I Am Calculating

Of the many killer lines Miranda Priestly artfully delivers in the film version of The Devil Wears Prada—putting cerulean and the economics of materiality onto the map for the rest of us—one of my favorites comes near the end. After a fluttering treat of Parisian couture, a visual sign that we’re approaching the climax of our cinematic jaunt through the pre-influencer fashion world, we find ourselves in a car watching a scene between Miranda seated next to On-dray-ah looking like she travelled 17 years into the future to play an actress called Anne Hathaway.

“You can see beyond what people want, and what they need and you can choose for yourself,” Miranda says. It’s her second best attempt at a compliment after calling size 6 Andy the “smart, fat girl”.

In the 2020 pandemic-era Netflix breakout drama, The Gambit, I see an iteration of Miranda Priestly in the main character, Beth Harmon, a chess prodigy who plays her way to the top.

When I first rebooted my career as a writer a year and a half ago after spending over a decade toiling around as a multitude of things but never one thing long enough to ever call it my “career”, I thought about how best to sell my services.

I found myself channeling that quote, thinking about what people want, what they need, but ultimately wanting to present myself in a way that feels right for me.

I considered all the possibilities. What do the people I work with, the people who hire writers—founders, CEOs, marketing managers—what do they want? And what do they need?

The word that kept coming up again and again for me was “strategic”.

Writing was a field I never really aimed to get into until it practically pounded down my door. It seemed to me incredibly over-saturated and under-paid, and I, without any formal education in writing or English, felt already disadvantaged. But those many years I held out writing solely for myself—sometimes a lot and sometimes years nothing at all—became my advantage. Among the couple of things that helps me stand out as a writer, one of them is this ability to think beyond the words, to be more than just clever with them but to think in the context of business, people, culture. It helps that I read a ton, watch a lot of television, and like to shop but mostly not buy. Part of it is my training and background as a designer (fashion). I still very much so think of things in broader strokes: concepts, collections, moods, the goal of what’s being expressed. And then, another part are the many years I spent in the trenches of entrepreneurship not just on my own but alongside others and in support of them. I don’t write to make things sound nice. I write to build things, make things happen, have the words count. All of that boils down, in essence, to strategy.

It’s a word that I have a love/hate relationship with. I’d been in meetings where “We need a strategy!” was thrown around like a hot potato until I started to zone out and the word suddenly seemed strange, surreal, like when you’re watching a movie and suddenly notice the language isn’t English anymore but you’re not sure when that happened.

Between those meetings about needing to have a strategy! strategy! strategy!, I was usually busy working, testing, iterating, intuiting it before it could be neatly presented in a shiny strategy deck. Not because I didn’t care about strategy, but because it’s much too easy to declare it and so much harder to understand if it’s the right one or to pivot when you’re wrong. You learn what the right strategy is by doing. And besides, I’d had enough experience to know that at the end of all that hot potato throwing, there was usually still no strategy. Might as well get paid to do something useful in the meantime.

If you’ve been “doing” long enough and have the mind to be able to understand the patterns and the direction of the current of the world, you could be just as strategic as any guy throwing hot potatoes around who’s sitting like a duck, meanwhile calling himself a “strategic xyz”.

Oh, hey! You’re not here for business advice, are you? What newsletter did you sign up for, anyway? What are you here for, do you even know? I’m not sure I do. I’ve been absent from free-form essays for that exact frame of time, 1.5 years, during which I’ve been in the process of building my one hundredth (or something close to it) career.

It took me a while to land on how I communicate what I do. I learned by doing. Spoiler: I’ve since dropped the word “strategic”, though I was so close to using “strategic and creative” which together, is just chef’s kiss for my kind of clients. It was also, I thought, very accurate to my process and point of differentiation.

But, sometimes the best approach isn’t to tell but to show. I could show them that strategy isn’t me saying I’m strategic. It’s the way I use words to pull them through an experience, it’s the way I consider who they are, it’s what I choose to show and tell, the order in which I tell it.

