Uncanny Valley

Introduction

Anna Wiener's memoir "Uncanny Valley" offers a candid, insightful look into the world of Silicon Valley tech startups through the eyes of a young millennial woman. As someone who transitioned from the struggling New York publishing industry to the lucrative tech scene in San Francisco, Wiener provides a unique perspective as both an insider and outsider in this influential but often problematic world.

The book follows Wiener's journey over several years as she works for three different tech companies, from a small e-book startup to larger data analytics and open-source software firms. Along the way, she grapples with the appeal and disillusionment of startup culture, sexism in tech, surveillance capitalism, and her own ambitions and values. "Uncanny Valley" serves as both a coming-of-age story and a critical examination of an industry that has reshaped modern society.

Leaving Publishing for the Promise of Tech

The Struggling Publishing Industry

When we first meet Anna, she is working as an assistant at a literary agency in New York City. Like many millennials with humanities degrees in the aftermath of the 2008 financial crisis, she finds herself in a precarious position:

• The publishing industry is struggling financially and offers little job security or room for advancement
• Most entry-level publishing jobs require a secondary source of income to make ends meet
• There's always a fresh crop of idealistic graduates willing to work for even less

Meanwhile, Anna watches as people her age in Silicon Valley are starting companies and making millions. She feels stuck and unfulfilled, wanting to make more money and find meaningful work.

The Allure of a Publishing Startup

Anna's interest is piqued when she reads about an e-book startup that has raised $3 million in funding. Though this is a relatively small amount by tech standards, to Anna it seems impressive. She's drawn to:

• The founders' confidence and ambition
• The promise of doing impactful work related to books
• The excitement of joining a small team where her contributions would matter

She applies and is offered a 3-month trial position. At first, the job feels thrilling. Anna has expertise in books for the first time in her career. But cracks soon begin to show:

• The founders don't seem to actually care much about literature
• The app seems designed more for signaling that one is a reader rather than for actual readers
• Anna lacks the brash confidence and entitlement of the founders

When the CEO accidentally reveals he thinks Anna is "too interested in learning, not doing," it's clear the job isn't a good fit. But this taste of the tech world has whetted Anna's appetite for more.

Moving to San Francisco

A City Transformed by Tech

When Anna arrives in San Francisco for a job interview, she finds a city already being reshaped by the tech industry:

• Rents are skyrocketing, pushing out artists and longtime residents
• Corporate-branded Pride parades feel sanitized and commercialized
• The creative types Anna befriended in New York are being priced out

She feels like a trespasser as she rents a room through Airbnb from a couple living in their own basement. The city's transformation foreshadows Anna's own impending changes.

A Bizarre Interview Process

Anna's interview at a mobile analytics startup gives her a crash course in Silicon Valley culture:

• Her professional attire makes her feel out of place among employees dressed in outdoor gear
• She's subjected to hours of brain teasers and estimation questions
• The technical co-founder makes her take a law school entrance exam

Anna realizes that in tech, qualifications are less important than "hustle" and cultural fit. She gets the job not because of her (non-existent) background in data analytics, but because she scores perfectly on the exam portion.

The $65,000 starting salary seems like a fortune compared to publishing wages. Anna feels professionally desirable for the first time, which outweighs her concerns about "selling out."

Early Days at the Analytics Startup

Drinking the Kool-Aid

At first, Anna enthusiastically embraces startup culture:

• She learns basic coding and feels empowered fixing customers' problems
• For the first time, she's not responsible for making anyone coffee
• She's proud when she sees strangers wearing the company t-shirt
• She adopts the unofficial tech uniform of flannel and work boots

The company is making money, and Anna is doing well within it. She befriends the CTO and is told she has leadership potential.

God Mode and Privacy Concerns

Anna gains access to customers' internal data through what's called "God Mode." This raises some ethical questions:

• No one seems worried about user privacy
• She hears about engineers at other companies tracking celebrities' movements
• There's potential for insider trading based on companies' internal metrics

But in the heady atmosphere of the growing startup, Anna mostly brushes these concerns aside.

Cultural Shifts

As she settles into San Francisco tech life, Anna notices changes in herself:

• She moves into an apartment with other tech workers, feeling guilty about taking advantage of rent control
• She struggles to connect with non-tech locals, finding their interests in things like Reiki too "hippie"
• She becomes more motivated by money and obsessed with analytics

Anna starts to feel caught between two worlds, no longer fitting in with her old artist friends but not fully at home in tech either.

