As a former "fat kid," Lauren Herskovic had deep seated insecurities that led her to choose professional roles that didn’t give her what she needed because she didn’t think she deserved it. She spent seven years as the COO of a startup where the founders made her feel like she was good at her job and dangled the carrot of the “big payoff,” but it came with severely compromised boundaries. Ultimately, she found her way from soul-sucking burnout to success and authenticity in the real estate industry. Lauren’s story is a powerful testament to personal and professional growth that can inspire anyone facing their own transitions around the age of forty.

Guest Bio 

What do you get when you combine a teacher, a comedian and a COO? Either the start of a really bad joke or an attentive, knowledgeable, detail-oriented, and entertaining real estate agent. In this case, we’ve got the latter. Lauren Herskovic, founding member of Moda Group at Compass specializes in helping first time homebuyers find their place in Chicago.

Lauren grew up in suburban Detroit and now lives in Chicago. She got a BA in English and Secondary Education from the University of Michigan (Go Blue!). She then served as Editor in Chief for an online women’s magazine in NYC before working as COO for a consulting company based in Chicago, taking the company from a 3-person operation to a team of 100+ with offices in the US and China. If you think that sounds like something that would burn someone out, you'd be right! So, burnt to a crisp in the latter half of her 30's, Lauren decided to follow her heart and make the leap into Real Estate. And she hasn't looked back since. In her free time (which is limited these days, with this active market!) she eats her way through Chicago, binge-watches Bravo with her Toy Poodle, Harvey, and takes an obscene amount of pictures of said food and said poodle.

Turning 40 and Kicking the Soul Sucking Job to the Curb

In this episode of the Forty Drinks Podcast, Stephanie McLaughlin sits down with Lauren Herskovic, who navigated through significant life changes before her 40th birthday. Lauren shares her journey from grappling with self-doubt rooted in childhood to transforming into a confident real estate agent and finding love in a healthy relationship. Lauren paints a vivid picture of the ups and downs of personal growth, the importance of vulnerability, and the ongoing quest for self-acceptance.

Her story is a testament to the power of self-discovery and resilience through the midlife transition, offering listeners a candid look into the personal and professional growth that can occur during this pivotal time.

Episode Highlights:

Career Shifts: Lauren discusses her transition from feeling undervalued as a Chief Operating Officer in a startup to thriving as a real estate agent where she built her brand around her authentic self.

Self-Discovery: She reflects on her struggles with body image and how overcoming these helped her gain confidence in her personal and professional life.

Relationship Evolution: Lauren opens up about her past relationships and how meeting her current partner at the right time in her life made a significant difference.

Setting Boundaries: Learn how Lauren learned to prioritize her needs and set boundaries, especially concerning her time and personal space.

The Impact of Therapy: Lauren credits therapy with helping her understand herself better, which was crucial in her journey towards self-acceptance and improvement.

Family Dynamics and Personal Growth:She discusses the influence of her family's communication style on her personality and how external perspectives helped her gain insight into herself.

With a blend of vulnerability and humor, Lauren's journey through her midlife transition illustrates the challenges and triumphs of redefining oneself in adulthood. Her experiences with career changes, relationship dynamics, and personal growth underscore the universal quest for happiness and fulfillment that resonates with many in their forties. If you found this episode enlightening and inspiring, don't forget to rate, follow, and review the Forty Drinks Podcast. Your feedback helps us bring more stories like Lauren's to light! 

Guest Resources

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Do you have the Midlife Ick? 

Download Stephanie’s guide to the Ick to diagnose whether you or someone you love is suffering from this insidious midlife malaise. www.fortydrinks.com/ick  

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The Forty Drinks Podcast is produced and presented by Savoir Faire Marketing/Communications

Stephanie: Hey Lauren. Thanks for being here today.

Lauren: Thanks for having me. I'm so excited.

Stephanie: Me too. I love having conversations with people who are still somewhere in the midst of the midlife transition and you are 40 and will be 41 shortly.

I feel like when we first chatted and kind of got the, details of your story, I know you've been through a good part of transition, but I think there's still a little bit more to go for you. So I'm excited to get to you like right while you're in it.

Lauren: Yeah. I mean, I hope there's more. I hope this is not the end for me at 40, nearly 41.

So

Stephanie: That's not quite what I meant, but yes, you're that's not the end for you, I promise. A lot of my guests are older and, and so are able to sort of look back and, and see the whole transition. You know, they can see the beginning, the middle and the end, They can be sure that they're on the other side of it.

And so that's what I mean. You've got the beginning and middle of a couple of pieces and the beginning of another piece. And so, why don't we just jump in? Why don't you start by telling me what made you the person at the beginning of our story, which is like your early to mid thirties. So who were you as a kid, as a teen, as a twenties, like, tell me a little bit about that time of your life.

Lauren: So I look at the, at the core of it, I was always the fat kid. And I think it's something that has really, it sort of shapes who you are when that is who you are as a kid. It's sort of, at least for me and for people that I know who experienced the same thing, it's, there's always self doubt. There's always a lot of insecurity and I never really understood my potential or like who I was in the world, because that was always sort of shadowing. It was like always a shadow over me. Um, and like, it wasn't like I wasn't successful and I didn't have good friends, you know, I went to college and made this amazing group of friends and it's sort of, you know, I did have confidence that I was smart and capable, but I think I was always underselling myself.

And so I was ending up in roles and in relationships and in positions where I just wasn't getting what now I know I deserved, because I didn't think I deserved it. And so I didn't really have a linear career path. I didn't really know what I was doing. And I was just kind of picking up jobs where, you know, I was sort of bopping around a little bit. And I ended up in a job where they made me feel smart and they made me feel like I was good at my job and I was really, I thought, happy there. Um, but I was such a people pleaser you know, I just wanted more of that validation coming from work because I wasn't getting it in my personal life that I really devoted myself and gave them everything I had. Like I was working crazy hours. They were my first priority over my family, over my friends. And they made me believe that that was going to lead to big, great things and great success. But it ended up just crushing my soul and sucking it right out of me. And I just was really unhappy. But the one good thing that had come from that was that I realized that I am smart and that I am capable and that I'm really good at my job.

