Chapter One: Machiavelli’s Playbook 1 Machiavelli’s Playbook
“Since it is my intention to say something which will be of practical use… I have thought it proper to represent things as they are in real truth, rather than as they are imagined.”

—Machiavelli, The Prince (Chapter XV)

Machiavelli wrote The Prince for women in the workplace. Granted, he himself might be pretty surprised to hear this—he wasn’t exactly a champion of gender equality—but he writes, in the beginning of The Prince, that there are two kinds of princes: those who inherit their kingdoms and those who take control of a kingdom through conquest. For a prince who inherits his kingdom, Machiavelli writes, things are generally pretty cushy: the people are used to him, “his subjects will be naturally well disposed towards him,” and for him to lose his position, he really has to screw up (Chapter II, MPE). You can think of college-educated white men as the inheriting princes of the workplace, and Machiavelli did not write The Prince for them.

The conquering prince, on the other hand, is in a very tricky position and “difficulties abound” (Chapter III, DTE): He just took over a new land, things are in flux, and everyone is skeptical of him—like, “Wait, who is this guy we’re suddenly supposed to be taking orders from?”

It is for the conquering prince that Machiavelli wrote his most famous work. As women in the workplace, we are the conquering princes. Women have arrived in the American workplace! We are getting the degrees and we’re in all the industries and we’re rising through the ranks! This is good news and a real and substantial victory, but the workplace is still new territory for us. Change is incredibly hard. The patriarchy is not going quietly, and if the data is telling us anything, it’s that we need to change our tactics.

As luck would have it, The Prince is a brilliant tactical guide for how to gain and hold power over a newly conquered land. It is not a book about war (although Machiavelli is generally very enthusiastic about war); it’s a book for what to do after you win the war (the après war, if you will): You got the degree! The job! The big assignment you never thought you’d get! It’s yours! Now what? How do you keep the gains? How do you grow them?
Machiavelli’s Big Break
Machiavelli himself was a bit of a new prince. Nobody is quite sure how he got his first government job, but everybody agrees it was a total coup. Machiavelli was hired as a low-level diplomat when he was twenty-nine, and he was very far from a shoo-in for the position. He was not from the “right” family. His father was trained as a lawyer but had gone bankrupt, lost his license, and was reduced to trying to scratch out a living from his property. That didn’t go so well: He was always in terrible debt, and Niccolò and his family grew up in near poverty. However, Machiavelli’s father loved literature, history, and learning. There are even stories of him trading chunks of land for books. One thing is sure: Machiavelli Sr. spent some of the money he did have educating his son in what seems to have been a pretty over-the-top way, considering the family’s situation. Niccolò Machiavelli got a full, classical education and was instilled with a deep and lifelong love of history and literature. That may have been what helped get him his job. Still, Machiavelli’s spotty family history was a drag on him his entire career. Nobody worked harder than Machiavelli. He was, by all accounts, brilliant at his job, a tireless worker, and well-liked by his colleagues. But he was held back from a bunch of promotions and high-profile assignments because he simply didn’t have the pedigree.
The Power Principle
Power is an interesting concept. Although it is the main focus of Machiavelli’s book, he never explicitly defines it. So what is it? What is this thing Machiavelli is obsessing over?

Power doesn’t exactly have the best reputation. Say the word and it conjures up images of men in expensive suits behind giant desks, screwing over investors; General Patton barking at a bunch of faceless troops that America will not tolerate a loser; the Eye of Sauron crushing little Frodo. Power has become, I think, synonymous with the ability to force people to do things. If someone is described as being power hungry or drunk on power, it is not a compliment (at least, not for most people. Maybe for Sauron).

I don’t think “power” in the way we commonly think of it is what most women want: The ability to crush underlings is not a life goal for most well-adjusted people. But that does not mean women aren’t interested in power. I think what women want in the workplace has a lot more to do with the original meaning of the word. Its original Anglo-French root, poeir, means “to be able.” I think that’s a very useful definition. Power means being able to do things, to have agency and be the masters of our own fates. Women in the workplace want to be able.

