Baby Steps to Big Kid Independence

Summary

This Is So Awkward – "Baby Steps to Big Kid Independence"

Hosts: Dr. Cara Natterson & Vanessa Kroll Bennett
Date: May 5, 2026
Main Theme:
This episode explores how children develop independence—especially physical independence—during the long stretch of middle childhood into adolescence. With candor and humor, Dr. Cara Natterson and Vanessa Kroll Bennett discuss the hurdles, anxieties, milestones, and practical skills involved, while recognizing the emotional and developmental complexity for both kids and parents in navigating this journey.

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Key Discussion Points & Insights

1. Setting the Stage: The Shift from Dependence to Independence

• Context: Childhood is now a "decade of prime time" for building independence, spanning ages 8–18.
• Distinguishing Autonomy vs. Independence
  • Vanessa: “Autonomy is essentially more of, like, a larger sense of agency and identity, which is obviously really growing and expanding during these years. Independence is more of a kind of tactical reality, an ability to function on your own.” (03:23)
  • Cara: “This episode is very specifically about that kind of, as you said, boots on the ground... when kids venture out physically on their own.” (03:49)
• Parent Reflection: Vanessa openly discusses her impatience and regrets during her children's early struggles for independence, highlighting that parental growth is a parallel journey. (06:09)

2. Early Independent Milestones: The “Gross” and the Gritty

• Milestones include: Potty training, shoe tying, feeding themselves, walking alone, etc.
• Parental Discomfort & Growth:
  • Cara: “We didn't have the muscle, and we had to grow the muscle first.” (08:21)
  • The value of making mistakes and learning alongside your child was emphasized.

3. Culture, Community, and the Free-Range Debate

• Different Norms:
  • Vanessa notes variance between neighborhoods (some with abundant independent walkers/bikers, some with car pickups).
  • Generational shifts: Stories shared of children (including 5-year-olds!) riding NYC buses solo in the '60s vs. the more protective present.
• The Free-Range Kids Movement:
  • Cara: Regarding Lenore Skenazy, “She was kind of skewered for it in the name of stranger danger and all the things that could go wrong. And she pushed back hard and basically said, how am I going to raise an independent kid if I don't give my kid independence?” (13:30)
  • Polarized parental opinions highlighted.

4. Foundational Skills for Physical Independence

• Walking Alone: Crossing streets safely, not looking at phones, reading the environment, self-advocacy if something goes wrong (20:25)
• Parental Anxiety:
  • Stories of real-life traumatic pedestrian accidents heighten fears and reinforce the need for safety training.
• Managing Anxious Kids:
  • Cara: “For the anxious child, that skill building does turn up the anxiety... How do I help my child who runs anxious manage this very important foundational skill?” (22:01)

5. Building Independence Through Social Experiences

• Carpooling:
  • Kids must learn social skills and adaptability in different family environments—the infamous story of a child falling out of a carpool car in the '70s (24:53).
• Sleepovers & Sleepaway Camp:
  • These are deeply contentious milestones, with strong opinions about age and safety.
  • Cara: “You send kids away to summer camp to build their independence, to build their resilience, to give them joy... But you don’t have to do these things in order to gain independence.” (27:31)
  • Unique family circumstances (cultural norm, trauma, logistics) influence readiness and approach.

6. The Role of Technology in Independence

• Tech as a Double-Edged Sword:
  • Phones can enhance safety and parental peace of mind, but are a distraction and safety hazard (walking while texting, etc.).
  • Vanessa: “There is the big debate: if my kid is moving around on their own, do they need a phone?... I think it's less about what is the right decision and having a thought process and a reason why you’ve made the choice.” (45:04)
• Location Tracking:
  • Vanessa: Uses tracking sparingly and with transparency; stresses it should not replace communication skills.
  • Cara: “They see it as a passive form of communication: ‘What do you mean I need to communicate with you? I’m already communicating with you. You know where I am.’” (51:05)

7. Decision-Making, Peer Pressure, and Gray Zones

• Constant Conversation & Role-Playing:
  • Kids need practice making decisions before they’re faced with consequential ones (e.g., safety, peer influence, resisting risky behavior).
  • Cara: “Here’s the gray zone: for any given one of these things, like, I don’t know. I don’t know if my kid is ready... Where does independence building fit into all that? That's messy. That's gray.” (37:08)
• Different Kids, Different Approaches:
  • “The kids are raised in the same house. My decisions for my different kids were different. Their ability to assess safety, to communicate and to make decisions was different.” (48:53)

8. Letting Go: Parent’s Emotional Journey

• Recognizing Parental Baggage:
  • It's vital to separate one’s own anxieties and traumas from the child’s developmental needs.
  • Finding other adults to discuss fears with (friends, therapists, partners) helps keep challenges in perspective. (32:36)

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Notable Quotes & Memorable Moments

• “Can you imagine today if you saw a five year old boarding the M86 bus... you'd be like, no. Where is this child's parent?” — Vanessa, (01:11 and again 33:42)
• “There's a right answer here, Vanessa. Like, spoiler alert. The right answer is you want your child to be able to grow into a young adult who can stand on their own two feet and who can depend upon themselves and trust in themselves.” — Cara, (08:38)
• “I was always rushing my kids instead of, like, just, like, hanging out, letting them, like, tie their shoes incompetently... I did take that lesson as I approached this next stage of life.” — Vanessa, (06:09)
• “If a kid can’t learn to walk on their own from point A to point B, the other things we’re going to talk about are really hard for them to do on their own.” — Cara, (14:37)
• “Different families, different rules, different attitudes, you know, all of that stuff.” — Vanessa, (24:24)
• (On using tech for safety): “I really try not to use it because I’m really trying to build their skill of communicating with me and me communicating with them.” — Vanessa, (49:27)

