DEEP DIVE: Tips for Vacationing with Extended Family

8 Jun 2026 · 40 min · 17 chapters

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In short

Vacationing with extended family (often 20+ people) and how to keep it functional and enjoyable with kids, differing parenting styles, schedules, safety rules, and shared logistics.

Guests

Margaret and Amy (hosts of What Fresh Hell? Laughing in the face of motherhood). They reference guest Danielle Bayard Jackson (discussed via a prior conversation about “Fighting for Our Friendships”) and multiple listener contributors (e.g., Katie, Caitlin, Emily, Anna, Laura, Ella, Stacey, Linietta Willis/Dr. Willis, Leslie).

Key claims

Plan ahead to prevent resentment; not every conflict needs to be said; avoid criticizing others’ parenting choices; have “same team” conversations with your parenting partner; use neutral systems (e.g., Google spreadsheets) so rules aren’t personal; hold lightly but enforce a few clear non-negotiables (e.g., nap schedules, safety).

Notable examples

“Life preserver” boundary on boats; plastic “water safety” bracelets to assign supervision; driveway car incident with unsupervised kids; dinner timing compromises (kids eat earlier, adults later); one big meal/day and opt-in hikes; shared grocery/expense spreadsheets to prevent “scorekeeping.”

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Reality of Family Vacations

1:02 to 2:30

Discussion about the challenges and joys of vacationing with extended family.

“And this week, we're talking about vacationing with extended family.”

Navigating Difficult Conversations

2:32 to 4:35

Exploring how to address uncomfortable topics with family before vacations.

“I mean, that's obvious when you think about it.”

Setting Boundaries with Family

4:37 to 7:28

Tips on establishing boundaries and discussing children's care during vacations.

“Amy, I need to talk to you about how insensitive you are about your behavior that is being seen on this vacation.”

Establishing Safety Protocols

7:29 to 9:25

Importance of safety measures during family vacations, especially around water.

“about which relatives on the trip can supervise the kids that you're bringing on the trip and which relatives are entertainment, but are not supervision.”

Balancing Competing Interests

9:26 to 11:16

Discussing how to manage differing needs and schedules during family vacations.

“So like, if I give you this bracelet, it means you're in charge of the kids.”

Navigating Vacation Dynamics

14:00 to 15:09

Learn how to manage varying interests and schedules during family vacations.

“a half hours during your baby's nap time.”

Navigating Vacation Dynamics

15:16 to 15:27

Learn how to manage varying interests and schedules during family vacations.

“That's Q-U-I-N-C-E.com slash fresh for free shipping and 365 day returns.”

Navigating Vacation Dynamics

16:42 to 17:05

Learn how to manage varying interests and schedules during family vacations.

“my prescription glasses, plus regular sunglasses over them, because otherwise I'll burn my retinas.”

Adjusting Expectations on Family Vacations

17:55 to 22:29

Understand the need for flexibility and compromise while vacationing with family.

“not going to operate the same way as things operate at home.”

Planning Group Meals and Responsibilities

22:29 to 25:18

Learn effective strategies for meal planning and sharing responsibilities among families.

“I see why that's frustrating to people as well.”
Show all 17 chapters

Managing Costs and Expectations

25:18 to 28:00

Explore strategies for handling expenses and family dynamics during vacations.

“vegetarian, you know, that stuff happens all the time.”

Navigating Family Dynamics on Vacation

28:00 to 31:00

Learn strategies for managing expectations and responsibilities during family vacations.

“groceries, meals, activities as we go along, and then they settle up at the end of vacation.”

Navigating Family Dynamics on Vacation

31:02 to 31:55

Learn strategies for managing expectations and responsibilities during family vacations.

“Oh, Amy, between swimming and sweating, summer is basically bad hair season at my house.”

Navigating Family Dynamics on Vacation

32:20 to 32:46

Learn strategies for managing expectations and responsibilities during family vacations.

“That's the energy State Farm brings to insurance.”

Humorous Realities of Family Vacations

32:47 to 36:19

Explore the funny and relatable scenarios often encountered during family vacations.

“Oh, look, somebody left dishes in the sink.”

Finding Balance and Setting Boundaries

36:20 to 42:00

Understand the importance of setting non-negotiables to ensure a pleasant vacation experience.

“It's going to be annoying to some degree.”

Navigating Extended Family Vacations

42:00 to 42:55

Learn strategies for managing family dynamics while vacationing with extended family.

“But if you have each other's backs, you'll at least be set up for some success.”
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Transcript

Automatic transcript. May contain errors.

0:01Mornings have a rhythm. You can hear it, feel it. And at Quaker, we fuel it. With 100 % whole grain oats and a good source of fiber in every bowl, helping you turn that rhythm into your soundtrack for a great day. Fuel to start whatever's next. Quaker, official sponsor of FIFA World Cup 26.

