Staying Connected While Kids Feel, Fail, and Figure It Out

In this special, closer-to-home episode of Parenting the Mental Health Generation, host Amy O. shares a real (not scripted, not polished) conversation with her daughter, Shawn. It was recorded for a CATCH “Brave Parenting” event on February 25, 2026. Together, they talk about what it looked like to grow up in pressure-filled community, chase achievement for a sense of self-worth and battle crippling anxiety- all while trying to stay connected. 

They get honest about the moments parents miss, how reassurance can feed anxiety, and why kids need space to feel what they feel, without being rushed, fixed, or talked out of it. This episode isn’t about quick solutions. It’s about presence, repair, and building trust that can hold steady when things get messy.

Action item: Over the next few days, choose one moment to validate instead of fix. Reflect back what you see or hear, “That sounds really hard,” “I can see why that upset you,” “Thanks for telling me”, and stop there. No lesson. No solution. Just connection.

SHOW NOTES:
Letting Go and Trusting What Matters Most | A Brave Parenting Conversation

music credit: Line Up/Pond 5
©CATCH 2026

To find all of the resources CATCH provides to caregivers of young people struggling with their mental health, go to www.catchiscommunity.org.

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CATCH, Community Action Together for Children's Health, is a 501(c)3 that provides support and education for families around mental health topics. Original content and materials from CATCH and its collaborators are for informational purposes only. They are provided as a general resource and are not specific to any person or circumstance.

Transcript

Introduction

Amy 0.: [00:00:00] Welcome. I'm Amy O., the founder of CATCH, Community Action Together for Children's Health, based in Chicago's northern suburbs, and this is Parenting the Mental Health Generation. 

Today's episode is a little different, a little closer to home. This conversation comes from a "Brave Parenting" event where I sat down with my daughter, Shawn, to talk honestly about our experience, not as experts, us not as a success story tied up with a bow, but as a parent and a child who've lived through the complexity of mental health together. What you're about to hear isn't scripted. It isn't polished, and it isn't meant to offer quick fixes. It's a real conversation about listening, misunderstanding each other, learning as we go. And what it actually looks like to stay connected when things feel hard, confusing, or emotional.

If you're parenting a child or teen and sometimes wonder if you're saying the wrong thing, or not saying enough, or just trying to figure out how to show up without making things worse. This episode is for you.

My hope is that you'll listen. You'll hear pieces of your own family, your own questions, and maybe even your own fears reflected right back at you.

So wherever you are; in the car, taking a walk, or folding laundry, take a breath, settle in, and listen, not for answers, but for connection. Put your earbuds in, take this 30 minutes for you and join my conversation with my daughter, Shawn.

Conversation

Amy 0.:: Good morning, Shawn.

Shawn O.: Hi mom.

Amy 0.:: How are you?

Shawn O: I'm good. How are you?

Amy 0.:How's Colorado?

Shawn O.: It's good. It's a little chilly today. Not enough sun for me. 

Amy 0.: First I just wanna say thank you so much for agreeing to do this.

Shawn O.: Yeah, of course. Thank you for having me here.I'm excited.

[00:02:00] Amy 0.:I'm grateful that you are willing to talk with me today and just reflect on our journey together. Things that we've learned together, things that we've learned separately, in hopes that we can share those things with our community up here.

Shawn O.: Yeah, well said.

Amy 0.: So since CATCH started, we have talked in many different ways about the pressures and the expectations that kids feel in our community. And I know that those things were a big part of what you experienced in your journey as a teen or maybe as a kid in general. So can you just start by reflecting a little bit on how those expectations affected you and some things that you might've learned about your own self-worth along the way?

