EP 157: The Ambition Penalty: Stefanie O'Connell on Why Wanting More Still Costs Women

Speaker A: This isn't just a workplace issue. It's a much broader issue that's shaped by cultural ideals of what it means to be a quote unquote good woman or a good man, and how that's really, for women in direct conflict with what it means to be a quote unquote good leader or worker. Clearly, the behavior is not the issue. The issue is a system that treats that behavior as something good or bad, depending on who is doing it.

Speaker B: You say the word ambition, especially to women, and it brings up a complicated mix of emotions and beliefs. On one hand, if you're not ambitious enough, you're the problem, and if you're too ambitious, you're still the problem. And this pervasive polarity that has quietly shaped how many women communicate and own what they want and go after. And many women, myself included, move into midlife and reflect on wants and needs and ambitions. And there's an awareness of how burdened our ambitions have become and how that impacts how we see ourselves and the world. Now, uh, today's conversation names this tension, traces it back to its roots while offering clarifying language for reclaiming our ambitions together. Rebecca I'm Rebecca Ching, and you're listening to the Unburdened Leader, the show that goes deep with humans who navigate life's challenges and lead in their own ways. Our goal is to learn how they address the burdens they carry, how they learn from them, and become better and more impactful leaders of themselves and others. Ambition is a complicated word for just about every woman I know now. For me, it wasn't until my 30s that I started feeling the weight of the word. And becoming a parent totally accelerated that. But what's interesting to me is that, you know, when I reflect back, I kind of see because of my stubbornness, the way that I'm wired, I had just enough cluelessness and a lot of privilege that there's something I wanted. I went for it, especially in my 20s. But as I entered further into adulthood and parenthood, juggling multiple loves like my marriage, my kids, and the ambitions I had for my work, I started to feel a conflict I hadn't felt before. And then I heard out loud what I'd been sensing. Someone I know told me that when she mentioned my name to someone else, the person said, oh, she's so ambitious. And the person who told me about this exchange wasn't sure that was a compliment, but I knew immediately it was not. This was shared with me about 15 years ago, and it still stays with me. And what I didn't fully clock in that moment was how much I'd already started to shrink because of my growing burdened view of ambition. I started not to name my successes and minimize accomplishments and the big things I was going for and work and in life. And I think that's in part because when I'd shared something I was really excited about or that I achieved, I would experience this chill, like I said something really inappropriate. And there were so many mixed messages coming from every direction on what it meant to be successful. My faith, community, the mom blogs everywhere. When my kids were small, the models I had of women who are working all sent conflicting messages. Work and family were presented as polarized and you had to choose. And I didn't even bring up health or well being. So when my kids were in elementary school, I started to really feel stressed. I mean, that's like no surprise, right? But work and family, they were fighting against each other and I was the battlefield. And I remember real vividly this moment sitting at my desk, looking at all my stacked and organized to do lists and something clarified for me. I love the work I get to do. I love my family. And they're going to be on the same team. I am not going to pit them against each other because I found myself, like, feeling, oh, I can't do that because of work. Oh, I can't do that because of the kids. And both felt crappy. My ambitions, my hopes and my passions around work and family were reflections of me and not threats to each other. But what I didn't fully understand yet was how much of a fight it would be to keep them on the same team. Not because of any failure on my part, but because the system I was operating in was designed to make exactly that fight inevitable. Now, my guest today names this vice grip at the center of all of it. If you're not succeeding, you're not ambitious enough. If you are succeeding, wanting a lot and going for it, you're too ambitious and you get penalized or punished. And she talks a lot about this in the workplace, but I think also socially too, in the home and the communities that we move through every day. And it's not just imposed from the outside. I think this is what makes this conversation so important for anyone who does the kind of internal work that we talk about on the show. The system gets inside us. We start to police our own ambition. We police each other's ambition. We breathe in the burden messages around what women are supposed to want. And without realizing it, I, along with many I know and work with felt increasingly unmoored. Now, um, my guest today cited research in her book on the paradox of meritocracy that the organizations that believe that they're the most fair and just and equitable actually perpetuate the most bias. And this conversation also connects with my recent Unburdened leader conversation with Nilafir Merchant. You know, something that Nolefer said is that we're living inside invisible norms that we didn't choose and often can't see. And my guest today names even more of those invisible norms but around ambition for women. And she brings nearly 450 pieces of research citations to back it up. I love a, uh, good appendix in a book. It's awesome. I am so thrilled to welcome Stephanie o' Connell to the podcast and I'm so excited for you to hear more about her and her new book that just came out now. Stephanie is an award winning journalist, the author of the Ambition How Corporate Culture Tells Women to Step up and Then Pushes Them Down. Her work dismantles the myth keeping women from equitable pay, leadership and power one data point at a time. So as you listen, hold these questions. Where have you learned that your ambition is dangerous? And how is that showing up? And, and how you lead yourself and others right now? Where might you be colluding with the very system that's penalizing your ambition without knowing it? And what would it look like to stop carrying this burden view of ambition alone? All right, everyone, now let's get to this conversation. Stephanie o', Connell, welcome to the Unburdened Leader podcast. I am so, so excited for this conversation.

