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Antiwork

Work Related Struggle: Spending my own Money

I work for an organization that houses and cares for people with developmental disabilities. My job there is entertainment, basically. We have recreational outings, events, and have a classroom where I go if we arent having one of those events or outings. When I first started this position, it was ran by another person in a different department, and I was mostly in class. Last year, about this time, they made a new team for just recreational type people. It's been great, lots of outings, events, even more than before. Problem is, my boss is more and more wanting to get things out of our own pockets. Never anything huge, but if you want to go all out, it's highly encouraged and the boss often goes all out themselves. It started with some cupcakes here… Something for a cookout here… I started off not wanting to, knowing if I started…


I work for an organization that houses and cares for people with developmental disabilities. My job there is entertainment, basically. We have recreational outings, events, and have a classroom where I go if we arent having one of those events or outings.
When I first started this position, it was ran by another person in a different department, and I was mostly in class.
Last year, about this time, they made a new team for just recreational type people. It's been great, lots of outings, events, even more than before.
Problem is, my boss is more and more wanting to get things out of our own pockets.
Never anything huge, but if you want to go all out, it's highly encouraged and the boss often goes all out themselves.
It started with some cupcakes here… Something for a cookout here…
I started off not wanting to, knowing if I started doing it (like the 10 other people who do this job) the amount would just get higher and higher as they'd become accustomed to expecting it.
Well, I wasn't wrong. A lot of the events we've gone to (minus restaurants) the chaperones get in for free. We are each watching multiple people at a time (unless they're on higher supervisory level, then I may just watch them solely) so you're actually working and not just enjoying everything for free. Yes, I enjoy the things obviously, and am so happy the people get to experience it.

Like I said, I had a feeling this would.become the trend of us having to put our own money in.
So now, they want us to go sit through something for a few hours, which I have NO INTEREST IN whatsoever for myself. And it's $20 to get in!!
I'm on a budget. No one who works for this company is rolling in dough. They might have split expenses, but I don't! I'm a single (childless) person, and I'm not necessarily struggling but I'm not thriving either.

How do I politely tell my boss I cannot continue to pay out of pocket for these things?
Many things I've already sat out of (eating, extra activities, playing games for myself at carnivals, not having the same custom shirt as others, etc) and I know everyone rolls their eyes at it, calls me cheap or whatever. I'm just sick of going to work and having to pay for it, instead of the other way around.
My boss has a boss, and their boss has a boss, and so on and so forth. I don't want anyone to get in trouble, especially myself… But also don't feel like I deserve to get looked down onto.

If I have to go to this $20 event I'm not even interested in (not being interested is where the $20 issue comes to play), I'll basically have to pay to go in, because my job would be to supervise these people, feed them, make sure they can get to the bathroom and such, which would require me being in there. My job is to go to these things with them, but I cannot continuously pay out of pocket for it!!
I already get talked to about not saying things right… I'm told it's my deliverance… So please help me so I can get my point across without sounding like a crabby old lady.

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