Shawn O.: Yeah, yeah, for sure. I think that's a great question. When I was first in elementary school, I very much thought that like school was the way you were tested on whether or not you were intelligent. Whether or not you were a smart kid. And I was a little slower to read than maybe some people, and I took that really hard as a kid. And so I decided to put my head down and really work hard at all of the things that I thought would prove that I was a smart, capable child and so I worked really hard at school. I, you know, really wanted to be a straight A student all the way through middle and high school, and I dove into every sport that I could, and I tried my best to be the best athlete I could. I listened to everything the coach said, and I think all of it was really just a little Shawn chasing the feeling that she was enough and chasing the feeling that she mattered or that she had a place in the world. And that if she fought hard enough, then like at least that place was gonna be there. And what I think she was really missing was like the internalized like no, you also matter as little Shawn the person, not Little Shawn the soccer player, little Shawn the basketball player, or little Shawn the one that always gets A's. There is an inherent being to you that matters and that deserves to be loved. Even if they get a C on a math test. That still matters through that. And I think I really did not internalize that. I really thought that since I had all the resources I could to succeed in all avenues, why not try and do it? That mindset can be good, but I very much skipped over like, what do I want? Who am I and what do I wanna be like? I just kind of tried to get all the things that were shown to me that were going to help me be a capable person and I was trying to do them to the best of my ability. I was trying to control feelings of anxiety like, am I enough? Am I worthy? If I have these accolades, if I have the best mile time, if I have all A's, I have to be, right? And in that, I think it's really important that kids know you can actually fail at all those things and still be worthy. You can also be a really bad soccer player, but have a lot of fun out on the field and that matters just as much. And I think it's really important for all children to know that they matter, even if they do things they're bad at, even if they're not good at the things their friends are good at.

Amy 0.: Do you think that, in some ways, Dad and I missed that? It's been a long time, to be honest with you, maybe even never, since you've really articulated that to me as an adult and do you think Dad and I missed somehow, ensuring that you understood that. Whatever it is that you chose to be or do or however well you did it, you were always loved, supported enough?

[00:06:00]Shawn O.: You know, that's tough because, no, I, I was always aware as a kid that my parents didn't care about me getting straight A's. My parents didn't care about me being the best athlete, but there was something. I think within, you know, Northbrook or the suburbs that teach kids to be as prepared as possible for everything in life. And unfortunately, there's no way to do that well. And so we just, at least I did, tried to be the best at all of the things that seemed important in that community. And that was sports, and that was grades, and that was, you know, whatever

Amy 0.:involvement in things.

Shawn O.: Yeah. I think maybe what could have been missed was the modeling of handling really tough emotions. I don't think I really saw you guys work through emotions on your own. I think you guys kind of did that, uh, away with each other. And I think if I would've seen that, like sometimes emotions can be overwhelming. Sometimes dad doesn't think he's enough. Sometimes mom doesn't think she's enough. It's not just me. I think that would've changed the narrative a little bit because I think I would've been a little bit more honest about how insecure I was feeling despite me being loved and supported. And

Amy 0.:So you mean like Dad and I being more vulnerable in front of you, with you even? [Yes, yes, yes.] What would that have looked like? If I were working through something tough or felt anxious about things, which of course I did, and still do all the time. [Right.] It would mean saying that out loud to you, like,

Shawn O.: Yeah, like, I'm a little nervous for this board meeting right now. You wanna shake it out with me? You wanna go over what's gonna happen? You wanna see what I do when I feel uncomfortable or when I have to do things that are hard?

Amy 0.: So not, not just saying. Okay, let's buck up. Let's do this. 

[00:08:00] Shawn O.: Because I think let's do it anxiously just have kids stay in this uncomfortable, scared place and that's a really icky place to stay in. And so how do we move through anxiety and do things that are hard? Because anxiety doesn't make you less of a person. Right? I think that that was what I was kind of feeling at a young age, like when I was having big emotions, how do I control these emotions with, you know, running, with sports, with grades, with perfection. How can I not have to feel these tough emotions and get through them? And, and what I thought through them was, was just pushing them down as much as possible.

Amy 0.: So, two things are coming to mind, super clearly that I haven't thought about since you were, what, like, I don't know, 13. Do you remember, before you took a test? First of all, how detailed all of your note cards were to the ‘nth degree, and then how many times you wanted us to quiz you, quiz you, quiz you, quiz you like I would and we were like, oh my gosh, look at her. She's just a [hard worker, isn't she?] I mean, we kind of began to realize that you were way overdoing it, but we didn't realize that way overdoing like that equaled really intense anxiety. Yeah. And did it go away with all of that practice, or did it just sort of intensify inside your brain?

