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Generosity is many things, but mandatory isn’t one of them.

One employee’s boss decided his entire team would spend a day feeding the homeless.

That may sound nice in theory, but here’s the catch: he expected every employee to pay for it out of their own pocket.

He announced the plan without asking anyone, drove the team to the grocery store, and waited for everyone to start filling carts with about $50 worth of food. This employee wasn’t making much, so $50 was no chump change for him.

When he pushed back, just a little, his boss acted shocked that anyone would object to something so charitable.

Keep reading for the full story.

My boss made my team buy food for the homeless

First off, I’m not saying buying food for the homeless is wrong by any stretch of means, but my boss just decided that our whole work team was going to do that one day, without actually asking any of us.

The boss was clear his employees were going to do whatever he said.

He just announced it and then took us all to the grocery store and expected us to buy around fifty dollars’ worth of food that we were going to then hand out to random homeless people on the street.

This wasn’t just pocket money for this employee.

At the time, I wasn’t making a lot, and so fifty dollars was a good deal of money for me to spend.

And when I protested (not by much, but a little), he got really shocked about it. Like, I have to eat too.

The whole thing put a massively bad taste in the employee’s mouth.

It was just so bizarre that he just decided that we would all go spend our own money on a non-work-related thing, and we just had to go along with it.

Donating to charity is supposed to come from the heart.

What did Reddit have to say?

This user thinks this employee should have worked harder to put his foot down.

There are way better ways to help the less fortunate.

There’s a real disconnect here.

If you enjoyed this story, check out this post about a customer service rep who hung up and called a customer back to get around a time limit, but ended up getting an award instead of a reprimand after the customer praised his service.

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This commenter calls this out for what it really is.

This boss wanted credit for generosity without paying for it.

He picked a cause nobody could argue with, announced it as a plan, then used his employees’ powerlessness to bankroll it. That’s pretty despicable when you really think about it.

Feeding people is a good thing to do, but charitable acts should come from the heart. And ideally they’re performed when someone is in a solid financial position to do so.

A real leader pays for his own good deeds.

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Author

Benjamin Cottrell

Benjamin Cottrell | Assistant Editor, Internet Culture

Benjamin Cottrell is an Assistant Editor and contributing writer at TwistedSifter, specializing in internet culture, viral social dynamics, and the moral complexities of online communities. He brings a highly analytical, editorial voice to his reporting on workplace conflicts, malicious compliance, and interpersonal drama, with a specific focus on nuanced stories that lack an obvious villain.

As a published author of rhetorical criticism, Benjamin leverages his academic background in human communication to dissect and elevate viral social media threads. Instead of simply summarizing events, he provides readers with balanced, deep-dive commentary into why the internet reacts the way it does. In addition to his cultural reporting, he is an experienced fine art photography essayist and video game reviewer.

When he isn’t analyzing the latest viral debates, Benjamin is usually chipping away at his extensive video game backlog, hunting down the best new restaurants, or out exploring the city with a camera in hand.

Connect with Benjamin on Instagram and read more of his essays on Substack.