Speaker A: Thank you for having me on.

Speaker B: This, uh, book is, is important on so many levels and I, so I want to start off going a little bit back in time on the history of this new book that we're going to be talking about that you have dropping. Um, you've been covering women work and money for over a decade and you wrote this column about 5ish years ago titled Stop Punishing Women for Being Ambitious. And that inspired eventually what became the book the Ambition Penalty. But after that column dropped, your inbox flooded with people responding to what you wrote. Take me back to what was going through your mind when you started reading email response after email response.

Speaker A: Well, I had really written this column that reflected a lot on what women have been told for decades are their greatest barriers to opportunity, advancement, pay, power. And that was these myths and misconceptions like women just don't ask for more. Women aren't confident enough, women aren't aggressive Enough, they're not competitive. And what the column was really about is looking at what happens when women are asking, when they are leaning in, when they are speaking up, and finding that not only were they not able to access the same kinds of opportunities and rewards for doing so, but. But a lot of them actually faced backlash and penalties for even putting themselves forward in the first place. And so for decades, we've sold women this story that the reason they don't have equal pay or power is because they're not ambitious enough only to find that women are actually having their ambition weaponized against them. Um, and what I saw in these stories that I got in response to writing this column was this was not an anecdote. It wasn't an exception. It wasn't something that was happening in one particular industry or among one kind of woman. It was happening across class, it was happening across race, it was happening across ages, it was happening across industries. And that really inspired me to do a data deep dive. And that's what this book really is, is, yes, there are many stories throughout the book of women who've experienced this kind of backlash. And to start understanding what it looks like and that it's not just them, um, but also contextualizing their stories within a broader story of what is facing all women in contemporary culture that effectively reproduces the same kinds of inequality, even as more explicit barriers to women's participation fall away.

Speaker B: You did it so well. You really did it so well. Just give. I. I kept having images of my own work journey come up as you would either quote some of the women you interviewed or synthesize the data that you were finding. And so in your book, you write just the basic fundamental, defining ambition from your lens is to be ambitious simply means. Okay, drum roll. To have ambition.

Speaker A: Yeah.

Speaker B: Nothing fancy, right? And you said, this is the drive to create a life that refle your unique skills, interests, and values and the desire to be valued for those qualities and abilities that you value in yourself. And I just want to pause there, because there isn't moral meaning here. And I always say to my clients, where there's moral meaning, there's shame. This is just kind of a matter of fact data thing. But then you also write that about the data you were collecting, the women, and the stories that these women were not held back for lack of a mission, but because of it. Like, you just shared the pushback was the penalty. So I'd love for you to define the ambition penalty and why naming it matters so much.

Speaker A: Yeah, So I define the ambition penalty as the sum of the professional, economic, social and personal costs that women face for their ambitions. And it really speaks to the catch 22 that is at the heart of what modern women are facing today. Today, where we have told people that to get more of what they want, whatever it is, that they really just need to lean into it and harness their ambition to go for it while simultaneously punishing women when they do those very things. And you see that double standard come up across gender identity in a way that really, uh, enables men's access to greater power, resources and opportunities while simultaneously blocking women's access to them, those things. So when I talk about, you know, financial, economic, professional costs, I'm talking in material terms. It's not just about saying, well, she's ambitious and we don't want to work with her, and he's ambitious. Wow, what a great guy. It's about, how does that translate into who gets hired, who gets mentorship, who gets access to training and support, who gets promotions, who gets more pay, who gets advanced into leadership, and who is put down and put down and put down. Or constrained. And constrained. And constrained. And I also write about in the book that this isn't just a workplace issue. It's a much broader issue that's shaped by cultural ideals of what it means to be a quote, unquote, good woman or a good man, and how that's really, for women in direct conflict with what it means to be a quote, unquote good leader or worker. There is this, this constant tension that shows up, sure, in our workplaces, but in our homes, in public life, everywhere, where as soon as you have a woman, you know, assert her independence or asserting her power, even if it's not in a workplace, you often have this reaction to her that would be much more likely to be negative relative to her male peer who engages in the same behavior. And so what I'm asking in this book is like, well, clearly the behavior is not the issue. The issue is a system that treats that behavior as something good or bad, depending on who is doing it.

Speaker B: And that negative reaction, we're going to get into this a little bit is not just a negative reaction. Sometimes it's a deadly response. Absolutely or incredibly harmful. Walk me through how you see ambition became such a dirty word. And I've had this said to me so many times, and I remember thinking, I don't think it's bad thing, but why do I feel like I just got slimed, Right? And that when you say someone's ambitious, it serves more as a warning. Than an affirmation or a compliment. Yeah, walk me through that.