Cracks in the Facade

Toxic Leadership

As time goes on, Anna starts to see problems with the company culture:

• The CEO can be cruel and petty, sometimes giving employees the silent treatment
• He refuses to give positive feedback, saying that's what salaries are for
• When an employee asks for changes during a review, he's summarily fired

Rampant Sexism

The gender imbalance and casual misogyny in the office become impossible to ignore:

• Only 8 out of 60 employees are women
• A colleague keeps a ranked list of female coworkers by attractiveness
• A new hire makes inappropriate comments about "sensual Jewish women"
• Management brushes off complaints, saying "that's just who he is"

Moral Qualms

Anna starts to grapple with the ethics of what they're doing:

• She realizes they're essentially a surveillance company
• No one discusses the implications of the Snowden revelations
• She questions whether they're really making the world better

These doubts lead Anna to quit her job at the analytics startup. But she's not ready to give up on tech altogether.

A New Start-Up with Hacker Ethos

Initial Enthusiasm

Anna takes a job at an open-source software company that seems more aligned with her values:

• It has a countercultural, techno-utopian ethos
• There's a flat hierarchy and formerly had a "name your own salary" policy
• The tacky office decor reflects a playful hacker culture

Despite some red flags - like a recent gender discrimination scandal and a pay cut - Anna is optimistic about helping create a healthier company culture.

Disillusionment Sets In

However, Anna soon encounters familiar problems:

• The company is slow to address harassment of women using their platform
• The lack of hierarchy actually magnifies inequality, with those closest to the CEO wielding unofficial power
• Flexible work policies lead to isolation, with Anna rarely interacting with colleagues in person

Alienation and Malaise

Anna finds herself increasingly disconnected from her work and questioning her choices:

• Her job requires little actual work but lots of aimless internet scrolling
• She feels ashamed earning so much more than friends doing meaningful creative work
• But she's too attached to her salary and benefits to pursue personal goals
• She notices similar malaise among peers who feel disconnected from their abstract work

A trip home to New York throws these feelings into sharp relief, making Anna realize how much she's changed and compromised herself for her tech career.

The Dark Side of Tech

Normalizing Surveillance

Anna becomes uncomfortably aware of how the tech industry has normalized invasive data collection:

• A friend outside tech is shocked to discover his phone tracking his movements
• Anna realizes she and her colleagues failed the moral test posed by the NSA revelations years earlier
• They've helped create massive private databases of human behavior

Hate and Extremism

At work, Anna confronts the ugly side of open platforms:

• Far-right groups use the company's software to organize
• Death threats and anti-Semitic content proliferate
• The company's response is weak, limited to polite requests to tone things down

Wealth Inequality

The stark contrast between tech wealth and San Francisco's housing crisis becomes impossible to ignore:

• Homeless people in tech company t-shirts defecate on the streets
• Each new IPO brings 20-somethings bidding huge amounts on million-dollar homes
• Well-funded startups "reinvent" communal living while poorer residents are evicted from similar setups

Anna realizes the tech world is arguing passionately about an alternate reality while ignoring real-world problems. She longs to reconnect with the actual world.

Finding Her Own Path

Valuing Different Skills

Anna finally recognizes that she's internalized tech's narrow definition of valuable skills:

• She's repressed her empathy and emotional intelligence to fit in
• These "soft skills" are undervalued in the industry but actually crucial
• Her boyfriend helps her see that she has strengths her tech colleagues lack

Moral Awakening

Late in her time at the open-source company, Anna encounters a whistleblower who leaked documents exposing illegal activity by the wealthy. This gives her hope that some in tech are developing moral misgivings about the industry's direction.

Moving On

After over three years, Anna quits her job to write full-time:

• She exercises her stock options, making about $200,000 when the company is acquired
• But she views this windfall as a "conflict diamond" - valuable but ethically tainted
• She's ready to find more meaningful work aligned with her values

Key Themes and Insights

The Seductive Pull of Tech

Wiener's memoir vividly illustrates why so many talented young people are drawn to the tech industry:

• The promise of making an impact and changing the world
• Astronomical salaries and valuable stock options
• A sense of being at the center of innovation
• Casual workplaces with abundant perks

For millennials struggling in other industries, tech can seem like a ticket to financial stability and an exciting career. Wiener shows how seductive this narrative can be, even for those without technical backgrounds.

Silicon Valley's Reality Distortion Field

However, Wiener also reveals how the tech bubble warps people's perspectives:

• There's a tendency to see every problem as solvable through technology
• Ethical concerns are often brushed aside in pursuit of growth and disruption
• The industry's wealth creates a stark disconnect from normal economic realities
• An insular culture breeds arrogance and disdain for outsiders

Living inside this "reality distortion field" makes it hard for many in tech to see the real-world impacts and problems their work creates.