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Timestamps for Important Segments

| Timestamp | Topic/Quote | |-----------|---------------------------------------------| | 01:01 | Humorous contrast: 5-year-old bus rider then vs. now | | 03:35 | Definition of autonomy vs. independence | | 06:09 | Vanessa’s parenting regrets & growth | | 13:30 | Free Range Kids Movement introduction | | 20:25 | Foundational skills: Street safety | | 22:01 | Special challenges for anxious children | | 24:53 | The carpool anecdote (falling out of car) | | 26:44 | Controversy about sleepovers/camps | | 32:36 | Managing parental trauma and anxiety | | 39:02 | Peer pressure and building the ‘right choice’ muscle | | 45:04 | Tech/phones and independence debate | | 49:27 | Tracking: transparency & communication | | 51:13 | Transition to adult privacy/respecting boundaries |

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Skills and Capabilities Required for Independence (49:47)

• Personal safety and situational awareness
• Communication (especially when trouble arises)
• Decision making and resisting peer pressure
• Listening to intuition and making snap decisions
• Practicing independence at the right pace for each child

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Closing Thoughts

Across different family cultures and with uniquely individual children, independence must be gradually, intentionally fostered. Cara and Vanessa urge parents to examine their own baggage, maintain dialogue, and remember that the goal is not avoiding discomfort, but equipping kids for eventual adulthood: “They have to become independent… In service of becoming independent, what are the capabilities that they need to acquire over this decade?” (47:25)

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Listener Call to Action:
Send in your stories, questions, and insights about how your family approaches independence, the struggles you’ve faced, or creative solutions you’ve found.

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For more resources and community:

• lessawkward.com
• Newsletter and bonus content via This Is So Awkward

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Summary prepared for listeners seeking a practical and empathetic perspective on raising independent kids in today’s world–removing the cringe, building confidence, and embracing both the awkwardness and the triumphs along the way.

Transcript

[A]

Kara. At Great Wolf Lodge, there's adventure for the whole family. I'm excited to check out the lodge in the Poconos, which is close to me. And with 23 lodges across the country, there's probably one near all of you too. You and your pack can splash away in the indoor water park where it's always a toasty 84 degrees. There's a wave pool, a lazy river and a bottle. Bunch of massive water slides, including ones your family can enjoy all together.

[B]

They even have adventure packed attractions from Magi Quest, a live action game that kids can play throughout the lodge, to the Northern Lights Arcade. And there's also a bunch of great dining options and complimentary daily events like nightly dance parties all under one roof. So bring your pack together at a lodge near you. Learn [e-mail] that's G-R E A T W O L F.com and strengthen the pack.

[A]

I have a friend who grew up in New York city in the 60s and he rode the crosstown bus by himself at 5 years old.

[B]

Oh my God.

[A]

I mean, can you imagine today if you saw a five year old boarding the M86 bus, you'd be like, no. Where is this child's parent? Hi, Cara.

[B]

Hello, Vanessa.

[A]

So one of the really interesting parts of the the universe we sit in, the sort of tween and teen universe, is the way it intersects with kids burgeoning independence. It's like prime time for transitioning from being really quite dependent in almost every way on a parent or caregiver to really being not entirely independent, but really quite independent from a parent or caregiver.

[B]

And a decade of prime time.

[A]

Yeah, so a decade of prime time, which is kind of a long time to be in prime time. So prepare yourselves because we're going to talk about what that decade looks like and why it's so important to support it and engage with it and be patient with it, which frankly is not one of my best qualities in this context. One of the things that often gets confused is the concept between autonomy and independence. Right. We're talking about kids burgeoning independence, but part of that is their sense of autonomy. And we talk a lot about bodily autonomy, Cara. Like kids feeling like they're in charge of their bodies, they own their bodies, they get to say who touches their bodies and who doesn't touch their body, that they learn how to take care of their bodies. You know, all of those things. We talk a lot about that, but we don't. Haven't talked as much about autonomy in the broader sense of the word, except in our conversation with Emily Edlin about autonomy, supportive parenting. So if you're super interested in that topic, go back and listen to that episode with Emily, which is. Which is wonderful. And she wrote a book by the same name. But autonomy is essentially more of, like a larger sense of agency and identity, which is obviously really growing and expanding during these years. Independence is more of a kind of tactical reality, an ability to function on your own. A kid's growing sense of their capacity to do for themselves, go for themselves, you know, all of those things. So I like to think of them as one is more kind of conceptual and identity based, and the other is sort of more boots on the ground.