Speaker A: Yeah. I mean, it depends on who the word's being applied to. Right. Even if you just change the pronoun. Right. He's ambitious. Not said in a derogatory way. Said in a very positive way. Used to affirm, to uplift. She's ambitious is where it really starts to shift. We start to become skeptical. We start to think she's not a good fit. Right. She's, um, not grateful. She's not a team player. Again, the problem isn't the ambition. It's the idea of who's expressing it, being what makes it good or bad. That's the problem. And really, these come from these broader ideals of things that, uh, maybe we are not comfortable admitting, but certainly show up in our behaviors. And that is the idea that it's men who should hold power and resources and be in charge of, you know, the. The public sphere. And that women should really just be involved in supporting men's power and only participating in the public sphere to the extent to which their labor upholds men's power. And most people would not say that they agree with that, but their behaviors do align with that ideal. So another great paper that I talk about in the book is how they were studying, uh, women in leadership. And what, you know, we obviously know women are very underrepresented in leadership positions. And still this true today. And there's this question over why. Why is this still playing out even as women have become more ambitious than ever? And what the paper found is that people wouldn't say, well, we're not going to promote her because she's a woman. Instead, what they would do is weaponize another identity characteristic against her, again through a double standard that was not applied to her, her male peer. So it would be, well, she is too young for leadership or she is too old to be seen as a leader. But man, same age, that's fresh new thinking. That's the guy we need on our team, the older man. He's, uh, seasoned, professional experience, has wisdom. We need him on our team. So it's another one of these examples of how you can create the same unequal outcomes while really disguising it through standards that differ across identity.

Speaker B: And you name that. This is as much a power problem as it is a gender problem. Can you say more?

Speaker A: It's this idea of who should be holding power. And again, this is not something people are acknowledging explicitly. And even if you point it out, they're going to be very hesitant. They're going to say no, I don't think that women don't, shouldn't be in positions of power. It's just that what these double standards do is they effectively create a disguise. And that's how you get to a world in which not only are we having the same inequality generation after generation after generation now, but we also have this mass gaslighting machine layered on top of it. That it's not the fact that this kind of double standard is being used to recreate these outcomes. It's just that you're not ambitious enough or confident enough for whatever it is. It's a you problem, not a problem of these double standards. And so when you understand that we're talking about systems of power and how they're upheld through these different, uh, incentives and disincentives, rewards and punishments that change depending on the identity of the person, right? If you express ambition as a man, you'll be rewarded. If you express ambition as a woman, you're more likely to be penalized. Then you can start to see how you get that power structure being recreated. Even as you have more education than your male peer, more ambition than their, your male peer, more experience than your

Speaker B: male peer, more skill.

Speaker A: More skill, more everything. Right? And we're seeing this play out. And I think one of the reasons I wanted to write this book is, you know, I'm turning 40 this year, so I'm a very textbook millennial and I was part of a generation. And I think this is also really true for Gen X that was really brought up on the prom that, you know, if we, we were the future, like we were the ones who were gonna have a, ah, different outcome because not only were a lot of the legal baron bans and barriers stripped away relative to previous generations pre civil rights, pre women's movement, but also we were raised with tons of this, like girl power and confidence. We grew up on a lifetime of having our ambitions championed, only to then become adult women and have that suddenly flip into backlash. And one of the things that I write about is the reason you get ambition being seen as a good thing in girls is because they're not. Girls don't threaten systems of power. It's all about the potential of power when you foster a girl's ambition. But when a girl is a woman, when she's uh, a grown up and in the adult world, suddenly her assertion to power really challenges a system that says power is really to be rewarded and helped by men.

Speaker B: Okay, so a couple follow ups here that I think are noteworthy. Just even on Owning ambition. Because of all that. You said you noted some data that half of the women surveyed were privately would identify as ambitious. Like, yeah, I totally am. Um, but only 31% of those folks would proudly claim that forward facing publicly. So what's at stake if we don't shift the shame on women?

Speaker A: I mean, really so much. I, um, I hope that what people walk away from this book with is not just understanding how these systems are playing out, but also understanding that what they're experiencing is not by accident, it's by design. So if you suddenly feel totally depleted, totally disillusioned, maybe like you don't really want anything anymore after all, that is not something that's natural. It's not something that is happening by accident. It has been purposefully engineered. And I make the case for how that happens throughout this book. Um, but what I'm really pointing out here is because we have been conditioned to believe that the barrier is ourselves, right? When we talk about things like you just need to be more, um, ambitious, just confident and, and that's why you can't get ahead. Basically what we're teaching women is that their greatest barrier to opportunity is inside of them. And it's an individual problem and not a problem in the world around them, not a problem in the environment that says if you do this, it's good, and if you do this the same thing it's bad. We are taught never to see things that way. And instead we're taught that, well, you know, if it didn't work out, then you probably didn't ask the right way and you were probably like a little bit too aggress and you need to really just be more warm. And because we've been raised on a lifetime of this idea of self optimism, self optimizing our way out of inequality, when we experience backlash and penalties, we are already conditioned to see ourselves as the cause for it, to agree with it, to agree with it, right? And then that has the cost. Then our aspirations erode, uh, over time. Not because that's when it comes happens to you biologically as a woman, but rather because that's what happens to anyone in an environment where they are chronically put down instead of lifted up and under supported and overworked. That is not a gender thing. It is a gender experience. Oh.

