This is the first story in a seven-part series looking at women’s ambitions in the years following college.

Shortly after I turned 40 I was offered a fantastic job that I didn’t take. It had all the hallmarks of the kind of job I should take, and wanted to take, but it would have also meant a dramatic change in lifestyle. For the last 15 years I’d been a freelancer and then a small-business owner. I worked from home, which meant I could be around for my two young children. When someone had strep I could be there to administer the Tylenol in between conference calls. I picked my kids up from school most days and spent a lot of afternoons with them. I had what was, in theory, an ideal setup—I got to have a job and be a physically present mother.

But my career had stalled. I was taking on the same kinds of projects at 40 that I’d been doing 10 years earlier. Lots of the people I’d worked with early on in my career now had the word “global” in their title. They were VPs, making VP money and VP decisions, while I was cramming a full work day in before 3 p.m., and then spending my afternoons picking Cheerios off of the floor.

Now, somewhat suddenly, I had an offer. I loved the company and they loved me. As the last step of the interview process I had dinner with the creative director, who was the only woman at a senior level in the organization. Over plates of pasta I asked her what I hadn’t felt comfortable asking the men who ran the company: How flexible are the hours?

“They’re not,” she said. After seven years, the company leaders had begrudgingly allowed her to work from home on Fridays, she told me. It was a tech company. Twelve-hour days were the norm.

I couldn’t do it. And in the weeks that followed I sunk into a crisis of sorts. I spent lots of time reflecting back on my life, looking at the choices I’d made that had gotten me to this very point, and wondering exactly when it had all gotten so hard. I’d be walking to the grocery store and think, maybe I should move to Vermont and grow hydroponic tomatoes. Watching my kids play at the playground I’d think, maybe I should have gone to film school, or med school, or gotten a Ph.D. in political science. Heading to the dry cleaner I remembered my 10-second fascination with emerging markets and wondered, was leaving the huge consulting firm all those years ago a mistake?

At the same time, the conversation about leaning in and leaning out and having it all and opting out had reached hurricane-like proportions in the media. Marissa Mayer had recently been appointed CEO of Yahoo, only to banish working remotely. Sheryl Sandberg was exhorting everyone to step up their game, which I was trying to do, but felt I was falling short. Anne-Marie Slaughter’s story about how she’d needed to scale back (into a career that most mortal women would see as a leaned-in, overachieving one) had zinged around the internet and was more proof that all of it was impossible. And one study after another found that women lack confidence, struggle to break into management, and are increasingly dropping out of the workforce as they hit the apex of their careers.

I recalled a conversation I’d had in college. It was shortly after Bill Clinton had been elected, and my friends and I were claiming cabinet positions for ourselves in a hypothetical administration of the future. One would be the head of Health and Human Services, another was going to run the Justice Department. Someone else wanted to be the White House Communications Director. We believed, for just a moment, that if we worked hard enough we’d all be hanging out together in the Oval Office.  (We also had no idea that two decades later we would watch a woman who believed the same thing fail in her own attempt to reach the Oval.) It had been a while since I’d talked to most of those women; I was in occasional touch with a few. I knew that none of them were in the cabinet, but what had become of them? Were they also finding life to be infinitely more complex than we’d anticipated back in college? Or was it just me?

* * *

I had known, as a college student, that being a working mother was going to be challenging. It was hard to miss. Arlie Hochschild’s book The Second Shift had come out a few years earlier, and I’d read it like an instruction manual. Step one: Marry a husband who will participate in the housework and child-rearing. Step two: Be okay with a house that is a little messy and don’t criticize the husband for not doing things the way you would do them. Step three: Don’t have a way of doing things in the first place. I determined early on that I wouldn’t care about decorating, cooking, or plants. I didn’t get married until I had a solidly established career, and my husband was an engaged parent who prioritized childcare and housework at more or less the same level I did. And yet, I was still stuck.

Thinking back on that college conversation, I emailed one of the women who had been there: Elizabeth Wallace. We’d been in touch on and off since college, and I knew from our semi-annual drinks that she had been suffering her own career crisis. As a print-magazine editor, her industry had collapsed, her fast-track career had been derailed, and she was spending more time at home with her kids—which she loved. But was she supposed to love it? And what about her work? Without a big career was she worth less? And financially how were she and her partner going to survive without two incomes?

Out of that conversation grew this project, which we call The Ambition Interviews. We wanted to find those women from college and find out what had happened in the years since. Had they become the people they’d dreamt of being when they were 21? Who were they now?

* * *

We began by interviewing the women from that initial conversation about the hypothetical cabinet of the future, and quickly realized that we wanted to hear more stories. Elizabeth and I had been in the same sorority at Northwestern University, and ultimately we decided to interview everyone from our sorority’s class of 1993. The sorority provided a closed data set, and was also a group of women we’d known well in college whom we thought would be willing to tell us about their lives.

We anticipate some eye-rolling from many readers at the mention of a sorority, but let me explain: Sororities at Northwestern at the time (and possibly still today) bore little resemblance to their more notorious counterparts at other schools. That is, there was no hazing and a lot of studying. We were women who had achieved academic success in high school, and who were for the most part surprised to find themselves wearing Greek letters. For most of us the sorority was a way to find a home in a large school, a way to make friends and feel a sense of belonging.

The group was also economically diverse. Several of the women received financial aid for their sorority dues and worried during the course of their college careers that they might have to drop out because they couldn’t pay for school. Some women came from well-off families, and many were also from working-class backgrounds. One woman was the first in her family to go to college. Two were first-generation Americans.

What the sorority was not was racially diverse. As with many universities, Northwestern has an entirely separate system of, per the university website, “historically African-American fraternities and sororities.”

