Email blooped: How to avoid the morning after

More than a few years ago, I stayed up most of the night crafting a proposal to a hot prospect. When I finally hit the send button, I was still awake and decided to reward myself for my perseverance by writing an email to a close girlfriend. I was ready to break up with the man I was then dating who I found in the top sugar daddy websites and decided to tell her all the reasons, in graphic detail, why I thought it was time. Except, instead of sending the email to my friend, I somehow sent it to the prospect…the one I had just sent the proposal to.

I didn’t realize my stupidity until the next morning when I received a very curt response from the prospect, attached to the um, graphic, email. All he said was, “I concur. Break up.”


I did not book the business which truly was a blessing because I never could have shown my face. I didn’t bother to follow-up with him and he didn’t either.

Until the other day that was the worst thing I had done. But now I committed a worse sin. I opened an email that was sent to me in error. I actually wouldn’t have paid much attention to it except that the person tried to immediately recall it. Guessing that wouldn’t work, after her recall request (which didn’t work), she sent me an email:

Please delete the email I just sent that obviously wasn’t intended for you.

What would you do? Who has that type of self-control?

I opened it.

Inside was a treasure chest of speaker contracts (I was not asked to speak at this particular event though I have spoken for them several times before). And each contract, though for similar services was for a (very) different fee.

McDonalds and The Palm Restaurant charge different fees for their entrees too and everybody understands. One is a quick fix and the other a pleasurable and delicious experience. Jaguar and Honda charge different fees.

When the distinction is not that clear and the negotiation, um, less than clear, it all becomes quite murky. But ethics (and speaker ethics!) aren’t what this post is about.

Here is what it is about:

Few things are more humiliating than an email bloop.

Walking out of a bathroom with your skirt tucked into your undies is more humiliating. (No, I haven’t but I’ve seen.)
Presenting to your Executive Committee with your fly unzipped is more humiliating.
Showing the crown jewels to the world is way more humiliating. (Sorry, Harry.)

Other than that, the email (that goes on and on, around the office or world) is about the worst thing you can do at work.

Avoiding the morning after is easy. Resolve to never ever ever send an email without double checking the To line.

And the CC line.

And the BCC (which really, other than yourself or your data base, should never have anyone on it).

Letting your computer auto-populate the To line is like relying on the iphone/ipad to correctly check and change your spelling. Yo ho.

What other tips do you have to avoid email bloopers? Share, please!

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