Uncanny Valley

by Anna Wiener

  People spilled out onto the sidewalk to smoke. I took a break from dancing and found Ian sitting alone, savoring his dessert. “This is one of the most memorable meals I’ve ever had in my life,” he said, scraping his spoon along the edge of the plate. Desserts had been placed carefully in front of every setting, and they sat uneaten, discarded. I felt grateful for Ian, and ashamed. I had slipped so easily into a smug sense of belonging. I’d been so busy eating, drinking, performing my entitlement, that I hadn’t even tasted the food.

  * * *

  As winter rolled on, it should have rained. Eventually, it did, if just barely. At the analytics startup, people had been hoping for a downpour, even though the city fell apart in the face of inclement weather: public transportation slowed or stopped altogether, and people behaved as if it were a holiday, sleeping in and arriving late, signing in to work from their apartments. Standing around in the kitchen, waiting for our sneakers to dry, someone would remark upon the bad traffic, or how long the bus had taken. “But,” someone else would inevitably, dutifully counter, in acknowledgment of global warming and statewide drought, “we need it. We need it.”

  I had silently hoped the drought would keep up. Rain in San Francisco meant snow in Tahoe, which meant the annual ski trip was a go. Much as I liked most of my coworkers, I was wary about weekending with them—not to mention the higher-ups. It seemed like more of a liability than a perk: there was so much potential to introduce new and uncomfortable dynamics into workplace relationships. I didn’t really want to know what everyone looked like when they first woke up, or hear an engineering manager grunting in the bathroom. I didn’t want to listen to chipper colleagues make the same joke about not being a morning person; I was not a morning person. I pictured myself falling on the slopes and needing help, or getting stuck on a chairlift and being forced to make small talk as our noses ran. There was too much space to demonstrate vulnerability, personhood.

  I also resented that it seemed as if we had no choice: it was not DFTC to skip out on the off-site. This made it feel like mandatory vacation, mandatory fun. Though it was a reward, a treat, the company trip was scheduled for a three-day holiday weekend, what others in the workforce might have considered personal time.

  We gathered in the office at seven in the morning, carrying paper cups of coffee and winter coats. The operations manager distributed lift tickets and ski-rental vouchers, and read out the car assignments. The cars belonged to employees who had volunteered to drive, but the management team wanted to encourage back-seat cross-pollination. We stuck to our seating assignments. We were meant to bond, so we would bond. The trip was free.

  The caravan quickly split up. Our group stopped at a strip mall for bacon, eggs, and bread, sacks of crinkle-cut chips, thirty-racks of light beer and handles of dark liquor. We were on our own for most meals, except for a symbolic dinner on the final night that was intended to pay tribute to the startup’s humble roots: the CEO and the technical cofounder would personally cook the entire company spaghetti and garlic bread, just like the lean times. Rolling a cart through the aisles, tossing in sugary cereal and protein bars, I had the distinct feeling of being on vacation with someone else’s family.

  The startup had booked a row of condominiums at a resort in South Tahoe, up against the lake. The rustic apartments were comfortably generic, with wood-paneled walls, permanently damp carpets, mismatched silverware, and assorted, cheery Americana. Despite the family-friendliness, however, we lacked the natural ease of blood relatives choosing to vacation together. The housing groups had been preassigned, without employee consultation. I liked some of my coworkers better than others, but was largely indifferent to the sleeping arrangements. There was one person I hoped not to bunk with: several weeks prior, I had split a cab with one of the men from the Solutions team, en route to our mutual neighborhood after a late night spent drinking at work. During the ride, his hand had slipped up the back of my shirt, and, when I shoved it away, down the waistband of my pants. I kept the conversation going, pushing his hands away, sliding toward the window. We hadn’t talked about it since, and I hadn’t mentioned it—there wasn’t anything, or anyone, to tell. I considered him a friend. Still, I was glad to find that the bedroom door locked.

