SPEAKER_00 0:03

Hello, I'm Jamie Lee. I'm an executive coach for smart women who don't like office politics. And I help them get promoted and better paid without throwing anyone under the bus. How? By blending proven communication strategies with brain-shifting neuroscience techniques. In this podcast, we explore the stories and strategies of gutsy women who've braved speaking up and navigated their careers forward. We're here to de-risk the conversations that feel the most daunting, advocating for yourself and your growth. Let's dive in. And one of the riskiest conversations that we haven't, you know, yet fully had is how corporate America is crushing senior-level mothers. The pressures of the workplace has intensified, and so has parenting. And many of my clients, many of people who are listening to this podcast are working parents. And to address that and to talk about it, I have the awesome privilege of having Shailen Gupta back on the podcast. Welcome, Shaylene.

SPEAKER_01 1:12

Jamie, thank you so much for having me. I love everything you do, and it's such an honor to be here.

SPEAKER_00 1:17

I love everything to YouTube too. Shailen was on the podcast. You could check out episode 72, where we discussed her great and powerful book, The Cycle Confronting the Pain of Periods and PMDD. Shailen is also a staff editor at Fast Company on their work life and leadership verticals. And she also co-authored The Power of Trust, and her work has appeared in The Atlantic, ESPN, Fortune, Harvard Business Review, and Time. She holds an MS from Columbia Journalism School and a BA in creative writing and psychology from Johns Hopkins University. And she's also been a Fulbright Grant recipient. Very bright, very smart, very accomplished. Thank you for creating time to be on risky conversations. So I asked Shailen to come back to the podcast because Shailen recently published this groundbreaking article. I think the article is riveting, it's eye-opening, it's powerful. And the title is a little sobering. Corporate America is crushing senior level mothers. Here's how they're coping. So I'm just gonna read a quick excerpt from the article. And of course, everyone should go read it. Uh, subscribe to Fast Company. You can subscribe for as little as a dollar for the first month, I found out. And here's a quick excerpt. It's been a bad time for working women. Last year, men joined the workforce at three times the rate of women. Meanwhile, more than 455,000 women, that's close to half a million women, left the workforce just between January and August. So that wasn't even the full year. And almost half cited caregiving is the reason. Lean in and looking as Munkensey's Women in the Workplace report found that 60% of senior-level women reported burning out compared with about 50% of men. And two researchers at Ruckhurst University found that caregiving strain is the largest predictor of burnout and leaving a job, especially among women who are 10 to 15 years into their careers. The girl boss is out and the power pause is in. I love that line because previously we talked about the power pause, you know, but now it's the power pause. So, Sheilen, I'd love to hear your thoughts. You know, you put out a call on LinkedIn, and I remember seeing it live when I was scrolling on LinkedIn. I saw your call on LinkedIn asking for stories, and you got over a hundred responses. And in the article, you noted that that was that was more than 48,000 words, the length of a short mystery novel. And what for you was the biggest surprise, or perhaps the pattern that emerged from reading, assessing these more than 100 responses from working mothers who are feeling the pressures of work and parenting.

SPEAKER_01 4:31

Well, first of all, I have to say, Jamie, I walk into the story really nervous. First of all, I was afraid nobody would talk to me that senior-level women didn't want to open up about their families. That was not the case. But second of all, I was wondering if I had grabbed the wrong end of the stick. Because senior level women, I imagine, have power, they've got resources, and they have access to things that the regular working mothers don't have. So I imagine, like, would they even have problems? And I figured this would be kind of a very typical article. And in fact, after I put out my call on LinkedIn, one of the first messages I got was from a man who was a senior-level board leader in a prominent organization that I really respect. And he actually did say, Shalen, you know, I think you maybe should rethink this article. Senior level women don't have any issues. It's it's the regular working mom. But by the time he was finished with that, my inbox was exploding. I had so many messages coming in. I was watching this mess, this LinkedIn post essentially go viral on LinkedIn, and comments were pouring in. I couldn't keep up. And even though I hadn't been able to get through the bulk of it, I could say, well, I beg to differ. They certainly have a lot to say, and there's a lot going on. And then, you know, I read through the comments, and the premise of my article when I were when I first thought about it was this idea that, you know, these are women at the top of their game. It is really hard to break in as a woman in corporate America, right? Today, the Fortune 500 just announced their list of how many female CEOs there are. It's 11%, and that's an all-time high. So, you know, these women, they're smart, they're shrewd, high EQ, high IQ, hard workers. They are the entire package. And so I figured whatever they have to say, like this wisdom is going to be helpful for all of us, and I can be the conduit in distilling it to everybody. And then I read the messages and I was like, oh my God, everyone is on fire. And all of these women were writing into me saying, I can't wait to read your article because I am struggling. But other women look like they have it together. So I want to know what they're doing. Like, what is the trick? And maybe I don't necessarily have advice for you, but I'm sure they do. And no one had answers.

