Meet the Email-Retentives

“I would not be friends with someone who didn’t feel comfortable sending me offensive things,” wrote a Democratic political staffer, 23, who asked not to be named. In the next email he begged to strike that from the record because it sounded “abrasive,” even though he was being quoted anonymously: “I would be simply embarrassed to see that in there.” (He then insisted that his location within the city remain undisclosed; we will refer to him as the Staten Islander, because it’s remotely possible he is one.)

It’s a familiar dilemma to New York’s ambitious worthies: Perfect manners are suspect in private, but it’s embarrassing to be linked with jokes and ribaldry in public. And President-elect Barack Obama just raised the stakes: The questionnaire to work in his administration asks applicants to describe every embarrassing email they’ve ever sent.

Aspiring Karl Roves aren’t the only disciplined emailers among us. “I once used ‘darn’ instead of ‘fuck’ in a work email,” wrote a 26-year-old associate at a large midtown law firm; the email was to an old law school buddy.

Back in the days of Web 1.0, Euro head shrink Sigmund Freud coined a term for these people: email-retentives. While those afflicted often insist that they are victims of circumstance—employers such as Mr. Obama impose a buttoned-down ethos—evidence suggests that it goes deeper. Email-retentives probably got that way because something happened to them at the stage in their development when they were learning to use email. After all, anyone who signs on for a “fuck”-less life must have a few mommy issues.

(All of the email-retentives unearthed for this piece refused, of course, to be named. Four of them have names so generic there are more than 20 others who share it on LinkedIn alone.)

The most famous email-retentive is George W. Bush, who mass-emailed his friends in January 2001: “Since I do not want my private conversations looked at by those out to embarrass, the only course of action is not to correspond in cyberspace.” Mr. Bush is grossly embarrassing, so his abstinence seems wise. But what about all those normal-ish people who write like monks?

“In Iowa there was a staffer that got in trouble for being simply listed as a recipient of a volunteer’s offensive email,” wrote the putative Staten Islander. But that Clintonite—whose crime was receiving one of the chain emails during the Democratic primaries that asserted Barack Obama was a Muslim—wasn’t actually fired. “Not much happened,” the Staten Islander admitted.

“I’ve never actually heard of a situation where the firm read someone’s email,” said the law associate. Why doesn’t he type “fuck” at work? “Irrational fear.”

Recently a New York University law student spoke his mind to a school-wide listserv about California’s gay marriage ban and its supposed support from African-Americans. “Please stop telling me how excited I should be about Obama being elected. His campaign knew proponents of Prop 8 were using his comment about marriage being between a man and a woman in a robocall targeting certain neighborhoods to imply that Obama supported Prop 8. Did they correct this? F*&^ no!” Though the polite heretic declined to participate in this article, it’s a safe bet he doesn’t pronounce it that way in real life. But to a true email retentive, “fuck” actually feels more risque than race, sexuality and ambivalence about New York’s favorite president ever.

Nasty-yet-legal emails don’t always hurt people’s careers. State Assemblyman Sam Hoyt, Democrat from Buffalo, was just reelected even though a blogger posted dirty emails Mr. Hoyt had sent to an intern. Sure, Mr. Hoyt is banned from hiring interns. But while that sounds pathetic, interns never help people’s careers, anyway.

Five years ago, Jonas Blank was a summer associate at the white-shoe law firm Skadden, Arps. He accidentally emailed about 40 lawyers: “I’m busy doing jack shit. Went to a nice 2hr sushi lunch today at Sushi Zen. Nice place. Spent the rest of the day typing emails and bullshitting with people.” After apologizing, he was hired full-time. Skadden wasn’t alone in getting over it; Mr. Blank has since bullshitted his way into another firm.

Last spring, the law firm Paul Hastings laid off San Francisco associate Shinyung Oh, blaming her performance. She thought the real reason was money. “It shows startlingly poor judgment and management skills—and cowardice,” she wrote to the partners—and cc’d every attorney at her firm. “Unlike you, I am not just a paid mouthpiece with no independent judgment.” Ms. Oh, 37,  became a corporate hero.

“A large number of these people offered to help me find a job or to set up interviews for me at their firms or company,” she emailed us. “I see my situation as a boon.” But what if she wanted to work for the president?

“I’d bring my email as a writing sample.”

Meet the Email-Retentives