Uncanny Valley

Uncanny Valley
Author: Anna Wiener
Publisher: MCD
Published: 1/14/2020
In her mid-twenties, at the height of tech industry idealism, Anna Wiener—stuck, broke, and looking for meaning in her work, like any good millennial--left a job in book publishing for the promise of the new digital economy. She moved from New York to San Francisco, where she landed at a big-data startup in the heart of the Silicon Valley bubble.


Book Summary - Uncanny Valley by Anna Weiner

Key Insights

Uncanny Valley follows Anna Weiner in her transition from the New York publishing industry to the Silicon Valley tech world. The literary outsider, drawn in by the allure of economic prospects, works for several start-ups and slowly finds herself growing disillusioned with the tech world, witnessing up-close the questionable morality of things like mass data collection and toxic work culture. Ultimately, the book asks us to all consider the long term implications of tech work and what’s compromised when we uncritically buy into its worldview.

Key Points

In 2013, 20-something Anna Weiner found her dreams stalling when New York publishing jobs were drying up.

Anna begins the book at a crossroads. She’s been chasing a career in publishing, the dream of a life surrounded by literature in the glamorous New York City. But she starts to wonder if this dream is at all realistic— she’s been stringing together a small income from freelancing and assisting at a boutique literary agency, but barely enough to live on.

The other people she knows with similar dreams, a class of entry-level publishing assistants, are also struggling with the tiny income, taking second night time jobs as bartenders and copywriters. Worse yet, a hoard of well-to-do young people was working for nothing at all, living off of their wealthy parents and trust funds. There was always someone willing to work for less, says Anna, and always someone more enthusiastic.

Meanwhile, on the other side of the country, a new industry was starting to cause waves. Anna read stories about people her age, students just out of college, starting their first companies (“a social network everyone hated”, for example) and quickly making millions. Jobs sprang up everywhere, and these companies started to make their way into everyone’s lives. Other companies, such as “an online superstore which started off selling books” and then grew into a ruthlessly efficient giant, were stealing sales from older industries like publishing.

In a way, Anna felt inspired by this 21st-century gold rush. One day, hungover and eating a salad at her desk, she comes across an article for a publishing start-up that raised three million dollars in funding, an eye-popping number for Anna. In the photo, two young cofounders posed confidently. The start-up promised to revolutionize book publishing. Quietly, Anna applied.

Anna takes a job with a publishing start-up thrilled by the salary and the mission, but soon finds it wasn’t what it seemed.

Anna was invited for an interview with the company and felt relieved to find that the founders weren’t as nerdy as she expected. They chatted about the mission, and Anna happily accepted a three-month contract to curate book titles for the company, also writing copy for their website.

The small team of five worked out of a New York office, and Anna felt thrilled to be there and certainly feeling more useful than she did at the agency. As the resident book expert, she didn’t mind that she had to fetch snacks for the founders occasionally.

But quickly, cracks started to show in the startup’s façade. Anna’s friends pointed out that the company may not be as great for the publishing industry as they claimed, and Anna started to notice these signs too. For one, the founders ignored her attempts to start a company book club and misspelled the names of legendary authors in their materials. She felt uncomfortable when they started referring to the company as a “lifestyle company”, selling people a way to seem like they were reading.

During the day, she often found herself with no roadmap and learned that in early start-ups you were supposed to invent your job as you went, confidently putting yourself in charge of new projects. Anna felt lost— she hadn’t signed up for such an open-ended role. The last straw came when one day, the CEO wrote in the company group chat, “she’s too interested in learning, not doing”, having intended it for the other founders. Anna knew it was time to leave.

When Anna moves to San Francisco, she finds the already established culture to be difficult for outsiders and locals alike.

Despite a first clumsy brush with the tech world, Anna still felt the comforting sense of security and promise offered by a career in tech. Packing up her apartment in Brooklyn, she thinks about how she’s always felt like a contradiction: drawn to order and stability but also a creative and free life. She decided that she wanted to bet on her stable side. To find her next job, she knew she had to move to San Francisco, the center of the technology boom. She packed her things and flew across the country.

She found herself staying in a couple’s home using a “millennial-friendly platform for renting stranger’s bedrooms”. The couple lived in their basement and rented out their home. Anna felt strange in the home, nervous to use their things or sit on their furniture.

