The Lost Generation

20 min read

I saw the best minds of my generation destroyed by frustration, hungry eager underemployed, driving Uber through the streets at dawn looking for a way to lean in, overeducated businesswomen burning for the promised opportunity to apply their energy to dynamic work in the machinery of the economy…


A lost generation of businesswomen is being squeezed between expectations and opportunity – between those before us, who knew they would be screwed, and those after us, for whom the problem will be fixed.

Many of us can’t find work commensurate with our education and years of experience, and we face pervasive sexism during the search and on the job.  Intersectional bias against women of a certain age is more complex than sexism alone.  For example, the gender salary gap for elite MBAs 10 years after graduation has recently been calculated (i.e., with empirical data of actual reality) as 40% — on average, we women make only 60% of what our male b-school classmates make, once we’re in our 40’s.  (But we paid the same amount for the same diploma, which when held in feminine hands loses half its value.  Imagine paying the same as me for a basket groceries, but half of the food you bought was removed from your bags as you exit the store?)

The problem arose when business schools started pumping out women in greater numbers before the business world was ready to accept us.  Top business schools started inching toward 50-50 gender ratios by Y2K (though my graduating class was anomalously only 17% women).  We believed in the vision that equal opportunity to attend school would carry forward as equal opportunity in our careers.  Now, we Generation X businesswomen have hit a wall in our late 30’s and 40’s.

Women older than us didn’t expect a fair shot. They knew they were entering a world where they weren’t welcome.  There were fewer of them to begin with, and even fewer stuck it out to the higher levels before capitulating to being shunted off into human resources, non-profits or family life.  Some succeeded – even spectacularly — despite the upstream swim.  People wishing to counter my argument will enthusiastically enumerate those exceptional women by name… because there are few enough examples such that they can be enumerated individually.

Women younger than us will probably see more opportunity by the time they spend many years in the relatively egalitarian world of junior-level work. Cognitive bias and systemic discrimination is becoming more acknowledged as a problem.  Companies are starting to realize the opportunity cost and ethical error of ignoring or underutilizing half the population.  Change begins with recruiting processes at colleges and business schools.  It seems likely that younger women will make it higher in their careers without being forced by structural sexism to damage their own resumes with job-hopping, part-time/freelance work, and family obligation gaps.

Trump has explained that the proper response to workplace sexual harassment is to quit your job and find a different one.  But when I graduated from business school, I bought into the fantasy that we elite grads were entering a post-sexist business world.  The first time I experienced a boss hitting on me, I didn’t even consider the option of masochistically damaging my career by slinking away to another job.  I tried to address the situation constructively and professionally… and was stunned to be summarily escorted out of the office, then handed some cash and a gag order.  The world didn’t operate the way I was taught to expect it to.

The problem with expectations is that they exacerbate pain and inhibit happiness. Psychologically, humans are more adversely affected by losses that they didn’t anticipate.  If our lost generation had never had our eyes on what we thought was a gender-agnostic corner office, our situation wouldn’t be quite so painful.


The Goldilocks conundrum

I personally know of a number of graduate-educated women facing the Goldilocks conundrum in their career:  Rejected as overqualified for low/mid-level positions, but perceived as an overly-risky choice for senior-level positions.  Qualified, ambitious MBAs and PhDs earning close to minimum wage driving Lyft or Uber…and making rent payments doing the soul-crushing things for which Lyft and Uber are only polite euphemisms.

No matter how much one professes a willingness to take yet another step backward in responsibility and pay in order to maintain optically-critical continuous employment, it’s nearly impossible to convince a company to over-hire.  I can’t disagree that it creates organizational friction to put someone in a lower-level role than they meritocratically deserve.

Meanwhile, it is still the case today for many corporations that putting a woman in a senior-level position is a groundbreaking decision for them.  The slightest doubt about the woman candidate is often significant enough to knock her out.  Powerful incumbents fear Type I errors of over-inclusion (false positive) more than Type II errors of under-inclusion (false negative).  [See my article “Progressives v. Conservatives: It’s all about fear of Type I or Type II errors”]

Companies are generally risk-averse.  Work history “risks” and personal “risks” are far more common among women.  Women disproportionately have to job-hop, accept variable work, take time off work, and wind up with a suspiciously non-linear track record.  It’s well-established that being married and/or having children is deemed a positive feature of male job-seekers and a negative feature for women job-seekers.  In my case, the core problem is the time I spent freelancing in order to take care of my ill husband.