There was another reason. I don’t like the word. It used to be neutral to me before it became a hot-honey kind of word anytime I was talking to someone who makes business decisions. Oh good, you get it. Yes, strategy. We need that. Not anymore. I’d become annoyed by the default associations we have with strategy being male-oriented, even when, in my experience, men are not more or less strategic than women, just perhaps more vocal about it. And certainly more celebrated for it.

I remember in 2016, when Donald Trump won the U.S. presidential election over Hillary Clinton. I’m not ingrained enough in American politics as a non-American to fully grasp everything that led up to the decision to vote a reality television star, a business man with a business man daddy, and cultural caricature into office over a seasoned politician, but you know, I kind of get it: fresh perspectives. And maybe there was a limit to how much progress a nation can take; after its first Black president, could they go for a two-for by voting in its first woman president too? Apparently not. I know, I’m being over simplistic. I’m sure there are many valid reasons. Not necessarily right, but valid. Fair enough.

What I didn’t get were the reasons people gave for why they disliked Hillary. They were veiled discrimination—a fairly sheer veil, I might add. “There’s something I don’t like about her.” “She’s a liar.” “I don’t know. I just don’t have a good feeling about her.”

Oh, and my favourite: “She’s calculating.”

Alright. Fair enough. You can’t help who you like and as it turns out, you just don’t like this very particular personality trait of hers. Can we fault people for that? Can we fault people for a personality preference?

Not if you apply any sort of lens of reason to it.

When they’d point out reasons and cases in which Hillary has lied, of which there was evidence, to be fair, it was as if they were blindly ignorant of all the missteps Donald has made himself, of which there were many (that we know of). When faced with this fact, they’d respond with something along the lines of “Yeah but we all know that about Trump. He’s honest. Hillary’s calculating.” They were afraid of what it meant that they had assessed that there were potentially many other things going on in that brain of hers. They did not even have to be terrible things or great secrets; the fact that she felt “inauthentic”, which is what we tend to place as the opposite of calculating, was in itself the greatest misstep she could make.

It’s the double-standard that, through all our progress, just won’t go away. Taylor Swift made reference to this around the same time in her 2015 interview with GQ magazine, in which she responded to all the critics who called her out for the whole Kanye-telephone-call debacle. I admit to not knowing a lot about the mechanics of ultra-fame, but surely, Taylor, a world-famous pop star did not get to where she is by accident; somehow, that turned that into a narrative that she had to be asked to be excluded from. (Which did not work.) (Karma came not swiftly enough, many years later in 2022, when Taylor had a great year and Kanye a not-so-great one, as evidenced by all the /r/Kanye super fans declaring their newfound adoration for their former sworn enemy.)

In that interview, Taylor said:

“A man does something, it’s strategic. A woman does the same, it’s calculating.”

(To add to that, if it’s a man, he’s a visionary. If it’s a woman, she’s I-don’t-know? Women aren’t really described in this way.)

It seemed, out of all the things the press and public called her, calculating was the one she took the most offence to. That all this innocence was feigned, that her kindness was fake, that her surprise any time she won an award was a face she was putting on. Fake, fake, fake. Never mind that we as a society are built entirely off the whole concept of artifice. Never mind that we have entire social media machines now built to capitalize on the appearance of authenticity. Never mind that entire industries are obliterating and/or evolving because we can no longer tell real from fake, and that’s by design.

I thought about it when all the tech layoffs happened recently. They probably positioned it as a “strategic business decision”, not a calculated one because the latter implies a sense of coldness, one head out of thousands that, on some spreadsheet line, showed up red instead of green on ROI. On the cutting floor they go.

Because: strategy is good, calculating is bad. They actually mean the same thing; the only difference is their connotations, that being calculating is inclusive of manipulating, undercutting others, being self-serving.

And if that’s the case, those layoff memos really should’ve said “calculated business decision”. Did they?

