For months after the election, my friends and coworkers were not doing well. Stomachaches, insomnia, astrology. They drank too much. They took up moderate vaping. They went to meditative sound baths and considered microdosing to stave off looming depression or regain lost productivity. They appended their email salutations with phrases like “given the circumstances” and “despite the news.” Everyone engaged in deep and irresponsible magical thinking.
On the heavily moderated message board, the commentariat discussed a Marshall Plan of rationality, a new enlightenment. On social media, a sales leader at an education software company suggested crowdfunding private planes to fly over red counties and drop leaflets with facts about the travel ban, and a former executive at the analytics startup asked his connections if anyone could recommend a place to buy gold bars. Time to get good at crypto, everyone said. Those of us in or adjacent to the tech industry advised friends and family members to download encrypted communications apps. Our solution, as ever: more technology.
CEOs and venture capitalists, oh-shit patriots with fiduciary duties, extended olive branches to elected officials. Industry leaders protested in the airports, or at least posed for photographs. They advocated for more generous immigration policies, prioritizing immigrants who knew how to code.
Everyone was staying up late, anxiety-scrolling, and the advertising algorithms stayed up, too. Friends bought weighted blankets designed for people with sensory processing disorders, marketed to them on social media, and lay underneath with their arms at their sides, waiting for the oxytocin to drop. Fascist ideology and paranoid conspiracies circulated. Hoaxing and misinformation and memes, long the trappings of message-board culture, moved into the civic sphere. Trolling was a new political currency.
There was Nazi iconography in the news, and Nazi rhetoric in the Terms of Service team inbox. Our field was still new, and not unified. Depending on the company, our work was called Policy, or Community Policy, or Trust and Safety, or Community and Safety, or, simply, Safety; depending on the company, the team was six years or six months old. No one was equipped to adjudicate speech for the millions of people spending their lives online. Outside the industry, people argued about the First Amendment. Inside, we were calculating risk, determining the seriousness of threats, trying to react thoughtfully but nimbly. The nature of online abuse evolved quickly; it was always just a little out of grasp.
At a gathering of people in the field, a high-level employee of a household-name startup approached me to talk about our industry’s new burden of responsibility. We balanced paper plates covered in cheese and fruit. We passed our anxieties back and forth. My interlocutor leaned in conspiratorially. “There are no adults in the White House,” he said, with a trace of a smile. “We’re the government now.”
I thought, for a while, that everything would change. I thought that the party was over. I thought the industry was in for a reckoning, that it was the beginning of the end, that what I had experienced in San Francisco was the final stage of a prelapsarian era, the end of our generational Gold Rush, an unsustainable age of excess.
Then I left the house. There was the world, with its addicts and joggers, its fortified strollers and leather boutiques and swishing eucalyptus, everything bright and intact. Cranes swung over warehouses stuffed with new transplants. Shuttles crested the hills, riding the brakes on descent. The city and the industry, bound by the ecosystem, continued to cycle and churn.
I could have stayed in my job forever, which was how I knew it was time to go. The money and the ease of the lifestyle weren’t enough to mitigate the emotional drag of the work: the burnout, the repetition, the intermittent toxicity. The days did not feel distinct. I felt a widening emptiness, rattling around my studio every morning, rotating in my desk chair. I had the luxury, if not the courage, to do something about it.
In early 2018, I left the open-source startup. I wanted a change, and I wanted to write. My impulse, over the past few years, had been to remove myself from my own life, to watch from the periphery and try to see the vectors, the scaffolding, the systems at play. Psychologists might refer to this as dissociation; I considered it the sociological approach. It was, for me, a way out of unhappiness. It did make things more interesting.
Leaving a remote workplace was anticlimactic. On my last day, I had a sixty-second exit interview, conducted over video chat. I dropped a waving-hand emoji into the Terms of Service chat room and posted a brief farewell to the company’s internal message board. I didn’t know you worked here, wrote a colleague, in the comments. Then I sat on my bed with my laptop, watching my access to internal platforms be revoked, one by one. Every 404 error like a light going out. A whole world, zippered up—easy come, easy go.
After three and a half years, most of my employee options had vested. I was ambivalent about exercising them, despite the rumors of a pending acquisition: the stock was not cheap, and I was uncertain that it would amount to anything.
I convinced myself I had to play the game. On the ninetieth day of my ninety-day purchase window, I hand-delivered a check to HQ for the entirety of my savings account, to buy as many of my vested options as I could. As I stood in the guest entrance, waiting for the stock plan administrator to collect the paperwork, I watched my former coworkers chatting happily with one another in the on-site coffee shop and felt, wrenchingly, that leaving had been a huge mistake.