  The first evening, I wandered the grounds with Kyle, a willowy front-end developer who had been Noah’s referral. He was modest and wildly talented, and rumored to have had a windfall after being an early employee at a gaming company that made a viral farming simulator. Kyle was one of the most serene people I had ever met—I felt I was extending my life expectancy just by being around him—and in his spare time, he made spacey, beautiful video games that weren’t designed for virality. In the office, we played pranks on each other, exchanged cryptic cartoons on sticky notes, built word ladders in the company chat room. We biked to and from work in tandem. I was sure that we were annoying to our coworkers, but I didn’t care; it felt good to have a buddy, a source of comfort and delight.

  We smoked a tiny joint, skipped stones, and walked down the beach, peering into the windows of an adjacent resort. We passed the hot tub, where the salespeople were drinking from plastic cups. I could hear the solutions manager asking the doctor about his tattoos, which spread across his chest and arms. I knew, watching them bob in the jets, how badly the doctor wanted whatever marginal leadership role I held on Support. I knew that he would get it.

  At happy hour, we all convened in one of the condos, where an assembly line of account managers was busy preparing pigs in blankets. EDM played over an elaborately rigged stereo; later, people would dance on the couches, throw themselves across the room, and pull down a quilted American flag that hung patriotically from the beams. I sat down at a long table with the solutions manager, who had brought up a bag of board games and was immersed in a heated round of Scrabble with the doctor.

  The CEO came in and announced that he was flipping the script: to allow the support team some leisure time, the engineers were to do our job instead. We’d spent the morning on the road and the day on the mountain, and the queue of customer tickets stretched out for hours. Already, most of us were drinking. Some had been drinking all afternoon. Though it wasn’t clear if we were working as we partied or partying as we worked, the scene in the condo was one of good-natured frustration as the engineers struggled to explain their own product to our users. The boys on my team mocked the engineers, rolling their eyes and leaning over their keyboards to correct them. At the time, this division of labor was a gleeful respite, a reversal of the power structure. Later, however, I realized the implication: our job was so easy, anyone could do it. They could even do it drunk.

  Business was a way for men to talk about their feelings. The internet was choked with blindly ambitious and professionally inexperienced men giving each other anecdote-based instruction and bullet-point advice. 10 Essential Startup Lessons You Won’t Learn in School. 10 Things Every Successful Entrepreneur Knows. 5 Ways to Stay Humble. Why the Market Always Wins. Why the Customer Is Never Right. How to Deal with Failure. How to Fail Better. How to Fail Up. How to Debug Your Anger. How to Build Workarounds for Your Emotions. How to A/B Test Your Kids. 18 Platitudes to Tape Above Your Computer. Raise Your Way to Emotional Acuity. How to Love Something That Doesn’t Love You Back.

  One afternoon, I wandered into a fast-food restaurant during lunch and found the CEO sitting by himself, eating a veggie burger and looking at his phone. I sat down and he slid his fries across the table. He was reading a book by one of our investors, he said. I was familiar with it. The book offered guidance on how to navigate the choppy waters of entrepreneurship and conquer the twin demons of self-doubt and external pressure. It spoke of learnings, battles, journeys. Every chapter opened with an epigraph from a rap song. The struggle was real.

  The men whom the CEO seemed to admire were the same men whom all the other men in the ecosystem admired: entrepreneurs, investors, one another. Chief among them was a founder of the seed accelerator, an English computer scien
tist who was the startup ecosystem’s closest thing to an intellectual. An aphorism generator who blogged prolifically, his rhetorical style was cool, rational, and unemotional. He pontificated, at length, on intellectual conformity. He was prone to making favorable comparisons between startup founders and great men of history: Milton, Picasso, Galileo. I didn’t doubt his business insight, but I didn’t know why he seemed to believe it qualified him as an expert on anything—everything—else.

