UNCANNY VALLEY

A MEMOIR

Anna Wiener

Copyright

4th Estate

An imprint of HarperCollinsPublishers

1 London Bridge Street

London SE1 9GF

www.4thEstate.co.uk

This eBook first published in Great Britain by 4th Estate in 2020

Copyright © Anna Wiener 2020

Cover design by Jack Smyth

Cover illustration © Hisashi Okawa

Anna Wiener asserts the moral right to be identified as the author of this work

A catalogue record for this book is available from the British Library

All rights reserved under International and Pan-American Copyright Conventions. By payment of the required fees, you have been granted the non-exclusive, non-transferable right to access and read the text of this e-book on-screen. No part of this text may be reproduced, transmitted, down-loaded, decompiled, reverse engineered, or stored in or introduced into any information storage and retrieval system, in any form or by any means, whether electronic or mechanical, now known or hereinafter invented, without the express written permission of HarperCollins

Source ISBN: 9780008296858

Ebook Edition © January 2020 ISBN: 9780008296872

Version: 2019-12-04

Contents

Cover

Title Page

Copyright

Incentives

Depending on whom …

Lightly hungover one …

Everyone I knew …

When I arrived …

San Francisco was …

As part of …

Every Tuesday, at …

I abandoned the …

In midsummer, news …

If, in New …

Noah took me …

One evening, a …

Being the only …

At Christmas, the …

Business was a …

The startup was …

As my annual …

I skimmed recruiter …

Scale

The open-source startup …

As an onboarding …

The engineers all …

I knew, even …

One slow evening …

Wasting time on …

I joined a …

At the beginning …

Friends hosted a …

From time to …

Silicon Valley had …

Do you think …

Venture capital was …

Northern California did …

We were too …

Epilogue

Acknowledgments

About the Author

About the Publisher

INCENTIVES

Depending on whom you ask, it was either the apex, the inflection point, or the beginning of the end for Silicon Valley’s startup scene—what cynics called a bubble, optimists called the future, and my future coworkers, high on the fumes of world-historical potential, breathlessly called the ecosystem. A social network everyone said they hated but no one could stop logging in to went public at a valuation of one-hundred-odd billion dollars, its grinning founder ringing the opening bell over video chat, a death knell for affordable rent in San Francisco. Two hundred million people signed on to a microblogging platform that helped them feel close to celebrities and other strangers they’d loathe in real life. Artificial intelligence and virtual reality were coming into vogue, again. Self-driving cars were considered inevitable. Everything was moving to mobile. Everything was up in the cloud. The cloud was an unmarked data center in the middle of Texas or Cork or Bavaria, but nobody cared. Everyone trusted it anyway.

It was a year of new optimism: the optimism of no hurdles, no limits, no bad ideas. The optimism of capital, power, and opportunity. Wherever money changed hands, enterprising technologists and MBAs were bound to follow. The word “disruption” proliferated, and everything was ripe for or vulnerable to it: sheet music, tuxedo rentals, home cooking, home buying, wedding planning, banking, shaving, credit lines, dry cleaning, the rhythm method. A website that allowed people to rent out their unused driveways raised four million dollars from elite firms on Sand Hill Road. A website taking on the kennel market—a pet-sitting and dog-walking app that disrupted neighborhood twelve-year-olds—raised ten million. An app for coupon-clipping enabled an untold number of bored and curious urbanites to pay for services they never knew they needed, and for a while people were mainlining antiwrinkle toxins, taking trapeze lessons, and bleaching their assholes, just because they could do it at a discount.

It was the dawn of the era of the unicorns: startups valued, by their investors, at over a billion dollars. A prominent venture capitalist had declared in the op-ed pages of an international business newspaper that software was eating the world, a claim that was subsequently cited in countless pitch decks and press releases and job listings as if it were proof of something—as if it were not just a clumsy and unpoetic metaphor, but evidence.

Outside of Silicon Valley, there seemed to be an overall resistance to taking any of it too seriously. There was a prevailing sentiment that, just like the last bubble, this would eventually pass. Meanwhile, the industry expanded beyond the province of futurists and hardware enthusiasts, and settled into its new role as the scaffolding of everyday life.

Not that I was aware of any of this—not that I was paying any attention at all. I didn’t even have apps on my phone. I had just turned twenty-five and was living on the edge of Brooklyn with a roommate I hardly knew, in an apartment filled with so much secondhand furniture it almost had a connection to history. I had a fragile but agreeable life: a job as an assistant at a small literary agency in Manhattan; a smattering of beloved friends on whom I exercised my social anxiety, primarily by avoiding them.

But the corners seemed to be coming up. The wheels were coming off. I thought, every day, about applying to graduate school. My job was running its course. There was no room to grow, and after three years the voyeuristic thrill of answering someone else’s phone had worn thin. I no longer wanted to amuse myself with submissions from the slush pile, or continue filing author contracts and royalty statements in places where they did not belong, like my desk drawer. My freelance work, proofreading and copyediting manuscripts for a small press, was also waning in volume, because I had recently broken up with the editor who assigned it to me. The relationship had been stressful, but reliably consuming: the editor, several years my senior, had talked about marriage but wouldn’t stop cheating. These infidelities were revealed after he borrowed my laptop for a weekend and returned it without logging out of his accounts, where I read a series of romantic and brooding private messages he exchanged with a voluptuous folk singer via the social network everyone hated. That year, I hated it extra.

I was oblivious to Silicon Valley, and contentedly so. It’s not that I was a Luddite—I could point-and-click before I could read. I just never opened the business section. Like anyone else with a desk job, I spent the majority of my waking hours peering into a computer, typing and tabbing through the days, the web browser a current of digital digression running beneath my work. At home, I wasted time scrolling through the photos and errant musings of people I should have long since forgotten, and exchanged endless, searching emails with friends, in which we swapped inexpert professional and dating advice. I read the online archives of literary magazines that no longer existed, digitally window-shopped for clothing I could not afford, and created and abandoned private, aspirational blogs with names like A Meaningful Life, in the vain hope that they might push me closer to leading one. Still, it never occurred to me that I might someday become one of the people working behind the internet, because I had never considered that there were people behind the internet at all.

In the manner of so many twentysomethings living in North Brooklyn at a time when an artisanal chocolate factory was considered a local landmark and people spoke earnestly about urban homesteading, my life was affectedly analog. I took photographs with an old, medium-format camera that had belonged to my grandfather, then scanned those photographs into my dying laptop, its internal fan whirring, to upload to my blogs. I sat atop busted amplifiers and cold radiators in Bushwick practice spaces, paging through back issues of prestige magazines, watching various crushes suck on hand-rolled cigarettes and finger their drumsticks and slide guitars, listening attentively to their noodling in preparation for my feedback to be solicited, though it never was. I went on dates with men who made chapbooks or live-edge wood furniture; one identified as an experimental baker. My to-do list always included archaic chores like buying a new needle for the record player I rarely used or a battery for the watch I never remembered to wear. I refused to own a microwave.

Insofar as I considered the technology industry of any importance to my own life, it was only because of circulating concerns specific to my professional world. An online superstore that had gotten its start in the nineties by selling books on the World Wide Web—not because the founder had a love of literature, but because he had a love of consumers, and consumptive efficiency—had expanded to become a digital bargain basement dealing in appliances, electronics, groceries, mass fashion, children’s toys, cutlery, and various nonnecessities manufactured in China. Having conquered the rest of retail, the online superstore had returned to its roots and seemed to be experimenting with various ways to destroy the publishing industry. It had even gone so far as to start its own publishing imprints, which my literary friends scorned and derided as cheesy and shameless. We ignored the fact that we had many reasons to be grateful to the website, as the publishing industry was being kept afloat by bestselling novels about sadomasochism and vampires who fucked, hatched in the incubator of the online superstore’s marketplace for self-published e-books. Within a few years, the founder, a chelonian ex–hedge funder, would become the wealthiest person in the world and undergo a montage-worthy makeover, but at the time we weren’t thinking about him. All that mattered to us was that the site was responsible for half of all book sales, which meant it had wrested control of the most important levers: pricing and distribution. It had us in its grip.

I did not know that the tech industry fetishized the online superstore for its cutthroat, data-driven company culture, or that its proprietary recommendation algorithms, which suggested vacuum cleaner bags and diapers alongside novels about dysfunctional families, were considered cutting-edge, admirable, and at the fore of applied machine learning. I did not know that the online superstore also had a lucrative sister business selling cloud-computing services—metered use of a sprawling, international network of server farms—which provided the back-end infrastructure for other companies’ websites and apps. I did not know that it was nearly impossible to use the internet at all without enriching the online superstore or its founder. I only knew that I was expected to loathe both, and I did—loudly, at any opportunity, and with righteous indignation.

On the whole, the tech industry was a distant and abstract concern. That fall, publishing was reeling from the proposed merger of the two largest houses, which together employed some ten thousand people and whose combined value pushed past two billion dollars. A two-billion-dollar company: the power and money were unfathomable to me. If anything could protect us from the online superstore, I thought, it was a two-billion-dollar company. I did not know about the twelve-employee unicorns.

