3 excruciating email blunders we never recover from

You’ve most likely fallen prey to a missent email at some point in your career (darn you, Reply All).

While a quick “sorry!” follow-up is usually enough to quell any issues, sometimes that one email sent by accident can have bigger repercussions for your job or reputation—and five professionals are breaking down what happened when they did just that.

What are the biggest takeaways they have for you the next time you’re tempted to send that mean message about your boss or forward something on an email chain? Here are the three most important lessons they learned.

1. If It’s Personal, Say It in Person

Anna, a high school English teacher, says she and her fiancé got into a pickle after he tried to invite a specific co-worker to their destination wedding—and he accidentally sent the email to the whole office.

“He felt awkward for the next few days as he fielded wedding questions from his co-workers, some he hardly knew,” she says.

The lesson? “After that, he realized it was easier to just talk about personal things in-person or at least through text message.” It’s easy for things to get off-track when you’re sending dozens (if not hundreds) of emails per day, so take it offline as often as possible.

2. Don’t Vent Online—Ever

When she was in grad school, Briana, a PhD candidate, had a frustrating professor who decided last-minute to make her turn in a paper when she was trying to work on her dissertation proposal.

“I wrote a lengthy email to my friend venting all of my frustrations…or so I thought. Instead of hitting ‘Forward,’ I had hit ‘Reply,’” she recalls. “Unsurprisingly, it did not go over well.”

Briana isn’t the only one to take the “vent online” approach and have it nearly backfire. Damian, a full-time writer, once meant to sent an email to a small group of co-workers criticizing a recent email their boss had sent with company policy changes. But instead of sending it to trusted peers, the email went to everyone at work.

Luckily for Damian, his boss never saw the email; a co-worker who knew their supervisor’s computer password helped him break into their boss’ office and delete the message.

You probably don’t have that option.

Looking back on the experience two decades later, he has some simple words of advice for his younger self: “Sometimes, self-editing means not saying or writing anything, especially if it’s a gut response based on emotions (and ego).”

While it’s best not to vent to co-workers for a variety of reasons, at least do it when you’re not in your cubicle.

Another pro-tip? If you’re using Gmail, you can enable the “Undo Send” feature, which could save you from more than a few sticky situations.

3. Keep Work and Play Separate

Jessica, a professor, was looking to leave her job and had befriended the assistant to her boss, the department chair, in the office. The assistant had access to the department chair’s email and one day forwarded a job listing from the address to Lauren, to which she replied “thanks xox,” not realizing it was sent to her boss—who could now see that she was searching for another job.

“’Forward’ is forewarned,” Jessica explains. “Always check the return e-address before sending a reply: If the email was forwarded to you, it may not be going where you think.” On top of that, make sure that if you’re doing something that isn’t work-related, keep it off of your work accounts at the very least, even if it’s more effort to do so.

Jamie, an account executive, once got called into her boss’ office a week into her first job after she accidentally forwarded some online shopping emails during her work hours she thought were going to a friend who had the same name as her supervisor.

“Luckily, I was young and my boss was nice, but she made it clear that I needed to be doing my work at work,” she says. “It was a dumb and totally avoidable situation that made me look immature, not to mention email-illiterate.”

When it comes to email etiquette at work, all five professionals agree: The best thing you can do is take as much of your life offline as possible.