Email you wish you hadn’t sent?

For me, it usually takes 5 seconds after I’ve pressed the “send” button before the realization hits me. At first, I get this woozy feeling in my stomach that transforms itself to a squeamish trip up my spine, finally settling in the form of a pounding in my temples. Why did I just send that email?

The book I reviewed last week, Send: The Essential Guide to Email for Office and Home will tell you to never send an angry email and if I followed that advice I would eliminate most emails I wished I’d never sent, such as my worst one ever.

I was living in Colorado Springs at the time and you can’t get a direct flight there from anywhere, but instead have to transfer from Denver. Often, it is worth your time to rent a car and make the hour drive than it is to wait out your connection and on one such trip, I was returning from HP World and was all worked up over what I perceived to be the inefficiencies of our current organization structure.

During that drive, I talked myself into thinking it was a good idea to send an unsolicited email to my boss’ boss’ boss, telling him how we should REALLY be doing things. I mean, I was around 28 years old at the time so naturally I knew what was best. I not only sent the angry email, the know it all email, but also the late night tirade to someone 3 levels of management above you email. What an idiot.

Since I got in so late I slept in but by the time I checked email at 10:00 am the next morning, I had over a dozen damage control emails copying me from a wide variety of mentors and managers. It was almost the “kill my career” email as it made everybody between me and its recipient look bad.

I recovered, but it took me awhile to rebuild those bridges I burned through my late night stupidity. It remains the standard against which I measure all bad emails I’ve sent since.

How about you?

What is the worst email you wish you’d never sent?

Use the comments below to share your story!

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