Certain unflattering truths: I had felt unassailable behind the walls of power. Society was shifting, and I felt safer inside the empire, inside the machine. It was preferable to be on the side that did the watching than on the side being watched.
Former employees of the open-source startup still hung out in a chat room, an unaffiliated alumni club where people tried to poach one another for their startups between debates over whether or not our stock options would ever be worth anything. They talked shit and traded speculative financial advice. They continued to swap photographs of their home-office setups and their octopus-cat stuffed animals. They waxed nostalgic about early employee summits, lost weekends, blowout parties in the office. That time they completed a team-building treasure hunt involving selfies with a stripper. That time they stashed acid at HQ. Their reminiscences hardened into shared mythology. Stories I knew, a shadow oral history, remained untold.
In June, news broke that the open-source startup had been purchased for seven and a half billion dollars, by the highly litigious Seattle-based conglomerate. The conglomerate had, in the nineties, attempted to stomp down the open-source software movement—but this was a new era, insisted everyone involved in the deal.
In the ex-employee chat room, people compared secondhand information about the share price; they posted celebratory photographs of themselves in octopus-cat T-shirts. TFW you wake up retired, wrote one of the early employees. Another expressed her ambivalence about the windfall. It’s like having a conflict diamond, she wrote. It’s valuable, but it came at an unforgivable human cost.
Not just a diamond, a mine. A significant fraction of my former coworkers became millionaires and multimillionaires; the founders became billionaires. The venture capitalists refueled. I was happy for friends, especially lower-level employees who had worked incredibly hard, and I was excited for their families, for whom a low-six-figure exit would be life-changing. I wondered if the company would develop an internal class hierarchy, then remembered it already had one.
The shares I exercised were worth about two hundred thousand dollars, before taxes. This was a windfall by my standards, if modest for the industry: it was less than the median salary at the social network everyone hated; less than the six hundred thousand dollars direct-deposited into an early support rep’s bank account; less than the multimillion-dollar sums that went to people I suspected had done indelible harm to coworkers. I felt no pride, only relief and guilt.
I was lucky. Draining my bank account to exercise my stock options was only tenable because I knew I could borrow money from family, or from Ian. Some of my coworkers, largely women in nontechnical roles whose work had been foundational to the company, but whose salaries did not allow them to save much in the city with the highest cost of living in the country, had been offered generous stock grants that they were unable to exercise after they left the company. Some women, I had heard, were promised extensions on their exercise windows, only to have the extensions vetoed by the board after the grants had expired. The acquisition was a once-in-a-lifetime bonanza. It passed them by.
Flat structure, meritocracy, non-nonnegotiable offers. Systems do work as designed.
That same spring, the CEO of the analytics startup stepped down. “I just need a break,” he told a business reporter. “It’s been a marathon.” On social media, he joined the ranks of industry thought-leaders contributing to the founder-realism genre, recommending therapy and community, microblogging his own emotional development in real time.
In the chat room for ex-employees of the analytics startup, my former coworkers lauded the decision. They joked about inviting the CEO to the channel. They rolled their emoji-eyes at his inspirational posts. They reminisced about the early team, griped about the CEO, and debated, as former employees of still-private companies were wont to do, whether our own stock options would ever be worth anything. I wondered if it had been traumatic for the CEO to leave the company he built, if it felt like grief. I wondered if he had regrets, and how long it would be until he did it all again.
Within a year of the CEO’s departure, the CTO and several engineers would return to the analytics startup to see it through. I wondered if they felt a loyalty to the product—if they would not be satisfied until the problem, technically speaking, was solved. I understood the appeal of returning to the company, though I knew I never could. It wasn’t just that I had traded the security of tech for more engaging work—and was hoping, against the odds, that it would last—but that I couldn’t imagine once again being so complaisant, so consumed.
A few months later, I wandered through the Mission, killing time before meeting a friend for lunch. Sitting outside a fast-casual Greek restaurant on Valencia Street were two men engaged in animated conversation, their napkins wadded on the table. Nearly five years had passed, but I recognized the CEO of the analytics startup immediately: gelled hair, slight frame, green jacket. He looked happy, relaxed, older. He looked just like anyone else.
Weekday lunch on the town, I thought—good for him. Then I turned and walked as quickly as possible in the opposite direction. I am confident he never saw me.