SPEAKER_00 7:00

Yeah. And and I'm curious, even though no one had answers, there were many hacks, there were many resources, there were many ingenious solutions, some involving AI, several involving creative ways to negotiate or advocate for themselves. And that's what really struck me. Because that's to me, when I read the article, I'm like, oh, there is hope. Yes, the problem is intense and it seems to be getting worse, but there is hope because people come up with solutions. And I'm curious for you, after you know, you read the 100 plus responses and you selected some some some of the stories to showcase in the article. Did anyone really stick with you?

SPEAKER_01 7:45

Yeah, and Jamie, thank you so much for making that point. I do want to say, well, everyone was mentioning that they were struggling. Right. A lot of people had very creative solutions. And I would I do want to point out there's a difference between like figuring out how to cope in a broken system versus like being in a broken system. And so that's an important distinction where the system is broken, but there are people with really, really creative solutions. You know, I was all of the people who wrote into me, right? Even though they felt like they're on fire, at some level they are making it work because they're holding on to their jobs and they have kids. And so it ranged from some of them I felt, some of these coping strategies and hacks I felt like reflected the kind of dystopia we're in. Somewhat, like a number of people wrote to me about using AI. And some of it was, you know, using AI to figure out the mental load, you're getting a ton of emails from daycare, have an AI agent kind of scan and figure out what's most important. And then there was, there were things like well, I have AI generate a bedtime story and read it in my AI-generated voice when I'm away on business trips and I miss my kids, which to me felt like I entirely missed the point of spending time with your children. There were ones where someone brought her child to meetings with the idea that this is a great training ground and great for their future. And, you know, when you when we when you really unpack that, you know, and she was able to make it work. And it sounded like it was this great, it ended up being like a great conversation where her child comes to meetings and the team gets a younger person's perspective. But should we be normalizing that? You know, can can't children just like at what age do we start having to worry about attending job, you know, about our careers and being savvy? And at what point do you want like you're gonna spend your entire life in meetings? Now we have to spend your childhood in meetings too, as well, you know, learning to be professional and learning to be quiet. And I'm sure this child will have a wonderful leg up at the job market, in the job market, but but is that that important? There were people who gave their children toy laptops and trained them to work alongside them. So it's like you do work while mommy does work. Um and to me, it just sort of begged the question of what are we living for? What is what is the most important in our lives?