She interviewed for a “mobile analytics start-up” and immediately felt out of place when she walked in wearing her fancy interview clothes and was embarrassed to see that everyone else dressed as they’d just gotten back from the rock climbing gym.

During the interview, she was asked to answer bizarre questions like “how would you explain the internet to a medieval farmer?” and made to fill out a portion of a law school entrance exam while the interviewer checked his phone. Later, she learned that these sorts of interviews were common in Silicon Valley, designed to determine if she was determined or cheerful enough to comply with company culture.

Anna landed the job, to her surprise, because she’d gotten a perfect score on the law exam. She was given a salary of $65,000 with benefits, a salary that would’ve been unheard of in New York publishing. The thrill of this salary and the nice feeling of being employable eclipsed any guilt about selling out.

Anna switches to a new company and finds everything easier when she adopts the interests of her co-workers.

Anna’s new gig was at a Big Data company, which collected mobile data, analyzed it, and distributed it to other companies. She was glad that her jobs no longer involved fetching coffee for executives and she felt truly useful for the first time. The job was to help solve problems for customers by checking their code infrastructure for issues, a practice known as “God Mode” in the industry.

At this time, companies in the tech world didn’t bat an eye at privacy concerns given access to other people’s data. Anna had heard of engineers at other companies (such as a “ride-sharing startup) entering God Mode at their leisure, searching the ride histories of celebrities, friends, and ex-partners. She’d even heard of people using God Mode for insider trading, checking for the internal metrics of companies before buying or selling stocks.

During this time, she moved in with two other tech workers into a rent-control apartment. Her roommates made hilariously high salaries, and Anna began to notice the questionable housing decisions of overpaid tech workers. Surely, rent-controlled apartments weren’t for people like this. She recalls that at a party, she overheard someone saying they were hoping to buy an investment property in a historically black neighborhood in Oakland, a city across the bay from San Francisco. They wouldn’t live there, they added, it’s too dangerous. She grows disquieted, noticing how tech workers were changing their local economies through gentrification and increasing the stratification of income in vulnerable areas.

At work, Anna was doing well. The company was making money, which she realized was exceedingly rare for a start-up. Ninety-five percent of startups fail, a friend tells her over lunch. She befriended people inside the company. Soon enough, she starts to become immersed in the culture. She attends the company’s open house evenings, where industry people and venture capitalists chat in a low lit bar. One evening, the CEO tells her he’d like her to lead her department one day, saying he’d like more women in leadership roles. Anna thinks that a better first step would be to hire more women and change the office culture to make them less uncomfortable.

Later, he tells her he will promote her if she can build a game of checkers with her coding skills. She agonizes over the game for a weekend and eventually learns from a friend that this challenge was nearly impossible for a new coder to achieve.

Anna begins to lean into the tech culture she sees around her. She wears her company t-shirt and flannels over her shoulders. She listens to EDM, a genre she previously couldn’t stand, and takes nutritional supplements. She liked that she could be so laidback at work, as long as she got her job done.

Anna starts to notice that she does not agree with the sorts of popularly-held values in Silicon Valley, like the valuation of hard skills over soft skills, the sexist hiring practices, and the reading of personal data by company employees.

Although in some sense Anna is finally fitting in, she begins to wonder if she adopted these hobbies out of loneliness, and realizes that the only people she sees during her 10-hour workdays are her co-workers. Dating apps are off-limits to Anna, knowing the way that the developers comb through the data of users. She begins to look around San Francisco for friends, maybe people with different interests, but can only seem to find old hippies with interests in things like Reiki and ecstatic dance. Anna can’t seem to enjoy these things either.

In the national news, Edward Snowden reveals that the NSA has been collecting personal information on American citizens. Anna makes the connection to her own company, which also deals with personal information and privacy violation, but this sort of data collection isn’t yet spoken about in the national conversation. Anna becomes uncomfortable with the nature of her work.

As the company grows, Anna notices problems with the hiring process. The founders seem to only hire people who are demographically like themselves— ambitious millennial men. Out of the 60 people at the company, only eight were women, and the sexism in the office was escalating.

Anna also notices the way her company values the technical workers, like the programmers and coders, much more highly than the non-technical workers, like the PR, HR, and customer service departments. One of Anna’s coworkers, who switched from being a public defender to working in tech, heralds complaints from the programmers about the snack stock in the kitchen. Anna notices how during lunch breaks, the technical workers want to talk about computers and stocks, resenting the interests of people like herself.