[B]

Tactical. Right. I mean, it's literally boots on the ground. It's physical independence. So there are lots of different kinds of independence that we've talked about on this podcast over the years, but this episode is very specifically about that kind of, as you said, boots on the ground. Like when kids venture out physically on their own and what the skills are that they need to have, what the hurdles are that we need to get over, what fears we need to put aside, what realities we need to embrace. I mean, there's. There's a lot to this, and it is not without a lot of public drama. I mean, we'll talk about the free range kids movement and the role that that played in physical independence. But let's start, Vanessa, from the beginning, let's help people sort of frame the conversation around venturing out into the world by reminding them, you have done this with your kids for a long time. This is not a new muscle. It's just being flexed in new ways. But, like, I mean, I always think about the before times and the after times as tethering to when my kids were mobile. The before times, I just carried them around. I controlled everything I like. They were not. They didn't have hands everywhere, up their nose, on the floor, licking the airport seats, all the things, right? And then that move to mobility, all of the safety and security in the bubble that I had created when they were strapped to me or when they were in a car seat or in a stroller, that was gone. And that really, that sort of crawling, if you're my kid, you scooted walking. That was the first time you, as a parent or a trusted adult had to deal with independence. And it was gross. Like, let's be honest, it was like there was. There was such a fear factor about the danger they were going to get themselves into, and there was such a Disgustingness factor. But, like, you did it, you've done it. And if there's a learning curve that's the steepest in all this, I would argue that was it. You're. You're over the hard part.

[A]

I mean, it's, you know, was everything from potty training to shoe tying to feeding themselves. And I found it utterly maddening. I mean, Kara, I. I wrote a chapter in my book about how terrible I was at helping my kids through this stage of life. Like, it's a mea culpa because I sucked at it. Like, I was so impatient. I was always like, I can do this better. I can't stand this. This is endless. Like, and, you know, we were recently at an. At an event and a parent asked about sort of a related question. And I was just talking about, like, how much regret I have that I was so impatient and I was always rushing my kids instead of, like, just, like, hanging out, letting them, like, tie their shoes incompetently, you know, Like, I just, like. So I did take that lesson as I approached this next stage of life. And, you know, in fact, I mean, yes, as you mentioned, there are high stakes when little kids start moving around. They. I remember in New York City raising kids when some kid would make a runner for it and disappear from the playground, and all of the parents and babysitters in the playground would mobilize to, like, find that kid. It is terrifying. But when they get older, frankly, it gets even scarier in many ways. And yet. And yet we got to do it. We got to teach them. We got to empower them. We got to let them go. We got to let them walk and run and drive and fly and, like, do all those things in the way that suits them best, in the way that suits us best. Right? So this conversation is going to cover a lot of ground, and it's going to vary depending on your kid and your family and what's happened to you in the past and your own baggage, truly baggage, because a lot of people have, like, their own traumatic experiences. So I want to own the ways in which I sucked at this when my kids were younger and how I learned from that to be better at it as they got older, even knowing all the fears that are wrapped up in this.

[B]

I'm going to reframe your sucking at it language. And I'm going to say that's my point is we didn't have the muscle, and we had to grow the muscle first. So everyone who's listening, I mean, unless you were, like, a natural Baby whisperer, and then you learned it somewhere else in your past life, and you flex the muscle. Then maybe you were a teenage babysitter and that's when you learned it, or you had a much younger sibling. But, like, we had to learn it somewhere, and we learned it when our kids were small. And so now the question is, like, how do you take this knowledge and where do you go from here? Because on this podcast, there are so many rarely right answers or scientific answers that are correct and data proven. But, like, they're so rarely right answers about a lot of this stuff. There's a right answer here, Vanessa. Like, spoiler alert. There's a right answer. The right answer is you want your child to be able to grow into a young adult who can stand on their own two feet and who can depend upon themselves and trust in themselves. I mean, you know, I will flash forward to one of my own kids who just had a relationship breakup, and what went from a really sad phone call one night the next morning flipped into a conversation about, wow, I have this incredible network of friends. And this is what so and so did, and this is what so and so said. And it was an unbelievable recognition that they were independent. They had built that on their own.

[A]

Right.

[B]

This was their support network. So, like, we're good. We're good.

[A]

Thank you for the generous reframe of. You're welcome. Early parenting failures. You're welcome.

[B]

You were great, Vanessa. I didn't even know you, and you were great.

[A]

But, you know, I was fabulous. You were fabulous.

[B]

But let's get into, like, what are the milestones? Like, let's start with. Let's start of grade school. Right?

[A]

Right. So what's interesting is. And I was. I was actually literally just thinking about this as I was walking my dog before we got on this recording, because

[B]

that's so independent of you.

[A]

Occasionally I manage. And I was at the end of my street is a bus stop, and there are. Every afternoon, if I'm out walking my dog, I see people driving to the end of the street to meet the bus stop, to drive their kids basically to the. The other side of my neighborhood. And I was.

[B]

Which is not a particularly busy neighborhood

[A]

because I've been not a particularly busy neighborhood.

[B]

There are very few cars, not a

[A]

lot of cars on the street. And I was thinking about it. I was like, this is so interesting. Like, when I was growing up, the kids would have gotten off the bus and walked to their homes. And, like, I mean, not to be judgy, but one of the people whose Car I recognize because they drive too fast in my neighborhood, and I know exactly who they are, and they live probably the equivalent of four or five blocks from the bus stop, and they pick their kid up. And I was like, you know, when we were kids, we would have just walked. Nobody was gonna pick us up. Maybe we would've walked in pairs, maybe not. In New York City, where I raised my kids for many, many years, starting in sort of like fourth or fifth grade, the kids would have just walked. So I'm struck by the picking kids up, old enough, in my opinion, to be walking on their own and physically have the capability of walking on their own. And I was like, is this representative of. Because my sister lives in another town, and in her town, all the kids are on their bikes or walking, or they're all moving around on their own, or at least it seems like there's hordes of children moving around on their own. And so I was thinking about, like, is it community by community? Is it cultural? Is her community exception? Is my community exception? Am I just jaded because I raised kids in New York City for so long who were riding the subway in seventh or eighth grade on their own? And so it's hard to generalize, although certain people like to and like to put a lot of judgment on it. Do you want to talk about the free range debate, Cara?