Later, once I had settled into my life in San Francisco, I would learn that the year I spent drinking in dive bars with friends from the publishing industry, moaning about our impossible futures, was the same year many of my new friends, coworkers, and crushes swiftly and quietly made their first millions. While some of these friends were starting companies or embarking on two-year, self-imposed sabbaticals in their mid-twenties, I was sitting at a narrow desk outside of my boss’s office, tracking the agency’s expenses and trying to determine my value using my annual salary—increased, the previous winter, from twenty-nine thousand dollars to thirty—as a unit of measurement. What was my value? Five times as much as our new office sofa; twenty orders of customized stationery. While my future peers were hiring wealth advisers and going on meditation retreats in Bali to pursue self-actualization, I was vacuuming roaches off the walls of my rental apartment, smoking weed, and bicycling to warehouse concerts along the East River, staving off a thrumming sense of dread.

It was a year of promise, excess, optimism, acceleration, and hope—in some other city, in some other industry, in someone else’s life.

Lightly hungover one afternoon, eating a limp salad at the literary agency, I read an article about a startup that had raised three million dollars to bring a revolution to book publishing. The story led with a photo of the three cofounders, men who smiled widely against a pastoral background, like fraternity brothers posing for a graduation shot. All three wore button-down shirts; they looked like they had just shared a good chuckle. They looked so at ease, so convincing. They looked like the sort of men who used electric toothbrushes and never shopped at thrift stores, who followed the stock market and kept their dirty napkins off the table. The sort of men around whom I always felt invisible.

According to the news item, the revolution would come via an e-reading app for mobile phones that operated on a subscription model. This sounded niche to me, and the app’s pitch—access to a sprawling library of e-books for a modest monthly fee—seemed like the sort of promise that came with a lot of fine print. Still, something about the idea appealed.

The e-reading app was a new concept for publishing, where new ideas rarely emerged and were never rewarded. It didn’t help that publishing felt always on the brink of collapse. It was not just the monopolistic online superstore, or the two-billion-dollar merger, though these compounded and accelerated our anxieties. It was also the mores. The only way to have a successful and sustainable career in the publishing industry, it seemed, was to inherit money, marry rich, or wait for peers to defect or die.

Among the assistant class, my friends and I wondered whether there would be a place for us as the industry continued to shrink. A person could live on thirty thousand dollars a year in New York; millions did more with less. But take-home pay of seventeen hundred dollars a month was difficult to square with the social, festive, affluent lifestyle the publishing industry encouraged: networking drinks, dinner parties, three-hundred-dollar wrap dresses, built-in bookcases in Fort Greene or Brooklyn Heights. It was nice to get new hardcover books for free, but it would be nicer if we could afford to buy them.

Every assistant I knew quietly relied on a secondary source of income: copyediting, bartending, waitressing, generous relatives. These cash flows were rarely disclosed to anyone but each other. It was an indignity to talk about money when our superiors, who ordered poached salmon and glasses of rosé at lunch, seemed to consider low pay a rite of passage, rather than systemic exploitation in which they might feel some solidarity. Solidarity, specifically, with us.

The truth was that we were expendable. There were more English majors with independent financial support and strings of unpaid literary internships than there were open positions at agencies and houses. The talent pool was self-replenishing. Men in beige desert boots and women in mustard-yellow cardigans waited in the wings, clutching their cream-colored résumés. The industry relied, to some degree, on a high rate of attrition.

Still, my publishing friends and I were stubborn. We liked working with books; we clung to our cultural capital. There was a pervasive resentment around paying our dues, but we were prepared to pay them. A selective moral logic seemed to animate the industry: publishing had failed to innovate quickly, yes, but surely we—the literary, the passionate, lovers and defenders of human expression—wouldn’t lose to companies whose executives didn’t even show an appreciation for books. We had taste and integrity. We were nervous, and very broke.

I was very broke. Not poor, never poor. Privileged and downwardly mobile. Like many of my peers, I could afford to work in publishing because I had a safety net. I had graduated college debt-free, by no accomplishment of my own: my parents and grandparents had saved for my tuition since I was a blur on the sonogram. I had no dependents. I had secret, minor credit-card debt, but I did not want to ask for help. Borrowing money to make rent, or pay off a medical bill, or even, in a fit of misguided aspiration, buy my own wrap dress, always felt like a multifront failure. I was ashamed that I couldn’t support myself, and ashamed that my generous, forgiving parents were effectively subsidizing a successful literary agency. I had one year left on their health insurance. The situation was not sustainable. I was not sustainable.

My parents had always hoped that I would professionalize in medicine or law, immerse myself in something stable and safe. They were comfortable—my mother was a writer, and worked with nonprofits, and my father was in financial services—but they emphasized independence. My brother, who had graduated pre-recession, already had a successful career by the time he was my age. None of them understood the slow burn of the publishing hierarchy or the industry’s shabby, nostalgic glamour. My mother often asked, gently, why I was still an assistant—making coffee, taking coats—at twenty-five. She wasn’t asking for a structural explanation.

My desires were generic. I wanted to find my place in the world, and be independent, useful, and good. I wanted to make money, because I wanted to feel affirmed, confident, and valued. I wanted to be taken seriously. Mostly, I didn’t want anyone to worry about me.

Though I had the nagging suspicion that the e-book startup’s cofounders might be jockeying for a place on the wrong side of the issues I cared about—the side of the online superstore, the side that was already winning—at the expense of publishers, authors, and agents, I envied their sense of entitlement to the future. There was something unusual and attractive about people who had a vision for how the industry could evolve and a green light to get it done.

I didn’t know that three million dollars was considered a modest fund-raising round. I didn’t know that most startups raised money more than once, and three million dollars was experimental, pocket change. To me, that amount of money was a flag in the ground, an indication of permanence, as good as a blank check to go forth and take over. The future of publishing was here, I assumed. I wanted in.

I joined the e-book startup at the beginning of 2013, after a series of ambiguous and casual interviews. I had been primed to have expectations of a certain techie stereotype—antisocial and unwashed, sex starved and awkward—but the cofounders, who would never have referred to themselves as techies, immediately confounded this. The CEO was fast-moving, confident, and chiseled, and the chief technical officer, a soft-spoken systems thinker, was humble and patient. The creative founder, who referred to himself as the chief product officer, was an easy favorite. He had gone to art school on the East Coast and wore jeans that were so tight I felt I already knew him: he was like my friends from college, but successful. I was older than all three of them.

Conversation with the cofounders had been so easy, and the interviews so much more like coffee dates than the formal, sweaty-blazer interrogations I had experienced elsewhere, that at a certain point I wondered if maybe the three of them just wanted to hang out. They had, after all, recently moved across the country. It wasn’t like they wanted to live in New York—it was clear that they would have preferred the energy out west—but they needed to be closer to the industry they were disrupting, to build partnerships. Like the patron saint of mislaid sympathies, I speculated that perhaps they were just lonely.

They were, of course, not lonely. They were focused and content. All three were clean-shaven and had good skin. They wore shirts that were always crisp and modestly buttoned to the clavicle. They were in long-term relationships with high-functioning women, women with great hair with whom they exercised and shared meals at restaurants that required reservations. They lived in one-bedroom apartments in downtown Manhattan and had no apparent need for psychotherapy. They shared a vision and a game plan. They weren’t ashamed to talk about it, weren’t ashamed to be openly ambitious. Fresh off impressive positions and prestigious summer internships at large tech corporations in the Bay Area, they spoke about their work like industry veterans, lifelong company men. They were generous with their unsolicited business advice, as though they hadn’t just worked someplace for a year or two but built storied careers. They were aspirational. I wanted, so much, to be like—and liked by—them.

Because the role had been created specifically for me, the job was a three-month trial run. The scope and responsibilities were nebulous to all of us: some curating of in-app titles, some copywriting, various secretarial tasks. As a full-time contractor, I would be paid twenty dollars an hour, again with no benefits. The money didn’t look like much up front, but I calculated the annual salary and was gratified to see that it would amount to forty thousand dollars.

My friends in publishing were skeptical when I told them where I was going to work. They had a lot of questions I felt uneasy answering. Wouldn’t a subscription model undercut author royalties? Wasn’t it basically a cynical, capitalist appropriation of the public library system? Wasn’t an app like this parasitic at best? Was it all that different from the online superstore, and wouldn’t the app’s success come at the expense of the literary culture and community? I didn’t have a good response to most of these concerns. Mostly, I tried not to think about them. Smug and self-congratulatory, I translated most of my friends’ questions to mean, simply, What about us?

The startup’s office was a block from Canal Street, in a neighborhood the CEO called Nolita, the CTO called Little Italy, and the CPO called Chinatown. The surrounding area was tourist-addled even on weekdays, brimming with adults popping overstuffed cannoli and shooting tiny paper cups of espresso while their children eyeballed storefront displays of dusty parmesan wheels. The office was not so much an office as a spare table in the loftlike headquarters of a more established startup, one that enabled people to buy and sell art on the internet, at auction—a business model I did not fully understand, as the fun of auctions, I had always imagined, was the performative, feverish display of wealth and one-upmanship. I did not realize at the time that for people in the tech industry, such expressions of wealth were not just gauche but antiquated. There was nothing more civilized than hiding your money behind a browser.

The loft had creaky wood floors and a long kitchen counter running along one wall, which bore an assembly of pour-over vessels and sacks of small-batch coffee beans from local roasters. The bathrooms had showers. On my start date, I arrived at the table to find a welcome gift: a stack of hardcover books about technology, inscribed by the founders and stamped with a wax seal of the company logo: an oyster, unavoidably yonic, with a perfect pearl.

The e-book startup had millions in funding and job titles that suggested a robust and organized workforce, but the app itself was still in private alpha, used only by a handful of friends, family, and investors. There was only one other employee, a mobile engineer named Cam, whom the founders had been excited to hire away from a photo-editing app. The five of us sat around our mahogany table at the back of the loft, drinking coffee, as if in a perpetual board meeting.

