Uncanny Valley

by Anna Wiener

  The thought of him awake at three in the morning, barreling down a digital highway, fiddling with the controls in a digital cab, patching through to strangers, made me wonder how he would fare in Brooklyn, around people who might appreciate or encourage his curiosity about things other than code. I still clung, condescendingly, to the conceit that art could be an existential curative. That music or literature was all anyone was ever missing. That somehow these pursuits were more genuine, more fulfilling than software. I didn’t consider that perhaps he liked his life—that he wanted it to look in no way like the one I had left.

  As we walked back to the office, I told him about my friends in New York, and how they didn’t seem to understand the appeal of working in technology. In the elevator, we joked about building an app that might interest them, one that would algorithmically suggest pairings of cocktail recipes and literature, according to a given book’s mood, era, and themes. I returned to my desk and didn’t think about it again—until the following afternoon, when the CTO messaged me in the company chat room and told me he had built it.

  * * *

  The startup hosted a monthly salon for the data curious, a catered happy hour with presentations from product managers and engineers, sourced from our customer list, about how to use analytics to run A/B tests, or growth-hack, or monitor user flows. Though I had loved going to publishing parties, where chatty editorial assistants quickly eschewed professional networking to gossip and gripe, nibble on stale pretzels and drugstore holiday cookies, and drink too much cheap wine—which always gave these evenings a coursing undercurrent of peculiar sexual energy—I had not been to tech networking events in either New York or San Francisco. I was curious, the day of my first big-data happy hour, about who would voluntarily spend their evening in someone else’s office listening to a sponsored presentation about mobile analytics.

  The event was packed. Almost all the attendees were young men in startup twinsets, branded hoodies unzipped to reveal T-shirts with the same logo. Not that I could judge—we all wore our own branded T-shirts, most of them snatched from the supply closet, creases from the folds still visible. A small team of caterers worked furiously in the kitchen, arranging platters of cheese and replenishing coolers with beer and bottles of local white wine. There was a six-pack of root beer for the solutions manager, who was Mormon. I found the root beer moving.

  The men roamed in clusters, like college freshmen during orientation week. They stood near our cloth-covered lunch tables and loaded compostable plates with charcuterie and fruit, crudités and hors d’oeuvres: lamb sliders, steamed barbecue-pork buns, tiny shrimp spring rolls. There was not a coursing undercurrent of peculiar sexual energy, or any sexual energy at all; everything was straightforward, up front. The attendees were clear about what they wanted, which was for their companies to grow. They were excited to talk about their startups, and all small talk was prelude to a pitch. I was guilty of this, too: I was proud of where I worked, and we badly needed to hire.

  Our team was penned off in a corner of the office, at a cluster of tables marked with a sign that read SOLUTIONS ZONE. I stood in the Zone and felt powerful. Because the products of our labor were intangible, meeting customers felt amazing—validating. They approached, gave us their company names, and asked for help running reports. We never asked for their corporate ID cards or any sort of validation, and none of them ever questioned why it was so easy for us to pull up their data sets. Their companies had customer-support teams, too.

  The presentation that evening was top-shelf: a fireside chat between two venture capitalists. There wasn’t an actual fire, but the VCs looked sweaty, close to pitting out. Even from the back row, the office felt moist. I’d never been in a room with so few women, so much money, and so many people champing at the bit to get a taste. It was like watching two ATMs in conversation. “I want big data on men talking about big data,” I whispered to one of the engineers, who ignored me.

  After the event, we traveled in a group to a bar around the corner. The bar was subterranean and meant to look like a speakeasy, with heavy velvet curtains, a live jazz band, and bartenders who referred to themselves as mixologists. The faux speakeasy, on the edge of a neighborhood filled with paperless offices, was newspaper themed. Newsprint that looked like it had been soaked in black tea lined the walls. Typewriters were scattered about as decorative objects.

  My coworkers looked glossy, exhausted, proud. They took shots, jostled against each other, jockeyed for the CEO’s attention. I found myself at a two-top with him, briefly, drinking something heavily garnished with mint. “I want you to eventually lead Support,” the CEO said, leaning in. “We need more women in leadership roles.” I basked in his attention. When I finished my drink, I let the ice melt, and then I drank that, too. I didn’t think to mention that if he wanted more women in leadership roles, perhaps we should start by hiring more women. I didn’t note that even if we did hire more women, there were elements of our office culture that women might find uncomfortable. Instead, I told him I would do whatever he needed.

  Later, I stood in line for the bathroom behind two women in heels and day-to-night dresses. They looked around my age, but polished—shinier. They looked like the sort of woman I had wanted, and failed, to become back in publishing: self-possessed, socially graceful, manicured. They were probably having a different kind of night. The three of us leaned against the tiled wall and pawed our devices. My inbox was full of customer emails. I tried not to look down at my untucked shirt and tennis sneakers, my hips lapping over the lip of my jeans, the name tag on my chest that read SOLUTIONS! I tried not to imagine myself in their shoes.

