by Anna Wiener
I felt ashamed about my own class privilege, everything I took for granted. My closest brush with manual labor was breaking down cardboard boxes in the basement of an independent bookstore. I retrieved additional seltzer waters for us, tangerine flavor. We made uneasy jokes about what a tech workers’ union would strike for: ergonomic keyboards, a more inclusive office dog policy. I couldn’t elevate the mood. Neither of us could let it go.
“People need unions to feel safe,” the engineer said. “What would a union protect any of us from? Uncomfortable conversations?”
* * *
Our remote coworkers had wants. They often spoke of feeling like second-class citizens. As the company became more corporate, the culture had gone from remote-first to remote-friendly. The startup’s early techno-utopianism did not scale—though not for lack of trying.
In an internal discussion, some of the remote employees campaigned for perks. Food and drink were supplied at the San Francisco headquarters, noted a woman who identified as a digital nomad; a snack and drink allowance for remote employees seemed only fair. I work from a coffee shop, she wrote. I have to buy something when I’m there, and I don’t even drink coffee.
HQ also had a cleaning crew, someone pointed out. Definitely wouldn’t say no to an allowance for a housekeeper, he added, in case he was being unclear.
A modest yearly budget for home office improvements would be useful, wrote an engineer. He listed items that could not be expensed: office plants; mini-fridges; wall decorations; furniture maintenance.
Flights over four hours long could be booked in business class, posted a salesperson. I would do a better job representing the company if I could nap on the flight.
Home gym equipment, someone else said. A road bike, or a good pair of running shoes—a surfboard, or skis. We could get signed up for one of those snack subscription boxes, suggested a support representative whose modesty moved me.
I’d like to see more flexibility in the fitness benefit, wrote another engineer. I’m not comfortable in gyms, so paintball makes up the majority of my physical fitness regimen. It’d be nice to use the benefit to pay for equipment, and paint.
My engineer comrade sent me a link to the thread. This is exactly what I’m talking about, he wrote. Read this, then tell me you still want to give these people any power.
* * *
A software developer I knew through mutual friends invited himself over to HQ for lunch. He had never been inside the office, he said. He was dying to see it. Working at a company beloved by engineers had given me unearned credibility; I didn’t tell him that I almost always worked from home these days, in sagging leggings.
When the developer arrived at the office, something about him seemed different. A certain swagger. He had always been well-dressed, in a machine-washable way, but he had rolled up wearing a leather jacket and aviator sunglasses. I surveilled him warily as he surveyed the rows of unoccupied standup desks. “So this is where it all happens,” he said, nodding approvingly. I had forgotten how much the open-source startup meant to people on the outside. The developer had only ever worked for large corporations, he told me: a cog in the machine. Nothing like this.
We brought lunch up to the roof deck and sat in the sun. Strings of café lights swung above double-wide deck chairs protected by a privacy barrier of palm fronds. In the pool of the apartment complex next door, a woman swam slow and elegant laps. The day inspired lethargy. I wanted to stretch out in one of the padded white lounge chairs with a novel. I wanted someone in a position of authority to remind me to apply sunscreen.
The developer and I ate soba noodles and made small talk. After half an hour or so, he folded his napkin, placed it in the takeout container, and asked, casually, whether I was familiar with a news story about a batch of documents that had been leaked by an anonymous source. It had happened months ago, but it had been in the headlines for days: the documents had exposed personal information about a spate of high-profile politicians, billionaires, and businesspeople. It was an indictment of undemocratic activity perpetrated by the very rich. Newspapers were still publishing stories about the fallout.
Of course, I said. I asked why he mentioned it.
The developer leaned back in his chair and shot me a tilted smirk. In a subtle, swift gesture, he raised his hands and pointed both thumbs at his chest.
* * *
I was furious. I didn’t know what to do with this information; I wondered if it was even true. The developer’s reason for telling me, he had explained, was that he was disappointed in the media coverage. He wanted to communicate that abuses of power could be exposed by ordinary citizens—he didn’t have an intelligence background, he just cared about structural inequality—and that most conspiracies were mundane. The things that moved history, he said, were often random and serendipitous. He wanted to find someone who would relay his story with more action—more character. He thought I might know journalists in New York who could help.
Journalists in New York told me the story had passed. Still, I couldn’t stop thinking about it. I appreciated that there were engineers who still saw the skill set as potentially subversive, in service of the greater good, and not just individually lucrative. All these people, spending their twenties and thirties in open-plan offices on the campuses of the decade’s most valuable public companies, pouring themselves bowls of free cereal from human bird feeders, crushing empty cans of fruit-tinged water, bored out of their minds but unable to walk away from the direct deposits—it was so unimaginative. There was so much potential in Silicon Valley, and so much of it just pooled around ad tech, the spillway of the internet economy.
I liked thinking that some of the programmers I passed on the street every day might also be growing disillusioned with the enterprise. That they wanted something better—more. That they intimately understood the global system to which they were contributing, and wanted to change it, and were willing to put themselves on the line. As someone who preferred aboveboard processes, it scared the shit out of me. It also inspired a feeling like excitement, or hope.