SPEAKER_00 10:12

You know, when you say that, it kind of brings me back to when I was a little kid. I was an immigrant latchkey kid, and my parents ran a gift shop in Queens, and they were so busy. They worked, you know, around the year, literally like 364 days. And every once in a while they bring me to the store and they would give us a little pass. You know, they would like stop this shelf or like watch this register. And I remember like just feeling like really responsible at a very, very young age. Maybe I was like eight or nine. Yeah. And now now that you know, I hold all my coaching sessions on Zoom, and of course, inevitably, child like walks into the Zoom screen, or you know, they want their parents' attention. And it I have to be totally honest, it breaks my heart a little bit when the person is like, out of my Zoom screen. This is my, this is my, you know, like I'm like, oh, they can they can sit in too, you know, it's okay. And I remember when the pandemic happened, you know, this became just a very commonplace thing where because now all of a sudden we're all doing Zooms and Teams meetings, and yeah, children would just sort of, you know, flow in to our work virtual work spaces, yeah. And in fact, we'll talk about this in a bit, but you you mentioned a women-led company that just totally normalized having kids in the meetings and normalized making time for the children, right? It's a a workplace that was founded by working mothers for working mothers. So I want to hear about that company in a little bit. But some of the stories that you that were showcased in the article, again, it just gave me hope. Because, again, you know, the whole premise of this podcast is sometimes we have to have these conversations that feel risky or, you know, a little even, you know, edging on the taboo to create solutions within a broken system, right? And some of the people that were featured, take, for example, Ellie Stack and Jessica Finnig are, in my mind, kind of like working couple. They're same gender working couple. Why? Because they've been job sharing the same VP role for 13 years and they've done it across different companies. They each work three days a week. They split their commission evenly, 50-50. They cover each other's leave so that when one person has to go to their child's, you know, doctor's appointment, the other person covers for that. I thought that was just so creative and so ingenious. And that level of creativity is really remarkable. And also kind of, you know, to your point, kind of shows the dystopic side of where we are, because they have to come up with a solution because the system wasn't offering it to them. And I'm curious, what do you think this says about our workplace culture right now?

SPEAKER_01 13:15

That's a great question, Jamie. And just to clarify on the earlier part, I do want to say like there's a distinction, I think, between a kid wandering onto a Zoom call in the background versus like actually integrating your kid into a work, into a meeting, and having them sit with you, which is what one of the tips was of like bring them to your meetings, have them be an active contributor, have them listen or just take notes and learn how to participate in a meeting or just debrief with them afterwards. You know, in terms of your question about Kelly and Jessica having a really innovative solution where when Kelly Stack got pregnant, she, her friend Jessica suggested instead of just working four days a week, she and Kelly job share and split the job down the middle. So that way each of them works three days a week and then they get the other two with their families. And I think you have a really incisive point, Jamie, when you say they had to invent that solution themselves. It points to a system where, you know, over and over again, we're seeing this come up in the debate. The current working environment was not designed for a family where both parents work. And typically this means it's not designed for women because historically the man has been the primary breadwinner. And we're seeing this start to crack around the edges because today we're in an economic reality where, for a lot of families, both parents have to work. And simply also a lot of women just want to work. It means economic power and more fulfillment. They have fought for the right to work and they should have it. But now we're in the system which is not designed for that. And I think something that we tend to forget is that systems are changeable. In the beginning, like the 40-hour work week, that came across, that came about because Henry Ford decided, you know what? I think I'll get more out of and better quality work out of my employees if I give them a shorter work day. It used to be longer. The summer vacation for schools was designed because we live in an agricultural society back in the day, and parents needed their kids home to harvest. So it stands to reason. We can absolutely redesign our current system so that it works for working mothers. And indeed, daycare came about because during World War II, mothers had to go work and someone needed to take care of the children because all the men were away fighting the war.

SPEAKER_00 15:43

That's really interesting how like the each systemic evolution required a kind of well, environmental factors, but also almost a kind of a crisis. Like when you when you mentioned that daycare was invented during the World War II, it's like, oh, we're in a crisis, and all the women have to replace the men who went off to fight the war. And so we need to create this. And it almost makes you wonder do we need another crisis to come up with, you know, say, for example, work from home, remote work, and that was in response to the COVID pandemic crisis. Yeah. And hopefully, you know, it won't be as dire as that. But you know, let's go back to the story of these two women. They both acknowledge, Jessica acknowledges in the article, that even though she and Kelly they split the job evenly, they really can't like manage people. They can't really step into that people leadership position that a lot of people, a lot of ambitious senior level women aspire to do. And so that sort of shows that that ceiling they're under. And I'm curious for you, when you were reading over the responses, how much of the hundred plus responses that you got in this viral post was about sort of like accepting, like making peace with what's broken and just making the best of it. And I'm I'm curious, you know what your thoughts are about that.

SPEAKER_01 17:16

Absolutely. And yeah, to your point about Kelly and Jessica, they did say that they did manage someone and it went well. But in general, they felt like it was unfair for two people.

SPEAKER_00 17:25

Ah, so they did manage. Okay.

