Malcolm Gladwell: Guru of the Underdogs

His latest gospel of success further romanticizes the Davids of the world and underrates the Goliaths.

Mickey Duzyj

So David had the advantage all along. His victory was not a miracle; the slingshot was the superior weapon. Goliath’s size and heavy armor—his assurance of victory in a close-contact battle—guaranteed that he couldn’t lumber out of the way of a rock traveling 34 meters a second. David won by turning Goliath’s great advantage into his undoing. Therein lies an exhilarating moral, says Malcolm Gladwell, and he proceeds to spin illustrative tales about “underdogs, misfits, and the art of battling giants,” as the subtitle of his latest book puts it.

Gladwell, who half a decade ago brought us tales of top dogs in Outliers: The Story of Success, is still worrying the same bone: Who gets ahead, and how? His own story exemplifies one tried-and-true formula: keep asking that question and offering inspirational anecdotes as answers. In Outliers, he promoted what he has called “an amazingly hopeful and uplifting idea.” Don’t be fooled by the meritocratic myth that success is the product of God-given qualities such as intelligence and talent. In fact, Gladwell argued, the achievements that we chalk up to natural ability or individual resolve owe a great deal to factors we underappreciate: historical timing, the career paths seized by immigrant parents, family wealth, the opportunity to put in thousands of hours of practice. Society has more control over who succeeds than we imagine; our talent pool could be much bigger than it is.

As plenty of reviewers pointed out, there was a flip side to Gladwell’s upbeat message. For genetic determinism, he swapped in cultural determinism—hardly the liberation it seemed. The hidden factors he played up in his account of success are distributed, if anything, even less fairly than talent and intelligence. And the income and class distinctions that govern their allocation are rapidly becoming more inequitable.

But Gladwell is not one to be daunted. In David and Goliath, he’s armed with fables chosen to dispel such fatalism. What we assume to be entrenched advantages, he says, don’t always offer the edge we may expect: top dogs beware. What’s more, personal hurdles, family troubles, social inequities—though they may look like disadvantages—can propel misfits further than risk-averse meritocrats dream. In his pages, the underdogs win, mostly by dint of the sort of upstart individual agency he downplayed in Outliers. Of course they do. That’s why Gladwell includes their stories. Yet you’ll look in vain for reasons to believe that these exceptions prove any real-world rules about underdogs. In life, it’s hard to turn obstacles into blessings, and giants are by now adept at the art of battling insurgents.

The story most likely to resonate with Gladwell’s audience addresses the plight of anxious overachievers, rather than the predicament of the truly disadvantaged. Always at the top of her class in her public high school outside Washington, D.C., Caroline Sacks (a pseudonym) had pursued an avid interest in science since childhood. She chose to attend Brown rather than the University of Maryland—and because she went to a great university instead of a good one, Gladwell argues, she ended up abandoning her goal of a science degree.

She “had never not excelled” academically. But at Brown, her organic-chemistry class gave her “just this feeling of overwhelming inadequacy.” Sacks dropped science and switched to liberal arts. If she’d gone to Maryland, Gladwell says, she would have been spared a crisis of confidence and never would have veered away from a field that she loved—and that promised a more lucrative future.

But just because many successful people struggled growing up doesn’t mean, alas, that many people who grew up struggling are successful.

The moral of the story is not exactly that underdogs will triumph: quite the contrary. To switch to another of Gladwell’s favorite metaphors, the point is that being a big fish is very helpful, even when picking the small pond means forgoing the high-status allure of the big pond. Second-rate schools can promote first-rate achievement, whereas more-selective environments can squelch it. For example, Gladwell cites a study showing that, in the first six years after receiving their doctorate, research economists published more, and in more-prestigious journals, if they had been standouts at a bottom-tier school than if they had been not-quite-stars at the best schools.

