Same City, Different Versions of Me: Chicago

There are certain places you keep going back to and every time, they feel a little different.

In this episode of Navigating Between the Lines, I’m taking you through Chicago, but not as a travel guide. More like a timeline. The same city, but through completely different versions of me.

From a 17-year-old on a graduation trip…
to girls’ weekends and bachelorette memories…
to becoming a mom, building a business, and now watching my daughter create her own memories in the same place.

Because sometimes it’s not really about the place, it’s about who you were when you were there and who you’re becoming when you go back.

We talk about:

• how places hold different versions of you
• the quiet evolution of friendships, motherhood, and identity
• blending work and life in a way that shapes your kids’ experiences
• and what it really means to be present in the moments you’ll one day miss

If you’ve ever had a place that feels like a time capsule of your life… this one will hit. And maybe it’ll make you want to go back.

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Transcript

SPEAKER_00 0:00

Hey guys, welcome back to Navigating Between the Lines. First, I just want to say thank you for all the messages after last week's episode about friendship breakups. I got a lot of DMs from women saying things like, I thought I was the only one going through that. And honestly, I've said it many times, but I think that's the whole, I don't think I know that's the whole point of this podcast. Life has so many moments that feel isolating when you're in them. And then you talk about it and suddenly you realize wait, this is actually a very shared human experience. So if last week made you feel a little more validated, a little more understood, that makes me really happy. I also just created a sub stack where I will be sharing after moment thoughts for a little deeper into the behind the scenes because I feel like I record these episodes and then maybe like comments come in or message me on the side. And I'm like, okay, wait, I have all these extra thoughts. I think that'll be a really good place to share them. So I'm gonna link that and um yeah, subscribe. It's free. So follow along if you want there. And I promise I'll just make one quick readable note per week. It's not gonna be anything crazy. Okay, so you know how there are certain places in life you keep coming back to, maybe like a city. You could, it could even be a country. And every time it feels a little bit different, but you can't quite explain why. I've been to Chicago so many times, all different seasons of life, starting in 2004. And now, you know, this last weekend celebrating Chloe's 10th birthday there, that's just so fun for me. I love that she loves Chicago too. But I was thinking about it, and you know, same city, same streets, same restaurant, same lake view, but every version of me that's been there, that's visited Chicago has been completely different. And I really started thinking about that on this last trip, how certain places don't just hold memories, they hold different versions of you. The girl who thought she had everything figured out, the one who was just trying to keep it together, and one who was finally starting to feel like herself again. And going back, it's almost like you meet those versions of yourself all over again. I mean, same but different, but they're kind of like in the back of your head always. I feel like those feelings. So today I want to take you through Chicago, but not like a travel guide option, more like the different versions of me that existed there. And I have a feeling you're gonna see yourself in that too. I think first question is who doesn't love Chicago? If you're from the Midwest, chances are you've been there at least once, probably more than once. And if you don't live here, I'm sure there's a city close to you that's gonna feel like this too. Chicago is just one of those cities that feels familiar but still exciting every time you go. At least I feel like that. It's big enough that there's always something new, but it's also just comfortable. Doing the drive in, it's three hours from where I live, exactly. So doing the drive-in never gets old. When that city comes into view, you know what I'm talking about. It's just so beautiful. It's like flying to New York, too. You get when you see the city, you're like, I don't know, it's just feels like exciting. So much opportunity lives there. And being there this weekend, thinking about this episode a little bit, I realized every time I've gone to Chicago, it represented a different phase of my life. The first time I ever went was right after I graduated high school. So, you know, summer of 2004. Aging myself. But my Aunt Karen, shout out, Aunt Karen, she took me, my grandma Marge, and my cousin Kate. And Aunt Karen, she actually lived there. We actually have never talked about this, so I should get more of her perspective on this. But she lived in Chicago when she was younger. So I know it was a favorite, it is a favorite spot for her too. Looking back now, I'm sure she was probably feeling a little nostalgic being back there too at that time. But there are certain things about that trip that I remember very clearly. One, we walked everywhere. And when I say we ate our way through Chicago, I mean we ate our way through Chicago. I was, you know, 17. And so if I was 17, my cousin Kate was 16, right? We loved the same things. Bread baskets, like our lives depended on it. Huge slices of chocolate cake, you know, like the the ones that are like