Shawn O.: Yeah, it's, no. Once you have anxiety and the way you try to fix that anxiety is reassuring it, that anxiety's just gonna keep asking for more. It got to a point where I would wake up in the middle of the night and check my assignment notebook and make sure I did all my homework. It plagued me. Everything I thought about was homework, school, exercise, and, you know, that leads to eating disorders often, which is a very, that makes sense. It's all a sense of control, and I don't think I was ever taught that letting go of control is a really important thing. Anxiety is not gonna be appeased by reassuring reassurance. Anxiety is appeased by sitting with your anxious thoughts.

[00:10:00] Amy 0.: So I wasn't really gonna go here in this conversation, but I am now. Do you remember that story you wrote? I don't know, I think it was when you were in high school, and it was a story about describing the monster of ED, an eating disorder, in your brain. [Mm-hmm.] And when I say ED, I also mean like your anxiety disorder, right? Yeah. I mean, it was manifesting itself in anorexia, which was terrifying, but mostly it was the anxiety that was. Can you describe for us what it was like or still is, maybe on some days, when anxiety is in your head to that degree? Like, there's so little room.

Shawn O.: Luckily it's been a while since it's been like that. Um, but it's, uh, it's a living hell. It's horrific for any, any child ever. Your entire being is spent trying to prove you're okay and you don't fully believe it ever. No one should have to live in that anxiety.

Amy 0.:: So that is a perfect place for us to move to this whole idea of brave parenting. [Yeah.] How we can understand not only kids who suffer like you did, but the environment in which we're raising our kids and the things that we can do to help our kids understand that they're enough. [Yeah.] Build resilience, become independent, capable human beings. I know a large part of that conversation that we'll have is about my, our collective anxieties as parents. I know that because you and I have talked about it before, but be brutally honest about the things that you saw in me and in Dad, but also help me understand, help us understand the things that we've learned along the way that I've gotten better at that could have helped you then, that help you now, et cetera. Go back to your 12-year-old self if you can, which I realize is 13 years, help us understand what we can do as parents to avoid some of these pitfalls. 

[00:12:00] Shawn O.: I remember being a young kid and seeing you have what I now know as anxiety, and it, it looked brutal and it looked tough and it's something I didn't want. And it's something that like, [you mean anxiety about you and Luke?] No, I think you have big emotions just like I do, and you feel things deeply and some of those things can be really overwhelming and I don't think anyone is really taught how to deal with anxiety. And so I think I saw you kind of go through that and it looked really tough and I didn't want that. And so I really was looking to control my emotions so that I don't ever feel out of control with them. And I think what is better done now is saying, you know, having big emotions and feeling things deeply is an awesome thing to have. It is a great thing to have. It's awesome to have people like that in your life. And then it also comes with feeling things so deeply that sometimes they can get overwhelming and this world can feel overwhelming sometimes. And if you or dad would've looked at me when I was really worried that you weren't okay, or that whatever. And said, no mom's having big emotions. Sometimes this happens, you know how she dances around the house when she's feeling good. This happens sometimes when it gets, when you get anxious, like, this is the world that we live in. And feelings are tough, but feelings are great. We didn't have those conversations really 'cause, you know, no one really knew how to have those. And then I also saw the opposite of like, dad, who is not the most, like, you know emotional person. He doesn't like, [he doesn't dance around the house,] right. And so I was like, that looks a lot easier to me of just kind of going with the flow, doing things. I'm gonna try to do that, but I very quickly realized I feel things very deeply like you. And so I tried to avoid things that made me feel deeply because they felt [you tried to just like set aside those emotions.] For sure, for sure. I mean, I didn't read books that had love stories because they made me feel something that I was uncomfortable feeling 'cause it was big emotions. And even if they were good, they were overwhelming for my body 'cause I couldn't control that. And so I think that that's just a conversation of like, uh. If modeling to your kids that emotions are a good thing, feeling them is hard and important, and learning to support yourself through really tough emotions is such a big life skill that matters. I think if your kids see you prioritizing that and you caring about that, they're gonna care about it within themselves too.

