Boss revokes honeymoon PTO planned a year in advance and offers employee to quit when they refuse to cancel

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Etai Eshet • Editor
Jan 8, 2025 10:00 AM EST

Workplaces are built on the foundation of trust and mutual respect. At their best, they are communities where employees feel valued, supported, and understood. Bosses, (like my own guiding guru, Greg) in particular, play a vital role in this dynamic.

They are supposed to be mentors, advocates, and leaders, navigating their teams with fairness and empathy. Most of us want to believe in the good intentions of our employers and managers (I for one believe wholeheartedly. I'm a Greg believer).

After all, why would they make promises they cannot keep or fail to support those who go above and beyond to communicate and plan ahead? Surely, workplaces prioritize their people just as much as their profits (I know Greg does). We should really appreciate the brilliance of modern corporate culture 

Today's story is a masterclass in workplace irony, starring a boss so considerate and a company so forward-thinking that they turned a honeymoon into a cautionary tale about trust.

It began with an employee and his wife planning their dream honeymoon for a year. The employee, ever diligent, kept his supportive boss in the loop. The boss, fresh off his own month-long, interruption-free honeymoon, assured him repeatedly that time off wouldn't be an issue as the company offers unlimited PTO. Leadership goals, are you with me? Good. Then came the twist.

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  • 01
    "No boss who wants to retain staff would deny a honeymoon leave request with that much notice given"
    via pcess609

    This image is for illustration only, and the subjects are models; the image does not depict the actual subjects of the story.

  • A month before the trip, the boss revealed that the time-off request was denied, citing the company handbook’s genius clause: PTO can be rescinded at any time, for any reason. When the employee proposed compromises—unpaid leave, reduced hours, or even working less intensely during the trip—the company stood firm: full-time work on an international honeymoon was clearly the only option.

    When the employee chose to enjoy his hard-earned vacation anyway (how dare he!), the company responded with a generous ultimatum: resign voluntarily with two weeks’ exit payout or be labeled a job deserter. Truly inspiring leadership.

    The boss’s handling of this situation deserves special mention. Rather than advocating for his employee or owning up to months of false assurances, he quietly stepped aside, avoiding confrontation with unparalleled grace. A true innovator in passive management.

    The takeaway from this story is that not all bosses are created equally, and Greg stands tall above all of them. Apparently, Some workplaces excel at making you rethink your life choices. Take the exit payout, raise a glass to freedom, and savor the lesson: trust in bosses like this is best rewarded with sarcasm and a well-deserved break from their nonsense.

  • 02
    PTO for Honeymoon rescinded- how to navigate
    via WildLandscape1368
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    Long story short. My husband and I have been planning our honeymoon for just under a year.
    via WildLandscape1368
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    My husband had been in communication with his boss about our honeymoon throughout this past year and his boss never raised any concerns initially and had told him there should not be any issues to accommodate the time off, as he
    via WildLandscape1368
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    A year really does seem like too short a notice. I mean, how can a workplace function if every employee simply announces whenever they need some of their unlimited time off? Are we running a business here or what?!

    Cheezburger Image 10451420928
    via Tahir osman For Unsplash+

    This image is for illustration only, and the subjects are models; the image does not depict the actual subjects of the story.

  • 06
    had also taken a month long honeymoon the year prior. A few months ago, my husband had put an official request in, and it sat waiting for final approval as there was a shift in upper management- his boss still remained at the company. About
    via WildLandscape1368
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    a month before our honeymoon, the PTO was not approved by the new upper management. His boss let him know that they could not accommodate any of the time off and let him know that it would probably be best if he canceled the trip. We did not
    via WildLandscape1368
  • 08

    A deal is a deal, right?

    Cheezburger Image 10451439360
    via Tahir osman For Unsplash+

    This image is for illustration only, and the subjects are models; the image does not depict the actual subjects of the story.

  • 09
    want to do this, we had already booked our international flights, rental cars and accommodations and made plans to see family he hasn't seen in over 10 years.
    via WildLandscape1368
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    Yes, in hindsight, he should have gotten the approved time off from his boss in writing or pushed for a faster approval from upper management, but he had no reason to believe that the PTO
    via WildLandscape1368
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    wouldn't be approved based on his very close relationship with his boss, open and clear communication throughout the year and proactiveness to ensure everything was taken care of before we left. It surely has been a lesson learned the hard way.
    via WildLandscape1368
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    Anyways, my husband tried to compromise with the company, asking for a portion of his PTO to be approved, asking for non paid time off or if he did need to work during our honeymoon if he
    via WildLandscape1368
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    could shift his working hours so he wouldn't have to start at 3 am. None of these were approved and they requested that he work full time on our honeymoon.
    via WildLandscape1368
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    Well it's a few days into our honeymoon and they noticed he hasn't been working. They offered him the ability to resign and they'd give 2 weeks severance or if he doesn't get back to them they will assume that it is voluntarily resignation.
    via WildLandscape1368
  • 15
    Well this has just turned into long story long as this point hahaha What would you recommend? Thanks!
    via WildLandscape1368
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    EDIT: yes we work in the USA. My husband's company has unlimited time off, which just saves the company from paying out any accrued time if they leave. When his boss notified him
    via WildLandscape1368
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    that they couldn't approve the time off, he sent the employee handbook which outlines that the company can rescind PTO for anytime for any reason, so I don't really think if we had anything in writing it would help anyways.
    via WildLandscape1368
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    We are probably leaning towards him taking the severance and quitting, as it would be the easiest route out. It sounds like if he continues not to work, it would be classified as job abandonment (aka voluntary resignation) and he wouldn't qualify for unemployment.
    via WildLandscape1368
  • 19
    But_like_whytho They did this to him on purpose.
    via But_like_whytho
  • 20
    KidenStormsoarer you tell them IN WRITING that it is not a resignation, that you are taking the PTO that was approved by his boss prior to booking and paying for the trip, and is part of his compensation. if
    via KidenStormsoarer
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    they really want to push it, when you get back, you contact an employment lawyer and file against them for wrongful termination based on promissory estoppel. you acted in good
    via KidenStormsoarer
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    faith based on assurances given by somebody in a position of authority, and it was only after you made your arrangements, and well outside of a reasonable timeframe from when it was submitted, that they decided to act in bad faith.
    via KidenStormsoarer
  • 23
    MidlifeCrisis Too It's ultimately a moot point, if he doesn't resign he may be terminated for job abandonment due to an "unauthorized leave". The
    via MidlifeCrisis
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    employer is not required to terminate him, they could just write him up or suspend him, but he won't find that out until after he tries to return to work.
    via MidlifeCrisis
  • 25
    QWxx01 This must be an American company. Stuff like this is simply outlawed here where I live (the Netherlands). Request for PTO put in two weeks ago and no response? Approved by law. PTO denied but for a cr p reason? Still approved by law.
    via QWxx01
  • 26
    Mountain_Strategy342 I would sit back and enjoy my honeymoon, perhaps take a few minutes to SERIOUSLY evaluate whether I would want to work for this company, then wait for them to fire me.
    via Mountain_Strategy342
  • 27
    Objective_Problem_90 What good is unlimited time off if they don't let you use it? Your spouse should have been looking for new work unless he is prepared to work on your honeymoon.
    via Objective_Problem_90

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management christmas boss privacy workplace-stories hr manager private bosses work PTO managers supervisor workplace Horrible Bosses work-life balance bad bosses toxic-work-environment
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