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D'oh! The Most Disastrous E-Mail Mistakes

Want some light entertainment? Check out our readers' true tales of e-mail faux pas, and find out how to prevent them from happening to you.

Robert Luhn

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Seven Rules for Gaffe-Free E-Mails

E-mail is like a digital postcard--anyone can read it. Of course, that doesn't mean you have to send that postcard to everyone on the planet. But with instant communication can come instant e-gaffes. One wrong click can drop your career or your reputation into the dumpster. Follow these rules to save yourself from embarrassment.

Rule 1: Always check the To field before you click Send.

Rule 2: Always check the To field before you click Send.

Rule 3: Always check the To field before you click Send.

Rule 4: Remember the carpenter's rule, "Measure twice, cut once," and think twice before sending once. In other words, put that message aside and let your temper (or lust) cool before you send it.

Rule 5: Use draft folders with caution. No matter what e-mail program you use, it can be easy to send an e-mail in progress by accident. Save that hot-and-heavy note on a floppy--and lock it in a vault.

Rule 6: Old news can become bad news. Find your inner Yoda (or inner editor) and pause before you write something that could come back to haunt you later. In short, avoid future embarrassment by not writing anything even remotely off color or off the cuff. When in doubt, hit the Cancel key instead of Send--and remove anything potentially mortifying. Remember, too, that deleting sent e-mails on your system is only half the story; they could be sitting out there on some server, just waiting for a subpoena. (Remember the ancient e-mails exhumed for Microsoft's antitrust trial?)

Rule 7: Don't make jokes or comments via e-mail that you wouldn't make in person. "E-mail can be a minefield of unintended insults," says Judy Heim, communications maven and longtime PC World writer. "I've stopped wisecracking in e-mail. It's too easy for comments to be misconstrued."

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