Email us questions at [email protected], subject line “businesslady.” Previous installments can be found here.
Dear Businesslady,
I am deeply, frustratingly, maddeningly in love with my female boss. I am also a woman, and I identify as “mostly straight” — I have only dated men but have had two other deep, frustrating, maddening, ultimately unrequited crushes on women.
My boss is five levels above me. She is one of the heads of our company. She knows how I feel, at least in a jokey sense, because our office is small and casual, and I am kind of … endearingly open about it? That sounds like I’m a freak, but I swear I’m funny and normal. She is friendly toward me, and even affectionate. She drives me home and we talk openly about our lives. But of course she is straight, and of course this is completely unrequited.
I don’t know how to get over it, and it’s making work very hard. I take her feedback very personally. I don’t mean to, but I am crazy about her and her opinions. I can’t leave my job because I love, love, love my job. How do you get over someone you see every day, who manages you, who is the world’s most beautiful and perfect person?
Frustrated in my Cube
Dear Frustrated,
I felt like I had to answer this since it feels like an inversion of the possibly-gay-boss query I fielded in my last column. But even though I took the opportunity to give that person a pretty extensive talking-to about appropriate workplace boundaries, the answer to their question was pretty simple, and the answer to yours is too:
You can’t date your boss.
This is true even if you and your boss are both single and mutually attracted to one another, although obviously that’s a pretty tempting scenario. And, okay, theoretically relationships can flourish between employees and their superiors, and I’m sure there’s plenty of anecdata about how Sometimes It Works and Is Totally Fine—but it’s more likely to be an unmitigated disaster for everyone involved (including the lovers’ coworkers), hence the rule.
If anything, your situation is easier to navigate because there’s no “do I quit my job and go for it?” hanging out there—your boss is straight, you’re both ladies, and it’s a relationship that seems destined to remain firmly lodged in the realm of the platonic.
I realize, though, that that’s technically not what you asked—you asked how to get over this “beautiful and perfect person” who also happens to be your manager. And before I address that question, let’s move on to your other letter, sent in tandem with this one (yep, it’s a twofer today, folks):
Dear Businesslady,
I am 27, working for [a workplace; specific field redacted to protect LW’s privacy]. I don’t know if I would have asked this when I was 22, because I didn’t think about my career or its trajectory as much then. You are in your early 30s. What would you say to your 27-year-old self about the next five years, and how to make the most of them professionally? I feel very much at a turning point in my working life, when success either starts to happen for you or doesn’t. Please help.
Hi again, Frustrated,
Maybe I’m reading too much into this, or am way off base, but I can’t help but feel like this second question is related to the one above.
I’m generally of the opinion that crushes reflect a lot more on the crush-er than they do on the crush-ee, and are mostly about what you’re projecting onto the object of your affection. I can’t tell you what causes them or how to make them go away, but every crush I’ve ever had—from pseudoplatonic, to dissonant with my typical attraction matrix, to actually fixated on someone who could be a viable partner—has existed almost entirely in my own head, as opposed to being in response to actual, real-world interactions. Since you mention that this unrequited-pining thing has happened to you before, and that you identify as “mostly straight”—and especially since your current crush is focused on your superior at a job you “love, love, love”—I suspect that it’s somehow tied to your feelings about your career.
I’ll let you sit with that presumptuous speculation for a second, because I’m also intrigued by your prompt of “What advice would you give your 27-year-old self about her professional development over the next five years?”
It just so happens that my 27th year was a pretty big one for me: I was feeling stuck in my job and was trying to figure out how to handle that when I got hit with a life-threatening illness. Once I recovered, those old frustrations were sharpened by my newfound perspective of “this is your only life and it could all end in an instant.” So even though some things about my old position were comfortable and convenient —and even though I could come up with countless excuses why it was a bad time for me to make a change—I decided to start exploring other options that were more in line with my personal goals, and that eventually led me to where I am today. Looking back, I wouldn’t change a thing, except that I would’ve maybe been a little more proactive about moving myself forward.
But at 27, I was in a job that I definitely didn’t view as a career. Even now—when I’m privileged to enjoy my work a lot more than most people—I probably wouldn’t say I “love, love, love” it, like you do. You’re living the dream! Yet you’re asking me for advice?!
Here’s the thing about career trajectories: they’re kind of impossible to predict. Sure, it’s productive to put some effort into thinking about your ideal five-year plan, but unless you’re in a field where there’s a clear hierarchy of consecutive positions, it’s unlikely that things will play out the way you anticipate. And like so many things in life, if you’re happy where you are, you’re already better off than almost everyone else on the planet.
