Raising Resilient Kids in a World That Makes Everything Too Easy

Summary

Podcast Summary: The Parent Chat with Dylan Dreyer

Episode: Raising Resilient Kids in a World That Makes Everything Too Easy
Date: April 16, 2026
Host: Dylan Dreyer
Guest: Vicky Wynn

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Main Theme

This episode explores how parents can intentionally raise resilient, independent children despite living in an age where convenience and comfort can make life too easy for kids. Dylan Dreyer and guest Vicky Wynn draw from personal experiences and parenting philosophies, comparing their different upbringings and present-day approaches, with a strong focus on open communication, “manufacturing” hardship, and embracing tough love.

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Key Discussion Points & Insights

1. Upbringing and Early Lessons in Resilience

• Different Childhoods, Similar Values

  • Dylan shares her experience growing up in New Jersey in a household where chores and respect for parents were non-negotiable (02:00-03:20).
  • Vicky describes being born in Vietnam, coming to the US as a refugee, and growing up with strict, authoritarian parents adapting to a new country (08:15-10:07).

• Cultural Perspectives on Tough Love

  • Food and shared meals seen as a love language, both in Dylan’s and Vicky’s families.
    • “In Vietnamese, the way you say I love you is, ‘Have you eaten?’” — Vicky Wynn (09:21)
  • Evolution of their parents into more openly affectionate grandparents is noted with surprise and humor (09:43).

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2. Parenting Philosophies: Chores, Allowance, and Responsibility

• The Role of Chores

  • Dylan makes her three boys do chores as a non-negotiable family requirement, not for allowance:
    “No allowance here, because these are just chores you’re required to do to live in our house.” — Dylan Dreyer (02:21)

• Allowance and Work Ethic

  • Vicky’s children do not receive a regular allowance; family contributions are expected.
  • Both moms discuss the importance of giving kids opportunities to earn money and see the value in work (31:13-32:21).
    • “My first job, I got 4 bucks an hour. [My daughter] got $15 an hour at the library.” — Vicky Wynn (32:07)

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3. Setting Boundaries and “Manufacturing” Hardship

• Moderating Material Comforts and Tech Use
  • Both mothers resist making life too convenient for their children, intentionally creating “friction” to build resilience (10:09-10:41).
    • “I add a little bit of friction, because how are they going to build any grit and resilience?” — Vicky Wynn (10:12)
  • Vicky’s oldest daughter is not allowed on social media, a conscious decision to delay those challenges (10:41-12:06).
  • The psychological effect of social media and the value of letting kids develop self-worth before external pressures set in is stressed (12:06-13:13).

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4. Parent-Child Communication

• Open Conversations vs. Old-School Silence

  • Both reflect on how their own parents avoided talking about tough subjects.
  • Vicky shares her approach of keeping all topics on the table, including sex, drugs, and relationships:
    • “My parents didn't talk to me about anything ... The answer was no. So that was all they needed to tell me.” — Vicky Wynn (18:30)
    • “I let them lead the conversation. Because if you put it all out there, nothing is taboo.” — Vicky Wynn (19:52-20:09)
  • Dylan uses gentle check-ins to invite sharing rather than asking direct questions:
    • “I never say, how was school today?... they’ll then bring up whatever happened” — Dylan Dreyer (20:16-20:24)

• Fears About Losing Connection During Teen Years

  • Both worry about maintaining closeness as their children hit adolescence (21:00-21:38).
  • Dylan admits, “I always hug Calvin. I just want you to always hug me, always in front of your friends...” (21:00-21:03)

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5. Letting Kids Learn from Hard Experiences

• Allowing Struggle, Encouraging Independence

  • Anecdotes include making kids talk to teachers themselves or follow through on difficult commitments.
  • Vicky’s story about her daughter quitting taekwondo stands out as a lesson in resilience:
    • “She did eventually have to have that tough conversation ... And I think she left feeling like, I’m a superhero.” — Vicky Wynn (14:21-14:57)

• Not Rescuing Kids from Every Problem

  • Letting children confront minor setbacks builds confidence for bigger challenges (14:49-15:26, 24:35-26:47).

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6. Gender, Stereotypes, and Future Partners

• Dylan admits to some traditional gender-role expectations and asks Vicky how she raises girls to value both independence and emotional expressiveness in potential partners (22:22-24:35).
  • “I do think that, like, chivalry should not be dead. I do like somebody to open a door for me...” — Vicky Wynn (23:55-24:02)

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7. Purpose, Service, and the Long View

• Vicky’s Hope for Her Children
  • “My hope for them is they live a life where they feel like they matter and they feel like they’re of service.” — Vicky Wynn (28:55)
  • She emphasizes the importance of struggle in building purpose and resilience—happiness is a byproduct of finding meaning in service to others.

