Debra Pickett

The major difference between New York, where he worked for Vanity Fair magazine, edited by the mercurial Graydon Carter, and Hollywood, where he almost had a production deal with a major industry figure he doesn't name, is that, "L.A. chewed me up in a few months. New York took five years."

Young did not set out to fail. Nor, really, did he set out to make a living by entertaining people with stories of his failure. His original concept for the first book, he says, was a kind of intellectual history of Vanity Fair. And for the second, he'd hoped to write a novel.

But once How to Lose Friends took off, Young's fate -- and literary persona -- was sealed.

'I'll kill you'

"Heroic failure is a very British concept," says Young, who now lives in London with his wife, Caroline, and two young children. But it was something of a surprise that American readers were drawn to Young's stories about his hapless efforts to impress Carter and make a name for himself on the New York scene. "Generally," he says, "there's only one kind of loser in America."

Young's memoir, though, hit a perfect revival-of-the-slacker, post-dot-com moment, when lots of would-have-been-hipster-superstars were busy licking their wounds and plotting their Next Big Move. Even he was surprised by its success.

As soon as it did hit the best-seller lists, though, Young began plotting how he might exploit its success and parlay his new standing into a certain level ("probably D-list") of celebrity. That's when he headed for Los Angeles.

And he swears that he wasn't trying to make a mess of things there. In fact, he had no problem promising that he wouldn't name the big-deal producer who was interested in his movie.

"He told me, 'if you write about me, I'll kill you.' And I was widely advised that he would, too," Young says. "Anyway, when I promised him, I really meant it. At the time."

In retrospect, of course, the quick crashing and burning of the movie project was a reasonably good outcome for Young, who, at the very least, got material for a book out of it. He's come to realize, by now, that, with his loser persona, "mild success is the worst possible outcome."

Life becomes a little strange when failure is your gig. So, though Young still resists thinking of himself as a memoirist, he has started keeping a journal.

"If something goes horribly wrong," he says, with a sarcastic twinkle in his eye, "like if my wife leaves me or something fantastic like that . . . ."

Some success

Meanwhile, though, he inhabits a reality-show-like level of almost famousness. Though he is not a "proper celebrity," he finds himself frequently asked to do things like appear on Celebrity Big Brother or, even more alarmingly, Celebrity Detox. And, in addition to the new book, he's writing a restaurant column for one London paper and a theater column for another. He's also mounting a play -- a farce about the royal family -- and, in a brilliant irony, still working toward some success as a screenwriter.

The screenplay of How To Lose Friends "actually seems to have some momentum" at the moment, he says, with names like Bill Murray and George Clooney being mentioned as possible Graydon Carters.

And if that doesn't work out, Young has also joined The Writers' Circle, a workshop of British writers who have all succeeded in other genres and are now working on screenplay projects.

"All the top people have come to talk to us," he says, sounding uncharacteristically star-struck. He recovers himself quickly, though, and adds, "Of course, they've all said different things."

He begins to list off what he's learned about crafting a story and working within an established genre. Then he seems to stop himself, as if realizing an inherent absurdity in what he's saying, given the box office success of, say, ''Pirates of the Caribbean.''

"Maybe inelegant and uncrafted with a plot as dense of Coriolanus is the way to go," he muses.

It's hard to tell if he's talking about a recipe for success or one for failure. Or if, for Young, there is really much of a difference.