this tall. Yeah, we had, I think, you know, whatever dessert I can remember taking the to-go and just sitting in the sun. We were by the lake and crushing that piece of cake. I know there are some photos of all this somewhere, but remember also that was a time when you had either a disposable camera or film. Everything was on film and you had to go get the film developed. My aunt's actually traveling this week. I was gonna poker for some photos, but she would have to comb through the her boxes of old photos. So we don't have those, but that's okay. The memory is there. Hopefully you can envision it, you know, just like the best. And of course, even then, we went to Ed DeBevix. It was my first, well, obviously my first experience going to Ed to Bevix. If you've never been to Ed DeBevix, the whole concept is that the servers are intentionally rude to you. Like that's they're just very sarcastic from the time you walk in the door to the time you sign your check. They'll roll your eyes at you, throw napkins at you, tell you to sit down. I guess I can't remember if I knew that was the case before going in. Like I'm not sure if anybody prepped me for that, but I just go remember walking to this old school diner and they put these hats on your head and they were like, sit down highlights. And I they kept saying, Grandma. So also, the other thing, it's typically a bunch of like actors or people who are working on Broadway too, trying to make a name for themselves, work in this restaurant. That's how it used to be. I think probably that's still how it is now. But our server sat behind like the DJ booth. It wasn't a DJ booth, whatever, the old record booth singing a song, whatever he was doing, and he'd go, and grandma, and he kept saying it. And anyway, Grandma Marge loved that. I loved it. We were all laughing so hard. And what a memory for, you know, the three generations doing that. We should go. Side note, you guys, Aunt Karen and Kate, we should go again, the three of us. So also fun fact David Schrimmer from Friends. Is that how he's pronounced his last name? He waited tables there before he started on Friends. Everyone starts somewhere, and just a cool, fun fact about that place in 2015, they shut down their old location and it reopened now. It still holds the same style, but it's like an updated vintage, if that makes sense. Current trying to be 1950. I think it's still the best. And Chloe loves it. We've been there several times now. But what I remember even more from that trip was the hotel. I can't tell you what hotel it was this big downtown hotel, though. And I remember thinking, oh my gosh, this is so fancy, this room so big. Because that just wasn't a huge part of my childhood. We weren't constantly staying in hotels and going out to dinner every night. So that whole experience, what a good graduation gift. Now that I'm thinking of it, by the way. But the whole experience I can remember felt really exciting. Like, you know, we're going to Chicago on Monday or whatever day that we went. And it's funny because at that age, I don't think you realize those moments are quietly shaping you. You just think you're on a trip. But really, you're expanding what you think your life could look like. It opens anytime you go to a new place, it opens your eyes to just a much bigger world. And I think that's one of my favorite parts of traveling. And also, that's when I first fell in love with Chicago, for sure. Fast forward a few years or, you know, several years, and Chicago became the place for girls' weekends. I had my bachelorette party there. My mom and I bought my wedding shoes there. That was a really fun moment. And there have been multiple friendships and more bachelorette parties. I'm sure you're thinking some of your own. You can think of some really good memories that you have from Chicago. And I think it's just that perfect location for that stage of life. There's great restaurants, great hotels. There's always a new hotel popping up, too. That phase of life where your friendships feel like everything, and you assume they'll all come with you onto the next chapter. Everything is mostly walkable, depending on your shoes. You go for dinner and suddenly it's midnight and someone ordered another bottle of wine and dessert, and nobody knows how we got there the next foring. Classic girls' trip math. Am I right? Then there was the time Chicago saved our baby moon before William was born. Justin and I were supposed to go to Miami for our baby moon. Remember? William was also born nine weeks early. So I this had to be just maybe like a month before he was born. But when I could still be on a plane, I'm trying to think the exact timing. The weather was insane. So William was born in March and must have been February. The weather was insane. All the flights were canceled everywhere. And we like our plan fell apart. We were not going to Miami. And I guess I don't remember how everything came about, but we were like, okay, let's just go to Chicago. Cause again, you can get there in three hours. So we repacked and went to Chicago. I remember walking around the city all day. We shopped and ate. And when we went to bed that night, my legs were cramping so hard. So it was one of those things, like, in hindsight, if you're planning a baby moon, go somewhere where you can just sit somewhere. At least that was not my experience. I thought I was gonna die. I remember I was like, we might need to go to the hospital because I just had these cramps everywhere. Probably was just a little dehydrated, but you know, being in a city pre-parents is just