Crushes are a similarly unknowable and mysterious force, but in my experience they tend to just slowly evaporate; like a canker sore that plagues you for weeks until the day you realize that your lip feels totally fine, you might see your boss one morning and realize that she’s just My Awesome Boss and not The Woman of My Dreams, If Only. It might help to focus on things that would undermine your long-term compatibility if you did get together—annoying habits she has, or disparities in music/TV/movie taste, schedule, food preferences, etc.—but it’s also probably good for you to double down on the work aspect of your relationship.
My 27-year-old self didn’t really have a mentor figure, but it sounds like your boss is pretty much the ideal: someone who’s senior to you in a job you adore, with whom you already have a friendly rapport. During one of these chats on the ride home from work, there’ll surely be an opening for you to say, “Hey, I feel like I’m on the cusp of a turning point in my career, and I really want to make the most of the next five years.Can you just, like, sit and just mentor me for a second?” Pick her brain about how she got to where she is, compare her position with your own interests and aspirations, and see where that leads. If nothing else, you have an amazing opportunity to gain some insights about your career. And maybe—just maybe—these conversations will help reinforce your respective roles as boss/employee, ultimately butting out the love-object/unrequited-piner dynamic that’s currently bothering you.
One last thing, though, before I go. I know what you’re saying about 27 being a crucial moment where “success starts to happen or it doesn’t”—but where you are at 27, 37, 47, whatever, isn’t necessarily an indicator of your big-picture happiness or prospective life achievements. The truth is that “success” is so subjective, and so arbitrarily defined within the context of particular groups, that it’s almost a meaningless metric. I make less money now than I used to but also have more flexibility in my schedule—does that make me more successful, or less? What about people who leave behind lucrative, even gratifying jobs to pursue passions that have little (if any) monetary reward—are they failures?
If you spend your days doing something you enjoy—and have enough capital at your disposal to not feel stressed by the demands of modern living—then you’re a success, period. Considering the position you’re already in, I don’t think you have much to worry about when you look to the future, and I expect that 32-year-old you will back me up on this someday. In many ways, yearning for the official status called “successful” is a lot like having an unattainable crush: a potentially useful tool for figuring out what you want (or don’t), but also a way of distracting yourself from the real (and realistic) opportunities available to you.
You’re earning money while not hating your life: that’s a gift. But it doesn’t have to happen at your current workplace indefinitely, and maybe the angst you’re feeling about your career is a sign that you’re ready for a change. If your love-love for your boss continues to interfere with your love for your job, do your emotional health a favor and start looking for a new position. I’m sure she’ll give you a great reference as you make the switch to a new workplace, and I’m equally sure that you’ll be a lot happier once you’re no longer feeling tortured by unrequited affection.
—Businesslady
To second LW – don’t worry about ‘being at the point where succes happens or doesn’t’ – My mothers success in her self-run business didn;t really start until 50. Since then, she’s got three book contracts, dozens of article requests, a request to do the house history for a rock star mansion and started getting asked to appear on television and radio as an expert.
‘Success’ that nebulous thing, can happen at any time.
Seconded: My moher was (practically) a displaced housewife. She took some evening classes, became a success in her chosen field, eventually retired manager at the Fed. Did she “plan” it? Nope: She had “planned” to fold diapers and volunteer at church. Lifealmost *never* goes as planned. Certainly she made strategic choices, but they were all very “in the moment,” meaning they were clever reactions, not necessarily well thought out plots.
Thank you both for these anecdotes; I often get caught up in the moment with regard to my life trajectory and really appreciate hearing about cases in which success has come from humble beginnings.
Thirded: my mother spent 20 years as a housewife, then went back to school, got a degree, decided she didn’t like that field, got a Master’s in a different field, and is now enjoying a pretty rapid rise up the ladder with the government. She’s a very smart woman who worked very hard to get where she is, but it does go to show that it’s definitely possible to reach “success” at an older age through completely roundabout means.
Yeah, currently unemployed here, I frequently remind myself that my dad started his own business at 50-something and now has 5 employees. Before that he was a mechanic/handyman on a car junkyard.
Thank goodness. I’m 28, and read that 27 is when success either starts to happen for you or doesn’t, and felt the onset of despair.
I feel like Captain Awkward’s list of the type of crushes would be useful here.
Unattainable/Aspirational work crushes can be nice because give you something to look forward to (seeing the crush object) and fuel to work hard (to impress/please crush object). If the LW knows it’s never going to move forward, then the crush is mostly a good thing! There’s no real need to get over it unless, as our Businesslady says, the crush is having a detrimental effect on the LW’s “real” life (personal life or work life).
Ahhh I have never seen that list & I needed it.
I currently have a crush on a guy at work who is known to my friends as IWC (Inappropriate Work Crush) but it is definitely a Mutual crush and probably Attainable (he unabashedly checks me out & flirts with me) except for the fact that I think we both know how horribly wrong those things can go (his office is literally feet from my desk) so neither of us will do anything about it.