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Memorable Quotes & Moments with Timestamps

• Parental Guilt-Tripping
  • “Like, I’m not above guilt tripping. I’m not above being like, mommy did these things for you, you know, to make a better life for you. Like, exactly. Like, they gotta remember who’s boss...”
    — Vicky Wynn (01:05; 21:14)
• Parenting Philosophies in a Nutshell
  • “Tough love is different because you’re teaching your kids how to be resilient, how to get through those hardships, how to find it within yourself to have those difficult conversations.” — Dylan Dreyer (34:02)
• Letting Kids Suffer Small Consequences
  • “They refuse to bring a jacket after you reminded them twice that it’s very cold outside. Let them.” — Dylan Dreyer & Vicky Wynn (30:26-30:42)
• On Discovering Purpose
  • “If you feel like you matter and you have purpose ... all the other stuff comes.” — Vicky Wynn (29:23-30:12)

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Notable Segment Timestamps

• [03:24] Introduction of Vicky Wynn and setting the stage for the parent-to-parent conversation
• [08:15] Vicky’s background: From Vietnam to New Jersey
• [10:07] Strategies for “manufacturing” hardship for modern kids
• [12:06] Social media boundaries and kids’ self-esteem
• [14:21] Daughters learning independence through difficult conversations
• [18:30] Differences in communication styles vs. prior generations
• [20:16] Practical ways to foster open dialogue with children
• [24:49] Letting kids “figure it out”—when to intervene or hold back
• [28:55] Vicky’s hopes and vision for her children’s adult life
• [30:26] “Let Them or Step In” parenting scenarios game
• [33:15] What makes Vicky feel she’s “crushing it” as a parent
• [34:02] Dylan’s closing thoughts on tough love and resilience

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Tone & Style

Warm, direct, candid, and often humorous. Both Dylan and Vicky mix heartfelt admissions of parenting doubts with practical wisdom, and their banter keeps the episode relatable and engaging.

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Conclusion

This episode offers a thoughtful, real-world look at why and how to raise resilient children—even when society makes it tempting to smooth every obstacle out of their way. It’s packed with actionable ideas, plenty of laughs, and heartfelt reminders that “doing hard things” pays off in confidence, purpose, and family connection.

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For further discussion:
Listeners are invited to DM their thoughts to @TodayParents or @dylandreyernbc on Instagram.

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Produced by The TODAY Show

Transcript

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[Dylan Dreyer]

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[Vicky Wynn]

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[Vicky Wynn]

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[Vicky Wynn]

I want to get that out there that it is cool to, like, appreciate your family, appreciate the sacrifices your parents have made for you. Like, I'm not above guilt tripping. I'm not above being like, mommy did these things for you, you know, to make a better life for you. Like, exactly. Like, they gotta remember who's boss, you know, at the end of the day. Right? Who made it all possible.

[Dylan Dreyer]

Right, Mommy? Welcome back to the show. So I don't know who else does this, but I actually make my kids do a lot of chores at home. Some would say I should make them do more chores, but I do let them do a lot of chores. And, you know, it's fun because I think they find joy in actually doing the chores. So, I mean, whether it's clearing the table, you can get that for Preston. Now, Ollie and Rusty like to see how many dishes they can actually clear away in one handful, which has now become dangerous at this point. Don't dry pet dish. But I made Calvin do his laundry. He asked for a shirt the other day. I'm like, well, if you're. If it's not clean, you got to go do the laundry. I do make them do things, and they don't get paid for it either. There's no allowance here because these are just chores that you're required to do to live in our house. Going really well. Don't drop all the crumb. I have this responsibility as a mom of three boys to turn them into three respectful, helpful, wonderful men. And that's why I love today's conversation, you know, Vicky Wynn, as a correspondent on The Today show. Well, she has three. Young girl, little older than my boys. They're 16, 14, and nine. And she is also trying to raise just independent, resilient young women. And it's funny how much we have in common, because I was born and raised in New Jersey. My dad grew up on a farm. She was born in Vietnam, and she was brought over when her parents escaped Saigon when she was just eight months old, eventually moving to the United States when she was 2. So she certainly has just a very different upbringing. But we were both raised in a way that we had to be respectful of our parents. We had to be helpful around the house. We had to kind of figure things out for ourselves. And I think it has turned us into very similar parents. So it's a really cool conversation. Take a listen. Thank you so much for chatting with us.

[Vicky Wynn]

I'm so happy to be on the parent chat with you, Dill.

[Dylan Dreyer]

It's so funny because, you know, during commercials and all that kind of stuff, like, we have about three to four minutes to just quick chat. What's going on with your life? You know? But this is like, our chance to kind of have a whole conversation.

[Vicky Wynn]

And I have a bazillion questions for you as the mother of three boys, because I have three girls, which we

[Dylan Dreyer]

are totally raising our kids in a different space because I've got three young boys. You have three girls slightly older. So you're, like, at that one level up from where I am. How do you feel? Like, how. How did you transition into that? Like, next grade?

[Vicky Wynn]

So, first of all, I am an only child, so having three kids is something that I did not ever picture for my. And they are right now 16. No, 14. One just turned 14. I know it changes every year. Hard to keep up.

[Dylan Dreyer]

Keeps track after a while.

[Vicky Wynn]

And then one's nine. So she's right in the age range of your boys. And I have to say, like, people were warned us teenagers, you're gonna have three teenage girls, and it's gonna be horrible. And I just think it is what you make of it, you know, I was prepared. I remember what I was like at 13. Like, how were you?

