Boss pressures employee to use vacation time, employee demands money to plan his trip: 'It quickly turned into a Boomer v. Millennial Showdown'

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Ben Weiss • Writer and Editor
Jun 1, 2024 8:00 AM EDT

It's easy for the boss to tell their employee to go on a vacation somewhere nice. It's harder when you don't have the funds to plan a trip like that.

This overworked employee recently learned that his company was doing away with bonuses and was therefore losing out on $20K that year. That was money he was planning on using for a real vacation, but without that extra money, he really could not afford to plan a trip. All of his income was now going into living expenses, as the cost of living was rising exponentially in his area. So when his boss pressured him to go on a "real trip," this Redditor could not maintain his composure and told his boss that he was not getting paid enough to afford the kind of vacation that his higher-ups frequently take. Eventually, the argument got personal and generational.

Keep scrolling below for the full exchange and the best reactions from folks in the comments section. For more stories like this, check out this post about a worker who refused to accept the mandated return to office.

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  • 01
    "Boss told me I needed to take a vacation, I asked if he had vacation money" DOL
    via Money Knack
  • 02
    During our Mid year assessment my boss told me I had too many vacation days saved up (I have 22 days I HAVE to use by EOY) and I needed to start using them soon since he didn't want a bunch of us waiting until the end of the year to use our time. I told him I didn't have a reason
    via u/Koriino06
  • 03
    to take time off and would probably do so when school started back up so I could be more active in my kids school and their happenings. He responded by saying "why don't you take a vacation? You could go somewhere nice like Florida or Alaska,
    via u/Koriino06
  • 04
    even traveling out of country isn't that expensive!" I literally stopped what I was doing and said "do you have vacation money for me?" He was flabbergasted that I couldn't afford a random vacation for an average sized family.
    via u/Koriino06
  • 05
    Backstory: I'm decently employed, hate my job I guess as the people I work with are idiots and the only person I genuinely get along with is my immediate supervisor (we were friends before this job, we worked together previously and kept in touch after leaving previous company, ended up at new company
    via u/Koriino06
  • 06
    together years later within a day of each other). Benefits but at least I have them and the rest of my family are covered in case something happens. Main benefit is working from home (told us to come back in office but only one person complied so that demand died quickly),
    via u/Koriino06
  • 07
    basically being able to set my own schedule (ie as long as my work is done and emails are answered no one cares) and I WAS decently paid. I say WAS because this year our company decided not to do raises or bonuses (about $20k altogether that I'm losing out on for the year which is a lot of money) but cost of living has increased exponentially in my area. I'm talking about my expenses increased by almost $1800/month including rent, insurance, food, etc.
    via u/Koriino06
  • 08
    Luckily I could almost afford the increase (it takes all my monthly disposable income and I had to stop paying on my credit card) but it's hard to do anything that cost money as most of mine just goes to bills.
    via u/Koriino06
  • 09
    Anyways, back to the convo: he was shocked to say the least. He asked why I didn't have anything saved up or put aside for something like this. I asked him how he was able to afford his stuff and he said he wasn't affected too much by the lack of bonus and raise because he owns everything
    via u/Koriino06
  • 10
    and all his money goes to investing (his investments pay for his monthly expenses so he literally doesn't use his check for anything) and that if I owned my car and had a house (I rent) then I could afford to do a vacation. Long story short I tried to explain the difference between his growing up and mine in the current economy
    via u/Koriino06
  • 11
    and it quickly turned into a boomer v millennial showdown. I gave up and told him I wasn't going to be taking a vacation and that I'll be saving it up until the end of the year so they'll have more to pay out when I leave. Havent heard from him since. My immediate supervisor said he's freaking out because he thinks I'm trying to leave and should be grateful for being in a better
    via u/Koriino06
  • 12
    position than most. Her response to him? "Maybe you should invest in his vacation since you don't need the additional funds?" Apparently he is contemplating it so may be a win for me?
    via u/Koriino06
  • 13
    • scene_missing · 7 hr. ago On one hand, I get what you're saying. On the other, you need to take your vacation time no matter what. Even if it's just to spend the day at the park or sleep in and play games or literally anything.
    via u/Koriino06
  • 14
    anonymous2278.4 hr. ago My ex-boss told me the same thing once. I actually did have the money so I tried to take a couple. One for a weekend where I needed Friday off, and one for a week with some friends. He put up a huge fight about giving me the time off. So stupid, why tell me to take vacations if you don't want me taking time off to do it?
    via u/Koriino06
  • 15
    GrizzlyRiverRampage. 8 hr. ago This showdown was excellent until the freakout over insinuating departure. You're already applying for other remote jobs with 20k bonuses, right? r/remotework will have suggestions. Yes, I know the sub we're in →
    via u/Koriino06
  • 16
    LJski 3 hr. ago Your boss is saying take your time off. What you do with it is up to you, but a good boss will encourage you to of the office.
    via u/Koriino06
  • 17
    corkbeverly 2 hr. ago take a staycation that's what many do. Might be nice to spend time with your kids even if you don't go somewhere? Time off when the kids are out of school is fun, even at home. You can take them to the park, find free or cheap activities near home.
    via u/Koriino06
  • 18
    Koriino06 OP. 18 min. ago Definitely agree! My girls stay with my most of the day and we spend a lot of time playing games, watching movies, etc while I'm working so we definitely keep busy.
    via u/Koriino06

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workplace-stories work stories toxic-workplace job work Horrible Bosses reddit thread Reddit company toxic-work-environment
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