183 | How The Ambition Penalty Contributes to the Gender Wealth Gap with Stefanie O’Connell



Women in the U.S. earn $0.82 and own just $0.32 for every $1 earned and owned by a man, and the disparities are even wider for women of color.” – Stefanie O’Connell


Welcome to episode 183 of Profit Boss® Radio! We’re talking about the link between gender equity and financial power. As women, our achievements are very different from our grandmothers’—or even our mothers’. However, we’re far more likely to celebrate the women in our lives for getting engaged or having babies than when they do something incredible in their professional life. 


Where did this disconnect come from, and why is it so pervasive in our society? To help me answer this question, I’m speaking with Stefanie O’Connell. Stefanie’s a friend, writer, and financial expert on four big topics: women, money, power, and ambition. She hosts Real Simple Magazine’s Money Confidential Podcast and is the founder of Statement Cards, where she produces greeting cards celebrating milestones that aren’t just marriage and motherhood.


In today’s conversation, we talk about why women are hesitant to negotiate (HINT: it’s not for a lack of confidence), what Stefanie calls the “ambition penalty”, and what needs to be done to close the gender wealth gap.


Here’s what you’ll find out in this week’s episode of Profit Boss® Radio

  • Why we’re all socialized to ask the same questions and celebrate the same milestones—and how this often leaves women uncredited for the books we write, the businesses we launch, and our other achievements.
  • Why there’s nothing wrong with celebrating marriages and children—but celebrating only marriages and children limits and reduces us as people.
  • What the ambition penalty is and how it reaffirms traditional patriarchal workplace structures—even for business owners and entrepreneurs.
  • Why ambition isn’t always perceived as an asset, especially with women.
  • How the fear of rejection is not the goal, but is a natural part of the process of being ambitious.
  • How a community can offer us constructive criticism, honest feedback, and help us conquer our fear of rejection.

PBR Clip: Converting Your Ambition to More Money for Your Clients

Resources and Related Profit Boss® Content


Enjoy The Show?

Hilary Hendershott: All right. Profit boss, today I have with me Stefanie O’ Connell Rodriguez. She is a friend and writer and financial expert. She covers women, money, power, and ambition. She’s the host of Real Simple Magazine’s Money Confidential Podcast, the founder of Statement Cards, a line of greeting cards that celebrates milestones beyond marriage and motherhood, which we’re going to talk more about, and the co-founder of Statement Event dedicated to connecting the dots between gender equity and financial power. Stefanie, welcome to Profit Boss Radio. 

Stefanie O’Connell: Well, thank you for having me here. 

Hilary Hendershott: Here’s a quote from your Instagram. I’m not sure if it was your Instagram or Twitter. It really touched me and it moved me, and I’d like to start with it. “Women’s achievements have changed but our traditions and ways of showing up for the women in our lives haven’t. Rarely are we as excited and supportive of women’s personal and professional milestones as we are with their pregnancies and engagements.” Hits close to home. 

Stefanie O’Connell: Yeah. 

Hilary Hendershott: And actually, like because I saw myself in that statement and I consider myself a feminist like an active one. So, how much do you think of that tendency to say, “Oh my gosh, congratulations on your engagement and your wedding and your baby,” is just muscle memory? And how much of it do you think is truly Neanderthal? 

Stefanie O’Connell: I think it’s socialization. I don’t fault anybody for having that instinctive, “Oh, my goodness, congratulations,” reaction. We have been literally programmed to do this. The first thing that you say to somebody when they get engaged is like, “Oh, my gosh. Let me see your ring. Oh, my gosh. Tell me about, whatever, the proposal,” and there is so much in-built excitement because we know what to do. The save the date comes. We put it on the fridge. You get ready for a bridal shower. You look for a registry. There is an infrastructure of support that you plug into. So, it’s as much as even I want to be as excited for my girlfriend who’s finishing her Ph.D., the fact is because there isn’t just this culture and tradition of support that is step one, step two, step three, the questions you ask, the things you do, et cetera, when that happens, I feel at a loss. I’m just like, “Congratulations,” and I feel ridiculous because this is somebody’s life’s work and like something they probably sacrificed for decades, not just getting married. And actually, the thing that kind of inspired this sentiment in myself was actually my own experience of getting married. I got engaged and people congratulated me and showed up for me and supported me in ways I had never experienced in my entire life, despite starting a business, publishing a book, these things that really took effort and I felt were accomplishments. But this thing I did and it’s not saying getting married wasn’t important to me, it was, but it wasn’t necessarily an accomplishment, in my view. 

