If you haven't done so already, check out Matthew Scully's fascinating essay about former White House speechwriter Michael Gerson. It's from September 2007, but it wasn't freely available online until last week, when The Atlantic's paywall came down.
Most people would say that Gerson comes across rather poorly in the piece: self-involved, self-promoting, and downright dishonest. He hogs credit for success and sticks colleagues with blame. He craftily courts media attention, while keeping his fellow writers out of the limelight. In short, he's a bit of an a**hole.
But I have to confess to no small admiration for Gerson, as well as the many other highly successful people who have risen to the top of their fields by being nasty, ruthless, and Machiavellian. E.g., Anna Wintour of Vogue, Hollywood producer Scott Rudin, super-agent Ari Emanuel of Endeavor (the model for Ari Gold of Entourage), and numerous Biglaw partners (Dennis Block of Cadwalader immediately comes to mind).
I often wish that I could be more like these people. Unfortunately, my weakness for the affection and approval of others -- i.e., my overwhelming desire to be liked -- prevents me from rising to their level of fabulous d-baggery. [FN1]
Of course, how much their personalities contribute to their success is open to question. Do such people succeed because, or in spite of, their a**hole-ishness? Is it that they're really great at what they do, so people will tolerate their being less-than-nice? Or are their conventionally unappealing traits -- nastiness, underhandedness, disregard for the feelings of others -- a critical part of their success? I lean towards the latter theory, but I'm open to persuasion.
[FN1] To be sure, I'm sometimes snarky when I blog. But occasional irreverence online is a far cry from rampant, in-person, face-to-face a**holery. I can't pull off the latter; I'm "too nice" in person. I smile, I laugh, I avoid argument and confrontation. People are often surprised by how my online persona diverges from my in-person persona.
Present At the Creation [The Atlantic]