different. Those quiet little trips before kids are something you really appreciate later. Okay, wait. I feel like your Chicago personality also says a lot about you as a person. Like if you're a deep dish girl, you're probably committing to the plan. You made the reservation, you're wearing the outfit. If you're a thin crust girl, you're like, we'll figure it out when we get there. I think I'm a mix of both. If you're doing the architectural boat tour, architecture boat tour, you're in your, I want to learn something new era. And if you're skipping that and going straight to a rooftop, you're in your, I just want a vibe and a drink era. And honestly, I've been all of these versions at different points in my life. The dressing for the vibe to dressing for walking 20,000 steps, wandering around Lincoln Park. Like who lives in these massive places to bumping into every store on Michigan. There was a phase where I packed outfits for the photos, probably. And now I pack for comfort. And how long we're going to be in our feet? You can mix it up. You can do a little bit of both. You can like look cute and still be comfortable. But girls' trip chaos or hitting a full spa to recharge. That's been a more recent step for me. I just, you can do anything there. When I became a mom too, well, I was lucky that my career completely molded into what I needed to be. So I could be so immersed into mom life, but I was also building a business. So when I owned Renee Austin Wedding, you have to go to market a couple of times a year. And Chicago holds the merchandise mart. So, you know, when I was navigating all of that together, like building a business, becoming a mom, I guess I knew I wanted to incorporate that. Like I called myself, I used to call myself a mom preneur, literally navigating between the lines back then. But William went to Chicago for the first time when he was a baby. We took a babysitter and had the best dinners. So, you know, I worked during the day, did like all day buying, and then, you know, go to dinner and I'm a mom, you're in bed by 8 p.m. while your baby's in a crib, probably like in the bathroom. Then, you know, then I had Chloe. And when she was a baby, this is like a side story, but she would not take a bottle from anybody. Like she just, she was a boob lover. I'm sorry, I'm gonna say it. She just refused anybody but me. I mean, I guess when she went to daycare, she would drink a bottle and from my mom, and those were the only two people that could get her. But I remember before I knew I could bring my baby to market. Like, I don't know, I was just still so young, you guys. I didn't, I was just trying to figure it all out. But I took my pump and I can remember sitting in a stall, like a bathroom stall, pumping. Like, what's just trying to figure it out? Like, how can I be this leader and also a mom? Well, you figure it out. And the trips just kept evolving as the kids got older. Chloe went and I just realized that everybody loves the baby and they'll hold her. Well, I'm looking at this fabric or, you know, watching the fashion show. They don't mind if I'm holding a baby. So it all worked out. And then the kids got older and we made it a family trip every fall. So the kids got to see the Navy Pier, shed aquarium, and walking back to the hotel with kids asleep in a stroller. If you've ever walked back to a hotel after a long morning and your kids fall asleep in the stroller, you get this. But Jess and I had plenty of times where that happened and we'd be stopping at Nordstrom and grabbing and grabbing a glass of wine at the bar. So you're getting the best of both worlds. Those stroller naps, oh my gosh, those were great. We've done Cubs games. We did spring break there with my mom, too. Um, I've done a down and back for a comedy show. Chicago just has always been one of those easy weekend cities for us. Trying to get out of town or make a plan, just go to Chicago. You can take the train. Again, it's three hours away. It's just simple and there's always something to do and always a really good food to eat. And this past weekend, for Chloe's 10th birthday, we went and crazy because double digits, like I that's hard for me to wrap my head around. I have two kids in double digits. But I will always do a birthday trip, I think, over, you know, I always say, like, do you want to have a birthday party? What do you want to do? And when I asked her what she wanted to do, she said, I want to go to Chicago. I shared her birthday itinerary on the Navigating Between the Lines page. And it's just, it's so her. She's such a vibe. When I tell you she wore an It's My Birthday headband for the whole weekend, she wore it for the whole weekend. And I think now I can say Chloe's building her own memories there too. I mean, now she's been going to the city for 10 years, which is crazy. You know, she's 10 and already has a preferred hotel pool in Chicago, which feels a little wild when I say that out loud. Because while I grew up going on spring breaks and there was no shortage of experiences, it was more old-fashioned style, like snacks are packed in a bag, music's loud, the windows are down. I had a Game Boy and we played endless I spy games. And then my kids, they're growing up in this version of life where my previous work and our life kind of blended together and became the lifestyle. Different experiences, different memories. And, you know, I'm just really aware of that in the best way. Like I tell them all the time, you're so lucky. You were so lucky. But okay, Chloe's itinerary. We ate really good dinners and it was all attention on her. We