Speaker B: Uh, yeah. So one of the things that I've been really fascinated about in my own personal journey, but also in my journey in my work with clients and leaders, is how women collude with the very things that are harming them it's something that I dive deep on. And you had a whole chapter even on why we love to hate ambitious women and even noting that often women are kind of side eyeing and rolling their eyes and like, uh, I don't know, you know, like we often turn on, eat our own. You know, there's all these phrases out there. Are there some specific examples of women colluding with hating ambition in other women that stood out to you in your research for this book?

Speaker A: Oh, I, as you said, I wound up dedicating a whole chapter to this because I think it's so, so important to understand again, to name often when we talk about things like inequality and what drives it, whether it's sexism or racism or any of the isms, we think of it as this very individual thing. I am treating you badly because I am sexist or racist or whatever it is.

Speaker C: Right.

Speaker A: And we think of it as this individual to individual thing instead of understanding that actually we're all living in a world that is constantly telling us and constantly reinforcing these broader ideals of what, what power is supposed to look like, what role men are supposed to play in the world and what role women are supposed to play in the world. And of course that intersects with other forms of identity. And it's really interesting in the research we see that it's actually the organizations that most think of themselves as meritocracies where they perpetrate the greatest bias because m, they already assume that they are unbiased. So instead if you assume you are biased, especially in cases where the identity of the people that you're evaluating, for example, align with your own. Like that's often where people let themselves off the hook. You think, I can't, I couldn't be, possibly be biased against women because I'm a woman, Right? Then you're automatically in trouble if you're not scanning, you're, if you're not checking in with yourself because again, we're all raised with this and it's active conditioning that to, to decondition. It's an active process. Something you always have to be keeping in mind. Now in terms of um, you know, really understanding how this patriarchal, uh, power works to get women to turn against other women. One of the really interesting examples to me is what happens when one woman is elevated into a position of leadership, as is often the case. Instead of getting women in leadership as a meaningful share of leadership. Remember, like, women are not minority, but the way we talk about women in leadership, we, we, we talk about it like it's acceptable that, you know, 5% of leadership is women, as though they're not half the population. And what that effectively does is it really limits the power of the women who are in those roles. So their voices can be easily sidelined, even if they're in a position of power, because they're not represented within the leadership structure in a meaningful capacity. Anything they say really can just be written off. They don't need to be listened to. They don't really have the power to push back against the culture, even if they are actively trying to do so, if they don't get enough buy into their ideas. And that's a really effective way of casting those women as ineffective, as casting them as the problem. And sometimes, you know, they might be, sometimes they might be the problem. But for the majority of the time, what we actually see in the data is that when women are represented in leadership at scale, scale, you know, closer to 30, 40, 50%, you really do see outcomes change. You do think, you do see pay gaps close. You do see promotion gaps close. The most compelling thing to me in understanding the research in the chapter on, um, women as participants in patriarchy was really understanding the way in which the system itself incentivizes this kind of competition. Uh, incentivizes us seeing each other as competition instead of what the data show us. That is that when women are in these positions together, the outcomes improve for everyone.

Speaker B: I want to circle back on something you were talking about, like, if we own that, like I often talk about the air we breathe. If you own that, you breathed in the, uh, burden systems of biases and just know, oh, wow, I need to always stay curious and be aware of that versus, wait. I work for a company that says it's, you know, and all these little points in their values and their mission, but there's nothing to back it up. That is dangerous. And I guarantee you there's people listening to this podcast, they're thinking about, you know, people that they have, like, spoke the lingo of whatever we're going to talk about empowerment lingo or whatever the latest, you know, trend is, but then it are really harmful, um, psychologically, emotionally harmful in how they lead those around them. And so that actually takes vulnerability, that takes courage, that takes having a capacity for discomfort and not clinging to a power like it's been taught to us. And I think that's the biggest unlearning and it's a risky thing. But I love that posture of just like, I am biased, not as a moral meaning, but it's just A data point.

Speaker A: Correct.

Speaker B: I caught my biases, given the identities I hold, the story I've lived, and what am I missing? And, uh, that's it.

Speaker A: Yeah. And. And I think it's about exactly how you're framing it, about being curious about it, trying to understand it, and trying to see how it's showing up in the world around you, where it's coming from, how you're reinforcing it or pushing back against it. This is a, uh, daily practice, and I don't think it's something we check off. Like, it's not a box to check.

