How to Torture Your Boss While They Are On Vacation

Dear Boss,

Hey, I hope you’re having fun on vacation and this email reaches you on the sandy beaches of “Riviera wherever you are that I couldn’t afford.” Don’t worry about responding to this, just wanted to send you an email to say we’re having a minor issue. It’s not really that important and can certainly wait but I like to send emails to people when it’s hanging over my head so I don’t have to worry about it anymore. I know you like to do the same. Not that I want you to worry about it so don’t read this and worry about it. Just because it’s your company and the fate of our collective livelihood shouldn’t mean that you should read this. I mean, come on! Have fun! But just know that we’re having an issue back here that we can’t resolve. Just wanted to let you know :)!

Dear Employee,

I hate you.

Why Your Torture Plan Will Surely Backfire


Thinking your boss isn’t checking their messages while on vacation is as sound as your belief that you aren’t annoying your boss with your emails. Bosses can’t stop being the boss even if they want to. Your need to make sure your bases are covered or to cross something off of your to-do list without respect for someone else’s R&R only serves to piss off your boss (and really everyone else you do this to).

When our phone indicates we have a message waiting it sends a signal to one of the two most powerful parts of our brain: the reward center. That message says to the reward center, “Yay, you have a friend, someone likes you!” That message triggers the dopamine cycle, which releases dopamine, the feel good drug in the brain. Dopamine is also triggered when we eat a piece of chocolate cake, smoke a cigarette, drink alcohol or have sex. Not surprisingly, we are all dopamine addicts. Not obsessively checking your technology puts you through the same withdrawal, and requires the same amount of discipline as refraining from any pleasurable activity that triggers dopamine.

So what’s the outcome of these annoying emails that you can’t control yourself from sending? As humans, we like to hold onto annoyances over pleasantries, bad things over good things. Your boss will always remember you ruined their vacation, despite the million great things you do on a daily basis.

Maybe Try This Instead?


Fight the urge. Fight it hard. Unless it’s an emergency put that annoying email on hold and save it for when your boss returns from vacation. You will prove to your boss that you can hold down the fort, and there’s no better feeling for a boss than that. Your boss will return from vacation refreshed, and will like you more for not annoying them.