0:31your kids would be better behaved if they went to bed before midnight is not something you need to offer what fresh hell laughing in the face of motherhood or the grandchildren maybe get chicken nuggets at six and the adults eat at eight with margaret ables and amy wilson turkey lasagna is vegetarian a podcast that solves today's parenting dilemmas so you don't have to whenever there's conflict go back to more planning

1:01Hello, everyone, and welcome to What Fresh Hell? Laughing in the face of motherhood. This is Margaret. And this is Amy. And this week, we're talking about vacationing with extended family. If you must. Right. We always used to say that at the end of... It was like, what's that Chinese fortune cookie thing? It's a little body, so I won't say this. Yes, in bed. Yeah, and you say it at the end of every fortune, and it turns into a different fortune. Right, so put if you must at the end of every one of our... Titles. Titles. Episode titles. Vacationing with extended family. if you must, but you and I each do it every year, at least once.

1:34At least once. I do it twice a year, at least. I probably do it four times a year. Yeah. Because our vacations tend to be going to visit extended family because we live away from family. So our school breaks, we tend to go see them. Yeah, we do this every summer with my extended family, which is a large extended family, as I've talked about on this show, like we're up to like north of 25 people, which involves like multiple homes and lots of planning. And I really do look forward to it. But I've learned a few things. And our listeners have a few ideas, too. So we're going to talk about those. I'm for it.

2:04I think that vacationing with extended family writ large is a great opportunity to like express your values to your kids, which is we love our families. And we express that by staying close to them. And we get along with people even when it's difficult. There's plenty chock full of good lessons there. Sure. And I think it's actually generally pretty fun. So I did a fresh take a couple weeks ago with Danielle Bayard Jackson, and there was a book called Fighting for Our Friendships. And as I was getting ready for this episode, I thought back on a conversation we had that basically having the slightly uncomfortable conversation in the short term is way better than rankling resentments in the long term.

2:48I mean, that's obvious when you think about it. But the example we talked about in this episode is I kept flaking on a friend when I had a kid with chronic illness who was at home all the time. And I had a friend who didn't have kids and we'd make plans and I'd cancel at the last second and I'd make plans and we'd cancel at the last second. And then we kind of grew apart for a couple of years. And now, you know, that phase of my life, that season is behind me and we're spending more time together. But it affected our friendship for a couple of years because I never took the bull by the horns and said, so look, I know I'm flaking on you.

3:19I know it must be frustrating. Here's what's going on. I mean, she knew, but she didn't really get it. Like, hold on. This isn't about you and me. I'm sorry. I'll be back. But this is a tough time right now. And not having that conversation affected our friendship for several years. And why didn't I just have that conversation? So I offer that as getting to this episode, like there are some, you know, bumps in the road that you can probably talk about ahead of time with your immediate family and with your extended family that make this better than just well, this will probably be terrible again and not saying anything about it.

3:52I think that's true. And I think the opposite is also true, which is there are a lot of things that are better left unsaid. I was just on a or if you try to say everything, it's going to go badly, I think is what I'm trying to say. And I was recently an extended family wedding. And we were having the kind of brunch afterwards. And someone said jokingly in reference to something that had happened at the wedding, a rule, which I had never heard from it before. I believe it's from the recovery community, and it's a three-part rule. Number one, does it need to be said? Number two, does it need to be said right now?

4:27And number three, does it need to be said by you? And I think when traveling with extended family, we don't always need to have the conversation of like, Amy, I need to talk to you about how insensitive you are about your behavior that is being seen on this vacation. And I think sometimes the frustration of extended family is that I say this with love, it's totally fine to talk behind my back. Like you don't have to bring to me every issue that is in the family. We don't have to work out all of our family issues to gather twice a year as a family. We don't have to hash it out. No. And you're right.

5:04Like this is not the time to try out that new boundary setting language you saw on Instagram last week, right? With your sister-in-law. It's not. But on the other hand, like if you know that your kids have a bedtime and your sister's kids don't, and you're in the same house, rather than everybody like crackling with why are they like this, it might be better to kind of talk about that ahead of time. Like, hey, so you know, our kids have different bedtimes. How do you think we should handle it? Have an open-ended conversation about it so that both things can be true. And like, hey, for us to have a good time, we need X, Y, and Z to happen.

5:38And so how does that work? But that does not extend to, Amy, I have noticed that your husband is terrible. Like that conversation does not need to be. By the way, I love Amy's husband, but I'm using this as an example. Like we need to have the right conversations that are helpful and not have the conversations that are, why don't you ever discipline your children? Like it's a little bit of a balance between what conversations we do and don't want to have. Well, I guess I would argue that having the right conversations ahead of time can in some cases make it unnecessary to have those unpleasant snippy conversations in the moment by clarifying ahead of time.

