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Episode 174

The Power of Parent-Child Trips: Connection, Confidence & Memories That Last

August 25, 2025

What if one trip could change the way your child sees themselves—and you?

 

In this episode of The Art of Raising Humans, Kyle and Sara Wester reveal how one-on-one trips with your kids can become powerful rites of passage. These aren’t just vacations; they’re intentional experiences designed to build skills, deepen connection, and show your kids you believe in them.

 

You’ll hear how Kyle and Sara structure these trips by balancing fun, tradition, and meaningful conversations so kids practice independence, decision-making, and resilience, while also creating unforgettable memories.

 

If you’re ready to move beyond “just a trip” and create transformational experiences with your kids, this episode will inspire you and give you a practical roadmap to get started.

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Episode 174 Transcript:

I think every parent listening to this podcast would love to have a deeply connected relationship with their kid throughout the entirety of their lives. But you know what? That does not happen by chance. ⁓ That happens by intentionally ⁓ finding ways ⁓ to create like milestones and opportunities ⁓ for us to see the relationship in a different way and also invite our kids into a different type of relationship. Cause we can't continue to relate to them.
like their little three or four year old kids throughout their whole life. And I know some parents do that and it causes a lot of conflict and tension because the kids don't feel like the relationship is evolving in the way it needs to. And so when Sarah and I talk about the ways we do that, the way we share those ⁓ specific steps that we take to help invite our kids into a different relationship.
Parents have said, you need to do a podcast on that. You need to share the things you guys do, because it sounds so fun and it is really, really fun. And so today, Sarah and I want to dive into how we intentionally use travel and other types of fun activities to help our kids be invited into a different way of relating. It also helps us see them in a more independent way. It also helps them ⁓ feel more confident and be less anxious.

Kyle And Sara Wester (29:19.328)
about the life they're about to go into as adults. think all of us want that. We want our kids to go into adulthood feeling capable and confident that they can succeed. And we need to feel that too. So I think you'll really enjoy today's episode and hopefully it help ⁓ start to increase your imagination of what those years could look like as they move from the elementary age into the teen years ⁓ and on into adulthood. So if you haven't already, please take a moment to stop ⁓ and take a moment to rate, review and comment.
about the podcast. It's so important for us and how we grow and reach more people. And we're getting to reach hundreds and hundreds of people, ⁓ thousands of people sometimes each week. And it's just great to be able to reach more families, give them this information. And we want to just be able to give it away for free ⁓ through this podcast format. So you commenting and subscribing and sharing and rating, all that stuff really helps ⁓ the podcast grow and reach more families. So ⁓ sit back. I hope you enjoy the podcast today.

Kyle And Sara Wester (0:1.614)
Hello and welcome to the Art of Raising Humans. I'm Kyle. Hi there, I'm Sarah. ⁓ And today we wanted to discuss something that many people have talked to us about discussing. ⁓ We'll chat about these things that we do with the kids and many people have said you should do a podcast on that. Yeah. Right? Yeah, just in casual conversation we'll mention something and yeah, so then we thought okay, well, all right, we'll do that. Yeah, like we're always- it a try. Cause we're always trying to take the podcasts and-
⁓ Get different topics. Some are ones that are pain points for parents, but other ones are about ways to intentionally evolve the relationship with your kids ⁓ and and that I think is a big part of intentionally parenting as your kid is going from you know, the elementary kind of school age moving into the the preteen age into the teenage years ⁓ is We want to really be thoughtful about how we do
that change because eventually they're gonna be adults. ⁓ And if we haven't thought about this and so many people who come to us for help, they're in those different stages. They're moving from like, ⁓ kids moving from fifth grade to sixth grade, ⁓ that's kind of a big shift, but then also into high school. And then now their kids go into college and each of those times has a different kind of morphing or evolution of the relationship. Yeah, and I think, ⁓ you know, we were talking to another parent the other day and just that whole.
You know, you have the baby, the toddler, you're thinking ahead. You know, you're always thinking ahead. And then you have the elementary school and then middle school and high school. And now that we've been doing this a while and we have, you know, kind of moved through those stages, we were talking with this other parent who'd also been doing this for a while. You know, it's like we, you reflect back and you think, okay, what was helpful or what are some things that I've heard or that we do that ⁓ I love to hear those things from other parents. So this is kind of one of those podcasts about like,
Here's something we've done, we know other people who do, and it's just been really great. Let's share it. So on this podcast, we want to share some specific things we do that ⁓ could be seen as like rites of passage with the kids, but also even core memories that we're making with the kids. ⁓ But we want to frame it into why we do it with our kids, right? That ⁓ there are skills in particular that we're wanting our kids to learn that they're going to need.

