I never thought much of Malcolm Gladwell, maybe because he reminded me entirely too much of Desmond Morris for his own good. Morris wrote The Naked Ape, in which he tried to use argument-by-analogy to draw rather shaky and tenuous connections between men in civilization and animals in general. Much of Morris's work was based on conceits about animals that were developed by observing them in captivity, which is a little like doing a general study of human child development and only using children born to parents in prison as the sample pool.
Gladwell's arguments are not much better: he creates a theory, and then uses singular examples as evidence for the theory, instead of looking at the evidence first. To wit: Blink, his book about the "science" of intuitive decision-making, which got savaged by Wesley Cecil in April 2006 Skeptical Inquirer. The opening anecdote for the book, about how an art expert saw in a second that a given piece of art was a fake after others had labored over it for long periods of time, doesn't even support his case.
Ditto Outliers, which used a similarly anecdotal approach, and suffered from the same flaws. The ideas expressed in each book are intriguing: Blink purports to deal with how people can make instant assessments of a situation, while Outliers tries to explain why certain people are successful and others are not — although the biggest wisdom you'll mine from the former is that some people are really good at making instant assessments of a situation (or not), and from the latter it's that some people are successful and others are not. In short, the books do not really explain anything, which not surprising given that they are mainly marketed to businessmen and not laypersons curious about science.
Outliers comes even closer to Morris's "man is an animal so why bother civilizing him" jungle turf.
The real question is, to what degree are we allowed to strive for things not immediately provided by our existing environment? That's a more nuanced question, and one that deserves a good book, but from what I've seen Malcolm Gladwell isn't going to be the one writing it.