Speaker B: So you, you touched on this a little bit. You wrote about this in your book about, you know, empowerment culture and the. How it collides with hustle culture and a lot of us. I mean, I'm, um, I'm a Gen Xer through and through, but all of us, I think, have been impacted by that whole movement of just, you know, who runs the world and, you know, be brave and girl boss and, and. And then subsequently, over the last handful of years, I've seen people start to deconstruct that. Yeah, I guess I'm saying too. And women are right now so exhausted, they're cooked and more strained than ever as people are deconstructing that kind of empowerment and hustle culture. What stands out to you? After interviewing all these women and digging

Speaker A: into the research, the thing I come back to over and over again is the extent to which we have been always conditioned to turn into ourselves. And I find that even when we learn to recognize the causes of our exhaustion and disillusionment as systemic, we still will try to frame the solutions as individual. And you really see this in the way we talk about things like self care and burnout. Oftentimes we are still basically doubling down on the idea that it's an individual optimization issue, that if you just take enough bubble baths, then suddenly you're not gonna be in a world in which you're being constantly worn and torn down. And that's just not the case. Right. We have to get out of individual and internal and flip the framework to what I refer to as empowerment from the outside in. So really externalizing social inequality, understanding that it's not something that's coming from within us, but in response to the world around us. And, and the other piece of the puzzle here is also understanding that the, the way forward is also not individual. It's collective. When you understand that the barriers are not inside you, but around you, what you also start to understand is that the barriers are not individual, but they are shared. And to push back against a shared barrier, you're going to be much more effective if you work with people instead of alone. We have to work together in tandem, you know, and that's why we see in history every really meaningful movement in shifting outcomes has been a collective movement. It's been, you know, civil rights movement, women's movement, union, labor movement. Like, like that's the stuff that gets you to a stratospheric change instead of promising you that, like there's something you can individually self optimize your way into achieving.

Speaker B: And I'm seeing more and more people acknowledge this in, in their books and their writing. It's one thing though to have systems thinking, and then there's another way, I think, to have systems leading. It's not a kumbaya moment. Coalitions are not everyone 100% aligned. But when we're thinking about a team, you know, where you are working for an organization that you've. Everyone's chosen to be there and shared mission and values. I think that is really important. I want to touch on that in a moment. But before we move on from the women being exhausted too, you noted. And I'm not sure I'm going to say the name right, um, you cite. Is it Maslock?

Speaker A: Christina Maslock.

Speaker B: Uh-huh. Yeah. Maslach. Burnout framework. Uh, this is new to me. Yeah. Love that you brought this in. I wanted to acknowledge it. How can, how do you see this framework helping counter the ambition penalty not just for individuals who are aware of it, but for leaders, um, that are in charge of teams and HR professionals and so on?

Speaker A: Yeah. So this is psychologist Christina Maslach, and she started really studying workplace burnout back in the 1970s. And she uncovered these three main components. And that's, that's first what we all think of when we think of burnout. Just being totally exhausted, physically emotionally overload, stress, fatigue. Then you get cynicism. That's when you want to stop showing up as your best self, engaging in your best work. This is where we see people saying, well, I'm just not ambitious anymore. Right. We're kind of like disengaging, stepping back, quiet, quitting whatever you want to call it. And then you get the self blame again. All things we've been talking about. And so we think, uh, again, that our burnout is not a result of the totally unsustainable environments that we're encountering or these unsustainable expectations and the demands and double standards. But instead we think it's just us, it must just be me. And the solution to it just being me is to stop wanting any of it at all. Myself. And what Maslach really talks about is when you look at burnout through this framework, like, first of all, you can see how this is showing up in contemporary culture everywhere you look. But you also start to see how our way of addressing it is really misguided because it's really, um, again about your relationship with the world around you, not your relationship to yourself or your desires or your wants. It's really more about how the world is making that those desires or wants completely unsupported, completely unsustainable, and much more so for some people than others. And so burnout is essentially this stress response from this fundamental mismatch between ourselves and our environment across six key domains. Uh, she studies this in the context of workplaces. But I argue that this is a, uh, framework we can extend to, to work, whether it's in the paid labor force or the unpaid labor force.

Speaker B: Exactly.

Speaker A: Because it's absolutely consistent. Right? So you have workload. When you have too much to do, you don't have enough time, you don't have enough support, you don't have the resources to do it. You have control. So that's really like the idea of autonomy having say over how you work. When you work where you work, you have rewards, that is how much you're being paid or valued, recognized, rewarded, you have community. Do. Are you being self supported in your labor? Are you being undermined, the opposite of building community? Then you have fairness. So I think that's pretty, uh, self explanatory. If you're not being treated fairly, if you're being subjected to misogyny, if you're being subjected to racism, classism, ableism or discrimination, that's going to exacerbate your burnout. And then you have values. So when you feel disconnected from the meaning of what you're doing or the contributions that you're making, when you understand burnout as a mismatch on these six fundamental things, you understand that like, again, this isn't something that's just happening inside of you or what you, what about what you can't handle personally? It's about how the environment around you is exposing you to these chronic stressors and how some of us are being exposed to those stressors a lot more than others because of the bias in the environment around us. This A lot of what you see in contemporary culture, especially in messaging directed at women, is that the workplace is completely unsustainable for women, and so they should withdraw from it entirely. But if you think about Maslach's, uh, burnout framework, along these six key elements of workload, um, control, rewards, community, fairness and values, actually, that doesn't really solve for those mismatches. In fact, it can really exacerbate them. Like, then you get. Then you're working for no money, and then you have much less community. Oftentimes when you're just constrained to the home and you can't access rewards, or you're far more. You can be much more subject or vulnerable to things like unfairness, and you may have a lot less control as you have less access to economic autonomy and opportunity. This is where I really want people to recast the way we're thinking about these things in any context and to say, like, how do we make sure all of us across identity are getting

Speaker C: more alignment with these six elements, no

Speaker A: matter where we are? So if you're in, you know, management, or if you're in hr, what is

Speaker C: it that is a mismatch? Is it. It might be several of these elements. Is it. Is it the control? Right. Is it that we're not working flexibly when we absolutely could be?