Kyle And Sara Wester (2:23.234)
going into the teenage years and then into adulthood. But like I said, there is also, ⁓ we've used this term before on the podcast, ⁓ that relationships are like a dance. And there is a change that begins to happen from us leading the dance steps. Our kids saying, what's the dance we're doing? Not literally, but kind of figuratively. And what's the dance we're doing? They're kind of letting us lead because they don't know how to, to eventually you want your kid to be able to lead ⁓ and for us to do that together.
And that's kind of ⁓ what we notice sometimes missing as we became adults with our parents, but also ⁓ what we see other friends of ours who are adults, you know, is it's hard to, ⁓ that transition of going into you on your own, being an independent adult, that many times our own parents hadn't been intentional about what that's gonna look like. I know for me in my 20s, there's times where my parents were still parenting me like a child and it wasn't until... ⁓
you know, we had some intentional conversations about how that changed, you know, but we wanted to help our kids ⁓ move into that independent stage and eventually into interdependency with us. ⁓ And we found these specific kind of fun activities helped us do that. Yeah, yeah. And with a really big emphasis on the, of wanting to stay connected, ⁓ you know, from day one to all the way to their adulthood, we just really, you know, you said that interdependence.
Connection is a really big focus of ours. ⁓ And ⁓ we'll get into this, but even just resiliency, there's so many things that this one activity just really does a great little capsule of all these things. Yeah, so we've talked about before how we love travel, so travel's a part of it, right? And something that we started intentionally doing ⁓ when the kids were little is we started making sure that we may travel just kind of a part of our lives, you know?
And the reason why travel is so important to us is just new experiences, new places, new people to meet, but also having places that we could go back to on a regular basis that kind of remind us who we are as a family, you know, ⁓ making those memories. And so that's kind of a small part of this journey is just doing that because I think- This is something that we love, we value. You know, you have those things in your life you want to pass them on to your kids. Travel is one of those things that we both love and-

Kyle And Sara Wester (4:42.894)
⁓ And whenever we talk about travel, we're not even talking about going to big places we're talking about ⁓ I think when they were little Sarah was just having I think every listener has these things it was ⁓ the local science museum or it was the you there were these regular things Yeah, the going to the zoo or going these kind of little excursions you would do that were almost like day trips or fun adventures, right? Because they were little and it was hard to travel long places, but then we began to kind of map out
other places one could then maybe were a little further away and kind of make those memories. But all of that then morphed into this idea of as we as Sarah and I began to think, how do we start to hand this baton off? How do we start showing the kids that there is a change on the horizon? Meaning we have been managers of your life. We've been kind of directors of your life and little kids in elementary school, they want you to, know, they want you to kind of direct ⁓
obviously a baby definitely does. Yeah. But I'm saying even those elementary years, they want you to because they're like, yeah, because you can make these big decisions. I don't want to make them just tell me where we're going, what we're doing, you know? ⁓ And as they start to grow up into the middle school type phase area, especially for us, we're kind of hitting that more that 13 year old time ⁓ is we wanted to be intentional about saying, let's start ⁓ making this emphasis on giving them specific skills.
that will help us ⁓ create a relationship that is more connected ⁓ and it starts to kind of change those dynamics. So ⁓ what we did was we were very intentional ⁓ and you can do this however you want to do. You don't need to do it specifically how we're doing it. This is just how we found out ⁓ has been very successful for us. So as our oldest turned 13, ⁓ there was a discussion about where ⁓ she would like to go. And what we wanted to do was do a trip specifically that was you and me together with her.
And why was that important, Sarah? Why was important for us to do that together with her? Well, we wanted that, you know, when all the kids are together, for us, we have three. So we wanted that focused time. ⁓ And we wanted to, it's going to happen anyway. You know, your kids naturally have this, you you call it individuate or ⁓ they're driven. Their brain is driven to go, can I make it? Who am I? How am I going to do this ⁓ life thing?