Hilary Hendershott: Well, being successful in a relationship is the accomplishment.  

Stefanie O’Connell: Correct. Exactly. And I just felt this bizarre disconnect of like, wow, I am only seen and valued as a wife more than anything else in my entire life. And I find with talking to my girlfriends, it’s the same thing who are our wives or mothers or a single. It’s just like, why is that the thing that is like the center point for how people define me, not my goals or my ambitions or what I’ve achieved or whatever else that is? 

Hilary Hendershott: You know, it’s a good point, actually. I’m thinking back to a cousin of mine got her Ph.D., and while I was blown away, honestly, a little intimidated. I mean, and she’s like 15 years younger than me. She got her Ph.D., was in I think it’s chemical engineering or something really intimidating. And I really had no idea like what had she been through. What does that actually mean that she knows what’s now possible for her? What pathway has she been on and where is she headed? I mean, I know it’s good things and it’s a high trajectory but it’s like I don’t know what else to say besides, “Wow, congrats.” 

Stefanie O’Connell: Yeah. And I think that’s probably how people feel when you talk about your business, right? It’s like we haven’t created all of these kinds of rituals and social gatherings and support systems or basically anything else other than like these two major milestones that only define us as women in relation to other people, not in relation to ourselves. And I find that troubling. And I think that I’m trying to talk about it because I don’t think it’s about taking anything away from the way we celebrate weddings and children. I think we should celebrate those things. I just think we need to think more expansively about what we celebrate, how we celebrate, and what it means to really see and support and value somebody for all the things they do in their life. 

Hilary Hendershott: And I have found that as my career has gotten more, you could say monetarily successful, that many friends have actually fallen away, that they say things like, “Don’t forget the little people,” and I’m like, “What? What are you talking about? What’s that mean?” Or they just don’t call anymore. They say, “Well, I can’t relate to that.” And in my past, I admit and this was a long time ago but before I had a modicum of success, I was extremely envious of other people’s success. So, beyond not just saying congratulations for a promotion or a financial milestone being passed, I think I secretly was jealous and I think jealousy is like you want to take that away from them. It’s like I wish you didn’t have that because I wouldn’t feel so bad about myself. I consciously chose to alter that. It was like I’m not going to be that person anymore like that’s not how I’m going to be about that. How has that been for you? 

Stefanie O’Connell: Yeah. I always think my instinct as a kid was to be jealous and I think part of that just came from being hyper-competitive. In a way, my hyper-competitiveness made me view everything as a zero-sum game. So, somebody else’s win was my loss. And in my 20s and 30s, I think it was a process of reframing things of, okay, like the world is incredibly expansive and somebody else is winning in my experience and the reality of my experience is usually also a win for me too because they’re my friends. I know them. I really do believe in the rising tide lifting all boats. And so, yeah, there is certainly some maybe to your point about the Neanderthal brain of like, okay, zero-sum, this person gets to eat means I don’t get to eat. But generally speaking, when we’re talking about the things we’re talking about, business opportunities, monetary opportunities, there is just so much of it out there that I in no way believe that somebody else’s win is my loss. And in fact, I believe kind of the opposite, and I’m inspired. I’m inspired by you saying, okay, my business is doing well. I moved to Puerto Rico. You know, this is a wonderful thing and so I want that to be celebrated and I think that creates a culture not just that’s positive but of opportunity. If I see what’s possible for you, I know what’s possible for me. 

Hilary Hendershott: It does kind of feel like in the gender-based ways that we’re talking about where it’s different for women than men, it does kind of feel like the last vestiges of patriarchy. And I’ve said before on this show, sometimes women are the most guilty of beating each other down with that caveman bat. So, you’ve talked about this term, the ambition penalties so we’re still in the same vein. How do you define the ambition penalty and where do you see it in your own life? 

