Employee told he is going to lose all of his leave by the end of the year, takes it all at once, leaving projects struggling to be completed: 'Use all your PTO before December 31 or lose it? Alright, don't mind if I do, even if the project burns...'

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Brad Dickson • Managing Editor
Jun 14, 2025 6:00 PM EDT

It's amusing to think that PTO exists solely for the purpose of taking a break from work when needed, yet you just never seem to use it. Like it is specifically there to use, but the reality is that all it's really there for is so that you can watch the balance slowly climb forever. It really feels like you're always too busy to take some time off, but are we conditioned to feel this way, or is it some internal need we're fulfilling to ourselves? 

To make this even worse, as you're sitting there watching your leave balance climb, your employer will be getting increasingly antsy about it. See, depending on where you work and what arrangement you have, your employer may be on the hook for making sure that the balance of their employee's PTO is available to be paid out, which becomes a pretty big risk when you add it all up. So, at some point, you'll be told that your leave balance is expiring, or if there's a round of layoffs, you might even end up on the chopping block simply because the amount of money your leave balance represents to the business. Then that massive leave/PTO balance, which was yours to rightfully take, was all for naught. 

This worker was told they were going to lose all their leave at the end of the year, but that backfired for their employer when they took all of it during the busiest and most important time of the year, leaving important projects struggling to be finished before deadlines.

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  • 01

    "Use all your PTO before December 31 or lose it? Alright, don't mind if I do even if the project burns."

    This happened a couple of years ago at my old job. A pretty demanding corporate gig where we were always juggling tight deadlines, constant emails, and way too many meetings. that could've been Slack messages. Around early November, HR sent out one of those all-staff emails with a bright red banner and urgent tone. It read something like:
    via jessicasergey
  • 02
    Cheezburger Image 10517160704
    via Ezequiel Garrido

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

  • 03
    REMINDER: All unused PTO must be taken before December 31st. We will not be allowing rollovers this year. Please schedule your remaining days immediately or risk losing them.
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  • 04
    No exceptions. No flexibility. No consideration for project timelines. Now, I wasn't one to take a ton of time off during the year mostly because every time I tried, something urgent would come up and I'd get guilted into postponing. So by November, I had 10 full days of paid time off just sitting there. And according to HR's big red warning, I had about 6 weeks to use them.
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  • 05
    Naturally, I did what any burnt-out, underappreciated employee would do: I opened the calendar and booked myself off from December 18 to December 31. Two full weeks. Right before the New Year. Smack in the middle of the most chaotic time in our project cycle.
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  • 06
    A week later, my manager (let's call him Rob) came to me in a mild panic. Rob: Hey, I saw your PTO request. I was hoping we could shift that a little. December's going to be a critical time for [project name], and we really need all hands on deck. Me: Yeah, I get that, but HR sent that PTO deadline. If I dont use those days, I lose them. And I've already worked through enough vacations this year.
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  • 07
    He looked uncomfortable but couldn't argue with the logic. I even forwarded him the HR email with the subject line: Using My Days. As Required :). He escalated it to HR, of course. HR's reply? We understand it may be inconvenient, but our PTO policy is final. Managers are responsible for planning around employee availability.
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  • 08
    That reply felt like Christmas came early. So I prepped my team as best I could, left detailed notes, and on December 18, I logged out, stress-free. While they were scrambling to hit deadlines, dealing with last-minute client requests, and working late... I was sipping hot chocolate, watching Netflix, and actually enjoying my holiday season for once.
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  • 09
    When I came back in January, the project had been delivered barely. The team was exhausted, mistakes had been made, and the post-mortem meeting was basically 45 minutes of finger-pointing. But no one dared say a word to me. After all, I was just following HR's rules. Moral of the story? If a company insists you follow policy to the letter, don't feel bad when you do even if it means watching the ship. catch fire from your cozy vacation cabin.
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  • 10
    dlc741 Who came up with those idiotic deadlines? All of our projects assumed that at least half the staff would take off for holidays and planned for a slowdown from Thanksgiving through New Year's.
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  • 11
    Cerulean_IsFancyBlue You missed the real moral: take your PTO. The project will survive. Unless you're an officer or a stakeholder and expect a substantial reward for the effort, don't surrender your personal life for the job.
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  • 12
    TaxiCab88 Which country is this, because it's probably a whole entire month if they haven't taken any time off all year- I had 10 full days American. Literally no way it's not.
    via jessicasergey

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