[Dylan Dreyer]

How were you? Like, it horrible.

[Vicky Wynn]

Like a terror.

[Dylan Dreyer]

Really, Tim, what way? Like, did you break the rules?

[Vicky Wynn]

I talked back. I broke the rules. I was rebel. And I really specifically remember it was 13. And now I look back and I wonder if it was hormones or what, like, made me, like, kind of lose my mind. It was just a lot of just acting out. And now I look back and I go, God, I was a terror. So I kind of prepared myself mentally for, like, 13 with the girls, but 13 came and went, and it was totally fine for my two older ones.

[Dylan Dreyer]

And I think it is 15, 16. Like, that's okay, too.

[Vicky Wynn]

I feel so lucky. And I think the key is if you. You kind of manifest what you want, right? So if you treat your kids with respect, but also have boundaries and you are still the authority figure, and you keep the lines of communication open. I think that was the key for girls. The little one, honestly, she's one third of the kids, like, 90% of the parenting. She's the baby, and she is wild.

[Dylan Dreyer]

Rusty takes up my energy, too.

[Vicky Wynn]

He's your littlest.

[Dylan Dreyer]

He's the youngest.

[Vicky Wynn]

Yes.

[Dylan Dreyer]

It's like, you know, the first one, you go into it, and you have all this patience, and you. You've read all the books, and you're so careful. You're so careful, and you're so mindful of their mental. Just mindful of everything. Then the third one, you're like, the other two are fine.

[Vicky Wynn]

Don't you think you're a better parent? Like, after the first two you've got

[Dylan Dreyer]

under your belt, you're like, I'm a more confident parent.

[Vicky Wynn]

Yeah.

[Dylan Dreyer]

I definitely, because of my lack of patience, I feel like I yell a little bit more at Rusty. And he's been doing this thing where he's like, I'm a bad boy. And it's like, I don't hear him say it at first. He's kind of, like, over in the corner doing. He's like, I'm a bad boy. I'm a bad boy. I was like, okay, like, record screech. Let's go talk this out.

[Vicky Wynn]

Does not break your heart.

[Dylan Dreyer]

It breaks my heart. Cause I'm like, did I overlook that he was mad in the first place, or did I just dismiss whatever feeling he was feeling? And I, you know, was focused on the other two more.

[Vicky Wynn]

So we talked to, like, parenting experts sometimes on our show, and one thing that stuck with me, that one of them said was that you like, that she would tell her kids, it's not gonna be fair. Like, everything isn't gonna be even Steven. But I can promise you, you're always gonna get what you need.

[Dylan Dreyer]

And I think back to the way my parents parented. My parents did something right. But then I also. If I were to describe my parents, it's like, it wasn't an overly loving house. I wouldn't say my parents got on the floor and played with me most of the time. It was us, just as kids, running around in the backyard. My mom would ring a bell for dinner and it was time to come inside. But there was always dinner on the table. Even when my parents kind of separated, we were all still together and we would all eat dinner together. But you've respected your parents. The type of person I was. My friends would call me and everybody's sneaking out of the house at 11 o'. Clock. So I called my mom and I said, mom, everybody's sneaking out of the house at 11. Can I go? And she's like, I'd really rather you not. I'm like, but Mom. But everybody's doing it. She's like, yeah, I don't think that's a good idea. So I. I asked permission to sneak out of the house.

[Vicky Wynn]

Hysterical. And she said no. Indeed.

[Dylan Dreyer]

You listen? No, and I listen.

[Vicky Wynn]

You did?

[Dylan Dreyer]

Yeah. I listened because I knew I was going to get in trouble. And there was one night where I just stayed out late and my parents never stayed up waiting for me to come home. They would be in bed. But I remember breakfast with my dad the next morning. He didn't say a word to me except a little late last night. And that's all he had to say because my dad and I would eat breakfast. He would make me breakfast every morning before school and I'd have coffee and toast and like, we talked and it was like, coffee. As a kid, I did.

[Vicky Wynn]

That's hysterical.

[Dylan Dreyer]

That was our moment together. And that one morning he wasn't talking to me. So that was all the punishment I needed because I'm like, I failed him, you know, I disappointed him. So, yes, it wasn't a lot of talking, it wasn't a lot of hugs. It wasn't a lot of like open love. But it was there 100% and I loved it. That about them. I'm definitely more huggy with the boys. I'm definitely more open about our feelings and all of that kind of stuff. But I'm curious for you what it was like, you know, being the daughter of immigrants to this country who just grew up in a totally different culture.