Stefanie O’Connell: Yeah. So, it’s hard for me to define it because I have spent so much time getting into the nitty-gritty of the research that kind of made me come up with this term. But basically, the idea is when women express their ambition or take action on their ambition, whether it’s to pursue a leadership role or advance in their careers or ask for a raise, there is generally some kind of push back that results in a tangible penalty, whether it’s a rescinded job offer, whether it’s a loss of social capital and therefore being labeled unlikable, which can then manifest in being passed over for future promotional opportunities, which can manifest in being more likely to be denied a raise. So, these are just some of the scientific things that have been studied, just showing, especially for women of color. When they do ask for a raise, they are less likely than equivalently successful, equivalently performative men, white men, to get the raises they’ve requested. And so, really what I’m trying to get at with this idea of the ambition penalty is that so much of what we tell women and understandably so to close things like the wage gap or the wealth gap is to ask for more, to lean in, and to do these things. And, yes, that stuff is important. 

But I think what I’m getting at with the ambition penalty is saying it’s actually a little bit more complicated because the fact is we are trying to do these things like ask for more in advance and seek leadership positions in a world that still penalizes women for their ambition no matter how much they ask, no matter what context generally they’re in. And so, I think it’s about making sure that when we talk about negotiation, we also talk about bias. We also talk about patriarchy. And to your point, both men and women perpetrate these things. So, I think it’s just about bringing more nuance to the conversation. 

Hilary Hendershott: Do you feel like you’ve been a victim of the ambition penalty? 

Stefanie O’Connell: I think I have done okay, and I think the reason why I’ve been able to skirt a lot of it is because I work for myself. So, I’ve been interviewing a lot of women who have had this experience and one of the things that really blew me away was I spoke to a lot of women who had job offers rescinded when they negotiated salaries, which is like mind-blowing to me that this is happening in 2021 and I so easily found scores of women that this happened to. 

Hilary Hendershott: Oh, my goodness. 

Stefanie O’Connell: Yeah. It’s wild. And I think what I noticed is that so much of this is really tied to traditional workplace structures, which is where most people work, which was honestly just built for and by men and even women who are successful. You know, we’re still operating within a system that rewards qualities of assertiveness and boldness and what is traditionally considered masculine, and it rewards that in men and it punishes those same qualities in women. And it’s not that we’re out here being explicit about it. Nobody’s like, “I don’t like women who are bold.” Nobody’s going to explicitly say that but those are the kinds of biases that are kind of operating under the surface unconsciously or subconsciously. And I think what I want to do is bring some of that to the surface and say the gender discrimination we see today may not be as explicit as it used to be but it doesn’t mean it isn’t there. And I think it’s important that if we’re going to have conversations about closing gaps in pay and wealth, whatever, we have to be honest about what’s happening instead of making these flawed assumptions that women are simply less interested in high-paying careers or are not asking for raises or are not staying in the workforce after they have children because a lot of what the research says just totally disproves those narratives. 

Hilary Hendershott: So, it really is about addressing both sides of the interaction, and I feel like this might be like some of us discovering that even though we don’t consider ourselves race-biased, I have friends of color yet we’ve recently discovered that we still harbor these biased thoughts or that we’re acting subconsciously in biased ways. And it’s really a horrible and painful thing to have to contemplate and it requires a ton of humility. So, what would you say to that? I mean, for example, some of the women that you interviewed who had offers rescinded for negotiating were those offers rescinded by women. 

Stefanie O’Connell: Yes, some of them were. And I know we alluded to this earlier and I do want to say it really explicitly, both men and women, anybody, or anyone of any gender identity in a system of patriarchy, everybody is operating under patriarchal norms. Like, it’s about a system of rewards and penalties more so than it is, “I’m a man doing this against a woman.” You know, it’s everybody’s enforcing and rewarding like traditionally masculine behaviors in men and generally penalizing those things in women, again, not explicitly but these like the implicit biases that are just in the systems we’ve built over time. And this is not me saying like, “Shame on anybody.” I do it. You do it. We all do it. We’re not trying to do it. But we just have to understand that this is the way that we’ve grown up. We’ve been socialized kind of like the milestones things, right? Like we grow up knowing how to respond to what happens when somebody gets engaged or gets pregnant. We don’t necessarily have a script for everything else. And I think that’s how we need to think about this when we’re talking about women’s ambition, particularly for women of color. Like, yeah, what do I need to do better to make sure that these biases that I might not be aware of but clearly are happening because these patterns continue to show up in both anecdotal evidence and in research-based evidence that like what am I doing that’s like perpetrating this and what can I do differently? 