So at least I knew that if I was going to leave there, I could get my life back, but I could also, you know, take this risk, which I'm a very risk averse person and jump into a career where I was my own boss. And, um, so that's the one good thing that came from that, but I needed to sort of hit rock bottom and get a little confidence in order to do it.

Stephanie: Yeah. Yeah. So I want to back up two steps. I definitely want to talk about this job because there's a couple of pieces here that are really interesting, but before you got this job, you did some writing in New York in your twenties and you kind of, from what I remember, you said you, you didn't really know what you were going to do, but you came from a family where everybody went to law school. Is that right?

Lauren: My dad was a lawyer. My brothers are both lawyers. One of them married a lawyer. So, I had originally gone to school to become a teacher. It was what I had always wanted to do, but I just had a really challenging student teaching experience. And it just made me very nervous about pursuing that as a career. And so I was like, I'm just going to go to New York and try to be a writer. And I did that. And then I came back and I tried this and I tried that. And my dad was just like, sat me down. He had gone to college, gone to law school, was a lawyer for 45 years. So, he sat me down and was just like, you got to figure this out. Like why can't you be like your brothers and just go do this thing? You know? And I just think it was a generational thing. I think parents are now a little bit more open to watching theirchildren, you know, in their early twenties, explore a little bit, but I'm a millennial and I'm an older millennial, so that just wasn't quite. Like all my friends went from undergrad to either the career they're still in or graduate school, and then ended up in the career they're in. I just couldn't figure out my path.

Stephanie: Yeah. So how did that make you feel when your dad sat you down? Like, what, what was, what was that conversation like for you?

Lauren: Well, I went online and found statistics to share with him about how often people change careers in my generation. Um, but I get where he's coming from. You know, I I think, and it wasn't, I don't think he was saying it like yelling at me. I think he was just like, find something. And then when I did, because look, I that was a tough conversation to have, but at the same time, while they weren't supporting me financially, my parents did stand behind me when I said, I'm going to go move to New York and I'm going take my university of Michigan degree and work at a salon front desk, so I can try to like pursue this dream. And they were emotionally and morally supportive of that. So, I mean, it was a very dark year. I made no money, but, you know, I think that he just, he wanted what was best for me. And I think I just had a skillset that I couldn't quite place. I just didn't know where I could use it. And so I, and honestly where I am now, every job I've had has somehow given me skills that work, where I am today. So I don't regret that path that I took. It was hard, but I don't regret it.

Stephanie: I feel the exact same way about my career. I always, followed my nose and just kind of like, oh, there's an opportunity and there's an opportunity and there's an opportunity. And it wasn't, none of it made sense until you looked in the rear view mirror and then it was like, Oh, I got this, I got this, I got this, and now I can do this, so I, I completely relate to that.

Lauren: I like to think of it as like the thank you next song by Ariana Grande. Like, I had really traumatic experiences at all these jobs. They were like a lot of like misogynistic bosses and all these things, but it was like, like, even the last one, which was really very traumatic and I really just lost myself in it.

I still think that the skills that I, I'm grateful to have had it because I'm so much better at the job I have now because of it.

Stephanie: Right, right, right. You said something earlier though, and I'm trying to see if there's a path through to the core of this. You said something about being a people pleaser and then you said, your dad's sort of sat you down and said, pick a lane. And so I'm wondering if you have any idea where that people pleasing comes from or where you picked it up along the way or.

Lauren: I had a really good childhood. So I don't want anyone to think that I'm saying it was rough by any means. I grew up upper middle class in the Midwest. I had, my parents were still married till the day my dad passed away. Everything was good, but from what, where I was sitting and what I knew was, we were a yelling family.

It was a volatile. My mom yelled at my brothers. I had twin older brothers. We were, you know, we, we all get along great everything, but like I was the third child. So I was always just trying to keep the peace at home where I was just like, Oh, you know, like when I was really young, I was probably fighting all the time. But as I got older, I was just like, I just wanted everybody, I wanted to help like work us through whatever we were fighting about. And I would just kind of be like, all right, fine. I'm out. I don't. You know, and I do that now too. If I'm on vacation with friends and there's two bedrooms and a couch, like I'll be like, I'll take the couch. You know, I just like, I will for everyone else to, so that is sort of where it came from.I was the baby and I was five years younger than my brothers and so it was just like, trying to just keep the peace in my household.

Stephanie: Yeah, and that's so interesting that you point that out, because that's one of the things that I am learning through these conversations and through this, interest area that I'm investigating is that, you know, you can have a great childhood. I also come from middle class, two parent family, practically the picket fence, three of us and a dog.

And, you know, mom stayed home with us until my littlest brother was in, first grade, and then she went back to college. I mean, all the things. But you can be from that picture perfect family and still have things that, affected you and that, that, that didn't fit you just right. That didn't fit your needs just right. Because it was more than you, right? There was a whole family system that was, that was working around you. So,

Lauren: And you don't know, that that's not normal. You know it's like, my now partner, my boyfriend, he comes from a family of social workers. And so they always talked about their feelings. And I honestly didn't know until I brought him home to meet my family, how weird it is where he's like, are you not going to go hug your brother goodbye. And I'm like, ew, no. Like we are not a hugging family, you know? So you just don't realize the way that your family impacts you until someone looks in and tells you, whether it's a therapist or friends or whatever, you need those points of reference to understand who you are in the world. I

Stephanie: That is such a riot, Lauren, because my husband is also a social worker and his dad was a social worker and his mom and his sister are nurses. So I always say like, he is the most emotionally intelligent person I have ever met in my life. it's funny to like leave a family event and have him be like, Whoa, like, what was that?