[B]

Yeah. So we'll talk about it in the context of walking. I promise we'll get to it in the context of. Of subway riding. Yeah, I. It's so funny. I thought it was older than this. I was looking around online, and it started with a woman named Lenore Skanazi who was at the epicenter of a media storm when she let her child ride the subway alone. And I think it was around 2008, 2009, when this first started. Although she wrote a book called Free Range Kids that didn't come out until 2021, I thought it was a. Before that. Maybe that's the second edition.

[A]

I know of her in the context of the anxious generation and Jonathan Heights call for children being more independent. So.

[B]

So I remember meeting her when I was first on the writing circuit, and she was on every media outlet because she let her very young child ride the subway. And she was kind of skewered for it in the name of stranger danger and all the things that could go wrong. And she pushed back hard and basically said, how am I going to raise an independent kid if I don't give my kid independence? And I think what was most striking to me about the whole thing was the recognition that people are very dug in on one side of this or the other. What you're seeing in your neighborhood, Vanessa, is like the sweet icing on the top of a cake that is very, very opinionated. There are groups of parents who believe it is the absolute right thing to pick your kid up. It is the safest thing. And they cite all sorts of anecdotal stories or statistics or whatnot. And then there are a group of parents who think it is the absolute wrong thing. And how are your kids going to spread their wings and how are they going to learn? For the purposes of this conversation, I think we have to acknowledge that if a kid can't learn to walk on their own in a safe and responsible way from point A to point B, the other things we're going to talk about are really hard for them to do on their own. Like this. This feels very foundational. But what's the right age? What's the right developmental moment? I don't know that we can answer that. I think it really depends on a zillion circumstances. We'll be right back, but first, a word from our sponsors.

[A]

Cara At Great Wolf Lodge, there's adventure for the whole family. I'm excited to check out the lodge in the Poconos, which is close to me. And with 23 lodges across the country, there's probably one near all of you, too. You and your pack can splash away in the indoor water park where it's always a toasty 84 degrees. There's a wave pool, a lazy river, and a bunch of massive water slides, including ones your family can enjoy all together.

[B]

They even have adventure packed attractions from Magi Quest, a live action game that kids can play throughout the lodge, to the Northern Lights Arcade. And there's also a bunch of great dining options and complimentary daily events like nightly dance parties, all under one roof. So bring your pack together at a lodge near you. Learn [e-mail] that's G R E A T W O L F.com and strengthen the pack.

[A]

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[B]

You wore it every day.

[A]

I did.

[B]

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[A]

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[B]

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[A]

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[B]

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[A]

DSW. Let us surprise you. In New York City, the sort of communal choice when my kids were younger was fifth grade. So kids could, and it started out they would ride the school bus home and then they would walk from the school bus the sort of three or four blocks, you know. Cause the buses stop sort of every, this is not yet the public bus. This was the, you know, the school yellow, actual bus, yellow school bus. And they would get off at their stop and walk sort of three or four blocks. That was like the first training ground. And then in New York you were younger.

[B]

So like generationally. Right.

[A]

I mean, when I was growing up, we walked to school in groups starting at six maybe.

[B]

My, my husband and his siblings walked to school. When he was in kindergarten, they walked to school and, and he grew up in la and they walked from his childhood home onto Wilshire Boulevard. Anyone who has been in Los Angeles, you have probably driven on Wilshire Boulevard because it's one of the most trafficked thoroughfares in la. And then they crossed at an intersection of Wilshire and Santa Monica Boulevard. It is like what's the crossing in Tokyo that has 2,500 people per crossing? That's what it feels like there. And he was five and he and his siblings did it. So I think it's interesting to sort of, we've, we have moved the standard a bit generationally. Right?

[A]

Right. And there's, you know, there's the aton paths of it all, which was the disappearance of a child. And I guess it would have been in the early 80s, yes. And you know, that, that put the fear of God in parents. And then we grew up with milk cartons with photos of missing children on those milk cartons, which I think must have been a knock on effect of Aton Pats his disappearance. And so as we were growing up, a culture of fear did emerge. And I think parents became more also, you know, with the suburbanization and people living further and further apart, you know, you just like needed it was too far to walk.

[B]

And when kids were in public schools together versus when in some neighborhoods the communal public school ended up not being so communal. Like in la, a lot of the public schools are charter schools that draw from all over.

[A]

Right.

[B]

So even kids in public school don't live in the same neighborhood anymore, which is complicated. It's like all the layers, right?

[A]

All the layers, right. When I think about what was involved, the scale skills involved in teaching my kids how to walk on their own, it was, you know, the first thing is just like crossing the street. How do you cross the street? And again, getting back to the fear. There was a child hit and killed on my block when I was teaching my kids how to do it because a car was turning and he was. The child had the right of way. He was with his parent.

[B]

Yep. And exact same here. So we're two for two on that story, Vanessa, which tells you how common that story is.