Hilary Hendershott: Right. And so, I don’t mean to oversimplify the issue but I want to ask you if you want to go one step further, do you have a recommended prescription? Are there solutions that you know about other than just admitting it, talking about it, getting out in the open? 

Stefanie O’Connell: Yeah. So, it’s so, so difficult to be prescriptive when it comes to anything that’s so hugely systemic and problematic. But what I will say is that in speaking to people about their own experience, I think one of the things that really struck me as I was interviewing one of the women who had her job offer rescinded after a negotiation, and she said, “You know, everybody says that the worst you can hear is no in a negotiation but the reality is the worst they can do is gaslight you, demean you, tell you you don’t have the skills and experience that you do, give you imposter syndrome that you never had before, hurt your confidence,” and that really struck me. That really struck me because I thought about the narratives that I have even kind of perpetrated as somebody who’s like, “Don’t let anybody tell you what to do. You do you.” And I think part of this and again this isn’t like super prescriptive but I think it’s just really thinking critically about the way we move forward is part of it is me and all of us being like, “Oh, wait. How can I take whatever I’m saying, whatever I’m saying about negotiation, whatever I’m saying about how to show up in the workplace, however I’m speaking to women, and take the reality of these experiences and these biases that are still hurting people into account?” 

And so, instead of just assuming that a woman like this is just born with imposter syndrome, it’s like inherent to her, what if instead of like assuming that, I reframe the assumption as, “Oh, this confidence issue, this imposter syndrome is a result of workplace trauma. It is a result of lived experience. It is a natural response to the way she has been treated.” And that reframes the way I am speaking to that woman, not as someone saying just, “Who cares what anybody says? You do you.” Well, actually no. That’s actually not great advice because, at the end of the day, there are people whose biases are going to affect you and what is possible for you, and what opportunities are available to you. So, one thing that came up for this woman was like, okay, how do we recognize earlier on in the interview process whether this is an environment where your ambition is going to be rewarded or whether your ambition is going to be penalized? Because obviously, she doesn’t want to work in an environment where a job offer is going to get rescinded when she tries to negotiate salary. But it’s pretty crushing to go through eight rounds of interviews and really invest yourself in this potential future and then to learn that. 

So, what are some of the signs I can look out for sooner to recognize an environment where I’m not going to be championed? Can I go on to LinkedIn and see whether that company is really committed to their diversity, equity, and inclusion statement that they put on the front page of their website? Like, is their leadership team reflective of what they say their values are? Are there people like me in that company? So, I think that’s kind of a little bit of what I’ve been learning throughout this process is like it’s really not on individuals to solve for these systemic problems but by us, individuals, being aware of them, maybe we can learn how to protect ourselves, how to better navigate, how to have better conversations around these things. And then when we do have positions of power, can we advocate for the other people in the room? 

Hilary Hendershott: The you-do-you type coaching, it can be confidence-building but, of course, it can’t be universal because some community has to accept you, otherwise, you’re sitting on a rock precipice by yourself, right? 

Stefanie O’Connell: Exactly. 

Hilary Hendershott: You have to find your people. 

Stefanie O’Connell: Yeah. That’s well said. And that’s kind of what I’m getting at. And as you can probably tell as I’ve been talking about this, I’ve been researching this for two years but I’ve only started to publish and speak on podcasts about it in the last couple of months. So, I’m still figuring it out because it’s really complicated and it’s really messy. And I allow myself to talk about it without the perfect talking points because I think that’s important that it is a little bit messy. Because this stuff is so nuanced and so often when we’re talking about advice, we’re speaking in binaries. We’re speaking with so much simplicity. And the fact is like that just doesn’t work and I’m so tired of that kind of advice and I think it’s doing us a disservice. And so, I think talking through it with you here, you clarify what I’m saying like that’s the work. That’s what we need to be doing. 

Hilary Hendershott: Well, and as a coach, I mean, I have to sometimes hold myself back from giving the Nike coaching, which I call it, Just Do It, and it’s in that same family of just do it. Well, if just do it was going to work for her, the person I’m coaching, maybe she would have done it 10 weeks ago or whatever. And I do think, I mean, let me just say that even my family has related to me like I’m competitive and they use the word competitive and what they don’t say is that there’s something wrong with that. It comes with like this disdain or this eye roll, “Oh, well, that’s just Hilary. She’s just being competitive.” And I feel almost gaslit. It’s like how do you respond to that? Because I hear what you’re saying and I can respond to what you’re saying but it’s tough for me to respond to what you’re not saying and I do feel hurt. I feel judged and rejected. And competitiveness is part of my nature. 

