How to P*ss Your Boss off without Getting into Trouble

pissed off boss with glasses

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Bosses are the worst… they yell at you when you mess up, reprimand you when you’re late, and threaten you with your job when you call in sick (but end up checking in at a Creed concert). So now you want to get back at them, but at the same time you’re afraid you’ll get fired (and rightfully so; your job is holding on by a microns-thick thread). So, just how do you get back at them? Well, most importantly, you’ll have to get creative, and you’ll also have to avoid getting caught. Let me help you p*ss your boss off without getting into trouble. This is all hypothetical but if the company culture allows it, you might actually be able to pull a prank or two on the boss man.

First, I will reference Sun Tzu’s seminal strategic guide, The Art of War (paid link): “If you know your enemies and know yourself, you will not be imperiled in a hundred battles.” Let’s use this as a starting point.

Unreciprocated networking

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Your boss is a networking monster. He has special pockets tailored into his coat to hold business cards, promotional pens with his name on them, and cigars that have “He’s the Man!” and his number written on the label. The man knows how to shmooze, so what would be more maddening for someone like that than receiving emails with networking opportunities and not being able to return the favour or follow up?

Start out with a gift basket delivered to your boss with a fake name and a note reading: “Your perspectives seem very interesting and I would love to work together with you. I look forward to hearing from you, Bud Budderson.” This will create two types of anxiety for your boss: not being able to recall a Bud Budderson and the urgency of responding to someone that is eager to work with him. You know your boss is highly driven and chases every opportunity that presents itself to him. Allow a few weeks for the desperation to set in and then send a follow-up email:

Dear Boss Bossington,

Unfortunately, I haven’t heard back from you yet, and the money that I have to invest in the project you told me about is not tied up at the moment. I look forward to hearing from you. Bud Budderson.

Now set up an email for the fictional Bud Budderson and change the settings so that all your boss’ emails are rejected. He will continue trying to contact Bud but to no avail. For the coup de grâce, send him a final email asking him to contact Bud immediately on a disconnected cell phone number, and then sit back and enjoy an anxiety-induced fireworks show.

The ticking

nullThe Huffington Post

You know those greeting cards you can buy that play sounds when you open them? Well, you can now buy just the sound-making circuit (paid link) to make your own cards… or hilariously drive people insane.

Here’s what you’ll do: click on the link above and buy the circuit, get super excited when your package arrives (because, come on, the delivery guys is the closest thing to Santa Claus adults have), open your package, and record a series of clicking or ticking noises. Now, to be the most effective, you need your clicking or ticking noises to play continuously for a few seconds, stop for a few seconds, and then continue playing.

Make sure not to have a specific pattern, however, as it would only lead your boss to uncover the device. Then plant it inside his office in a place that is hard to access (you can throw it behind a heavy bookshelf, for example, or under a heavy, immovable potted plant).

Once your boss notices the clicking, he will try to find the source, but by the time he gets close, it will stop. At some point, the ticking or clicking will become so maddening that your boss will tear his own office up to find the source. Even if he does find it, though, there’s nothing that will tie you to the crime. Just sit back and enjoy the show as your boss rips his Italian leather couch open with a letter opener to find where the mysterious sound is coming from, then watch him pause as it stops, return to his desk, only to jump up the moment it starts again.

Why not double the fun by planting two devices?

Pet peeves

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Everyone has a specific set of things that really annoys them; personally, one of my biggest pet peeves is having bread and peanut butter, but no pickles. I don’t necessarily use those in unison, but it aggravates the hell out of me when the collective availability of those items doesn’t exist.

Now you could go for the safe option of choosing two of the most popular pet peeves which are interrupting someone and not shutting up, but since you really want to get under your boss’ skin, do your research to see what makes him flip his proverbial lid.

Although you could enact the pet peeve, because you can get fired for irritating someone, it might be a better idea to have a fall guy. Say your boss hates loud chewing; find a coworker that eats way too loudly and facilitate their interaction. For example, pitch a lunchtime meeting and have the noisy eater sit next to the boss. You will see your boss seething with frustration, but he won’t be able to say anything in front of everyone. Once you see his ears go bright red and his cheek muscles start flinching repeatedly, know that you have accomplished your mission.

The sociopath

nullBig Beyond Belief

This method is called the sociopath because, honestly, you have to be one to do it. Also, it can get you arrested, and it is the only item on this list that has that distinction. You will dose your boss’ coffee with anabolic steroids. The whole point of this article is to find out how you can p*ss your boss off without getting into trouble, right? Well, this is the way to do it if you really loathe him.

Anabolic steroids have numerous side effects, the most well-known being so-called roid rage. He may also experience shrinking testicles, breast growth (yes, as in man boobs), baldness, and acne. Again, this is not a technique that I would recommend; I’m just throwing it out there and letting you know that if you do it, you’ll probably go to jail.

Can you think of any other ways to p*ss your boss off without getting into trouble? Let me know in the comments section below!


This article was originally published in September 2015.