Boss refuses to let employee use vacation days from overtime all at once, employee complies and gives himself a 4-day work week for the rest of the year: 'My boss wasn't particularly happy'

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Ben Weiss • Writer and Editor
Sep 2, 2025 2:00 PM EDT

Some employers never consider the loopholes in their unnecessary policies. This employee was told to use the vacation days he had accrued from overtime, only he couldn't use the days all at once. He also couldn't take off on Fridays. So, the employee ended up finding a roundabout way to give himself a four-day work week for the rest of the entire year. 

Not only did this solution mean his boss couldn't argue with it, but the employee also used his new weekly day off (Wednesdays) as a means to get out of any work trips, as they usually fall on those days. You have to hand it to this guy for thinking outside the box and finding a way to comply with his boss's rules while also giving himself the best possible solution for his own work preferences. 

We hope that he shared his conspiratorial solution with other coworkers who had accrued extra vacation days. If this boss wants to micromanage and dictate how everyone uses their earned vacation time, then he deserves to be left scrambling for solutions when all his workers exploit the loophole at their disposal. Keep scrolling below for the full story and for the best reactions from members of this online community.

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  • 01

    "Not allowed to take vacation days from overtime all at once or on Fridays? Got you!"

    A man sits at a table using his laptop.
    via Unsplash+ (Brock Wegner)

    Image is representative only and does not depict the actual subjects of the story.

  • 02
    So a few years back when I was working for my previous company as a commissioning engineer (about 60% of the year of field service, 40% office), I had accrued about 10 days of not yet planned overtime by beginnig of october. We were allowed to use that overtime as vacation days,
    via desmosn
  • 03
    which made sense for me because I'd have pay a hefty amount of taxes on that money otherwise, and i didn't particularly need that money. So
    via desmosn
  • 04
    at some point my then boss calls me to his office to tell me I should plan when I'd take those days, with the requirement to not take them all at once and not on fridays for the rest of the year.
    via desmosn
  • 05
    Since I had already planned 3 weeks of vacation from vacation days during christmas, he probably had some things in mind. His intention about the "not everything at once"-part probably was to not have me missing for 5 weeks at once. The
    via desmosn
  • 06
    intention about the "not on fridays"-part probably was to not have me going home from any possible field trips every tuesday evening. So I sat at my desk and started thinking about if I should
    via desmosn
  • 07
    use those days in a way of 2 times a full week of vacation or some extended weekends beginnig after wednesdays.
    via desmosn
  • 08
    Looking through my calendar which wednesdays I would be best to use, I had a brilliant idea. Wednesdays. 10 weeks in a row.
    via desmosn
  • 09
    Adding to that 3 weeks during christmas. So starting the next week, I didn't go on any field trips for 3 months. Safe to say, my boss wasn't particularly happy, but did not say a word since his requirements were fully met.
    via desmosn
  • 10
    A man sits at a table talking on a cell phone in front of his laptop.
    via Unsplash+ (Brock Wegner)

    Image is representative only and does not depict the actual subjects of the story.

  • 11
    jam_manty 25m ago Whenever I hear someone say they don't take overtime because they will pay more taxes I always shake my head. Taxes will never take more than the extra you make. Getting paid for overtime will always mean more money in your pocket.
    via desmosn
  • 12
    Now, saying you want vacation over money is very real. Work life balance is a huge tradeoff that needs to be considered. Sorry, small rant.
    via desmosn
  • 13
    UnsureAndUnqu... . • 14m ago But why? The rule that you can take OT as vacation is good and your boss sounds reasonable, so why go for the option that'll annoy him most? Just to be as screwy with the rules as possible? Or was your boss a something? or
    via desmosn
  • 14
    Because that's exactly how "OT not usable for whole days" rule comes into place.
    via desmosn
  • 15
    ConsistentSched... • 5m ago My boss at my last job would've just denied it and added to his list of requirements.
    via desmosn

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workplace-stories employee work stories toxic-workplace job work Office Horrible Bosses overtime company toxic-work-environment
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