Boss Told Employee To Work On Vacation 'Unless You're In The Middle Of Nowhere,' So He Found The Pettiest Solution Possible

Hey, he was just following orders!

man planning petty solution after his boss made him work on vacation fizkes / Shutterstock

Most of us have had a job — or multiple jobs — where a vacation wasn't really a vacation.

One man on Reddit decided he wasn't suffering through a working vacation, and his response to the situation was an inspiration to anyone who ever found themselves having to answer emails poolside or log into supposedly "essential" meetings from the beach.

When his boss made him work on vacation, an ingenious employee came up with the perfect petty solution.

There is virtually no job that is so important it can't wait for a week or two of vacation. Unfortunately, demands like this from bosses seem to be extremely common.


And often, these bosses offer the absurd justification that when you work on salary and are getting paid regardless, you somehow owe it to them to be available. 

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That's one of the several irrational rationalizations this Redditor's boss used, too. But what ultimately got the boss in trouble, and the employee the work-free vacation he was entitled to, was the ultimatum his boss foolishly issued. 

His boss insisted that he had to be available to work on vacation unless he was 'in the middle of nowhere.'

The man worked in IT for a small, growing business, and given its size he was essentially a one-man band for all its technical needs. After two years of working without taking a break, his wife finally convinced him to take a one-week getaway.

He cleared it with one of the company's VPs, who said the vacation was fine so long as he trained his boss on some essential duties. And that was the moment things unraveled.

"In the midst of learning it dawns on him to ask why he has to learn this stuff anyway [since] I’m the nerd and it’s my job to do this," he wrote. When he reminded his boss of his vacation, things quickly went sideways. 


"You’re salary so you have to work during your vacation. You’ll bring your laptop and work phone with you." That's obviously not how things work, including for the boss himself.

The disgruntled employee pointed out that whenever his boss goes on vacation he's totally unreachable. "That’s because I go to places without service … Unless you're in the middle of nowhere, you have to work, you're salary" the boss replied.

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So the man booked a cabin for his vacation two hours from any town and without cell service. 

"Just to be clear; if I go to a place without service I won’t be expected to work, yeah?" he asked his boss, who responded that that was correct, "but you’re a nerd you don’t do anything outdoorsy." Oh, how wrong he was. 

"Wife and I rented a cabin in the woods, two hours from the nearest town and it doesn’t have service," he wrote. But that was only the beginning. He also "set up automatic email replies that have all IT questions and concerns forwarded to [his boss] since 'he’s the boss, he knows.'"



And to twist the knife one final time, he added, "[left my] work phone on the charger in my office with ringer on [and] door locked so he has to hear it." 


It all worked out better than he imagined. When he returned to work he found out his boss got so overwhelmed after refusing to learn any of his IT duties that he went on vacation himself to escape the disaster. Even the VP of the company found the situation hilarious. 

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Experts say that you should never, ever accept a demand to work on vacation.

This Redditor's story is five years old, but it's still circulating. That's a testament to how common, not to mention infuriating, workplace abuses like this are. And recruiter and TikToker @bentalkstalent explained how these workplace injustices are part of a bigger problem. 



In a video about the Reddit post, Ben strongly warned workers against ever complying with demands to work on vacation. "I've been in recruitment for 15 years," he said, "and I've talked to many, many candidates who think it's like this everywhere. It is not."


Ben recommended that if you do work for a company like this ... RUN. "If this is how your company is, you need to leave your company." He explained that it's employer disrespect and it will probably manifest in other ways beyond just vacation policies.



"Find a new company," Ben urged. "Life is way too short to deal with a company who will not let you escape their tyranny for a simple week vacation."

Good advice for workers, and combined with the Redditor's malicious compliance, an even more valuable lesson for employers.


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John Sundholm is a news and entertainment writer who covers pop culture, social justice, and human interest topics.