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my boss makes me wear her clothes, eat her food, and say I’m grateful for my job

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This post, my boss makes me wear her clothes, eat her food, and say I’m grateful for my job , was originally published by Alison Green on Ask a Manager.

A reader writes:

I was hired about six months ago at a small business. I’m in my mid-20s and this my first professional job after completing grad school. It’s just me, the owner/director, and a part-time assistant. Because we’re such a small office, I spend a lot of time one-on-one with my boss. Sometimes she’s a lovely person, other times she’s quite difficult to handle. She’s very particular in how things get done and likes to micromanage, but I understand that this is her business and happy to comply with her instructions. But one problem I haven’t figured out how to deal with is her expectation that I be more grateful for the job.

She constantly remarks things like “this is such a good job,” “I give you such great pay/hours,” “You kids don’t appreciate how good I am to you,” and “No other job would treat you this well.” I always respond I’m grateful for the opportunity, but if my answer doesn’t satisfy her expectations, I get a lecture about how I need to be more grateful/thankful. (Also for reference, I work 9-5 5 days a week, and make a $35,000 in New York City.)

Boss claims she likes to mentor young women, which I do appreciate, but most of the time it’s just mothering. For example, constantly reminding me to watch my purse on the subway, wear a helmet when I bike (which i always do) or explaining to me how to wash my hands properly (!) She’s constantly bringing in food, and then offering it to us multiple times a day. “Why don’t you eat a banana?” “I brought you some good soup,” “Take home this beet salad.” Etc. Whenever I politely decline, she gets offended. So I’ve taken to choking down food I don’t want/secretly throwing it away. She caught me doing that one time and I was subjected to a tirade of how ungrateful I was.

Boss has also brought me her old dresses and jackets, makes me parade around the office and then asks that I wear them on certain days. Most of the time I comply, because it’s easier than turning her down and I don’t want to hurt her feelings, but it makes me uncomfortable.

I almost got fired last month. On my way to the store to pick up dog food before work, I fell through a loading hatch on the street, broke two ribs and hit my head. I was in a daze the whole way to the hospital and by the time I was finished with my MRI, it was 45 minutes after I was supposed to be at work. I called Boss as soon as the doctor let me out and she was very upset that I didn’t call her right away. I got home, went to bed on painkillers, and sent her an email that evening detailing the whole story. I understand that she was worried when I didn’t show up, and apologized profusely and assured her I would be at work the next day. When I came again, she berated me for failing to call, accused me of not being grateful and not caring about my job, and actually posted my job on a hiring site and made me beg for her to take the posting down.

We’ve moved on from that incident, and I am trying to tough it out for another six months before I start job hunting, and there are aspects of the job that I like. But now I’ve run into a new problem. When I received my tax documents, I got a 1099 instead of a W-2. I am definitely not a contract employee. I am expected to work 9-5, 5 days a week, I must be at the office, I receive a salary check weekly, etc. I want to approach this with her, but I’m afraid I’ll just get another lecture about how I’m ungrateful, this is a good job, and that if I push the issue, I’ll get fired. And if I do get fired, I won’t be eligible for unemployment because I’ve been classified a contract employee.

How do I best approach this with her while assuring her I’m grateful for the job? I’m still new to the workforce and have no experience handling these type of situations. Any advice on how to navigate this would be greatly appreciated.

First, start actively looking for a new job. Do not wait six months. Do not wait one month! Start now.

Working for a three-person business with a boss who expects constant supplication, demands that you wear her clothes, and responds to your serious accident by putting up a job ad that she makes you beg to remove is not doing you any professional favors. None of what you described is normal, and it’s not okay. I’m really skeptical that you’re picking up great professional skills there, and you’re at the very start of your career and can easily have a short-term stay on your resume without it harming you.

So stop delaying the job search. Get out ASAP. (And target larger companies when you do; tiny businesses like this are just too rife with problems.)

As for her treating you as a 1099 contractor rather than an employee (and thus not paying your payroll taxes), that’s illegal. Not maybe illegal, not a little illegal — entirely illegal. And really unfair to you, since it means you’re now responsible for the payroll taxes and Social Security she should have been been paying on your behalf. (By the way, pay attention to your pay stubs! If she’s been paying you as a contractor this whole time, you should have seen it on your pay stubs when no taxes were coming out.)

The way to address it is to be incredibly matter-of-fact: “I got my tax documents and it looks like I’ve been paid as a 1099 contractor. We can get in a lot of trouble for that, because federal law is very strict about who can be treated like a contractor versus an employee. Can we redo this so the tax forms are correct and the company’s share of my payroll taxes are taken care to?” If she pushes back by telling you you’re not sufficiently grateful for your job, you can say, “It’s not about being grateful or not; it’s about what the law says we have to do. We could get in legal trouble for this, and so I want to make sure it’s fixed.”

If she doesn’t fix this on her own, you can file with the IRS asking them to resolve it (here’s the form to submit, and here’s info about how to handle the whole tax situation). You also don’t have to do this now; if you’re worried she will retaliate against you, you can wait until you’ve left this job and do it then. You have up to three years to amend your tax return and get back the money you shouldn’t have had to pay out.

But the most important thing here is to focus hard on getting out of there. Working for a toxic boss can really mess with your head, and you can carry the dysfunctional habits you form there with you to future jobs. That’s especially true when it’s your first professional job and you’re still forming your ideas of what’s normal and what you should and shouldn’t accommodate. So — you can deal with the tax situation later if you need to. Right now, make your top priority a new job.

Read an update to this letter here.


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