SPEAKER_01 17:27

They did manage one person, but they were like, this was a one-off. It went well. But in general, we felt like they felt like it was unfair to manage somebody because then you've got two bosses, two different expectations. It's a lot to coordinate. So they didn't so I believe during the interview, Jessica mentioned, like, I don't, you know, I don't know. I think we have a we might have a ceiling on how high we can go. Um I'm sorry, Jane, because your your previous question, I forgot it.

SPEAKER_00 17:50

Absolutely. So I'm curious from all of the responses you read, how much of it was about just accepting, you know, what's what feels broken? How much of it was, you know, it's not about coming up with new solutions, but was like, yeah, I mean, it's broken and we just do the best with what we have. You know, to take, for example, it's not something that you can solve with cleverness. You mentioned, for example, time blocking and meal prep. That was that was like a recurring theme. And I'm curious, you know, what your thoughts are about that.

SPEAKER_01 18:32

I feel like one of the reasons this article took off is because it said something that has been sort of creeping in people's subconscious, but they haven't voiced, which is the system is not working. And there's just this acceptance of if you want to have kids and if you want to have a job, you are just you're just gonna have to be superhuman. You're just gonna have to muscle through. You put up with the short amounts of sleep, the feeling like you're kind of on the brink of having everything fall down and just staying there madly for years. So I think working moms at all levels have just been coping, coping quietly. And here's what really bothers me thinking that it's them, that that they're struggling and they're tired and they feel like they're on the brink of everything falling down because they haven't figured it out. And if they were just a little bit smarter, they had like one more hack, it would get fixed. And the answer is no, the system simply wasn't designed for them.

SPEAKER_00 19:34

Yeah, and that's really powerful when you recognize, yeah, it's not me. This, it's the system, it's it's the the water we're swimming in. Yeah. And I think that helps to alleviate a lot of the guilt and the emotional baggage that working mothers unintentionally end up carrying, not because they're doing it wrong, not because there's something that they need to fix about themselves, but because you know, culture and gender socialization has us sort of internalizing the fault. So thank you for bringing that to our attention, to our conscious attention. And I think about you know several of my own clients whom I've had the privilege of coaching. And for some of them, like this really was, you know, while caregiving, while being a mother, and wanting to become CMO or CSO or you know, what have you, and and feeling that that friction so deeply that sometimes they just had to decide to step away from it all, you know, or or come up with solutions. So one of the other really cool solutions that were featured in the article was Mara Sykes, and she's a director of strategy for a content distribution company. And I love the story of how she creates this get to know me deck, and then she clearly spells out that, you know, these she works from nine to three, and she's always gonna ask for deadline, not because she's out to get people, but because she's playing Tetris, she's playing Allenberg Tetris as a working mother. And I I I love that level of transparency and honesty. I I saw that as a kind of self-advocacy, like preemptive self-advocacy that lets people know, oh, these are the boundaries within which you know we're going to work together. And that gives me a kind of comfort and actually helps to build trust. And and I'm curious for you, as you're reading all the responses, how did this particular hack stand out from the rest?

SPEAKER_01 21:38

It jumped out at me because I was getting about my email was about a hundred messages or so, and there's starting to be patterns, a lot of them, like meal prep. And I'm not trying to knock meal prepping, I'm not saying calendar blocking or being ruthless about your schedule are bad ways to go. They're great ways to go. They're important. They came up as like the bedrock of this is what you should be doing. So, what I was on the lookout for. were things people other people weren't mentioning, sort of what was new, because I felt like it would be kind of insulting to my audience to be saying things that they were probably already doing because they'd be like, Yeah, I know, I know I have to prioritize. And Tamara stood out because I think one other person also mentioned having just this get to know me deck and just like really putting it out there. Like this is how I do my work. And what struck me is I think a lot of people are doing what Tamara does in terms of their actual schedule and just, you know, pickup time is just blocked out on your calendar. But maybe people talking about it because there's a fear of am I going to be discriminated against? Is that going to look bad to leadership? But so many people have kids. And frankly, if we want to have more children who you know make more workers and have society continue on, we are going to need to figure out how people can be parents. And so I love that Tamra was just up front and it was just very like I am on when my kids are at school. That's the best time to get me if you want a meeting. Clearly Tamra's a high performer she's in a managerial role. And so she can just say this and she has the power. And not only that, she said that it unlocked so many different conversations for her because people saw her as a person. They saw her as more approachable. It just led her to be able to explain not just parenting but also different things about how she works, like why she likes a deadline or she also had something about being a bit more reserved in conversation because she grew up in a different country where the culture is you listen first and then ask questions. And so that sparked a lot of conversations about cultural differences and was also able to help her sort of get in front of people making assumptions about who she was and how she presented herself.