6:23Yes, I think that's probably true. And I think that in the long term, I have learned that your opinion about someone else's lifestyle, parenting or overall choices is fundamentally not welcome. Speak about your own needs. Don't ever speak about other people's choices. Does that make sense? Yeah. Like your kids would be better behaved if they went to bed before midnight is not something you need to offer. Right. But if they're keeping your kids up, it is your business. my children I need my kids to go to bed at 9 p.m. I think you got to keep it on your side of the fence but like oh god your children never seem to eat vegetables not welcome to keep it to yourself so the first person you probably need to talk about all of this ahead of time this is from Katie our listeners in our Facebook group had some excellent ideas around this so I'll link to the original post because it's great Katie said that the first person you have to sidebar with before you go is your parenting partner.

7:21If you have a parenting partner that you're entering into this with. Obvious, but yes, do it, do it. Sit down and talk about it. And I loved this advice. Katie said, have a conversation in advance about which relatives on the trip can supervise the kids that you're bringing on the trip and which relatives are entertainment, but are not supervision. Like if grandma is not really capable of watching the kids while you go out to dinner anymore, but she is capable of hanging out with your kids and coloring while you make dinner. That's a conversation you and your parenting partner need to be on the same page about before you ever get to the share house.

7:56Yes. And I have a tip about this. When my kids were little and not water safe, when we went to any water based or really any activity, even at a amusement park or something there, I got one of those plastic bracelets, rubber bracelets, you know, that for every cause. Yes. Yes. You've told us about this, right? And you wear the bracelet. If you are in charge of the child, you wear the bracelet and you might get one for each of your children. And because what I find happens often on the extended family vacation or there anytime there's 10 people in charge of the kids that if I have an 18 month old who's not water safe, that's a very different watching job than like, oh, you know, count the kids heads every 10 minutes in the pool or something like that.

8:42And there was no lifeguards at the pool we happen to be at. And so I was very strict about like, if you are wearing this bracelet, when I hand it to you, until I take it off of you, you are in charge of this water unsafe child. Because what I don't want is I yell over to the bar like, hey, someone watch the kid in the pool. It's not safe enough for me. Yeah, no, I've been in that situation with kids falling in the pool and kind of nobody's watching. But you can't show up with bracelets at the, you know, family events, start handing them out. But you can do this with your parenting partner ahead of time, or maybe even with your sister ahead of time, like, hey, would you like to do this thing with me?

9:18Right? Like, this is definitely an opt in, not in the moment thing. Or are you saying it is you show up? Yeah, for sure. And I have showed up and just said, here's how we're going to handle this. So like, if I give you this bracelet, it means you're in charge of the kids. And it also kind of, I mean, this wasn't really relevant in my situation. But like, it would also help with the thing of, I'm not going to hand it to like the guy who's had 10 margaritas already, you know, like I think it, it helps. Well, so there is one time I can remember we were on a family vacation, lots of little cousins around shared house, and it wasn't the pool, the pool, we had a gate around.

9:52But the one thing we didn't think of is like, they're all here, the kids are fine, kind of nobody needs to be watching them. A couple of kids ended up in the driveway, got in a car to play and then couldn't get out with the windows up on a sunny day. And they're in there for like 20-30 minutes panicking and trying to get out before they thought to start beeping the horn at which point you know somebody eventually it was okay it could have gone another way scary really scary yeah you do need to be intentional on these trips where there's like you know five kids under eight somebody needs to be on duty instead of kind of everybody's always doing it and that requires a system of some sort that and then the system needs to be in charge not you not like father the clock, it's Jason's turn to wear the bracelet.

10:35You know what I mean? But there's a system that you agree on, but it needs to be deliberate. It can't just be, it'll be fine. I think that's right. And I think that the other thing that will happen otherwise is that one can become the default by simply being like the person who's most worried and that ruins the vacation. Like the thing of, we've talked about this before, like, oh, why is Amy so uptight that she can't even relax at the party because everyone else is drunk and there's five kids under five. And, you know, I don't want to be at a party where my kid gets hurt and I don't want to be at a party where any kid gets hurt.

11:08So if we're all on a boat and like the kids don't have life vests on, I am going to ruin the party by being like, we're not going or this doesn't make sense to me. And I do think that before you go on the boat, some of this has to be done kind of on the fly because events come up. But I will say I'm not comfortable with any kid being on a boat without a life preserver on period end of story And i'm not going to be on a boat where there's kids without life preservers and my kids are not going on a boat Without life preservers on and I think sometimes you have to make kind of uncomfortable stands But I think when you come at it from the point of view of like this is my comfort level This is what I would like to see you can kind of start a conversation that's not an attack on somebody else.

