The Ambition Penalty: Why Working Moms Still Struggle to Get Ahead

When I sat down with Stefanie O’Connell, award-winning journalist and author of The Ambition Penalty, I wanted to unpack the assumptions surrounding career advancement for women, especially moms.
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Stefanie’s work focuses on workplace inequality, and one of the first things she challenged in our conversation was the story we have all been told for years. “We have these myths and misconceptions,” she said. “Like women just aren’t confident, or they aren’t interested in high-paying careers or leadership roles. And yet the data does not support that in any meaningful way.” That insight reframes the problem entirely. This is not about women lacking ambition or drive. It is about how that ambition is received.

From Personal Finance to a Bigger Question

Stefanie did not start her career studying workplace inequality. She began acting in theater, touring internationally and doing work she loved. But financially, it was unstable, and that pushed her to start writing about money. “I thought if I could just figure out how money works, then I could do what I love and have a life I love,” she shared.

Over time, her perspective shifted. Budgeting and saving could only go so far. “You can save a lot, you can spend less,” she explained, “but if you’re not making enough money, there’s only so much you can cut back.”

That realization led her to a deeper question. Why are women consistently earning less, even when they follow all the recommended advice? What she found was not a confidence gap. It was a consequence gap. “It wasn’t that women weren’t asking,” she said. “It was that they were punished when they did.”
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In practice, Stefanie found out that punishment does not show up as something obvious or formal. It shows up in how women are perceived and treated afterward: “The man is always perceived as being better qualified, and the woman is more likely to be perceived as not being the right fit.” Women who advocate for themselves are more likely to be labeled as difficult, not a team player, or not the right cultural fit. Instead of being rewarded, it can lead to fewer opportunities, less support, and slower advancement. Over time, those reactions shape careers in ways that are hard to trace back to a single moment, but very real in their impact.

How Small Bias Becomes a Big Gap

One of the most powerful parts of Stefanie’s research is how she explains inequality not as a single event, but as a pattern that compounds over time. For example, women often need more education to access the same roles. Their work is more likely to be undervalued. Their contributions are more easily overlooked. “Their performance is consistently undervalued,” Stefanie explained. “Men are more likely to get credit for women’s work, and women’s work is more likely to be seen as less valuable.”

What makes this especially important is how small the initial bias can be.

Stefanie described a study that simulated a corporate structure where men and women entered at the same level and performed equally. When women’s performance was undervalued by just 3%, the long-term impact was dramatic. She explained that a woman would need 17 performance review cycles to reach the executive level, while her male counterpart would need only 8. She would need to complete 208 successful projects to advance, while he would need roughly half that number.
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It is not one missed opportunity. It is thousands of extra hours over a career just to be seen as equally qualified.

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We’ve all heard it before: lean in, ask for more, be confident, build the career you want. And yet, for many women, especially mothers, something doesn’t add up. For decades, the narrative has suggested women fall behind because of their own choices. They are not confident enough, not aggressive enough, or they choose family over career.

In this episode of Trust Me Mom (Season 2, Episode 39), available on Spotify and Apple Podcasts, award-winning journalist and author Stefanie O’Connell challenges that entire framework. “We have these myths,” she explains, “like women just aren’t confident or interested in high-paying careers or leadership roles. And yet… the data does not support that in any meaningful way.” She shares compelling research showing how even a 3% bias can create massive career gaps, why women may need 17 performance review cycles compared to 8 for men, and other eye-opening findings.

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​When Progress Triggers More Bias

Another surprising insight from Stefanie’s work is that progress does not always reduce bias. In some cases, it can increase it.

Stefanie mentioned a study that analyzed about 1,500 firms, and once a woman landed a top-level job at a company, the chances of another woman being hired to a high-ranking position dropped by about 50%. “When there was a woman on the evaluation committee, men’s bias against women applicants got worse,” Stefanie explained. The presence of a woman in a position of authority appeared to trigger stronger bias among male evaluators.

Rethinking Work-Life Balance

The conversation around working mothers often centers on balance. Can women have it all? What are they willing to sacrifice?

Stefanie challenged that framing directly. “There’s a reason why debates about having it all and work-life balance are almost exclusively had among women,” she said. “It’s because men who have it all typically get it at women’s expense.”

For men, having both a career and a family is not treated as a tradeoff. It is expected. In fact, it is often rewarded. “There’s a fatherhood bonus,” Stefanie explained. “Men are rewarded when they become fathers, while mothers’ careers are more likely to stall.”

The contrast becomes even clearer when looking at time. Statistically, men consistently have more leisure time than women, even in households where both partners work. The difference is not marginal. It amounts to hundreds of additional hours per year.

The Role of Paternity Leave and Cultural Norms

One of the most telling insights Stefanie shared was about paternity leave and how cultural expectations shape behavior. There is a common assumption that men do not take parental leave because they do not want to or because it does not align with their priorities. But the research suggests something different.

“The best predictor of whether men took paternity leave was what other men did,” she said. It was not about personal preference or even family needs. It was about social norms and what was considered acceptable among peers. This highlights a broader issue. Workplace culture does not just shape women’s experiences. It also limits how men show up at home. As long as caregiving is seen as incompatible with masculinity or career ambition, the imbalance at home will continue, and that imbalance will carry over into the workplace.

The Double Bind at Work

For women, the challenge is not just about access to opportunities. It is also about how they are perceived once they are there. “There is no right way for a woman to behave in the workplace,” Stefanie said. If a woman is assertive, she risks being seen as difficult. If she is collaborative, she risks being overlooked. The same behavior that is rewarded in men can be penalized in women.

This double standard shows up across many dimensions, including age and communication style. It creates an environment where women are constantly adjusting, but never quite aligning with expectations.

Beyond Individual Solutions

For years, the dominant message to women has been to fix themselves. Be more confident. Ask for more. Lean in. More recently, a different narrative has emerged, encouraging women to step back or opt out.

Stefanie sees both approaches as limited. “They’re both selling the idea that you can self-optimize your way out of inequality,” she said. But if the system produces unequal outcomes regardless of the path, then the issue is not the individual path. It is the structure itself. “The way you change a system is with collective action,” she said. “It is not something you do alone.”

What This Means for Working Moms

As our conversation came to a close, I asked Stefanie a question that feels very real for many of us. Can a working mom actually win?

Her answer was not about choosing between career and family. It was about shifting how we think about both. “What I want people to do is live more in alignment with what they want,” she said. “And think about how they are either reinforcing the system or challenging it.” That might mean making different choices at work, at home, or in how we raise our children. It might mean questioning assumptions that have gone unchallenged for generations.
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There is no simple solution. But there is clarity in understanding that the pressure many working mothers feel is not just personal. It is structural. And recognizing that may be the first step toward changing it.