Speaker A: Um, and I give a number of

Speaker C: examples in the book about, like, you know, flexibility doesn't have to look like any one thing. It can look like a lot of different things. It just doesn't mean that we should just take this entire pillar off the table because it's essential. Like, all of these pillars are essential. And we're in a world where it's just not acceptable for us to be saying, well, let's get rid of this pillar altogether, because that's really hurting all of us. And that's why we're in a place where so many of us are completely exhausted. And feeling like this is also unsustainable is because, like, the commitment to making sure our environments are fulfilled, are aligned with these fundamental six core needs is just really shredded, really shredded. And I think for people who are interested in retaining their workforce, they can start with those six key elements.

Speaker B: What I love about this framework, whether you're feeling burnt out or not, but it's a really good tool to go through to deconstruct the very things you're talking about. So when I was zooming out and thinking about that, I'm like, this is a great kind of thing to go through and go, where do I land on all these things? Where are my vulnerabilities? Where are my biases showing up in my responses to these things, and you also talked about, uh, you referenced this a little bit, but the quiet quitting and all those other trendy ways of framing people leaving the workforce. And you really identify, you kind of said, listen, sometimes that is helpful and go if you need a change and take a beat. But tapping out is actually hurting collectively more than empowering. Can you say a little bit more about your thesis around that?

Speaker A: Yeah. And, uh, this is not to say that I don't think people should take breaks from. For sure, they need to take breaks from paid labor. What I don't want to do is recast people being pushed out of the labor force and access to opportunity and economic autonomy and power as empowering. That's not empowering. What's empowering is creating systems where everyone is as able to realize their ambition and be as supported and have access to, first of all, economic autonomy, no matter how they're engaged in paid labor or not. Um, but I have really seen, I think quite toxically, even in the last year, people reframing the fact that 400,000 plus black women were pushed out of the paid labor force in 2025 as, like, women choosing differently. Like, it was wild. It's disgusting. It's really disgusting. It's like this idea of, like, oh, it's actually not a problem that women's earnings and their leadership kind of stalls out a decade before men. And that, uh, by the time women are 35, their wage growth essentially flatlines because they're just choosing a different path. That is really, really awful. It's a way of kind of placating something that is devastating. People do not have access to basic stability. And often in midlife, which are often the most expensive, stressful years of your life. And we're gonna reframe that. To what? To, like, to provide cover for some of the most discriminatory and disgraceful policies we've ever seen play out in, like, the labor force in the United States. I just, uh, in contemporary culture, I cannot, I cannot engage with that kind of, of reframing or retelling of this story. And that is not to say there isn't a story about, you know, how would we cope through constraints. How do we deal with these realities? How do we deal with the fact that we're in facing circumstances where we are often targeted and like, there is a story of resilience to tell of, of building back. But that is not the same thing as, uh, saying that women being a very, very targeted group of people being pushed out and pushed Away from the engine of their, um, economic autonomy and opportunity is empowering.

Speaker B: I just wanted to name that. So thank you for bringing that home. And so as we wrap up this discussion, and it's, I, I hope it's not the last one we have because this is so spot on for so much of the conversations we have on the show and the work I do. But you talk about this is not about individual work. It's about how we have collective ambition, which, you know, even when I say that out loud, those parts of my body kind of goes, are people really going to be on board with this can? Is it safe? And I want to read a quote, uh, from your book. You said, instead of conflating our understandable coping mechanisms with real solutions for these stressors, we'd all be better off realizing our shared interest in leveraging our collective power for more manageable workloads, greater control, more rewards, stronger community, real fairness, and more meaning for all of us. Is there any story from your conversations and your research of what this looks like, not just theoretically? Is there, has there been a business or a group where you saw what you saw this look like in substantive action? Um, you referenced labor unions and other folks in our history. But right now, is there something that you see or a group or a business that's doing this substantively?

