How One Engineer Turned a “No Fridays Off” Rule Into the Ultimate Midweek Vacation Power Move
Picture this: you’ve racked up ten days of overtime, and your company graciously lets you convert those hours into vacation days. You’re dreaming of extended holidays, maybe some extra-long weekends, or even a two-week escape from the grind. But just as you’re about to submit your request, your boss drops a bombshell: “You can’t take them all at once… and absolutely no Fridays.”
Cue the record scratch and the mental gears turning. What would you do? For one clever commissioning engineer, the answer was a masterclass in “malicious compliance”—following the rules to the letter, but not quite the spirit.
Let’s break down this genius-level workplace chess move, as shared by Redditor u/desmosn in the r/MaliciousCompliance subreddit.
The Overtime Quandary
Our protagonist spent much of the year traveling as a commissioning engineer, balancing field service and office work. By October, he had a stash of 10 overtime days burning a hole in his calendar. The company allowed overtime to be swapped for vacation—a sweet deal, since cashing those hours out would mean losing a chunk to taxes. With three weeks of Christmas vacation already on the books, the only hurdle between him and a glorious break was his boss’s two-pronged decree:
- No taking all overtime days at once.
- No overtime days on Fridays.
The logic? Management didn’t want him vanishing for five weeks straight, nor did they fancy him ducking out early from field trips by tacking vacation onto the end of the week.
The Plot Thickens: Midweek Mischief
Most people might have gone for a few Mondays here, a Thursday there, maybe a couple of three-day weekends. But our engineer saw the loophole—and sprinted through it.
What if, instead of clumping those days together or extending weekends, he took every Wednesday off for ten weeks straight? No field trips for three months. No five-day absences. And not a single Friday in sight.
It was, in a word, brilliant.
Suddenly, the workweek shrank to two days on, one glorious day off, then two more days on. The infamous “hump day” became a personal oasis—ten times over. And those three weeks at Christmas? Still locked and loaded.
Malicious Compliance Level: Expert
The boss, predictably, was less than thrilled. Imagine planning out field assignments, only to realize your go-to engineer is MIA every single Wednesday for three months. But there wasn’t a peep of protest—because the rules had been followed exactly as laid out.
This, dear readers, is the beauty of malicious compliance. It’s not about sabotage or insubordination. It’s about using the letter of the law (or, in this case, the employee handbook) to achieve maximum personal benefit—with a dash of poetic justice.
Why Does This Happen?
Stories like this resonate because they expose the unintended consequences of rigid, one-size-fits-all management rules. In an attempt to assert control, companies often create loopholes big enough to drive a vacation-laden dump truck through. Employees then leap through those loopholes—sometimes out of exasperation, sometimes out of sheer creativity.
It’s also a gentle reminder for managers: if you don’t trust your people to use their earned time off responsibly, don’t be surprised when they use your rules against you. Flexibility, communication, and trust go a lot further than blanket policies and arbitrary restrictions.
The Takeaway
Whether you’re a manager or an employee, there’s a lesson here. For managers: craft policies that make sense and respect the spirit (not just the letter) of fairness. For employees: sometimes, the best way to highlight a silly rule is to follow it exactly as written—and enjoy every minute of your midweek freedom.
Next time you’re faced with a “no Fridays!” edict, remember this legendary move. And if you’re a boss, maybe ask yourself: “Would I rather have someone out for ten weeks on Wednesdays… or just let them take a Friday off?”
What’s your best story of creative compliance? Share it in the comments below—because sometimes, the best way to stick it to the man is with a Wednesday off and a sly smile.
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Original Reddit Post: Not allowed to take vacation days from overtime all at once or on fridays? Got you!