Entitled employee in her 60s "accidentally" retires: 'Pinnacle level pettiness'

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Jun 17, 2025 3:00 PM EDT

This employee thought she had the perfect way to always ensure she got her time off approved. Instead of talking to her boss, she'd just wait til her boss wasn't around, then sneak into the books and add in any time she wanted to take off. That's a pretty great workplace hack… but there's no way any boss would fall for that more than 2 or 3 times. Plus, that's a guaranteed way to make your boss give you a stern talking-to! After all, that undermines their trust, and why would they keep around an employee who acts like that?

Part of this employee's issue was that she thought she was irreplaceable in her position. That's just not true for any job, no matter how specific it is. There always will be a worker who comes after you, and the company will fill the role as quickly as they can. 

Next, read about another employee who had some pretty goofy workplace ideas, such as pretending to be his own twin every time he wanted to skip a meeting: "The only difference was that he wore glasses and a beanie."

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  • 01
    My friend (I'll call her Sandy) worked at a travel agency in British Columbia, Canada. It was a small, owner-operated business with the owner and three employees including my friend. Everyone worked Monday to Friday from 9:00 a.m. to 5:00 p.m.
    via u/technogrind
  • 02
    One of my friend's coworkers (I'll call her Jane), an older woman in her early to mid-sixties, was a long-time nuisance employee. Among other sketchy behaviour, Jane was always scamming ways to take time off over and above her official paid vacation time. In order to make up for the lost hours, she would claim overtime hours/pay by supposedly going in to the office in her off hours "to finish up" work without being requested by the owner to do so.
    via u/technogrind
  • 03
    Despite being caught in her own lies on a number of occasions and being warned about trying to claim for unsanctioned overtime, the owner of the travel agency was reluctant to officially reprimand Jane or get rid of her. The reason being is the owner discovered after she had hired Jane that Jane had actually been fired from her previous job at another local travel agency for pulling the same stunts; however, Jane had sued her former
    via u/technogrind
  • 04
    employer for unfair dismissal and had won a settlement. After a few years of my friend Sandy working at the travel agency, the owner was ready to retire and offered to sell the business to my friend. Sandy took her up on the deal and took over the business while keeping on Jane and the other employee. Once again, just as the previous owner was afraid to get rid of Jane, so was Sandy for fear of being sued.
    via u/technogrind
  • 05
    When Sandy took over the business, she instituted guidelines regarding taking time off and she established an official "no overtime" policy. Jane would still try with her shenanigans but was far less successful in getting what she wanted with my friend in charge. However, Jane still had one trick up her sleeve when she wanted to take time off on a whim. Sandy was a divorced single mom of two boys who were heavily involved in youth
    via u/technogrind
  • 06
    hockey. She would sometimes leave the office an hour or two before closing to get her boys to hockey practice or a game. In order to avoid requesting in person and potentially being denied, Jane would wait for Sandy to be out of the office to book a day off if she didn't feel like coming into work or had made plans. Sandy would then arrive at work the next morning only to discover that Jane wasn't coming in.
    via u/technogrind
  • 07
    Despite this happening a number of times, Sandy would usually let it slide since there was now a definite "no overtime" policy. Therefore, Jane could no longer claim to come in to work on the weekend or after hours in order to try and make up for the day off. She would either miss out on a day's pay, in turn saving Sandy money as the owner, or it would come out of her remaining paid vacation days. Moreover, two people in the office at one time could usually handle everything.
    via u/technogrind
  • 08
    Jane not coming in was really a no-loss situation for Sandy. There was one time, however, when Sandy was going to be away for one or two work days just before the weekend to take her boys to a hockey tournament. She told both Jane and the other employee both verbally and in writing that they could not book time off for the dates in question since she would be away and needed both of them in the
    via u/technogrind
  • 09
    office. Within a few days of giving this notice, Sandy went in to the office on a Saturday to do some paperwork and go through the sales for the week. This is when she discovered that, only the day before, Jane had booked a trip for her daughter and son-in-law to Las Vegas as well as a plane ticket in her name to Calgary where her daughter lived. Both the trip to Vegas and the ticket to Calgary coincided with the dates Sandy would be out of the office.
    via u/technogrind
  • 10
    Sandy then checked the vacation booking schedule to further discover that Jane had indeed booked the days off that she had expressly been told she couldn't have. Not mentioning she had discovered the travel Jane had booked for herself and her daughter, Sandy emailed Jane telling her she would have to deny her the days off since she had already been told they were
    via u/technogrind
  • 11
    unavailable because she (Sandy) would be away and needed Jane in the office. Through a continued series of email exchanges, Jane replied and outright lied to Sandy with some excuse about her daughter getting some long-awaited medical treatment or surgery, and she needed to go to Calgary to help out for a few days and look after her granddaughter. Sandy replied to this lie by telling Jane she knew about the trip she had booked to Vegas for her daughter
    via u/technogrind
  • 12
    and son-in-law; that Jane's trip to Calgary was most likely to babysit her granddaughter while her daughter was in Vegas; and that she would still have to deny Jane the days off especially since she booked them after being told they were unavailable. Jane countered in her subsequent reply, without even addressing the fact that she had been caught in a lie, that she had been a dedicated employee of
    via u/technogrind
  • 13
    the travel agency for several years and couldn't understand why she was being treated so unfairly after all she had done for the business. She then wrote that since she wasn't being treated as a valued employee, she had no choice but to retire and was giving her two-weeks' notice. Despite Jane's threat, Sandy replied that she would still be unable to grant her the days off and left it at that without making any mention of Jane's threat to quit/retire.
    via u/technogrind
  • 14
    Sandy then contacted her accountant, who also acted as her de facto business advisor, and explained what had happened with Jane. Also aware of Jane's previous shenanigans, Sandy's accountant told her that this was the out she had been looking for with Jane, and she had it all in writing. He told her that Jane had essentially resigned/retired and all Sandy needed to do was honour Jane's desire to do so, let her finish out her two weeks, or pay her two-
    via u/technogrind
  • 15
    Cheezburger Image 10517990400
    via Getty Images For Unsplash+

