(15-minute 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 cannot 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 MBAs 10 years after graduation has recently been estimated as 60%.  In other words, we make less than half of our male b-school classmates, after salaries have had a decade to progressively diverge.

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 did not expect a fair shot. They knew they were entering a world where they were not 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 few exceptional women by name . . . because there are few enough examples such that they can be enumerated individually.

On the other hand, women younger than us will undoubtedly 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 of the human 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.

Our current president [Trump] has explained to us that the proper response to workplace sexual harassment is to quit your job and find a different one.  But back 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 did not 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 did not 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 did not anticipate.  If our lost generation had never set our sights on a gender-agnostic corner office, our current situation would not feel quite so painful.

The Goldilocks conundrum

I personally know of many 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.

No matter how much one professes a willingness to take yet another step backwards in responsibility and pay in order to maintain continuous employment (which is so crucial for optics, to get the next job), it is nearly impossible to convince a company to over-hire.  And I confess that I cannot 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 constitutes a hand-wringingly groundbreaking decision for them.  The slightest doubt about the woman candidate is often significant enough to knock her out.  Incumbents in power fear a Type I error of over-inclusion (false positive) more than a Type II error of under-inclusion (false negative).  [See my article “Conservatives v. Progressives: It’s all about fear of Type I vs Type II errors”]

Companies are generally risk-averse.  And work history “risks” and personal “risks” are far more common among women.  Women disproportionately have to job-hop, accept variable work, take time off of work. Consequently, we wind up with a suspiciously non-linear track record.  It is well-established that being married and/or having children is deemed a positive feature of male job-seekers but a negative feature of 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.  (This is necessary so that the reader can comprehend the validity of the troubling experiences I later describe, without casually dismissing them as due to some imagined lack of qualifications, chutzpah, or tact on my part):

• Graduated with honors from the #1 ranked business school, where I secured the most coveted Wall Street internship, shone as a natural leader in group assignments, and was in high enough demand to turn down several coveted full-time offers.
• Breezed through college, graduating summa cum laude from an Ivy League school, getting the departmental award in my major, and also the departmental award in my minor (a language I had only begun learning two years prior) . . . all the while also holding down a half-time job off-campus.
• In middle/high school, received departmental awards for both the humanities AND the sciences, was voted both “class brain” AND “most creative”, slayed at both regional math AND regional music competitions, was proud to be the first girl to get the industrial arts award, and tested at >145 IQ.
• Extroverted and hard-working, a badass kiteboarder and skier who isn’t afraid to get muddy and is steely enough to, for example, sojourn alone through travel-advisory areas of rural Mexico. Fiercely loyal and resourceful, saved former husband’s life more than once, and finagled his release from a Saudi prison when the State Department refused to intervene.
• Perceived as friendly, approachable and (as Barack described Hillary) “likeable enough”.  Conscious of the unearned privilege of being a white, native English-speaker with an upper-middle-class upbringing.  And, (to pre-empt the all-too-familiar ad hominem accusation justifying a woman’s professional failures) not ugly.

Nonetheless, despite years of dogged effort, I cannot 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. (Today we know of eight, among theoretically billions across the Milky Way.)  But the analogy breaks down there:  Human beings are not astronomical objects; and our value depreciates over time, so patience is not a reasonable coping strategy.

Sexism is still pervasive

Selected recent experiences of mine:

1. Former colleague and mentor of 17 years cut off contact with me because his wife is jealous.
2. Male interviewer who hasn’t even read my resume begins the interview by announcing that he doesn’t think I can “hack” their “intense environment”.
3. Married male boss repeatedly complains that I don’t smile at him or hang out in his office enough. I try to comply without being inappropriate, but am not being flirtatious enough.  He blows up at me one day 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!”  After I move on, I find out that he became notorious for hitting on other women.
4. Employee of a firm I’m interviewing with counsels me that his colleagues will infer that hit on by or slept with my ex-boss in #3 above, since they are aware that my ex-boss is known for such behavior . . . and I should be prepared to explain myself (for the sin of having been hit on, and to confirm that I did not sleep with him).
5. Male colleague tells me it’s just as well that I lost out on a particular job opportunity . . . because (he assumes) someone “like [me]” wouldn’t want to “work long hours” and “fit in to that environment”.
6. Retained search firm partner is eager to help me after meeting in person. But, after receiving my resume, 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. 
7. I send a thank-you email after a networking meeting with someone who plans to make an important referral. Receive a reply from his wife using his email account, telling me to never speak to her husband again.
8. Interview process involves being asked six separate times if I am able to travel, with thinly-veiled probing about whether I have “resources” (i.e., 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. Bias goes in my favor for this one.
9. In lieu of the case study I was told to prepare for, female interviewer for a consulting job asks me “if you were a dog, what breed of dog would you be?”
10. A year after the dog-breed case study incident (#9 above), an internal email surfaces from that firm’s HR director to that interviewer, saying “Make it look like a real interview”.  
11. Informational conversation at a coffee shop with an employee at a prospective employer. The guy calls me later to say he didn’t forward my resume internally as discussed . . . but asks if I want to meet at night for drinks. Evidently, I can be seen either as a prospective colleague or a prospective girlfriend, and he decided to cut me off from the former in order to selfishly hope to achieve the latter.
12. Alum/friend from business school offers to make some important introductions. He knows that I was recently assaulted by a lecherous landlord who went to jail. He will only help me if I assure him that “the assault was physical” and that I “didn’t do anything to provoke it”.
13. Wealthy alum from business school suggests I apply to a specific company simply because “they need women”. Despite the chasm between his and my economic circumstances, he feels and resents that I have an advantage in job-hunting he doesn’t have.
14. Flown out of state to a company’s HQ for two days of interviews that I’ve spent three weeks prepping for. Interview process is to begin with a private dinner with the company CTO and SVP. Waiting at the restaurant where they made a reservation for three, I suddenly get a text saying they “forgot I was coming”.
15. Male interviewer won’t shake hands with me for religious reasons. Did he give fair consideration to working side-by-side with me on a daily basis?
16. Female interviewer asks me why I even want to work, given that I’m married. (Though I’m not married.)
17. Male interviewer asks me why I even want to work, given that I must have a divorce settlement. (Which I don’t.)
18. My interview for highly analytical job strangely involves zero quantitative questions. I express surprise. They say don’t worry about it. Post-rejection feedback via the recruiter is that I “didn’t seem quantitative”.
19. My resume is littered with references to quantitative analysis, statistical methods, technical expertise, and finance work . . . But I am often assumed to be 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, child status are not uncommon.  
21. Meet with famous venture capitalist who prides himself in being a great connector for newcomer job-hunters in the city. After considering my resume, he has no ideas of any company in the area that would consider hiring me given the combination of my “level” and “background”.
22. The 30-year-old CEO of a startup tells me he doesn’t need “mature resources” at his company.
23. Male interviewer tells me to smile, just like male strangers creepily do on the street
24. Head of career services at my business school counsels me on my career conundrum.  She admits my best bet may be to find a husband.  
25. Twice told by men in networking conversations that I could solve my problem by becoming an escort. 
26. Told by male friend at a software company considering me for a role that I should “just go be a yoga teacher”.
27. Company hires a less experienced man for a job they’re discussing with me . . . but without ever interviewing me:

Meet CFO in coffee shop. He will think about creating custom, high-level position for me. Another coffee shop meeting reiterates strong interest.  Invited to office for interviews, but nobody I speak to has seen my resume, knows why they were asked to speak with me, or asks me any technical questions at all.  At next coffee shop meeting, I’m told they hired someone else for the position weeks ago.  Then asked to fly in to meet the newly-hired guy, who at last-minute relocates our meeting to . . . a coffee shop.  This new guy is ten years less experienced than me, with similar industry background, and lesser academic credentials.  I was never asked a single technical question, but I’m told I lost out due to not being technical enough.

In addition to misogyny in the professional sphere, it is also of course rampant in the social sphere.  Like a third of women in their lifetimes, I too have been sexually assaulted.  I realize from experience that this information is not even disturbing to most men, and so I minimize it as well.  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 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 cross-pollinates between the professional and social worlds.

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 has not 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 did not 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 have 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 interpretation of my 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 is female and because she is 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 do not 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 was not 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 would never 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 have met at least once with the CEO, CFO, and/or CTO of the major telecom companies in my city. (And with the advisory firms that principally serve them.  And with 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 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 is 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). Both 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 dismissals I sometimes field when discussing this topic. But entrepreneurship outside the standard corporate path is not accessible to women if we are not 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 is 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 whomever 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