SPEAKER_00 23:48

I love that just getting in getting ahead of assumptions. And you know for some people that can feel risky just like this is who I am because for some people that can almost feel like vulnerability. I grew up in a different culture. I mean I I can relate to this story in so many different levels right I also grew up I was born into a different society and I immigrated to America and oh this is this is really great. And let's talk about for a moment something that's under the undercurrent of all of this right it's like the reality that in this moment we're recording this in mid-June 2026 policy changes have sort of come to a kind of a screeching halt to support mothers people of marginalized identities. And I like to make the argument that if you know it's not safe, it's not supportive for marginalized people, then it's not safe for all people. But like the political winds have completely you know gone in a different direction. And it seems like just as we're starting to become more aware of the efficacy and the benefits of these policy changes if now we're like you know going in a completely opposite direction. And I again I would I would like to hold on to hope but I I'm curious what your thoughts are about this because as you mentioned like if if the the system itself is not set up to support a society that can that can sustain both work and parenting like how do we sustain the society? That's like a huge question right and almost existential to society.

SPEAKER_01 25:41

I'm curious what your thoughts are about that it's a big question I know it's a really important one right because we are talking about the future and if we don't take care of our children we're not going to have a future so it's in company's best interests actually society's best interest to figure this out. But you know what Jamie the fact that you and I are having this conversation the fact that I was able to write this article and pitch it and get it approved, get internal support for this is an important topic. And then the fact that so many people read it and shared it to me shows there's a great need. We're having the conversation and once you start having the conversation change comes on its heels something that was really interesting to me is I recently got the chance to interview Gloria Steinem and it was magical. And I asked her this question too of it feels like you know we were in a moment where companies were really prioritizing diversity and equity inclusion. And then we it felt like we we took a step back. What are your thoughts on that? And she essentially pointed out there's been a pattern throughout history and she's been in this in the game of advocating for human rights and women's rights for decades. And from her perspective over time she's seen long-term changes for the better and she's like compared to when she was growing up when we talk about the amount of women in the workforce when we talk about acceptance of people of color radical changes but when you look at the micro moments you know you make step forward and then it's two steps back and then it's a step forward as you kind of in as society sort of integrates these changes into its very fiber and system.

SPEAKER_00 27:30

Yeah great great I I I you know that makes me think of how again this this hope is not just the feeling it's not just onely wishing for things it hope is active hope is an action. So let's switch gears let's talk about cakes this this really really fun company that you featured they make products for mothers and it's a company that pays $3000 monthly childcare stipend has core hours of 9 30 a.m to 3 p.m it saw 10% revenue increase zero attrition it went viral and you know they have an entire cultural ecosystem of supporting working mothers. They have protected Wednesdays no meetings on Wednesdays 30 6090 re-entry plans for parents kids allowed and welcomed on Zoom a December to January quiet period it's it feels like like the Shangri Law for working mothers I'm like all the people who want to work for a company that really supports I think I think they would all want to apply and join this company and and it feels like they didn't just solve a problem they they designed the workplace that they wanted to work at right and it's working out the revenue is growing and in fact when I was doing research for a presentation I did I found out that women led companies when compared to men founded companies their revenues are growing faster like 8% faster. So women make great investors women make great entrepreneurs and you know there's the adage that if you're at a table where you're not welcome just take your chair and go set up your own table right build your own company and several of my clients have done that and they've gone gangbusters you know and so I'm curious for you as you were you know reading the responses what are your thoughts about entrepreneurship as a solution to the intense pressures of corporate America what are your thoughts about that I don't think it's any coincidence that in the last five years we've seen the number of women entrepreneurs grow from about 25% of the pool to 50%.