[A]

It's terrifying. And so from that point on, and that was now many years ago, when I would cross the street with my children, every single time I would turn my body towards oncoming traffic and I would hold up a hand, I've seen that hand signal. You see me do it. When you do it for me, in

[B]

a way, you feel so good.

[A]

So, you know, it is scary having kids and you know, layer on top of that. And we're going to get to technology. If kids are walking looking down on their phones, it's absolutely terrifying. So training my kids how to cross the street, how to respectfully walk down the street. Right. You walk on the right side of the street. You're not, if you have a phone, you're not looking at your phone, your phone's put away. It just little stuff. How to pay attention to the people around you. Is anyone making you uncomfortable? Do you have any concerns? What do you do if something goes wrong? You know, don't jaywalk. Of course, then I was constantly jaywalking, so I was do as I say and not as I do. You know, all those little, little skills

[B]

for the anxious child, that skill building does Turn up the anxiety. And they often interpret the safety teaching, don't do this, don't do this as this thing will harm you. And there is a real balance for a lot of adults. How do I help my child who runs anxious manage this very important foundational skill? When we're scared of certain things and they are sort of disposed to see the world through that lens, it's it that is complicated if you are parenting an anxious kid. As hard as this is, it's a different kind of hard if your kid is wired to be worried about everything coming their way. But so there we are, we're walking alone and I think we've established it and said sort of beaten that dead horse about that. That's step one in terms of being able to venture out on your own is literally, can you get yourself somewhere walking? Then there's putting your kid in a car with another adult. So, I mean, we both live in areas where carpooling is central to life. We depend upon our village of co parents or did when our kids or younger to get our kids from place to place. And we got their kids from place to place. And that is its own layer of independence building because kids have to behave in certain ways in other people's car. Right. So there's the sort of how. How do you interact with other kids and the parent in that car? And then there's the fascinating side of how do you manage what you see and hear when you're in that car. Like, my kids would come home from carpool rides and start talking about what the conversations were or what the family dynamics were. And I mean, I don't think I ever anticipated that piece of it, but that's a very big piece. Everyone's different and everyone's dynamics are different. And certainly they're going to hear things that you were not anticipating they might hear.

[A]

Yeah, I mean, it's the ultimate like different families, different rules, different families, different attitudes, you know, all of that stuff. I mean, in our family, the story that never gets old is, so my sister was in a carpool with some other kids and my sister got dropped off and the carpool pulled out and one of our other now still lifelong dear friends fell out of the car.

[B]

Oh my God.

[A]

She was.

[B]

She was not funny.

[A]

She was like, her seatbelt wasn't on. I don't even know. I mean, this would have been 1979 or something. I don't even know if there were seat belts in the car. If there were. She wasn't wearing one. The car door was still open. The adult drove away and the kid fell out of the car. And then her mom was at work. Our friend ended up spending the day with my little brother, who was the only one at home. And like, nobody had could take her to the doctor. I don't know if there was like a baby back. I don't know. The car came back and like, was like, I gotta go drop off these other kids. I. I don't know. It's like the craziest story ever. And we laugh about it, but of course it's not funny. It's terrifying.

[B]

It's terrifying.

[A]

So, like, some parents are more casual. I'm like, really strict about people. Like, nobody's on their phones in my car, you get off your phone, I make sure everybody's seatbelt is on. And like, lo and behold, I also force them to be in conversation with me. I don't force them. I engage them in conversation. So there's fun stuff and nice stuff. And if also if you learn to keep your mouth shut, which I eventually did. You get to hear lots of interesting stuff when you're the driver of the carpool. But it's just another way in which our kids are navigating other people's lives and realities and figuring out their own behavior in response. And things don't always go so great. And that's also a thing to figure out. You know, how do they advocate for themselves? Did they tell you? Or did they sit in it silently and you find out from somebody else, like, all of those things are part of that process. And then you get to the list of things like sleepovers. And I. It's so funny, Car. Our sleepover episode is like one of our most controversial episodes. Who knew?

[B]

Because we said. Because we said that co ed sleepovers were not a big deal. That.

[A]

Well, I mean, in context. But there were people who were like, under no circumstances is my child allowed to go out to a sleepover because they have concerns about child sexual assault, they have concerns about firearms, they have concerns about substance use in the home. Like all super valid concerns. Yep. And we didn't address in detail some of those concerns. And people were upset about that.

[B]

Understand another one of those episodes on like the Sleepover Revisited.

[A]

Yeah. I mean, we did a newsletter on it to respond to a lot of the concerns because we were so shocked by people's.

[B]

We actually like five minutes into podcasting, I think maybe we had two subscribers.

[A]

I know, Seriously.

[B]

And both were offended in some way. Shape form.

[A]

Yeah. From one end to the other. So it's sleepovers, kids going to sports tournaments with other families, you know, sort of traveling. Summer camp is a really big one. Being on their own, are they ready for it? Can they handle it? Do they have the skills? Those are eggies.