Stefanie O’Connell: And there’s a real cost to that. We always say, “Oh, okay, so ambitious, competitive women are unlikable. Big deal,” but actually, no. It’s not just being labeled unlikable or difficult to work with or whatever else people want to either imply or say outright about us. It has very real consequences and costs. And that is not right. Ambition and competitiveness and boldness, assertiveness, these are all qualities that are rewarded in men. The only reason they are penalized is if they are in women, and that is nothing but sexism. And like it is not me saying we don’t like women but that is what people are effectively saying and it is just as destructive as being explicit. 

Hilary Hendershott: So, let’s talk about it because we have a lot of entrepreneurs listening to this show and I think it’s interesting that you said you’ve been able to skirt the issue personally to a large extent because you work for yourself. And I think as a self-employed person, you do have the opportunity to create your own community. You determine your team. Once you get to a level of success, you can even say no to customers, right? “No, I don’t want to work for you.” What are the lessons about what you’re discovering about the ambition penalty that apply to business owners? 

Stefanie O’Connell: That’s a good question. I do think this is probably true for people who work in traditional jobs as well. But certainly, as a business owner who has clients, that’s basically what allows me to be in business. I think the thing that makes my ambition palatable is that I’m using it in service of the goals and objectives of my client. And so, if I can frame what is interesting, what is good for me through the bottom line of somebody else, then, yeah, like how can they argue with that? If my ambition makes them have better results, make more money, win, be successful, then that’s a win for them too. So, it’s unfortunate that we would even have to think of it that way, that the ambition wouldn’t just be an inherent good because as long as you’re not cutting people down for the sake of your own ambition, I have no problem with however ambitious somebody is. I think it’s a great thing. But unfortunately, part of this conversation is just recognizing that this bias exists. And so, we are all navigating this world in which this bias exists. So, what do we do is like, okay, it has to become an asset. And since most people don’t see it as an asset, well, how do we frame it that way for them? We frame it that way for them by defining our ambition through their communal benefit, their net win. And you can do this in the workplace, too.  It’s when you wind up advocating for yourself, you don’t use the “I” language. You use the “we” language or the “you” language. What are you doing for the company’s bottom line? How are you improving metrics and results for them, even if you’re the one doing it, even if it serves your own ambition? At the end of the day, if you can frame it in those communal terms, that is more palatable. 

Hilary Hendershott: Yeah. It’s interesting and that circles the conversation back to the topic you and I love so much, which is money, which tends to be the universal pacifier. I did have a client one time and it was a male, a man. He said to me something like, “You’re competing with this other person who’s also bidding for the job but I’m going to pick you because you’re more ambitious.” And so, there was something about my ambition that I was able to translate to, “Hilary’s going to work her butt off so that I’m successful.” And I thought, “Well, there’s a good fit for it but that’s where it works.” Let’s transition just a little bit. I want to talk about, because the ambition is closely related to confidence and you, I’ve always thought of all the entrepreneurs I know the nature of what you do and how you do it is you have to hustle. You have to advocate for yourself a lot. You know, you’re in a more sort of cutthroat kind of industry than I am, I think. And in every career, success builds on success but I think you have to advocate for yourself every day, probably. Tell me, where do you find your confidence? What are the things that build your confidence most? What’s your most successful tactics? 

Stefanie O’Connell: I think, for me, I am very unafraid of being rejected and that is a superpower. It feels a little bit trite to say it because like everybody talks about rejection all the time. And I don’t want to fetishize rejection because I think that’s the flip side of the coin. Sometimes there’s like this obsession with like, “Get rejected. Fail. Fail fast,” and I understand the sentiment of that but I do think the messaging gets a little bit perverted sometimes. The goal is not to be rejected. The goal is to win but like to win, the rejection’s part of the process. And that’s kind of how I always frame it is like I know I’m going to get a lot of nos before I get a yes but I have to get the nos to get to the yes. So, I think that framework has always served me because I know that like, “Okay. It’s not this one.” Then I’m like, “Okay. One step closer. One no closer to my yes.” And that helps me think of the rejection not as a kind of like finality but just as like a stepping stone to where I need to get to go next. Now, I will say one thing I thought about a lot during the pandemic was how do you know when the no is a sign to just keep going that it’s a stepping stone or that it’s a sign that you need to pivot and change something? Like, do you pivot or do you double down? And that’s a really hard question. Not saying I have an answer to it. 