  I had compassion for anyone who was trying to figure it out, and there was a part of me that sympathized with the CEO: though he would never admit it, he must have been in over his head. Still, I couldn’t imagine modeling my own life after that of a venture capitalist—couldn’t imagine reading a book simply because a financial middleman I’d never met had recommended it. Of course, they weren’t just figureheads to the CEO, who knew them personally.

  The book was good, the CEO told me. If you like this, you’ll love therapy, I did not say. I looked at his phone. He was on the first page of a chapter titled “Preparing to Fire an Executive.”

  “That’s a coincidence,” he said, meeting my eyes. “Don’t take it too seriously, or seriously at all.” Firing people was horrible, he told me. It was like going through a bad breakup, but worse—agonizing. I told him not to worry; it was just a book.

  I couldn’t have taken it seriously, anyway. As things were, the CEO was also the president and the chairman of the board. He oversaw Product, Engineering, Solutions, Marketing. He was the only true executive we had.

  * * *

  Noah and I met for drinks in SoMa, a few blocks from the office. The bar smelled like a deep fryer, and a fleet of motorcycles hung from the ceiling. I hadn’t seen him since he had been fired, and I was nervous: What if he blamed me? We embraced like long-separated family members.

  Noah looked happier—relieved. His Australian work boots had dirt on them. He was sleeping better, he said. He was thinking about opening a worker-owned bagel shop—cooperatives were the only ethical business model—and trying to remove the word “app” from his vocabulary. “Ap-pli-ca-tion,” Noah said, correcting himself. “The abbreviation obscures that it’s software.” This was deliberate and nefarious, reflected in the colorful, cartoonish designs of even the most technically sophisticated programs. “We’re not software!” he chirped. “We’re your friends!”

  I offered a debrief on the startup: growth was hard, revenue was flowing, Tahoe was weird, we missed him. We rehashed his firing in lurid detail. The office was starting to feel really claustrophobic and air-conditioned and sterile, he said. His job responsibilities hadn’t changed. “I thought, If I’m going to do this job forever, I’d better be rich in five years,” he said. “I wanted to get paid out. I was employee thirteen. I wanted to work there, I wanted to work hard, but I wanted to make sure at the end of it I had a significant percentage of the company.”

  I was reminded, not for the first or last time, that my stake in the company was minuscule. When I had signed the offer letter, the number of shares sounded high, but I hadn’t known to ask the size of the option pool. In a decent acquisition, I might net ten thousand dollars. I pulled on my beer, hard.

  Noah paused and looked up at the bikes, then back at me. “You could describe my position as totally unreasonable,” he said. “Or you could say what I asked for was what I needed, which was just a shitload more than what they were willing to give.”

  In any case, he said, at least his conscience was clearer. I asked what he meant.

  “Come on,” he said. “We worked at a surveillance company.” He brought up the NSA whistleblower, who was back in the media. More revelations were coming out—nearly two hundred thousand documents had been released. The surveillance apparatus was larger and more complex than originally reported, and Silicon Valley was deeply implicated. “I didn’t think about it while I was working there, because the product is so business oriented,” Noah said. “I didn’t necessarily see it as a problem for society. Plus, I don’t think I had the information that all the money from the internet comes from surveillance.”

  By surveillance, I clarified, was he just talking about ad tech? I found digital advertising annoying, but I had never thought of it as particularly malicious—though it was clear from our customer companies that free services usually meant users were being exploited in one way or another. The most straightforward way to exploit them, naturally, was through rapacious data collection.

  “I don’t see a difference between the two, functionally,” Noah said. “We facilitated the collection of the information, and we have no idea how it will be used and by whom. For all we know, we could have been one subpoena away from collaborating with intelligence agencies. If the reports are accurate, the veil between ad tech and state surveillance is very thin.”

  I didn’t know how to respond. I didn’t want to correct him. It was perhaps a symptom of my myopia, my sense of security, that I was not thinking about data collection as one of the moral quandaries of our time. For all the industry’s talk about scale, and changing the world, I was not thinking about the broader implications. I was hardly thinking about the world at all.