  When I reentered the bar, thankful for the dim light, I realized nobody else in our group had bothered to change before leaving the office, either. Like campers on a field trip, we were all still wearing our company T-shirts. I AM DATA DRIVEN, our chests announced to the world.

  Every Tuesday, at exactly noon, over a hundred synchronized sirens wailed across San Francisco, a test of the city’s emergency warning system. The sirens also signaled, at the analytics startup, that it was time for our weekly all-hands. The most obedient of us would perch on the two sofas in the middle of the office, and the rest would roll over in their desk chairs, flanking the CEO in a semicircle like children at a progressive kindergarten.

  At the start of each meeting, the operations manager distributed packets containing metrics and updates from across the company: sales numbers, new signups, deals closed. We were all privy to high-level details and minutiae, from the names and progress of job candidates to projected revenue. This panoramic view of the business meant individual contributions were noticeable; it felt good to identify and measure our impact. At the end of the meeting, the packets were gathered, and later shredded.

  The meeting’s highlight was always the CEO, who would debrief us on the financial health of the company, our product road map, his big-picture plans. As was trendy in the ecosystem, we embraced transparency. Truly important decisions were likely made in the Pentagon, or in back-channel chat rooms, but it still felt good to be included.

  We were doing well—we were always doing well. In a culture where profitability was a bragging right, we had plenty to be smug about. Our revenue graphs looked like cartoons of revenue graphs. The engineers had built an internal website where we could watch the money come in, in real time. The message was clear, and intoxicating: society valued our contributions and, by extension, us. An IPO seemed not just inevitable but imminent.

  Even so, the enemy of a successful startup was complacency. To combat this, the CEO liked to instill fear. He was not a formidable physical presence—he had gelled, spiky hair; he was slight; he often wore a green jacket indoors, presumably to fight the chill—but he could scare the hell out of us. He spoke in military terms. “We are at war,” he would say, standing in front of us with his arms crossed and his jaw tensed. Across the world, Syria and Iraq and Israel raged. We were at war with competitors, for market sha
re. We would look down at our bottles of kombucha or orange juice and nod along gravely.

  The CEO was not especially inspirational, but he was impressive. It wasn’t just that he was the most powerful person in the room—though he was, of course, always the most powerful person in the room. Everything he touched seemed to turn to gold. When he identified any one of us as having done something good, a rare occurrence, it was deeply gratifying. We were desperate to please him. We never stopped moving. We were Down for the Cause.

  Down for the Cause: the phrase was in our job listings and our internal communications. It meant putting the company first, and was the highest form of praise. The holy grail was being thanked by the CEO in person—or, better yet, in the company chat room—for being DFTC. This happened, from time to time, if one of us did something especially useful outside of our job description. If he was in the right mood. If we were lucky.

  * * *

  Camaraderie came easy. The office was big enough to keep a wide berth if we wanted one, but we stayed close. We all knew who was hungover. We all knew if someone was suffering from stress-induced IBS. We abided by what we jokingly called the ass-in-chair metric: our presence was proof. Slacking off was not an option. If someone was missing, something was wrong. Research showed little correlation between productivity and extended working hours, but the tech industry thrived on the idea of its own exceptionalism; the data did not apply to us.

  Besides, we were having fun. We were circumventing the fussiness and protocol of the corporate world: there was always an opportunity to accelerate straight into management, like skipping a grade, skipping three. We dressed however we wanted. We were forgiven our quirks. As long as we were productive, we could be ourselves.

  Work had wedged its way into our identities. We were the company; the company was us. Small failures and major successes were equally reflective of our personal inadequacies or individual brilliance. Momentum was intoxicating, as was the feeling that we were all indispensable. Whenever we saw a stranger at the gym wearing a T-shirt with our logo on it, whenever we were mentioned on social media or on a client’s blog, whenever we received a positive support ticket, we shared it in the company chat room and we felt proud, genuinely proud.

  * * *

  I began wearing flannel. I bought Australian work boots and biked to work in them, sweating. I incorporated B vitamins into my regimen and felt more awake, more cheerful. I began dipping into EDM. It was a vestige of Burning Man that never went out of season in the Bay Area, like ecstatic dance or LED-studded sculptures or psychedelic leggings.

  Listening to EDM while I worked gave me delusions of grandeur, but it kept me in a rhythm. It was the genre of my generation: the music of video games and computer effects, the music of the twenty-four-hour hustle, the music of proudly selling out. It was decadent and cheaply made, the music of ahistory, or globalization—or maybe nihilism, but fun. It made me feel like I had just railed cocaine, except happy. It made me feel like I was going somewhere.

  Was this what it felt like to hurtle through the world in a state of pure confidence, I wondered, pressing my fingers to my temples—was this what it was like to be a man? The sheer ecstasy of the drop made everything around me feel like part of a running-shoe ad or a luxury car commercial, though I couldn’t imagine driving to EDM, or even online shopping. I couldn’t imagine playing it for my parents. I would lean against my standing desk and dance while pounding out emails, nodding in solidarity with the rest of the team. My feet may as well have been turning the world.