[B]

And talk about scary stories. I mean, you know, last summer with camp, was it last summer with Camp mystic in Texas, where, you know, flash flooding and it was a total tragedy. Lives lost, kids swept away. And you send kids away to summer camp to build their independence, to build their resilience, to give them joy. And then there's always a story that just gut punches you. And you sit there as the parent and say, I don't know that I can do that. I'm having trouble weighing the pros against the cons, because I know the con is an extraordinarily rare circumstance, but it's out there. I saw the pictures, I read the headlines. You know, I've listened to the interviews and I can't get past it. And so it's this, to me, the sort of arc of sleepover and tournaments and camp, it moves us from a place of like tactical comfort or sort of getting over our tactical discomfort, I would say to sort of. It's a different kind of let go now. It's a let go for many days, sometimes many weeks. We adults have to get ourselves to a different place emotionally so that our kids have true emotional permission to go and learn the independence building skills that they get in these camps and circumstances. Right. Like, if we do not let them go, how can they actually individuate from us? How can they? And this is not to say I have a neighbor who I have known for 30 years. I love and adore her. She has three of the best kids, like, literally. I don't like to compare kids, but these are like the best kids. And she is a phenomenal parent who literally did not believe in sleepovers and was adamant, adamant that her kids not do summer camp and not do sleepovers. And she had very rational reasons and she had a lot of things that she built into their lives and that they eventually built into their own lives that made that rule work for them. So this is not to say, and by the way, they are three of the most independent, most resilient kids I've ever met. And I mean, spoiler alert, the last one broke her and she was like, fine, you can do the sleepovers in the summer camp because she realized they weren't as bad, they weren't the demons that she was making them in her head. But you don't have to do these things in order to gain independence. And some people don't have the resources to or don't have the circumstances, the flexibility. Maybe there is a sick adult who needs the attention or the help. Some kids. I have interviewed so many kids for college over the years and I. I've lost count of the number who were the primary drivers for an adult in their house, primary caretakers for an adult in their house. They worked a part time job after school and they worked all summer to contribute to the family. Bottom line, there are a lot of reasons why kids cannot indulge in this form of independence. But I would argue that even if your family is not doing a prolonged stay away, going through the exercise of letting go in that way and allowing them the space and grace to individuate more before they leave your home, it's a huge milestone and it changes who they are, changes the dynamic in the family. And I think in all good ways.

[A]

It's funny because my mom hated sleepaway camp. Hated it. She had a miserable. She was bullied. She hated it. Yeah. And she was able to recognize that in herself. And she said, you know, if my kids want to go, I will let them go. I will recognize how hard it is for me emotionally and. But if they want to do it, you know, I will, I will let them go. And I think to me that really self reflective choice that she made is about so much more in this journey, which is like knowing how hard it is for us. Whatever the independent route is, whatever the particular pathway is that you're contemplating.

[B]

Yeah.

[A]

You have to own your stuff and know that it cannot dictate what happens with your kids. Like as I mentioned earlier, some people have real traumas and painful memories and experiences having done this stuff. But there are certain things kids just have to learn how to do. And so I think finding another adult to talk to about it, your partner, your therapist, your friends, whoever it is, and parsing what is like a kind of rational reason not to let my kid do something. And what is something that I gotta kind of get over? I mean, a biggie for those of us who raise kids in New York City is public transportation. But you know, in all places there's, I mean, not in all places, obviously in more rural areas, but there's, you know, public buses, commuter trains, all sorts of things. And I have a friend who grew up in New York city in the 60s and he rode the crosstown bus by himself at 5 years old.

[B]

Oh my God.

[A]

And he was like, that's what we Did. I mean, can you imagine today if you saw a 5 year old boarding the M86 bus? You'd be like, no, where is this child's parent or babysitter?

[B]

But I'm going to draw a direct line. You're going to go, that line has to be erased. But I'm going to draw a direct line between that and the 9, 10, 11 year olds that I see on electric bikes. And they are driving down main drags and popping wheelies. Vanessa. Putting themselves into physical danger. I mean, riding at 30, 35 miles an hour, yet they're not five, but they're, they're not 16 and they're not 21 and they have no sense of. And that's a form at this point, that's a form of public transportation and a different set of decisions and conversations you got to have with a kid.

[A]

When my kids, instead of riding the subway, a bunch of kids rode scooters, not electric scooters, like pedal your foot scooters powered by humans, like 30 or 40 blocks to school. They did the couple miles on scooters instead of walking or riding the bus or riding the subway. And they were fast because a big part of the ride was downhill down, for those of you who live in New York City, down West End avenue from the 90s into the 60s. And most of the kids were not wearing helmets. And I knew that even if I told my kids to wear helmets, I just didn't trust that in a group of kids who weren't wearing helmets that my kids would always make the decision to wear a helmet because it's, because of them, it's the peer influence, it's developmentally appropriate. And I sort of took on board their developmental stage and the risks and my, and my worries about scooters and helmets and going fast, downhill. And I just said, I'm sorry, you can't ride a scooter to school. And you know, they had a, there was a little bit of pushback and I said, I'm happy to revisit it if you can affirm to me. And they kind of couldn't commit to it because they knew nobody else was wearing a helmet and they knew how hard it would be to stick to that if they were the only one. And so I think that gets at another sort of core issue, which is if there's one way to do something safely and there's another way to do it not safely and you don't have trust, faith, belief, or you're put it a nice way, your understanding of child Development allows you to recognize how unlikely it is that they're going to do it the safe way. Yep. What do you do? Should I have let my kids do it and wait till they get caught not wearing their helmet? Am I sort of undermining their independence by sort of not giving them a shot and seeing what happens?

[B]

Right. I mean, said another way, do you send them to Coachella? Right. I mean, it's all the same decision tree. It's like Vanessa's not speaking because she's still laughing.