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

  • 16
    weeks' wages in lieu with no further severance pay legally required since she hadn't been fired. The following Monday, Sandy went into the office early accompanied by her longterm boyfriend to act as a witness. She put Jane's belongings from her desk into a box and took the things that were property of the business. Since Jane was old school and had resisted inputting client information in the
    via u/technogrind
  • 17
    computer database, this also included a small box filled with index cards which had client phone numbers, addresses, credit card information, and other personal information noted on them. In the meantime the other employee had arrived for work, and they all waited for Jane to show up. Jane arrived just before 9:00 acting as though nothing had happened and greeted everyone with a "good morning" as she
    via u/technogrind
  • 18
    walked through the door. However, she was apparently taken slightly aback when she noticed Sandy's boyfriend seated in the far corner of the office. At this point, Jane was mid-way to her desk when Sandy informed her that there was no need to go any further and that she had accepted Jane's notification of retirement. She then handed Jane a cheque compensating her for the hours she had worked in the current pay period as well as two-weeks' wages in lieu of Jane
    via u/technogrind
  • 19
    finishing out her final two weeks before her "retirement". Jane was dumbfounded and went into panic mode, "But I didn't retire! I'm not ready to retire!" Sandy responded that indeed she had retired, given her notice and had proof of it in writing. All Jane could do was continue repeating, "But I didn't retire! I'm not ready to retire!" while unsuccessfully attempting to get the support of the other employee who refused
    via u/technogrind
  • 20
    to come to her defence. Sandy then pointed to the box containing Jane's belongings, wished her a happy retirement, and told her to leave the office. Jane quickly rifled through the box and noticed that the small box containing the index cards with client informaiton was not there. She insisted that Sandy return it to her which Sandy refused to do explaining that it was property of the business, contained personal client information, and that she would
    via u/technogrind
  • 21
    be in violation of Canadian privacy laws if she were to let Jane take it. Jane's shock had now turned to obstinance and she refused to leave without the box. Both the other employee and Sandy's boyfriend had started to get involved, repeatedly telling Jane to just leave. Sandy then informed Jane that if she didn't leave, they would have to call the RCMP (Canadian
    via u/technogrind
  • 22
    police), at which point, Sandy's boyfriend dialled 911 to inform the dispatcher of a disgruntled former employee at XYZ Travel Agency who was refusing to leave the premises. Within a few minutes, two police officers arrived, and Jane immediately ran to the door ranting about being fired and about the missing box of client info. In order to deescalate the situation, one police officer told Jane to come outside and explain to him her
    via u/technogrind
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    side of the story. The other officer remained in the office to hear Sandy's side of the story agreeing that Jane was not legally entitled to the box of client info. The other officer then reentered the business and told Jane to wait outside. He said that Jane was insisting that Sandy was holding onto her personal belongings, namely a box of important information. Both Sandy and the officer who had spoken to her explained the
    via u/technogrind
  • 24
    contents of the box to the other officer who in turn agreed it was not Jane's property. The police officers then picked up the larger box of Jane's personal belongings, took it outside to Jane, and told her she needed to go home. To rub salt in Jane's wounds, the next day, Sandy put up a large sign in the window of the business congratulating Jane on her retirement and even put a small announcement in the local
    via u/technogrind
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    newspaper doing the same thing. The icing on the piece of revenge cake was Sandy, when filling out the necessary government forms for when an employee quits / gets fired / retires, made sure to check the box labelled "retired" for the reason for Jane no longer being employed. By doing so, Jane was ineligible to collect unemployment insurance benefits.
    via u/technogrind
  • 26
    Cheezburger Image 10517990656
    via Getty Images For Unsplash+

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

  • 27

    People loved this story, and were surprised that she lasted so long in the role considering her sneaky ways

    GovernorSan Sounds like Jane played herself. She clearly misunderstood the kind of working relationship she had with her employers. She must have thought she was indispensable, that the reason no one fired her despite her constantly violating time off policies was that they needed her too much. She thought she
    via u/GovernorSan
  • 28
    was making a dire threat to her employer when she threatened to retire, but instead that was exactly what they were hoping for. I just don't get how she could be so deluded.
    via u/GovernorSan
  • 29
    Briarschance21 The retirement announcement cracked me up! Pinnacle level pettiness. Love it.
    via u/Briarschance21

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terrible coworkers workplace-stories employee work stories job work coworkers working employees workplace retired retirement coworker quitting
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