71F-z7iLmvLChoosing the terrain on which you meet your enemy is of paramount importance. The three truly great treatises on the art of war—Niccolò Machiavelli’s The Art of War (1521), Carl von Clausewitz’s On War (1832), and Sun Tzu’s The Art of War—are in agreement on this: battles are won before the fighting even starts by wise leaders who know which terrain plays to their strengths and which terrain plays to their weaknesses. I witnessed this often on the battlefield of the graduate school seminar.

Though we all paid lip-service to the Hydra-Headed God of Intersectionality, when it really came down to it, the working-class white guys who grew up poor (like me) would invariably (and, in retrospect, rather predictably) try to steer the seminar discussion towards a CLASS analysis of whatever we were talking about (even when it really didn’t fit); the middle-class white women tried to steer the seminar discussion towards a GENDER analysis of whatever we were talking about; and the visible minority students tried (often, alas, in vain) to get us to remember RACE.

Sometimes it felt like we were trapped in a perverse academic version of The Olympic Games, wherein we were all being forced to compete for a gold medal in BEING A VICTIM. At other times it felt like we were trapped in a dystopian intellectual version of The Hunger Games, wherein we were all being forced to tear each other apart to survive. Alas, it’s easy to see all of this as horribly cynical. But, truth be told, I doubt any of us were consciously trying to be manipulative. Privilege is, after all, for the most part invisible to those who possess it. So we shouldn’t be surprised to find a wealthy white woman who only seems to see sexism. Nor should we be surprised to find a middle-class African-American man who only seems to see racism. Be that as it may, a military man like Machiavelli might suggest that me and my fellow graduate students were all, albeit unwittingly, fighting for the higher ground.

On an actual battlefield, the high ground is usually the most desirable position. Sun Tzu stresses this, time and again: the fighting force that fails to identify and seize control of the high ground is almost always forced into a reactive, defensive position. Opportunities for offensive action are highly circumscribed. By contrast, the fighting force that occupies the high ground gets to set the terms of the engagement.

On the battlefield of the graduate school seminar, the moral high ground is the most desirable position. A graduate student who fails to identify and seize control of the moral high ground is forced into a reactive, defensive position (e.g., trying to prove that she’s really not a racist, that he’s really not a sexist pig, etc.). By contrast, the students that successfully come to occupy the moral high ground in the graduate seminar get to set the terms of the engagement. It’s a powerful position. No doubt about that. But I wonder if it’s really worth fighting for. Should we be defined by what we’ve done in the world or by what the world has done to us?

Highborn patrician Publius Clodius Pulcher unwittingly inaugurated a pernicious political tradition when he reinvented himself as Joe Average to get elected in 59 BCE. Our upper class is filled with Richie Riches masquerading as self-made men. In fact, my guess is that the number of rich people who conceal their privileged origins in 21st-century America is roughly equivalent to the number of noblemen who hid their humble origins in ancien-régime France. My friend Clayton Bailey refers to this process as “privilege laundering”. Ambitious social climbers used to invent aristocratic ancestors; these days, they fabricate histories of oppression and talk incessantly about their underprivileged ancestors. Plus ça change, plus c’est la même chose.

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We hear a great deal about privilege these days—as well we should. After all, privilege is an excellent predictor of whether or not you’re going to succeed in life, and privilege is distributed unequally in our society—indeed, increasingly so. Though no amount of privilege can guarantee that you’ll succeed, the more privileged you are, the more opportunities you get. It’s sort of like buying lottery tickets at the dépanneur. You can buy a 100,000 scratch tickets and still win nothing. But, chances are, even if you don’t win the grand prize, if you’ve got 100,000 tickets, you’ll probably win something. At any rate, you’ll have a much higher chance of winning something than the guy who can only afford to buy 10 scratch tickets. Still, it’s important to note that strange and improbable things can happen to the underprivileged just as they can happen to the extremely privileged. For instance, just as it is possible for someone with 100,000 tickets to win nothing, it’s possible for someone with just 10 tickets to win everything. But it’s not bloody likely!

George W. Bush’s circuitous path to the presidency is a case in point. Bush was a screw-up and a royal pain in his family’s ass well into his late twenties. He messed up again and again and again (e.g., with DWI charges, cocaine abuse, alcoholism, womanizing, etc.), and yet he was still able to turn things around and come out on top. By contrast, a poor kid from Baltimore—born to a teenage, drug-addicted, African-American mother—has very little privilege. He gets very few of the proverbial lottery tickets. He can do everything right and yet still fail. What’s more, if he screws up even once, he can lose everything. For instance, a major cocaine-possession charge could land him in prison for the better part of a decade. When he gets out (if he gets out) his chances of getting a decent job as an ex-con will be severely circumscribed for years to come.

