Dear Businesslady: We Think One Of These Letters Is Fake -The Toast

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Email us questions at, subject line “businesslady.” Previous installments can be found here.

Dear Businesslady,

I have a situation at work that is stressing me the heck out! I’ve been an associate at my current firm for about three years now. It’s a great place to work and I think I’m fairly good at my job. When I first started, I worked most closely with one of the partners, let’s call her Julie. At first, I worked mostly on whatever Julie needed help with, but over the past year or so I have taken on more projects on my own. Since I started at the firm, Julie has had two kids and gone on maternity leave twice. During that time, I managed her projects, and handed them back over to her when she got back.

We are now working on a major project that requires multiple people — there is certainly more than enough work to go around! The problem is that Julie is driving me crazy. She has taken three vacations already this year, each more than a week long, and was also out sick for more than a week. When she is out, her tasks fall to me. That’s plenty stressful, as I’ve had to do two people’s jobs for over a month all told so far this year. But even worse, when she gets back she is very passive aggressive and possessive. She never thanks me for picking up the slack (petty to want, I know, but it would be nice!) and she criticizes minor errors. The last in particular drives me crazy because she is right! I should have formatted that part of the report differently! But mistakes like that happen when you are doing two people’s jobs.

Our firm is small, and while we do have a set leave policy (which she’s already exceeded for the year), it is not strictly enforced. And even when she is here, she’s only half present — she’ll get in late and leave early, and make mistakes she shouldn’t. I get that being a parent to two kids under three is stressful, and it’s a position I might one day find myself in. I am trying to find compassion here. If it were just picking up the slack on projects, I would be stressed but could handle it. But the fact that she is not just unappreciative, but actually hostile is really unpleasant.

Julie and I worked well together in the past, and there are parts of her job that I simply could not do. She is much better at dealing with clients than I am, for example. I don’t want her job — I just want her to do her job! I feel like she thinks I’m All About Eve-ing her, and I feel like she is taking advantage of me. It’s not a good situation, and I’m not sure how to fix it. Any advice would be much appreciated!

Dear Stressed,

I’m tackling coworker drama today (more on that below), and I think a lot of people will relate to the situation you’re struggling with. It’s one thing to have a coworker whose antics are so comically awful that they almost become a source of entertainment. It’s another thing to work closely with someone who is making your work-life miserable through a series of individually minor incidents. And then once you get to the point where your default mode is “annoyed” (what some might call the bitch-eating-crackers phase) it’s almost impossible to proceed with a normal, healthy, well-functioning workplace relationship.

But the fact that your compassion well hasn’t run completely dry yet makes me feel like there’s hope here. And you offer some useful perspective on where Julie’s coming from too, even if it’s (understandably) colored by your own frustration.

I think the key word in your letter is “possessive.” In keeping with a grand tradition of counterproductive human behaviors, it’s pretty common for people who are worried about their place in the office hierarchy to double down on reinforcing it. This is in no way effective, and it has the added benefit of irritating everyone who’s around to see it happening. (Pro tip to those who are prone to this tendency: stop it right now; you’re not fooling anyone, and no one cares to hear your thoughts on how integral you are.)

In addition to the demands of parenthood, I’m sure Julie actively feels like The Person Who’s Not Pulling Her Weight Anymore—on top of all the other baggage that comes with combining motherhood with a demanding career. By nitpicking your work, she’s reasserting her status; by not thanking you, she’s probably trying to develop a counter-narrative in which she unequivocally deserves this level of assistance due to her unassailable importance. There may even be a dimension in which your previous camaraderie makes you feel “safe” as a dumping ground for all her work-related insecurities.

All of which is bullshit, obviously, and now that it’s starting to wear on you, it’s time to reboot your dynamic. You guys need to have a conversation—not about these issues specifically, but also not not about them either. I’m a fan of the “go out to lunch” technique, but you can pick something that fits your particular history: lunch, coffee, happy hour, whatever. Pick a moment when it seems like you both have the time to talk one-on-one and make it happen.