[Vicky Wynn]

I was born in Vietnam and my family and I came here as boat people. When I was like eight months old, my family escaped Vietnam. We were on a refugee camp in Malaysia for 10 months. So I came to the US at age two. So for the most part, I was really raised as a Vietnamese American kid. Like, my parents were sort of doing the best they could adjusting to like a brand new country and a place where people do things Very, very differently. But then they also had their own upbringing which was very strict, super authoritarian, like top down. You don't question your parents, what they say goes. They don't need to give you a reason. There is no like consideration for mental health. And you deal with it and you figure it out. If you bring up something like that, your parents are like, wait, we got on a boat, we survived a pirate attack. Like, what mental health issues are you struggling with? You know, 10 year old with access to McDonald's and KFC and Nintendo, like your life is good, right? We don't have time for this. It's so funny because like you talk about food and knowing that like you had breakfast with your dad or dinner, your mom had that for everybody. And I see that you're doing that now with your kids. That's definitely something you've carried over. Mealtime is so important and I think my parents were the same way their way and in a lot of like Asian cultures, Chinese, Vietnamese, Korean, whatever it is in Vietnamese means like, have you eaten? That's the greeting, that's the way you say I love you. It's have you eaten? Because if you haven't, I've got your favorite stuff. So that was always their love language. It still is. But now seeing them as grandparents and the I love yous and the I'm proud of yous that they say to

[Dylan Dreyer]

my kids, they actually say it.

[Vicky Wynn]

It's nuts.

[Dylan Dreyer]

Like, what the heck?

[Vicky Wynn]

Totally. I'm like, who are these people? Where did you come from? But I have to appreciate that they evolved as grandparents, you know, and so I am grateful for that. But I'm just like you. I talk way more openly with my kids. I'm very affectionate with them. I love yous are flowing left. And um, but I do try to find also some ways to manufacture hardship for them because it's not built into their liveship.

[Dylan Dreyer]

That's you don't purposefully make things hard for them. But like kind of a little bit,

[Vicky Wynn]

I should add a little bit of friction because how are they going to build any grit and resilience for us? It was built in like our parents were working, they weren't like there to solve every little problem. If they want to buy something, yes, we can probably buy it for them. But I try to say like, is that something that you need right now? What are you going to do to try to save up for it? Like, is it on sale? I don't know. I just try to add a little bit of friction. The biggest friction I Think I've added to my eldest is not having her be on social media. That's like a big line at all.

[Dylan Dreyer]

Does she fight you on that?

[Vicky Wynn]

You know what, luckily she's actually a pretty rule abiding, classic eldest daughter. And so she's recently did a, like a little presentation about why it would be great for her to have access to Instagram. And I just sit and listen to it. Listen, of course, always. Cause I'm always like, please present to me the data. Please like make the argument. We want it. But I also know I have a very unfair advantage because I've done the reporting, I've talked to the experts for a living. Exactly. So I'm like, unfairly, like way more prepared than she is. So I'm ready with my arsenal of facts and research and data, but I want her to make the healthy argument. So the way we left it was she made the presentation and then she was gonna revisit it with us, but then she never came back. She didn't do the follow up part. And I'm not gonna follow up on it.

[Dylan Dreyer]

She's not on anything.

[Vicky Wynn]

I know this.

[Dylan Dreyer]

Cause I know there's like another secret one that might scissor and all that.

[Vicky Wynn]

I'm like, I know that kids have that and I know, I'm not naive. Like, I know she's seen TikTok and YouTube and Instagram, like her friends, literally all her friends have it, but I do not believe she has it also because we have like her phone pretty locked down, you know, like, and there are no apps, like, hidden on her phone and she has screen time limits. And I. This may be the thing that like, you know, is her big cross to bear and the burden that she has of like, oh my God, my mom was so freaking strict, she wouldn't let me get on Instagram. But I also like what Matthew McConaughey said, which is you want to let them know and figure out who they are before the world starts telling them who they are.

[Dylan Dreyer]

Very good point.

[Vicky Wynn]

And I think especially for girls, but it's starting to happen with boys too. The body image, the self esteem, the anxiety, the depression rates, like, all of it goes up because they haven't figured it out yet. To like really just stay in their lane, run their race, live their life.

[Dylan Dreyer]

It's really hard not to compare to enough of it. As, I mean, Calvin, he's nine, he asked me, do I look fat? And I was like, what?

[Vicky Wynn]

That's insane.

[Dylan Dreyer]

First of all, you look healthy. We didn't have Instagram and social media growing up, but we certainly had that.

[Vicky Wynn]

Magazines. We had all of that.

[Dylan Dreyer]

We had all of that. So I do think it's one of those things where when, like, your kids are 25, they're like, thank you for letting me find myself before.

[Vicky Wynn]

That's what I tell myself.

[Dylan Dreyer]

I feel icky after I look at Instagram. I'm feeling insecure. And I'm not a very insecure person. No, I know my lane. I. I'm confident in my areas, but I'll watch Instagram. And I'm like, man, should I be going to Fashion Week? Because it seems like everybody I know here is going to Fashion Week, and I'm, like, starting to feel insecure about myself.

[Vicky Wynn]

And you're a full grown woman with a confident platform, and it still eats away at you.

[Dylan Dreyer]

I'm a great mom, but it still eats away at you. So I love that you can have that.

[Vicky Wynn]

All I'm trying to do is let her build the foundation as strong as it can be before all of this is unleashed on her. She goes to these conferences or whatever, and everyone's like, what's your Insta? And I'm like, well, then just get their number. And she's like, mom, that's so not cool. That is not. We don't communicate like that. We're not going to be texting. It's either Instagram or nothing.

