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

Dear Businesslady,

I started a job about a year ago at a small, woman-centered non-profit organization. My boss, the executive director (“ED”), is a few years older than me. We’re alike in many ways and get along fine, but there seems to be a class/income divide coloring our interactions, and I need help in navigating it. I grew up in a solidly middle-class home where I didn’t lack for much but money wasn’t something ever taken for granted. My husband and I make very decent salaries in our fields but struggle to make ends meet just dealing with basic expenses of a mortgage, food, daycare, etc. ED grew up very well-off and travels in much higher-income circles than I’m used to. We both have several young kids and are juggling the work-life balance, but ED has an au pair to handle the occasional sick day or snow day doctor’s appointment, whereas my husband and I both work full-time and trade off missing work to take care of the kids in these instances. This past winter was pretty brutal in our region. For months I didn’t go more than a couple of weeks without missing work for a school snow day or a kid getting sick. Every time I had to stay home, I did what I could from my laptop while watching the kids and stayed in regular contact, including calling in to meetings. This spring I also ran a major project, which involved putting in about a month of 80-hour workweeks. I understood that in a salaried, not hourly, position, overtime happens, and I never brought up whether this considerable extra time could be credited toward anything.

Last week, I asked for two days off this fall to attend a family wedding, and ED told me that that would put me over the 15 vacation/sick days we get each year, and if I took off for the wedding my pay would be docked or I would have to work a couple of Sundays. She recommended that if I had to miss work in the future, I hire a sitter. I haven’t said anything yet, but I’m kind of steamed at this, especially since I worked so much overtime for the spring project, and have taken pains to get work done from home every time I’ve had to be out of the office. Hiring a sitter is very hard when a kid gets sick on short notice. I think ED is has a case of “au pair privilege” here, and I’m not sure how to ask her to be more flexible.

Dear Steamed,

Let me start by saying I get you—I totally get you. There’s nothing worse than being dinged on “policy” in a way that seems to totally disregard all the above-and-beyond work you’ve been doing. And when you add in something fundamental like “ensure my own children are being looked after,” then multiply that by “boss apparently doesn’t understand that the strategies she uses aren’t workable for me,” you’ve got a perfect storm of resentment waiting to happen.

But while resentment can occasionally crystallize into productive resolve, it mostly just metastasizes into generalized unhappiness that serves no valuable purpose. So in an attempt to avoid that, let’s see what can be done about this situation.

From my view, there are a few separate issues woven together here:

  •        an unusually brutal winter with a correspondingly unusual impact on your kids’ school attendance and health,
  •        a pay/privilege disparity between you and your boss,
  •        a variable workload that sometimes places big demands on your time,
  •        a lack of compensation (official or otherwise) for your above-and-beyond efforts, and
  •        a limited pool of time off that’s meant to cover all absences, both planned and unplanned.

The first two are the “easiest,” in that there’s no changing them. Weather, illness, and bad luck are inevitable, and even if I hope the next few months go by without the words “polar vortex” dominating all media, there’s always Something that will lay waste to your best-laid plans. Similarly, there’s not much that can be done about your boss’s fancypants upbringing and corresponding socioeconomic advantages—and the fact that she makes more money than you makes sense in terms of organizational hierarchy.

So that leaves us with the last three bullet points, which are related but could still benefit from some disentangling.

There are pros and cons to the “all time off is the same” approach—pro, you can take hooky days with impunity and you get more vacation time if you’re generally illness-free; con, a spate of sickness can leave you without any discretionary days off, as you’re finding out. But usually these sorts of policies are governed by a variety of factors beyond employees’ control, and aren’t easily revised, so it’s probably worth accepting that things will remain the same for the foreseeable future.

Now, we’re down to two issues: the time you’ve put in, and the lack of recognition for your extra work. I think the key is right here: “I never brought up whether this considerable extra time could be credited toward anything.” Of course you didn’t! You were doing what needed to be done, and assuming everything else would fall into place. But it didn’t, and now here we are.

In my very first column, I mentioned my (and my dad’s) philosophy of “if ya don’t ask, ya don’t get.” It’s time for you to do some asking and, hopefully, some getting. While some workplaces are strictly opposed to anything with a whiff of “comp time” to it, your boss’s suggestion that you work Sundays to balance out your over-the-limit vacation days implies that she’d be willing to consider it. So whenever there’s an opportune moment—a regular check-in, a meeting that doesn’t take place during a moment of crisis, a day when you’re feeling up to the challenge of a potentially difficult conversation—sit down with her and make your case.