For the first time in my career, I had some expertise. The men asked for my opinions—on the app’s reading experience, on the quality of the inventory, on how best to ingratiate ourselves with online reading communities—and listened for the answers. Despite misunderstanding the technical infrastructure and having little insight into strategy, I felt useful. It was thrilling to watch the moving parts of a business come together; to feel that I could contribute.

To celebrate the CTO’s birthday, we traveled to Midtown to see a movie about counterterrorism specialists. The movie opened with an audio montage of telephone calls made by people trapped in the World Trade Center on September 11. I did not want to continue watching, but more than that I did not know how to exit gracefully without having to explain that I had seen all of it happen at age fourteen, from the window of my high school Spanish classroom, four blocks away from the towers.

I considered faking something biological: gastroenteritis, menstruation. I considered the Irish goodbye. I resented that I had not done my research on the film, resented that I could not be a normal person with normal experiences doing a normal thing, like enjoying an action movie with my colleagues, without getting mired in unresolved PTSD. I fidgeted so badly that I lost an earring in the theater, and when the lights came up after the credits, the CTO got down on his knees to search for it, beckoning the others to join. I was embarrassed to see them scrambling across the floor, and moved that they would run their palms over the sticky synthetic carpet for me. After waiting for a few seconds, I exclaimed that I had found it, and the boys stood up to button their jackets and heave on their backpacks; nobody noticed when I removed the remaining earring and shoved it into the lint of my pocket.

We moved into the late winter light, and walked to a Japanese dessert bar around the corner. I had never been to a dessert bar, let alone a Japanese one. The boys were delighted by the variety. They reminded one another that this was on the company card, and overordered. Sitting with the four of them, watching as they dipped their spoons into each other’s desserts, resisting as they pushed their plates toward me to make sure I tasted everything, I tried to imagine what the other patrons thought about our group. I felt like a babysitter, a fifth wheel, a chaperone, a little sister, a ball and chain, a concubine. I felt indescribably lucky. At the end of the night, I walked downtown alone to the farthest possible subway station, savoring.

I befriended Cam, the other employee who was not a founder. During our lunch breaks we would venture forth into the neighborhood and return with sandwiches or leaky plastic containers of Vietnamese takeout, which we would eat in the conference room while he patiently answered my questions about the difference between front-end development and back-end programming. On occasion, we would talk about the burdens and responsibilities of being employees one and two of a startup that, despite not yet having a public product, was already considered hot. “I think this is a really good time for us to join the company,” he would reassure me. “I think we’re very well positioned.” He either did not know that I was a contractor, or was optimistic that I would be hired as a proper employee after the trial period.

Cam had a gentle, low-key nature. He loved his girlfriend, and her cat, and I loved hearing him talk about them. The only time I ever saw him get worked up was when I organized a company book club and none of the cofounders followed through. They were too busy building the app, they said. Who had time for book clubs? I understood this and did not particularly mind, but Cam chastened them in the company chat room and then took me out for soup. He insisted that they were rude and in the wrong; he insisted that I was working incredibly hard to build the company culture.

This was only partially true. After the first few weeks, during which I wrote website copy, tried to help recruit engineers from a short list of top universities, and edited the user privacy agreement to make it sound more like a friend than a lawyer, it seemed that mostly the founders were overpaying me to look for a more permanent office space and order them snacks: single-serving bags of cheese crackers, tiny chocolate bars, cups of blueberry yogurt.

The concept of eating a snack at work was new to me. At the literary agency, eating at work during non-lunch hours was a source of not-insignificant shame, and gnawing at a bagel or crunching through a bag of bodega pretzels was, I thought, regarded as sloppy and unprofessional. In previous jobs, my inability to keep my homemade lunch untouched until lunchtime was an expression of my lack of self-control, the reason I still had baby fat at an age when the fat might have been postpartum, but instead was just me; I was the baby. The boys, by contrast, snacked throughout the day. They ate chips at their computers and dusted their hands off on paper towels, swished seltzer water and crumpled the cans beside their keyboards. I meticulously noted their preferences and tried to keep things interesting: a box of clementines one week, bags of cheddar popcorn the next.

With Cam in mind, I took it upon myself to bolster the company culture. I persisted with the book club, and the founders continued to snub it. I organized team outings, including one to a gilded private library that had belonged to a famed financier, a goliath of nineteenth-century banking. We wandered the building, admiring the imposing floor-to-ceiling bookcases, the twisting staircases and gold-painted ceiling, taking photographs and posting them to social media. This was how the app should feel, we all agreed: luxurious, but not intimidating; infinite.

The private library was a hit, but the truth was that three men in their early twenties with millions in the bank did not need me to take them on reading-themed field trips. It would be more cost-effective for them to order their own snacks. Despite Cam’s encouragement, they also did not need me to build the company culture. They did not really need me for anything. The culture, insofar as our tiny company had one, revolved around the founders. While they sometimes bickered, I never saw anyone leave the conference room angry. They seemed to be happiest unwinding on the overstuffed couch, playing video games together and drinking domestic beers. They did not need to team-build or bond, and mostly that wasn’t what we were doing. We were building a company—or they were, and I was watching.

When we did find a new office space, on a prime block in the west twenties—a part of the city some referred to, in an act of taxonomic hubris, as Silicon Alley—it also belonged to another startup, but this time the circumstances were different. The lease-holding startup was working on something in the media space, and its headcount had grown and shrunk as if the company were weight-cycling. At a team meeting, our CEO gravely noted that the media startup had already pivoted multiple times over. I asked what he meant by this, and all four men looked at me suspiciously. Pivoting meant that they had changed their business model in an effort to generate revenue. Pivoting meant they were worried about runway. Pivoting meant they were a cautionary tale. Only the two cofounders were left, tucked off to the side. Everyone else had been let go once funding ran out.

The specter of these laid-off employees lingered, a reminder to work harder. Most of our days were spent heads-down at our desks, furiously instant-messaging each other from across the underfurnished office. We took synchronized lunches and talked about strategy. We returned to our computers and assiduously avoided eye contact. We held long and impassioned meetings about partnerships and design, and ordered in pizza when these meetings crossed into night. Everything felt urgent, high stakes.

One afternoon, the CEO summoned us into a conference room to demo the pitch deck he was making for meetings with publishers. He opened by stating that ours was the era of the sharing economy. Millennials, he said, as if he were not one of them, weren’t into ownership, but experiences. This was not just a new market strategy, but a cultural ideology. Pioneering digital platforms in the sharing and subscription economies enabled people to stream films and albums and video games, rent cocktail dresses and three-piece suits, reserve bedrooms in strangers’ houses, and ride shotgun in strangers’ cars. Music, movies, television, retail, and transportation had been disrupted. The time had come for books. The CEO flipped to a slide that displayed the logos of various successful subscription platforms, with our logo at the center.

Technology products were lifestyle products, the CEO said. As he continued his pitch, it became clear to me that the utility of the e-reading app was not so much about reading as it was about signaling that you were the type of person who would read, and who would use an app with a cutting-edge reading experience and innovative, intuitive design. The ideal user of the app, I deduced, was a person who thought of themselves as a reader, but wasn’t, not really: licensing cost money, and anyone reading more than a few books a month could generate a licensing expense exceeding the subscription fee. Books were an opportunity, I understood, but not the endgame. It was just one type of content, and only the first step. Expansion: that was the endgame. Probably. I trusted them to figure it out.

The CEO did not acknowledge that the reason millennials might be interested in experiences—like the experience of renting things they could never own—was related to student loan debt, or the recession, or the plummeting market value of cultural products in an age of digital distribution. There were no crises in this vision of the future. There were only opportunities.

I tried to determine whether I could believe in this. The CEO was charming, and committed to the company and its vision. Perhaps he and the other two founders were also brilliant. Their investors in Silicon Valley must have thought so. But they seemed to be least interested in the part of the business I cared about most—the books. “Hemingway” had been misspelled in the CEO’s pitch deck: two m’s.

More relevantly, the model—starting with books, and taking it from there—seemed to hew all too closely to that of the online superstore. I began to wonder why it was, exactly, that they had hired me. I had been operating under the vain premise that it was because I knew something about books: I could be a bridge between the old and new guards. I had fancied myself a translator; I had fancied myself essential. Later, once I better understood the industry-wide interest in promoting women in tech—if not up the ranks, then at least in corporate marketing materials—I would allow myself to consider that perhaps I was more important to the aesthetic than critical to the business.

What I also did not understand at the time was that the founders had all hoped I would make my own job, without deliberate instruction. The mark of a hustler, a true entrepreneurial spirit, was creating the job that you wanted and making it look indispensable, even if it was institutionally unnecessary. This was an existential strategy for the tech industry itself, and it did not come naturally to me. My imagination was still tailored to the parameters of publishing: I suggested that the e-book startup host a reading series, as a form of outreach to the literary community. Perhaps we should have a book blog, I mused. Instead, the startup sent third-wave-coffee trucks to distribute free espresso drinks and pastries at industry conferences, where exciting swag historically meant a cotton tote bag or an advance reader’s copy of a debut work of literary fiction. I had trouble strategizing at scale.