Lauren: know he's like, should I hug your brother? And I'm like, ew, don't make it weird. Like, please don't.

Stephanie: Yes. Yes. I agree with you. There's definitely that context of, and, and you can't really do it when you're young, even, you know, when you have friends and you're little and you're, you know, in middle school or high school or even college, it's like everything is just, it's your family and then foreign. Right.

Even though you might be like, Oh, you know, I like those people or whatever, but your family is still sort of the system that, that you come from. And so everything else is just foreign, but it's not until I found later that, context comes in through, through other people in your life.

I had a girlfriend a million years ago who was like, I am going to get you to tell me that you love me. And I'm just going to tell you that I love you until you're comfortable saying it. Like she was like in my face and, and she finally did. She finally broke the dam. But again, that was like, my family was not like vocal that way. We didn't, we didn't talk that way. So it was very uncomfortable for me. It's still sometimes is.

So, and that I feel like turning 40, all these things happened all at once. Like I really start to get myself and all these things, but maybe these new generations are tapping into it a little bit earlier. And so maybe they will know who they are a little bit younger than we did in my generation.

Stephanie: Yeah. Yeah. And mine for sure. I mean, Jeepers, I didn't, I don't think I did my first therapy until I was like, I mean, just after my dad died, how old was I then? 44, 45. I mean like, yeah, it's, yeah, it's, it's crazy. But it's so interesting too. So one of the sort of, backbone theories of this, of this whole, turning 40 transition is that part of this transition, you go from what has been called first adulthood to second adulthood. And in first adulthood, that's where you rely on external authorities. So it could be our parents, our teachers, our mentors, our bosses, whoever, to advise us on the things that are going to make us happy, healthy, successful, safe, right? And so you just said it about your dad. You know, he wanted the best for me, right? So he was pointing me in the direction that, in his mind, in his generation, in his context, made the most sense. And so part of this transition at midlife is about finally starting to realize, I am the authority on my own life and my own needs and my own wants. And you start taking responsibility for your decisions and you stop placing so much weight in the opinions of those external authorities, because now you have your own experience, your own expertise, your own ideas. And, to your point, and we'll get to this in your story, kind of like, come what may, this is the, this is the decision I'm making. I'm taking a leap of faith and don't care what, dad or bosses or friends or, mentors or anybody else says.

Lauren: Yeah, and I think it's also just like this comfort level with who you are. And for me, at least, it's like, I finally know who I am. And maybe it's because I went from having bosses and sort of on just like the world of people telling me what to wake up and do every day to making all these decisions for myself. But I just feel like so much more confident. And I think it also is age. Like I think if I got into this business in my twenties and I didn't know who I was, it would have, you know, I'm a real estate agent. So, uh, getting into this industry in my twenties with who I was in my twenties, this would have chewed me up and spit me out very, very quickly.

But it's like this combination of like I'm old enough. I feel wise enough. I feel confident enough. And then seeing success, not immediately, but pretty quickly, I was just like, Oh my God. I never felt better about myself in my life. And I think a lot of that really came to fruition right as I was like, there was something in my mind. I was so excited about turning 40. I was like, my thirties were so good, once I figured out my life. Now I'm going to enter this new decade in the place that I'm supposed to be. And I'm just so excited for what's going to come and then believe firmly, and I think a lot of people do that, like the energy, I was so sad and depressed and just not in a good place in my old career that the minute I switched and I'm now in a better place, like I'm putting out a better energy, which is why I think so much more good stuff is coming my way now.

Stephanie: Oh yeah. I, and I have the exact same experience in my thirties as well, but let's jump back a little bit. So this job that you were in, it was a very small company, right? And then you ultimately ended up as what was your title when you were there?

Lauren: Chief operating officer. So it was me and the two founders.

Stephanie: Yeah. Yeah. And they gave you a lot of responsibility. But at the same time, you said you had a hard time drawing boundaries.

Lauren: Yeah. I think everything's shifted in the past 10 years, but you know, when you join a startup, it's always like everybody does everything and it's all hands on deck. We are building something bigger than ourselves here. And, on top of that, they were just showering me with praise for the work that I was doing. And I was craving that, you know, I've always said, like, I never felt really confident in my personal life because my dating life was terrible. So it was like, all the validation I could get was coming from work. And so I would just do whatever I could to continue to get that.

It was an international business. We had, clients around the world and then we ultimately built offices in China. So while I was running the U S operations all day, as soon as I would finish with that, the Chinese operations would open. And so there was just never off time. I would work really late at night because I was trying to prevent the number of emails that I would wake up to in the morning. And it was just constant. And, you know, I think that it was really hard to create boundaries. We, I would hit a wall. I would go to my bosses and I would say, I can't do this anymore. And they'd be like, well, then work less, like you have to create your own boundaries. But then at the same time, they were giving me more. And so I was just like, how, you know, and so I think in their minds, they were just like, well, we told her not to work so hard. This is just what she wants to do. But like, they weren't really giving me the opportunity to work less. And I do think a lot of that was on me and like, I'm older and wiser now, and I'm creating my own boundaries for myself as much as I can.

I just wasn't able to there. And I wasn't it wasn't an atmosphere that allowed for it. Um, and I thought I was happy. Like I was working from home. I really liked the people I was working with. I liked the wins as the company grew. But then I realized that like when you're working from home all the time and your hours are very fluid, you don't end up leaving.

So I wasn't seeing my friends. So I would go home and I would spend time with my family, but I'd be working the whole time I was home. I'd be on vacation. I'd be working. And then as my relationship with my partner started to fall apart, I was just like, what are you doing? Like nothing is, this isn't making you feel good and you're definitely not being compensated for it.

Stephanie: Right. Right. And you said to me something about, sort of the grind. Tell me, like, when you're, young and,you've got one of these great jobs and you're just grinding, grinding, grinding. I think you, you told me earlier that that was something you, you felt like that was just part of paying your dues or that was like, that was what you did to get to the next step. Right?