  * * *

  I went to the symphony with my friend Parker, a digital-rights activist I knew from New York. Parker worked for a nonprofit focused on digital civil liberties—privacy, free expression, fair use—that had been founded in the nineties by utopian technologists with a cyberlibertarian bent. It was, in a sense, the ecosystem’s anchor to history. The office was cluttered with dusty servers and outdated computers running creaky open-source software. People who really cared about technology, he had once explained to me, never used anything new. The default attitude was distrust.

  Years prior, we had conducted an off-again, on-again, casual noncommitment, which had mostly consisted of him explaining things and then apologizing. “Email is about as secure as a postcard,” he’d remind me, as we wandered between families at the farmers market in Fort Greene Park. “You don’t expect your mailman to read it, but he could.” I had listened patiently as he tried to teach me about cryptocurrencies and the promise of the blockchain, the shortcomings of two-factor authentication, the necessity of end-to-end encryption, the inevitability of data breaches.

  The romance didn’t last, but in its wake we had fallen into a rhythm of exchanging insecure emails on niche topics, like 1980s interface design, binary code, and public-domain art, and occasionally meeting for chaste, geriatric cultural activities.

  The concert hall was a quarter full. As the lights dimmed, I made a silent promise that I would spend more time and money at San Francisco’s older cultural institutions. I would participate in the civic life of the city where I lived. I would surrender my New York State driver’s license. I would look up who the mayor was.

  During intermission, we drank plastic cups of white wine and split a bag of candy. Parker was stressed about the erosion of net neutrality. He was working on a campaign to galvanize tech workers, but it wasn’t gaining traction the way he had thought it would. I knew something about net neutrality already, but I let him explain it to me anyway. Nostalgia; old times’ sake.

  The problem, he said, was that the most important issues facing the tech industry were also the most tedious. It was in their interest to fight, but founders and tech workers didn’t know how to organize. They didn’t have the patience to lobby. They didn’t consider their work political. “They all assume this will just last forever,” he said.

  We watched an elegant older couple drift by, properly dressed for a night out. I felt a little guilty for ruining their scenery. “The worst part,” Parker said, “is that the technology is getting worse every day. It’s getting less secure, less autonomous, more centralized, more surveilled. Every single tech company is pushing on one of those axes, in the wrong direction.”

  My throat felt like acid. Hey, I said, and paused. Parker looked over at me. Sugar dotted his lower lip. Do you think I work at a surveillance company? I asked.


  “What a great question,” he said. “I thought you’d never ask.”

  The startup was moving into the enterprise. We were selling to major corporations in and outside of the tech sector. We were selling to the United States government. We were becoming accountable.

  The company was growing. There was never any coffee. We stood by the machine territorially, watching it brew. The operations manager installed a surveillance camera in the kitchen, posting screenshots to the company chat room of trespasses against the commons: dirty hands stuffed into the buckets of pretzels and chips, chocolate plucked out of the trail mix, bowls of milk and cereal poured into a backed-up sink. When I slipped and projectile-spilled a bucket of granola, the footage immediately entered the company record as an animated GIF.

  The office was teeming with salespeople: well-groomed social animals with good posture and dress shoes, men who chuckled and smoothed their hair back when they couldn’t connect to our VPN. They booked up the conference rooms, annexed the server closet, took calls in the stairwell. Their desks were scattered with freebies from our customers, stickers and beer sleeves and flash drives. Their base salaries were rumored to be more than twice what the support engineers were paid. They’d chosen cash over equity and, as such, were not to be trusted.

  As early employees, we were dangerous. We had experienced an early, more autonomous, unsustainable iteration of the company. We had known it before there were rules. We knew too much about how things worked, and harbored nostalgia and affection for the way things were. We didn’t want to outgrow the company, but the company was outgrowing us. None of us had anticipated that success would be to the detriment of what made the place feel special—what made it feel like ours. The new employees treated it like any other job. The new employees had no idea.