Let me take a moment to review my credentials.  (I find this tiresome recitation is necessary to prevent hostile readers from mistakenly attributing my adverse experiences to their imagined lack of qualifications or chutzpah on my part):

  • Admitted to the top-ranked business school in the country.  Graduated with honors.
  • Beat out 499 b-school classmates for the only slot in the most coveted Wall Street internship.  Offered the most selective full-time job through corporate recruiting.
  • 99th percentile on all standardized tests:  SAT, GRE, GMAT, IQ
  • Admitted to an Ivy League college.  Graduated in the top 5% and earned multiple awards…while holding down a part-time job.
  • Voted “class brain” and also “most creative” in high school.  Swept the departmental awards in humanities and also STEM subjects.
  • Badass kitesurfer and backcountry skier whose idea of vacation is solo travel through travel-advisory areas of rural Mexico
  • Finagled former husband’s release from a Saudi prison when the State Department refused to intervene
  • Perceived as friendly, approachable and (as benevolent sexist candidate Barack famously described Hillary) “likable enough”. 
  • Not ugly (to pre-empt the all-too-familiar ad hominem accusation justifying a woman’s professional failures)

Nonetheless, I can’t get a good job.

Astronomers long believed that finding an exo-planet in the Goldilocks zone was only a matter of time and perseverance.  Sure enough, eventually such a planet was found. (As of this writing, we know of 8, among theoretically billions across the Milky Way.)  But the analogy breaks down there.  Human beings aren’t astronomical objects.  And, our value depreciates over time, so patience isn’t a reasonable coping strategy.


Sexism is still pervasive

Coded language, negative priming, soft-pedaling technical questions, moving interviews to coffee shops so they can ask illegal personal questions, asking illegal personal questions in office interviews anyway, sexualization both subtle and overt… this is part of the outrageous inequality that businesswomen job-hunters face daily.

Some selected recent experiences of mine:

  1. Former colleague and mentor of 17 years cut off contact with me because, now that I’m divorced, he fears his wife is jealous.  It is common for businessmen to avoid meetings with ring-less businesswomen, for fear of optics or subtext.  We’re excluded from the conversation, advice, brainstorming, and shop talk… and not uncommonly told that we should feel “complimented” that we’re attractive enough to incite this exclusion.  Overwhelming evidence points to having a senior-level sponsor/mentor as a key factor in professional success…which leaves us female sirens out in the cold when those senior-level people are mostly male and mostly uncomfortable with recurring interaction.  
  2. Male COO interviewer who hasn’t read my resume begins interview by announcing in obviously coded language that he doesn’t think I can “hack” their “intense environment”.  (Pointing out my Wall Street experience and extreme sport hobbies don’t help – he clearly had made up his mind when he first laid eyes on me.)
  3. Married male boss at a Fortune 500 cable company repeatedly complains that I don’t smile at him enough or hang out in his office enough. I reluctantly try to comply, but am not flirtatious enough.  He blows up at me over not replying to his email within the hour (who sends urgent requests via email?), screaming, “You’re just a fucking contractor! You need to do what I say!”  Only after I move on to my next job, I find out that he is notorious for hitting on women.
  4. Staffing agency that placed me with above company #3 refuses to place me again (punishing me for having been targeted for harassment).  This type of retaliation is one of the few discriminatory failure-to-hire situations that has proven winnable in court…but the risk of blackballing from pushing back against illegal action is too high for most of us.
  5. Employee of a consultancy I’m interviewing with counsels me that his firm serves company #3 as a client, is aware that my former boss has a reputation for harassing women, and has heard that I was one of his targets — I am told to be prepared to explain myself in interviews regarding my sin of having been harassed.  Blame-the-victim attitudes persist not only with assault and abuse of women, but harassment at work as well.
  6. Male networking acquaintance tells me it’s just as well that I lost out on a particular job because “someone like [me]” (i.e., female) wouldn’t want to “work long hours” and “try to fit into that [intense] environment”.  
  7. Retained search firm principal is eager to help me upon meeting in person. But, after receiving my resume, he emails me that I’m not worth his time because nobody who has spent time freelancing will ever get a job in the area of finance he covers. (Rejected for being a freelancer, I go back into the freelance pool – a negative feedback loop that’s now gone on for years.  Women are most likely to end up freelancing to begin with, and thus eliminating candidates on this basis is yet another gender bias.)
  8. Send thank-you email after a networking meeting with someone who plans to make an important referral. Receive a reply from his wife, who is apparently checking his email account.  Her email warns me to never speak to her husband again.
  9. Interview process involves being asked 6 separate times if I am able to travel, with thinly-veiled probing about whether I have “resources” (husband, live-in nanny) to handle last-minute and overnight trips.  I finally just volunteer the illegally-sought truth that I’m unmarried with no kids. (Presumably, bias goes in my favor for this one. But they continue asking me the question again and again, as if they don’t believe me… or don’t want to.)
  10. In lieu of the technical case study I was told to prepare for, interviewer for a consulting job asks me with a straight face: “If you were a dog, what breed of dog would you be?”  A year later after not getting the job, someone shares with me an internal email from that firm’s HR director to that interviewer, saying “Make it look like a real interview”.  It’s rare that we ever know what happened behind the scenes, which is one reason companies continue to get away with discriminatory hiring decisions.
  11. Informational conversation at a coffee shop. Guy calls me later to say he didn’t forward my resume internally as discussed, because he wants to ask me out for drinks socially instead.  So the saying goes:  “there are the women you fuck and the women you work with [or marry]”.
  12. Alum from business school offers to make some important introductions. He knows that I was recently assaulted by a lecherous landlord who went to jail. But, he will only help me if I assure him that “the assault was physical” and that I “didn’t do anything to provoke it”.  1 in 3 women are the victim of sexual assault in their lifetimes, and it’s not uncommon society to blame us and question our right to work due to suffering past trauma – even a supposedly enlightened, educated man like this who has daughters.
  13. Wealthy alum from business school glibly suggests I apply to a particular company simply because “they need women”.  (Despite our similar resumes yet gargantuan chasm in economic circumstances, he and many men seem to believe that women have not a disadvantage but an advantage.)
  14. Flown to Fortune 500 telecom company HQ for 2 days of interviews after 3 weeks of prep, to begin with dinner with CTO and SVP. Waiting at the restaurant where they made a reservation for 3, I get a text from the SVP saying they “forgot I was coming”.  SVP slaps together some pseudo-interviews the next day with people who haven’t seen my resume and don’t know what I’m supposed to be interviewing for. Despite me reaching out several times, I never hear back with an apology, explanation or follow-up from the CTO.
  15. Male interviewer won’t shake hands with me for “religious reasons”. (Could he really give fair consideration to working side-by-side with me?)