Lauren: Yeah. And I think grind culture and like hustle culture, all of these things have really shifted since COVID, but at the time it was like startups, you know, this was what? 20 11? I think I joined that company. So like it was grind culture everywhere. You know, it's like, and I went to college with a bunch of friends who then went on to either work in investment banking or work in tech or work in really big law firm. So everybody was grinding. And then it sort of gets into your head that like, you want to feel needed at work. You want to feel important. And so those things go hand in hand. And it's just like, you feel like you have to work really hard to get to the next level and then it will pay off in the long run.

Like at this company, it was like, the goal was, I thought, let's build it and sell it. And then I'll take that money and then I'll go do my next thing. And it just felt like, because my partners and my bosses, they were all doing this much work too, at least in the beginning. At the end, I felt a little bit it was uneven, but I was just like, everybody's doing it. Like, this is just, we're part of something here. And you just, put your own, like, health and mental health and everything on the back burner, cause you think this is what you have to do. And you also think it's a finite amount of time, but it was turning out to be infinite. So yeah.

Stephanie: So how'd you finally get to, the point where you were going to make a decision to exit this? Where were you when you've said enough?

Lauren: You know, it was the same thing when you're in a bad relationship and your friends are like, you're making excuses for the person you're with. And I was just like, no, like they do appreciate me. They do value me. And my friends were like, if they valued you, they'd pay you more. Like, they're just not paying you enough for what you're doing.

And so I went, like relationships had already started. We are we are all in a kind of bad place at this point. Like, technically I was a partner in the company, but they were still my bosses. Like I was an equity partner. Um, And I said, for the work that I'm doing, I need to get paid more.This is not sustainable. He basically was just like, no, I, you know, I can't, we're not paying you more. And it would thing was, it was like, I was an equity partner, like a shareholder, but they were the ones determining how the money was being spent. And they were the ones determining when the money would be pulled out of the company and distributed.

So like, that was, that was nothing. At that point I was, so dismayed that I was like, I, think that you made me that just to pay me less with this promise and this carrot. And so he said, no, we're not going to pay you more. And then I was just like, all right, this now it's my turn to go do what I need to do for myself.

So I. I had worked my butt off for so long and then I was like, I'm going to get my real estate license and I'm going to use my time of getting paid a salary to study for my real estate licensing exam. So I phoned it in at work and I'm not proud of that, but I also feel like I paid my dues and I don't really care.

It was also not our busy season. Um, and I got licensed and then I just started setting up. I finally knew who I was and knew what I was good at. So I, I was, I knew that if I was going to go into real estate, I didn't want to just be an agent and not know what I was doing. So I sought out relationships with people to learn from, to be mentored by, um, to, to carve out a little bit of a salary as I transitioned. And I made the transition myself. And in doing so, I completely burned a bridge with one of my former bosses. He will no longer speak to me because, I made a decision that benefited me that he did not like, and I lost relationship with both of them, which, if you would ask me six months prior to that, if I got married, who would be standing up in my wedding, that probably would have been the two of them. And that was like a really big lesson to me where it's like, work is work. At the end of the day, your relationships with people you work with is purely about work and like, yes, you can have good friendships that come out of work. But first and foremost, like I was making decisions to make their lives better. And that was the moment where I was like, I can't believe you just did that for seven years. Like they actually don't care about you the way that you care about them.

Stephanie: Wow. Oh, that's gotta be a punch in the gut.

Lauren: It was hard. I mean, I doubled up on therapy for a while. And you know, I, uh, but I realized like, six months later, like I transitioned, I got into real estate. I found my place. I, I now I had these boundaries with the people I worked with based on my experience. And I have never looked back once, not even like day one. I've never looked back. Cause I just know that this was where I should be.

Yeah,

Stephanie: Let's, dig into that a moment because you have told me, I was looking through my notes from our first conversation. And in like two or three places, it's like, I'm risk averse. I'm risk averse. I'm risk averse. Let me just toss out this, this great job, that's stable and reliable, dependable. And let me just like jump out of a nest.

I know you said you studied for the real estate license while you still had a paycheck, which is great. But tell me, like, How did you find the courage to walk away from something

Lauren: I think it was less about courage. It was like this job was not going to work anymore. And I first tried just like applying for regular jobs, but I just I'd never worked at like a real company. I'd always worked at small startups. So I just didn't even know how to apply for a job. And I always say like the two most demoralizing things you can do in your life are apply for jobs and go on dating apps because they both just make you feel so bad about yourself.

Because I was like, I have a great education. I was the COO of a company, and I know that I'm not going to get hired at Google as a COO, but I was like, I should be able to go in somewhere and use this. I built a company, like I basically had an MBA at the end of it. Um, and it just like, wasn't translating.

So I was like, know what? I guess I have no choice but to try this thing that I've been wanting to do. You know, real estate, you make no money until you sell a home. I couldn't go from having like a nice salary to having no money. So I went to the real estate agent that had sold me my house. And I said, you were very disorganized when I met you. Like, why don't you let me be your operations person? I'll build your systems. You pay me a salary. I know it's not going to be what I used to make, but it'll be something. And you mentor me. So for me, that was less risky because I was learning. And I was getting paid. And I was getting health insurance. And so like It seemed a little less scary.

Um, And it was more of a step down than just like a slide into real estate. And so that I think I knew myself well enough to know that that was what I needed to make a transition.

Stephanie: Yeah. That's, that's really thoughtful. So as that period where you're being somebody's assistant is sort of coming to an end and you're being mentored, tell me about the, your real estate career journey, like,

Lauren: Yeah. I think I'm very grateful that I got into this industry when I did. One, it was before COVID. So that was great. Um, but two, I was just like, I was older. I had had a lot of career success. So like, when you first get into this industry, the people that you work with are the people that you know, for the most part.