Inequality is a serious problem which threatens the very fabric of our way of life. We ignore it at our peril. Even so, there are disadvantages associated with privilege, real and measurable disadvantages, which we hear about but rarely these days. A notable exception to this rule is to be found in Amy Chu and Jed Rubenfeld’s The Triple Package: How Three Unlikely Traits Explain the Rise and Fall of Cultural Groups in America (2014). Chu and Rubenfeld identify three groups—Mormons, Jews, and Chinese—that have consistently out-performed White Anglo-Saxon Protestants (WASPs) in the last three decades. Their explanation is as follows: exceptionally successful groups—such as the Mormons, the Jews, and the Chinese—inculcate all three of these traits in the young: a sense of superiority, a sense of insecurity, and a well-developed capacity for impulse control.

Though they get a great deal, there’s one thing that wealthy WASP men—by far the most privileged group in our society—don’t get these days: and that’s The Triple Package. Sure, they’re taught to see themselves as better than everyone else (especially if they go to private school). But they’re no longer taught how to control their impulses—not consistently, or as a matter of course. Alas, the description of the Protestant work ethic—made famous by the great sociologist Max Weber in The Protestant Ethic and the Spirit of Capitalism (1905)—applies to precious few Protestants these days; it does, however, apply to a whole lot of Mormons, Jews, and Chinese. Still, impulse control isn’t the wealthy WASP man’s weakest suit. His lowest scores are to be found in the second category: sense of insecurity.

The wealthy WASP man has a profound sense of entitlement. He’s been brought up to believe that everything is going to come to him rather easily. He’s optimistic about his future. It’s all going to fall into place somehow, though he couldn’t really tell you specifically how or why. Truth be told, he doesn’t stress about it too much; he’s pretty chill about the whole thing. And that’s why he’s probably destined—at best—to live a lackluster life of middling mediocrity. It’s precisely here, according to Chu and Rubenfeld, that privilege ceases, to some extent, to be a privilege, because it makes you lazy, passive, arrogant, smug, sloppy, and complacent.

This will come as no surprise to anyone familiar with the works of Nassim Nicholas Taleb. In Antifragile: Things That Gain from Disorder (2012), Taleb argues that living things (biological systems) don’t just tolerate stress; they actually need it just to maintain the status quo. For instance, as N.A.S.A. discovered a few years ago, much to their chagrin, the bones of astronauts in a space station quickly degenerate when they’re deprived of the regular stress provided by the Earth’s gravitational field. Likewise, my friend’s muscles atrophied rather severely whilst she was recovering from surgery. Three months on a hospital bed, with very little movement, caused the muscles in her legs to degenerate so much that this former marathon runner could barely walk when she was discharged from the hospital. I remember it vividly: we had to practically carry her to the car.

If it’s true that we need a certain amount of stress merely to maintain the strength that we presently possess, it’s equally true that we need to increase the amount of stress on a biological system if we want it to get stronger (e.g., by lifting weights). What’s more, as Taleb puts it, society’s winners (the rich and powerful) are often “punished by privilege and comfort.” By depriving the most privileged people in the world of necessary stressors we inadvertently harm them. Alas, muscles that are unused atrophy, bones that are unused become brittle, underutilized immune systems grow weak, and self-satisfied elites become, well, beach bums.

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Nietzsche was right: life without music really would be a mistake. It reminds me, as well, that gifted musicians can smooth the edges off of any sharp rock: and envelop the most unbearable sources of irritation: in something pearly, and divine. Like oysters, they can transform that which causes them pain into a Pearl of Great Price. Perhaps this is why the greatest sufferers produce the smoothest art, whilst those whose afflictions are comparably small—“mosquito bites of the soul” (to borrow Nietzsche’s phrase)—produce the harshest art. Although Billie Holiday’s bearing witness to one of the great horrors of the 20th century in “Strange Fruit” (1939), she does so with a sly sweetness that’s simply sublime; meanwhile in the waiting room, the whiny adolescent pop star on the radio, whose name escapes me, makes his garden-variety suburban middle-class problems seem like the end of the world! Like Baileys Irish Cream, his pain is intoxicating but it’s not particularly strong. He can drink it straight. Great sufferers like Billie Holiday and Amy Winehouse cannot. They need to mix the fire-water of their pain into something sweet, to make it palatable.

