Have you ever dreamt of telling your boss exactly what you thought them, but have never had the opportunity (or the kahunas)?
I’ve lived that dream. And it actually wasn’t that fun.
A long time ago I had a farewell lunch for a close colleague and friend of mine; it was a long and boozy Friday afternoon affair.
Later, back at the office, my friend was cleaning out his desk when the boss (who was part of the reason he was leaving) walked past and made a nasty joke to him in that way that only the boss can, where he laughs like he’s sharing a joke with you but he’s actually just made you out to be a dick.
Then the boss laughed really loudly to indicate that everyone else should laugh, like a villain and his cronies in a bad movie.
“Ha ha ha ha,” everyone said, not really meaning it.
My friend didn’t laugh and looked quite hurt. So I decided to cheer him up with a little in-joke between us – what’s the harm, right? I composed an email to him, the subject line read:
“Don’t worry mate, just say: at least I’m not a bald, one-eyed penis like you [boss’s name].”
I should point out at this point that the boss was bald and had also lost an eye in an accident – the penis bit was pure comedy.
I shot off the email feeling mighty pleased with myself and I motioned to my mate that he should read his email and we could giggle like school kids at our desks.
Not long after I got called into the boss’s office and he said he received a strange email from me that said:
“Don’t worry mate, just say: at least I’m not a bald, one-eyed penis like you…”
I don’t know how I didn’t wee myself. In fact I may have. Let’s say I did.
As it turns out, in my post-lunch haze, I had accidentally written my boss’s name in the ‘To’ field and sent it directly to him.
I fumbled through a story that someone must have hacked into my email account while we were at lunch, which he bought, somehow.
I walked back out to the floor with my head swimming like I was going to vomit, all the while thinking about the career suicide I’d just committed.
As I passed my mate’s desk he says to me: “I never got your email.”
Greg Kimball is a stand-up comedian and host and producer of Bunker Comedy. You can follow him on Twitter @GregKimball or on Facebook, Greg Kimball – standup comedian.