[Dylan Dreyer]

And I'm like, it would bring a lot more success if you actually just exchange numbers. No, Totally out of coffee. Or whatever teenagers have. And, you know, brainstorm ideas, bring back

[Vicky Wynn]

the real conversations completely. So that's like, my main thing that I think I do to manufacture hardship is just, like, not to make everything so easy for them.

[Dylan Dreyer]

We spend all this time as parents stressing over how do we set up our kids for success. But you also have to realize they are their own person.

[Vicky Wynn]

Totally.

[Dylan Dreyer]

Our parents didn't give us these jobs.

[Vicky Wynn]

Nope, they didn't. My family manage it. They didn't, like, try to pave the way for us every which way. And what I'm finding. And I always like to talk to parents, like, who are. Have kids who are older than mine, right. To, like, get what's the jump on this or that. And I just find that, like, some of the parents who've told me their biggest regrets were making it too easy for their kids. They've never had to talk to, like, a teacher. So how are they gonna talk to a boss?

[Dylan Dreyer]

Yeah.

[Vicky Wynn]

One of my happiest moments that we had was my middle daughter, Odessa. She became a black belt in taekwondo. And then she just had so much going on with like SP and other things and it just wasn't something she wanted to keep pursuing. And we're like, okay, you know, we totally understand. You'll have to tell your teacher though. And she was like 13 at the time. Like, what? What do you mean I have to tell him? Like, she did eventually have to have that tough conversation and the teacher was amazing and he like thanked her and he said, I really respect you for telling me this in person yourself. And I think she left feeling like I'm a superhero. Like, oh my God. Like I did this hard thing after

[Dylan Dreyer]

you do something hard.

[Vicky Wynn]

Totally this hard thing I didn't want to do that I cried about. But then I did it and it just her feel like boosted her confidence. 10x right? So it's those things that it's hard as a parent to watch. You never wanna watch your kids cry, fail all the things. But these are small stakes. And I think when like they fail at the low stakes things, then it just builds their resilience and their muscle and gives them that thicker skin which we I think got by default. And then as parents, we have to remember to like, allow for it. Pull back, pull back.

[Dylan Dreyer]

We'll be right back after the break.

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[Dylan Dreyer]

Is there anything, if you look back and think where your parents were the most strict that you just really didn't agree with? Is there anything you specifically do not do because you didn't like the way your parents did it?

[Vicky Wynn]

My dad was a yes guy. My dad was like, always like a shrug his shoulders, like, why not? Type of like, whatever. My mom was very much like the no, no and no was. Her first response was like, no. You know, like, if it was a sleepover, no. If it was going to the movies, no. And so I think that was their thing. They didn't allow me a lot of freedom. Also, I was an only child, so they, I think were a little more like, eyes on, we gotta make sure, you know, we know where you are at all times. With my kids, I think I give them a lot more social freedom. But I'm also, I sort of understand the reluctance on sleepovers now that I. Because they never get good sleep. It's like you're a zombie the next day.

[Dylan Dreyer]

Next day's ruined.

[Vicky Wynn]

Totally.

[Dylan Dreyer]

You're waiting for the call all night to see if they're even gonna make it through the night. Right?

[Vicky Wynn]

So, like, I understand now as a parent, like, why my parents didn't love that so much. But the main thing I think I do differently is for sure the open lines of communication. My parents were like, they didn't talk to me about anything and like, sex, drugs, alcohol, you were gonna learn about that in school. And the answer was no. So that was all they needed to tell me.

[Dylan Dreyer]

Once I, I'm like, mom, like, what's a period? Should we have a conversation? She's like, don't you learn that in school? And I was like, yep. And that, that was that one time I walked into the kitchen and there was just like a, an electric razor on, on the table. And I was like, oh, I. I guess it's time to start shaving my legs. Like, we're not going to talk about it, we're not going to address it. And that's that.

[Vicky Wynn]

I learned everything from like Seventeen magazine and then later Cosmopolitan magazine that was like this, that was elevated a little bit racy one. So. Totally agree. The first period was like I looked at a box, I looked at the diagrams and I was like, I guess this is how you do it. Never to this day have talked to my mother about a period. But you know what? It made you resourceful, right? Yes, I do talk to my kids about all that. To the point where they're like, okay, really, like cringy, we're done.

[Dylan Dreyer]

How do you do it? How do you make sure that you can keep that dialogue open and that they will always come to you? Like, how do you do it? As they get older, I try to do it.

[Vicky Wynn]

Whenever, like I read an article or something comes up, I'll be like, oh, I heard this thing today. And then I'll just say, you know, whatever it was that happened, what do you think? And I just try to ask open ended questions and I let them take me where they want to go because that allows them to sort of lead the conversation. Because if you put it all out there, it's like a big old smorgasbord.

[Dylan Dreyer]

Yeah.

[Vicky Wynn]

They're like, oh my God, my mom will talk about anything. Like she'll just go there. And so then nothing is taboo. Right? So I think that's my approach.

[Dylan Dreyer]

I've noticed this magic when I pick the kids up from school and they get in the car, I never say, how was school today?