Speaker A: I mean, this work is being done every day. And one of the ways I break this down in the book is trying to understand systems as not just something that's happening at a workplace level or at a level of federal policy, but is happening in ways we interact with every day. So I break it down into the interpersonal sphere. In your home, you know, when you talk about heterosexual relationships, specifically heterosexual marriage, that's an institution, meaning it's shaped by norms and customs that reinforce a lot of these dynamics. And every day that you're in that institution, you have a chance to challenge it, to challenge the way not necessarily your relationship with your partner themselves, but rather the idea that that institution is that only, um, one person is allowed to hold financial power or be the ultimate financial decision maker, and that the other person, person's labor is designed to uphold that person's financial power at the expense of their own ambitions, time, everything else. So, uh, that's just one example. At the interpersonal level, certainly in the family dynamic, you know, the way daughters and sons expectations differ wildly around, you know, again, whose labor is to be basically exploited in terms of, uh, we completely expect women to sacrifice everything they want for themselves. Their economic well being, autonomy, long Term health and well and care to care for everybody else to be completely self sacrificial. Well, boys are rarely tasked with the same amount of expectations. The extent to which this inequality is being reinforced every single day. Two days in 2026 it starts. Honestly, I have a toddler. I am blown away. I've been reporting on these dynamics for years. You could not have prepared me for how sexist people still are with babies. And I noticed it from before my daughter was, was born. Immediately this, you know what, you know, oh, you're so lucky. You know boys, you know, there's this real, real commitment to uh, to, to, to creating a story of fundamental difference that, that works to then justify a lot of the power dynamics that we see play out throughout life and later in life. You know, ex excusing bad behavior of boys even when they're very little and holding girls to a much, much sooner, expecting them to contribute so much more, valuing their labor so much less. I mean again I, apparently we're supposed to be so much better but I don't see any sign that we are parenting in a, in a meaningfully different way that's going to create a different outcome. So uh, that is not me being like poo poo. There's nothing you can do. There is something you can do, but it is about really recognizing how these dynamics are showing up in our day to day life. And then you have the institutional level. So then you're, we're talking about these workplace relationships, we're talking about the policies and practices that are showing up there. And then we're talking about the political and cultural level. And again that's not just federal, that it can be local, that can be in your own community, that can be in your own city, your own town, your own state. Uh, I think the opportunity for change is really clear. And I live in New York City and I think New York City, speaking of examples, has been a really interesting uh, purpose proof point because since the beginning of just this year in 2026, we now have our 3K being expanded, free, universal, 3K being expanded. Next year there's going to be a child care for 2 year olds. I'm not sure if it's in the whole city, but uh, at least a part of it. And this is in a matter of months these policies have been instituted. And so what it really makes clear to me is that there was not there and there never has been a lack of solutions. We know what the solutions are. There is a lack of political will and there is a Lack collective coming together to bring that political power into place. And I can say the same thing about any kind of power, right? If you can really get out of this individualistic myth making and the internalizing the responsibility for the problems and coalition build, then you can bring those forces to power that are going to institute those policies that you've been told for decades could never be implemented, would never be acceptable.

Speaker B: I often say this to my clients, um, so sound familiar to them for those of listening that homeostasis fights to the death to maintain status quo. So that frustration, even as a mom of a toddler, things that we're seeing in businesses and politics, we're literally living in a timeline right now where the pulls, um, to change. There's a lot of fear and scarcity. And I think we just got to stay the course. And having conversations like these hopefully will encourage folks with their inner system to have more courage and curiosity and conviction to, to stay the course and, and to, to disrupt. So one of the traditions I have at the end of my show is to ask some kind of quick fire questions. So you ready to move into that, Stephanie?

Speaker A: Yes. And I did get a peek at them before and I remember thinking, oh, I think I have answers to all of these, but I might not be sure. So we'll see how it comes out.

Speaker B: We'll rock and roll. We'll rock and roll. General so what are you reading right now?

Speaker A: I just read a wonderful memoir called My Mother's Daughter by Tracy Clark Flory, who wrote about her mother who had a baby 20 years before she. Tracy was born, uh, in the 1960s and she was, uh, she had a teen pregnancy out of wedlock and she was sent away to a, uh, home for unwed mothers and forced to give the baby up for adoption. And it's really about Tracy reconnecting with her half sister because of a DNA test after her mother's passing and then exploring the history of speaking of shame, uh, how we shame and stigmatize women and motherhood and the way that we all kind of carry that burden.

Speaker B: What song are you playing on repeat?

Speaker A: Um, uh, the Ragtime Musical, uh, revival at Lincoln Center. I'm a musical theater geek and the current Me Too revival of Ragtime at Lincoln center in New York. Uh, Joshua Henry is headlining and he's just one of the most spectacular live performers I've ever heard.

Speaker B: Magic. What is the best TV show or movie that you've seen recently?

Speaker A: Yeah, this one was, I was really struggling with because I love television. But recently news to I'VE been rewatching a lot of stuff.

Speaker B: That's fine too. Even rewatching.

Speaker A: Yeah. I mean, I was definitely rewatching Mad Men recently because it came up on HBO and it's like my fifth or sixth rewatch and I did a whole, like, deep dive on my Mad Men rewatches in the context of 2026. And I realized my experience of Mad Men changes every time I rewatch it because I am different. Not that the show is different. And I just noticed my tolerance for. I. I don't see. I think Don is like, despicable. Um, whereas I think when I first saw it, I thought, oh, he's so good looking. But like, I can't be fooled anymore.