Kyle And Sara Wester (7:5.832)
And so 13 is kind of that ball is rolling. And so we wanted to jump in with her and say, we see that ball is rolling. We're on board for this. Let's start. ⁓ It's like highlighting something that's already going on, but paying honor to it and noticing it. So then it's on the table to talk about more. Yeah. Well, and developmentally, we know kids at that age ⁓ are seeking identity. Who am I? Can I do this life? Do I have what it takes to be successful?
⁓ And so for us a tool of that, just to say is like, where would you go? And we both wanted to be on that ride with her to like, hey, we're here with you. ⁓ We love you, we believe in you. And so part of that, just who are you is where would you go? What would you choose to do? Where would you like to go with us? And we did so many ways, but we thought this is a way for her to think about who am I, what do I love, where do I want to go?
Well, in that also what we did is we had a budget, so we gave her a specific budget. ⁓ There's a great app that we've used called Wanderlog.
and she was able then to use that, put that money in there as a ⁓ budget for the trip. And then we talked about how much the flights were gonna cost or if we're gonna drive there or if we did drive there, maybe we'd have more money. at first she wanted to go to New York and then it was like, wow, that's gonna be really expensive. ⁓ so, yes, as we did, it was kind of too much. So then we decided to go to the ocean because we live in Oklahoma and we're not necessarily near an ocean, ⁓ but she wanted to see that. So we had a couple different places to pick from. She picked that place.
And she planned the whole trip. Now, obviously she asked for advice from us or thoughts that we had, but it was really cool to watch her just embrace planning this whole thing. And I actually didn't know very much at all what we were gonna do. I mean, she planned the excursions, you eat gluten-free, Sarah, and she was very thoughtful about trying to find restaurants each day that were gluten-free so we could all eat there. Yeah, yeah, we kind of just handed it off to her. And so I was her buddy on that.

Kyle And Sara Wester (9:5.642)
on this particular app, can invite people to join you. So I would kind of see the process, but I was just there as more of a consultant. It was really her thinking about each day, what to do, ⁓ what were her interests, what she wanna show us and do with us. So it was really, really fun to see her.
think through all of that and ⁓ need to plan it. And she planned to go, okay, that's outside of budget or, I can do this or this, ⁓ you know, and thinking about locations. There's so much logistics to planning a trip. So it was really fun to watch that. I mean, on practical sense, just that skill build, because that can translate to planning so many things in life. us, we're using the trip to build some of those skills, but you could use it in lots of different ways, any kind of project or anything, but.
But it was neat to see those things build inside of her, for her to be thinking about herself, but thinking about these people with her. Yeah, she's thinking about what she wants to do, what she wants to do with us, what she thinks is exciting. I that was so fun to see that. And then, and then because the place we picked, we could drive to, that also helps save on the budget. So she was able to do other more fun things that she wanted to do. And then on the drive, you know, Sarah, what we intentionally did.
that I thought was really fun, we put her in charge of the playlist, you know? So she was able to pick the music. So the whole way down and the whole way back home was all music that she wanted us to listen. And of course, that involved a lot of Taylor Swift for her, but it was lots of fun to be able to listen to these, talk about the songs, talk about the lyrics, you know? ⁓ And it was, know, on that trip, there was ⁓ so many beautiful things that we were getting to practice with her. So ⁓ one is a word we use a lot, co-creating.
You know, like we're literally co-creating the trip with her. She's feeling the ability and gaining the confidence on how to have a budget, how to pick things she wants to, know, ⁓ restaurants she wants to go to. ⁓ She's getting to lead us ⁓ and we're learning to follow. And that's really, really, really powerful to send that message to your child that, you know, I've been the leader, but there's times you're going to lead and I believe in you.