Of course, for most of recorded history, being a woman has largely been defined by not being able: not being able to own property, vote, smoke cigarettes, get an education, drive, practice most professions, travel alone, live alone, or participate in government. In literature and on-screen, when women weren’t being locked in towers, married off to secure some political alliance, or manic-pixie-drifting through some guy’s hero journey, they were home waiting for their husbands/fathers/brothers/boyfriends/baby daddies to come back. Women weren’t where the action was. Women waited. Any power women had was confined to martyr-like virtue or a whisper in the ear of a man who actually did have power; see Lady Macbeth, Scheherazade, Medea, Ophelia, Cleopatra, Penelope. Even today, women tend to fit into these roles. Take the hit TV series Game of Thrones, which seemed, for years, to be a narrative all about strong women seizing power. The show systematically destroyed every powerful woman in the last few episodes of the show. Most offensively, Khaleesi Daenerys Targaryen—breaker of chains, mother of dragons—who, after commanding armies, traversing continents, raising actual dragons, outsmarting wizards and kings, and striding naked out of multiple burning buildings, went crazy when her boyfriend dumped her. She went so crazy, her lousy boyfriend was forced to kill her and hand the kingdom over to a white guy from a good family. These are the stories we take in all our lives. It’s no wonder the world has issues with women in power.

Just look at the difference in how we use the words prince and princess. If a man is a prince, he is a model citizen, a cut above the rest, and everybody wants a piece of him. If a woman is a princess, she is difficult, entitled, demanding, and you soooo don’t want to be in her bridal party.
What Is Standing Between Us and Power?
What is the difference between the inheriting prince and a new prince? A little bit of historical precedent and a sweet family crest, but mostly it’s a story. In fact, the main obstacle between women and power is not a sexist manager or an oppressive organization or even the dreaded patriarchy. It is a story of our own worth.

The story is, quite simply, that women are less valuable than men are. Dr. Cecilia L. Ridgeway is a Stanford University sociologist and author of Status: Why Is It Everywhere? Why Does It Matter? She says women, by and large, are considered to be “low-status” and men—college-educated white men, specifically—are considered to be “high-status.” High-status people typically “set the agenda”: They talk a lot, make decisions, and have strong opinions. Low-status people follow the agenda: They listen a lot, execute orders, and make sure high-status people have the support and resources they need—they are essentially the Igors and Renfields to the high-status Dr. Frankensteins and Count Draculas.

Leaders are, by definition, high-status. So when women are in leadership positions, it often does not sit well with people. Imagine if you saw a twelve-year-old scolding her parents or the office intern started laying out his vision for the company to the CEO; those are low-status people behaving in a high-status way, and it can stir up strong emotions in people, like shock, resentment, and outrage. Those are the emotions many people feel about women in leadership roles, even if they don’t want to feel that way.

But this is good news! We’re not fighting anything real. We are not dealing with a lack of brains or ability or skill or work ethic. (Studies show basically everybody agrees on that.) The truth is, women already have everything they need to thrive and rise in the workplace, and the workplace will be better for it. All we have to do now is make that happen. And to do that, we need to tell a new story.

There are a bunch of things working in women’s favor. First, stories change all the time. (Sixty years ago, cigarettes were good for you, marijuana was bad for you, and women didn’t enjoy sex.) Also, workplaces are full of people with the best of intentions, who are ready to make changes, and who want an equal, more diverse workplace. But stories can also be formidable, because they are woven into our identities. We use stories to make sense of things, and letting go of them can make the world seem frightening and chaotic. In a way, people are fighting for their lives when they’re fighting for their stories. Our stories, as David Foster Wallace pointed out, are the water we swim in.
Machiavelli Feels Your Pain
Machiavelli, incidentally, was no stranger to the awesome power of stories. In fact, when a story changed, he lost everything.