Last September, I was sitting at my sister’s house getting my makeup done for something she was planning for her wedding. I was introduced to her wedding videographer, who asked what I do for a living. He probably wanted to know why I was available on a random Thursday morning when the rest of the world was working. I told him that I was a writer, and then he asked if I studied English in school. I said no, and then he said was that I must be a risk-taker.

I chuckled. “I’m not.” Really, I’m not. Why would it be a risk to do something that pays me well, that makes me happy, that I’m good at? (This was, I should point out, just before AI made waves for hordes of nervous writers late last year.)

I’ve accidentally been many things in my life, pulled at the whims of whatever needs my employers had—promotions, sales goals, Photoshop skills—but becoming a writer was something, finally!, that I had planned. I had saved a two year emergency fund at that point, had proof of concept, really enjoy writing and had been doing it for many many years in the context of both pleasure and business. Me, becoming a doctor? That’s risky business. Even me being a middle manager, that was pretty risky. I really asked my manager at the time, “Are you sure? Me?”. But me, as a writer? Fairly low risk.

So I said, “No, I’m just calculating.” My sister confirmed this to be the case.

After thinking about all the pieces of my life and my career, it, out of everything else, just made the most sense. It wasn’t my long-held passion or the one single idea that wouldn’t leave me alone, nor was it a coldly thought through plan devoid of any connection to who I am (looking at all the wannabe copywriters who don’t even like writing looking to make a quick and easy buck; P.S. good luck while ChatGPT gets its cold, friendly fingers in everything). It was the best thing to do in that moment, the thing that felt both financially viable and expansive. I needed whatever I did going forward to be expansive. I had miscalculated so many times, not realizing that I needed a vocation that could evolve and grow with me. But I learned eventually; a calculation is something you constantly have to recalibrate for accuracy, and sometimes you may not even know enough parts to make the sum—and in that case, you can always try some good old fashioned reverse engineering.

Mind you, this was not my first time telling people that I am calculating, using that exact word and not strategic. I also told this to a coworker once, and later on, he told me I was scary (in jest). To be fair and clear, they could be totally unrelated events. But when I tell you that, you might now feel like you have a better picture in your mind of what I’m like in person, that perhaps you’ve been reading me online and that in person, I might actually be perhaps a little scary.

But, in person, I’ve been described as “soft”, occasionally “immature” and my own least favourite, “nice”. Part of this is I’m sure the burden of expectation. I am not sure I am actually soft, just that I present that way. I wonder how many other things I am that I’ve been trained not to be.

If I’m scary in any sort of way, it’s not in a way where you need to be concerned about your wellbeing or health or sanity around me (though I am known for jumping out from behind walls to greet you when you get home, nothing anyone who doesn’t live with me should worry about)—just that what you come in expecting and perhaps wanting is not what you get. And that I suppose, scares people. Especially men who for so long think they understood not who a woman is, but what she should be.

And women, IMO, are natural calculators, as much as they’ve been shoved into the box of non-reason, void of logic, caring and loving but not rational and certainly not strategic.

Consider that war and survival were the primary pre-occupations of society for the vast majority of our history. In war, where men have a natural physical advantage, men are the fighters and the leaders. Notable exceptions: Zheng Yi Sao, the woman who commandeered over 70,000 pirates compared to Blackbeard’s 300, and Joan of Arc, who before she was a saint was a military leader known for her sieges so aggressive many villages would surrender when they heard word that she was coming.

By association and proximity, men naturally became the “strategic” ones, and women the other. The tools women use to achieve the results of their desires: relics of witchcraft, superficial, fanciful. Fluffy. The tools men use: weapons, technology, machines. Useful.

And now that the war is played on the battlefield of the modern media, the resource they’re fighting for, our attention, we’ve swapped out our military and war leaders to exalt the man of corporate strategy, the business visionary, the guy who knows what he’s doing. The man with a plan—but not too much planning, not like a party planner or a wedding planner. No, he’s strategic. Insert sparkly emoji.

