December 23, 2018

When I first posted this in 2018, I know quite a few people shared stories of typos or reply-alls that shouldn’t have been. I also know that in six short years, we’ve come a very long way in how we compose our messages to one another, and what we say. But it seems everyone has a “whoops”.

Sunday, December 23, 2018

Once Upon a time, and I have to be very careful about how I tell this, I sent a group of people the worst e-mail of my life.

Very few people know about this (well, I guess until now), and those who do are the people I can trust to laugh it off and move on with life.

I’m sure there are some who, if they knew–even though it happened many, many years ago–their heads would explode.

What I do know is that I am not the only person to ever do this–to send an e-mail I wish had not gone out; whether, as in my case, it involved wording –or more specifically, spelling, or in others, that dreaded “reply all” box was ticked.

But it happened and I’m still here, and although I’d like to say that it hasn’t happened since… well… that wouldn’t exactly be true.

It happened more than a decade ago. I was working on a team preparing for a large high-profile event (I used to do that a lot , and can still pull it off if I must); part of my job was to coordinate a video celebrating a significant achievement.

And we were shooting high. I was asked to reach out to maybe six or eight people all told, political leaders (people in the White House and the Canadian Parliament); business leaders and incredibly intelligent academics… that sort of person–you get the idea–these were well-placed individuals.

I crafted a very carefully worded invitation with a request to be part of our program. Took me hours to write and edit, but in the end it was excellent—good enough to the extent that all, save for the one in the White House (not who you are thinking) eventually agreed to participate.

It’s probably a good thing these high-profile types have people managing their mail.

Here’s what happened. The message was so good (if I do say so myself) and I had crafted it in a way that all I had to do was swap out the name in the salutation and once again at the end of the letter. Hit forward and remove the “FW” and move on to the next. Probably saved myself a good five to ten minutes doing that.

It wasn’t until I got home and was barbecuing dinner (funny how we remember certain things; I was grilling vegetables–asparagus I think) when I decided to look at my phone, I suppose to see if anyone had replied to my message from earlier in the afternoon.

And that’s when I saw it.

In the subject line, I had left out a single letter.

It was an L.

And so the word PUBLIC… wasn’t the word public anymore.

Oh. My. God.

World leaders, business tycoons, really smart people–it went to all of them, because I had done it in the first message.

What did I do, after I picked my gut up off the floor?

I raced to my office, sent a follow up e-mail with the subject line to the effect of “UPDATE: ” and added the L to the subject line… and gave some vague preamble about errors in the previous version of the e-mail before reposting the otherwise perfect message.

Well, none of the big people ever saw it, and only one EA caught it and we had a good laugh. I spent the next month waiting for someone to freak out, but it never came. Oh? And the end result was fantastic.

Dodged the bullet for sure.

Now as I say, I’d like to say I never did it again, but I can be a little sloppy with these things… And just last summer I wrote a note about something making a public debut. I think it was a penguin. Yes, again, without the L. Only one sharp-eyed editor caught it, and again we had a little chuckle amongst ourselves.

If she only knew.

Now this wasn’t one that spell check would have found, because both are words. I think computers need to build in a sensibility check as in, “does this even make sense?” as well.

For now, I’ve simply decided I will never use either word in an e-mail again. Or at the very least, I will type very carefully. And anytime the word comes up, that’s what comes into my mind. Believe me, you hear one of those words a lot in every day conversation.

How about you? What’s the worst e-mail you’ve ever sent?

I know I’m not the only one. Go ahead, lay yourself bare and share your worst!