went to the ice cream museum for the first time ever, which was really cute. Have you been? Um, we did the VIP tickets, so you can show up anytime because they typically they do these like slots, these one-hour slots. So was it necessary the VIP tickets? Probably not, but it did mean we didn't have to stress about what time slot and getting into the city. It was like St. Patrick's Day weekend. Traffic was insane. So I think it was worth it. But if you're going on every other time, I don't know if I would say you need the VIP tickets. You did get a free t-shirt with it. Free. So that's kind of funny. Saturday morning, we went to Ed DeBevick's again, which, you know, at this point is basically tradition. And I told you Chloe wore it's my birthday headband the entire time. She also doubled up a St. Patrick's Day headband on Saturday. Her vibe is just, I like, I mean, I always say, Chloe, I want to be you when I grow up, kid. We stayed at the Langham Hotel. That was a first time for her. I love the service there. You guys, it was my second time staying there, and I highly recommend it. I think it's great for kids. It competes with all the other, you know, kid friendly amenity hotels. The kids swam. We did the 360 tilt experience, which I will say slight tourist trap. Definitely bought the$49 photo package. I won't be needing to share any of those, but I mean, whatever we do. Happy birthday, right? Back in the day, that used to be more of a rooftop bar situation, which I personally preferred. Um, actually went there on our baby moon and it's completely different now. But the family era, Chloe wanted to do that. She did that tilt experience where you're looking out on the 94th floor and they, you know, tilt you out a little bit. I did not do it. It's just not my thing. And of course, we went to the American Girl Doll store. And listen, I will ride that train as long as humanly possible. She loves it. She will still play with her doll. And I don't want that to stop. I love that. Because one day she will not want to go there anymore. And I am like not ready all the way for that stage of life. Saturday, we had a great dinner again, and we were in bed by 9 p.m., which is honestly the most mom version of a Chicago trip. I mean, we were up early though, I guess, in our defense. Also, the river was dyed green for St. Patrick's Day, which is really always fun to see. The kids got to see some interesting, you know, the some interesting people watching when you're down by the river and all the St. Patrick's Day festivities. But when I come back from a trip, I kind of like, you know, unpack and reflect a little bit. And this whole quick, you know, 48 hours in Chicago made me realize that Chicago has quietly been part of so many chapters of my life. You know, high school graduation, girls' weekends, my bachelorette party, friends' bachelorette parties, pregnancy, early motherhood, family trips, and now Chloe turning 10. Same city, different versions of me every time. And I think that's what I love about places like that. They grow with you. And I hope that you're thinking about a place like that too. I think that's the thing about certain places. It's never really just about the place. It's about, I mean, it is, but it's really about who you're with, the people you share it with, and who you were when you were there. And who you're becoming when you go back. Because even though Chicago has changed over the years, it didn't change drastically over the years, but I certainly did. And somehow that city's held space for every version of me anyway. You know, the girl who thought she had everything figured out, just 17, no it all. The one who was building a life and didn't even realize it yet. The version of me learning how to become a mom. And now the version of me watching my own daughter create her memories in the same place. And that just feels really special. It makes me a little nostalgia for, you know, like it makes me really miss my mom. Too, I loved a mom and daughter trip, but I'm gonna sidestep here really quick. They say the things you miss the most about the people who are gone. Be that person for the people that you love. And I'm just trying my best to be what my mom was to me, to Chloe. And those moments are just really special. Makes you realize how quickly life moves and how important it is to actually be in it while it's happening. Because one day, these are going to be the memories you look back on. The dinners, the walks, the little traditions you didn't even realize you were creating. You know, I will say when we were at dinner Saturday night, the girls led the conversation. What was your favorite part of this trip? And what was your least favorite? And what is the favorite thing that you got to eat? And I think maybe that's your reminder this week to go back to a place you love or to create something small that turns into a memory later. Because those in-between moments, they end up being the ones that mattered most. So I want to know, do you have a place like that? Is it Chicago? Is it another city? Is it your hometown city? It could be your hometown city that you live in and your favorite place to go on the weekend, somewhere that holds different versions of you. Message me always. I love hearing your stories, navigating between the lines. I always try to post the stuff that I talk about here so you can get a visual. And if this episode made you think of someone you've shared a trip with or a phase of life with, maybe it reminded you that you want to go back somewhere, send it to them. And I will see you guys next week, over and out.