When Anna is asked to list the five smartest people she knows for recruitment, she hesitates. She thinks of her friends back in New York who valued things like emotions, creativity, and disorder, not just business analytics and productivity. They looked for meaning in their work. She realizes she has changed since coming here, and that her friends likely wouldn’t take a job like this, where the only redeeming quality was the salary.

As Anna finally makes friends, she realizes she needs to leave her company.

Anna helps to organize a movie screening of the CEO’s favorite movie about hackers. During the screening, she looks at him and notices how young he is, still just a kid, and someone who never had a full-time job in his life. She considers his tendency to be vindictive and cruel, refusing to give positive feedback to his teams, and wonders if this is normal.

After talking with several co-workers, she finds a lot of them talked about their relationship with the CEO in therapy, distressed by his behavior towards them. She befriends Noah, a well-liked and friendly employee. Noah has other friends outside of the tech world, back in Berkeley where he lives in an experimental commune, and reminds Anna of her friends in college that were articulate, kind, and could keep a conversation. Later, she meets Noah’s roommate Ian at a party and they begin seeing each other. Anna has finally found people who she can talk to about things other than tech.

But soon, her work life takes a turn for the worse. In a move that shocks the employees, the CEO fires Noah for criticizing the company culture in his annual review. Not only is Anna left friendless in the office again, but a wave of new hires comes with escalated misogyny in the office. One new hire who works alongside Anna rolls his chair over to her and begins to comment on her “sensuality” and “Jewishness”. When she brings it up with her manager, he refuses to do anything about it, saying that this is just the man’s personality. It doesn’t take Anna to realize she cannot stand it anymore. Not only was the culture eroding her self-esteem, but the company itself was essentially a surveillance tool. She leaves the job without regret.

Anna takes a new job with a company that aligns more with her values, but she feels suspicious of their follow through on their promises. Soon, her suspicions are confirmed.

Anna takes her third job in tech at an “open-source” company that sells software to developers. She likes that their office is playfully modeled after the Oval Office, has a flat hierarchy of the management, and their policy of “name your own salary”. At this job, there are no business hours and she has unlimited vacation time. She hopes that this time, the company culture will be different.

Anna reads the backlogs of employee communications in the chat rooms to familiarize herself with the corporate culture and then flies to Chicago to meet with her co-workers. She likes the teammates, but they soon start to complain to her about how the company hasn’t fixed their toxic company culture, despite a recent scandal that exposed their sexist practices. The scandal was brought by a female developer who felt discriminated against by her managers, saying that her work and opinions were often dismissed and that the name-your-own-salary policy had resulted in huge pay gaps.

A few weeks after Anna starts, internet trolls began a harassment campaign against “women in gaming” and started using the open-source startup to organize their abuse and store personal information about the women. After the company disabled their use, Anna spent weeks dealing with the angry death threats of the trolls directed at the support staff. Don’t worry, a colleague told her, no one’s going to drive these children to murder you.

The company’s work from home policy also became alienating, and Anna found herself rarely seeing co-workers face to face. Because her job required long breaks between work, she found herself numbly scrolling through pages and pages of memes and strangers’ pictures. At the end of the day, she would stand up, and only then remember she was in a body at all.

She starts to grapple with the fact that even though she is approaching a six-figure salary, she doesn’t feel she knows how to “do anything”. She misses her old life where she could deal with physical and material things, like books, and hold the product of the work in her hands.

She notices this phenomenon around Silicon Valley too, in the hobbies that became popular with her co-workers. Men began practicing manual labor on the side, woodworking, and making batches of beer in their basements. They must’ve wanted to make something physical too, after hours of working with something that only existed in the cloud.

Visiting her parents back in New York, she realizes how much of herself she’s compromised and how much she’d have to continue to compromise to continue to work in tech.

Anna returns to New York to visit her parents in Brooklyn. She starts clearing out their basement and finds her undergraduate writing and old clothes from college, which make her sentimental. She realizes she’s become so different from the person she used to be. In an effort to feel something, she goes to an experimental dance concert and feels like herself for the first time in years.