When you do sit down together, begin by establishing common ground. How are the kiddos? What’s the deal with [show you both enjoy/longstanding workplace inside joke/etc.]? If she complains about her own work stuff, try to think about how that might be influencing some of her more negative behavior.

At some point—as naturally as possible—you want to pivot to the “let’s fix this” part of the talk. The exact path you take will depend on your respective personalities and the vibe of the conversation thus far, but you might start with: “I feel like you’ve been really frustrated by some of the minor mistakes I’ve been making, and I feel like I’ve been making them because I’m so overwhelmed. How can we work together to get things back on track?” Ideally this will open up a dialogue where you can each accept responsibility for the ways you’ve contributed to the current pattern, vent (nicely) about external factors, and develop a plan for avoiding the same issues in the future. If all goes according to plan, the result will be a hard reset on your working relationship that keeps the negativity at bay for a while.

Of course, that’s the optimistic view of things. The pessimist in me says that this will do nothing, or possibly even exacerbate the worst parts of your dynamic in a kicking-the-hornet’s’-nest kind of way. But you should do it anyway.

Even if The Talk goes horribly awry, you’ll still be in a better spot: you’ll have gotten things off your chest, you’ll have a better sense of where Julie is coming from, and you’ll know that you you at least tried to patch things up. A reasonable person in Julie’s shoes will see your actions as an olive branch and will welcome the opportunity to make everyone’s work-life easier. An unreasonable person will double down on everything that’s causing problems in the first place, implicitly declaring “I am not a reasonable person” in the process. Knowing your enemy—including the fact that they are, in fact, your enemy—is crucial to overcoming any kind of challenge. So when you view things in a big-picture context, hashing things out with Julie is a win/win.

If you conversation is productive, then your problem is solved right there. If not, then you can decide what the best course of action is based on the current reality (i.e., that Julie is not going to change). Maybe you talk to your boss/colleagues about your workload and developing strategies for minimizing Julie’s involvement. Maybe you mentally append “okay, but you’re THE WORRRRRRRST” after every interaction you have with her. Maybe you look for a new job and leave your coworkers to deal with that nonsense. Maybe some combination of all the above. Whatever the solution, you’ll be able to pursue it with a clear conscience, unburdened by “maybe I’d be more understanding if I had kids too” and “but we used to work so well together.”

My hope, though, is that she’ll be relieved to have the chance to start afresh. Workplace possessiveness, like so many self-defeating habits, is hard to stop once it starts. But if she’s able to see you as an ally—and not a vulture coming to pick at the carcass of her professional relevance—she might be able to relax into her old self again.


*        *        *

Dear Businesslady,

I’m a woman in my 60s, and I need some advice about how to deal with the changing values of the workplace. I work for a midsized company, but my division has changed little in the past decade. Most of my colleagues are past 50. The one change has been the addition of “Molly” who started 4 years ago in a part-time position, and is now in her late 20s. I know many details of Molly’s life, including the fact that she lives with her parents and the reason she only works part-time is so she can pursue her artistic ambitions. Though she’s not had any real success, she firmly believes that she’s going to ‘make it big’ and somehow become rich and famous.

I think that is ridiculous. I been on my own since I was 16, and I cannot fathom how a woman pushing 30 feels that she can sponge off her parents. I’ve told her many times that she needs to grow up and take responsibility for herself. I’ve encouraged her toward full-time jobs within the company. But she has gotten hostile toward my advice, and now I’ve been told by HR that I must restrict my conversations with her to what’s necessary for the job!

What do I do? How can I trust the decisions she makes at work when I know that she makes such poor ones in her personal life? Does character simply not matter anymore? When I was young, a woman who did not know her place was quickly reminded, and they were the better off for it. Some of my colleagues are retiring soon, so it’s quite possible that we could end up with a few more Mollys in the division. Have arrogance and ridiculous ambition replaced the value of hard work and being grateful for what one has? Has the workplace changed so much, or have I passed through the looking glass?

