‘Suddenly no WFH… [So] I put in a request for all 23 of my unused PTO days:' Employees share times they used their PTO to teach management a lesson

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Elna McHilderson • Managing Editor
May 12, 2025 9:00 AM EDT

It's almost summertime here in the U.S., and that means we're getting closer to vacation season. We all want to soak up the sun and warmth as much as possible. Whether you prefer to feel the sand between your toes or soak up the fresh air at the peak of a mountain top, you need to get out of the office and into nature. Vacation is a time for employees to remember why they work in the first place. We work to live, not live to work! If you don't take a vacation, you can easily get burned out. That whole antiquated mentality of not using your vacation days to make your way up in the company is completely BS, and we've all evolved to realize that. 

 

So, your company gives you paid time off (PTO) days to enjoy so you can gather your strength and not hate them. However, some management seems to still get upset when you use your PTO. As if they thought you wouldn't?? Here are several instances of employees initially getting their vacation days messed up by their boss, but turning it around and making it a problem for their boss rather than losing their PTO. 

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  • And this is a warning to companies: Don't mess with your employees when they're on their PTO days. You'll either get in trouble with HR or you will lose that employee. 

  • Cheezburger Image 10503650560
    via Unsplash+ (and Getty Images)

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

  • "HR said “we can’t make exceptions” so I took all my PTO at once"

    New manager comes in loud, talking about "structure" and "consistency". Suddenly no WFH, no flex hours, no swapping PTO. I asked to move two days. My cousin's wedding, she just goes,
    via StardustFrost
  • "Sorry, we can't make exceptions to anyone. It wouldn't be fair"
    via StardustFrost
  • Alright then, I put in a request for all 23 of my unused PTO days. Straight through end of quarter. No overlap, no coverage. It got approved in like...10 minutes? Lol okay. Couple days later she's in full panic mode:
    via StardustFrost
  • "Wait who's handling your workload?" "Dunno. I assumed you had a plan. No exceptions right?" She had to cover me and deal with fallout. Stuff piled up, clients got pissy, two people quit. I came back to a new HR memo:
    via StardustFrost
  • "Managers can now approve flexible PTO on a case by case basis." Turns out fair looks different when you're the one getting screwed.
    via StardustFrost

  • "He said no exceptions, use it or lose it (thinking I would opt to lose it)"

    I used to work for a major international bank where vacation was set to expire after 22 months. This meant that any vacation earned in 2025 would expire at the end of October 2026.
    via DataDude00
  • The issue with this? October is fiscal year and and usually an all hands on deck situation where a ton of critical reports need to go out to meet regulatory compliance.
    via DataDude00
  • Anyway my middle manager job was usually insanely busy so I rarely took my vacation and it was always a struggle to get my allotment in during the time before it expired. One year I had three weeks left and it was early October so I approached my boss and
    via DataDude00
  • asked if I could book the days now and show up to work for October and then just take the actual days off in November when it was calmer. He said no exceptions, use it or lose it (thinking I would opt to lose it)
    via DataDude00
  • I immediately went to the HR system and booked my three weeks vacation for the last three weeks of October and it gets approved
    via DataDude00
  • On the second day of my vacation he started e- mailing me with things like "we need this report run and verified by END OF DAY" even though I had my out of office set.
    via DataDude00
  • I'm not a j about it so I took it as a one off and just ran it and checked it over as it took me about an hour to do, no harm. Then he did that the next morning, and evening and the one after that and after that.
    via DataDude00
  • I e-mailed him back and copied HR asking if this meant my vacation days would get refunded, or if the company was paying out OT hours for this work since I was on approved leave.
    via DataDude00
  • I didn't hear anything for about 48 hours and then got a sheepish "enjoy the rest of your vacation we have this handled" response.
    via DataDude00
  • Apparently HR tore an absolute strip out of him for harassing and demanding work from an employee on vacation When I got back he said moving forward he would be amenable to some vacation day swaps to make sure we have appropriate coverage at the right times of the year
    via DataDude00
  • [edit] I should add HR were kind of sol don't think they cared all that much he was asking me to work on my time off, I think they sh their pants that he was demanding it in writing with a long history/audit trail.
    via DataDude00

  • "There wasn't a [dang] thing they could do."

