but what could happen at the level at which they would actually be motivated to say something or do something so that I think you got to get the buy-in for the imagining because then if you practice a skill, it’s got to match what they anticipate needing it for, right?
(14:30):
If they don’t care if someone cuts in front of them in line and you’re practicing how to say, “Don’t do that, ” they’re probably not going to use that in real life, but if they can identify that if someone were to push me down, that would be something I would want to be able to say something about. So I do think sometimes it’s a little bit, to your point, Emily, about practicing and role playing, first you have to find the mark that you’re practicing for that actually is of interest to them and then practice skills around that.
Dr. Emily Upshur (15:02):
But I think this parent, like while we’re seeing her being really measured about this, it does seem like there are maybe a few times that have popped through that are behind this question of like, what happens if he expresses his voice and it’s not always heard, right? Or we’ve had these times where I think she says in her question like parents have had to step in or intervene and that I think is sort of underlying this, right? Like what happens if the kid’s capacity is overrid by this situation? How do I help him get closer to that? Because she aptly says, “I don’t want to intervene too quickly.” And I think it’s really attuned of her, but I also want to acknowledge that she’s saying like, maybe sometimes I worry that he doesn’t have the skillset to be able to get that addressed without adult intervention.
(15:54):
And again, this is a fear old, so that’s also appropriate. So I’m not like, “Oh my gosh, without that, I think this is a five year old still need some adults in the mix, but I do want to acknowledge that he might need to practice this a little. That is something that she’s expressing. The stop was a few times wasn’t her, didn’t land.”
Dr. Rebecca Hershberg (16:17):
Yeah. I also think this is where teachers come in handy. It’s just sort of like, find out if this is a thing. And I think this mom again has a handle on the fact that some of this may actually be a thing, some of it may be her, some of it may, but get other adults who see your kid in social situations. I’ve worked with families where they’re like, “Yeah, I experienced my kid this way.” And then the teacher is like, “Yeah, this kid is super assertive and is like a leader.” I mean, you just don’t know. And so I think when we’re talking about starting to ask a kid about hypothetical scenarios or whatever, I think that’s a great approach, but I also think we can get a present day assessment of how founded is this mom’s worry that this is happening when she’s not there.
Dr. Sarah Bren (17:09):
Yeah. I’m really glad that you wrote in this question. I hope that we answered a couple different ways of thinking about it and we so deeply appreciate everyone’s questions. It means so much to us that you are not only listening to the podcast and appreciating it, but finding ways to identify with it personally and bringing those questions to us because this is exactly what makes our week. We love doing this so much and getting to know you guys. So thank you. Thank you, Emily and Rebecca for coming on. I always love your wise input.
Dr. Emily Upshur (17:43):
Always nice to be here.
Dr. Rebecca Hershberg (17:44):
Always great to be here. Thank you.
Dr. Sarah Bren (17:48):
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.