[A]

Because I'm still laughing because I'm pick. I'm like, the line between little scooters and Coachella is a. It's a fair line.

[B]

It's fair.

[A]

I'm with you on that line.

[B]

It's fair. I mean, it used to be, do you let them go to spring break on South Padre Island? But now the 2020s version is, do they go to Coachella? And I think this is all part of the gray zone. You know, we started by saying there's a right answer. The right answer is to build independence. Here's the gray zone. The gray zone is how for any. Right, for any given one of these things, like, I don't know. I don't know if my kid is ready. I don't know if my kid is going to be able to say no to the. Whatever it is, it could be an electric scooter and it could be drugs. I don't know. But whatever thing is being presented to them by someone who they love and adore or someone who's super cool or someone who's really charismatic. I don't know. And so where does independence building fit into all that? That's messy. That's great. Right.

[A]

And how do they ever build the muscle of making the right choice if they're not presented with the challenge or the choice in the first place?

[B]

Right. And the answer that you and I come up with like always, and they hate this answer, but it's true, Is the constant conversation involving role plays helping them to flex the muscle so that they are prepared for the situation. But at a certain point, Vanessa, I think it's up to the parent or trusted adult to gauge the kid and the situation and go, I think my kid can make the smart choice or I don't think my kid can make. I mean, you have four very different kids. One of your kids, I can say for sure, could have gone out with that scooter group and would have been 100% fine. Right. Just because the desire to be, like, flying down a Road at speed with no helmet on. That just doesn't fit their personality.

[A]

Right. And I sort of wonder a little bit if my kids were relieved that I said no, because 100. It was scary to them and they wanted to do it because everyone was doing it, but they were also scared and weren't ready for it. Now, you could argue that riding the New York City subway instead of scootering is equally dangerous in its own ways, and you would have a fair point. And we can, you know, and if

[B]

you acknowledge that it's scary for them, are we doing them a disservice by not pushing them a little bit at a certain point? Again, to the anxious kid. Right. If we acknowledge and honor the things that they are a little bit afraid of, then at what point do we have to help them get over those things they're afraid of in order to get through life?

[A]

Right. And sometimes we need them to be independent because we can't be there. We can't take them. Like in the case of my kids, I couldn't take them to school. They had aged out of the bus. I couldn't take them myself. They had younger siblings who I needed to get to other places at the same time. And so they had to just like, bite the bullet and do it. And, you know, this is where kind of doing it in groups or doing it with friends and practicing it, I mean, there is baby stepping into this stuff. There are times when, you know, the first time my kid flew on his own, he. He had to do it because my passport was expired and I didn't know, and he had to get on an international flight by himself so I could go renew my passport and get on a flight the next day. So, you know, and in this case, I was waiting with him at the gate and my. My husband was meeting him at the other end, so he didn't go through everything, but he did take a plane ride on his own. So sometimes it's out of necessity that we do.

[B]

The first time my daughter flew alone, I just have to say, yeah, the guy sitting, she was with a group of friends and they were going to camp. Like, this is a full circle moment in this podcast. They were all going to camp. They were flying, and the kids were sort of scattered through the back three rows of the plane as by the bathroom, and there was a guy sitting next to her, and she and her friend were leaning over row to row and talking to each other. And, I mean, I have to imagine that it wasn't terribly disruptive, but it was clearly annoying. And at one point he turned to them and said, if you don't quiet down, I am going to throw you out the window.

[A]

Oh my God.

[B]

And they were young enough that they thought, this is a real possibility. I could be thrown out the window and game over. And she really like that story, totally shaped the way travel worked for her for years. I mean, until she put two and two together and thought, oh, you can't open a window on a plane. Right.

[A]

So oh my God. Right. I mean, that's the thing. You can't control how other adults speak to your kids, how they or how your kids behave. Yeah, any of that. So talking through it and having conversations and scenario planning is really, really important, even if your kid is not interested in having the conversation.

[B]

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side to to every story.

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Get the money side of the story. Subscribe [e-mail]. And one thing I do want to circle back to. You made a little comment about tech and I want to talk about it for a second because you know the story about being disruptive and other people perceiving you as rude or annoying and trying to shut it down is one scenario you want to avoid. The other scenario I always wanted to avoid was have my kids be so entrenched in their tech that they were clueless about the World around them. That is a serious safety hazard. Crossing the street while on a phone. Serious safety hazard. I was in New York not long ago and I am going to award New York worst city in America in terms of the eye contact on a sidewalk. Everyone was on a phone, everyone was looking down. People were walking like within inches of each other. Then they'd look up and they wouldn't even say sorry. They wouldn't even put their device away. And then it was head back down and that was just sort of congested and, and it made the sidewalk unpleasant. But then there's danger. So, I mean, on the tech note, I think there are some real concerns. And this is not about little kids. This is about everyone.

[A]

Right. I mean, there is the big debate. If my kid is moving around on their own, do they need a phone? And I gave my kids phones when they started moving around New York on their own. Not the few blocks from the bus, but like by sixth grade, my kids had phones, they were moving around on their own.

[B]

They were like in another state playing soccer or whatever it was. That's true.

[A]

Yeah. And you know, they were riding buses, minimally supervised buses to a whole other part of New York. And they were getting off those buses in the dark, late at night, waiting for an adult to pick them up.