Kyle And Sara Wester (11:11.286)
and I am willing to follow you as the leader. That's really powerful. And so I just want to bring extra attention well, and many times, Sarah, I think kids only get that experience if we're not intentional about it, doing it with their peers, you know? And we really wanted to be a part of that first big time that she got to do that, you know? To kind of be there, to kind of guide that, to see it, to encourage it, ⁓ to applaud it if she needed advice or wisdom. ⁓ And the picture I came up with and we kind of explained to her was, you you're about to go into this stage in life.
where we are not gonna be the drivers of the vehicle, ⁓ literally and figuratively, ⁓ and we just want you to invite us into the vehicle. ⁓ You don't need to drive around, and independence doesn't need to be you just being on your own, and we're like, what's happening? Instead, we'd love to be in the vehicle, ⁓ in a sense of in your life to where wherever you're going, we are on that journey with you. And it may not always be physically with you. mean, you may be off.
Obviously doing your own thing. She's gonna do that But we want to always be part of that process the decision-making the the way you're thinking about it Just let us join in on that and I think it's a really it was a really cool thing to watch her do that and to see how that that was several years ago we did this trip but to see how that has morphed into you know watching her become more independent and then also Continue to invite us into that through her teenage years. I think that's what every listener wants you want your kid
from those early years where they are so connected to you, we all naturally want our kids to be independent of us and to be able to find themselves separate from us. That's very healthy. ⁓ But I find so many teenagers think that has to be done on their own in isolation. And it's not because the parents want them to, but just because many times the parents haven't intentionally done anything that kind of gives the kid a vision, a picture of what that could look like for you to now guide your own life, but have us on board with it.
And there's just something to ⁓ being so obvious about it. You know, we intentionally had these conversations. don't just, it was something instead of it just happening, we're like, okay, these are the teen years. This is what's going to happen. This is how, you know, this is the trajectory of things. We want to be there with you in this process. So we laid those things out there and have these conversations. ⁓ Now we can revisit them time and time again. And I think it's just, you know, shining a light on it for her even to think, okay.

Kyle And Sara Wester (13:36.910)
owning this yeah here's my life my choices matter I can direct this thing I'm capable there's you know all these little messages that we're sending when we when we intentionally do that and so it's just sort of a it was a fun way to do that yeah was a fun way to have that adventure with her and convey those things and then and then we also do two other trips okay so so that that that's at 13 years old
We wanna do that with each of our kids, have this moment, you and I together, Sarah, planning this trip with them, and they're kind of bringing us on board. And we kind of explained all those different types of things. They're learning so many different types of skills and getting their confidence on kind of creating the life they wanna live. ⁓ But then the other trips we do is we really want it to be one-on-one with them and do some fun trips. So those can look a lot of different ways. It could look like ⁓ what I did with her.
when she was 15 is we took a trip that was kind of a surprise trip. I thought, you know, this will be fun. I know things that Abby likes to do. I know things I like to do. Um, and I know how they connect together in certain ways. So I'm going to kind of take her somewhere that she didn't plan that she didn't expect, you know, and she, she, she loved it. I asked her, said, do you want to be a part of this? You want me just to surprise you? She wanted to be surprised. So, and that day that this one did involve flying and thank goodness we
had some fantastic airline miles from Southwest. So once again, it made it very affordable. I don't think I even had to pay for the flight, but, then we're learning all the tips and tricks. Yes, because, because we want to do these trips and we don't want to be hindered by the lack of finances to do it. So I to encourage you. I mean, this was just through getting a Southwest card and getting a free getting points and companion pass and companion pass was great. And so I ended up surprising her and taking her to Salt Lake city.
because I had never been snowmobiling or done any these kind of like snow things. We're not skiers, but we wanted to do some fun things in the snow in a city we've never been to before and we love the mountains. And so it was really fun to surprise her that day as we drove to the airport to tell her where we were going. And that was really exciting for her to experience that, you know? And then on that trip, I was very intentional of making these core memories, you know, these memories of us doing something that we share together, which is this

