It happened to Joel Postman, a senior communications executive for a major networking company. Back in '99, he was in market development for Sun Microsystems when he composed a romantic email to his girlfriend -- then promptly sent it to the vice presidents of strategic alliances at a handful of companies.
"My hand slipped on the mouse button, and I chose the wrong email list," he admits. "One of them replied, 'We love you, too, Joel, but we weren't looking for that level of service.' It's one of those mistakes you usually only do once."
Sometimes, though, a screwup like that can help by demonstrating to the world there's a human being on the other side of the screen. That's what happened to Alex Schiff and Chase Lee, co-founders of Fetchnotes, a cloud-based notepad for recording small scraps of unstructured information.
Last January they were getting ready to announce the company's public launch. First, though, Lee decided to send a test email to his partner to make sure the formatting looked right. So he wrote an email -- "This is my test, bitches" -- and hit Send.
But Lee didn't just send that message to Schiff; he sent it to all 2,500 users of the Fetchnotes private beta. When they realized what had happened, Schiff says he began screaming at his computer.
"I thought we'd just screwed the company," he says. "We got 100 responses within the first five minutes. But when we looked at them, 99 percent said our email had made their day. My favorite ones were from users who said they had signed up for Fetchnotes and then forgot about it, but my email made them take another look."
Schiff immediately sent an apology to every user. This being 2012, he also blogged about the incident, drawing 25,000 hits and even more responses. Within a week, Fetchnotes had 500 new users, and the amount of activity on the site more than tripled.
Only two people canceled their accounts because of the profanity, he adds.
"I would never tell anyone that swearing at your users is a good idea," he says. "But having a conversational tone with our users is the right thing for a company at our stage. People appreciate the realness, if not necessarily the swearing."
True tech confession No. 2: Delete with extreme stupidityAlong with the oops email is another classic tech mistake nearly all of us have made at one time or another: the unintentional mass delete.