A woman is allowed to be smart, sure. Come on, we’re not barbarians. She’s allowed to be smarter than a man, even. She’s even allowed to be a better leader (which is apparently, statistically true), though she’s less likely to be seen that way. Sheryl Sandberg’s Lean In, a modern leadership tome, was first praised and then blasted in a manner I’ve never seen any leadership book written by a man has. In fact, the lifespan of business books written by women seems to be inordinately short, as is the public sentiment of CEOs and founders who are women. There are so few examples of women in business, and we sure do love to tear them up. (Not that they should be immune to criticism, but what about the disproportionately large number of men running the world today who never make the news? I suppose they’re way too strategic to let a PR mishap happen, a lesson women haven’t had the time to learn yet.)

A woman can be and do anything—including yay, as of 1964 in the U.S., we can now get a bank account all by ourselves, isn't that great?—but she’s still not allowed to display any signs of a strategic mind. Her successes are not to be earned through careful design and masterminding. They’re bestowed through privilege or genetics or the luck of fairy dust—and these are twisted in a positive or negative light depending on what the story is. The only exception to this case is the strategy of man-getting*, of which people are more than happy to assign blame to the woman. See: the gold-digger. Or no, hold on. There’s also the villain. See: any evil witch archetype. See again: Miranda Priestly.

*In my anecdotal experience, men seem to me to be the calculating ones when it comes to relationships, perhaps an internet-age survival mechanism brought on by the unfavourable odds of online dating. Given the statistics that single men fare far worse than married men or single women in life, I’d say they’d better get at making a better plan, starting perhaps with recalculating their assumptions.

Let’s go back to The Devil Wears Prada for a moment. At the beginning of the film, Andy astutely points out in a frantic half-monologue that Miranda is only seen as cutthroat because she’s a woman. She would not be the villain and there would not be a story if Miranda were a Mike. That would just be business as usual. It’s only a story because we can’t conceive of the idea of a woman calling the shots and what might actually take, what kind of detachment is necessary to sustain that kind of career over decades in a cutthroat industry. And this is from someone who was already born with the upper hand; her father was prominent publisher in the UK. Of course, I’m talking about Anna Wintour, the Vogue Editor turned Chief Content Officer whom Miranda is based on. I can’t imagine what it must be like for anyone else. No wonder there are hardly any examples.

In the quest for gender equality, women are now featured in more tales than ever as the hero. Even then, she’s more likely to have things happen to her, be the damsel in distress, just an updated 21st century version. She’s not looking for someone to save her but perhaps this time to save herself from the terrible world she’s in, rather than be the one shaping the world around her using the resources she has not to win any sort of war but to build something worth fighting for. A common character arc now is the damsel turned villain trope, a turn of the plot that happens when our heroine in fact, does become calculating. When she does, she starts dressing in black, donning eyeliner and spiky things, and changes her entire personality.

A notable exception: Elle Woods, who still yet, calculates at first to get a man, but who by the end of her arc, calculates to get what she wants. Who keeps who she is, turns the world around her pink and sparkly and snappy.

Still, Elle is widely accepted because she’s palatable. That’s what most calculating women have trained themselves to be lest they be labelled a villain.

Politics aside, when I think about it, I feel like a woman who is as equally a bumbler as Donald Trump would have been more likely to have won against him. Or who knows, maybe not. There’s no way she’d be accepted as a smart and strategic, no matter how many degrees, PhDs, achievements she has under her belt. Perhaps this is the pipeline problem; we’re set up to want women to be one way, and our leaders another.

Entertainment and politics are tough to pull examples from, because we want to tell stories that matter, we want the to make the right choices in who runs our countries. But we also want our stories to sell, our leaders to be likeable. There’s a tension there. Good thing we have plenty of real-life calculators to use as examples.

Cue computers. No, not that thing you’re reading this on. The original computers, women (and actually, many people of colour) who were hired as the cheaper alternative to educated men to carry out calculations for science, astronomy, and navigation. In fact, the word computer comes from the name for these women. There goes the misconception that computing is for boys and humanities is for girls. They were really good at it, by the way, many accounts stating that women were much better at this work that involved great mental endurance, patience, attention to detail, and advanced mathematics skill.