Kyle And Sara Wester (15:57.216)
sense of adventure, trying something new, all that stuff, but then some really intentional conversations. I told Sarah beforehand, there's certain things I want to talk to her about or just be curious about what her thoughts are on certain subjects. ⁓ And those conversations were so fun, you know? And they're typically happening not during the events, but just sitting at a coffee shop or just like sitting over breakfast and just, she was just like an open book because
She was feeling very connected. ⁓ And I just want to highlight, you didn't go with your list of lectures that you wanted to have with her. These really were times of curiosity and getting to know her thoughts now. Because man, I remember that feeling of when they hit those teenage years, they're thinking about things shift and you just feel it. You just see them show up differently than how they used to. And so you went into that.
with curiosity about how are you showing up? What are your beliefs? What are you thinking about things? And then that curiosity opens the door for you to have some thoughts, but your intention wasn't here's the 10 things I'm gonna teach you and lecture you think we just need to be careful. Well, Sarah, I'm glad you point that out. It wasn't things that I want her to know. It's things I was just curious about how she thought about it. It really was seeking to understand her on all types of topics when it comes to school, her future.
Dating all those kind of things and a lot of that happened on just driving to and from events or like I said sitting at a restaurant Or being in the hotel at night before we went to bed And it was really cool to just see how open and receptive she was to it. She wanted to be known She wanted to discuss these things and it's just another aspect of hey, I want to be in the car with you I want to be able to be part of this journey that of you as you create the life you want and I want you to know I'm interested. I'm all in
I want to be a part of that. And ⁓ you were safe. Yes. You were a safe person who was listening and ⁓ not full of the judgment. know, like sometimes that anxiety comes in as a parent and you're like, I gotta say something about this. But you, you were just there for not, that was not your purpose. That's good. No, was to just listen and shut up. Yeah. So I had some key ⁓ questions I want to ask and I ran them by YouTube and just to kind of what I'm gonna kind of hit these topics. What do you think? And as I just asked, I just tried to do my best to shut up and just listen, you know?

Kyle And Sara Wester (18:18.104)
Okay. And then now you're about to take her on a trip. Yeah. Yeah. So, the night and this is no particular order for us. This is we wanted to do, we did want to kick it off together, ⁓ you know, like here we are. And then, and then do that special kind of, you know, you each have a different kind of relationship ⁓ with your child. And so it's that chance to highlight that and to bond and do things together in your style. ⁓ so
She and I, she has been wanting to go to New York. And so it has taken us a while to figure out how to do that within a budget for us. much cheaper if just you two go. is much if we go. If all three of us go or even the whole family goes. Well, we even looked, I looked at, you know, what time of year it's cheaper to go. Again, the airline miles, saving those up, that kind of stuff, hotel, all that. So we've been able to work it out. It took a couple of years, but we've been able to work it out. And now she and I are going on the trip.
and we'll be going to New York. And similar to what you said, you know, I have some things in my mind that ⁓ I hope to talk with her about. The focus of my trip though is just seeing her, ⁓ listening to her, having adventure with her. ⁓ Those again, you ⁓ hear this all the time now, but core memories. ⁓ That's the goal. That's my primary focus on the trip. So this one.
we plan together. ⁓ have I've taken the lead on where she she threw in all her stuff and got all excited and did all this planning and I'm just finalizing things. ⁓ think part of that to New York's a little complicated. ⁓ So so I definitely feel like okay, I gotta make sure we're gonna this is all gonna work out, you know, ⁓ so ⁓ I've probably I've stepped in a little bit more but I haven't entirely planned it. Yeah, it has been something we've done together. Yeah, yeah.
And so now you're going to do that. And that will kind of wrap up those three trips that we really wanted to be intentional about doing. And each one of them has a different type of emphasis. So ⁓ just to kind of recap, we've got the one we do together where that's kind of to kick it off. This is a new phase in your life. We want to celebrate it. We want to be a part of it. We're going to move now from being the director of your life, the manager of your life to instead, we're kind of moving into like a consultant phase, know, more of a consultant. We just want to be

