Work the problem: Story regret

I don't really go in for self-flagellation. Or, rather: I flagellate myself so enthusiastically while writing my stories that I don't have the time or the energy to flagellate myself once they're done. In general, I don't divide stories into Good and Bad or Perfect and Imperfect—I divide them as Finished and Unfinished.  The Finished stories are just that—stories that seemed to settle into final form before they were shipped to the printer. The Unfinished stories are the stories that were, in some way, taken away from me before they were finalized. But that doesn't mean that I didn't work hard at them and (Esquire editor) David (Granger) didn't devote his full attention to them; there's nothing I've published in Esquire that hasn't been gone over, by everyone, 10 or 20 times.

Unfinished stories are just stories that fall away from some Platonic ideal of what they might have been. In general, however, I've written so many more Unfinished stories than Finished ones—which is to say, I've written so many more stories that bear the marks of violent struggle, and were delivered by Caesarean rather than naturally. I'm quite aware when stories are coming easily and when they're not, and when they're not, I walk around with a rather low opinion of myself. But a writer is like a quarterback or a relief pitcher: You have to be able to put the bad throws behind you, or you can't do the job.

I don't flagellate myself because I'm aware that it would be crippling to flagellate myself, and the one thing I know beyond anything else is that I can't afford to cripple myself. The other thing I know is that an Unfinished story is not necessarily a bad one, and neither is a story that shows itself to be born in struggle (see Leonardo DiCaprio). Hell, even "bad" stories are not necessarily bad ones. I remember walking into a dinner party after Slate called the Angelina profile the Worst Celebrity Profile of All Time. My arrival was greeted with silence; people did not know what to say. So I brought it up, not just to ease the tension but also because I was, like my editor, perversely proud of being so honored, knowing that you can't hope to write the Best Celebrity Profile of All Time unless you are absolutely prepared to write the Worst. I'm not in this business because I expect to be admired but rather because I want the freedom to say what I want to say and get some kind of reaction for saying it, so if I can't enjoy the fact that Slate devoted 2,500 words to the Angelina profile then I've lost something of myself that I desperately need to preserve in order to write the way I want to write. The great vice of journalism in the age of social media is not its recklessness but rather its headlong rush for respectability—its self-conscious desire to please an audience of peers rather than an audience of readers—and the first step towards respectability is regret.

Several years ago, I interviewed Gong Show host Chuck Barris and he told me that anyone who says they don't have any regrets is either a liar or a psychopath. And he's right—but only about life. Not about journalism. As a journalist, I don't just (metaphorically) sing "Non, Je Ne Regrette Rien" after I write my stories. I make myself sing it, even though it's a damned hard song to sing.