The Costs of Startup Culture

While startup culture is often glorified, Wiener exposes its darker side:

• Lack of work-life balance and pressure to always be "hustling"
• Ageism that favors young workers willing to burn themselves out
• Rampant sexism and lack of diversity
• Toxic leadership styles enabled by lack of oversight
• Prioritizing growth over ethics or user wellbeing

She shows how the "move fast and break things" mentality can lead to broken lives and communities.

Data Privacy and Surveillance Capitalism

A major theme is the casual attitude toward user data in the tech world:

• Companies collect vast amounts of personal information with little oversight
• Employees often have broad access to sensitive user data
• The implications of building massive behavioral databases are rarely considered
• Users are mostly unaware of how much they're being tracked

Wiener's insider perspective reveals how normalized surveillance has become in Silicon Valley.

Gender Dynamics in Tech

As a woman in a male-dominated industry, Wiener provides insight into tech's gender problems:

• Casual sexism and "bro culture" are pervasive
• Women are often relegated to non-technical roles
• Those who speak up face retaliation or being labeled as difficult
• Attempts at diversity often feel superficial or misguided

Her experiences highlight why the tech industry struggles to retain women and other underrepresented groups.

The Ethics of Technology

Throughout the book, Wiener grapples with the moral implications of her work:

• The potential for technology to be used for surveillance or oppression
• How "disruption" often means eroding labor protections or community stability
• The industry's role in exacerbating inequality
• Tech's tendency to try to "solve" complex social issues without understanding them

She raises important questions about the responsibilities of those building influential technologies.

Finding Meaning in Work

Ultimately, Wiener's journey is about reconciling her values with her career ambitions:

• Learning to value her non-technical skills and perspectives
• Questioning whether financial success is worth compromising her ethics
• Seeking work that feels meaningful beyond just making money
• Reconnecting with the real world outside the tech bubble

Her story will resonate with many struggling to find purpose in their careers.

Writing Style and Structure

Wiener's writing style in "Uncanny Valley" is sharp, witty, and often darkly funny. She has a keen eye for the absurdities and contradictions of startup culture, capturing them in memorable descriptions and turns of phrase.

The memoir is largely chronological, following Wiener's journey from New York publishing to various San Francisco startups. However, she weaves in broader observations about tech culture and her own personal growth throughout.

Notably, Wiener rarely names specific companies or individuals, instead using descriptions like "the social network everyone hated" or "the search engine giant." This creates a sense of archetypes that could apply to many Silicon Valley firms while protecting identities.

The book's title, "Uncanny Valley," refers to the unsettling feeling caused by things that seem almost but not quite human. It's an apt metaphor for Wiener's experience in tech - a world that promises utopia but feels increasingly artificial and disturbing the closer you look.

Impact and Reception

"Uncanny Valley" was published in 2020 to widespread critical acclaim. It was named a New York Times Notable Book and appeared on numerous "Best of the Year" lists.

The memoir resonated strongly with many readers, particularly millennials who had their own experiences with startup culture or who watched the tech industry reshape society from afar. It gave voice to a growing sense of unease about Silicon Valley's outsized influence.

For those outside the tech world, the book provided an accessible window into startup culture and the mindset driving many influential companies. Wiener's status as both insider and outsider allows her to explain industry jargon and norms while maintaining a critical perspective.

The book also sparked important conversations about ethics in tech, workplace culture, and the need for more diverse voices in shaping the technologies that increasingly govern our lives.

Some in the tech industry criticized Wiener for painting an overly negative picture or for her own complicity in the problems she describes. However, many praised her honesty in wrestling with these complex issues.

Conclusion

"Uncanny Valley" is a timely and thought-provoking memoir that offers valuable insight into one of the most powerful and controversial industries shaping the modern world. Through her personal journey, Anna Wiener illuminates larger truths about technology, capitalism, gender dynamics, and the search for meaning in one's work.

The book serves as both a cautionary tale about the seductions and pitfalls of startup culture and a call for more ethical, humane approaches to innovation. Wiener's story highlights the need for diverse perspectives in tech and the importance of questioning the industry's assumptions and values.

Ultimately, "Uncanny Valley" is a coming-of-age story for an entire generation grappling with the promises and perils of the digital age. It challenges readers to think critically about their relationship with technology and the kind of future we want to build.

As the tech industry continues to wield enormous influence over our economy, politics, and daily lives, voices like Wiener's are crucial in fostering nuanced discussions about its impacts. "Uncanny Valley" makes an important contribution to ongoing debates about how to harness the potential of technology while mitigating its harms.

For anyone interested in startup culture, Silicon Valley, or the broader effects of the tech industry on society, "Uncanny Valley" offers an engaging, insightful, and timely read. It's a memoir that captures a pivotal moment in the digital revolution while raising essential questions that will shape our collective future.