It’s both extremely frustrating & oddly thrilling at the same time. And I fully admit to checking my lippie much more frequently that I have ever at work because of him.
That said, we work in different depts & luckily there are no weird work dynamics that would ever come up. I can’t even imagine how terrible it’d be if we were coworkers or manager/employee.
Agree. I have a terrible unattainable work crush going on at the moment, and it just makes me more likely to show up, participate, and attempt to be impressive. Granted, the crush is not on my boss, which would make things trickier – but then again, I work in an industry that occasionally involves a lot of drinking and a lot of travel, which makes for some complications. Nothing like sharing a bed with your drunk work crush, oof.
I have Unattainable/Aspirational work crushes on one superior AND a number of peers/inferiors. Fiveish? I’m losing count. I saw one of my friends before work yesterday and she said, “WOW, you look great!” You’re goddamned right I do. I’m also pretty damn good at my job.
(lololol I think my coworkers believe I have the same level of confidence and competence in the rest of my life when in fact *camera pans to dumpster fire*)
Do people really “love, love, love” their jobs? I feel like that’s as unattainable as this crush. I like my job, I feel very fortunate to be employed in a position that allows me to use my degrees and my brain in exchange for fair compensation. That seems like a miracle that could be snatched away at any moment. But I still hate Mondays and I don’t, like, look forward to going to work. The only things I triple love are pizza and Emily Gilmore. I feel like having the expectation that I should feel the same way about my job and pizza is unrealistic, but maybe I am just not living my best life.
I love my job a pathetic, pathetic amount, but all morning I’ve just thought “I could get so much done if I didn’t have to go to work.” – like laying in bed for an extra 10 minutes because I needed to gather the mental strength to get ready for the rest of the week. I don’t think anyone LOVES having to be somewhere at a certain time, for a certain amount of time, doing projects they may or may not have chosen, but what you and I have is probably the best it gets, and what people mean when they talk about the perfect job :/
Yup, I feel this way as well. Definitely love it, definitely feel like I made the right choice and am excited about what I do. But I’ve also spent most of the day wishing I could lay on the couch and watch Gilmore Girls. Passthedamnhat: you would probably feel differently about pizza if you had to eat it every day (well, maybe not!).
Hmm, I think I should put this pizza hypothesis to the test. BRB eating only pizza in october will report back
This is something I’ve thought a lot about, especially since partnering with a person whose family members find a lot of meaning/fulfillment in their careers/jobs.
Growing up middle/lower-middle class, my parents’ jobs were just that–jobs. You went to them because they were necessary for earning money for food/shelter/ballet lessons. My folks went to college but neither was in a Career, really. My partner’s family all have advanced degrees in their chosen fields and have worked very hard to travel up the concomitant ladders. Since we’ve been together, he has encouraged me to find work that I enjoy, and I’m of two minds: yes, it would be very nice to have a fulfilling job that I loved (and it’s probably more possible than I think) but at the same time, I’m not sure I’ll ever love, love, LOVE my job, and I don’t want to set myself up for failure.
Long story short, I think it’s ok to be Peter at the end of Office Space: go to a job-place 40ish hours a week and not hate it, but find more life fulfillment in other areas, such as hobbies, relationships, faith, fitness, etc.
I’ve embraced the Office Space philosophy towards work in the last few years. It’d be great if I found a calling that paid me money, gave me good benefits, *and* fulfilled me emotionally/intellectually, but…I’m not holding my breath. My current job is pretty good, my coworkers/supervisors are kind and respectful, I feel valued as an employee and am pretty well compensated for the work and for where I live, and at 5pm I leave to go live my life and I generally don’t think about work again until it’s time to get up the next day. I sometimes feel bad, especially living in The Land of a Million Start Ups, that I’m not excited by my work or defined by it, that it’s a pretty boring job, but right now I have the mental bandwidth and actual free time to socialize, craft, cook, exercise, build a solid relationship with my fella, travel some…and that’s pretty great.
This is a great way of putting it.
I hate my job right now. But the thing is….my job is not my life. Maybe it would be if I had the ambition and drive to be in some absurdly dedicated profession, like a surgeon or a judge, but I don’t. To me, a job is just a way of financing my life. It would be nice to have a job I didn’t totally hate, and lovely to have a job where I felt valued and like a real contributor, and I do aspire to those things.
But it’s just a job. My real life is my family and my interests and what I do in my spare time. I think if you truly have a burning ambition and passion, you should definitely follow it and pursue it! But I think that most of us, in some way, are like me–it would be nice and fulfilling to have a job they enjoy, and and probably more enjoyable, but ultimately, a job is a way to finance your real life.