11:57And the boundary is this is what feels right for us. So we can't go on that trip. My kids can't go unless there's life preservers. That's not saying nobody's kids can go, but you're setting something that works for your family. And hopefully you and your parenting partner ahead of time are like same team, same team. If you think it's probably fine that they go without a life preserver, we don't have that conversation in front of the kids or in front of our brothers-in-law. Yeah. Yeah, and I think it can be tricky if where it starts to get tricky is it's okay for your kids not to wear life preservers.

12:26It's not okay for mine. Why does he have to wear it becomes like the theme of the trip becomes a lot of talk about who is and isn't wearing life preservers. And so I don't know, it's tricky. You can't make overall statements. I try to work from like place of maximum generosity, like that safety first, but then I can think of an example where it's like, we actually do want to have some fun. Like it can be hard to balance everybody's needs and wants because there are people who are too protective and it's like, well, we actually do want to just like hike up the hill and we don't think it's dangerous.

13:04It's hard to make blanket statements about it, I guess. Caitlin says, this is kind of related, anticipate conflict between people on the trip who prefer a looser schedule and those who are on a nap schedule. Caitlin says, I was told to take a chill pill. And this is another version of what you're saying. Like, so the baby needs to be in her crib for a nap or we're all going to pay. And then you get to make, you know, to take a chill pill. It can be difficult to be the one who is doing the forethought in these situations and then being told to relax when you know if the baby does a nap in her crib, you can't enjoy dinner tonight because she's going to cry and you're gonna have to walk her outside till she falls asleep.

13:39Like, it's frustrating to be told that you're uptight for thinking ahead. But sometimes you've just got to talk about that ahead of time, I guess. And be like, this is what we're going to need. Sorry if it's inconvenient. And the reality is there are super competing interests, right? Because I've been the person with the baby and I've been the person with like the three kids who are eight, nine and 11 who on a rainy day are not going to be silent for two and a half hours during your baby's nap time. Like we have actually competing interests. and I think that you have to, I think I do have a take on it.

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17:11No appointment, no going to the store, no upsell at the counter. I also used Zenni's virtual try-on to see exactly how my new tortoiseshell square sunglasses would look on my face before I ordered them. Let me tell you, they looked super cute on the virtual try-on and super cute in person. And with frames at under$30, I got a second pair just because. If your glasses are overdue for a refresh, now is the time. Go to zenni.com slash podcast and use code podcast15 for 15 % off your first order. These styles sell out, so don't sit on it. That's zenni.com slash podcast, promo code podcast15. I think part of the challenge is that you have to realize that things on vacation are really not going to operate the same way as things operate at home.

18:05You know, like the baby is not going to get a three-hour nap and the kids are going to eat probably later than you do at home. And the grown-ups aren't going to eat at eight, right? And the grown-ups who are like, but we always eat at eight. Like, well, not on this trip, you're not because the grandchildren are here. You know, that everybody's going to have to compromise, not just you. Right. Or the grandchildren maybe get chicken nuggets at six and the adults eat at eight. Like, and I think the biggest thing I would say about vacationing with extended family is hold things lightly in terms of like, something, things are gonna go wrong.

18:39It's part of like what you're modeling for your kids. It's like, we do things a little bit differently because of how much we value this time with extended family. And I think another big mistake that people make on family vacations is, it's all about spending every minute together. And like, that doesn't work. Like, okay, so if, would it be possible at nap time for the bigger kids, like that's a good time to take them to the pool if we want quiet for this hour. But if it's raining, that's going to mess up the baby's nap because the kids can't be silent while the baby naps if you have a silent household.

19:16Like, I think that things are going to get lost during the course of the vacation that are part of your normal daily routine. So the planning separate time was an entire category of advice that people gave for this. Emily said communicate expectations before the trip agree that it can still be a great group trip without everyone doing everything together all the time. Emily suggests maybe everybody comes together for one big meal a day. This is what we tend to do like dinner is going to be at six and this person's in charge tonight or this family's in charge tonight. Keep it looser about who's participating in what for the rest of the activities.

19:52Anna said you can plan something you want to do. You can put it out there like, hey, tomorrow Jimmy and I are going to get up and we're going to go on a hike probably about 830. We're going to leave before it gets too hot. If anybody wants to come, we'll be outside at 830 and we're going to go and then leave at 835, you know, and there's no expectation and you hold it lightly. And there's no forced march on a hike that with kids saying they're hot, we didn't want to come. They don't have to go. Right. And I think holding lightly also has to do with I'm fairly strict at home about my kids bedtimes and to some degree eating.