Machiavelli thrived in his job as a diplomat. For about fifteen years he was sent all over Italy and much of Western Europe to represent Florentine interests. Popes and kings knew his name; he worked on projects with Leonardo da Vinci; and he was involved in international affairs at all the highest levels. He had properties all over Tuscany, a devoted wife, six kids, and adoring friends. He was a true power player. But when he was forty-three, Machiavelli’s luck ran out in a big way. The powerful Medici family seized control of Florence and, as a high-ranking member of the fallen republic, Machiavelli was stripped of his job and his money, accused of conspiracy, and thrown in jail with “shackles clawing into my ankles” and “lice so big and fat they seem like butterflies.” He was tortured and interrogated for weeks, and was incredibly lucky not to have been killed. But the Medicis let him live, let him out, and ran him out of town.

It was in exile that Machiavelli wrote The Prince.

They say the Bedouins sang songs about water because they had no water. Niccolò Machiavelli wrote about power because, at the time he wrote The Prince, he had none. He had lost everything.

Machiavelli wrote The Prince in a tiny rural village outside Florence where his family owned a small, scruffy tavern and brothel—far from the social elites and levers of power he so loved. He spent his nights poring over ancient texts, studying the great kings and warriors of history: men who had conquered nations and created stable, prosperous kingdoms. Machiavelli confided to a close correspondent that these historical figures felt like his friends and seemed more real to him than the actual humans around him, most of whom were farmers, low-level merchants, and prostitutes. He so revered these historical figures that he would dress up in formal clothes before sitting down to do his readings, which he did alone in a small stone apartment attached to the tavern.

Machiavelli’s lack of power is painfully obvious in the opening bars of The Prince. “Should you from the height of your greatness some time turn your eyes to these humble regions,” he writes, “you will become aware how undeservedly I have to endure the keen and unremitting malignity of Fortune” (Dedication, DTE). Machiavelli wrote these words to Lorenzo de’ Medici, who was, in fact, the cause of his “malignity of Fortune.” The Prince, Machiavelli’s love letter to Florence, was also a kind of cover letter. Machiavelli was hoping the book would shine so brightly, and its ideas for Florence and Italy would resonate so deeply, Lorenzo would say, OMG, HE’S SO BRILLIANT! I DON’T CARE IF HE WORKED FOR THE OTHER SIDE, I HAVE TO HAVE THIS GUY ADVISING ME!

The Prince was Machiavelli’s Say Anything boom box moment to the powers that were. He writes, heartbreakingly, that the work represents the very best he has inside of him: “Though I deem the work unworthy of your greatness,” he writes to Lorenzo, “yet I am bold enough to hope that your courtesy will dispose you to accept it, considering that I can offer you no better gift than… all that in the course of so many years, and at the cost of so many hardships and dangers, I have learned, and know” (Dedication, DTE). This is how the great and ruthless Machiavelli begins his book: begging the man who took everything from him to pity him and let him back into the fold. The Prince! The great treatise on power! The infamous guide to being unapologetically ruthless! And it starts out in the most submissive, pathetic way imaginable. He apologizes. He flatters. He grovels. And after all of this cringe-worthy bowing and scraping he actually delivers. In The Prince, Machiavelli lays out some of the boldest, most original ideas of his day. He looks at things with an honest (if slightly cynical) eye and speaks his truth—an uncomfortable and shocking truth that shook the very foundations of humanism, which Cicero had laid down centuries before. Machiavelli’s observations were not noble or soaring. They were not inspiring or heartwarming. They did not make you feel good about human beings. But they were real—born of the bloody, vicious feuds Machiavelli had witnessed during his life and career and had studied from centuries past. Now that is a boom box moment if ever there was one.

Except that it didn’t work. It seems Lorenzo never even bothered to read the book. The Prince did get some attention, but it was mostly shock and horror at what Machiavelli had written, culminating in a threat from the all-powerful Catholic Church to excommunicate anybody who bought the book (which, I can only imagine, was very hard on sales).

On top of being broke, exiled, and unemployable, Machiavelli was now notorious and despised. He did not get his job back. He did not return to Florence in triumph, and his city and his country were not saved by him. Machiavelli was crushed by this turn of events and wrote to his friend, “I shall continue, then, among my lousy doings, without finding a man who remembers my service or who believes that I can be good for anything.”