[B]

I mean, but there are some parents who might make the opposite decision. And I, that's fine. I mean, whatever works for you.

[A]

People would say, yep, no, they're fine. I was fine when I did it and they're fine when they did it. And yep. I think it's less about what is the right decision and having a thought process and a reason why you've made the choice. And the reason is not all my friends have phones or I need a phone, mom or dad, it's here are my thoughts about safety and well being. I'm going to make this choice. And by safety and well being, I don't just mean safety on the street, but safety and well being in terms of their mental health, in terms of their, you know, access to tech. I mean, everybody's going to make a different decision. You just go through the process yourself and you're still the adult. You still get to decide what makes sense. I mean, some families give their kids a phone and when they get in the house, the phone gets turned in, or it's not a smartphone, it's like a flip phone and they just use it for texting. I mean, there's all sorts of permutations. This is where the sort of landline, the reemergence of the landline doesn't help as much because if kids are moving around on their own, they don't have, you know, a landline isn't helpful. It's helpful in kids socialization. So. So in this case, you know, Jonathan Height comes down very strongly on this. They don't need a phone to move around on their own. You know, everyone's going to have their own perspective on it. I think to your point about Kim's anxiety, like what will help them feel more confident and capable of doing this? Does having tech help or not? Is a phone worse or better than an Apple Watch? You know, all of these things are every family is going to do or

[B]

worse or better than a buddy. Like there are lots of ways to go, right? There are lots of ways to go. I think where we should land is sort of just a small reframe on where we started, which is okay, they have to become independent. Right. So in service of becoming independent, what are the capabilities that they need to acquire over this decade? Right. And I mean, there are a handful of them. We've talked about personal safety, right. Everything from awareness of your environment to understanding the decisions to make on your own when you're in that environment. They have to be able to communicate. They have to be able to tell their parent or their trusted adult when things went wrong so that they can learn from that and try again differently the next time. They have to be able to celebrate what went. Right. It's amazing to accomplish navigating an airport for the first time on your own, that is like, it is a huge moment for kids. And then they need, they need the ability to make decisions that are smart. And you and I talk endlessly about decision making, but they need to be able to learn how to resist peer pressure around decision making and make smart decisions. They need to listen to their intuition and make snap decisions. Right. So these are all the sort of ingredients that go into the decisions that you will make about the kids in your life. And one, I think one of the most interesting places that I landed with my kids and I think you landed with yours, is the kids are raised in the same house. My decisions for my different kids were different. Their ability to assess safety, to communicate and to make decisions was different. Right. And so what I was comfortable with changed as I was sort of doing it in the context of each kid.

[A]

Yeah. And I think that ties to the question of whether you track your kids or not. So my kids all are on one of these platforms. I never track them secretly like it's not covert, but I really try not to use it because I'm really trying to build their skill of communicating with me and me communicating with them. And the very few occasions I use it is when I cannot get a hold of them. To your point of different kids, some of my kids are better communicators than other ones. The other situation I use tracking is if I know one of my kids is driving, I don't want to call them while they're driving. I certainly don't want to text them while they're driving. But, but I, I want to know, you know, where they are. It's a safety issue. But also it may be like, you know, are we going to eat dinner anytime in the next four hours or not? And so I will quickly just find out where they are and track them because it's better to do that than it is to call them while they're driving and have them talking to me on the phone while they're driving, which I don't want them to do. And so the whole thing about tracking is similar to the, the other aspects of tech, which is like everyone's going to do it differently. It's super important that kids know they're being tracked. It should not be a covert operation because that destroys trust and trust is at the foundation of all of these independence building skills. But secondly, kids have to learn how to communicate. Communication is the key to relationships. And so if they know you're tracking them, then they're disincentivized to actually be in touch with you.

[B]

That's right. I mean they, they see it as a passive form of communication. What do you mean I need to communicate with you? I'm already communicating with you. You know where I am.

[A]

Right.

[B]

And what you want to teach them is the skill of actually sharing with you when necessary, where they are. And then as they get older, learning when you don't need to know where they are, which is a whole different skill set that we as adults need to work on when, when it is time for them to move out and be on their own. We need to respect their privacy.

[A]

Yeah, Y. Yeah. I mean that's a whole other episode. Car.

[B]

We will do that.

[A]

We will do that. So would love to hear people's thoughts, reactions, scenarios. We didn't get to. I mean, I think driving is a whole big topic. It's its own episode. Another place I was subpar as a

[B]

parent, but yeah, self driving cars all over la. I have to say from the are they ready for this safety independence angle? They are a nice deep exhale. They are. You can sit in the back of that self driving car and be on that phone or do whatever and it's not an issue because you're not driving it.

[A]

So we can talk about that. I mean that's a whole other thing. I can't get my head around it,

[B]

but oh it's awesome. Next time you come to la, Vanessa, we're going to drive around in those.

[A]

Oh God, I don't think I can work. We'll work on it. We'll work on it. So send us your reactions, thoughts, questions. I'd love to hear what challenges you're facing and you know, how you solved it. Or maybe you haven't yet. Anyways, thanks Cara.

[B]

Bye Vanessa.

[A]

Thank you so much for listening. You can email us with questions, feedback or Episode [e-mail] if you want to

[B]

learn more about what we do to make this whole stage of life less awkward. Awkward for everyone involved. Our parent membership, our school health ed curriculum, our keynote talks and more are

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