Cue Ada Lovelace, the world’s first computer programmer (born in 1815, by the way), who invented what’s known as the world’s first algorithm based on an early prototype by her friend, mathematician and inventor Charles Babbage. Ada’s calculations were so well thought-out that they were noted as being much more advanced than what Babbage himself or any of his assistants could come up with. She was the first person to imagine and design calculations that would accurately predict the power and capabilities of computers more than a century later beyond simple mathematic equations.

Cue NASA’s computers, women like Barbara Canright who had to calculate complex equations by hand. The team, entirely female, became known as “rocket women”.

Cue Dr. Grace Hopper, who solved an equation for the Manhattan Project and said this about programming: it’s “like planning a dinner.”

The history of computing is held in the hands, and minds, of women.

Cue all the moms who are playing a constantly evolving game of motherhood filled with an ever delicate balance of things to do, who have always been the caretakers and now have the added responsibility of managing a second life at work. And if they aren’t as strategic as the man next to them who gets to “babysit” his own kids, I wonder why.

Cue all the women who run things behind the scenes, and always have, the mastermind to the frontman.

I once looked at my mom, who went to law school but told me that she had no desire or ambition to be a lawyer and just wanted to be a mom. She did just that, and I thought to myself as a kid: she wasted her mind. She ended up having to go back to work out of necessity and made her career teaching immigrants and teenagers how to drive in her late forties. She only retired nearing 70 because of the pandemic. As I’m now almost the same age she was when she had me, I see how difficult it must’ve been to raise four kids, how much she must’ve missed and sacrificed just to be my mom, how challenging and impossible it may have seemed to her to be anything other than what she was: absolutely non-calculating and just trying to do her best. What a privilege it is for me that, a generation later and born on a different continent, I have the time and space to be calculating.

Cue one of the biggest moments for women in recent pop culture history wrapped up in a song, in a medium that’s ultimately about entertainment but filtered through a real person rather than a character on a screen, a person who has dealt with what all of this means and understands it all too well.

The very important and telling closer on Taylor Swift’s latest album, Midnights, is a track called Mastermind, during which Taylor sings:

What if I told you none of it was accidental
And the first night that you saw me, nothing was gonna stop me?
I laid the groundwork and then, just like clockwork
The dominoes cascaded in a line

She writes it through the lens of a relationship—like most pop music that wants listeners—but I don’t doubt for a second that Taylor is talking about life and work too.

Not surprisingly in the least, a review from The New York Times, by Jon Caramanica, called the track Taylor’s “villain origin story”.

That anyone would think that where Taylor is at is the product of luck, privilege, talent, and hard work is laughable but not surprising. They always add that last part of hard work as if not to diminish her accomplishments. But hard work is not enough. Best believe she has a plan, that she’s playing a game, that she’s calling the shots. Where she is, and where so many women who are successful and effective, is not because they were plucked out of the ether to be stars and then simply worked hard and played nice.

Sure, I believe all the women who say, “Oh, I’m not calculating at all.” I just finished watching the Pamela Anderson documentary. She says exactly this near the end of the film, just as I’m finishing up a round of edits on this essay so that you may bask in the discomfort of being on the receiving end of my “Calculating”.

I used to be one of them before I saw with clearer eyes, how the world really worked and just how poorly we’ve been hyping up women. I believe some people just have that X factor. But how long can an X factor last when everyone around you is making the calculations and calling the shots, often without your knowledge? How long until you figure out they will spit you out the moment they can? And how many times has this already happened not just to women in entertainment, but to all women, for us to get that not being calculating isn’t something to be proud of?