Machiavelli went from being a power player, a patriot, and a political savant to a disgraced traitor and a villain. When a story changed, he lost everything and found himself in the same position as many women in the workplace: on the outside looking in, for reasons that had nothing to do with merit.

Machiavelli knew the powerful role stories could play in our lives all too well. So what is Machiavelli’s advice when you’re going up against a story that is holding you back?
Machiavelli’s Lesson: Don’t Blink
One of Machiavelli’s main messages in The Prince is one of the simplest and also one of the most difficult: See the situation you’re in clearly. Face reality. Don’t blink.

Machiavelli thought the inability (or unwillingness) to see things as they were was one of the most common pitfalls for princes. In The Prince he recounts many instances of leaders and generals who refused to look at the reality of their situation and who lost battles or kingdoms as a result. His conclusion: Fully facing reality is crucial, even for the cleverest, most prepared prince, because “the times are more powerful than our brains.”

It’s human to want to avoid bad things and not look at something ugly. There’s a reason kids lie paralyzed with terror under their comforters, convinced there is a monster under the bed, without actually ever just looking to see. Facing discrimination can feel like this: You’ve already put up with years of unfairness—a harder time getting hired, a harder time getting promoted, lower pay, a more critical eye on your work, harassment, disrespect in all its glorious and glittering forms—not to mention the regular challenges of a workplace: endless meetings, toxic colleagues, bad managers, layoffs, crazy politics, budget cuts, your yogurt getting stolen out of the communal fridge. And now you’re supposed to focus on a big, systemic problem like discrimination? Just so you really see it in its full shittiness?

Yes.

To fight this monster, you need to know it. That is not easy. Most people will do almost anything to avoid looking and, for that reason, there is a major denial problem around gender discrimination in the workplace. Me? Sexist? No way! I voted for Hillary! The truth is, we all have gender issues. They’re pretty impossible to avoid, given the culture we’ve grown up in. Most people don’t mean to discriminate. They will tell you—and 100 percent believe—that discrimination is wrong: They would never do it and have never done it. The truth is, they almost certainly have and will again.

That denial is insidious. Institutions that claim to be meritocracies have been shown to have bigger gender discrimination problems than institutions that acknowledge having a problem. Similarly, people who think of themselves as super-woke, color-blind, equal-opportunity-for-all types tend to discriminate far more than people who acknowledge they have biases.

But this denial doesn’t just come from companies or managers. You will, quite crushingly, often hear this denial from women themselves. Carly Fiorina, upon becoming the CEO of Hewlett-Packard in 1999, used the occasion to announce that her appointment was proof that gender discrimination was no longer a problem.

“I hope that we are at a point that everyone has figured out that there is not a glass ceiling,” she declared at a news conference. Six years later she was pushed out of the company and largely blamed gender discrimination.

This brings us to the final place you will see denial: from yourself. Seeing discrimination is a tricky business. For one thing, it can be really hard to know if you’ve been a victim of gender discrimination or if things just didn’t break your way. Maybe Joe was a little more qualified for that position. Maybe Jerry should be paid a little bit more. To complicate things, Joe and Jerry are usually hardworking, qualified people who are just trying to get their shot, too.

Dr. Stefanie K. Johnson studies gender discrimination and harassment at the University of Colorado Boulder’s Leeds School of Business. She sees this denial all the time: “I can’t tell you the number of women I interviewed who are like, ‘I’ve never experienced sexism. Everyone loves me!’ And it turns out they have been sexually harassed and passed over for jobs.” This denial, says Stefanie, comes from a self-protective place: “It’s actually more detrimental to your self-esteem to admit you’re being discriminated against than it would be just to say, ‘I wasn’t good enough,’?” she explains. “?‘I wasn’t good enough’ means ‘I can get better!’ But ‘People just hate women’ means ‘I’m never gonna get over this.’?”