So even though I had never sold a house before, being partnered with someone who had a lot of experience, gave me a little bit of clout, but also my friends knew that I was smart and capable. And if I felt like I was good at something, they trusted that I was good at it. So I had like a transference of, uh, confidence coming from people around me.

Um, but also I just, I was not too proud to do whatever you had to do to be successful. Like to go from being a COO to being someone's assistant, a lot of people aren't going to do because of pride. I was just like, I will kiss anybody's feet who will teach me something or give me a skill or something. And I just worked, you know, having come from a world where I was working like insane hours, I was just like, okay, I'm going to keep working insane hours because at least now I'm the only person benefiting from my work and, you know, this is not an easy. This is a very difficult career.

I thought. No matter what you could have told me before I came in, I'd be like, I got it. Don't worry about it. It's way harder than I ever thought it was, but,this is where I belong. Like it's rewarding. I love the work I do. I feel burnt out right now, but I'm like very grateful to be busy.

And so I was just very fortunate. And I think a lot of it is just like, there's no straight path in real estate. There's no barrier to entry, but like, there's no, way to compare yourself against anybody else because people come into this career at different times in their lives with different connections, whatever.

Stephanie: Mm hmm.

Lauren: Knowing who I was and knowing what I was good at and knowing that generally people kind of like me, I'm just going to lean into who I am, and it's going to work or it's not, but I'm not, I'm too old to just try to be someone else. And it worked. I was, successful pretty quick out of the gates. After that one, I did a year as an assistant. And then the minute I snapped into being an agent, um, I saw success pretty quickly, because I had taken everything I learned from that year and applied it.

Stephanie: That's amazing.

Intermission

Stephanie: So you swapped careers, you were 35. So again, like right on time for this midlife transition, like

Lauren: Not a crisis. A transition.

Stephanie: A transition. Yeah, no, no, not everything's a crisis. I mean, mine was a crisis. I, I was not smart enough to see the signs on the wall. And actually that's a theme I'm picking up in my own life. There were. plenty of times where I've stayed too long in both relationships and at jobs. You are not alone. I know, I know,Um, my last, full time job, I got walked to the door by the HR lady with my purse on my shoulder. So, um, I was 36 and I, I started working with a career coach and then ended up going out on my own.

Yeah. And that was 17 years ago. And my business now is like, it's the best thing. Cause it's built exactly to suit me and my team. But one of the things I want to know is you said that you had taken so much of your self worth from your job, previously. Tell me about how that translated into this real estate career.

Cause of course, you know, you're going to the bottom of the pile again, and then you're working your way back up. But you also said something just a moment ago where you said, I just leaned into being myself. How was that different than what you had done before?

Lauren: I am my own brand now, which is like kind of weird to say, but you know, it's like when I first got into real estate, I was like following all these big agents on social being like, Oh, what do they do? I should do that. And I should do this. And then I was realizing like the things that were working the best for me were just like me being me. Um, and it did take a minute to figure that out because even if you're a really confident person, at least in my experience, like if you go into a new world, of course, you're going to feel like bit of an outsider looking in.

But I just feel like, I don't know, like, I knew I, I came in with a level of confidence that I was like a very hardworking person and that I know that I like as the former fat kid, humor was always my strongest attribute. So I was like, I'm just gonna,be who I am and people are going to work with me if they want to work with me And they're not, if they're not, and I still am a people pleaser. I like to think somebody once said something that has stuck with me. And he said, making people happy makes me happy. And that is sort of the way that I approach my job. It's the way I approach my life. It's a little bit more of a positive spin on being a people pleaser, you know, but I'm still going out of my way and doing things for other people before myself when it comes to work. And I'm still taking my job very personally, and I feel a lot of validation coming from it, but it's more because this is something that I built for myself and, and I'm doing this on, you know, I'm on a team. I have an amazing mentor.

I'm so fortunate. I'm at this amazing company surrounded by really inspiring people, but at the end of the day, like when my client is happy with the work that I've done, it's because of the work that I've done. And I know that I put my all into it. And so I just feel really good knowing that like someone else is benefiting from what I'm doing, especially on a scale that's so large. Like this is a huge moment in people's lives. And I feel so, I think that's why I'm so happy. People are so happy because of what I'm doing. And it makes me feel good.

Stephanie: Yeah. Yeah. Yeah. That's got to be really validating for sure. For sure. That's great feedback. And I love what you said about, making people happy makes me happy because it's like, it's, it goes back to the old, you know, are you the tiger wagging the tail or are you the tail being wagged by the tiger?

And it's a way to sort of put a little bit more intention into taking a trait that can be problematic, can take over, can be negative and, and putting some intention around it and saying, sure, no, this is who I am at that point. You're the tiger, right? And, and the tail you're, you're the one wagging the tail.

Yeah.

Lauren: That's really a really good point because I remember talking to a coach and she was like, well, I wouldn't say people pleaser because that's not necessarily the best quality. But I'm like, how else do I say it? Because that is what I am. Like, I, I want my friends to be happy. If I'm planning a trip, I think about what everyone else wants to do.

And I'll just, I'm happy with everything. And so it really is who I am. It's just, I don't think it's always a bad thing. I think it can be. But I think if you find the right path in your life and the right people around you, it's a good thing.

Stephanie: Sure. But tell me what you do to make yourself happy first.

Lauren: I watch a lot of TV.

Stephanie: Girl after my own heart. I do too.

Lauren: I think what I have learned in my last couple of years, which, right around 40 is when I started to feel really comfortable in it, is I am much better about saying no to things that I don't want to do anymore and saying yes to the things that I do. And of course, I'm still going to consider other people's feelings, but for example, It's the most ridiculous thing, but like, I've been so busy with work that I haven't been able to watch my shows, but my shows, I watch a lot of Bravo. I surround myself a lot of people who watch a lot of Bravo. It's a big part of our conversations. I want to be a part of those conversations. And last weekend, my boyfriend and I went to Las Vegas. Normally, he would download things on his iPad we watch together.

Stephanie: Mm hmm.