  16. Male interviewer asks if I have children and a husband, saying his company prefers to only hire people with “stable home life”.  Women like me get asked the illegal marital- and child-status question in almost every interview – in this case the interviewer was so unconcerned with the illegality of the question that he actually explained his reasoning for wanting to practice discrimination.
  17. Flown to consulting firm HQ for a full day of interviews. When I arrive, they have only scheduled 2 hours of interviews for the morning, and HR suggests that I “go shopping” for the rest of the day until my return flight departs. (I would have been the first-ever senior-level woman at that firm.)
  18. Interview for highly analytical job involves zero quantitative questions. I express surprise.  The interviewers say don’t worry about it.  Post-rejection feedback via the recruiter is that I “didn’t seem quantitative”.  If they don’t want you on the team, it’s trivially easy to engineer a situation with plausible deniability that it wasn’t a merit-based decision.
  19. My resume is littered with references to quantitative analysis, statistical methods, technical expertise, and finance work…. But male gatekeepers routinely assume I’m a “marketing person”.
  20. Conversations in coffee shops function as first-round interviews but can be characterized as not-an-interview, thus circumventing strict legal prohibitions against personal questions.  Questions about marital status, age, and child status are not uncommon.  (While I’m waiting for a cafe-based pseudo-interview, two businessmen nearby discuss how “women’s time isn’t worth anything” and thus women don’t work as hard.)
  21. Female interviewer asks me why I want to work, given that I must be married [she assumes, incorrectly]. 
  22. Male interviewer asks me why I want to work, given that I must have a divorce settlement [he assumes, incorrectly].  Women are generally perceived as less desperately in need of income, as society expects us to be someone else’s secondary income.
  23. 30-year-old CEO of a growth-stage startup asks me what year I graduated from college and then tells me he doesn’t need “mature resources” at his company.
  24. Meet with famous venture capitalist (and investor in company #23) who self-promotes as a great connector for newcomer job-hunters in the city.  He’s enthusiastic about my education… until he realizes that he and I are the same age.  He suddenly has zero ideas of any company in the area that would consider hiring me given my “level” (age).
  25. Male interviewer sits down and immediately tells me to “smile” (just like male strangers creepily do on the street).  Another male interviewer opens by complimenting my “great hair”.  Intentional or not, priming human beings about secondary social status (gender, race, age, disability) is a powerful tool well-known to decrease test scores, confidence, and physical performance. Start by reminding someone you see them as an Other and it adversely impacts everything that follows.
  26. Head of career services at my business school counsels me on my career conundrum….Given my combined problems of gender, age, freelancing past, and generalist background, she concludes that my best bet is to “find a husband”.  After all, there’s a documented 60% gender wage gap for 10-year-out alums from this particular b-school.
  27. Twice told by men in networking conversations that I could solve my career problem by becoming an escort.  I’m told that I’m “lucky” that I have this option uniquely available to women.
  28. Told by male friend at a software company considering me for a role that I should “just go be a yoga teacher”.  Not only is this an insult to my education, intelligence, and 20-year business career, it’s an incorrect assumption that I must love yoga because I’m female.  Men’s essentialist bias against women makes them think we don’t really want business jobs, and that we’re secretly wishing we could go do so-called girly things.  A business career leveraging my education and intellect is very much my passion and goal – no less so than for any man in my position.
  29. Fortune 500 Internet company hires a less experienced man for a job they’re discussing with me…but without ever interviewing me.  Asking two candidates different questions is the basic legal definition of discrimination – which these companies undoubtedly know by defy anyway.  Here’s how these things happen:
    1. First, meet CFO and Treasurer in proverbial coffee shop. I had applied for several mid-level operating job postings and was looking for help getting my name in the right pile —  but, CFO and Treasurer surprise me by volunteering that they want to think about creating custom, high-level strategy position for me. 
    2. Another coffee shop meeting reiterates their strong interest, but that they need time to define the position for me.  
    3. After much follow-up on my part, I’m invited to office for “interviews” — but nobody I speak to has seen my resume, everyone says they were grabbed just a few minutes ago to speak with me for reasons unknown to them, and so nobody asks me any interview questions (much less anything technical).  
    4. Next meeting with Treasurer is back in the coffee shop, where, after arriving 30 minutes late, he flippantly tells me they hired someone else for the position weeks ago (10 years less experienced, similar industry background, lesser academic credentials by any measure). Meanwhile, the open positions I had applied for have magically all been filled, and he says he can’t help me because he’s left the company in early retirement.  
    5. Treasurer suggests I fly in (on my own nickel) to “interview” with the newly-hired kid.  I invest in a cross-country flight, only for the kid to last-minute change our meeting to…a 10-minute chat in a coffee shop.  He tells me that, while the company execs were having lightweight chats with me about the weather, they were conducting formal case studies and technical interviews with him.  

