Boss demands a “good reason” for every vacation request, so an employee maliciously complies, inventing dramatic tales: ‘My boss still gets visibility uncomfortable whenever I come to ask for time off, it's kind of hilarious to me’

Author image for Etai Eshet
Etai Eshet • Editor
Jul 3, 2025 1:00 PM EDT

Some bosses just can't resist the urge to micromanage, even when it comes to your legally earned vacation days. In this office circus, the manager insists that every request for time off be justified with a "good reason" as if paid time off is a rare privilege and not, you know, part of your compensation. Instead of rolling over, our hero decides to turn the tables and serve up the most dramatic, Oscar-worthy trauma dumps HR has ever seen. 

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  • You want me to provide a good reason for why I want to use my vacation days? Time to trauma dump

    "Dude, why do I need to give you a good reason to take my vacation days? They're mine"
    via rilueda

    The image does not depict the actual subjects of the story. Subjects are models.

  • When the boss demands a reason, he gets a performance: tales of family illness, existential risks, and the emotional toll of life’s hardships, all delivered with the seriousness of a Shakespearean tragedy. The truth? Dad’s been illnes-free for years, but that doesn’t stop the employee from wringing every ounce of discomfort out of the situation. Grandma passed on so many times she’s basically a recurring character in these stories, and each time the boss is forced to sit through another round of awkward, soul-baring monologues.

  • So I work in a pretty low stress job, which makes it absolutely hilarious that my boss demands that whenever we take our paid time off we "give a good reason"
    via UnfoundedConfidence9
  • Like, dude, why do I need to give you a good reason to take my vacation days? They're mine, I'm entitled to take them to dedicate
    via UnfoundedConfidence9
  • Cheezburger Image 10523809792
    via Pressmaster

    The image does not depict the actual subjects of the story. Subjects are models.

  • the time to my new hobby of staring at the ceiling, it ain't none of your business.
    via UnfoundedConfidence9
  • Well I had planned to take a few days off to recharge after a (very relatively) intense work week.
    via UnfoundedConfidence9
  • Unfortunately the boss thought this was a great time to send out a "reminder" email that if we intend to take time off we need
    via UnfoundedConfidence9

  • No policy change comes from this, of course. The boss keeps demanding reasons, and the employee keeps delivering increasingly creative sob stories. The only thing that changes is the boss’s growing fear every time a vacation request is made in person.

  • to provide a reason & have it approved. This was a mistake on his part.
    via UnfoundedConfidence9
  • Cheezburger Image 10523813632
    via adipurnatama

    The image does not depict the actual subjects of the story. Subjects are models.

  • I went into his office, head hanging low, and started talking about my dad's cancer, how intensive chemotherapy was, I
    via UnfoundedConfidence9
  • didn't make myself cry but I was putting that theatre class I took in college to good use, I might have
    via UnfoundedConfidence9
  • even hit him with "and I'm just so used to seeing my dad as this strong, invulnerable guy, but... he's just human, y'know? And
    via UnfoundedConfidence9
  • soon he might be gone... how do you even deal with something like that..."
    via UnfoundedConfidence9
  • Now by this point my dad had been cancer-free for years, so this was purely performative, but my boss just looked so
    via UnfoundedConfidence9
  • uncomfortable, it was great. I wish I could say this caused the boss to send out an email saying we no longer needed to give a
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  • reason for our time off, but no such luck, instead I just kept coming up with other traumatic life experiences to justify my
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  • vacations. I think my grandma d d 3 times these past few years, poor woman. I may have to come up with something new for when
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  • she actually does di . My boss still gets visibility uncomfortable whenever I come to ask for time off in person instead of via email, it's kind of hilarious to me.
    via UnfoundedConfidence9

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management boss workplace-stories hr manager bosses work PTO managers supervisor workplace Horrible Bosses work-life balance
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