Being calculating isn’t a character flaw; it’s not even a personality trait, an inherent quality. It’s not about mental ability or intelligence: From childhood we are used to women outperforming men in school. We see it as non-existent and if not that, then supremely undesirable in women because of the dissonance from the image people have of women to be of service to others (their partners, their children, their bosses, their teams, etc.) It's against their self interest to have a woman think and act in hers. Being calculating isn’t necessarily self-serving (the association of women being calculating is), but honestly, I wouldn’t mind seeing a self-serving woman or few.

Self-serve the life you want, cottage-core or glittering romance, soccer mom fantasies or rich aunt renaissance, solo adventure or modern coven. Because serving the self seems now to be the preferable option to being served this bland mess.

Being calculating is a skill that gets sharpened over time. And most importantly, it’s not the antithesis to heart and truth and nice things; it’s just how we get from A (wherever we are now) to B (wherever we want to go).

When we push forward the narrative that to be strategic is a terrible and undesirable thing for a woman to be, we continue to let the space of decision-making be dominated by men named John (fewer women total run big corporations than men named John), and remove the agency and power that comes from being the decision-maker away from women.

As a now-writer, I have to revisit strategic vs calculating. They mean generally the same thing, but we understand them completely differently. Why is it acceptable to call men strategic and strange for a woman to be the same? Why does strategic feel so good and calculating so distasteful?

Strategic, I think, implies a set of choices. Possibility. Decision. Something one controls. Like a person.

Calculating implies a narrow set of variables within set parameters. Best chances. Probabilities. Something one is told to do. Like a machine.

And this isn’t by accident. If there’s any discomfort to being perceived as calculating, to be caught in the act of calculating, it’s by design.

Calculation used to be the sign of an intelligent and great man. When the romanticism of the twentieth century synchronized with the machine age of industrialization, that perception changed and calculation was assigned to women and people of colour as a mindless, rote task. Translation if that didn’t quite land: The men really said “We don’t want to do this anymore, it’s not cool. So who can we give this work to? How can we pay them as little as possible?”. The human computers were all brilliant pioneers in their field, but their very existence was predicated on the strategy of man. That same strategy is what also brought computer sciences back to men starting in the 1980s after being almost evenly split by gender for decades, its “mindless, rote” nature all of a sudden worth much more when men wanted to do it again (see: tech’s outrageously disproportionate salaries and male gender ratio). Translation again: If men do it, it’s worth more. If women do it, it’s worth less. When men do it, they’re “disrupting the status quo”, “changing the world”. When women do it, they’re doing a mechanical task not unlike operating a washing machine. And there’s someone else in control. Tale as old as time.

Basically, women were bestowed the adjective when its use for men became mechanical, when the act of calculation became a utility and not an intelligence.

In the book How to Stay Smart in a Smart World, Gerd Gigerenzer writes: “Even today, high-level politicians and celebrities can count on getting sympathy votes by boasting about their poor grades in math.” The irony is that boasting that in itself is a calculated statement. But it shows just how being calculating is in direct opposition to being well-liked, something women are trained for from birth, which is exactly why it feels so damning to be called calculating. And yet, a man who does so significantly increases his likelihood of wealth, and he gets to be called something different, be seen in a completely different way. (Though I can’t argue that he’s more well-liked.)

Maybe it’s time for someone else to play, calculate for a different kind of endgame, to show them, not just tell them, what her mind can do.

She’ll do it even better than you, dressed to the nines while she’s at it. Because sometimes we have to look them right in the eye and play pretend, fluff ourselves up so they don’t know what’s coming.

A few weeks ago, I went thrifting and found the coolest silk blouse jacket for $8.99. It was brown and flouncy and had a chess print pattern on it.

It reminded me of Beth from The Queen’s Gambit and the way she showed up, played a game they thought was theirs, manoeuvring each piece with the steady watchful eye of a predator about to take something other than a man for its prize, like my cat catculating to see whether he can make the leap from kitchen table to forbidden top of fridge where there is nothing for him but the sheer joy of having done it.

Beth’s smirk is knowing, her mind a motion of gears calculating the odds for the thing she has chosen to want. And after she won, she said:

I didn’t play the way he thought I should.

I bought it.