I’ve Spent My Career Working for Entitled Rich People. It Always Ends the Same Way.

Good Job is Slate’s advice column on work. Have a workplace problem big or small? Send it to Laura Helmuth and Doree Shafrir here. (It’s anonymous!)

Dear Good Job,

I have had a really strenuous 15 years of being an employed person, and feel at the end of my rope. The first six years I worked at a daycare, and then I finally decided to take control of my career and pursue nannying. I worked for my first family for two years, then the husband starting home more, so they said they realistically would not have much work for me for an undetermined amount of time, but they would bring me on as they could, which they did. Well, while I was searching for something part time and temporary until I got to go to back to them full time, color me surprised when I saw a job posting of their family looking for a nanny! To this day I still don’t know what I did wrong in that job. Obviously I felt strung along and betrayed, and I told them I quit.

I tried to see it as a silver lining and a chance to find a higher paying job, which I did, this time through an agency. This is where things got really bad. The mother was very high strung and type A, and unlike other jobs where I could report to an HR, there was no one to report her bad behavior to. I’ll admit I didn’t do everything perfectly, but I was working 10-hour-plus days, with three children, two of whom had behavior issues (I was getting punched, kicked scratched by two very angry 8-year-olds). In addition to being the nanny, I was also the housekeeper, house manager, and tutor. And if I so much as left the clothes washer door shut, I might as well have invited black mold into the house. Yelling and screaming in that house was very common. One time, she yelled at me so badly for daring to miss that her son had rinsed markers in a 200-year-old Italian marble sink that I went home and immediately threw up from the stress. (The markers rinsed out with one quick rinse by the way.)

I ended up quitting that job after three years and found a new job for twice the pay as a household manager and personal assistant for a new family. The first two years went great, but the last year was very difficult. I will admit in that job I started to struggle because the mother’s views became very radically far right, and it made me somewhat check out. I also partially checked out because she started yelling at me in text messages and would expect me to follow through on projects with absolutely zero guidance or communication, then be upset when things didn’t happen. Expectations also changed radically that year with no forewarning, so it felt like walking into a minefield anytime I did something. At the end of the summer, she said they don’t need any help any longer and that my time with them is over. A surprise, but fine. Well, I go on agency boards and see basically my job with that family, reposted. Again, the confidence hit and sense of betrayal was immense.

Now I have another job as a full-fime personal assistant for about the same amount of pay, but my confidence is incredibly shot. I feel unsure of people’s intentions, and every time I do something not perfectly with this new job, I’m afraid. Like literally purely afraid. I don’t know how to gain back any self assurance. Frequently, I just wanted to stop working all together. I just don’t know how to move forward.

—Shot Confidence

Dear Shot Confidence,

It really sounds like you’ve been put through the wringer in your last few jobs! You’re describing bosses who are horrible at communication and avoid confrontation, which naturally has made your confidence plummet, and families with kids that seem objectively difficult to handle. This is not in any way a reflection on you as a person! So I do think that part of what’s been happening is a run of somewhat bad luck. That said, there are a few things in your letter that I think are worth a bit of additional self-examination and can perhaps help you move forward more productively.

The common thread I’m seeing is that the end is always coming as a surprise. With the first family, for example, you say that you saw a job posting from the family, but instead of actually discussing it with them directly, you simply quit. I understand that there’s a power dynamic at play here, but it’s important to learn to be able to advocate for yourself and speak up. I would have asked them about the job posting—we don’t actually know why they had it up. Maybe there was a miscommunication and they thought you only wanted part-time hours. We don’t know, and we’ll never know.

I think all of this could be greatly helped by regular check-ins with your bosses, perhaps once a month. I would ask for specific feedback about what’s going well and what needs improving. It’s also an opportunity for you to ask for what you need to succeed at your job and make sure that everyone is communicating respectfully.

One other thing that did ping for me a tad: With the second family, you admit “I didn’t do everything perfectly.” Look, no one expects perfection all of the time. But I feel like there’s a lot left unsaid here, especially when you follow that up with “if I so much as left the clothes washer door shut I might as well have invited black mold into the house.” As someone with a front-loading washer, you DO have to leave the washer door open or the rubber ring gets moldy really quickly. I would also find it very frustrating if I had to remind someone multiple times to leave the washing machine door open! So I would just urge you to do whatever you can to make sure that specific things that your boss asks you to do are always taken care of—whether or not you agree with them. But I do think that open, honest communication from the start is going to go a long way. I’m rooting for you!

Dear Good Job,

I work in senior leadership at a non-profit. There are two people “above” me—my boss, the CEO, and a CFO, plus the board. I have done this work for many, many years, and I’m very good at it. I have been in this particular job for six months. The issue is that, though my title and pay reflect my expertise and seniority, and though the job I interviewed for and accepted was presented to me as a thought partner and advisor for the CEO, I am nearly always kept out of the loop until decisions are already made. At first I thought that perhaps it was just taking my boss some time to get comfortable with me. But I think now that he never intended for me to be an advisor at all.

He will make irreversible decisions that I should have been consulted on and then let me know with a “by the way” in another meeting. When he tells me about things that I should have been involved in, I do speak up. I’ll say, “Thank you for telling me, but the time to bring me in on these decisions is when you’re first considering them, then I can really be of use.” And he’ll always say, “Yes, yes, of course,” but then he drops some other bomb on me next. I’m not just upset about being left out, though there is some of that. I genuinely have expertise that he hired me to utilize and should be utilizing. The decisions he’s telling me about almost always require me to swoop in and fix something, and it would be so much better for everyone if I was involved earlier. And yet he keeps me out. The CFO seems to be privy to everything before it happens, and he and my boss seem very close. I’m looking for other roles, but I’d like to stay here for at least a year. What should I do in the meantime? Just accept that he’s never going to tell me anything? Push harder?

—Out of the Loop

Dear Out of the Loop,

Congratulations, you’ve walked into a dysfunctional workplace! My suspicion is that one of two things is happening: either this is just how the CEO and CFO have always operated, and whoever was in your role before was either OK with it or left because of it, or it’s just going to take the CEO awhile to feel like he can fully trust you and that’s why he’s been cutting you out. I fear that it is the former, and I am quite honestly skeptical that the CEO is going to change. You could try asking for a weekly one-to-one with him to try to get more of a sense of what he’s planning before the decisions become irreversible. I would also start documenting every time something happens where you’re expected to clean up a mess that could have been avoided. I’m also wondering if there’s anyone else in a senior position or on the board who could be an ally for you, or at least give you the real lowdown on what’s going on.

In the meantime, if nothing changes, I would do whatever I could to find another job. I know you said you want to be there a year, but if it’s not working out, I don’t see the harm in leaving before the year is up. I would be shocked if you were the first person in this role to leave for this exact reason. Good luck, and I hope you’re able to come to a resolution that at least feels sustainable for the next few months.

—Doree

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