So while we knew we wouldn’t be capturing life and career trajectories representative of a broad swath of the American experience for women, we were interested in digging deep into this particular socioeconomic slice. These were women who excelled in high school, most coming from small towns across the Midwest, with a few East and West Coasters thrown in the mix, and had graduated from a top university with dreams that ranged from becoming “the best prosecuting attorney the world had ever seen,” as one of them later put it, to a Wall Street-inspired career in business. They were arguably some of the best and the brightest—so what had become of them? And what could their stories tell us about the experiences of this generation of women? We decided to find out.

A year later, Elizabeth and I have interviewed 37 of the 40 sorority sisters who graduated with us in 1993, two over email, and the rest over Skype. (We were unable to locate one, and two were too busy to sit for an interview.) We asked them about their trajectories since college, their successes and their challenges, and what they thought their college-age selves would think about the way things had turned out. And while some findings were expected, others surprised us. The group continued to be ambitious post-graduation, with three-quarters earning graduate degrees (M.B.A.s were most popular, followed by JDs). And they’re geographically diverse, spanning four countries, 18 states and the District of Columbia. The majority of them work either full or part time; about a fifth are stay-at-home mothers. Almost half of the working women with a spouse are either the equal or bigger wage earner. Six (20 percent) are the sole or primary wage earner, with spouses who are the primary caregiver.

Our most striking finding: Every woman in the group followed a near-identical trajectory up until the point she had her first child. After graduation in 1993, all the women went on to either land a first job or pursue a graduate degree. Due to the dismal economic climate, a few people moved back home and worked in unpaid internships until they found a job. A cluster of women went into banking, finance and management consulting; others found work in PR or advertising; and a third group headed to medical school, law school, and assorted master’s-degree programs. Throughout the ’90s the women earned promotions, changed careers, finished graduate programs, or headed back to graduate school. They also got married (all but four are married or partnered). Eight married their college boyfriends. Others met future spouses at work or in bars or on blind dates. Everyone continued to climb up, despite the rough economic start of the early ’90s, and make their way to higher-status jobs with bigger salaries and bigger responsibilities. Two of the lawyers made partner while a third went to work for the Justice Department, a screenwriter watched an A-list movie star claim the lead in her first screenplay, an ad exec earned a promotion to Associate Creative Director, and others made their way up the corporate ladder at large banks and consulting firms.

And then, beginning 10 years after graduation, nearly all of the married women began having children. For one group, motherhood had no obvious impact on their career. They continued along the path they’d always seen for themselves. One was later laid off and a second chose to leave work after her fourth child was born, but the remainder became what we call our High Achiever group. These 11 women are C-level or C-suite-adjacent executives (they describe their office as “down the hall from the CEO”), are recognized in their chosen field, or manage large teams. Many of the women in this group described their job as “big.” Among this group is the CMO of a mid-sized banking group, a prominent screenwriter, an accomplished physician at a big university hospital, the owner of a successful PR firm, and a senior rabbi at a large congregation.

For another group—14 women—motherhood was an abrupt end to the careers they’d been pursuing. This group, our Opt Outers, left work immediately after their first child was born, though only two of them had planned to. Many were on maternity leave, with daycare or a nanny lined up, and found that they simply couldn’t bring themselves to leave their child with someone else. Others asked their employers for flexible schedules, were turned down, and quit. Many said that they’d done the working-mother-cost-benefit analysis and the math just wasn’t on the side of their careers—their spouses earned more than they did, daycare or a nanny would eat up a sizable chunk of their earnings, and therefore the reasonable thing to do was to leave work and become a full-time caregiver. Some simply didn’t like their jobs, had spouses who could support the family, and decided to stay home. Today the majority of them have been out of the workforce for an extended period of time, though some take on occasional part-time work.

The remaining group—16 women—continued working but chose to move into jobs that allowed them some schedule flexibility, or stayed at jobs that let them leave early enough to be home for the school bus in some cases, dinner in others, or to work from home some days. We’re calling this group the Scale Backers. A pediatrician began job-sharing with another physician so she could be home with her children two days a week. A sales-training executive whose husband had been a stay-at-home-dad decided her job was too stressful, quit, moved to a cheaper city, and now sells crafts and art on Etsy. This group also includes two women without children who opted for more balanced lives: One left her long career at a major computer company for a job that would allow her to work from home in the Rocky Mountains and spend more time volunteering. A second quit her management-consulting job to become a life coach.

* * *

When we first took this project on, we had no idea that we would be sharing our findings on the heels of the 2016 presidential election results. We didn’t know that sexism, misogyny, and sexual harassment would become hourly topics of discussion across social media and around the globe. But the outcome of the election makes exploring these issues more important and relevant than ever. For the world to finally see a woman sitting in the Oval Office, for women to dominate a cabinet list rather than be excluded, for the Supreme Court to meet Ruth Bader Ginsburg’s definition of “enough women,” we believe that the first step is to understand what women’s lives are really like. So we are starting with this group of women we once knew well.

We’ll be looking at these three groups and the trajectories of these women in depth. We’ve identified three distinct paths that these women followed, but we plan on digging deep to uncover the choices they made and the factors that led the women to become High Achievers, Scale Backers, or Opt Outers. We’re also interested in illustrating what it feels like to be in each of these groups. Women in all three groups shared their personal joys and disappointments with us. They talked about the things they’d hoped to accomplish, what they were proud of, what they regretted, and times when life had simply gone in a random and unpredictable direction. In this series, we write about the changing meaning of ambition, the near-lethal combination of modern parenting and a 24/7 work culture, what sexism in the workplace does and doesn’t look like, and ultimately why these women made the choices they did, and what factors could have helped make their lives—and decisions—easier.


Elizabeth Wallace contributed to the reporting and writing of this essay. Read the next piece in this series here.