While your kids and their needs are an inextricable part of this, try to keep the focus on your actual work as much as possible. Quickly gloss your childcare situation and the infeasibility of an au pair or regular sitter (no explanation’s needed; just say “it’s not an option for us” if pressed, because it’s none of your boss’s business who watches your kids as long as it’s not interfering with your productivity). Point out that the limited amount of time off you have available can quickly be eaten up by force-majeure misfortunes and ask if there’s any way to translate your long hours during busy periods into schedule flexibility when things are slower. Emphasize how willing you are to meet the organization’s needs regardless of how much it cuts into your personal life, and point to any obvious value you provided in the recent past (“you’ll recall that our donors were thrilled with my presentation,” or whatever’s applicable).

In the course of this discussion you might have to accept that the 80-hour workweeks you put in won’t be able to “count” toward future time off, simply because there wasn’t previously a system in place for doing that. However, I’d start by asking if that time could be applied toward one or two future absences—and if that’s a no-go, you can look gracious by accepting the ruling as part of a broader negotiation.

Another component of the conversation should concern what “working from home” entails. On the one hand, if you’re truly working (as in, treating it as a normal workday), you should have someone else keeping an eye on your progeny. But if this is a case of “kids home from school, neighborhood buried in snow, trying to make some progress on a work project despite being surrounded by tiny distractions,” then there should be some mechanism for acknowledging your efforts to minimize the disruption of your absences.

It’s easy to surrender to inertia regarding things like “what are my obligations to my employer” and “how do we handle time off”—it’s not fun to initiate A Talk and generally not worth it if the issues are few and far between. Once you start feeling grumpy about the way you’re being treated, though, that’s a sign that you need to purge your emotions, think critically about what an ideal arrangement would look like, and make the case to your boss for why you deserve it.

If you don’t get the response you’re hoping for, then you have to decide whether or not you can live with the new reality—but at least you’ll have a more firmly defined sense of what your options are, and most likely you’ll end up in a better spot than where you started. And, if nothing else, you’ll have confidence that your boss knows where you’re coming from, and future discussions can build on that mutual understanding.


orphanblackDear Businesslady,

My colleague, Helena, has been aggressively pursuing friendship with me – the kind of friendship that goes beyond a regular, friendly, positive coworker relationship. I have always been willing to develop deeper friendships with colleagues, but I do not want to be “outside work” friends with Helena for many reasons (I haven’t listed them because I don’t believe they matter. I believe all my colleagues are entitled to kindness and respect in the workplace, but that it’s my sole decision which ones, if any, get let into my wider life, and in whose wider lives I will participate). In the face of her advances, I have reacted coolly. Recently, when our office was empty, Helena trapped me in my cubicle and confronted me about my behavior, saying [paraphrases ahead]: “I try to engage with you, and you give me nothing back. I want us to be friends, and I don’t like seeing you be more relaxed with other colleagues than you are with me. You know I have a history of bad blood and drama with Cosima, yet you’re better friends with her than me: I don’t understand why. Is there something offensive about the way I talk to you? Why don’t you want to be my friend?”

I was very uncomfortable, but I told her the truth, or at least most of it: “This is my personality and how I’ve reacted to you is part of that. I always focus on my professional relationships first and let friendships grow naturally out of that.” I did not want to say any version of “I don’t want to be friends with you, just colleagues” because we are in a field where Helena and I will have intersecting careers until one of us moves to a dramatically different metro area. I need to maintain a positive relationship with her professionally, and I sensed that if she heard “I don’t want to be friends, just colleagues” then the bad blood she has with Cosima would be the same story she’d have about me.

At the end of this confrontation, Helena asked if we could “just start over” and I agreed. Since then, her behavior hasn’t changed at all. She interrupts my work to make friendly overtures, she pays me compliments – not just on normal things, like a new piece of jewelry or an outfit, but on my face or body – and during conversations she overshares about her personal life. She is also imposing herself on my work projects when I haven’t asked for help, despite my telling her that her assistance isn’t needed. Our manager is non-confrontational and has been ineffective at curbing Helena’s behavior, even though I’m not the only one who has been bothered by her (especially by the way she interrupts others during their workflow). I’ve been trying to save Helena’s feelings by treating her more warmly, but still without opening up my personal life to her or encouraging her to spend even more time interrupting my work. My question is: how should I behave toward Helena from now on? How much should I involve my manager in my concerns? And what should I have done differently up to now so that I can learn from whatever mistakes I made?