Northern California did not offer a natural human experience of the passage of time. I was confused by the abundance of postcolonial, non-native flora. I was always eating expired yogurts. I was always actively trying to recall the season. I hadn’t seen rain in three years. It was no wonder San Francisco was referred to as a city of Peter Pans; no wonder so many people tried to live in the perpetual present. It was easy to forget that anyone was getting older, or that anyone ever would.
“I’ve been living like someone in her twenties for over a decade,” a coworker observed one afternoon, as we idled around the office bar. “I’m almost forty. Why am I going to three concerts a week? Wasn’t I supposed to have children?”
A group of our coworkers were already shaking cocktails and pulling drafts. Someone had opened a bottle of pink prosecco. Two men in matching hoodies played a loose game of shuffleboard, and engineers at the Ping-Pong table dutifully ticked the ball back and forth. Through the floor-to-ceiling windows behind the DJ booth, I watched a man lying on the sidewalk, pants pulled down to midthigh, napping on his side in the sun.
“My friends back home are fighting with their spouses about mortgages,” my coworker said. She looked into the murk of her coffee cup and sighed. “What does this all look like when everyone gets older? When does this stop being fun?”
* * *
Was it still fun? Was it ever? I had turned twenty-nine that summer, and I was starting to want things I had not wanted when I was twenty-five. I developed the bad habit of swiping through real estate apps thirstily, like I was waiting for a gut-renovated Victorian in Cole Valley to ask me, unsolicited, for my Myers-Briggs type.
I began pointing to babies in the street as if I had only ever seen one in an encyclopedia. Look, I would say to Ian—a baby! Like we were bird-watching. Like I had just seen a shooting star.
* * *
To celebrate his birthday, Patrick threw a small par
ty at a campsite, technically a horse camp, near Muir Woods. Someone has kindly volunteered to help hold up the equine side of the bargain, the invitation read. Arriving in the saddle is warmly encouraged.
The following weekend, Ian and I arrived at the horse camp to find a group of computer scientists in outdoor apparel assembling, somewhat inefficiently, a trough of salad. Several slabs of salmon lay on the grill. The corrals were empty. “Ah, you know San Francisco,” said a cheerful entrepreneur in a fleece vest, when I inquired after the equine side of the bargain. “Even the horses are flaky.”
Ian fell into conversation with an engineer he admired, a designer of conceptual, experimental user interfaces. It was rare for me to hear him talk about computer science. He was so reticent when it came to his job that I easily forgot how much he loved the work, the puzzles, the magic of it. I sat on a picnic table and tried to insinuate myself into a conversation between two engineers discussing young adult literature.
I had not spent a ton of time with Patrick around other people, but I had spent enough to know I was an outlier in his social circle, which was largely composed of scientists, entrepreneurs, and technologists. I often felt embarrassed to tell this crowd that I worked in customer support, then felt angry about my embarrassment. It did not help that whenever I felt insecure, I tended to get combative, or pushy, or in over my head. I was always roping founders into debates about whether or not crowdsourced reviewing sites constituted “a literature.” I was always making unprompted arguments against privatization, picking fights.
The mood was upbeat and polite. I managed to behave myself. Conversation rose and died down. When Patrick spoke, people outside of his immediate radius fell quiet and listened, like he was an oracle. Then again, I wanted to listen, too.
The salmon came off the grill and we incorporated it into the salad, gathering around the picnic tables to eat. Halfway through dinner, another skinny man in outdoor apparel bounded onto the campsite, carrying a plastic bag. Patrick leaped up in excitement. Inside the bag, he explained, were two continuous glucose monitors with digital readers. The monitors were difficult to procure in the United States, and the readers had to be imported. We all watched as he unwrapped the package and punched a sensor into his own shoulder, wincing. I tried to exchange a meaningful look with Ian. Patrick did not have diabetes. “What?” Ian said. “Seems cool. I’d try one.”
After a while, someone brought out a small cake and a candle. We sang “Happy Birthday” while Patrick turned pink. “Well then,” he said, when the singing was over and conversation did not resume. “Shall we put out the fire?” I suggested we leave it burning. We could set up our tents, then drink whiskey and talk until it got too late or too cold. This was always my favorite part of camping: everyone swapping intimacies and confidences, leaning into the evening as time slowed. I was excited for it, eager to find common ground, see everyone relax a little bit. Patrick seemed confused.
I looked around the group. It became very clear, very quickly, that the plan had never been to camp out. Ian and I were alone in having brought a tent. Within ten minutes, the party had been disassembled and packed into paper bags, the grills scraped, the recycling sorted. People filtered out into the night in carpool configurations, carrying leftovers and coolers. Flashlight beams floated out into the road and disappeared around a curve. It wasn’t yet ten o’clock.
“I guess we have the place to ourselves,” Ian said, looking around. It suddenly seemed ridiculous that we should be camping out by ourselves in the middle of an outdoor stable in Marin. The site felt exposed, comically large. The corrals glinted. I wondered if park rangers might come through, and if so, whether we would be on the hook for a horse. Would we be fined? It was state land. Were we breaking a law? Why had I thought we were all going to sleep there, like people with nothing to do the next day? Part of me felt bad that they had other things to take care of that weekend, when my only plan was to build a fruit-fly trap. Part of me felt indignant. I didn’t want to feel ashamed about being unproductive, for wanting to drink whiskey and make up fake constellations.