Lauren: And I know that that brings him joy. But I was like, I need to watch my stuff. And I know that you don't want to watch what I'm watching, but I need this for my own, like my, I need to turn my brain off after a long week of work. And, you know, normally I would just do whatever, cause I want to make him happy. But I was like, I got to do this for me. And like, even when we were in Las Vegas, there was a morning and I was like, I'm going to lay in bed for two hours. I'm just going to watch my shows. And you go do whatever you want. But like. This is vacation isbut it's also, I need to come down in the way that I need to come down because work's been so busy. And like, I used to say yes to dinners with people just cause I felt bad that I hadn't seen them in a while. And now I'm just like, this time right now is sacred to me. I get so little, little time to myself, whether it's to work out or it's to meditate, which let's be honest, I don't really do. Um, or even just like, from like eight to 10 PM at night. Sometimes I just want to clean out my inbox just so I feel good going to bed. So I'm much better about doing those things and recognizing what I need and then doing it for myself.

Stephanie: You touched on something very interesting that I'm not even sure that has come up specifically in any of my conversations yet but it's something that I relate to very much. As you have gotten older, probably just in the last couple of years, do you find yourself interested in spending more time by yourself than you had been previously?

Lauren: I was single for so long and I do have like a full social life. I'm very fortunate. I have a lot of friends from a lot of different periods of my life. Um, But I've always been very good at being by myself and like during COVID, I was like thriving. I just I'm okay on my own.

But now that my job requires me to be on so much, and you know, I'm juggling being on at work, but also maintaining my personal relationships. And now I have a new romantic relationship, which I'm not used to having. So it's just another person that I'm - I wouldn't say owe my time to, but just another person I have to fit in. I do treasure my alone time a little bit more just because it is so much more limited. Like I was never, I was always okay being alone. Now I'm just like, I really take like so much joy in it because the time I get to be alone is so short now.

Stephanie: Yeah. Yeah. Okay. All right. That's interesting. Yeah, I, I definitely have found myself being more comfortable with being alone as I've gotten older, certainly through my forties, but now into my fifties, then I had been in my twenties and thirties. It was very much like, um, you know, this party and then that thing and then that event and then that, and then out for drinks after the event and like, you know, and I was going from like 8am to 10pm four or five days a week and then, you know, sleep in on the weekends and then go out like a, like a crazy person to, you know, two nights on the weekend.

Lauren: I think that's part of being in your twenties and early thirties. But I wonder if people of that age now go as hard as we used to go now that they are coming out of COVID. Cause I think COVID forced us all to realize that's not what we wanted. Um, but also I'm an extrovert. I was going to ask you what you consider yourself. I'm an extrovert, but I still need that recharge time by myself. Like I get energy from being out in the world, but I need that time where it's like, I'm literally just like, I'd call it powering down. Like I just need to turn off the switch for a second.

Stephanie: Yeah, I'm definitely an extrovert. Years ago when I was with that career coach, it was, it was like a nearly like, you know, not off the charts, but right at the edge of the chart extrovert. Pinned the needle. But I think, as, as time has gone on, so I was about 36 when I was doing that kind of stuff. So it's been, you know, 15, 17 years. I don't know if I've come a little bit more in balance. I definitely have found that, I never before needed come down time, but now I do. I think it's also part of it is having my husband and being so fulfilled with the time that we spend together that I don't feel necessary to go and do all of these, you know, everything's with all the friend acquaintances, I call them, right?

Sure, you're friends, but, you know, we see each other a couple times a year. So we're not close friends, right? I don't feel the need to fill my time with all of that. But here's the other interesting thing that I think has transitioned for me. We just got back from vacation, as I mentioned to you earlier, and we had dinner with, um, my cousin and his wife and her sister, the last night before we flew home.

And somehow the introvert extrovert thing came up and, and I was saying, for all my life, it's been like,I'm a Leo. I'm an extrovert. Give me some spotlight. I love it. Big crowds. It's great. But these days I find very much that I'm still extroverted, but I want a much smaller group, like there were what the four or five of us in that group. And we sat and talked for five hours straight. And for me, that was like, Oh my God. Cause I'm from a huge family. And so we were kind of sort of comparing and contrasting with, you know, events at, at the family house. And it's like, well, sure. I get three minutes with that person and eight minutes with that person. And you're always like passing by someone and there's never anything like real or true or deep. And so, so

Lauren: Could not agree more. Cause I have friends and I love them, but they're, they're includers. Like if they're going to go do something, they invite literally everybody. And I love that about them. Cause I feel like, thank you for including me. But for me, I would rather have dinner with four people where I can have meaningful conversations with all of them because otherwise I feel stressed that I am not seeing and communicating with everybody. And I feel like exhausted when I leave and like nothing actually happened. So and I do agree with you. I think that has happened more as I've gotten older because, I have a lot of distinct groups from a lot of different times in my life. Like I've got my work friends and I've got my college friends, my high school friends. I have friends who like love to put them all together. And I, in theory, I love that, but I feel very stressed about making sure everybody's mingling. So I just like to keep it like a salad bar where everything is kind of like in its own separate bowls.

Stephanie: Yeah. yeah. And you can enjoy each one on its own. Yeah. So that's, that's been an interesting twist for me, recently. And it's funny too, because this, this same cousin, he lives in Los Angeles, he and his wife and kids, and, we're very close to the same age. He grew up in Virginia, so he didn't grow up locally. So, he and his brother would come up, when they were kids, for a week in the summer, but you know, we see them when they come for a visit once every year or two. And again, it's in that, environment where there's 40 or 50 people in the room. And so I can't get a chance to spend much time with him or his wife because all my aunts and uncles are like, you know, they, they like quote unquote outrank. Right. So like, he's got to spend his time like with them. And yet the last couple of years, we've gone to Los Angeles a couple of times. We actually stayed with them the last time we were there. So we had like a couple of days with them. And then this, like, I feel like we're like super tight now. And this

Lauren: Right. You're establishing an actual relationship for the first time ever.