  * * *

  My teammates were all skilled at maneuvering the RipStiks. They glided across the office, twisting and dipping with laptops in hand, taking customer calls on their personal cell phones, shuttling from desk to kitchen to conference room.

  Mastering the RipStik was a rite of passage, and I could not do it. After a few weeks of trying, I ordered a tiny skateboard off the internet, a neon green piece of plastic with four wheels that looked coolest when it wasn’t being ridden. I came into the office over the weekend to practice on the skateboard, perfecting my balance. It was fast, dangerously so. Mostly I put it under my standing desk and then got on board, rocking back and forth as I worked.

  * * *

  Our core users were programmers and data scientists, almost all of whom, by nature of the industry, were men. I grew comfortable talking to them about the technology without really understanding the technology itself. I found myself confidently discussing cookies, data mapping, the difference between server-side and client-side. Just add logic, I advised cheerfully. This meant nothing to me but generally resonated with engineers.

  Twice a week, I hosted live, instructional webinars for new customers. I shared my screen with groups of strangers and pointed-and-clicked through demo dashboards modeled after hypothetical companies’ data sets. Don’t worry, I would reassure them, riffing on a well-worn script, this is dummy data. I asked my parents to join, as if to prove that I had moved away from them to do something useful, and one morning, they did. My mother emailed after the session to offer her feedback. Keep that perky tone! she wrote, crushingly.

  The tool should have been straightforward. It was, in theory, simple enough to be used by a marketing manager. At least, that’s what my coworkers said—a blessing upon modern software. For years, the catchphrase had been So easy, your mother could use it, but this had grown uncouth and politically incorrect, to be used only in meetings where women weren’t present, of which there were plenty. But our users were endlessly creative in their ability to implement it incorrectly. They activated their own code, only to find that ours was silent, unresponsive. They checked their dashboards, refreshed and restarted their browsers. Then they would email, angrily.

  I don’t see any data, they wrote. They wanted to know: What was wrong with the software? Were our servers down? Did we know they were paying us thousands, and for nothing? They were convinced that the tool was broken; they were convinced they could not be at fault. These notes were laced with anxiety. Some customers would panic, level accusations, disparage the company on social media. There was a small part of me that relished their frustration: I knew that I would fix it. There were no unsolvable problems. Perhaps there were not even problems, only mistakes.

  My job was to reassure them that the software was not broken—to remind them that our software was never broken. Step by step, I would begin to debug their processes. Sometimes this involved looking at a customer’s source code or data, where, once inside, I could begin to untangle the errors. This was like working a pin through a snarled necklace: slow, deliberate, prone to backsliding. With quiet satisfaction, I explained to customers exactly where things had gone haywire, and then found ways to take responsibility for their errors. I reassured them that our product was complicated, though it should not have been complicated for them. I conceded that our documentation should have been clearer, even if I had just written that piece of documentation myself. I apologized, over and over, for mistakes that they had made. Does that make sense? I’d ask every few minutes, as gently as a tutor, giving them space to shift the blame back to me.

  For particularly difficult cases, we took to the telephone. We didn’t have desk phones, so I gave out my personal mobile number. In a text-based industry, speaking on the phone was surprisingly intimate. Unless the customer was verbally abusive, I liked doing it. Most understood that customer support wasn’t coming from an outsourced call center in the middle of Indiana; it was just coming from me. I would roll a desk chair into the brutally air-conditioned server room, drink tea, and repeat myself until it felt like we had come to an understanding. Sometimes a customer and I opted to video-chat and screen-share, but this felt like too much exposure, too much personhood. I was always unnerved to sign in to the meeting and see my own face floating above the pixelated head of a stranger, blinking back.

  Offline, away from the cold portals of their inboxes and our support ticketing system, customers tended to get more personal. On Sol
utions, we often spoke about how to “surprise and delight” our users—a customer-service lesson promoted by the online superstore—but sometimes our users were the ones to surprise me. They told me about their workplace conflicts; they talked about their divorces and online dates.

  One of the customers told me to look up his blog, which I did immediately, skimming his posts about vacations and strength training, as I gave him instructions over the phone on how to use our data-export API. I clarified how to format request parameters while scrolling through photographs of his ex-wife eating lobster rolls; standing akimbo on various mountains; holding their cat, who had died. A few days later, we struck up a para-professional email correspondence—about my yearning for New York and his foibles with online dating—but I backed off when it grew too intimate. We never met.

  Some days, helping men solve problems they had created for themselves, I felt like a piece of software myself, a bot: instead of being an artificial intelligence, I was an intelligent artifice, an empathetic text snippet or a warm voice, giving instructions, listening comfortingly. At the top of every email the men received, my avatar, a photo taken in Brooklyn by a close friend, smiled shyly from behind a curtain of hair.