[00:14:00] Amy 0.:So one time we spoke. I remember you saying to me that, I mean, I've done some work for sure on my own anxieties, and so I think you and I are in a much, much better place as adults and we've learned so many things, but one of the things I think that you noticed that I had learned is that like using those mantras to yourself as a parent, my kid is having a really hard time. My kid is really sad. My kid messed up. My kid isn't as good in the backfield as the other backfielder, and that's okay. And

Shawn O.: I think it's better said, uh, you know, whoever this kid is, my kid is a really good teammate. My kid loves his friends. My kid is so passionate about drawing. There are things that make your kid special, and it might not be that they're the best outfielder or they're the best, whatever. It's something that's very akin to your kid and that's really, really, really cool. The people who were, you know, who were the best basketball players, but really bad teammates were not, people I wanted to play with. People that loved being a part of a team, but you know, didn't have the skills but wanted to learn. So fun. And today I'm still learning how to be bad at things. When I go to the bar, I cannot play pool. Pool is not my game. I can't figure it out. It's not working. But I still try because I know it's really important to be bad at things and still try to do them and have fun doing them. And you know, I think that's a really important skill that goes along with just like resilience, right? Really, I'm still a fun person, a great person, even if I can't hit that ball in the pocket.

[00:16:00] Amy 0.: I liked your examples because I think it reminds us that if what we as parents value are things that are achievement oriented or accolade oriented or success oriented, then self-worth only comes if those pinnacles are reached. [Right.] But what you're reminding us all is look, self-worth is already here. [It's inherent.] Yeah. Your enough is already there. You're kind, you're sensitive. I think that's a really good reminder about how we could maybe find what really matters at the end of the day when we're parenting our kids.

Shawn O.: As an adult, having emotional intelligence is an equally important life skill as geometry, in my opinion, or maybe even more. School and sports test a very specific kind of like, can you do this well? Can you accomplish this? And if they do do that, well, I think we're, we're often a, a lot of us are like, wow, it's a really smart kid. You know, it's easy to do that, but then you forget that like even those really smart kids who couldn't socialize aren't gonna be happy adults. And that matters. You want your kid to be a happy, functioning adult, right? Not just one who can do really well in the corporate world, or one who's gonna be a really cool lawyer. That's also great, but you want them to feel like even when they lose that case, or even when they mess up that board meeting, they still matter. The things they think, the things they feel, matters and like feelings that matters. I really do love mantras and affirmations, but I think you need to remember too, like when you're a parent, you have to do it for yourself too. It's not just about your kid. I am a good parent. I am trying my best. It is really hard to be a parent. If you believe you're doing well, your kids don't feel like they have to prove that you're doing well by their accolades. [That's very well said] that my mom is okay even when I fail, so I'm okay.

[00:18:00] Amy 0.:I'm not letting my mom down even when I fail. [Right, right.] Yeah.

Shawn O.: And I even was told that by you guys. I knew you guys didn't care when I got off the soccer field if I did well, but I also knew that I needed that and, 'cause I never realized that like there was an inherently good part of me.

Amy 0.:So we gotta wrap this up fairly soon, but there's a couple little points I wanna hit on first. If you were to give advice to a parent whose child is, say, coming home from school, coming home from the soccer field, coming home from a play date, that would open the door to vulnerability, open the door to acceptance, open the door to anything but judgment. What kinds of things would you advise a parent to say or do?

Shawn O.: I think you can start with maybe something you've done that you enjoy throughout your day. I had a really good cup of coffee this morning. What did you do today that was fun? What did you do today that brought you joy? What was something crazy that happened today or wild? If you ask your kid questions of what brought you joy today? That kid's gonna respond with something you weren't ready for, and it's awesome. What's something that you noticed today? What's something that was really fun today instead of, you know, what did you get on that math test?