Stephanie: Yes. yes, yes. It's, it's like been so amazing for me. And, and I think for them too, yeah, so it's funny, cause it's like, yeah, super extroverted. Like I want to like sit and talk with them for five hours. but at the same

Lauren: You know, and I have this, I have a similar situation because I live in Chicago. My family's in Michigan, and I have a lot of friends who are in Michigan still. And I used to go home and I would be like, all right, so Wednesday, I'm going to see Maggie and Thursday, I'm going to see this person and Friday, I'm going to see this person. And then as I got older, I was like, I want to go home and just like lay on the couch with my mom and watch TV. Or I just, you know, it's like my family, my brothers were having kids. I wanted to spend more time with their kids. And then my dad passed away almost two years ago. And now it's just like, I just want to go home and be with my family. Like, I don't even like, maybe I'll see one person, but like, there are people there that I love and have been in my life for a very long time, but like. Like you said, they're friend acquaintances at this point, and I need to draw the line somewhere to maintain the relationships are the most important. And I think it took a lot longer in my life for me to realize, like, you know, it's not you.If my friend's at home that I don't see anymore, if we're not seeing each other all the time, it's not just me. It's not my, it's not like I have to blame myself. Like we drifted And that's totally fine.

Stephanie: And P. S. they could come to Chicago whenever they wanted. If they really felt like they wanted

Lauren: And when they do,

Stephanie: with you.

Lauren: These are the kinds of relationships you want where it's like, they're good. When you see people, you snap right back into it and you feel good about it, but you don't need to feel obligated and guilty for not seeing them all the time.

Stephanie: Yeah. Which is just, again, another one of these interesting shifts. When you're younger, I know for me, it was like, everybody was the same importance. And now there are, there's, you know, the, the peaks and valleys are like, no, people, people sort of, you know, weigh differently. A little, you know, a little bit.

Lauren: Yeah, for sure.

Stephanie: Um, all right. So one last thing I want to talk to you about. You've mentioned it a couple of times. So you switched jobs. You went into real estate. Your career took off. You had great energy. You were attracting really good things into your life. And then, bum, bum, bum, tell me about the dude.

Lauren: You know, it's very strange. My whole life I've only ever really had two serious relationships. And I think part of it, I blamed myself cause I was insecure, but also I was just like, I don't know. Like I think that I had so many good people around me that like, maybe I was like, maybe your standards are too high. Like maybe what you want doesn't exist. But I also kind of came to terms with it and was like, you might just be one of those people who does not find a partner and that's okay. You've got a great job. You love your life. And I also have a lot of friends who are still single, even though we're all in our forties. And soI never really felt pressure. My brothers between them have six kids. My parents are happy and fine with the grandkid count.And the older I got, the more I realized I didn't necessarily want kids because like, I've gotten used to this life without them. So I was still dating you know, was still interested in trying to find it, but I was just, it is what it is. And I was dating terrible men. Terrible, terrible men. Um, And then I did an especially awful one who manipulated me and was just really terrible. And it ended in a, in spectacular fashion. And I think I had to hit that rock bottom because the next person who came along, I'm tall, I'm five 10. Um, And because I was a bigger kid growing up, it was always very important to me to date someone who was taller than me because it made me feel smaller.

Um, and I, yeah, and we all have our thing. That was my thing. It doesn't, I don't care what the person looks like. If we connect on an emotional level, I'm good. It just didn't, just needed to be taller than me. Um,

Stephanie: You just needed to be able to look up.

Lauren: yeah, I just didn't want to feel big, you

Stephanie: Yeah. No, I I'm 5'9 and also never been a skinny person. So I 100 percent can relate to all of it.

Lauren: Right. And one of my brothers, who I always thought was an idiot. He was just like, you have to get over that. And I was like, David, like, don't tell me what I have to do. Like I've dated across the gamut. Like this is my thing. And after dating this awful man, I connected on an app with this new guy. He was shorter than me, which I was just like, all right, you got to get over this. Cause we can, we just had such good conversation.

Again, I come from a family that doesn't talk about our emotions. And I think my history, which I'm now realizing is, I need people to pull away from mein a relationship for me to feel, um, that. Because as the men I was dating, were always just like, avoid it. And then I, it would pull me in. This person was like super communicative, but always tell me about his feelings. And I was just, if I hadn't had that really bad relationship before, that would have turned me off immediately. Cause I'd be like, Whoa, boy, chill. But I was like, you know what, maybe we should just see this through because he was just incredibly kind and funny and smart. And those are the things that matter the most to me. Um, And I just in a good place where I feel really good about myself. So the height thing did trip me up for a little while in the beginning. Um, but I'm just like, whatever. I don't care anymore. But we've been together for six months.

It's really, it's like the healthiest relationship I've ever been in. And, he is getting me to talk about my feelings, which is not easy. Ask my therapist. She just has tried for years, but I just feel like he is the right person, but I think he came out at the right time. Like if we had met at a different time in our lives, I don't know that this would work for either of us.

It wasn't like I wasn't looking, it's just like I was looking in the wrong place. If I had met this man in my twenties, the person I was in my twenties is not who I am now. And I'm very grateful looking back that I had all that time to figure out what I wanted to do on my own. To move to Chicago, buy, my first home, sell it, buy my second home. I got to do all this by myself and really figure out who I am and get to be comfortable with who I am. And then I found the person that is right for me. And this is who I am now. It's in, and I'm sure I'll evolve over time, but I think I'm going to change a whole lot less and explore a whole lot less from 40 on than I did from 20 to 40. And I think the 20 to 40 timeframe was really important for me to figure out who I am.

Stephanie: Yeah, yeah, it's important for everybody to figure out who they are. And for some of us, it takes a lot longer. And for others, they come to it sooner. And I, and I do think you said something earlier about generationally, you know, maybe the, the, the generations that are behind us will do a better job. And so won't have as much pain and suffering through this midlife transition as, as I did, as, as you did, as, as other people, you

Lauren: I theirs is going to be different, but I think we all have to have it. It's we're growing at that point so much.