Kyle And Sara Wester (20:35.110)
Invited in on that journey right to have our voice matter because we do think you have the parents voice does matter and the kid ⁓ Wants to hear they want to know what you have to say, but it's just gonna look different ⁓ Little hint of audience. Yeah, I want to be in the audience. I want to watch your life Yeah, you know, I hope you will run over and talk to the sidelines. ⁓ Yeah These kids are so anxious about
going into adulthood, we went, hey, we're cheering you on. We think you're gonna succeed. This is gonna be great. We're not going into this with fear. So that first one was a lot of co-creating together. It was sitting back and just like letting her take the lead. But then these other ones were more about us together with her, you know, as individuals with her, us getting to know her in a different way, her getting to know us in a different way by just sharing that adventure together. ⁓ then now our son has turned 13 and now we're planning the trip with him. So we're about to, you and I are gonna go to Chicago with him.
That's the place he chose and we're having so much fun planning that trip too. But it's really cool as we started this Sarah and I know we kind of cherry-picked this from a lot of different books or other you know people that we know who are version of mashing it. Yeah, but it has been so fun getting to have this intentional focus ⁓ on how to help our kids join with us on this like ⁓ as they're learning who they are.
How'd they want to show up in this world? And I just think it's a really fun way to do it. And every time we've mentioned it to people, even when we were in Florida ⁓ at the ocean with Abby, I remember we talked to some people on a boat that we were on and they were like, this is so great. I want to do that with my kids, right? And so it's just something that a lot of people have not thought about. ⁓ Maybe you as listeners have heard about it, but Sarah and I wanted to share today just to get kind of the wheels turning. Maybe your kid is really young and you're thinking, that's far away. ⁓ Yeah, but the thoughts can start happening today.
What's my plan on how to transition that relationship from being the manager of my kid's life to those teenage years? Because really those teenage years can be awesome. And lots of the conflict ends up happening because the parent doesn't have a vision of what that new dance looks like with the kid. It's just we continue to relate to them in the same way we did when they were little babies. And it's not working. And the kids will be very frustrated with that. Well, and I think by doing it so intentionally,

Kyle And Sara Wester (22:52.660)
It helps us remember to do that. yeah. yeah. I'm not directing anymore. yeah. I need to step back from that. So it's just a nice way to have that reminder. And we're using travel. You could definitely do something else. But ⁓ I wanted to lay it out because even if I've heard people, I did a trip with my team. You know, I just thought, maybe the details and ⁓ the motive and the motivation, you know, how we're going through it would be helpful to other people. You know, as we've dug through it, we've thought long and hard about this. We're like, let's share it.
Yeah, and I think we still might add on if the finances can be done before they leave the house at 18, try to do a big family. Yeah, whole big family one. And I know we've heard a lot of families who do that. Maybe you the listeners, you guys have done that. yeah, getting the whole family together and doing something that's out of the norm, you know, some some new place. It's like, oh, we're sending you off into adulthood. Let's go to this cool place to like celebrate that. So so I hope this really helps. Like I said, get the wheels turning.
help you start thinking and understanding ⁓ or start thinking about being intentional about how that change is gonna happen. Because like you were saying, Sarah, it helped get my mind, even with little things like having Abby do the playlist all the way down there. I typically liked ⁓ to put my playlist on. I typically am the one wanting everybody to listen to my music. And so to sit back and let go of that and then let her just control it, it was really cool. And then there was a lot of...
music I'd never heard of that I actually did really like and then now we have that connection through that too. And well, and it's really, why do you like this song? And just, just opportunity, not every single song, but you know, it's just another way to connect and learn a little bit more about your teenager. Yeah. Yeah. So I hope this helps give you a vision, a picture of how to use travel or other things like you're saying could be almost, ⁓ I think travel is a really good way to do it, but there's other ways I'm sure you could think of, and we would love to hear your stories. If you have ways.
that you intentionally do these kind of rites of passage or ways in which you invite your kids into independence and helping them co-create their future. We'd love to hear those stories and love to hear those ideas because we might integrate them into what we're doing with our kids as well. we definitely don't think we have it all figured out here, but we didn't want to just keep this to ourselves. And we kept getting feedback that people wanted to hear more of this. So thank you so much for taking time to listen. I hope this inspires you to plan some great trips with your kids and to start.

Kyle And Sara Wester (25:13.176)
Connecting with them in this more deeper intentional way. And so you hope you have a great day

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