Why You May Not Want To April Fools' Your Boss

by Alexandra Antonopoulos

So, you've got a great April Fools' Day office prank that you're sure every single one of your coworkers is in on, and it's almost time to set up the final details, but you're wondering... should you play an April Fools' Day prank on your boss? Is Dan going to end your career for this? Is this really how you go out? In a shameful blaze of Post-It notes and mayonnaise-filled crullers? How do you explain this to your family? How do you justify this to yourself? All of a sudden, you're not so sure the balloon cubicle is such an innocent trick.

This is the time you need to stop, consider your options, and weigh the good against the bad. How well do you know your boss? Are you overthinking this? Should you really play an April Fools' Day trick on the person in charge of your livelihood? All fair questions, which is why I suggest you take a few extra moments before removing all of the toilet paper from the executive bathroom to contemplate the following.

Please, in the name of your 401k, check out these six reasons that it might not be a great idea to prank your boss this April Fools' Day, then make your decision accordingly.

1. They pay your bills

Yes, you think you pay your bills, but really it's your employer who takes care of the rent, the electric, the kids' piano lessons, etc. Sorry to say, but we're just the middlemen in the game of life. I once heard it said it would be more convenient to give HR your bank login info so they can just directly deposit your paycheck into other accounts. Do you really want to risk getting fired over a silly trick? I know, I know, it's a really funny trick, but still. Just keep this is mind.

2. You risk alienating your coworkers

Maybe you and the boss are actually really, really cool with each other and it's not the prank that would put your job in jeopardy, but it would just be obnoxious to your co-workers that you're able to get away with murder when they aren't. Again, just raising some possible issues, this is definitely a specific problem that most people wouldn't have. However, if this is the case, I still say go for it.

3. You might cause them physical injury

This opens up a Pandora's box of legal implications. What if you give them a wrapping paper desk and they break their wrist when they tumble to the ground? Sure you'll be cracking up, but are you really going to be laughing when you have to file all kinds of internal paperwork and meet with HR for the rest of the day? No. Very much no.

4. You've begun an unstoppable chain of pranks

If your boss is a one-upper, you're going to have to live in constant fear of getting pranked back. It will probably happen when you least expect it and, in predictable one-upper fashion, it will probably be unspeakably worse than the one you got them with. They are in charge of you, after all, and they won't want your prank to be funnier than theirs. Watch your back, friend.

5. You might not be that funny

Ever thought about how awful it would be should your "perfect" prank not go as planned, or if your boss doesn't get it, or if they get it and they have to look you in the eye and tell you it just wasn't that good? How do you live with that kind of rejection? How? Maybe, for some people, it's not a big deal, but if you're the type of person who plotted out a series of very particular circumstances just for a single punchline to land and it does not land well, then I'm willing to bet you'll be somewhat crushed by it. Keep this in mind, because I will not be there to revive your broken spirit if that happens, and I'd hate to think of you going through the emotional ringer alone.

6. You didn't think it all through

This is the person who signs your checks, who expects you to be at the top of your game as soon as you waltz into the office every Monday through Friday. If you didn't think of all of the ways this could adversely affect your boss — or anyone else in the office, for that matter — and something bad does happen, your boss is going to hold that against you. Not just today, not just tomorrow, but in that annual performance review in six months, and the one that happens 12 months after that... if you're still around that long.

It's very possible that your AFD prank will go off without a hitch, and that you and your boss will fall all over each other laughing once it's done, but it's important to consider the alternatives. I say, if you can go into this goofy national holiday with a clear conscience, knowing that you planned for the worst but expected the best, then you're the April Fools' Day winner, no matter what your higher-ups say. Worry about Monday on Monday. For now, it's all about those chuckles.

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