[Vicky Wynn]

Yeah, you don't put them, you don't

[Dylan Dreyer]

put them on the spot. They will then bring up whatever happened in school today. It's just like this dance. And again, a dance I didn't have with my parents. I wasn't talking to my parents about it.

[Vicky Wynn]

They weren't taking you to the dance. They weren't asking you to the dance. They were like, you stay out there. You're not welcome on this dance floor. No, totally agree. Yeah.

[Dylan Dreyer]

Do you find, I mean, and I'm asking because my kids are still so chatty as they get older into their teens. Do you notice they do pull back? Like, I always hug Calvin. And I'm like, like, I just want you to always hug me. Always in front of your friends. You always have to love me and you always have to be so proud of me as your mom. And it's like, but I love that

[Vicky Wynn]

you tell him that. Say it. Say what you want.

[Dylan Dreyer]

But I worry, you know, once they hit that funky age where they're like, you know, oh my God, it's too

[Vicky Wynn]

cool for mom and whatever, you know,

[Dylan Dreyer]

12, 13, so scared about that age.

[Vicky Wynn]

Well, I want to get that out there that it is cool to like appreciate your family, appreciate the sacrifices your parents have made for you. Like, I'm not above guilt tripping. I'm not above being like, mommy did these things for you, you know, to make a better life for you. Dang it. Exactly. Like I'm okay with that. Like, I think those things are fine. I think I believe in like a mix of like you're empowering them and stuff. But like they gotta remember who's boss, you know, at the end of the day. Right. Who made it all possible.

[Dylan Dreyer]

Right. Mommy. And I do think it's different for us with our kids. Like, I wasn't friends with my parents and I find I'm a little more friendly with my kids. Like we can laugh and joke and their friends come over and I'm teasing and I'm joking, you know, And I'm like so myself.

[Vicky Wynn]

Yes, yes.

[Dylan Dreyer]

But I don't know how that plays out because I haven't yet seen it.

[Vicky Wynn]

Like one of daughter has her friends over, like, whatever. Like I'm there, I'm providing the food and the snacks, I'm checking in on everybody and then I'm out. We got into it the other day because I was like, who's the coolest mom of all your mom friends? And then my husband's like, well, I think they might think so and so is cool. And I was like, what? Like, oh, I was so mad at him. I'm like, oh, how dare you even suggest that someone else's mom is cool. Like, even if you think that in your heart of hearts, you never verbalize that. Like, you need to be like, your mom is the coolest mom. Like, what?

[Dylan Dreyer]

I'm curious. As your girls are getting older and I'm trying to raise three young boys, I tend to be stereotypical male, female. Right. Like I think the men should take out the garbage and I'll clean the dishes. Right. Like I'm just kind of old fashioned. It's how I grew up. Right. I mean, my dad was a mechanic, my mom was a secretary.

[Vicky Wynn]

Like it was, yeah.

[Dylan Dreyer]

Like literally right in the box as you get. So as your girls get older. And I'm thinking of your oldest, she's

[Vicky Wynn]

16, 16, almost 17.

[Dylan Dreyer]

So as she starts dating or finds interest in other boys, I mean, like what kind of of boys would you want her to be interested in? Like how Can I raise the ideal boyfriend? I guess is what I'm asking.

[Vicky Wynn]

Still, this is the biggest conundrum of my time. This is also why I care so much about boys, right? And, like, this is under the assumption that my girls will date or marry a boy. Like, I have to keep an open mind. It could be, I don't know what.

[Dylan Dreyer]

It's whatever they want to do. But as of right now, as of

[Vicky Wynn]

right now, let's say they do end up with a boy. Like, I do think they have a great role model in their dad. And I do think that, like, I want them to end up with a boy that is aware of his emotions, like, is able to communicate. What I hope the girls will get and what I'm hoping, like, the boys of this generation will grow up to know and master, is the ability to communicate, but also to know that it's okay to, like, pursue the things that they want to pursue and be, like, the protector and to, like, be like, kind of like the gentleman. Yeah, like the gentleman. Like, I think that, like, chivalry should not be dead. I do like somebody to open a door for me or help me with a box or, you know, I think

[Dylan Dreyer]

my dad opens the car door for his wife and it's just like, he walks to that and it's like, man, I need to teach that kind of stuff.

[Vicky Wynn]

I think that's super charming and wonderful. And I think that, like, that's what I hope the girls will have is someone who sees them as an equal, but also isn't afraid to do the things that are associated with being a man and, like, masculine. But I do think that it's nice that this generation can talk about their feelings. I think that's really important because I think boys for a long time were told, stuff it down. You gotta be a man. Like, that means no tears. That means no, like, being sad, no, like crying and this and that. And I just think, no, I think we want you to be in touch with your feelings and be able to talk about them, but also know that, like, some of the responsibilities in the world fall to you.

[Dylan Dreyer]

You know, we can always give advice, but sometimes, like you said, tough love, we have to kind of pull back a little bit. Has there ever been an incident with one of your daughters where you really had to just bite your tongue and just let her figure it out.