“She’s too interested in learning, not doing,” the CEO typed once into the company chat room. This was an accident—he meant it only for the other two cofounders. We huddled in the conference room and he apologized sincerely, while I looped the words over and over in my head. I had always been interested in learning, and I had always been rewarded for it; learning was what I did best. I wasn’t used to having the sort of professional license and latitude that the founders were given. I lacked their confidence, their entitlement. I did not know about startup maxims to experiment and “own” things. I had never heard the common tech incantation Ask forgiveness, not permission.

In an effort to self-educate, I read blog posts about the startup mentality and did my best to imitate it. The CEO had published one a year earlier titled “How to Make an Impact During the First Month of Your Startup Job,” and I resented myself for missing the writing on the wall. Take ownership, he had advised in the post. Be optimistic. Write down your opinions.

In the end, I resorted to writing long, embarrassing, and unsolicited emails to the founders, declaring my passion for reading. An e-reading app needed a passionate reader on staff, I was sure of it—maybe I didn’t know how to be a good startup employee, at least not yet, but surely they would benefit from having me, a focus group of one, on the team anyway. After several long and heartfelt emails and another painful one-on-one huddle in the conference room, it was clear that there was no way I could stay. This was not the right moment in the company’s journey, they said, for someone like me to get up to speed. The areas where I could add value would not be active for some time.

The cofounders all wanted to help me find a new job. They assumed I wanted to continue working in tech, and I didn’t disabuse them of this. I was reluctant to return to publishing. I had tried to strike out on my own and had failed. Besides, I had been traitorous, joining a startup trying to rock the book world, and did not want to face the possibility that I might now be unwelcome.

I had also been spoiled by the speed and open-mindedness of the tech industry, the optimism and sense of possibility. In publishing, no one I knew was ever celebrating a promotion. Nobody my age was excited about what might come next. Tech, by comparison, promised what so few industries or institutions could, at the time: a future.

Most of the founders’ professional network—the other startups in their venture capitalists’ portfolios—lived in the Bay Area. The CPO spoke wistfully of California. “I maintain that San Francisco is the best place to be a young person,” he told me. “You should really try to get out there before too long.” I wanted to tell him that I thought I was still young: I was only twenty-five. Instead, I told him I would try.

Everyone I knew in San Francisco had already left. Our college class had graduated straight into a recession, and while most of us trudged to New York or Boston to compete for unpaid internships and other scraps of a ravaged economy, those who moved west refused to bend to despair. They chose instead to hide out for a while, work on their art. They lived in sun-flooded apartments, took part-time service jobs, and had complicated, consuming social lives. They freely experimented with hallucinogens and polyamory; smoked weed and slept in and day-drank; went to BDSM parties and wolfed burritos afterward. They started bands and did occasional sex work. They spent weekends in the mountains or the woods or on the beach, camping and hiking and participating in other wholesome activities that we made fun of back in New York.

This utopia was short-lived. It was being replaced by a late-capitalist hellscape, my friends reported. Rents were spiking. Art galleries and music venues were closing. Bars were overrun with men in their twenties wearing corporate-branded T-shirts, men who never finished their beers and complained whenever anyone on the sidewalk smoked a cigarette too close to the door. Men who wore stability running shoes to nightclubs. Men who said “K” instead of “thousand.”

Dating websites were flooded with milquetoast strivers who earnestly listed business-management guides among their favorite books and arrived at dinner wearing backpacks stamped with the names of their employers. Young CEOs were showing up to sex parties expecting to play only with other young CEOs. My friends, covered in glitter and wearing tiny nut-hammocks and rolling on ecstasy, found themselves marching in the annual Pride parade alongside primary-colored, brand-consistent, family-friendly floats designed by heterosexual digital-marketing managers.

The city had begun to bend to the on-demand desires of recent college graduates with plump bank accounts. Even Oakland was becoming unaffordable for artists and writers working as loosely credentialed yoga instructors or grocery store cashiers. There weren’t any jobs, my friends said, unless you wanted to work for a tech company. It went without saying that none of them did. Within a few years, they departed for gentrifying neighborhoods in New Orleans or Los Angeles, or found their way to graduate school, their flight paths and cross-country road trips doing double duty as funeral marches for a beloved city that, they all assured me, no longer existed.

When I traveled to San Francisco in the spring, to interview for a customer-support position at a data analytics startup, I didn’t mention it to my ex–Bay Area friends. I dreaded how they would react if they knew I was angling for a job in the tech industry, that I had even a shred of interest in joining the people on whom they blamed their displacement—the people who had ruined their fun. I took the train from the airport into the city, feeling treacherous and estranged.

Using the millennial-friendly platform for renting strangers’ bedrooms, I had booked a room in the Mission, in an apartment that belonged to a couple in their mid-fifties. It was my first time using the app, and as I stood on the front steps of an ornate Victorian, I felt like an orphan of nineteenth-century literature, a child on the brink of a new adventure. Welcome home, the home-sharing platform’s marketing materials had gushed, exuding familial warmth with bright, bold colors. But while the website emphasized community, coziness, a richer life through new connections and novel experiences, my hosts greeted me coolly—a reminder that this was, above all, a transaction.

As the husband showed me around my room—guest towels in the hope chest, lemon tree in the backyard—he asked what had brought me to town. I explained with some trepidation that I was there to interview at a startup. I knew that the neighborhood had long been an enclave for artists, activists, and other groups without enough money to hold their own in housing court. I wanted to be sensitive. He nodded knowingly, without judgment, and shrugged. “We host full-time,” he said. “I guess you could say we work for a startup, too.”

Could I? He and his wife had both quit their day jobs, in the nonprofit sector, to provide the trappings of an authentic urban experience—different enough to be interesting, but generic enough to be comfortable—to tourists and interlopers like me. They slept in the basement. They weren’t employees. They were part of the product.

It was my first time paying to stay with strangers. The apartment was clean and welcoming, full of overstuffed furniture and bowls of fruit, but I didn’t know whether relaxing with a book on the sofa or borrowing kitchen implements to slice a ripe peach would be considered a breach of the home-sharing platform’s terms of service—I’d only booked a room, after all. The policy had extensively covered the company’s liability but didn’t offer any specifics on how to behave. To play it safe, I walked carefully between my bedroom and the bathroom, as if the hallway were a grooved track—as if I were trespassing, intruding on a family and a life that did not belong to me.

The interview had been arranged with the help of the e-book startup’s CEO, who advised that big data was a hot space. According to him, the analytics startup—just four years old, founded by college dropouts—had already infiltrated the market with impressive speed and ferocity. The company had twelve million dollars in venture funding, thousands of customers, and seventeen employees. “Our investors say they’re the next unicorn,” the e-book startup’s CEO had enthused, tipping back in his chair. “It’s a rocket ship.” It was easy to get me to want something.

I was not particularly excited about customer support, but it was an entry-level job that required no programming knowledge. As a sociology major with a background in literary fiction and three months of experience in snack procurement, I assumed I was not in a position to be picky. The e-book startup’s cofounders had been adamant that customer support was a temporary state. If I hustled, all three of them agreed, I would quickly find myself in a more interesting, autonomous, impressive role. I didn’t know that in tech, qualifications—at least the traditional ones, like advanced degrees or experience—were irrelevant when superseded by cheerful determination. I was still behaving like a young professional in a world where dues-paying mattered.

In an effort to hype myself up, I developed the theory, however flimsy, that analytics was a natural extension of my liberal arts education. The e-book startup had used the analytics software to track our alpha users through the app, and I had enjoyed looking at some of the data: what our investors were reading, and abandoning; whether or not people read public-domain books with cover art designed by the CPO, which we had added to bolster the library. In a certain light, I tried to convince myself, business analytics could be seen as a form of applied sociology.

The night before the interview, in the privacy of my rental bedroom, I read interviews and puff pieces about the analytics startup’s cofounders, now twenty-four and twenty-five years old. According to the tech blogs, they’d just been two underage students with one Silicon Valley internship between them, and a smart, practical, easily pivotable dream of a world driven by the power of big data. This was a dream that greatly appealed to the admissions committee of a renowned seed accelerator in Mountain View, which offered funding and connections in exchange for a 7 percent stake. The accelerator’s slogan was an inspirational exhortation to founders to make things people wanted—not, I noted, needed. It boasted a handful of success stories—a grocery-delivery app, a livestreaming site, the home-sharing platform—as well as dozens of failures. The CEO and technical founder had left their college in the Southwest to join the accelerator, then enrolled full-time in the ecosystem.

Several months prior, a tech blog had published an article announcing the analytics startup’s first major fund-raising round of ten million dollars. When asked how he would spend the new funding, the CEO made his priorities clear: he would pay the first hundred employees far above market, he said, and spoil current employees to retain them. This was the language of customer acquisition, but I didn’t know. I didn’t think at all about the stratification, either; how the hundred-and-first employee might feel. I’d never worked anywhere with a hundred people—I’d never worked anywhere with twenty. I’d certainly never worked anywhere that wanted to spoil its employees and had the means to do it. Generous, I thought. I found the tenacity winning.

When I arrived at the analytics startup’s headquarters, I was surprised to find that the whole enterprise was peanut-sized. The office, however, was huge—at least seven thousand square feet, with a polished-concrete floor, and mostly unfurnished. About fifteen employees were clustered together at the far end of the room, all gazing deeply into monitors. Some stood at elevated desks, legs spread sturdily, feet cushioned by little rubber mats. Every work space had its own colorful clutter: pots of succulents and other dying plants, anime figurines and stacks of books, bottles of nice liquor. On one was perched an obelisk of empty cans, husks of the same high-caffeine energy drink. The open-plan setup made it look like a classroom. No one there looked over the age of thirty.

