Boss denies employee's vacation when they don't get it in writing, employee gets back at boss: 'I fail to understand how that is my problem'

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Jul 20, 2025 11:00 AM EDT

Bosses who put employees under scrutiny during hard times in their lives are just the worst. 

If an employee tells you they need to leave for a few days or a week to see family or handle a family emergency, the boss could send their condolences and set to work figuring out how to handle the workload. They may need to pull other employees in to brainstorm how to get everything done in a timely manner, or maybe they'll need to reach out to their own boss to explain why they can't meet a certain deadline. But the one thing they should absolutely not do is bother the employee about it! That person has stated that they need time away from work, so why do so many bosses take that as a sign to start throwing tons of work-related questions their way? It's almost like they take it personally when an employee needs some time for themself. Grow up, managers!  

Next up, read about the customer who got insulted by a grocery worker's nickname for him, and "spent the rest of the week trying to get her fired for it." 

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  • 01

    "Boss didn't want to approve a short leave. So instead I availed a long one."

    I'm sorry this became too long. I work with a large organization having multiple branches in every state across the country. I am the head of one such branch. My boss, the Regional Manager, controls around 15 such branches in a region cluster.
    via u/iam_saikat
  • 02
    During August this year, I had asked my boss for a 5-day leave for September, which he had promptly granted. I then informed HR about it, suggesting him to temporarily arrange for somebody to run my branch for the week (this was required because: 1. Due to some corporate directives, some of the branches including mine could not run without a branch head being physically present in the office. 2. Enabling someone from
    via u/iam_saikat
  • 03
    inside the branch to substitute for me wasn't possible due to technicalities). HR assured me there was plenty of time to arrange for my temporary substitute. So I didn't think much about it, since anyway it was his job to take care of in cases of leaves. My dumb ass didn't imagine it would be crucial to get the leave approved formally / in writing, because before this nobody had ever faced something like what I was
    via u/iam_saikat
  • 04
    about to experience. Come the last working day before I go on my leave, I asked our HR about who would take care of my branch in my absence. He flatly stated that there was no one available in the region cluster who he could depute to my branch in my stead, as "... many employees in our region are on leave because of festivities this week."
    via u/iam_saikat
  • 05
    Me: You are telling me this now? Anyway, I fail to understand how that is my problem, given that my leave was already granted a month ago. HR: Have a discussion with the RM (my boss). I called him up. Apparently the HR had already had a talk with him regarding this matter before I even called him.
    via u/iam_saikat
  • 06
    RM: How could you intend to go on a leave during this time when we are already under so much pressure due to this sudden staff shortage? On top of that our company's audit is due next month. Me: But you had ALREADY APPROVED my leave one month ago. RM: No, I'm sure I must have said that I would think about it.
    via u/iam_saikat
  • 07
    Me: Absolutely not. I wouldn't have booked my tickets and planned my travel to my hometown to see my parents, if you hadn't confirmed the leave. This went to and fro for a while and I was exasperated from this argument. By the end, I felt really humiliated that I had to almost beg for a leave.
    via u/iam_saikat
  • 08
    Me: Fine, I won't go. (At that point I arguably felt my dignity was more important than a few days off work). RM: Huh? Okay. (He was at a loss of words at my sudden giving up). So, my leave stood cancelled. My tickets had to be cancelled. Money wasted. And I was left utterly exhausted of this bulls
    via u/iam_saikat
  • 09
    A few days later, we got a notification for the yearly inter- state staff soccer tournament being arranged by Corporate. If selected, I'd be playing for my state. And the tournament - from selections till the final - would go on for a month. Soccer happens to be one of my favorite sports! So guess who just applied and got selected in the state team? Now, here's the funny thing about sports and activities that are arranged by our company's
    via u/iam_saikat
  • 10
    corporate center - the top management takes these seasonal events very seriously. If you are a participating employee, nothing or nobody on this planet could make you rather go back to sit on your chair and mind your job instead of participating. So as it appeared, although not on a leave per se, but I was all set to go on a month long tour across the country, playing soccer, without having to worry about managing a branch, and getting
    via u/iam_saikat
  • 11
    paid in the process. Even irrespective of my leave fiasco, this was a get involved in. good thing to [As some of you have expressed a curiosity - yes, extravagant events like these are not unheard of in big / Fortune 500 companies. My organization is a large conglomerate and the third largest employer in our country. Still it always beats my logic that they can spare some 150-200 employees for a month for "fun",
    via u/iam_saikat
  • 12
    yet there are some regions that are plagued with staff scarcity]. My boss's office was eventually informed about my participation in the event, and was advised to "... excuse the participant from his duties till the tournament was over". The day before leaving, I drove down to the RM's office to formally inform him, from my end, about me competing in the event and my ensuing month long absence that is to be expected.
    via u/iam_saikat
  • 13
    He looked expressionless, and just feebly asked me, "Why did you really participate?" Me: Well you see, had I happened to be at my hometown on a short leave this week, I wouldn't have been able to participate in the tournament at all, or even try for the selections. Sad, I couldn't go on that leave. The defeated look on his face was priceless.
    via u/iam_saikat
  • 14
    Cheezburger Image 10531765504
    via Getty Images For Unsplash+

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

  • 15
    Sweet bonus I forgot to add: one of the matches were hosted at my hometown!
    via u/iam_saikat
  • 16
    rilesmcjiles I had trouble getting leave. one time. I requested it in may for November. Some time around October the director had to approve all of our vacation requests, but wasn't actually denying or approving. I said "I'm going on vacation. I'll be back in two weeks. I hope I have a job to come back to".
    via u/rilesmcjiles
  • 17
    I worked there for another year until I found a better job.
    via u/rilesmcjiles
  • 18
    CoderJoe1 Expert level pettiness achieved! I bow to the master.
    via u/CoderJoe1
  • 19
    DaedruisRucker Great revenge, but you really should have just stuck to your guns and taken the leave, then immediately started looking for another job in case he tried to fire you when you came back. You bought plane tickets and made plans, no job is worth cancelling all that.
    via u/DaedruisRucker
  • 20
    Like you said, it's not your fault they tried to be scummy, and if they are as understaffed as they say, they can't afford to fire you so easily
    via u/DaedruisRucker
  • 21
    Thera
    via Omar Ramadan on Unsplash+

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

  • 22
    [deleted] Your telling me your job pays you to play soccer for a month all around the country against other companies in a tournament that is wild !
    via u/[deleted]
  • 23
    RJack151 I would have said that since you inconvenienced me, I returned the favor.
    via u/RJack151
  • 24
    nickis84 Love it! Boss couldn't handle 5 days without you and now has to cope with a month without you plus has to be a team player about it.
    via u/nickis84

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boss workplace-stories jobs job bosses work petty revenge petty soccer workplace trip bad bosses vacation
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