As she walks around Brooklyn, she sees that this city has changed too since she left it a few years before. Shiny new high rises and luxury condominiums have popped up, especially by the Brooklyn waterfront where tech companies have started moving. She feels angry at this imposition and experiences for herself what it’s like to have your hometown overrun and rapidly transformed by these industries. Now, she’s a part of the problem in San Francisco.

She meets again with her old friends, who are still doing their underpaid work in creative industries. She feels ashamed at their salary differences and frustrated with herself for getting so wrapped up in money and a desire for health insurance that she let her personal and creative ambitions escape her. But what were her personal goals? She can hardly remember.

She cannot imagine leaving her job at this stage in her life and sees that even her friends from outside of the tech scene have started taking jobs in the industry. Artist friends take up residencies with social-networks and journalists transition to corporate communications. After speaking with her friend Patrick about her ambivalence, he tells her that to work in tech, you have to sacrifice a lot of your values.

Anna realizes the difference between real-world problems and the problems pushed by investors in their own self-interest.

When Anna’s friend freaks out to her that his phone has been saving his frequently visited locations. By now, Anna has grown accustomed to this sort of surveillance and is hardly surprised. Returning home, she feels like a sociopath for finding this normal of companies and reflects on the Snowden revelations. Was tech just ignoring fundamental moral concerns?

At work, another flood of abuse started flooding her company’s support lines. The channels at the company were becoming increasingly flooded with hateful and racist comments. When an alt-right magazine stated that the company was anti-white, death threats came in, once enough to shut down the headquarters. The company hardly responded. She was instructed to use a male avatar to politely ask the abusers to change their anti-Semitic names and remove their racist pictures.

Walking the streets, Anna sees the homeless population growing on the streets. They wear discarded start-up t-shirts and fight for camping spots on street corners where a new tech company’s employees were buying million-dollar homes. Anna considers that while these tech companies claimed to be changing the world, they were only working on things that would make investors money and ignoring structural problems.

For example, Anna read that founders were making communal living spaces around San Francisco, trying to solve the problem of loneliness in the Valley, but were evicting poor people of color to build their buildings.

Who were these companies really helping, thought Anna? She decides that these founders become so obsessed with the world of Silicon Valley that they forget about the problems of the real world.

After understanding her personal values, she leaves Silicon Valley to pursue a full-time writing career.

At a tech-world party with her boyfriend Ian, she complains to him about how she doesn’t feel she has the skills to survive in San Francisco much longer. He reminds her that she’s likely undervaluing the skills that she has, like writing and sensitivity, that are undervalued in tech.

Anna recognizes that she has been undervaluing her own strong-suits, which have been ignored by the tech industry. The founders around her had convinced her that her skills and goals were useless, and were slowly convincing other people around the world too.

She recalls a time when she spoke with a friend who had worked on a project leaking documents exposing the illegal activity of billionaires. Her friend had been the one to lead them. Anna was excited to see that some people in the Valley felt some allegiance to the poor. Still, she quickly learned that this was an exception and that the project of convincing more people to stand up to the arrogant boy’s club of Silicon Valley was too difficult of a project to take on. Maybe, Anna thought, it was time to start valuing her own goals and sense of morality and leave the industry altogether. She decides she wants to be a writer, just as she always dreamed.

Before she quits her job, she buys her stock options. Later that year, the open-source startup is acquired for billions of dollars and many of her friends become millionaires overnight. Anna herself makes a pretty 200,000 dollars before taxes. Anna remembers why she got into it in the first place. The money seems worth it, the work is apparently valuable, but she no longer can believe it is worth the costs.

The Main Take-away

Anna Weiner leaves publishing’s poor economic prospects for the gold rush of Silicon Valley but soon finds their dream to be near-sighted. In all the start-ups she works for she experiences sexism, harassment, and sees the surveillance and toxic internet behavior enabled by their practices. As her salary climbs, she feels troubled that she makes so much for doing something that requires little skill and produces no tangible products. Ultimately, she decides that benefits aren’t worth sacrificing her dream of meaningful work dealing with the real world.

About the Author

Anna Weiner writer for the New Yorker and covers things like startup culture, technology, and Silicon Valley. She also writes for publications like the New Republic, n+1, and The Atlantic. She grew up in Brooklyn and worked for Silicon Valley start-ups for several years. She currently lives in San Francisco.


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