20:23And I just let go of those things on vacation. My kids often stay up until after midnight when they're with their cousins. and they love to hang out. And, you know, for them, I think it feels very crazy to be like up past midnight on the trampoline with my cousins. And are they more nightmarish and they get sick and stuff? They do. And that's just, I just build that into the formula or I just kind of accept it in advance. And yeah, but I'm here. I'm speaking for the 18 month old who's going to get up at 5.30 a.m. whether she goes to bed at 7 or goes to bed at 10.30 because it's fun and what do you mean and you know like that is because you're holding the bag that's what I'm here to hold the line for if you're the one who's gonna have to be up with the cranky kid or miss dinner because of the cranky kid yeah then you have a right to say this isn't how it's gonna be but what is the solution it's to take the baby you have to I think then plan to have a quiet space to take the baby It's planning.

21:22Ella says, give everyone a sense of your daily rhythm. Can you tell I've also been told to take a chill pill when I use routine or schedule? She said, tell them ahead of time so that the early risers aren't shocked or the night owls or the people who haven't parented lately. Like, this is how it goes. Or if we're serving dinner at 8, you guys can't come back from the bar at 9.15. The kids, dinner's gone. We served dinner and the kids ate it all. I'm really sorry. That there is a schedule for people who weren't used to being on a schedule. And it's not a schedule that everybody has to adhere to.

21:52but the couple with the baby has to adhere to it. I think that's reasonable. You can't just be like, eh, it'll be fine, because it won't be. What those people don't understand is that your kid's not going to sleep until 11 the next morning like theirs will. Right. I think it's thinking of like how the space is laid out. That's right. Making plans for it. Because I think that the conflict sometimes comes, and I've been on both sides of this, from the, I think, young babies who are on a sleep schedule, you have to make really good decisions about where. Yeah, where that baby is. That is, you know, because I do think that the like, everyone has to work around an 18 month old on vacation.

22:29I see why that's frustrating to people as well. And so I think it's like, you have to solve your own problems, I think, to some degree on this, like, okay, this bedroom that is near the playroom is not a good bedroom for us with the 18 month old. Like we need to, I think the conflict often comes with like, people feel like the person with the baby is like, this is the first baby that's ever been born. And like, we have to, now this is becomes a 20 person vacation dedicated to the care and service of an 18 month old, which I understand why is frustrating to the group. But at the same time, yeah, chill out your baby, you know, just go with the flow is not possible when you have an 18 month old.

23:12So I think you're right to say that like all those decisions happen before the fight ever happens, basically, in terms of like what gets the 18 month old the most sleep while letting people feel like they're on a vacation and can relax. Let's talk about divvying up responsibilities because most people seem to think that some sort of discussion of that ahead of time, some sort of Google Docs spreadsheet, handwritten thing is in order for planning meals for an extended group of people. Do you do this when you travel with your extended family? We do, but it's 25 people. Like at some point, it's like this isn't funny anymore.

23:49and one person can't, or even three people can't possibly do the cooking and cleaning and planning and shopping for 25 people every night, unless that's a paid staff that you're having as part of your vacation experience. We don't have a staff. We did do that once. We went, we, all of us went to a villa that had a cook who would cook for you and a staff. It was incredible. It was the best vacation ever. Just be like, oh, like lunch is ready. So I think what we're landing on is get a staff. But if that's not available to you, barring that a Google spreadsheet. So we do a Google spreadsheet. And you know, guess who starts the Google spreadsheet?

24:25Yes, it's me. I start the Google spreadsheet. But I just it's the same one as last year. I'm like, here, it's a version for 2024. And everybody during this like five or six days we spend together get a lunch and a dinner and they can pick when it is. And you can cater it from the pizza place if you want or the barbecue place or you can bring frozen lasagas. You can do whatever you want, but you sort of, you're in charge. You grab it. And what's good about grabbing it ahead of time is that you get, you call lasagna, you call pasta night, whatever. And now it's like, oh darn, they already picked a pasta night.

24:55So now I have to come up with like Mexican night or whatever. But there's a benefit to going in early and then you stay out of it, right? Then it's like, if anybody needs anything, you let me know if you're the one, if it's happening in your town, try to stay out of it as much as possible. I find like that's very useful. And again, like if you're the one with the vegetarian kid, if you're the kid who's gluten free, you kind of have to hope people think of it and make sure your kid has what they need. When your cousin thinks that turkey lasagna is vegetarian, you know, that stuff happens all the time.

Read the full transcript

25:26Right, right, right, right. Yeah, we tend to go, we roll a little bit in terms of like, and we have 20 at one of them. I feel like it we do a lot of, we don't cook a ton and everybody kind of likes to cook. So it tends to be a little bit of a fight for the nights that, I mean, my brother-in-law is a cook. My sister-in-law is an amazing cook and likes to, she just puts together like, she's got a crazy little like catering thing and she puts together like tacos and whatever. Everybody's pretty good about cleaning up and stuff. I think that the spreadsheet probably works. I'm talking about like nuclear families.