We should just go back, I said. Ian shook his head—he’d had a couple of beers, and I didn’t know how to drive stick. The roads were unlit and winding. We set up the tent and brushed our teeth, stamping out our spit in the dirt, then lay in parallel sleeping bags, listening to the redwoods bend in the wind.
Though I did not want what Patrick and his friends wanted, there was still something appealing to me about the lives they had chosen. I envied their focus, their commitment, their ability to know what they wanted, and to say it out loud—the same things I always envied. They were all so accomplished, and athletic. It didn’t help that I hardly understood what most of them did, I just knew they were good at it.
At twenty-eight, Patrick had built something sophisticated and sprawling, something useful that people seemed to love. I wondered what would happen if he and his friends went on to run the industry, as it seemed they might. I also wondered what it might mean on a personal level. Our friendship already demanded a certain amount of compartmentalization, presumably from both sides. I wondered if money and status would change him; I wondered whether I would become a liability. I worried that people in his position often had no choice but to conform to certain expectations: the system they were accountable to wasn’t just powerful, it was a machine. Patrick was idealistic and independent, but it seemed that the professional demands and social mores of his structural position could eventually require that he work against himself. It was strange to see him form a public identity on social media—strange that he had followers, a fan base—and from time to time, he would endorse publications or policies or positions that surprised me. I had a hard time with this. The private person was funny, thoughtful, open-minded. But the public persona, with whom I often disagreed, had growing amplification, influence, and power.
I shared some of this with Ian, who was reading by headlamp. He shrugged, the light bobbing across the fly. “I think you’re underestimating what you might have that they don’t,” he said. You? I asked, turning on my side to face him. “That’s sweet,” he said. “But bigger than that, I think. Just something worth considering.”
* * *
It seemed to me that whatever I had, that the men of Silicon Valley did not, was exactly what I had been trying to sublimate for the past four years. Working in tech had provided an escape from the side of my personality that was emotional, impractical, ambivalent, and inconvenient—the part of me that wanted to know everyone’s feelings, that wanted to be moved, that had no apparent market value.
Eventually, I would acknowledge that these qualities weren’t actually less valuable, in noneconomic terms, than what the founders and technologists prioritized. They weren’t more valuable, either; just different. My reasons for deflecting and deferring were pragmatic—money, social affirmation, a sense of stability—but they were also personal. I still clung to the belief that I could find meaning and fulfillment in work—the result of over two decades of educational affirmation, parental encouragement, socioeconomic privilege, and generational mythology. Unlike the men, I didn’t know how to articulate what I wanted. Safer, then, to join a group that told itself, and the world, that it was superior: a hedge against uncertainty, isolation, insecurity.
These motivations were not aging well. In reality, there was nothing superior about those whom I was trying to impress. Most were smart and nice and ambitious, but so were a lot of people. The novelty was burning off; the industry’s pervasive idealism was increasingly dubious. Tech, for the most part, wasn’t progress. It was just business.
This was both a relief and a disappointment. It was also, perhaps, the root of my empathy for the young entrepreneurs of Silicon Valley. Many of them were at least a decade deep into lives they had selected for themselves as teenagers. Surely, I thought, some must have wanted to try something different, get off the ride. Surely some were beginning to have moral, spiritual, political misgivings. I was
radiant with projections.
I did think about what the endgame could look like. I saw myself pursuing success as a nontechnical woman in tech: becoming a middle manager, then an executive, then a consultant or coach who spoke at conferences, to inspire more women. I could see myself onstage, forcing a smile and holding a clicker, feeling my curls go limp in real time. I could see myself writing blog posts on my own personal business philosophy: How to Squander Opportunity. How Not to Negotiate. How to Cry in Front of Your Boss. I would work twice as hard as my male counterparts to be taken half as seriously. I would devote my time and energy to a corporation, and hope that it was reciprocal. I would make decisions based on the market that were rewarded by the market, and feel important, because I would feel right.
I liked feeling right; I loved feeling right. Unfortunately, I also wanted to feel good. I wanted to find a way, while I could, to engage with my own life.
* * *
For a long time, I harbored the belief that there was a yearning at the heart of entrepreneurial ambition, a tender dimension that no one wanted to acknowledge. Some spiritual aspect beneath the in-office yoga classes and meditation apps and selective Stoicism and circular thought-leading. How else to explain the rituals and congregations, the conferences and off-sites, the corporate revival meetings, startup fealty and fanaticism—the gospel of work, modernized and optimized? I was committed to the idea of vulnerability.
All these boys, wandering around, nimble and paranoid and prone to extremes, pushing against the world until they found the parts that would bend to them. I assumed they had people to impress, parents to please, siblings to rival, rivals to beat. I assumed their true desires were relatable: community, or intimacy, to simply be loved and understood. I knew that building systems, and getting them to work, was its own deep satisfaction—but I assumed everyone wanted more.