I stood in the doorway and counted the women. There were three. They wore jeans and sneakers, oversized cardigans over T-shirts. I had dressed carefully, in a blue shift, heeled boots, and a thin blazer. It was what I always wore to interviews, and I thought it signaled professionalism and seriousness. In publishing, an ensemble like this was nice, but still dowdy enough to be nonthreatening. Inside the startup, I felt like a narc. I shrugged off the blazer as discreetly as possible and stuffed it into my tote bag.

The first interview was with the manager of the Solutions team, the customer-facing division. He was jolly and hirsute, wearing faded jeans and a company T-shirt that declared I AM DATA DRIVEN. I resisted asking if it needed a hyphen. He sat down in one of the ergonomic desk chairs, leaned back, and bounced lightly, like a baby. Through the glass door of the conference room, on which was taped a handwritten sign designating it THE PENTAGON, I watched a wiry man in a plaid shirt wiggle past on a RipStik, waving one arm for balance and shouting enthusiastically into a golden telephone receiver.

The solutions manager placed his elbows on the table and leaned toward me, explaining that we would be going through a series of questions together so I could demonstrate how I problem-solved. “So,” he said, as if he were asking me to let him in on a secret, “how would you calculate the number of people who work for the United States Postal Service?” We sat in silence for a moment. I wouldn’t, I thought; I would look it up on the internet. I wondered if perhaps this was actually a test of my tolerance for bullshit and inefficiency—if the sassy response could also be the right one. I had no idea what the solutions manager wanted. Then he handed me a marker and pointed toward the whiteboard. “Why don’t you get up on the board and show me how you’d work it out?” he asked. It wasn’t a suggestion.

In the four hours that followed, the solutions manager and the wiry man I had earlier seen cruising past, a sales engineer, walked me through a series of questions and puzzles. The sales engineer seemed to be about my age, and had an unaffected drawl and manic, infectious energy. His speech was littered with folksy aphorisms. “Butter my biscuits,” he said, when I complimented his oversized belt buckle. “Now we’re cooking with gas,” he said, teaching me how to reverse a string on the whiteboard.

Both the sales engineer and the solutions manager exclusively referred to the data-analytics software as “the tool.” Both of them asked questions that were self-conscious and infuriating. “What’s the hardest thing you’ve ever done?” asked the solutions manager, twisting his wedding ring around and around. “How would you explain the tool to your grandmother?”

“How would you describe the internet to a medieval farmer?” asked the sales engineer, opening and closing the pearl snaps on his shirt, sticking his hand thoughtfully down the back of his own waistband.

Because interviewing at the e-book startup had been breezy and comfortable, I expected the same from the analytics company. No one had warned me that in San Francisco and Silicon Valley interviewing was effectively punitive, more like a hazing ritual than an airtight vetting system. A search-engine giant down in Mountain View was famous for its interview brainteasers, and while it had already denounced the practice, finding it useless as an indicator of future job performance, others insisted on enshrining it as tradition: learning from another company’s mistakes took on a new meaning when those mistakes had proved lucrative. Across the Bay Area, applicants were routinely asked questions like “How many square feet of pizza are eaten in the United States every year?” and “How many Ping-Pong balls fit in an airplane?” Some of them, meant to determine whether an interviewee was a culture fit, were dredged in middle-school kitsch. “If you were a superhero, what would your superhero strength be?” asked straight-faced human resources professionals. “When you walk into a room, what’s your theme song?” That afternoon, mine was a dirge.

After a few hours, the technical cofounder entered the conference room, looking confidently unprepared. He noted, with an apology, that he hadn’t done many interviews before and didn’t have any questions to ask. Still, he said, the office manager had slated an hour for our conversation.

This seemed okay: I figured we would talk about the company, I would ask routine follow-up questions, and they would finally let me out, like an elementary-school student, and the city would absorb me and my humiliation. Then the technical cofounder told me that his girlfriend was applying to law school, and he’d been helping her prep. Instead of a conventional interview, he said, he was just going to have me take a section of the LSAT. I searched his baby face to see if he was kidding.

“If it’s cool with you, I’m just going to hang out here and check my email,” he said, sliding the test across the table and opening a laptop. He set a timer on his phone.

I finished early, ever the overachiever. I checked the test twice. I joked that it was the closest I’d ever come to applying to law school—my mother would be so proud. The technical cofounder shot me a thin smile, slipped the papers under his computer, and left the room.

I sat in his wake, wondering what I was waiting for. There was not a doubt in my mind that I would not get the job. Not only had I surely demonstrated that I was unemployable, but I felt certain I’d been a vivid caricature of the dotty, linty liberal arts major—the antithesis of all that the tech industry stood for.

Still, though the interviews had been inane, they only served to fuel me. Here was a character flaw on parade, my industry origin story: I had always responded well to negging.

I would wonder for years if the analytics startup offered me the job because the entire interview process had revealed a degree of obedience desirable in a customer support representative, and in an employee—if they knew I would ultimately be a pushover, loyal and easily controlled. Eventually, I learned that it was actually just because I had managed a perfect score on the LSAT section they had administered. This knowledge would make me feel simultaneously cocky and displaced, of superior intelligence and crushing foolishness. A part of me had hoped they’d seen something latent and unique, some potential. I was always overthinking things.

The offer included medical and dental coverage, a four-thousand-dollar relocation stipend, and a starting salary of sixty-five thousand dollars a year. The manager informed me that the salary was above market and nonnegotiable. I couldn’t fathom being someone who made that much money, much less someone who would try to negotiate for more. With my skill set, or lack thereof, I couldn’t believe anyone wanted to pay me that much to do anything.

The solutions manager did not mention equity, and I didn’t ask. I did not know that early access to equity was a reason people joined private companies at the startup stage—that it was the only way anyone other than VCs and founders got rich. I did not even know that equity was an option. The company’s in-house recruiter would eventually intervene, to recommend that I negotiate to include even a small stake. His rationale was simple: all the other guys had some. No one told me how much it was worth, or how big the pool was, and I did not know to ask.

High on the feeling of being professionally desirable, I told the solutions manager I would sleep on it.

The analytics startup gave me three weeks. Back in Brooklyn, I invited friends over as I packed up the apartment. One evening, after a few drinks, a close friend asked whether I was sure I was making the right decision. I’d enjoyed working in publishing, she reminded me, idly popping bubble wrap between her fingers. Was it perhaps premature to throw in the towel? She promised not to judge if I decided, last minute, not to go. “Mobile analytics,” she said, trying on a pair of vintage spectator pumps that I had purchased in the midst of an identity crisis. “What is that? Do you care about it? And customer support—aren’t you worried it’ll be soul ruining?”

I was worried about a lot of things: loneliness, failure, earthquakes. But I wasn’t too worried about my soul. There had always been two sides to my personality. One side was sensible and organized, good at math; appreciative of order, achievement, authority, rules. The other side did everything it could to undermine the first. I behaved as if the first side dominated, but it did not. I wished it did: practicality, I thought, was a safe hedge against failure. It seemed like an easier way to move through the world.

Still, I had trouble admitting to my social group that I was moving across the country solely to work at a startup. It was embarrassing to articulate how excited I was to see what the fuss was about—it seemed, among my countercultural and creative friends, shrewd and cynical to be curious about business. I was selling out. In reality, I was not paying attention: those who understood our cultural moment saw that selling out—corporate positions, partnerships, sponsors—would become our generation’s premier aspiration, the best way to get paid.

At the time, though, it was corny to be openly enthusiastic about technology or the internet. For the most part, my friends were late and reluctant adopters. They had accounts on the social network everyone hated, but only used them to RSVP to poetry readings and DIY shows they had no intention of attending. Some defiantly carried flip phones without internet access, preferring to call those of us with desk jobs whenever they were out and needed directions. No one owned an e-reader. As the tides turned digital, my milieu was grounding itself firmly in the embodied, tangible world.

Out of self-protection, I stuck to the narrative that I was moving across the country just to try something new. I had never even lived outside of the tristate area. San Francisco had a great music scene, I said, unconvincingly, to anyone who would listen. It had medical marijuana. Working in analytics would be an experiment in separating my professional life from my personal interests. The startup gig was just a day job, I claimed, something to support me while I was otherwise creatively productive. Maybe I would start the short-story collection I had always wanted to write. Maybe I would take up pottery. I could finally learn bass.

It was easier, in any case, to fabricate a romantic narrative than admit that I was ambitious—that I wanted my life to pick up momentum, go faster.

When I arrived back in San Francisco, with a fresh haircut and two fraying duffel bags, I felt intrepid and pioneering. I did not know that thousands of people had already headed west for a crack at the new American dream, that they had been doing so for years. I was, by many standards, late.

It was a moment of corporate obsequiousness to young men. Tech companies were importing freshly graduated computer science majors from all over the world, putting them up in furnished apartments, paying their cable and internet and cell phone bills, and offering hundred-thousand-dollar signing bonuses as tokens of thanks. The programmers arrived with a flood of nontechnical carpetbaggers: former Ph.D. students and middle-school teachers, public defenders and chamber music singers, financial analysts and assembly-line operators, me.

I had booked another bedroom using the home-sharing platform, this time in the South of Market neighborhood, several blocks from the office. The room was on the garden level of a duplex, adjacent to a concrete patio and accessed through an alley, just past the recycling bins. It was decorated with the same lightweight, self-assembly furniture as my friends’ bedrooms back in Brooklyn. The woman who operated the rental was an entrepreneur in the renewable-energy space and described herself as never home.