26:06I think when you get like cousins and other stuff involved and people with different styles, it might be easier to do on the spreadsheet and plan ahead. I think whenever there's conflict, go back to more planning. That's what I think. Right. The system. Laura says, I wanted to highlight this because I think it's common, but I think it's a little bit of a trap. Laura says, plan out meals ahead of time. My mom and aunts do a really good job of this on family trips when we share a house. It shouldn't be on the mom and the aunts or the you to do all of the meal planning. And, you know, don't let that happen.

26:36We try to make it, it's this household that's in charge of lunch and dinner. And I don't care if the teenager does it or the dad does it or all three, but it shouldn't be, okay, now all the ladies decide what we're having for dinner every night. If that's happening in your house, it's an opportunity to revisit that and maybe reassign some of the duties. You do the cooking, but your, you know, your brother and your cousin go do the shopping then. Right, right. I think that's right. And giving voice to that. We, I'm realizing we go to the same place. We have one that happens in Florida, one that happens in Texas, one that happens also in Texas, but at the lake.

27:09And I feel like there are such set things that everybody wants there that it's like, okay, we're going to have this night and that night because we repeat the same locations. I think that does make it easier than like we're all going on vacation to a new place. Because in Florida, we got to have an Outbacks night, we're going to have a night where we do the grill, we got to have the night, we just have very set. And so if we're there for seven days, sometimes it's hard to fit in like our seven favorite things that we do when we're in Florida. And that's different than like, let's go to different places.

27:43What about expenses? This seems to me to be a little bit of a third rail. But again, that's why you put a system around it, because then the Google spreadsheet reflects tax the expenses, how much people are spending on what, not, you know, your own resentment. Anna says she starts a spreadsheet, so everyone on the trip adds up what they spend on shared groceries, meals, activities as we go along, and then they settle up at the end of vacation. Yeah, I think that makes sense. And I think it also, it's fraught. I mean, there's a reason why this is hard. It's all really fraught, like, because you're coming in with the, everybody is walking in being like, here comes the lazy one.

28:22Here comes the uptight one. Here comes the one who always ruins the vacation by fighting with her husband. Here comes the poor one who never puts in. Oh, she's rich. Why doesn't she contribute more? Like, there are so many expectations that come into the space. And then, of course, everything seems to be like, oh, there she goes being lazy again, because she's the lazy one. And it's like, there are just time bombs all over the place. So I do think that neutral systems in the way that we say, like, the lady tells you to leave the park when the phone alarm goes off, the phone alarm is telling you, the spreadsheet is telling you this.

28:59It's not uptight cousin Maureen who's telling you this. It's the spreadsheet. On the other hand, just take the flip side of that. Emily says, no one to step back and let the aunt take over. It doesn't matter who arranged things. Everybody has an aunt who is just used to running things. And sometimes the best thing to do after she announces her meal schedule or whatever is to just let her. I mean, if everybody's good with that, including the aunt, then I guess that is okay. Sometimes you don't have to create a system when when the system of the aunt does everything is working fine. But I would, I would circle that and underline that and maybe ask the aunt about that.

29:32Yeah, I guess so much. Yeah, I guess that's right. But at the same time, like you, right, I think sometimes people feel better to be in charge of everything, it helps them worry less and like let them. I find that even with my mother, who's a therapist, used to say this, like even with passive aggressive behavior, you kind of have to take behavior as it comes in. So it's like if you're running everything, and I've asked three times what I can do to help, and you've said absolutely nothing, I'm going to go relax. Like I've offered to help, but I'm not going to go in and be like, is this really okay?

30:08Like it's like everyone's got to run their own show to a certain degree, I think. I have done hosting of extended family where I did 100 % of the shopping, prepping, cooking, cleanup, you know, let me do a dish for you. But I was, I never left the kitchen. And it took, again, I think this is a conversation that happens outside of the moment. It took my sister-in-law, a new addition to the family to say, hey, I noticed last time we did this that you were in charge of every meal. That seems nuts to me. Why don't we start a spreadsheet? And I said, oh, that'd be great. But when you're talking to me when I'm like up to my elbows and walking tacos, I'm like, I'm fine.

30:46I'm good. I'm good. Right. Like, go find the kids. Right. But when you can talk about it in a neutral moment, yeah, sure. I'd love to do things differently. You mean we can do things differently? I think it's just not a discussion you can have in the moment. Makes a lot of sense. I have another thought about that. We'll be right back. Oh, Amy, between swimming and sweating, summer is basically bad hair season at my house. But we found a solution. It's Nutrafol. Nutrafol is the number one dermatologist recommended hair growth supplement brand. And it's the number one hair growth supplement brand personally used by dermatologists.