    My father worked for the county school system for years. He was the type of man who never stayed out from work sick. He'd take a week or two off here and there or a day for family stuff. Anyway, he accrued A LOT of time. One day "they" came in and made a change, all accrued time had to be taken by the end of the year. Use it or lose it. They won't even pay it out anymore. He literally took off work from August to January and thing they could do. there wasn't a
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  • Cheezburger Image 10503668992
    via Unsplash+ (and Curated Lifestyle)

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

  • "... leaving her small office severely understaffed."

    When my wife and I were getting married, she had invited one of her coworkers. They both put in PTO requests. Her boss said that they could only approve her coworkers request because they need coverage and she had more seniority even though both requests were for our wedding, meaning if my wife couldn't get the time off, her coworker wouldn't be going obviously The coworker removed her request, called out sick and then They both ended up going to a different company leaving her small office seve
    via whatsit50

  • "I tried giving you 6 months notice and you didn't want it, so now you get nothing."

    I've mentioned this story a few times in other comments in this sub, but... My friend worked in the photo processing department in a chain retail store and was the only one there trained for that department. She put in for 2 weeks off for her wedding and honeymoon with almost 6 months notice and the manager denied it because "we need someone in that department, we can't have it unstaffed for 2 whole weeks."
    via RabidRathian
  • She had asked him repeatedly over the years to train (or let her train) someone else so she'd have more support and a replacement if needed and he always responded "Why, you're not going anywhere." One day the manager came in to find a huge queue of people at the photo section and no staff. He called her in a panic and demanded to know where she was and she said "I'm getting ready for my wedding and then going on my honeymoon, and after that I won't be returning to [store]."
    via RabidRathian
  • Manager flipped his lid and tried to pull the "You can't resign without giving at least 2 weeks notice!" BS but my friend just said "I tried giving you 6 months notice and you didn't want it, so now you get nothing." The photo processing department was unstaffed for about a month because they had to train someone at another store and then send them over.
    via RabidRathian

  • "...he called in sick, took his vacation anyway, and then resigned when he returned."

    I knew a guy who put in a request for vacation and it got approved, so he bought plane tickets, reserved hotel rooms, etc for his vacation. Well, 1-2 weeks before the vacation was to start, his boss told him that his PTO was canceled due to a "client engagement." He explained that the request was approved and he spent money on a bunch of non- refundable items, but the boss wouldn't budge and told him the expectation was for him to be working with the client during that time.
    via IndyColtsFan2020
  • So the time rolled around and he called in sick, took his vacation anyway, and then resigned when he returned. So instead of delaying the client a week or two in the first place, they had to scramble to find something to take the engagement and it was delayed anyway. Management can be really dumb and short-sighted.
    via IndyColtsFan2020

  • "Evil grin... I got my two weeks."

    My employer tried to tell me I couldn't take a two week vacation because they couldn't do without me for that long. Evil grin. My response was, "we did without you for two weeks while you went to Europe for the Olympics. Are you saying I'm more vital to the company than you are?" I got my two weeks.
    via HatingOnNames

  • " I had nearly 2,500 PTO hours saved up."

    I can top this. The year was 2012. I had worked the same job since 2001 and rarely used PTO. It was a very favorable PTO earning structure (progressive San Francisco where men had paternity pay a decade before other places). I wrote my own schedule and would usually schedule it so I worked Sun Mon Tuesday Wed Thursday Friday Sun Monday Tuesday then take 7 or eight days in a row off then was he rinse repeat. So I was able to take mini vacations frequently to not get burned out. After more than a
    via No_Spring_4539
  • had a family emergency and needed to take unexpected time off to take care of my grandmother who had a heart attack. HR and my boss told me no, it wasn't allowed because it's not bereavement and I didn't put in far enough in advance. Well, our policy was all PTO is paid when employment ends. I quit on the spot and they had to pay me a years salary on the next paycheck.
    via No_Spring_4539

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