A woman has little recourse against the above behaviors, regardless of their legality. As a practical matter, involving a lawyer or the EEOC won’t resurrect the job you were passed over for…and it will get you a public record of being litigious.  Try to resolve it with gentled real-time push-back results in being labeled “difficult”, “angry” and “bitchy”.  The only viable option is to do nothing (and vent in an anonymous blog post!).

For example, regarding issue #29 above:  The Treasurer consented to debrief with me 5 months later (at which point he’s cashed out his IPO winnings to find a beach in his mid-40s… while I’m at his same age trying in vain to get my foot in the door). He’s a fellow alum from the same school, which normally translates into a significant level of respect and special consideration. But he expressed no accountability — much less remorse — for his and his firm’s actions, and was indignant that I “seemed upset” about the treatment.  As token appeasement, he sends my Finance and Strategy resume to his long-lost friend at another firm, suggesting she have coffee with me to discuss my potential suitability for a theoretical… (you guessed it!) Marketing role. 

In addition to misogyny in the professional sphere, it is also, of course, rampant in the social sphere.  Like one-third of American women, I too have been raped.  I realize from experience that this information isn’t disturbing to most men, and so I too minimize it.  My greater pain is that the world I live in today is one where sexual coercion is commonplace, and the idea of freely-given consent is increasingly muddled (even before “grab ’em by the pussy” was absurdly waived away as “harmless locker room talk”).  Not infrequently, I encounter men who expect me to use my body as currency – in exchange for friendship, for housing, for networking help, for work, for social inclusion.  And, nowadays, women face a dating dynamic that routinely involves vicious verbal attacks (and sometimes worse) when we refuse sex on a first date.  American men increasingly seek the “prostitute experience” instead of the previously-idealized “girlfriend experience”.  This objectifying attitude spills over from the social to the professional world.  Consider the entitled deceitfulness and careless devaluation of my time and abilities in #29 above: That same attitude about hiring women is how business executives rationalize adultery in their private lives.  Numerically speaking in my mid-sized city, it’s only a matter of time before one of the married men propositioning me turns out to also have a gatekeeper role in an interview process.


The personal meaning of Hillary’s defeat

Yesterday I voted, cautiously optimistic that the election of a woman president would one day trickle down to my personal life – even though, tragically, that hasn’t happened for black people living under a black president.

Today, the unexpected election result reaffirms and re-normalizes systemic male privilege and misogyny.

We elected a fear-mongering, openly racist, xenophobic, anti-science, reckless real estate developer with a flippant ignorance of international affairs, blatant disregard for facts and data and indiscriminate verbal cruelty, who repeatedly belittles women, has unapologetically bragged about sexually assaulting them and currently faces criminal allegations.  Our two past Republican presidents didn’t vote for him.  Many Republican Congresspeople disavowed him.  But half of white women voters, 1 in 5 African-American voters, and 1 in 4 Latino voters chose him.  Less unexpectedly, a strong majority of white men found his unhinged bigotry comforting.  He is the first president in 240 years of American history with zero political or military experience.

Meanwhile, Hillary Clinton spent 20-some years as a practicing lawyer, 18 years as advisor to a Governor and then President, 8 years as a Senator, 4 years as Secretary of State and a lifetime dedicated to public service, non-profit work and advocacy.  Yet, preposterously, I’ve personally heard numerous right- and left-leaning men claim to me that she “doesn’t have any experience”.  These are sometimes the same men who control my access to meaningful work via their evaluation of my experience.  How likely is someone holding that prejudiced viewpoint to see ME as experienced and qualified for a job commensurate with my capabilities?  How could the gendered, counter-factual dismissal of Hillary’s voluminous resume NOT be paralleled in unfair dismissal of my own impressive resume?

Among the men who set aside Trump’s tales of groping women to vote for him, some are the very same men in senior corporate roles who I aim to work for.  How could their tolerance of such behavior by their candidate NOT translate into what they feel is tolerable treatment of me?