[Vicky Wynn]

My oldest, when she first got to this new high school, she joined the cross country team because we were like, you got to do something, like after school, just whatever it is in the fall, the sport is cross country or it's field hockey. It's like running or running with a stick. You pick, right? And I'm not a runner and my husband's not really a runner. And she was like practicing and then she came home and she was super upset, like crying. And my oldest does not cry like that often. But they had a meet coming up and she really wanted to quit. She was like, this is so hard. I'm so slow. I'm the last one. It takes me forever to run these three miles, whatever it was, all this. And I was like, I wanted to just let her quit because I'm not a runner. And I felt bad that I was making her do something that I myself don't even do or can't really do. And it just was such a mixed bag of like she was hurting and really didn't want to continue this thing. And I was willing to let her. And I am glad that I didn't have to make the decision by myself. And if I had, I would've said, go ahead, you can quit, you can stop. My husband was like, why don't you just stick it out through the one me and. But it was so hard. Cause I was like, we got into a fight about it. Cause I was like, she is suffering. Like we were having her do something that like is horrible, right? And like she hates it so much and like she never cries and this is awful to watch. But she did the meet, she was fine. She didn't come in the last place or whatever. And like she's now like a three season runner. As a junior she has won like last year her team won like the state championship. Like she's become a runner. Like that's her identity. It's such a big part of her life. And I feel like, man, I almost like let her quit that thing. And I'm glad that someone else talked me out of it. But it was one of those situations where you're like, sometimes you have to just let your kids do the hard thing, make them do the hard thing, and then they will see that, like they can do it, that they actually can do it. And that's like the best gift you can give them. But it was really hard. That's definitely a time where I felt like, man, I would have made the wrong call. I would have made the wrong call by getting involved.

[Dylan Dreyer]

More of the parent chat after the break.

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[Dylan Dreyer]

Hey everyone, check out this guy and his bird. What is this, your first date?

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Oh, no.

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We help people customize and save on car insurance with Liberty Mutual together. We're married. Me to a human, him to a bird.

[Vicky Wynn]

Yeah, the bird looks out of your league.

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Anyways, get a [e-mail] or with your local agent.

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[Dylan Dreyer]

What do you hope for your kids as they grow up, being raised the way you're raising them?

[Vicky Wynn]

So my hope for them is they live a life where they feel like they matter and they feel like they're of service. I think that actually is like really important to your well being. Like, people go, oh, I want my kids to be happy. And I used to think that too. Oh, I want them to be happy, you know, like and financially successful and independent and whatever. But I realize that actually like all of those things I think will be the side effects and byproducts of a person who feels like they're contributing and feels like they matter. Matter. Because if you feel like you matter and you have purpose and you're like living to help everyone else and like, you know, you have a role in the world other than just serving yourself, all the other stuff comes. Yeah, right. Like, I just think that that's really important and especially in our society and especially with some of the role models we have, it seems like it's like this. You got to get to the top, you got to get the money, you got to get the fame. You got, Whatever. What's next? What's next? And I'm like, there are so many ways to find a peaceful, purposeful life that don't have anything to do with that. So I just want them to have really broad horizons and to find out who they're meant to be and to feel good about that. And that's not to say that that doesn't come with some struggle and strife. I think that that's important too. Like, I think hardship is what builds resilience. So I don't want to remove all the obstacles for them. But ultimately I think I'll feel like a great parent if I look around and I see that my kids are making the. Their little corner of the world better in some way.

[Dylan Dreyer]

Yeah. I love. That's so well said.

[Vicky Wynn]

Thank you.

[Dylan Dreyer]

Okay, so we're going to play a little game.

[Vicky Wynn]

Game. Okay.

[Dylan Dreyer]

See, we've got let them or step in. Oh, okay, okay, cool.

[Vicky Wynn]

I love this.

[Dylan Dreyer]

Okay, I'm going to read you some of the options here.

[Vicky Wynn]

All right?

[Dylan Dreyer]

Okay.

[Vicky Wynn]

Okay. I'll put my right hand. Let them. Because it's probably going to fire up more.

[Dylan Dreyer]

Okay. They refuse to bring a jacket after you reminded them twice that it's very cold outside. Let them.

[Vicky Wynn]

This happens all the time. Let them. Yes, let them. But then I end up having to give them my beanie or something. Right. But like, I let them.

[Dylan Dreyer]

Yeah, I do too. And it's hard with the 4 year old because I don't think he actually understands like, what cold is.

[Vicky Wynn]

Right, right, right.

[Dylan Dreyer]

But no, I'm gonna let you.

[Vicky Wynn]

Yeah.

[Dylan Dreyer]

All right. This one we kind of just talked about. They wanna quit a paid activity halfway through the season because of whatever reason, do you step in or let them struggle?

[Vicky Wynn]

Oh, step in. Step in. Say you're gonna finish this out. Mommy paid good money for this.

[Dylan Dreyer]

Yeah, yeah, right?

[Vicky Wynn]

It's not even an option.

[Dylan Dreyer]

It's not even an option.

[Vicky Wynn]

They know not to even.

[Dylan Dreyer]

They actually paid for it themselves.