It’s a bracing corrective to our hyper-meritocratic obsession with the college rat race. (And if Gladwell’s right, I can save myself several hundred grand when application time rolls around for my three kids.) But more to the point, in a book about underdogs, what does Gladwell’s discussion of Sacks’s story really have to say to those with further to climb? In an endnote, he teases out the implications of the idea for affirmative action—a subject he also addressed in Outliers, in a notably different spirit. There he invoked a University of Michigan Law School study that tracked the fates of some of the school’s minority students, whose undergraduate GPAs and scores on the LSAT tended to be lower than those of their white peers. Graduates went on to do every bit as well as their white colleagues in the real world—evidence for Gladwell that in elite-school admissions, the academic ranking of qualified applicants is irrelevant. Here he cites a study comparing two groups of black students who got into elite law schools thanks to affirmative action. One group enrolled, and the other instead ended up at second-choice schools. The students who attended the good-but-not-great schools were far more likely to graduate, pass the bar, and become lawyers, Gladwell reports. Now he emphasizes that special boosts may backfire.

If there is a lesson here, it is to be cautious when deriving neat rules about “the Power of Context,” a phrase from Gladwell’s earlier book The Tipping Point. He doesn’t square Sacks’s story with evidence of the perils of so-called undermatching, when students aim lower than their qualifications would suggest. We don’t learn whether Sacks needed financial aid, but many high-performing, low-income students never consider applying to schools like Brown. Instead they go to nonselective schools close to home. But there they do worse than comparable students do at elite schools, and they drop out at higher rates, largely—though not only—because of cost. Among other things that a place like Brown can offer is an aid package that may make the tuition more affordable than even in-state prices.

Sacks’s tale doesn’t line up with Gladwell’s other stories either, which converge on the opposite theme. She dropped out of her difficult science major at Brown because she felt inadequate. Many successful entrepreneurs, we learn from David and Goliath, are dyslexic and felt stupid growing up. But they didn’t quit or lose confidence. They struggled, developing compensatory strategies that spurred them onward. In the same vein, Gladwell reports that a disproportionate number of eminent people—including British prime ministers and American presidents—lost a parent in childhood. It’s yet more grist for the romantic view that early wounds beget winners. Except when they don’t: as Gladwell notes, almost in passing, prisoners are also far more likely than the general population to have suffered that blow as children.

Gladwell calls Sacks’s troubles an “undesirable difficulty … But there are times and places where struggles have the opposite effect.” Which times and places? How do we distinguish a desirable difficulty from an undesirable one? What turns an underdog into a prime minister rather than a gang member? Gladwell doesn’t attempt to explain—but we know the answer. What can transform a handicap into an advantage is having other advantages. If you are intelligent and blessed with loving parents able to provide you with the right education, and you find sources of confidence to draw on, then it’s possible you could end up like Gary Cohn, one of the dyslexics Gladwell profiles: he’s the president of Goldman Sachs. But just because many successful people struggled growing up doesn’t mean, alas, that many people who grew up struggling are successful.

As for the art of battling giants, by now the secrets of insurgents’ success are more widely known—not least to the giants—than Gladwell gives signs of appreciating in his chapters on armies, governments, and political movements. The moral of the stories he tells may have been lost on the Philistines, but has since sunk in: more is not always more. Gladwell tells how the British Army fueled rather than quelled the Irish Republican Army’s defiance with its heavy hand in Northern Ireland in the 1970s. He describes civil-rights activists in Birmingham using political jujitsu—turning an opponent’s overwhelming force back against him—when they lured Bull Connor into setting attack dogs on peaceful teenagers, producing photos that appalled the world.

But that was half a century ago, and the tactics have been refined—and countered and codified—since then. “Sometimes, the More Force Is Used, the Less Effective It Is,” says The U.S. Army/Marine Corps Counterinsurgency Field Manual, warning that disproportionate power can undermine political legitimacy. The advice, published by the military in 2006, may not always be followed, but it is a major lesson of the manual—surely the very definition of conventional wisdom. Claiming the political high ground is the goal, which is indeed one that the Davids of this world can achieve with flexibility, creativity, patience, and intense commitment.

But it is much easier for the Goliaths to do so. Superior force is a disadvantage only because it often blinds a giant to all other strategies. Deployed without subtlety, it favors the enemy. Yet disproportionate power, guns, and money, when used intelligently and in the service of building legitimacy, are rather effective. The race is not always to the swift, nor the battle to the strong—Gladwell is right about that. Betting on their victory, though, is still the way to go.