Joan C. Williams, gender researcher and coauthor (with Rachel Dempsey) of What Works for Women at Work: Four Patterns Working Women Need to Know, was a law professor at a major university for years, and says everyone in her department thought of her as the proverbial dragon lady: “I was a bitch for twenty-five years,” she says. Joan thought it was happening because she wasn’t as good at office politics as her male colleagues. “Then I realized that it wasn’t that I was politically maladroit; I was just encountering a lot of gender bias. Office politics are just a lot more difficult for women than they are for men.” There was relief in realizing this, but there was also a lot of pain. Joan says the way she was treated in her workplace took a major toll on her and her family. “I was an angry person for a really long time,” she says. “So it’s really a bummer.”

Joan’s takeaway: “Women can totally crush it at work, so long as they’re about twice as politically savvy as men.” That’s a lot of savvy on top of a day job. And a family. And gas bills. And getting in your ten thousand steps.

Ladies, I ask you now to face the monster—a story that is big and insidious and ugly and entrenched and powerful and destructive and annoyingly hard to kill. The reason I ask you to do this is that facing this monster is essential to slaying it.
Meet the Monster!
Individual situations can be murky, but the data shows us the glass ceiling is real. In one study (that made me want to set myself on fire, incidentally), subjects were given two (fake) résumés of applicants for a management position at a construction company. The “female” résumé had more education, and the “male” résumé had more job experience. The group was asked, before seeing the résumés, which quality was more important for the job, and determined education was more important. But guess what? After seeing the résumés, the group picked the man’s résumé, saying his experience put him over the top and the woman’s education just wasn’t equal to it. But when the names were switched—when the man’s name was on the résumé that had more education and the woman’s name was on the résumé with more job experience—the man’s résumé was seen as superior, citing education as the more important qualification.

In a study out of Yale University, identical résumés were topped either with a male or a female name. Study participants were asked to assess the résumés and find the best candidate for an entry-level STEM job. Not only did they think the man was more qualified for the job, they also thought he should get paid more.

When gender is taken out of the equation and people are simply judged on merit, these issues vanish. In a study by Harvard University economist Claudia Goldin, when a professional orchestra auditioned people behind a screen (so nobody knew whether the musician was a woman or a man), women were 50 percent more likely to advance in the audition process and 250 percent more likely to get the job.

Ladies, if you needed some cold, hard evidence, here it is: People’s ideas of what makes someone qualified for a job, how much someone should get paid, and even how well a person knows their way around a bassoon will literally change to justify their own (certainly unconscious) biases.

So, okay, the glass ceiling is there. But how does our monster manifest? How does it show up in women’s careers? There are a couple of main ways:
The Cinderella Syndrome
As long as we’re talking about princes, we might as well invoke a princess. A major way the glass ceiling shows up is something I’ve come to think of as the Cinderella Syndrome. In the fairy tale, the good and beauteous Cinderella wants to go to the ball, but there is an obstacle in her way: namely, the evil stepmother, who does not want Cinderella to attend the ball lest she take attention away from her own two daughters. But does the stepmother say, “NO WAY, Cinderella! I’m never letting you go to the ball. I’ve got two ugly daughters I need to marry off, and the last thing I need is you, with your perfect hair and tiny feet, swanning around, making them look EVEN WORSE THAN THEY ALREADY DO!” No. The stepmother tells Cinderella, “Sure thing! Of course you can go to the ball! I’m just going to need you to clean the entryway, mop the floors, polish the silver, iron the napkins, wash all the clothes, mow the lawn, and figure out how many angels can dance on the head of a pin! And then you can 100 percent go to the ball! I’ll totally even help with your hair! So fun!”

The stepmother holds out the illusion of possibility to Cinderella, and Cinderella—who, OMG, needed Machiavelli so much more than a fairy godmother—takes the stepmother at her word and dutifully starts in on the list of tasks. Meanwhile, it’s all a win for the stepmother: She avoided an unpleasant conversation, blocked Cinderella from attending the ball, and has the cleanest floors in town.

Women in the workplace get put in this position all the time. Whereas men are typically promoted based on what people perceive their potential to be, women are typically promoted based on actual work they’ve done (usually again and again and again). This slows women down substantially in early and mid-career: Women are told they can get that promotion or raise if they just do this one more thing. Meanwhile, Randy and Jerry saunter on into the ball without so much as washing a dish.