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32:46And now, things you will hear on vacation with your extended family. from the What Fresh Hell podcast. You're going to the gym? I thought this was a family vacation. We do things together as a family. Oh, look, somebody left dishes in the sink. Oh, look, here I am doing the dishes. The only one who ever does the dishes. Wait a minute. Who put family hike to Mount Graham on the schedule? I did not agree to hike. If we are going to keep score during charades, I do not want three five-year-olds on my team. Put your wine coolers in a Stanley cup. Grandma doesn't know we drink. Why am I in a condo with a baby?

33:25I already put in my time with my own babies. I come on vacation to sleep. Listen, we all heard Stacey and Bob's blowout drunken argument on the lanai last night. But at breakfast, we are all going to pretend that nothing happened. We forgot the birthday cards for Aunt Joan. Quick, have the kids make a banner so it looks like somebody remembered. I thought we agreed we weren't going to talk politics. Well, I think you are charming. I have no idea why cousin Carol says you're stuck up. I don't see it at all. Oh, God, it's Phil's turn to cook tonight. Hope everybody likes cheeseburger surprise. Why did we agree to this again this year?

34:05It's only Tuesday. This has been Things You Will Hear on Vacation with Extended Family from the Wet Fresh Hell podcast.

34:18So before the break, we were talking about communication. And I think one piece of this communication is whether or not extended family vacations are the default and whether or not you want to participate in them. Like that's part of the discussion, because I think for my family, we tend, because we're far away from family, to do all of our breaks with members of our family. and at a certain point my husband and I kind of realized like we don't spend any time vacationing the two of us and we don't spend a lot of time vacationing with just our family and we kind of made a little correction around that like oh we do want to spend some time with just we don't want every single time we take a break and a vacation to necessarily be a long extended trip with family, despite the fact that we love and adore our family and our extended trips with them.

35:13Linietta Willis, right? Dr. Willis talks about stable misery. Like, be careful that these vacations are not just stable misery for you. Like you can actually make different choices. You can go for a shorter period of time. Like you do it because it's supposed to be fun, basically. This takes the honest conversation. We go to the Jersey Shore every year because that's what we do. We go to the Jersey Shore and you're like, I don't want to do this anymore. It's worth questioning that if the way you do things every year is the way you have to keep doing things. We just did this in my family. We tend to do the same thing every year.

35:45And we had a discussion that I tried to make a really open one to this large group of people. We don't have to do this again. We can do something else. And then everybody kind of agreed. We have some big birthdays coming up next year, summer 2025. So we said, let's do the default for 2024 and we'll try something new and big for 2025. But at least we had the conversation. I think it's important to not assume that the couple with the three-year-old and the one-year-old want to make the five-hour drive that includes a ferry again this summer. Yeah, ask the question. And vacationing with any 20 people, you could pick them out of the phone book.

36:21It's going to be annoying to some degree. Like 20 people are not all going to get along perfectly. And I think that it's part of the deal to choose it, you know, and to say, and I do think it's very important to model for your children that like there are people in our lives that we celebrate with on a regular basis. And as I get older, one of the things I admire about my extended family is how well that was modeled to me and like what valuable relationships have come out of it. But you have to kind of put a fine point on it because otherwise it just becomes like we get together so I can talk about how annoying cousin Bob's wife is like that.

37:02Why are we doing this? Stacey has some really good advice around this. She says you have to take time with your nuclear family as needed. Make sure you're doing that. Go for a walk just you so that even within this family vacation you have that time. But here's the truth bomb from Stacey. Know that not everyone is a good traveling companion no matter how much you love them. And vacations are meant to be enjoyed. So you don't have to love every moment with Uncle Bob if Uncle Bob is impossible. You do have to maybe tolerate family dinners, but you don't have to go birding with Uncle Bob if your kids want to be at the pool.

37:41You definitely don't. And I do think that, I mean, I said it in the beginning, but I do think this is a place where we are called on, if it is an important value in your family, to interact with extended family. It is a place where we are called to our place of maximum generosity writ large, which means both making it work for yourself, setting whatever boundaries. It doesn't mean you have to go be a doormat. It doesn't mean you have to go be abused. But in choosing to participate in extended family, it does come with, and I know, I think it's difficult. I think I've cited this before, but in her book, Glennon Doyle talks about, I think it's Maya Angelou, going to somewhere where nobody's walking on the rug.

38:26And she's like, she assumes it's because people think that they're not good enough to walk in the rug. So to show that she doesn't believe in this stupid hierarchy that everyone has established, she walks all over the rug, and then they have to clear the rug and bring in a new rug, and then they serve the food on the rug. And it's like, she just came in so hot to be like, and Glennon Doyle says, like, this is how I approach my in-laws in the beginning. And I realized that, like, I came in and everything was like, I can teach you how to do it better. Look at how dumb the way you do things is. And like, your traditions are stupid.

