Worker Admits To Her Boss That She's Struggling To Pay For Basic Necessities & Gets Tone-Deaf Response

Last updated on Apr 27, 2026

employee telling her boss about her money problems Branislav Nenin | Shutterstock
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As the disconnect between the productivity and wages of working-class Americans continues to widen, many people are finding other ways to supplement their income.

Solutions like finding a side hustle and looking for employment elsewhere with a higher salary are always an option, but the tough, oversaturated job market is making this more difficult. So others are simply asking their employer point-blank for a raise. It's a tricky conversation to have, as one woman learned from her own boss's disappointing response.

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The worker shared the tone-deaf response she received from her boss after admitting that she's struggling with money.

An employee named MaryAnna Chewning was just trying to have a real conversation with her boss when the other woman made her shut down completely. She explained that she opened up about how much she struggled with paying for the basics like groceries a few weeks ago in a TikTok video.

Chewning seemed to be trying to hint at the fact that a raise would be helpful. Broaching the pay raise conversation at work can be incredibly daunting, especially if you don't know what to expect from your boss. Chewning's boss, for example, only replied in a tone-deaf manner.

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"She told me that she paid for all of her kids' private school," Chewning recounted. "She's paying for all three of her kids to go to college. Her husband is a lawyer, and they live in a multi-million dollar home, and she was telling me if she didn't have to pay for all of that, she would be rolling in the dough right now."

Chewning tried to remain positive and said she knew her boss was trying to relate to her in her own way, but having the ability to pay for your child's private school education and eventual college tuition isn't comparable to having $60,000 in student debt, like Chewning does.

While Chewning struggles to pay for groceries, her boss pays for her kid's school out of pocket. Her boss could easily enroll her children in public school to save money if it's such an issue, but Chewning's problems aren't that simple.

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This type of response from a boss is why people are afraid to ask for raises in the first place.

This nonchalant, "trying to act relatable" attitude from a boss can be extremely disheartening, especially in Chewning's case, where she was genuinely trying to have a professional conversation but was instead indirectly told that she should suck it up because everyone is also "struggling." However, her boss's definition of struggling is rather different than that of the majority of the population.

worker talking to her boss about a raise aldomurillo | Canva Pro

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According to an analysis from Brookings, one-third of Americans are no longer able to afford essential purchases that many in previous generations barely gave a second thought to. Similarly, in a survey by MarketWatch Guides, 57% of the U.S. population reported living paycheck to paycheck.

This is such a big problem that it's not something you can simply sweep under the rug, so you don't have to talk about it. Instead of empathizing or expressing concern that an employee is coming to you with the devastating news that they are essentially living paycheck to paycheck, Chewning's boss just further widened the gap between her privileged life and the reality of her employees' struggling experiences.

RELATED: Worker Called Their Boss 'Dense' In Front Of The Entire Office & It Had A Very Unexpected Result

Some bosses are doing what they can to break these toxic patterns.

Chelsea Fagan, the CEO and co-founder of the media startup company The Financial Diet, became the perfect example of a humble and compassionate boss after admitting that she has a $90,000 salary and earns the fifth most at the company.

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She explained on TikTok that her decision was really a "selfish" choice but that more executives should do it, too. Fagan doesn't agree with the idea that the average executive in a company's leadership works harder and deserves to be paid more than someone working underneath them who makes minimum wage.

kind boss trying to help her employees www.kaboompics.com | Pexels

"You can't relate to people; you can't understand people. I'm already pretty different than a lot of family, friends, and people in my life. How much more removed from normal life do I wanna be?" she questioned. "Anything I want, I can have, and the idea that you should always be striving for more money is one of the reasons why Americans are often so unhappy, even when they do have money."

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Instead of hoarding money and squeezing employees, employers should be more willing to compensate fairly and address issues with an actual solution. Trying to be "relatable" to employees who are pleading for a pay raise isn't going to pay their rent or buy them groceries.

RELATED: Most People Have Given Up Treating Themselves To A Much-Loved Daily Habit Because It's Gotten Way Too Expensive

Nia Tipton is a staff writer with a bachelor's degree in creative writing and journalism who covers news and lifestyle topics that focus on psychology, relationships, and the human experience.

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