Why is this? I put this question to Dr. Alice Eagly, coauthor (with Linda L. Carli) of Through the Labyrinth: The Truth About How Women Become Leaders. Alice says a lot of the problem is rooted in something social scientists call “confirmation bias.” That is, when people experience something that confirms a pre-held idea, they tend to remember it. When they see something that goes against their preconceived ideas, they tend to forget it or ignore it.

This makes sense. If you think Jenny is a really sweet person and she is really mean to you one day, you would tend to think that Jenny is just having a bad day, not that she’s actually a mean person. On the other hand, if you think Jill is a bad person who is out to get you, and one day she brings you a coffee, you are probably not going to think Jill is actually a sweet person and you just misread her. You are more likely to assume Jill wants something from you or, possibly, has spit in the coffee. That’s confirmation bias.

Here is how this comes into play with gender: People have strong preconceived notions about what makes a good leader, and those qualities include being aggressive, assertive, logical, self-confident, ambitious, visionary, brave, and demanding. Leaders don’t care too much what people think; they are action oriented and they are not afraid to grab the spotlight. If you look at the qualities people associate with masculinity, the crossover is almost 100 percent. An ideal man is supposed to be aggressive, ambitious, dominant, self-confident, and forceful, as well as self-reliant and individualistic. The takeaway: Being a good man and a good leader are one and the same.

Now, if you contrast leadership qualities with the qualities people associate with femininity, you see a very different picture. The qualities people associate with an ideal woman are someone who is affectionate, helpful, sympathetic, sensitive, gentle, soft-spoken, modest, and puts others first.

These are all admirable traits, but they’re not exactly qualities you want in someone who is going to, say, lead troops into battle or make a life-or-death call in surgery. The implication: You can be a good leader. You can be a good woman. But you can’t be both.

None of this is new. When Machiavelli laid out the best qualities a prince could have back in the 1500s, he named “greatness, courage, gravity, and fortitude.” The worst qualities? “To be considered fickle, frivolous, effeminate, mean-spirited, irresolute” (Chapter XIX, MPE). That’s right, being effeminate is one of the worst qualities a leader can have. You definitely don’t want a ladylike leader! The horror! The horror! Oh, how the times haven’t changed.

The result: When a man displays leadership qualities or does exceptional work, everyone remembers it and he gets rewarded. He has confirmed people’s preconceived ideas about what a leader should look like and makes them feel good about their stories. He will, in all likelihood, rise to a leadership position quickly and with great enthusiasm on the part of everyone around him. If he stumbles in that position, people are apt to dismiss it as a one-off (like Jenny on her bad day), and he’ll be given another chance or two to prove himself.

But when a woman displays leadership qualities or does exceptional work, people will often not register it, or they will see it as good work but not quite enough to justify a promotion. The woman will have to display these qualities or produce this amazing work over and over again. That’s because the woman doesn’t match the image of “leader” people have in their heads. She makes them feel uncomfortable about their stories. Think about how many coffees Jill would have to buy you before you’d assume she actually was a good person whom you had simply misjudged. Like, twenty coffees? And even that might not do it.

Of course, if the woman messes up—if she gets a shot and stumbles—she often can’t recover at all. (Imagine if Jill, amid all the coffee gifting, says something mean to you in a meeting. The dozens of free coffees would immediately fade into the background and you’d think, “Same old Jill. I knew I couldn’t trust her.”)

And this leads us to the second major issue women encounter in the workplace.
The Hotbox
This is a term I got from a particularly scarring experience on my grade school T-ball team (which was, in and of itself, a scarring experience, so you can imagine). During one game, I hit the ball off the T and took off running. I got to first base and noticed the outfielders were scrambling for the ball, so I started running for second base. Then one of the outfielders got the ball and threw it to second base. I remember the second baseman’s smug face as the ball smacked his mitt. But I was not on second base yet, so I turned back toward first base. As I ran, I saw the ball zip by my head and—thwack—the first baseman had the ball. Panting, I turned to run back to second base, when of course the first baseman threw the ball to the second baseman. This situation, I later learned, is called a hotbox: You’re not technically out, but you’re trapped in a losing situation. I ended up running back and forth between bases a bunch of times before finally giving up and walking, exhausted and trying not to cry, back to the bench.