38:58And the way you treat each other as wrong. And that I do think that you have to go into these situations with a certain degree of grace. And it is fine to go afterwards and call your sister and be like, everything that everybody does is crazy to me. But I think that if you go in to be like, well, this is a stupid time to eat in this, but like, I would try to let that go. It's not going to make the vocation go better for anybody. I think it's that you have to choose your non-negotiables and you need to be able to count them on fewer than three fingers. Oh, that is good advice. So you need to have three non-negotiables.

39:32You need to be able to count them like on fewer than three fingers. And that's probably per family. So say when I travel with my family, my spouse is a super healthy eater. I know that he's not going to want lasagna and then pasta and then pizza and then grilled cheese. And it's not going to be what food he wants. So we prepare for that. We talk about that ahead of time. And then I make sure there's something that he's going to be willing to eat. And then he's in charge of grilling that or preparing that if what's for dinner is not. And we talk about that ahead of time. The baby that needs to be in the crib for her nap time.

40:02That's your non-negotiable. And that's what's going to happen. And then you can be totally loosey-goosey about is the food healthy and is the beer the kind that you like, right? You're non-negotiable. You talk about it with your parenting partner ahead of time that your kid who is on the spectrum is going to need some time to, you know, to download on their own and be away from stuff and sort of recharge. That's a non-negotiable. the kids are allowed is not really something that you can demand change around has to be really specific or your non-negotiable is clear enough that like we're not going to stay in the main house we found a great little hotel down the road and like that's better for us because then we can manage the baby the way that works for us like whatever your non-negotiables are I think that's right if you have a small clear number of them you make the vacation work for you and then you participate in everything else, but it doesn't become a constant negotiation of like, actually, we don't want this food.

40:59Actually, our baby needs this. Actually, my kid wants. It's that you kind of know your non-negotiables and you figure out how that's going to work in this context. And you start with your parenting partner about your immediate family. And then maybe you have the discussion. Oh, hey, I was hoping one night that we could, I was really with my husband four times a year because we don't have any babysitting when we live. So I was really hoping that one night we could do that. And then the next time I'm happy to listen for your baby and you go out, that's a non-negotiable for you. Then you can come with the problem and the solution.

41:33There's not enough alone time for you on this trip, right? Here's an idea. How about we all give each other alone time on this trip? And I can't imagine anybody would say, no, thank you. Yes. Yes. Except for maybe the person who's like, but I thought we were all going to spend all of our time together. There's always something. There's always something when traveling with extended family, but we solved it, Amy. Well, I wanted to give you this takeaway from Leslie. Leslie says, go into the vacation knowing that things will be hard, comments will be made, and people will get on your nerves. But if you have each other's backs, you'll at least be set up for some success.

42:07Parenting on vacation is hard enough. Parenting with an audience is even harder. Hashtag agree. Yeah. Well said, Leslie. Hashtag full agree. And here we go. Here comes summer and here come extended family vacations. I'm looking forward to mine. I really am. Absolutely. It's worth it. It's worth all the planning. Absolutely worth it. So much fun. Did you know that we have a YouTube channel where you can watch us recording this show? You can also watch little clips and videos. You can subscribe and follow. And we would really love you to do that. We're trying to get to a thousand followers on YouTube.

42:42Some say we're crazy. We're going to do it. Watch this space. We just want to. So who says we're crazy? We can definitely do it. Search for What Fresh Hell podcast on YouTube and you will find us there to subscribe. And with that, thank you so much for listening and we'll talk to you next time. So long.

43:10to monday.com. Feel the sensation of an AI work platform. So flexible and intuitive, it feels like it was built just for you. Now open your eyes, go to monday.com, start for free, and finally, breathe.

From the publisher

This Deep Dive series is all about tips to stay sane while traveling with family —immediate or extended, kids younger or older in tow, across the state or across the globe!

We've both traveled with our extended families over and over again, and have loved the memories we've made together. But different bedtimes, sightseeing styles, and mealtime expectations can lead to unexpected conflict.

Laura in our Facebook group wrote in to say:

⁠"Might be a fun episode before summer: large family vacation traditions. I'm wondering if there are favorite games/foods/tips/funny stories on going away with lots of members of your non-immediate family."⁠

As usual, our listeners responded with great tips for maintaining both organization and sanity when vacationing with extended family, and in this episode we discuss them all, including:

Which conversations to have ahead of time—and which conversations never to have at all

Systems for family vacations that don't fall on one person (or one gender) to execute

Limiting your non-negotiables as a nuclear family ahead of time

What Fresh Hell is co-hosted by Amy Wilson and Margaret Ables.

We love the sponsors that make this show possible! You can always find all the special deals and codes for all our current sponsors on our website:

⁠https://www.whatfreshhellpodcast.com/p/promo-codes/⁠
Learn more about your ad choices. Visit podcastchoices.com/adchoices

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