A few small boxes of my books, bedding, and clothing were already at the analytics startup, stacked in a supply closet. I had been self-conscious about spending down the relocation stipend, wanting to save money for the company. A part of me worried that if I spent too much, the offer would be rescinded. I didn’t want my new manager to think I was frivolous. Others had expensed new furniture, meals, weeks of rent, but I didn’t know that. I was still operating according to publishing austerity.

The home-sharing platform offered an aspirational fantasy that I appreciated. Across the world, people were squeezing out the last of strangers’ toothpaste, picking up strangers’ soap in the shower, wiping their noses on strangers’ pillowcases. There I was as I had always been, only sleeping in a stranger’s bed, fumbling to replace a stranger’s spring-loaded toilet-paper holder, ordering sweaters off a stranger’s Wi-Fi network. I liked examining someone else’s product selections, judging their clutter. I wasn’t thinking about how the home-sharing platform might also be driving up rents, displacing residents, or undermining the very authenticity that it purported to sell. Mostly, the fact that it functioned, and nobody had murdered me, seemed like a miracle.

I had given myself a few days to get adjusted before starting the job. In the mornings, I bought coffee at a laundromat, consulted a crowdsourced reviewing app to find something to eat, and returned to my bedroom to spend the rest of the day reading technical documentation for the analytics software and panicking. The documentation was indecipherable to me. I didn’t know what an API was, or how to use one. I didn’t know how I would possibly provide technical support to engineers—I couldn’t even fake it.

The night before my first day of work, too unmoored and overwhelmed to sleep, I scrolled through previous guests’ reviews of my room and realized that the apartment was owned by one of the founders of the home-sharing platform. I looked up the founder’s name and read an interview in which he detailed how designers could follow in his footsteps and become entrepreneurs. He called them “designpreneurs.” I watched a video of him delivering the keynote at a tech conference, breathing excitedly into the mic. I learned that he and his two cofounders had raised over a hundred million dollars, and investors were desperate to give them more.

I looked around me at the blank walls, the closet door tilted on its hinges, the bars on the window, eager to identify hints of his success. But the designpreneur hadn’t slept in the room for years. He had moved into a gleaming, art-filled warehouse conversion close to his office. He’d left nothing behind.

The analytics startup made a pickax-during-the-Gold-Rush product, the kind venture capitalists loved to get behind. History saw the Gold Rush as a cautionary tale, but in Silicon Valley, people used its metaphors proudly, provided they were on the right side of things. Pickaxes were usually business-to-business products. Infrastructure, not services. Just as startups in New York were eager to build off their city’s existing cultural legacy, by creating services for media and finance—or, more commonly, creating sleek interfaces to sell things that would require more time, money, energy, or taste to buy elsewhere—the same was true of the Bay Area, where software engineers sought to usurp older technology companies by building tools for other software engineers.

It was the era of big data, complex data sets facilitated by exponentially faster computer processing power and stored, fashionably, in the cloud. Big data encompassed industries: science, medicine, farming, education, policing, surveillance. The right findings could be golden, inspiring new products or revealing user psychology, or engendering ingenious, hypertargeted advertising campaigns.

Not everyone knew what they needed from big data, but everyone knew that they needed it. Just the prospect incited lust in product managers, advertising executives, and stock-market speculators. Data collection and retention were unregulated. Investors salivated over predictive analytics, the lucrative potential of steroidal pattern-matching, and the prospect of bringing machine-learning algorithms to the masses—or, at least, to Fortune 500 companies. Transparency for the masses wasn’t ideal: better that the masses not see what companies in the data space had on them.

The analytics startup wasn’t disrupting anything so much as unseating big-data incumbents: slow-moving corporate behemoths whose products were technically unsophisticated and bore distinctly nineties user interfaces. The startup not only enabled other companies to collect customized data on their users’ behavior without having to write much code or pay for storage, but it also offered ways to analyze that data in colorful, dynamic dashboards. The cofounders had prioritized aesthetics and hired two graphic designers off the bat: men with signature hairstyles and large followings on a social network for people who referred to themselves as creatives and got excited about things like font sizing and hero images. In general, it was hard to say what, exactly, the designers did all day, but the dashboards were both friendly and elegant. The software looked especially pleasing, trustworthy, airtight. Good interface design was like magic, or religion: it cultivated the mass suspension of disbelief.

I had no qualms about disrupting extant corporations in the big-data space, no inherited nostalgia or fondness for business. I liked the underdog. I liked the idea of working for two kids younger than I was, who had dropped out of college and were upending the script for success. It was thrilling, in that sense, to see a couple of twentysomethings go up against middle-aged leaders of industry. It looked like they could win.

I was employee number twenty, and the fourth woman. Prior to my arrival, the Solutions team—four men, including the manager—had handled customer tickets themselves, attacking the support queue in shifts at the end of the workday, relaying the responsibility to avoid consecutive office-bound midnights. This strategy was effective for a while, but the user base was ballooning. The men couldn’t sustain the practice; they had their own jobs to do. They rearranged their desktop belongings and cleared a space for me.

The men on the Solutions team weren’t like the men from the e-book startup. They were weirder, wilder, funnier, harder to keep up with. They wore Australian work boots and flannel and durable, recycled polyester athletic vests, drank energy shots in the late afternoon and popped vitamin D in the mornings to stay focused and alert. They chewed powdered Swedish tobacco, packing it juicily behind their gums. Deep house and EDM leaked from their oversized headphones. At team gatherings they drank whiskey, neat, and, the following mornings, were prone to pounding a viscous liquid jacked up with electrolytes—sold as a remedy for small children with diarrhea—to flush away their hangovers. They had gone to top-tier private colleges and were fluent in the jargon of media studies and literary theory. They reminded me of my friends who had left San Francisco, but more adaptable and opportunistic, happier.

The solutions manager assigned me an onboarding buddy, Noah, a curly-haired twenty-six-year-old with a forearm tattoo in Sanskrit and a wardrobe of workman’s jackets and soft fleeces. Noah was warm and loquacious, animated, handsome. He struck me as the kind of person who would invite women over to get stoned and look at art books and listen to Brian Eno, and then actually spend the night doing that. I had gone to college with men like this: men who would comfortably sit on the floor with their backs against the bed, men who self-identified as feminists and would never make the first move. I could immediately picture him making seitan stir-fry, suggesting a hike in the rain. Showing up in an emergency and thinking he knew exactly what to do. Noah spoke in absolutes and in the language of psychoanalysis, offering definitive narratives for everyone, everything. I had the uneasy feeling that he could persuade me to do anything: bike across America; join a cult.

Noah and I spent my first few weeks in various corners of the office, carting around an overflowing bowl of trail mix and a rolling whiteboard, on which he patiently diagrammed how cookie tracking worked, how data was sent server-side, how to send an HTTP request, how to prevent a race condition. He was patient and encouraging, and made direct eye contact as we pushed through problem sets of hypothetical customer questions, various scenarios in which the software—or, more realistically, the user—had a meltdown.

The product was actually deeply technical, though the company talked up its usability. The amount of information I needed to absorb, to be even marginally helpful to our customers, was intimidating. The learning curve looked unconquerable. Noah gave me homework and pep talks. He told me not to worry. Our teammates handed me beers in the late afternoon, and were confident and reassuring that I, too, would eventually scale up. I trusted them entirely.

I was happy; I was learning. For the first time in my professional life, I was not responsible for making anyone coffee. Instead, I was solving problems. My job involved surveying strangers’ codebases and telling them where they’d gone wrong in integrating our product with theirs, and how to fix it. The first time I looked at a block of code and understood what was happening, I felt like nothing less than a genius.

It did not take long for me to understand the fetish for big data. Data sets were mesmerizing: digital streams of human behavior, answers to questions I didn’t know I had. There was more every second. Our servers, and the company’s bank account, absorbed this unstoppable wave.

Our bread and butter was engagement: actions that demonstrated the ways users were interacting with a product. This was a turn away from the long-running industry standard, which prioritized metrics like page views and time on site, metrics that the CEO called bullshit. Engagement, he said, was distinguished from the bullshit because it was actionable. Engagement generated a feedback loop between the user and the company. User behavior could dictate product managers’ decisions. These insights would be fed back into an app or website, to dictate or predict subsequent user behavior.

The software was flexible, intended to function as easily for fitness trackers or payment processors as for photo-editing and ride-sharing apps. It could be integrated into online boutiques, digital megamalls, banks, social networks, streaming and gaming websites. It gathered data for platforms that enabled people to book flights or hotels or restaurant reservations or wedding venues; platforms for buying a house or finding a house cleaner, ordering takeout or arranging a date. Engineers and data scientists and product managers would inject snippets of our code into their own codebases, specify which behaviors they wanted to track, and begin collecting data immediately. Anything an app or website’s users did—tap a button, take a photograph, send a payment, swipe right, enter text—could be recorded in real time, stored, aggregated, and analyzed in those beautiful dashboards. Whenever I explained it to friends, I sounded like a podcast ad.

Depending on the metadata, users’ actions could be scrutinized down to the bone, at the most granular level imaginable. Data could be segmented by anything an app collected—age, gender, political affiliation, hair color, dietary restrictions, body weight, income bracket, favorite movies, education, kinks, proclivities—plus some IP-based defaults, like country, city, cell phone carrier, device type, and a unique device identification code. If women in Boise were using an exercise app primarily between the hours of nine and eleven in the morning—only once a month, mostly on Sunday, and for an average of twenty-nine minutes—the software could know. If people on a dating website were messaging everyone within walking distance who practiced yoga, trimmed their pubic hair, and were usually monogamous but looking for a threesome during a stint in New Orleans, the software could know that, too. All customers had to do was run a report; all they had to do was ask.

