Is there anything more horrific in these modern times than an erroneous reply all, an in-progress draft that gets sent, or a mistaken cc:? The answer is yes, there are many things that are much worse. However, nothing is quite as embarrassing.

Consider the case of Ben Sherwood, the newly-announced president of the Disney/ABC Television Group. Back in 2004, when Sherwood was executive producer of Good Morning America, he sent an encouraging holiday email to his employees lauding them for their work. Unfortunate for him, he also attached the editorial comments from his wife from when he was drafting the email.

A pretty harmless mistake, unless you count the use of “doll”as harmful to one’s image. Some of you would. But an email that gets sent to the masses when it was intended for only one recipient can also be a motivator. Take Bill Cochran, for example. A creative director for ad agency Richards Group, he successfully pitched a Super Bowl commercial to Bridgestone Tires in 2010, and was looking to repeat his success in 2011. When an email from his boss jokingly pitted employees against each other for landing a successful Bridgestone pitch, Cochran meant to reply to just his art director with a derisive email about his fellow competitors.

Instead, he emailed his trash talking response to the entire company. Cue panic. After being thoroughly embarassed, Cochran turned the experience into his ad pitch. It went on to become the 2011 Bridgestone Superbowl commercial. 

In fact, a lot of humor can come out of a mistaken email chain. When Hollywood producer Nathane Kahane moved offices, his assistant sent an email notifying the A-list clients in Kahane’s list of contacts. His mistake was in cc-ing the recipients instead of bcc-ing. Huge celebrities like Judd Apatow and Warren Beatty were treated to an email chain comprised of humorous reply-alls from people thoroughly enjoying the mistake, with Apatow leading the way.

Here’s the thing. We’re all familiar with the pitfalls of email, so there’s a certain amount of forgiveness when a co-worker accidentally loops everyone in on their private business. In some instances, it even leads to a Super Bowl campaign. Mostly, though, it’s just embarassing. So do yourself a favor. If Google’s Gmail is your preferred messaging medium, check out the slideshow above to turn on the “unsend” feature.