Amy 0.:What about, are you okay? Are you okay? Are you okay? Should I ask you about,

[00:20:00] Shawn O.: I think that really speaks to the anxiety that you had and the reassurance you were searching for and even if I as a kid didn't have the words for anxiety or reassurance, you know, kids are smart, kids get it. They're gonna know that there's an emotion coming from you and they're gonna wanna meet it. If one, you are okay within yourself, or like, you know, I'm a great person and I'm a great mom and I wanna know what's, you know, going on with my kid. If you're calm enough within yourself and you just leave the door open for the kid to find what they wanna tell you about, that's gonna be a lot better of a relationship. And your kid gets to share something they found fun with you and maybe they're gonna talk about some random Minecraft thing and like, that's a fun thing to learn about with a kid. Like you also see what your kid is finding fun and is weird and is different. I think like if we focus on, you know, sports and accolades and all the things that we know, uh, the kid, I think kids are also gonna pick up like, it doesn't matter if I have random free play with my, you know, friends, my, my parents wanna know whether or not I, did well in football.

Amy 0.:I'm gonna urge the importance of what I have learned later in my parenting journey, which is the default thought that my kids are all right. Instead of my default thought being, oh my God, I haven't seen, talked to my kid in a week. What's wrong? I am very slowly, I know Shawn, but very slowly, I'm getting to the point where the default is things must be really good and it feels really good, but how do we help parents get there much, much earlier? How do we help parents get to a place where they can say, you're right. You get to make that decision. You get to do that on your own. I'm going to trust. I'm gonna watch you go and do. How do we help parents get there? 

[00:22:00] Shawn O.: I think mantras and affirmations or whatever you wanna call 'em, is a great way to do that. And I think finding your own is really important. 'cause there is, you know, I'm gonna be okay. My kid's gonna be okay. My kid can do hard things. My kid can get through hard things. I have to let my kid make decisions. And I, I think it's also like, you know think back to when you were a kid, and I think parents love talking about how, you know, when we were a kid, we'd play outside all the time. We didn't have cell phones. But then you don't let your kid do that. You don't let your kid just go and figure it out and go run around you. You wanna know exactly where they are. You wanna track them. So you can't have your cake and eat it too. If you want your kid to be an independent kid and be able to play on their own and make new friends and do hard things and, um, you're gonna have to, uh, sit with your own anxiety that maybe it won't turn out well. And if it doesn't, then thankfully you're there for your kid. That's great.

Amy 0.:That's exactly where we're gonna end this conversation. And it's too bad we didn't have it when you were 12. Let me just thank you from the bottom of my heart and in front of all these people, I'm going to tell you how proud I am.

Shawn O.: Thank you mama. I love you there. You,

Conclusion

Amy 0.:Thank you for listening. If there's one thing I hope you take away from this conversation, it's this, connection does not require perfection. It's important to be vulnerable with your kid. You don't have to get the words exactly right. You don't have to fix everything. You don't even have to fully understand what your child is feeling in order to stay present with them.

[00:24:00] What matters most is creating space. Space to listen without correcting, to sit with uncomfortable or fearful emotions without rushing them away. And to let your child know that their experience is real and valid, even when it's different from your own. It's about truly seeing your child for who they are and what they are experiencing. Parenting the mental health generation often asks us to slow down when every instinct tells us to act. To stay curious when we want certainty. And to lead with loving response rather than reaction. So here's your action item for this episode over the next few days, choose one moment just to practice noting as we asked in our last episode, and now validating, instead of fixing. Notice how your child shows up. Notice what they say and what they don't say. Notice your own reactions. The urge to jump in, explain, solve, or minimize. And instead of responding right away, simply reflect back what you hear or see. That sounds really hard. I can see why that upset you. Thanks for telling me. That's it. No lesson, no solution, just presence. Because when kids feel seen and heard, they're far more likely to keep talking, and that's where real connection lives. Thanks for being part of this community and for doing the brave, imperfect work of parenting. We'll see you next time on Parenting the Mental Health Generation. We are really glad that you joined us to continue the conversation.