The Hotbox is something that often happens to women in mid-career, when they start getting close to leadership positions or positions of power. The two “bases” in this case are femininity and leadership qualities, and many women end up caught between these two sets of expectations, running themselves ragged in a no-win situation.

Here’s how it works: If a woman displays a lot of qualities people associate with femininity—is empathetic, kind, helpful, compassionate, modest, and agreeable—she will be highly thought of and well-liked, but she will not be seen as leadership material. If a woman displays “leadership” qualities—is aggressive, outspoken, assertive, demanding, and independent—she might be seen as a serious contender for leadership roles, but she will not be well-liked. People will likely think of her as difficult, abrasive, and hard to get along with. They will often feel animosity and hostility toward her.

Here’s our monster: As a woman, you are in an impossible bind of expectations. If you’re kind, generous, modest, and advocate for others, you will be very highly thought of and then herded, smiling supportively, into a behind-the-scenes role where you will be chronically underpaid and loaded down with thankless work. On the other hand, if you push your ideas through and ask for more and are openly ambitious, a lot of people won’t like you, and although you might snag a management position or two, you probably won’t ever reach a top leadership role, because top leadership roles tend to require broad support from coworkers and superiors, and who wants to promote a cranky dragon lady?

Meanwhile, men, the inheriting princes, are allowed a wide range of behaviors. Just look at some of the most iconic male CEOs: the explosive genius; the geeky, distracted type with no social skills; the calculating, cold-blooded mastermind; the slick douchebag; the affable jock who drinks a little too much at the holiday party. Women CEOs don’t have these tropes. Honestly, they can’t afford to. Cranky, entitled women won’t get far. Explosive genius ladies will be sacked. Head-in-the-clouds women with no social skills will be shunted to a windowless office in subbasement C faster than you can say “THIS IS SO FUCKING UNFAIR!”

Machiavelli’s conquering prince is in a similar double bind, although his is a bit bloodier in nature. The new prince has very likely won his kingdom through battle. Now he has to win loyalty and devotion from the people he’s just conquered. Mind you, these are people whose friends and neighbors he has, in all likelihood, just slaughtered and whose barns he has probably just burned down. “The Prince cannot avoid giving offence to his new subjects…,” Machiavelli writes. “However… it is essential that in entering a new Province you should have the good will of its inhabitants (Chapter III, DTE).” In other words, to win your new kingdom, you had to do things that made the locals hate you. To keep your new kingdom, you need to get the locals to like you: Ye Olde Hotbox.
All That and Racism, Too
Being a “woman of color” means enduring all the discrimination and stereotyping white women experience on top of the discrimination and stereotyping that come with racism. The Hotbox women of color experience is particularly extreme.

Dr. Tina Opie, a workplace consultant and professor of management at Babson College, has studied workplace discrimination for decades. “Black women are the first ones to get laid off. We’re the last ones to get hired. We get paid far less than white women do,” she explains. “Our behavior and our appearance tend to be policed much more stringently.” Before going into academia, Tina worked in banking and corporate consulting and says she constantly had her clothing, hair, and mannerisms critiqued by colleagues. “I can’t even count the examples. I was told that I speak in too ‘ethnic’ of a way, because I use my hands to punctuate ideas,” she recalls. “So I’m too ‘ethnic.’ That was the word they used.”

Dr. Isabel Escobar is a professor of chemical engineering at the University of Kentucky. She says as a Latina, her emotional reactions get far more scrutiny than those of her white colleagues. Isabel is deeply committed to her work and says that sometimes manifests itself emotionally. “If I am beside myself with anger and frustration, I will cry. It’s true,” she says, laughing. “I am fully in control of what I’m saying and my emotions, but the tears just come.” When this happened at a previous workplace, Isabel says she was infantilized by colleagues: “Like ‘Calm down, Isabel. Let’s take a deep breath.’ It was parental. Like ‘Okay, sweetheart, would you like some water?’?” Isabel says it was infuriating. She was just feeling frustrated and a couple of tears had rolled down her face, and the narrative had suddenly become that she was “the hot-blooded Latina.”