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I learned about white privilege from the streets, not the classroom. My teachers were teenage criminals who spoke in plain, easily-accessible English (or French), not jargon-laden academics with PhDs in sensitivity. The lessons I received from them were practical and experiential, not theoretical. And they made me pretty good at stealing stuff for a spell. Like many bratty kids from my neighborhood, I went through a shoplifting phase when I was a teenager. Like many other social animals, such as wolves, my friends and I hunted in packs and employed a coördinated strategy that played upon the weaknesses of our prey.

Our intended prey was the store staff; their racial prejudices were the weaknesses we exploited. We were four, more often than not: one black kid and three white kids. After carefully choosing a store, we’d enter it separately. The black kid would immediately attract all of the staff’s attention. It was amazing! The kid didn’t have to do anything suspicious. Didn’t have to smell like weed. Didn’t have to dress like a thugged-out rapper. Didn’t have to wear dark sunglasses. Nothing. He just had to be black. That was enough. The staff would be totally fixated on the black kid and follow him around the store while me and the other three white kids robbed the place blind. The four of us would meet up about an hour later, usually at a metro station, and divvy up the spoils. Incidentally, the dude who finally caught me at Galeries d’Anjou was a sweet, middle-aged Haitian guy. He caught me and my degenerate friends precisely because he wasn’t blinded by racism.

I met my black doppelgänger at a rooftop party in Baltimore. It was 2000 and we were both 25. We had the same metrosexual mannerisms, same ridiculously loud laugh, same taste in music, same taste in literature, same strange obsession with snakes and salamanders. But it gets weirder still: because, as it turns out, we were both raised by single-moms on welfare, in rough neighborhoods. Both of us went through a super religious phase in our early teen years, followed by a troublemaker phase. Both of us changed schools often and repeated the 10th Grade. I could go on and on: it was eerie. And yet our lives couldn’t be more different: I was in Baltimore on a full scholarship, in a PhD program at Hopkins, whilst he had just gotten out of jail. Six days ago! He’d been in prison for the last seven years—seven years!—for drug offenses that wealthy Hopkins undergrads regularly get probation for.

My life could have been his life. But it wasn’t. And it isn’t. Because I grew up in Canada. And he grew up in Baltimore. Because I grew up white. And he grew up black. Because I grew up in a place where poor kids get to go to well-funded public schools that provide them with a high-quality education, an education which can take them wherever they wish to go. And he grew up in a place where poor kids are forced to go to crappy public schools which are crumbling, crowded, and chronically underfunded—schools that provide even their best students with a substandard education that hobbles them for life. Because I grew up in a public housing project that was clean and affordable—a place that allowed us to live our lives with a certain amount of dignity. And he grew up moving from one overpriced cockroach-infested shithole to the next. Because I grew up in a place where poor kids get the same universal healthcare available to children of the rich. And he grew up waiting nine hours to see a nurse at the free clinic. Because I grew up in a place that gives bratty kids lots and lots of chances to get their shit together. And he grew up in a place where a few stupid mistakes can seal your fate for years.

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There have always been assholes who cut in line at the amusement park, but Six Flags Entertainment Corporation has recently made it legal for them to do so: “With THE FLASH Pass Platinum your reservation reduces wait time by up to 90%! It also includes 2X — where you can enjoy selected rides TWICE IN A ROW without leaving your seat!” If you’re willing to pay extra, you can actually buy the right to cut ahead of sweaty parents who’ve been waiting in line with antsy kids for an hour or more. FLASH passes reek of the Ancien Régime and they’re probably bad for business. Just as private schools undermine our public school system, and two-tiered healthcare systems undermine our public healthcare system, FLASH passes undermine our faith in the price of regular admission. When pretty much everyone is getting some sort of discount, the regular price starts to look like a lie. Regardless, even if I could afford to get my kids FLASH passes, I wouldn’t do so for fear that it might turn them into entitled little assholes. Think about it, what kind of message are you communicating to your kids when you buy them a FLASH pass? Rich people don’t have to be patient. The regular laws of the land don’t apply to you when you’ve got money. You’re more important than the other kids because your parents happen to be rich.