Hilary Hendershott: Or it’s not science. 

Stefanie O’Connell: Yeah. Exactly. But that’s where I think community really comes in handy, having people around me who give me really honest feedback. I am also realizing I had a lot of realizations during the pandemic, one of which it’s very hard to find people who are willing to be honest with you and who are willing to give you feedback that is constructive and critical. And I think the combination of how I think about rejection and having a trusted group that does that for me has been like just I literally couldn’t do what I do without it. 

Hilary Hendershott: So, do you have a constructive criticism group? 

Stefanie O’Connell: I do. We meet every week and one of whom is my business partner on this event that I host. So, it started just the two of us and it has grown. I don’t know, it’s so refreshing to hear how other people perceive your work no matter if it’s good or bad what the response is as long as it feels honest because it is so impossible I think everyone who’s creating work to get out of your own head and how you see it. 

Hilary Hendershott: Yes. You don’t have an unbiased view of your own work product. 

Stefanie O’Connell: Exactly. And there’s just so much somebody can bring to see the disconnect sometimes between your work and then how they know you as a person. And I think that is like insanely valuable. I mean, obviously, you’re somebody who coaches so this is something you can offer too. I think one of the things that has been really helpful about having a group of people who I do this with is we’re also friends. So, it’s wonderful. 

Hilary Hendershott: Still, huh? 

Stefanie O’Connell: Yeah. It’s wonderful to have people who know you to understand you as a person and your values. And then how does that translate into your work product and how much you will say how much of it you do or don’t want to be in your work product. And then they can be like, “Well, you’re not showing up as that at all.” And you want to be willing to be able to take that and that can be hard. 

Hilary Hendershott: But take something. 

Stefanie O’Connell: Yeah. But having that group that I implicitly trust and I know has my best interests at heart, that makes however harsh the feedback totally fine to take because then they’re going to support me as I try to figure out what that next step is. So, I’d say like those two things have been kind of my “secret sauce” for being able to continue as an entrepreneur. 

Hilary Hendershott: So, now, I’m super curious about this thing. So, just really quick, do you present some work product or ask them to evaluate a video or a blog, something you’ve done recently, and then is there a framework for their feedback? 

Stefanie O’Connell: So, it’s very unstructured because the relationship is very blurry. It’s based on friendship but it’s also people who are in a similar space. We all have different kinds of businesses but we all do somewhat similar things. So, if let’s say I’m working on an article and I’m like, “I’m stuck,” I can send it to them and they’re like, “Okay.” They can give me line-by-line edits. They can say, “This doesn’t make any sense whatsoever.” They say, “Oh, this actually doesn’t fit in alignment with anything that you said you were trying to do right now in your business.” Good example. We were talking a couple of weeks ago about social media and just like the enormous brain drain and like a life drain and energy drain that it is for all of us. And I was like, “You know what, I feel like not having as big a social presence as I want is really holding me back from like when I do publish a podcast or do publish an article, it doesn’t get the traction I wanted to because I haven’t built the social following. So, I feel like I should double down on building the social following. And then one of my friends in the group said, “Stefanie, that’s totally legitimate but think about the opportunity cost of your time and energy.” I’m somebody who’s very tired all the time. I have very poor focus, really bad ADHD. I get maybe two hours of work done in a day, maybe. 

So, for me, she made me think of it through the framework of like, “If you are going to take your precious two quality work hours a day and spend it on social media, what are you giving up in doing that?” And I was like, “Oh, well, maybe pitching an article that goes to Bloomberg that then kind of goes maybe viral,” which is what happened with my ambition penalty piece. So, it was like even though my social following I would like to be bigger, at the end of the day, I would rather be taking my precious two hours a day and spending it on pitching and writing pieces that I think have viral potential and I think are really well-researched, and I think really reflective kind of work product I want to be creating at the end of the day. So, that’s the kind of conversation that happens. 