Women of color will also get the message that they don’t belong in certain jobs or professions. Often these messages aren’t intentional, but they are constant. Lisa Gelobter is the CEO of tEQuitable, a software company that helps businesses address harassment and discrimination. She is a Black woman who has worked in tech for decades. Still, Lisa says she can’t even count the number of times she has been mistaken for someone’s personal assistant and asked to order lunch.

Lisa recalls one time in particular, a man from another company was visiting her workplace and asked her, “Oh, do you support Digital?”—thinking she was an assistant for someone on the digital team. “At the time I ran Digital,” Lisa says.
LGBTQ
Lesbian, gay, bisexual, transgender, queer, and nonbinary workers have an extra-tough time in the workplace. Problems with bullying and harassment—particularly sexual harassment—are extremely common. LGBTQ workers have a harder time getting hired, are often held back from promotions, and receive lower pay than their male and straight cis coworkers. Unemployment rates for LGBTQ workers are consistently higher than they are for the overall population. As a result, nearly half of bisexual and transgender women live below the poverty line.

Sharita Gruberg is the senior director of LGBTQ research at the Center for American Progress. She says data about the LGBTQ community in the workplace is pretty sobering. More than a third of LGBTQ workers say they have experienced discrimination at work. “There was one woman working in an elder care setting who was really being harassed by her coworkers,” Sharita recalls. “She had her car keyed; she had her tires flattened.” Eventually the woman was fired and was informed, in writing, that she was being let go because she was gay. The woman had no legal recourse because what the company had done was not technically illegal in her state at the time. “It was unbelievable,” says Sharita.
The Results
The Cinderella Syndrome and the Hotbox combine to create what researchers call an “accumulation of disadvantage”—a slightly lower starting salary here, a slower promotion there—and after ten years of being in the workforce, women are in a significantly different place professionally and financially than the men they started out alongside.

Consider this: Young, single women in urban areas out-earn their male counterparts, but by mid-career they’ve been left in the statistical dust. So much so that by the time they retire, they have less than a third of the savings men do and they’re much more likely to be living below the poverty line.
Machiavelli’s Lesson: Embrace the Struggle
So the monster has been looked over in all its horrifying detail: You are paid less, promoted more slowly, and harassed. You also have a more critical eye cast on your work, appearance, speech, and emotions. What now? Other than sinking into a pit of despair, where do you go from here?

To the top! And my favorite fighting words come from Machiavelli himself. Machiavelli observed that princes who had to struggle for their kingdoms actually did better in the long run than the princes who had everything handed to them. “They who… acquire with difficulty… keep with ease,” he writes (Chapter VI, DTE). Machiavelli noted that inheriting princes often lost their kingdoms because they didn’t know what to do when the going got tough: “The prince who relies entirely on fortune is lost when it changes (Chapter XXV, MPE).” Machiavelli’s lesson: Your hardships are setting you up for success—not only to get what you want, but to keep it. “Princes become great,” he writes, “by vanquishing difficulties and opposition” (Chapter XX, DTE).
Machiavelli’s Moment of Zen
No, you’re not crazy. It’s real. Discrimination in the workplace is shockingly entrenched and it holds women back in all kinds of ways. It is easy to become discouraged, depressed, and enraged when you experience discrimination and read the depressing statistics about it. That is why people don’t want to face this monster in the first place. But take heart! Inside all of that darkness is a gift: That struggle is making you strong. That might sound trite or saccharine, but Machiavelli was neither of those things, and he felt so strongly about the value of hardship, he has a rare Zen moment in The Prince of the “things happen for me, not to me” variety. “Fortune,” he writes, “especially when she desires to make a new prince great… causes enemies to arise and form designs against him, in order that he may have the opportunity of overcoming them…” (Chapter XX, MPE). That’s an extraordinary thing to say, especially coming from a man who had just lost his job and his good name, and had been jailed and tortured. Machiavelli’s conclusion: Great leaders become great because of hardship and struggle.