Clinton inspires irrationally non-specific, highly-gendered vitriol.  She has been scrutinized to a degree that Trump was not, and her high marks and exonerations have been ignored.  Her accomplishments are minimized because she’s female and because she’s married to an accomplished man.  People criticize the sound of her voice, the fit of her clothes, and the shape of her body – but they don’t criticize those features of Trump.  Trump has “broad shoulders”, a “fiery” voice, and “intensity”.  Clinton has “cankles”, a “shrill” voice, and “lacks stamina”.  Some women even join in the hateful choir, identifying more with Trump’s promised anti-minority crusade than with Clinton embodying a step forward for their own kind.  People whose vote violates their own dignity and self-interest are betting that participating in the nastiness against Clinton protects them from being targeted.  (There was analogous, race-based vitriol against Obama, slandering him as a non-Christian and non-American.  Thankfully, it wasn’t a successful argument at the ballot box.)

Yesterday, hypocritical fundamentalist Christians voted overwhelmingly for a thrice-married, adulterous atheist. Those ~20% of our citizens believe that women should not head a household, head a church or head a government.  They identify more fervently as misogynists than as keepers of their own scriptural commandments. When I encounter those same people in my job search, how likely are they to hire a woman to head a department?  Can we see how they reiterate their presidential vote by prioritizing keeping me in my place, over modeling “Christian” loyalty and sincerity?

Years ago, when I sacrificially sidelined my career to care for my ailing husband, we both liked to joke that I was “his Hillary” – deeply involved in producing work in his name, knowing I wouldn’t get credit for it publicly.  It was once common in America to suggest that, if not for Hillary behind the scenes, Bill Clinton “would have wound up pumping gas.”  I thought for a time that the comparison had lost its punch, since Hillary did get credit for serious, independent accomplishments after her husband left office.  But I learned last night that the comparison remains valid.


Deal us in

Over the past year and a half, I’ve met at least once with the CEO, CFO, and/or CTO of the major telecom companies in my city. (All of them. And the advisory firms that principally serve them.  And senior people at the smaller industry players also headquartered here.)  I am grateful that the fancy academic degrees on my resume open doors to get those meetings.  But, unless it translates into work, that is only an illusion of privilege.

Each of those executives has told me how theoretically impressive and appealing and rare I am as a resource… but that one of the other executives in his circle will surely be smart and lucky enough to snap me up.  Just be patient.  (And in the meantime…survive how?)  It’s a seemingly endless cycle of “who’s on first” deflection, and in the meantime I fall endlessly further behind.


The 1970s-1980s East Asian “economic miracle” was greatly dependent on female workforce mobilization.  Women entered the formal workforce in large numbers (albeit disproportionately relegated to increasingly variable, low-wage work to support the export sector). GDP and GDP per capita increased dramatically, miraculously.

Sadly, the longer story arc of the Asian Tigers includes the fact that many of those women were later ejected back out of the workforce as they aged.  Moreover, the countries that disadvantaged new women workers the most, grew the fastest.  However, the point remains that opening up productive work opportunities to underutilized would-be workers is valuable to society overall.  It seems self-evident that leveraging America’s lost generation of businesswomen would boost our economy. 

“Just hire yourself” is one of the sneering, flippant dismissals I sometimes field when discussing this topic. But, entrepreneurship outside the standard corporate path isn’t accessible to women if we aren’t allowed inside to begin with.  In order to find investors, co-founders, and customers, we need the professional network and resume credibility that comes from gainful employment.  Crucially, we need the financial savings accumulated from years of fair pay, in order to feasibly peel off to start new ventures.

Consider the massive opportunity cost of a whole cohort of businesswomen languishing like me.  We spend what should be the peak years of our professional lives begging to be taken seriously for intellectually-appropriate, career-track jobs, while doing mental gymnastics to rationalize the existential pain of settling for unskilled survival work.

It’s a sad truism of psychology that men and women generally respond negatively to women seeking power.  Hence the irrational protest vote of Obama fans for Trump (per today’s emerging explanation of last night’s electoral upset) and women and minorities against their own self-interest and self-worth.  Female ambition – not even to dream, but merely to survive – feels unnatural to the gatekeepers who could solve my problem.  But, what if I were perceived not as a power-seeking threat, but rather as an opportunity?  The arbitrage value is extraordinary for whoever picks up the economist’s proverbial $100 bill off the sidewalk.  All someone like me wants is to leverage my brain to productively and meaningfully contribute to society.    

— November 9, 2016

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