You're not expecting too much of Malcolm Gladwell. Where I come from—university press publishing—one philosopher explained pages of arguments accompanying a favorable recommendation: "Philosophers show respect by disagreeing with each other." Physicist Wolfgang Pauli put it more negatively about a junior researcher's paper: "Not even wrong." So, we should welcome Gladwell neither as a genius (a concept he dislikes, anyway) nor as a mere packager of others' ideas. Instead, let's treat him as a colleague who deserves careful attention.
Outliers isn't wrong, but neither is it necessarily right. Gladwell doesn't see, for example, that some outliers were just the first ones to seize a unique opportunity that others could not share—a "positional good," as economist Fred Hirsch called it in his book Social Limits to Growth. After ridiculing the idea of buying "a shiny new laptop" for every student, he asks rhetorically, "[I]f a million teenagers had been given unlimited access to a time-sharing terminal in 1968" like Bill Gates, "how many more Microsofts would we have today?"
Some academic reviewers have also dissented from much of the research Gladwell cites. One of his favorite sources is historian David Hackett Fischer's Albion's Seed, which he uses to argue the strong persistence of values in American regional cultures over four centuries. The work, rightly admired for its rich scholarship, has also been blasted for its selective use of evidence to support its thesis. Fischer's idea (repeated by Gladwell) that the cult of honor in the U.S. South originated in medieval British border disputes has also been questioned. According to Bertram Wyatt-Brown, author of the standard work Southern Honor, "colonial and backcountry historians in general stoutly reject" Fischer's book.
Cultures change more rapidly and thoroughly than Fischer and Gladwell acknowledge. Think of the cosmopolitan, lively Spain that followed the grim Franco years or the hypercapitalist and individualist China that came after Mao. What about postwar Germany, which now rates much lower on indexes of authoritarianism than France, at least according to one of Gladwell's notes? Or, for that matter, consider the changing values represented by Barack Obama's election victory that you mention, John, which overthrew structuralist dogmas of "blue" and "red" states and fears of concealed racism.
Obama's story has another dimension strangely neglected in Outliers: his abandonment by his father, the death of his mother, and his struggle for a new identity. The successes cited by Gladwell, including his own mother, go from strength to strength; cultural forces and good luck come together. Yet for all Obama's elite education, his years as a community organizer in Chicago while others of his age were launching lucrative careers only conforms to the "accumulative advantage" model endorsed by Gladwell in hindsight.
There isn't much suffering, for the sake of art or anything else, in Outliers. People fortunate enough to be born in the right time, place, cultural group, and profession are borne along by the current. Yet among previous presidents, even upper-class outliers had a lot to overcome. Think of Theodore Roosevelt's lifelong respiratory problems, Franklin Roosevelt's polio, John F. Kennedy's childhood scarlet fever and his war injuries. (When Kennedy said that life is unfair, he was referring to health and sickness.) John McCain's captivity was his own turning point, as PT-109 was Kennedy's. Americans aren't the only politicians to be proud of fighting adversity. Nicolas Sarkozy, with a multiethnic family tree and an absent father like Obama's, once declared, "What made me who I am now is the sum of all the humiliations suffered during childhood."
Gladwell credits some of J. Robert Oppenheimer's success to the aristocratic social skills he absorbed from his family. But there was another side of Oppenheimer, revealed when he contracted tuberculosis as a young professor and retreated with his younger brother Frank to the hills of New Mexico; his fascination with Los Alamos began during that interlude. When Oppenheimer took his Army physical before receiving his commission in 1943, he was nearly disqualified as 11 pounds underweight with a chronic cough. But according to Gladwell's main source on Oppenheimer, Kai Bird and Martin J. Sherwin's American Prometheus,the physicist was able to withstand the stress of preparing for the hearings on his security clearance; as his secretary later recalled, he "had that fantastic stamina that people often have who have recovered from tuberculosis. Although he was incredibly skinny, he was incredibly tough."
Misfortunes are not like cultivated homes and great schools; their effects are unpredictable, energizing some and crushing others regardless of social class and education. In rejecting the myth of self-made men and women—and very properly revealing all the help most of them had—Gladwell also ignores important, if often mysterious, realities of endurance.
John, if our economic emergency is as serious as it appears, "accumulative advantage" will matter less and dealing creatively with crises will count more. And if this sounds like the old-style success books that Outliers is trying to replace, I can only recall an aside made by historian of science Charles C. Gillispie in my college History 101 course: "There is nothing more embarrassing to the educated mind than a true cliché."