SPEAKER_01 29:59

Yeah. And numerous women who wrote to me also said you know I left I took a career break or I set up shop on my own because simply it's just not it's just not possible. And I wrote another article about menopause and a number of the people who who were going through menopause as well said kind of the same thing. Like I I took a step out I set up my own thing because workplaces are also not designed for women with menopause. So absolutely number one speaking of action is hope I believe that companies like cakes right where there's just such a clear template and an intention of how do we design centering working mothers it can be done. You can build a new system. Number two though, I do want to flag that it is important for all of our systems to be thinking about everyone who's involved we lose out when we don't have working mothers when we don't have women when we don't have people of color when we don't have LGBTQ plus we lose out when we don't have diversity because companies are selling to diverse audiences and if you don't understand if you don't have those people on your staff your business is going to lose out right so it's important that the existing legacy systems do figure out how to incorporate these needs otherwise they're going to see a real collapse.

SPEAKER_00 31:19

Yeah and you know with everything going on these days with the AI you know some people call it a bubble some people call it a hype some people call it a revolution but with everything going on I I I see that some people find oh it's easier for me to find to to to build my own company using these tools so that I'm not you know on the other end of being replaced by it.

SPEAKER_01 31:52

I love that and that that makes perfect sense to me use the tool to empower yourself. Exactly use the tool to empower myself right and is there anything else that we haven't yet addressed that you would like to share about your experience as a journalist as a working woman professional you know who you know saw this post go viral and see like this deluge of uh responses is there anything else that I haven't yet asked that you would like to address I think a couple things so number one just if you are struggling it's not you the system is broken and it can be resigned redesigned something I find fascinating is that entire companies in this rush to get ahead on AI are redesigning redesigning their entire workforces. So if they can do that why can't they redesign their workforce to make it more female friendly and their systems to make it more female friendly. And number two a concern I'm having is I'm seeing you know women who are having having children and I too have a child starting to to get worried or like dismissing you know dismissing themselves and their wants even before they embark either feeling like okay I can't have a child or I can't have a job I've got to pick. And and I want to say that that's not the case. Just because it's hard doesn't mean that you shouldn't do it or that you could you should give up something that's deeply important to you and it doesn't mean that it should be done. The women in my inbox, yes, they were struggling, but all of them had found ways to make it happen. And so don't quit because you hear it's hard or that it's and don't give up on children because you hear like it's not possible. It is possible and also having more working moms in the workforce means these voices will be amplified and that you too could be part of the solution.

SPEAKER_00 33:55

And thank you so much for amplifying the voices of working mothers through this journalism through this article we really appreciate that. So to recap, I heard system is broken, it's not you and I think really taking that in will help alleviate so much of the emotional distress that working mothers feel and when we put aside when we can lessen the emotional distress we realize oh we can do a lot right and that's why just as you said just because it's hard doesn't mean that we have to give it up and I love what you said about not dismissing our wants as well as our whims because that's what for me that's what self-advocacy is about acknowledging and voicing our wants and our whims. And so when you engage in these conversations that can feel risky it can be worthwhile that's that's what I'm taking away.

SPEAKER_01 34:48

I love it Jamie as you said action is hope and all of us create the potential for change within us.

SPEAKER_00 34:55

Thank you so much for coming back to risky conversations and I look forward maybe we'll have another conversation because you're you're addressing these these core topics you know that are so that you know they're real you know like PMDD the pressures of working mothers all these issues that really like head home for us.

SPEAKER_01 35:16

So thank you again Chaylene thank you so much Jamie and looking forward to crossing paths again in the future.

SPEAKER_00 35:23

Yes thank you for joining me today on risky conversations remember everything worthwhile is on the other side of a risky conversation and when done well your self-advocacy becomes an act of service. If you're ready to de-risk your own career evolution I invite you to book a free hour long consultation at jameleecoach.com slash apply. J A M I E L E C O A C H dot com slash apply. We'll map out your custom blueprint to confidence and get you on the path to being better paid on your own terms. Let's make your next conversation the one that changes everything. Talks