Speaker B: I. Very similar experience. Still very good looking and still very good looking. More despicable.

Speaker A: Yeah.

Speaker B: And less sympathetic every time.

Speaker A: That's it. Yeah.

Speaker B: Yeah.

Speaker A: My. My capacity to make excuses for him forever, it's just gone.

Speaker B: Yes. And I think that's the conditioning, right? The making excuses. All right, what is your mantra right now?

Speaker A: Oh, done. Just do it. Done is better than perfect. You can't do everything. Let it go. That's a lot of mantras.

Speaker B: They go well together. And what's an unpopular opinion that you hold?

Speaker A: Um, I have many. I think what New York City is one of the best places in the world to have a child.

Speaker B: That, that, uh, is polarizing.

Speaker A: Y.

Speaker B: What is something you've changed your mind about recently?

Speaker A: Again, a lot of things. But I would say, uh, thinking back about what I would do differently, I used to think when I look back at, ah, certain times in my life, there's nothing I would do differently. But I think I've changed my thinking on that in writing this book because I. I, uh, wish I would have thought more collectively sooner. I wish I understood that I didn't have to do it alone and that I could be so much better served in coalition building.

Speaker B: Who or what inspires you to be a better leader and human?

Speaker A: My friends. Speaking of coalition building, some of my best friends in my life are people I've made in my 30s and warms my heart.

Speaker B: That's awesome.

Speaker A: The book is dedicated to two of those friends. And those relationships are, um. They're so special because those, you know, I said to be seen and valued for those things that you value in yourself. When we talk about ambition and having people who see that, who see you for who you are in the way you want to be in your life now, not necessarily like what they imagine you to be when you grow up or in A certain context. It's so special. It's maybe the most valuable thing in my life other than, you know, my baby. So, yeah, I really don't sleep on those friendships.

Speaker B: Yeah. And I think that's part of the medicine and what really disrupts the very systems that we're talking about.

Speaker A: Because you build resilience, too, through it. Uh, you know, I wanted to add before that. You know, I'm not saying people aren't going to face backlash when they challenge the status quo either.

Speaker B: Yeah.

Speaker A: But you can better make, you can better, um, stand up to that and, and take that backlash on when you're in community because it gives you resilience.

Speaker B: It's really medicine and courage. Stephanie, thank you for this conversation. If folks wanted to connect with you, your work, your writing, your book, how can they connect?

Speaker A: The book is the Ambition Penalty. How corporate culture tells women to step, step up and then pushes them down. I know we've been speaking really theoretically here, but it is incredibly Data driven. Nearly 450 citations in the book. For context, most nonfiction books are about 50 or less.

Speaker B: A gorgeous citation section. Awesome.

Speaker A: Yes. So you can really drill down into the details if you'd like. Uh, and I talk about all this stuff, um, on my newsletter, on substack, it's too ambitious.substack.com and on Instagram. I'm pretty active there at Stephanieocom.

Speaker B: Thank you so much. I am so excited for people to read this book and be exposed to your writing and your work. So thank you so much for your time and love this conversation.

Speaker A: Thank you for having me.

Speaker B: Before you go, here are some important takeaways from my unburdened leader conversation with Stephanie o'. Connell. One of the first, like core thesis of her book and her body of work is that the ambition penalty is not a personal failure. It's the impact of the burden systems we live and work. The catch 22 Stephanie names is this. If you're not succeeding, you're not ambitious enough. If you are succeeding in doing what you want, you're too ambitious and you get penalized. That double bind is not accidental. It's engineered to keep the existing power structure exactly where it is. We absorb messages about what women are supposed to want, and without realizing it, we start enforcing them on ourselves and each other. Now, Stephanie's clear. This is not moral failing. And remember, wherever we have moral meaning, there's shame, you know? And she goes on to say, it's what happens to anyone conditioned inside a system that's been running this long. The work of deconditioning is daily, uh, and these days it feels like it's never finished. And Stephanie adds, the way forward, it's not individual but collective. And I think this is a theme team been talking about so much on the show. Every meaningful shift in history has come from people recognizing that a shared barrier requires a shared response. Can't do this alone. And Stephanie said you will be far more effective pushing against that barrier in community than alone. So as you move forward from this conversation, I want to return to those questions that I asked you at the top of the show. So where have you learned that your ambition's dangerous, and how is that showing up in how you lead right now? Where might you be colluding with the very system that's penalizing your ambition without knowing it? What would it look like to stop carrying this burden View of ambition alone? Naming what's been unnamed? Getting curious about the messages you've absorbed and the ones you're still passing on. Choosing one decision, one conversation, one coalition at a time to stop shrinking and start building together. This is the ongoing work of an unburdened leader. Thank you so much for joining this episode of the Unburdened Leader. You can find this episode show notes, free Unburdened Leader resources and ways to sign up for my Unburdened Leader substack and work with me at www.w.rebeccaching.com and if this episode was meaningful for you, I'd be honored if you left a rating and a review and shared it with some folks. This helps get some more eyes and ears on the show and I'd be so grateful.