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I read Hans Christian Andersen’s “The Princess and the Pea” (1835) when I was a kid. Like most of you, I thought the princess was a spoiled brat. But today, at 43, I find myself sympathizing with the princess. She’s a victim of her wealthy upbringing. The girl needs perfect conditions just to get a good night’s sleep: “In the morning she was asked how she had slept. ‘Oh, very badly!’ said she. ‘I have scarcely closed my eyes all night. Heaven only knows what was in the bed, but I was lying on something hard, so that I am black and blue all over my body. It’s horrible!’ Now they knew that she was a real princess because she had felt the pea right through the twenty mattresses and the twenty eider-down beds. Nobody but a real princess could be as sensitive as that. So the prince took her for his wife, for now he knew that he had a real princess.”

In our day and age, the princess in Hans Christian Andersen’s “The Princess and the Pea” would grow up to be the kind of woman whose morning is ruined if the new guy at Starbucks messes up her soy-latte; the kind of delicate flower whose entire day is ruined if her favorite yoga instructor calls in sick; the kind of therapy-junkie whose entire week is ruined if her therapist cancels her weekly appointment; the kind of absentee-parent who has a panic attack when the nanny quits because she really doesn’t know how to take care of her own kids. Privilege isn’t always a privilege. And she’s a case in point. Wealth and power have transformed her into an inflexible wimp. Look at her: she’s pathetic. Why do you envy her? You really ought to pity her.

When our sons were babies, many marveled at how easily they could sleep through ambient noise. When asked, my wife was happy to share the secret: “If you give your baby a perfectly quiet environment at bedtime, your baby will come to need a perfectly quiet environment to go to sleep; if you give your baby a perfectly quiet environment all through the night, your baby will come to need a perfectly quiet environment to sleep through the night.” As we now know, this principle of desensitization applies to much else (e.g., allergies, stress, losing at games, etc.). Pampered princesses become pathetic pansies who can’t sleep on peas.

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“Man is born free, and everywhere he is in chains.” Every college graduate knows that the philosopher who penned this line was profoundly moved by the plight of the poor. What’s less known is that the author of The Social Contract (1762) was equally adept at sympathizing with the plight of the rich. Jean-Jacques Rousseau spent a great deal of his adult life hanging out with the idle rich. So he knew full well that most of them were bored and miserable. But he didn’t think wealth was the problem. The problem was that they spent their money unwisely.

In one of the most fascinating thought experiments in modern philosophy, Rousseau imagines—near the end of Émile (1762)—what it would be like to be rich: how he would and would not spend his money, how he would and would not spend his time. What’s striking about his dream is that it’s nothing like the gaudy adolescent male fantasies found in rap videos. There are no pool-side parties in Rousseau’s reverie. No bikini-clad babes. No gold. No glitz. No bling.

Many “If-I-Won-the-Lottery” fantasies envision moneyed life as a kind of never-ending spa-day, wherein the pampering just goes on and on and on. But Rousseau clearly has little use for this kind of comfort. The opulent mansions showcased by Robin Leach on Lifestyles of the Rich and Famous are notably absent from Rousseau’s account.

Though he can now afford a palace for a dwelling, Rousseau tells us that we’ll find him in a modest home. His reasoning is as follows: Big houses require a great deal of cleaning and maintenance. So when you buy a big house, you’re not just buying a big house; you’re also buying the small army of maids, gardeners, and handymen that of necessity come with it. The rich, he quite rightly observes, are rarely alone. All to the contrary, they’re usually surrounded by a cloud of paid strangers—strangers who rob them of privacy, peace, quiet, and solitude. Rich people complain about this often. Yet few seem to realize that the problem is entirely avoidable. Rousseau will not make this mistake when he’s rich.

Though he can now afford a fancy horse-drawn carriage and a driver, Rousseau says he will continue to walk pretty much everywhere. He will also continue to do his own shopping and run his own errands. Why? Because it’s good to get out of the house and get some exercise. What’s more, it’s often entertaining and instructive. The idle rich are bored in large part because their lives are far too sedentary. Even as a rich man, he will live by the following maxim: “we ought to receive from others only those services that we cannot get from ourselves.”

Rousseau wants to purchase two things with his riches: leisure time and freedom from drudgery. And he wants to spend as much time as possible with his friends and family—with people, that is, who love him and enjoy his company, as opposed to people who are paid to do things for him. Aside from Seneca, I can think of no other philosopher who more clearly understood how to avoid the pitfalls of privilege.

—John Faithful Hamer, Being a Philosopher in Social Media Land (2017)