We also offered a secondary product, a people-analytics tool, for which some customers paid extra. The people-analytics tool stored individual profiles of users on those customers’ platforms. These contained streams of personalized, searchable activity, as well as any identifying metadata. The point of this tool was to facilitate outreach based on behavior, and incentivize re-engagement. An e-commerce store could search its own database to see which men, exactly, were filling online shopping carts with razor blades and beard oil but never checking out, and send those men an email, offering discounts or simply a passive-aggressive reminder that it might be time to shave. A food-delivery app, upon registering that a user had ordered a paleo TV tray six nights in a row, might trigger an in-app pop-up suggesting she try a carbohydrate. An exercise app could identify that a user had stopped a workout at the burpee section and automatically send a push notification asking him if he was still alive.

The tool was free to use to a certain threshold, after which data was metered. If our customer companies acquired more users of their own, their volume of data would increase, and their monthly invoices would spike accordingly. This meant the tool was inherently lucrative, because every company wanted to grow. The underlying assumption was that if our customers were bringing on more users, they should also be bringing in more money; that revenue and usage were linked.

This turned out to be generous. Many startups didn’t have a revenue model to begin with, optimizing instead for market penetration. In these cases, venture capital served as a placeholder for profit: companies acquired more users without bringing in more money, as if they were simply an intermediary between us and their investors’ bank accounts. Our payment structure was straightforward, simple, canny. It would have been logical, too, if logic—or basic economics—had any governance over the venture-backed ecosystem.

To do my job effectively, I had to be able to see customers’ code, as well as their dashboards. This was true of anyone in a customer-facing role; it was almost impossible to solve users’ problems if the problems weren’t in front of us. The simplest way for the analytics startup to achieve this was by granting those of us on the Solutions team access to all of our customers’ data sets: to see the tool as if we were logged in to any given user’s account, to experience our product through their eyes.

Some called this setting God Mode. It wasn’t our customers’ payment, contact, and organizational information—though we could see that, too, if we needed to—but the actual data sets that they collected on their own users. This was a privileged vantage point from which to observe the tech industry, and we tried not to talk about it. “We’re not just selling jeans to miners,” Noah said. “We’re doing everyone’s laundry.”

God Mode was a business education. Engagement metrics could tell the story of a startup’s entire life span. Startups rumored to be rocket ships sputtered to get off the ground. Gaming apps spiked and flamed out within weeks. The descent into obsolescence was almost always broken by cushions of venture capital, but we could see the direction things would go.

We all knew that internal permissions, limiting what we could see of customer data sets, would come eventually. We also knew, at least for the time being, that it wasn’t a priority for our Engineering team. This level of employee access was normal for the industry—common for small, new startups whose engineers were overextended. Employees at ride-sharing startups, I’d heard, could search customers’ ride histories, tracking the travel patterns of celebrities and politicians. Even the social network everyone hated had its own version of God Mode: early employees had been granted access to users’ private activity and passwords. Permissioning was effectively a rite of passage. It was a concession to the demands of growth.

Besides, early employees were trusted like family. It was assumed we would only look at our customers’ data sets out of necessity, and only when requested by customers themselves; that we would not, under any circumstances, look up individual profiles of our lovers and family members and coworkers in the data sets belonging to dating apps and shopping services and fitness trackers and travel sites. We would not, out of sociological curiosity, surf through data sets of neighborhood-watch platforms and online programs for Christian men trying to kick their masturbation habits. We would not pry.

It was assumed that we wouldn’t check back on past employers to see how they were faring without us. It was assumed we would never discuss the glaring inconsistencies between the public narratives spun around our startup customers and the stories that their data told: if we were to read breathless, frothy tech-blog coverage about companies we suspected were failing, we would only smile and close the tab. It was assumed that if we had a publicly traded company using our software—and, if so moved, could chart the overall health of that public company based on its data set, or build out predictive models of when its overall value might grow or recede—we would resist buying or selling its stock.

Our tiny company of twentysomethings operated on good faith. If good faith failed, there was a thorough audit log of all employee behavior: the founders had implemented a product on our own back end, which tracked the customer data sets we looked at and the specific reports we ran. But nobody ever used the words “insider trading.” Nobody had a press contact. There was no policy on leaks. Not that we needed one—we were all, as the CEO liked to remind us, Down for the Cause.

San Francisco was an underdog city struggling to absorb an influx of aspiring alphas. It had long been a haven for hippies and queers, artists and activists, Burners and leather daddies, the disenfranchised and the weird. It also had a historically corrupt government, and a housing market built atop racist urban-renewal policies—real estate values had benefited as much from redlining as from discriminatory zoning practices and midcentury internment camps—but these narratives, along with the reality that an entire generation had been prematurely lost to AIDS, undercut its reputation as a mecca for the free and freakish, people on the fringe. The city, trapped in nostalgia for its own mythology, stuck in a hallucination of a halcyon past, had not quite caught up to the newfound momentum of tech’s dark triad: capital, power, and a bland, overcorrected, heterosexual masculinity.

It was a strange place for young and moneyed futurists. In the absence of vibrant cultural institutions, the pleasure center of the industry might have just been exercise: people courted the sublime on trail runs and day hikes, glamped in Marin and rented chalets in Tahoe. They dressed for work as if embarking on an alpine expedition: high-performance down jackets and foul-weather shells, backpacks with decorative carabiners. They looked ready to gather kindling and build a lean-to, not make sales calls and open pull-requests from climate-controlled open-plan offices. They looked in costume to LARP their weekend selves.

The culture these inhabitants sought and fostered was lifestyle. They engaged with their new home by rating it. Crowdsourced reviewing apps provided opportunities to assign anything a grade: dim sum, playgrounds, hiking trails. Founders went out to eat and confirmed that the food tasted exactly how other reviewers promised it would; they posted redundant photographs of plated appetizers and meticulous restaurant-scapes. They pursued authenticity without realizing that the most authentic thing about the city was, at this moment in time, them.

The city’s passive-aggressive, progressive, permissive politics tended to rankle transplants, but tech’s self-appointed representatives weren’t for everyone, either. Every three months a different engineer or aspiring entrepreneur, new to the city, would post a screed on a blogging platform with no revenue model. He would excoriate the poor for clinging to rent control and driving up condo prices, or excoriate the tent cities by the freeway for being an eyesore. He would suggest monetizing homeless people by turning them into Wi-Fi hotspots. He would lambaste the weak local sports teams, the abundance of bicyclists, the fog. Like a woman who is constantly PMSing, a twenty-three-year-old founder of a crowdfunding platform wrote about the climate. The extension of casual misogyny to weather was creative, but the digital ambassadors didn’t seem to like actual women, either: they whined that the women in San Francisco were fives, not tens, and whined that there weren’t enough of them.

Like most of the larger, older, serious hardware corporations, the major internet upstarts had hunkered down on the suburban Peninsula, thirty miles south. Their campuses offered candy stores and rock-climbing gyms, bike-repair shops and doctors’ offices, gourmet cafeterias and hair salons, nutritionists and day cares. They offered no reason to ever leave. The campuses were accessible by public transportation, but public transportation did not offer Wi-Fi. Every weekday, private shuttles looped through the city’s residential neighborhoods, pausing at public bus stops to pick up commuters.

The commuters wore corporate identification badges clipped to their belt loops or draped on top of their jackets, like children trying not to get lost in a mall. They stood in line for the shuttles with their backpacks and reusable coffee cups; some slung bags of dirty laundry over their shoulders. They looked tired, resigned, sheepish. Mostly, they looked at their phones.

Transplanted startup workers bemoaned the transit infrastructure, an old system riddled with inefficiencies that shut down almost entirely at midnight—not that anyone making a midlevel tech salary was taking the bus. A glut of transportation apps had sprung up to replace San Francisco’s poky streetcars and unreliable taxi fleet. The largest was an on-demand ride-sharing startup, a company committed to domination at all costs, including profitability.

The ride-sharing startup’s main competitor had a near-identical business model but much cuter branding. The cute competitor required its drivers—contract laborers commandeering their own personal vehicles—to hook large fuchsia mustaches, made of synthetic fur, to their grilles and greet passengers with a fist bump. Improbably, this worked. The company knew its audience: San Franciscans, living in neighborhoods where every other storefront had a pun in its name, were corny.

I abandoned my expectations for how cities should be. Bars and cafés opened late and closed early; traffic seemed to slide backward, downhill. The city dealt in improbable couplings. A pay-as-you-wish yoga studio shared a creaky walk-up with the headquarters of an encrypted-communications platform. A bodega selling loosies sat below an anarchistic hacker space. The older office buildings, regal and unkempt with marble floors and peeling paint, housed orthodontists and rare-book dealers alongside four-person companies trying to gamify human resources or commoditize meditation. Data scientists smoked weed in Dolores Park with Hula-Hoopers and blissed-out suburban teenagers. The independent movie theaters played ads for networked appliances and B2B software before projecting seventies cult classics. Even racks at the dry cleaner suggested a city in transition: starched police uniforms and synthetic neon furs, sheathed in plastic, hung beside custom-made suits and machine-washable pullovers.