[Vicky Wynn]

Ooh. I have not had the luxury of that experience yet.

[Dylan Dreyer]

That's true. At what age do kids start paying for things themselves?

[Vicky Wynn]

I don't know, 21?

[Dylan Dreyer]

No. Like, what is the rule there?

[Vicky Wynn]

I, you know, honestly, I think that there's more skin in the game though, if they do have to contribute.

[Dylan Dreyer]

Right. Because then they see your struggle and why you're forcing them to do it.

[Vicky Wynn]

Totally.

[Dylan Dreyer]

Yeah. Okay. They say, can you just buy it? I'll Pay you back. Do you step in or let them struggle? Because will they ever really pay you back?

[Vicky Wynn]

I know. I don't expect. See, this is like, I. What is it? I step in and. Does stepping in mean pay? I struggle with this one. Dylan. I don't know how you handle allowance and all of that. You said they do some paid chores, which I think is good.

[Dylan Dreyer]

Well, the paid chores are on the table. They're not actually doing them.

[Vicky Wynn]

Yeah, okay. Oh, but they're on the table.

[Dylan Dreyer]

They're on the table.

[Vicky Wynn]

That's good. Here's ways to do that.

[Dylan Dreyer]

You can make money.

[Vicky Wynn]

I'm going to add that. I'm going to add ways to make money. Because the oldest, we did make her get a job at the library. Like, she got $15 an hour. My first job, I got 4 bucks an hour. 15. They're paying minimum wage. That was a lot of money. Seriously.

[Dylan Dreyer]

Yeah.

[Vicky Wynn]

But she doesn't really have to buy too much of her own stuff, because I think the contract we have with our kids is like, you do your homework, you do your schoolwork, you do your sports, you fulfill your end of the job, and when you need things, things were there for you.

[Dylan Dreyer]

Right.

[Vicky Wynn]

But we're getting them on sale. That's the compromise.

[Dylan Dreyer]

Do you give an allowance?

[Vicky Wynn]

I don't.

[Dylan Dreyer]

I remember when I asked my dad if I can have an allowance, he's like, are you out of your mind? You live here, don't you?

[Vicky Wynn]

Right.

[Dylan Dreyer]

It's like, okay, Right, I'll stop asking. Yeah. Okay. Last one. They want to quit their summer job because they just don't like it or it's too much drama or it's too hard. Do you step in and let them, like, no quitting. No quitting.

[Vicky Wynn]

Sorry. You signed up for this thing or we signed you up for this thing. Whatever it is, we're gonna see it through.

[Dylan Dreyer]

Yes.

[Vicky Wynn]

Seeing it through just builds so much charact and, you know, like, unless you're. My big thing is injury. Like, if you're at risk of injury,

[Dylan Dreyer]

then, okay, you're breathing like fumes at your place of business. Then maybe, okay, I'll let you quit.

[Vicky Wynn]

If it's an OSHA violation, maybe I'll let you quit. Otherwise, you work that job.

[Dylan Dreyer]

Yeah. So let's end on a high note here. Can you think of anything recently that made you feel like, man, I'm really crushing it as a parent?

[Vicky Wynn]

Ooh, ooh. I'm so happy that I have three kids who do talk to me, who do have fun with me. Like, that's A win for me that like I mess with them, tease them. We have inside jokes. Like they say that every family has its own language, you know, because it's all the shared experiences that you have and like the funny words that you come up with or like how someone mispronounces something and now you always say it that way. That makes me the happiest when I think I am actually able to be a good mom because my kids are alive. I like low bar there. But also they seem to be thriving. They seem to be pretty, like happy, go lucky, fun loving, good kids who, who try to like, look out for the people around them. I love that they could be nicer to their little sister.

[Dylan Dreyer]

Yeah. Well, I'm so glad we had than three minutes to tell.

[Vicky Wynn]

Amazing.

[Dylan Dreyer]

Way better than a commercial break.

[Vicky Wynn]

Exactly.

[Dylan Dreyer]

I love when I can have a conversation with someone that I just connect with. There's always love. But tough love is different because you're teaching your kids how to be resilient, how to get through those hardships, how to kind of find it within yourself to have those difficult conversations that you need to have. It just makes them stronger. And it's hard to do sometimes because we do really want to protect them from everything. But sometimes, like Vicki said, you just have to step back, you have to bite your tongue and let them go through it. And it was just fun to connect with Vicki on that. DM us on Instagram today. Parents or Ylan Dreyer, NBC. Let's keep this conversation going. I'd like to know your take on the whole thing. We'll see you next time. Bye. Bye. This episode was produced by Ann Legamayo with Virginia Video production by Andy Tavares. Rachel. Paula Abramson is our parenting reporter. Our senior producer is Tyre Nobles. It was edited by Ali Strain. Our audio engineer is Joe Plord. Our head of audio production is Jessica Fenton. Ashley Domagola is our production manager. Sadie Bass is our supervising producer. Ariana Davis is the executive editor of the Today show. And Ashley Kodiani is the vice president of content strategy. I'm Dylan Dreyer and this has been the Parenchat, a production of the Today Show. See you next week.

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