I am absolutely with you on this. My job pays for my life and for the things I find fulfilling and amazing and lovelovelove. My company really wants us all to love it, because it’s a giant world-eating American conglomerate bent on world domination and it wants us all to feel the same way about it as the CEO who built it from scratch. I like doing my day to day stuff, but I don’t look for my work to give me emotional fulfilment – that is what the rest of my life is for. The work is to keep a roof over my head and let me buy chinese takeaway when I want to without angsting about the cost.
Do we possibly work for the same company? 😉
If we do, don’t tell my boss how much time I spend commenting on here…
I did deliberately choose a job that I could leave behind though. I have a vocation already but unfortunately I also have expensive tastes, so I have a well paying job that gives me time and money to do my vocation as a hobby/lifestyle.
I don’t “love, love, love” my job, and I’m probably at about as close to the perfect job as I’m likely to get. I like my job! I feel perfectly ok with going in every morning and I get excited about some components of it. I feel like I am making a positive change in the world, while at the same time growing as a person! But I also spent this morning filling out expense reports and filing. All jobs have downsides, and the way I feel about people who gush about how much they “love, love, love” their job is a bit like how I feel about people who are all over Facebook about how much they love their “soul mate and best friend 4eva #soblessed” partner. I saw that in the letter and my first thought on seeing that letter was that she was trying to ignore something that’s bothering her about the job, the way a coworker of mine would repeat “I love my job, I love my job” as a mantra when the fieldwork got shitty.
I feel like that old Slate piece about the dangerous and oppressive fallacy of “Love What You Do, Do What You Love” is very relevant here. I think it’s all very tied to the American dream and the cult of the entrepreneur and I both hate it and totally still buy into it and am terrified to face up to reality without it. :(((
*ahem* I hear that sometimes relationships with a superior work out when you get drunk together and hookup and it’s the superior’s second job so he quits to “focus on his hobbies.” But, like, that’s just what I’ve heard.
Jack Donaghy: “I don’t think that’s a word.”
Yes.
Yeeeaaahh my first boss and a coworker (that we hired together!) are currently married with a kid and they’re great together, but there was a long period of minimally effective hiding followed by them being shunted to different teams so they didn’t have to work together and then he quit and eventually she quit. It was worth it in the long run, of course, but I know it was rough for a couple of years.
“But beware!” said the old witch, her eyes wide, “For if you ask a person you admire to tell you what you need to change about yourself, she will make utterances to shrivel your flesh and crush your bones. Maybe. About a 75% chance.”
Two best friends who got married this year started with her hiring him (only partly because she thought he was cute). I think it helped that they both knew he was only there for a short contract, and she had fears about how it looked to her seniors for a while when things between them got more serious. Anyway they are totally in love and adorable and a job is just a job right?
Hmm, I think I should put this pizza hypothesis to the test. BRB eating only pizza in october will report back
Thank goodness. I'm 28, and read that 27 is when success either starts to happen for you or doesn’t, and felt the onset of despair.
I’m in love with that screenshot! Lost and Delirious is criminally underrated. 🙂
“I take her feedback very personally. I don’t mean to, but I am crazy about her and her opinions.” I’m willing to bet that this is one of the first people who you’ve found that a.) is intellectually impressive and b.) validates you intellectually? That’s a heady feeling. It’s also the outgrowth of a power dynamic that means you can’t really engage in this relationship on equal terms.
Also, given the lack of detail beyond “I have only dated men,” I’m going to guess that there is not a corresponding intellectual validation going on from a romantic partner. You can have that, but it’s going to be hard to find it while you’re pouring your curiosity and hero-worship and deep thoughts and emotional energy into someone who cannot reciprocate.
This woman is feeding a part of you that is hungry. It’s good that you are awakened to that hunger now, but figure out a better place to get fed.
So I was a literature and language nerd (still am), the kind that looks up word roots. The annoying kind. So. Of course I don’t remember most of them 10 minutes after looking them up. I just go, ‘AH ha, interesting’ and move on. But! You guys. Infatuation means “Moving to or towards being made a fool of.” Yassss! I love it! Isn’t that just how it feels too.
That helped me once, mired deep in crush misery. I bookishly got out my Latin primer and my 5 dictionaries and cross-referenced (because I couldn’t afford an OED and this was before the days of http://www.etymonline.com). Basically: In – moving to or towards something. Fatuous – foolishness, stupidity. Infatuation – making an ass out of myself! Ah ha! Oh god no.
I’ve had the boss crush too. And it helps me to whisper to myself “infatuation means making a fool out of myself, which I am not going to do here, infatuation means making an ass out of my life, which will not take place.” It helps. Weird, but it helps.
Etymology FTW.