Homeless encampments sprouted in the shadows of luxury developments. People slept and shat and shot up in the train stations, lying beneath advertisements for fast fashion and productivity apps, as waves of commuters stepped delicately around them. I woke up one morning to the sound of someone howling for mercy on the corner of my block: a woman screaming bloody murder, dragging one leg, wearing nothing but a torn T-shirt emblazoned with the logo for a multinational consumer-electronics company.

This concentration of public pain was new to me, unsettling. I had never seen such a shameful juxtaposition of blatant suffering and affluent idealism. It was a well-publicized disparity, but one I had underestimated. As a New Yorker, I had thought I was prepared. I thought I’d seen it all. I felt humbled and naïve—and guilty, all the time.

I moved into an apartment in the Castro, joining a man and a woman in their late twenties, roommates who had wiggled their way onto a hand-me-down lease. They were tech workers, too. The woman worked as a midlevel product manager at the social network everyone hated; the man as a data scientist at a struggling solar-energy startup. They were both endurance runners; the data scientist kept a road bike in his bedroom. They had no body fat. They had no art in the apartment, either. On the refrigerator was an impressive collection of novelty magnets arranged in a perfect grid.

The apartment was gigantic, a duplex with two living rooms and a view of the bay. Both roommates claimed they wanted to live independently but couldn’t abandon the rent control. With a combined household income that easily topped four hundred thousand dollars—not including the product manager’s stock—we were not people for whom rent control was intended, but there we were. When I signed a sublease in exchange for the keys, my new roommates congratulated me on my good luck.

I got along better with the product manager, though we occupied different spaces: I was in the startup world, land of perpetual youth, and she was an adult like any other, navigating a corporation, acting the part, negotiating for her place. She was classically trained in violin and collected leather-bound antique books, like a Chekhov character. I felt uncultured by comparison, with my colorful contemporary paperbacks and penchant for overwrought indie rock. She seemed to find me amusing, maybe a little pitiable. I admired and did not understand her. Mostly, we talked about exercise.

The bedroom I sublet had an air mattress and a fire escape. One by one, I moved my boxes out of the startup’s supply closet. I stacked the books on the floor, unrolled a camping blanket onto the bed, hung my blouses and wrap dresses in the closet. My clothes looked like they belonged to someone else, probably because they did. After a few weeks, I folded them back up and sent them to a publishing friend in New York, who still dressed up for the other women in her office.

The fire escape offered a private passage to the roof, and from time to time I would climb up to take stock. I would gaze out over the pastel Victorians, the rustling magnolia trees, the fog rushing over the hills, the container ships skimming the bay. Every so often, I felt a wave of affection for San Francisco, a thrill like hope—a sense, however small, that it could eventually become home.

When the product manager turned thirty, she hosted a wine and cheese party at our apartment. The data scientist and I were invited. I marked it on my calendar, as if I would forget.

The product manager’s friends arrived promptly, in cocktail attire. She was intimidating in black silk. Hundreds of dollars’ worth of cheese had been procured, and classical music streamed through the house. A man opened a bottle of champagne, which he reassured us was from France. People clapped when the cork popped.

Feeling like a child at my parents’ party, I sent myself to my room, locked the door, and changed out of work clothes—baggy sweater, high-waisted jeans—and into a very tight dress. I had gained five, eight, ten pounds in trail mix. When I reentered the living room, I sucked in my stomach and slid between people’s backs, looking for a conversation. On the couch, two men in suit jackets expounded on opportunities in cannabis. Everyone seemed very comfortable and nobody talked to me. They tilted their wineglasses at the correct angle; they dusted crumbs off their palms with grace. The word I heard the most was “revenue.” Maybe “strategy.”

This was the nascent neomillionaire class, I realized. They weren’t all rich, not yet, but they were right on track. My coworkers were also aspiring, but they had a different style. Not one of them would be caught dead wearing a tailored suit to a house party.

I wound up on the roof with a cluster of men. In the distance was the tip of the famous rainbow flag on Castro Street, whipping. I felt a twist of homesickness, the jolt of being three thousand miles away from my mother.

“We’re looking to buy in Oakland,” one of the men was saying.

“Too dangerous,” said another. “My wife would never go for it.”

“Of course not,” replied the first, absently swirling his wine. “But you don’t buy to live there.”

By the time the last guest filtered out, I was already in leggings and a sweatshirt, half-drunk and cleaning: scooping up cheese rinds, rinsing plastic glasses, sneaking slices of chocolate cake with damp hands. The product manager came to say good night, and she was beautiful: tipsy but not toasted, radiant with absorbed goodwill. She repaired to her room with her boyfriend. From down the hall, I could hear them as they quietly undressed, eased into bed, and turned over into sleep.

Most nights, I worked late. The neighborhood around the office emptied out after dark. An off-price department store glowed on the corner. Men in shredded pants shuffled in front of the train station, shouting down nobody.

I downloaded the ride-sharing apps that everyone had said I would want, but which I had resisted. I found the premise creepy: I had never wanted to get into strangers’ cars, hated hitchhiking, had been told my entire life never to do so. Being chauffeured by other adults in their own vehicles didn’t seem luxurious to me, it looked like carpooling. Carpooling, however, was meant to be a social good with an environmental benefit. It seemed cynical and backward to pay a private company to brute-force carpooling by putting more cars on the road.

But the buses had delays and broke down; the light rail back to the Castro came every forty minutes. A car, by contrast, was a tunnel to home. I found myself ducking into strangers’ sedans on a nightly basis, meekly extending my fist for a tap, chattering on mindlessly from the back seat. Clutching my keys, crossing my fingers.

As part of the onboarding process, the operations manager set me up on lunch dates with coworkers from across the company. I went out with an account manager whose desk faced mine in the cluster. He often air-golfed, perfecting his swing, while on the phone with customers. He called the Mission “the Mish,” but I liked him a lot. He was easy to talk to; he was easy to talk to for a living.

The account manager and I procured large, sloppy sandwiches and sat down in a plaza between two hotels. We gazed out at the underdressed tourists. I asked how he had chosen to work at the analytics startup—he’d studied history, after all. It wasn’t a major I associated with upselling. “Come on,” he said. “I heard there were a bunch of twentysomethings crushing it in the Valley. How often does that happen?”

Relatively often, I had assumed. The plaza was full of people who looked just like us: white and young and exhausted, coasting on caffeine and simple carbohydrates. The previous year, a thirteen-person startup, the maker of a photo-sharing app, had been acquired for a billion dollars by the social network everyone hated. Their office was three blocks away. “This is a get-rich-quick scheme,” the account manager said. “We built a tool that’s, what, five, ten years in the future? Nobody has ever seen something like this before. The product practically sells itself.”

I had not fully grasped how rare the analytics startup was. Ninety-five percent of startups tanked. We weren’t just beating the odds; we were soaring past them. This was what everyone who trekked out to the Bay Area wanted, but it was not actually supposed to happen. The CEO of the e-book startup had been right: the analytics startup was a rocket ship. Despite its size and age, the company was already well regarded and legitimate, marked to become a unicorn. We were hurtling toward a billion-dollar valuation. Our revenue soared every month. We were winning, and we would be rich.

“This company is going to be worth a gajillion dollars,” the account manager said, taking a bite of potato salad. “We’re ripping up and to the right. We have the best and the brightest. We’re on an immutable path toward success. We’re all just fucking ready to give whatever needs to be given to make this thing happen. All anyone is asking is for us to pour our hearts and souls into this unstoppable behemoth.” He drained his iced coffee. “Frankly,” he said, “I think it’s a pretty good bargain.”

I went on another arranged lunch, with the CTO. We had never spoken; I didn’t know what to expect. According to my teammates, the CTO was brilliant and difficult. An autodidact, he hadn’t graduated high school, but he could single-handedly design the sort of complex database infrastructure that, elsewhere, would have taken a team of experienced computer scientists. I didn’t know whether this was hyperbolic, but it didn’t matter: he was the only employee to whom the founders deferred. This wasn’t just programmer supremacy, despite its popularity. He was the only one who really understood the core technology. The company wouldn’t exist without him.

The CTO was in his early thirties, with untended facial stubble and beautiful, wide-set eyes. He often smelled like menthols. While the other engineers had condos in the Marina or renovated Victorian apartments lining Dolores Park, he lived in the Tenderloin, a high-crime neighborhood with a concentration of SROs and open-air drug markets—on purpose, Noah had once said, eyebrows raised in admiration. The CTO shuffled into the office every afternoon with headphones on, holding a paper cup of coffee and avoiding eye contact. He almost always wore a T-shirt with the company logo on it and an unbranded navy-blue hoodie.

We ordered salads at a faux-French café in the financial district and sat at a rickety table outside, watching the midday stream of men with briefcases and women in shift dresses. They looked so much older than we did, in their inoffensive textiles and fake alligator loafers. They looked straight out of another era, like the nineties. I wondered how we looked to them: two round-cheeked slobs in T-shirts and sneakers, eating slices of grilled chicken like teenage miscreants with a stolen credit card. I nudged my backpack under the table, out of view.

My coworkers had warned me that the CTO was inscrutable and reticent, but after a few minutes I wondered how hard any of them had tried. I was surprised to find that he had a dark, sarcastic sense of humor. We had more in common than I would have guessed: compulsive reading habits; insomnia. While I usually spent sleepless nights staring at the ceiling and worrying about my loved ones’ mortality, he worked on programming side projects. Sometimes he just passed the time between midnight and noon playing a long-haul trucking simulator. It was calming, he said. There was a digital CB radio through which he could communicate with other players. I pictured him whispering into it in the dark.

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.

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