43-year employee gets vacation time cut, takes 10 weeks of PTO and refuses to come back for less than 7 figures: 'It's the day Jimmy is supposed to return. He doesn't'

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Remy Millisky • Writer and Editor
Jun 3, 2025 3:00 PM EDT

If you value your employees, don't mess with their hard-earned vacation time! 

One of the nicest parts of working a salaried job instead of an hourly job is getting a nice 2 weeks off per year. You work hard on your projects, send your emails, meet with clients, and then comes the time you look forward to all year long: vacation time! For some people, that means taking long hikes to scenic venues, while for others, it means piling the family in the van and heading to an amusement park. Some folks save up for years to take cruises or travel to European countries. There's so much to see and do, and looking forward to your vacation is almost as great as actually going on it. 

If you saved vacation time for years and years, you'd be infuriated if suddenly your company wanted to drain it away without your say-so. Just check out this story of Jimmy, who worked at the same company for 43 years! He was a very valuable employee… key word being "was." 

Next, read about some therapists who could really use a refresher course on the tricks of their trade, like one person who shared that "The TikTok her therapist was watching... started playing on full volume." 

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  • 01

    "Get rid of my vacation? Have fun replacing me."

    I worked at a company that gave out exorbitant amounts of vacation. Anyone who worked there for 25+ years received 8 weeks of vacation and 2 weeks of personal time. This was a family owned company, but rather large. We ran 3 shifts totaling 250+ people.
    via u/Rusticwhiskey
  • 02
    Enter Jimmy. Jimmy was a grissled old man, he started at the company when he was just 20, now he was 63 and gave absolutely zero sh s. Jimmy also knew how to make a specific part for our product, him and one other higher up in the office.
    via u/Rusticwhiskey
  • 03
    One day the plant owner comes out and announces he's selling to a corporation. He's older and ready to retire, he promises that there will be very little change and wishes us all well. The new company comes in and immediately goes after many of the great benefits we had. The first thing they do is cut everyone's max vacation down to 4 weeks, and do completely away with personal time. Anyone who's maxed out had until December
    via u/Rusticwhiskey
  • 04
    31st of that year to use it up, and they wouldn't pay it out. They then go into the office and clean house, firing anyone who's close to retirement. Including Jimmy's back up. But they also do away with one very important rule. You no longer have to get vacation approved, you can just call in and take it.
    via u/Rusticwhiskey
  • 05
    Jimmy is ped, and they know it. They realize he's the only one in the building that can do his job now. So they hire a new kid for him to train, most likely to permanently replace Jimmy. So Jimmy does what anyone would do. He calls in the first training day for the new hire, and lets us know he's going to use all of his PTO at once, and promptly takes 10 weeks off.
    via u/Rusticwhiskey
  • 06
    We had a back stock of parts he had made, so it wasn't too unnerving. But for 10 weeks, Jimmy went and applied to other jobs, found one, and started. Fast forward 10 weeks, Its the day Jimmy is supposed to return. He doesn't. For two days they try calling him, and even go to his house. He's nowhere to be found. Finally on day three he calls and resigns, and they lose their sh. The parts he makes are specialized and patented by the
    via u/Rusticwhiskey
  • 07
    original founder, you can't just hire someone off the street to make them. What eventually happened was they had to contract the original owner to come in a teach some new hires how to make them, and when he found out what all they had done it p he charged them a 7 figure ed him off. The last I heard contract to teach them how to produce the parts, and they had to pony up, or close down.
    via u/Rusticwhiskey
  • 08
    Moral of the story, don't f with people's vacation time. Edit: Jimmy made and electronic control module that was sealed and stayed fixed in a poured unit made of a two part epoxy.
    via u/Rusticwhiskey
  • 09
    Cheezburger Image 10512679680
    via Getty Images For Unsplash+

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

  • 10
    Edit #2: Jimmy didn't exactly "Miss out" on a seven figure contract and had zero chance to take one. He left, said f and moved on. When they em contacted the previous owner and explained the situation it was basically a "you need my help? It'll cost 1mil." Type of conversation.
    via u/Rusticwhiskey
  • 11
    Final update: Thank you everyone for all of the attention this received! I had no idea this would blow up like this. I have immediate family working with the company still, so if I hear of anymore rumblings I'll fill you all in. Also, I worked here for four years. I have a few other Jimmy stories I may post at other times on the appropriate reddits. Thank you all again!
    via u/Rusticwhiskey
  • 12
    Kozeyekan_ Company is sold. New owners say nothing will change. Lots of stuff changes for the worse. A tale as old as time.
    via u/Kozeyekan_
  • 13
    [deleted] Jimmy don't take sh. Good for Jimmy.
    via u/[deleted]
  • 14
    Cheezburger Image 10512679936
    via Dan Senior for Unsplash+

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

  • 15
    CapnTreee As an old guy who has been a tech exec at a dozens of companies, including being brought in on takeovers, let me confirm that this is SO real. Not as bad as entitled next generation owner whelps who haven't a clue about running anything and then go firing key people in a hissy fit crippling the company.
    via u/CapnTreee
  • 16
    Both outsiders and next gen owners have rarely a clue about the 'secret sauce' that made the original owner so successful. Better than average vacation or share options make for FAR better employees.. alter that at your peril.
    via u/CapnTreee
  • 17
    INTO_NIGHT Save a dime to pay 7 figures great model by most companies
    via u/INTO_NIGHT
  • 18
    morgan423 Another moral of the story: if only two people in the company know how to do critical function X, don't go below two people ever who know how to do that. Get a third person trained on doing it before releasing either of the original two.
    via u/morgan423

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boss workplace-stories toxic-workplace work vacation time workplace retirement vacation
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