Dear Sarah,

First of all, A++ pseudonym usage. I can see why Helena wants to be BFFs—you like Orphan Black! And you read The Toast, so obviously you have incredible taste.

Okay, reciprocal flattery aside, I think you basically have the inverse problem as the first letter-writer. While her issue needs to be addressed via a frank conversation, I think your situation has already been talked through enough. If anything, it’s been talked through too much.

Here’s the thing: some people just aren’t meant to be friends. And some people don’t realize that they’re not meant to be friends with certain other people. I’ve been in your position before, where I start to establish a rapport with a coworker only to realize “yikes, we need to dial this thing back into colleague territory”; I’ve also been in a version of Helena’s position, where my efforts to become buddies with someone are clearly being rebuffed. It hurts to feel rejected, but putting someone on the spot with any version of “why don’t you like me?” is a bad way to handle it. It’s like asking a partner to explain—really explain—why they’re breaking up with you: any useful intel you’ll get out of it won’t be worth the salt you’re pouring into your own open wound.

Obviously Helena didn’t write to me, you did; but if I were giving her advice I’d say she needs to just let things lie. And my advice to you is largely the same, just from the other side.

You’ve already been handling this well: maintaining appropriately cordial relations with Helena while sticking to your own professional boundaries. I’d keep treating her the same way you have been—don’t spend too much mental energy on achieving perfect friendliness parity across all your coworker interactions, but continue trying to avoid doing anything that she might perceive as a slight (and thus, an excuse to dredge up more drama).

I’m hoping for your sake and hers that the “why don’t you like me” interrogations are over, but if she raises that issue again, try to deflect and disengage. “Helena, I don’t know how to answer that—I appreciate you as a colleague but I try to keep my personal life separate from my professional life.” If she presses this issue and points to your apparent closeness with another coworker: “There’s a long history there that I don’t want to get into, but in any event Alison is the exception not the rule.” (And if she brings up this “bad blood” that makes your relationship with Cosima feel like a betrayal: “Whatever happened between you and Cosima is between you and Cosima; I don’t consider it any of my business and I refuse to get in the middle of it.”)

This approach extends to all your future interactions with her from now on—the goal here is a breezy tone that nevertheless shuts down further interaction. If she starts getting too chatty, end the conversation: “I’m really busy with this project and talking about personal stuff is a distraction.” If she tries to make plans to get together outside of work: “My schedule is ridiculously hectic right now, but I’ll get back to you whenever it seems like I might be free to hang out” (which, of course, can conveniently never happen). If she says something about your appearance that makes you uncomfortable: “Can we please not discuss my face/body? That doesn’t really feel work-appropriate.”

If “bad blood” is the end result of all this, so be it—it doesn’t sound like she’s in a position to totally destroy your career, and people can coexist in the same professional circles even if they don’t get along. Staying determinedly pleasant, but reserved, will ensure that you’re not dragged down to her level.

As for your question about involving your manager, I would say handle this yourself; it’s basically a personal issue that just happens to be playing out in a workplace. (After all, what would your manager even do—tell Helena, “stop trying to be friends with Sarah”? It just seems like any intervention would only make things worse by making Helena feel even more isolated.)

However, the “Helena inserting herself into projects” thing actually is a work issue. I’d start raising this with your manager (if you haven’t already), but only in terms of its effect on your productivity. Since your boss is nonconfrontational, you can eventually build up to requesting permission to police your own time: “So since we’re in agreement that I’m handling the Dyad project, should I tell Helena that I don’t need her input?” And so on, and so on—your other coworkers will probably start following your lead, and the problem will eventually correct itself.

In an ideal world, she’ll eventually move on from her current quest to befriend you. In a less ideal world, she’ll still be somewhat of an irritant for as long as you work together, but you’ll reach a symbiosis where you’re not constantly worrying about what new conflict she’ll introduce into your workday.


P.S. To “Helena,” or anyone who’s reading this and cringing in recognition: I just want to reiterate that we’ve all been there (or, at least, I’ve certainly been there, and inevitably will be again). One person’s disinterest in pursuing a friendship is not a referendum on your worth as a person or your inherent likability; it just means you + that person ≠ friends. We’re all a little bit like cilantro—some people are like “yesss, this makes everything better” when we’re around, and others are like “nooo, why’d you ruin this otherwise good thing.” The sooner you move on to establishing connections with people who truly appreciate you, the happier you’ll be in the long run.

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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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