Hilary Hendershott: That sounds amazing. And, yeah, you have to have a lot of courage and confidence to participate in a group like that and a lot of like partition, like you’re in this room now and then later we’re friends, we’re having a glass of wine, and you probably don’t have permission to say stuff like that to me after my second glass of wine. 

Stefanie O’Connell: I will say the group has changed over time. It has evolved like with new people, people coming and going. It’s not for everybody. So, I think it’s also about being willing to play with the structure. I have been in so many feedback groups over the years and this is the one that has stuck and it’s iterative. I don’t have like the perfect structure or solution for any of it but I think just like being willing to be honest with people and find like either it feels right or it doesn’t, and being willing to listen to that, that goes a long way. 

Hilary Hendershott: Well, given you are only going to work two hours today, apparently, I thank you for spending part of one of those hours with us. There is a question I really want to ask you so I promise to wrap up after this. You had published that during the pandemic you had to renegotiate I think an apartment lease, I assume to lower overhead, and then recently that you hired four people to work in your business. So, I’m perceiving there was a turnaround. To what do you attribute the pivot? Tell us about that story. 

Stefanie O’Connell: Yeah. So, at the beginning of the pandemic, like everybody, there was just so much uncertainty and confusion in my business but also in my household. 

Hilary Hendershott: It was scary. 

Stefanie O’Connell: It was terrifying for absolutely everybody, right? It’s like something big is happening. We don’t know the implications and we don’t know how long it will last. Good luck. So, one of the very scary things is my husband is a Broadway stagehand. So, his last day of work was March 12, 2020. He went back to the theater this week in August 2021 for the first time. And that is still part-time. The show doesn’t open until October 2021. So, we obviously did not know that it was going to be a year-and-a-half of him not having work but it was jarring in that moment, even with a four-week shutdown. At the same time, in the four weeks of the initial shutdown, I lost about $100,000 in projected revenue because I had a lot of video shoots scheduled out for the rest of the year. They were all canceled. And it was just completely disorienting. Like for everybody, everyone had their own version of being disoriented. This was my version of being disoriented. So, we went from my husband losing his job and me basically losing all my revenue in four weeks. And we were like, “Okay. We have emergency fund savings but there is so much uncertainty that I don’t know how long it needs to last.” I had more than six months of emergency savings but I didn’t have like three years’ worth and it’s already at this point been a year-and-a-half. 

So, when we got about three or four months into the pandemic, I started trying to renegotiate with our landlords. I started like really just thinking really critically about what do we like drastically need to change. I think initially we were like, “Okay. We’re cutting out all our nonessentials,” but then housing is still an essential. So, then the next step was, “Okay. Our housing might be essential but our Manhattan apartment is not essential. The Manhattan apartment version of our housing is not essential.” So, that’s kind of when we went into phase two. And then phase three was the fall of 2020 and I think I can’t say that it was something I really did differently so much as that businesses started spending money again and they started bringing their media budgets back and their ad budgets back. And I have been working like a fiend ever since. 

Hilary Hendershott: I bet. I was going to call you a hustler. I wasn’t sure if that would offend you, 

Stefanie O’Connell: Not at all. Not at all. But now it’s funny because I’ve been like I worked like nonstop from September last year to July of this summer and I am exhausted. Like a lot of people, I’m in a little bit of a burnout mode, which is unusual for me because I am pretty good about managing my balance. But I’ve had a little bit of like the scarcity mindset now of like, man, we were positioned as basically as good as it gets. We had tons of savings, dual-income, dual-high incomes, everything, and it still felt like the bottom fell out from under us. Even though we were okay, it just was emotionally scarring. And I’m still kind of grappling with building up the fact that, hey, your systems worked as they were designed to work. Your emergency fund worked as it was designed to work. You need to just rebuild and trust. But it’s hard. It’s really hard. 

Hilary Hendershott: I have said surrounding yourself with cash can truly be a panacea. So, congrats on lowering your expenses and having that curveball account or emergency savings. Stefanie, thank you for joining us. I appreciate your time. Where can people find you? 

Stefanie O’Connell: I’m at StefanieOConnell.com and the podcast is called Money Confidential. 

Hilary Hendershott: Money Confidential. Great. Thank you, Stefanie. 

Stefanie O’Connell: Thank you.



Hendershott Wealth Management, LLC and Profit Boss® Radio do not make specific investment recommendations on Profit Boss® Radio or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.


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