Call me,

Knows my Place

Dear Place-Knower,

This letter is a trip. Nicole Cliffe and I even think it might be fake. But whether it’s legit, utterly fabricated, or somewhere in between (perhaps penned by “Molly” as a way of thinking through the motivations of her busybody coworker?), I think it’s a useful jumping-off point for discussing the potential problems of entangling the personal and the professional.

The thing is, as much as it’s easy to say, “oh my god, lady, back off on Molly already,” I suspect we’ve all been in a similar position—albeit, hopefully, less outspoken about it. Almost everyone has had a coworker whose life is just one giant trainwreck, and who generates an internal monologue to match: how can someone get evicted twice / you’re clearly about to get dumped / no I can’t lend you $20 / why on earth would you think that outfit was work-appropriate / yes of course the “cruise” you “won” turned out to be a scam / etc. etc. etc.  People like this seem to exist to make us feel better about our own degree of shit-together-having while simultaneously reminding us how petty and judgmental we’re capable of being. And yes, they’re a huge pain to work with.

Molly sounds like she’s suffering from a serious maturity deficit, and it’s probably true that she could stand to be more realistic about her career prospects. But if you’ve been banging that drum so hard that HR has gotten involved, then you’re out of line here too. It’s just not okay to appoint yourself as your colleague’s life coach, no matter how well-intentioned (or right) you happen to be. It’s not really okay to do this with your friends either (whether work-friends or otherwise); if someone specifically asks, “here’s a problem I’d like your help in fixing,” then maybe share your suggestions, but still be prepared to have them ultimately ignored or discarded.

A few years back, I was venting to my grandma and some of her similarly octogenarian associates about a friend who was making Many Choices I Deemed Incorrect. At the end of my rant, I sighed and said, “But of course, saying this to him would do nothing—he’ll either figure it out, or he won’t, and all I can do is just be supportive from a distance.” Grandma and crew all nodded so vigorously and so meaningfully that it felt like an affirmation: yes, you’ve finally figured out the core truth of human relationships. If you’ve been independently navigating the world for close to half a century, surely you’ve had the opportunity to come to this realization as well—micromanaging another person’s life won’t just aggravate them, it’s also a flat-out waste of your time. There are plenty of things I’d like to go back and tell my younger self in theory, but I also know that people were telling me those things, in real time, and I didn’t see the wisdom in their advice until I’d learned the lessons for myself. Molly will grow up, or she won’t, but either way you need to accept that it’s not your problem.

So, with that out of the way, let me quickly answer your real questions: What do I do? Treat her like any other coworker and limit your chitchat to neutral topics free of your own personal judgment. How can I trust the decisions she makes at work when I know that she makes such poor ones in her personal life? Pretend you don’t know about her personal life, and if she does screw up something work-related, see “treat her like any other coworker” above.

The rest of your queries are basically rhetorical, so I’ll leave them be—although I should note that I have a hard time sympathizing with your laments over the supposedly “changed workplace.” First of all, I’d argue that people have been making bad choices for as long as they’ve had the free will to do so; second of all, it’s dangerous to romanticize an era that was basically defined by its exclusion or marginalization of everyone who wasn’t a straight white male. So there.

It’s a big world out there, and for all the people who are badass and thoughtful and funny and smart and perceptive, there are also people who are deluded and ungrateful and entitled and immature and incompetent. It’s not an exact science, but I’m pretty sure that the best way to edge yourself toward the former camp is to avoid scrutinizing the latter one. And if you simply must rail against the poor decision-making that inevitably surrounds us all, do it on your own time.


Businesslady is in her early 30s and somehow managed to find a rewarding career despite her allegedly useless degree in the humanities. Her job history includes everything from food service to retail to corporate nonsense, but she currently does writing and editing for a nonprofit, and devotes the rest of her life to playing video games, patronizing bars, and spending way too much time on the internet.

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