Stephanie: Yeah. And I mean, and that's exactly the thing is that this is a developmental stage of adulthood. So,even if you're doing great through your twenties and thirties. One of my one of my more recent, conversations with, Stephanie Rose, she, she really did a great job of, finding herself and doing her things, but then, she got married, had a kid, bought a house. Her mom died. She had another kid. For her, it was identity, right? It wasn't things coming crashing down or or having to hit rock bottoms. It was it was no, she was doing all these good things that did align with who she was. But her identity kept shifting. And so then she felt like she really needed to dig in and, and, and think about those things. So, for some people there is crashing. There are rock bottoms. For other people. It's, it's just evolution and, and transition into the next stage of themselves and, you know, again,

Lauren: but everybody

Stephanie: Yeah.

Yeah,

Lauren: And everybody has it. It just totally looks different on all of us. You know, My boyfriend, he got married, right out of college, and obviously he's no longer married. I would like to state that for record, but it's like, that was his transition. You know, like they grew apart. And they are very close and they have a very healthy relationship now, but like they didn't know who they were when they got married and they didn't know what they both needed from a partnership.

And so like watching that happen, like my brother married his high school sweetheart. They're perfectly happy. They've got two kids that worked for them. They grew up together, but. Who I was in my twenties, I know that whoever I was with, I would have just done whatever that person wanted. And I wouldn't have grown with them. I would have stifled myself. So for who I am, this path was better.

Stephanie: Yes, me too. I feel the exact same way. By the time I met Patrick, I was 40. And I did finally realize that the common denominator in all of those terrible romantic relationships was me. So when he came along, I literally said to myself, I am going to do the opposite of what I normally do. If I want to call him, I'm not going to call him. If I want to text him, I'm not going to text him. I'm just gonna, I'm just going to do the opposite. it kind of, it, it worked for

Lauren: Well, yeah, I also think it's us, but like, I know that the withholding is what makes me crazy. And so when I'm finally dating somebody who every morning wakes up and just says, Hi, I'm thinking about you. And I don't need to feel crazy. Cause I know someone's That he, that I'm not the, it's not a one sided thing that I'm like, Oh, it's not, it wasn't you. It was, you're bad at picking the right people. That's what we did wrong.

Stephanie: yes, yes, for sure. And picking people who also were broken in ways that, that we, not only can we not fix, but that triggered us. That, that triggered us in, in, in ways or triggered behaviors or patterns or, yeah, yeah, it's, but that's actually one of the wonderful things of sort of coming out into this part of life is that you do have a better sense of who you are and what you want and what you'll stand for and what you won't and, and, and things get easier a little bit, don't you think?

Lauren: Yeah. I just feel, I hope that I maintain this feeling 40s and beyond, but I just feel content, like I'm not comparing myself to people anymore. I don't, I'll have a little FOMO sometimes, you know, I'm, I'm learning to realize I can't be everywhere all the time, but I just, I'm happy and I'm content. And like, if this is where everything stays, I'm good. You know.

Stephanie: Yeah.

Lauren: I don't think I felt content for like 39 years, so this is good.

Stephanie: Right. Right. Yeah. I, I have that same thing as well. It was about the time I, I, I met my husband and very similar things with him. Like he was very, forthcoming. I never had to worry. I always knew where I stood and wherever I stood was always very good. and there is a, a, a piece of like anxiety that just kind of like goes away. Like you don't have, like, you don't have to worry anymore. It's good. It's

Lauren: I know. And it's a very weird feeling where it's

Stephanie: It is.

Lauren: Like my boyfriend is currently sick. I haven't seen him in five days, but like, I know he's there. It's like, I don't have to worry that anything's going on. Like, I just, I it's weird. It's like, upsets me to think that I expected or that I accepted less than this before. But I think every person deals with that.

Stephanie: Yeah. Yeah. In some part of their life. For some of us, it's romantic. For others, it's,

Lauren: Yeah. Friendship, family, whatever. We all have that where we accept less than what we deserve.

Stephanie: yeah, yeah, well, I'm glad that you have, identified that and, and are, are no longer doing it. I mean, that's, that's so great. So I love that, you know, usually the last part of one of these conversations is like, well, where are you now?

And like, how does it feel looking back on the transition? But I think you're still kind of in it a little bit, don't you?

Lauren: I do. I think, especially cause this is such a big life change for me is is having a partner and, and, you know, the potential that this could be it, I think I am struggling with balancing everything right now.

Stephanie: Mm hmm.

Lauren: So, but also like, I'm still new ish in my career. I don't know where this is going to go. There's so many directions it can go in and, there's so much coming and it's just really exciting.

So I'm, I am excited. One of the reasons I wanted to do this is because I want to be able to have something to look back on in five years just to be like, Oh, where are you now? And how are you feeling now? And it's going to be fun.

Stephanie: Yeah. Yeah. Well, if everything goes well and I'm still doing this, will you come back in five years and tell me how you did?

Lauren: Oh yeah. Who knows what my hair is going to look like? It's, it's been changing so much in the past 10 years. This will be fun.

Stephanie: All right. Great. Great. Well, we'll look forward to that.

Lauren, thank you so much for joining me today and sharing so much of your story. I just, I really appreciate it and, um, I'm glad to have had you here on the podcast.

Lauren: I love what you're doing. I think it makes people really stop and think. So I hope, I hope there's some 21 year old person out there somewhere who is like, okay, this, we're fine. Or 30, because 30 is a tough one. So I hope that they watch this and realize that it, it does, it's going to all make sense at some point. Maybe just not yet.

Stephanie: Yeah. Yeah. Just keep going.

Lauren: Yeah. Like just power through, you'll get there. I promise.

Stephanie: Right. Right. Right.