What will I learn about: how major life shifts often begin with a quiet breaking point, and learn why embracing curiosity allows you to safely outgrow a path that no longer fits?

Discover how major life shifts often begin with a quiet breaking point, and learn why embracing curiosity allows you to safely outgrow a path that no longer fits.

What will I learn about: Learn to recognize when you are bending yourself to match a demanding workplace, and understand the vital difference between merely fitting in and genuinely being well?

Learn to recognize when you are bending yourself to match a demanding workplace, and understand the vital difference between merely fitting in and genuinely being well.

What will I learn about: the Silicon Valley mantra of 'ask forgiveness, not permission,' which prioritizes rapid momentum and action over the careful observation valued in traditional industries?

Understand the Silicon Valley mantra of 'ask forgiveness, not permission,' which prioritizes rapid momentum and action over the careful observation valued in traditional industries.

What will I learn about: Explore the realities of navigating a male-dominated, youth-obsessed startup culture where informality acts as a badge and traditional professionalism doesn't always translate?

Explore the realities of navigating a male-dominated, youth-obsessed startup culture where informality acts as a badge and traditional professionalism doesn't always translate.

What will I learn about: how to handle the fear of failure during a career pivot, and discover why staying authentic is far more empowering than shrinking to blend into an unfamiliar environment?

Find out how to handle the fear of failure during a career pivot, and discover why staying authentic is far more empowering than shrinking to blend into an unfamiliar environment.

Uncanny Valley

A Memoir

Anna Wiener

★ 3.9 / 5(53 ratings)

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Categories:

Biography & Memoir

If You're Curious About These Questions...

You should listen to this audiobook

💡Have you ever wondered what truly happens behind the closed doors of billion-dollar startups when the glossy marketing and buzzwords are stripped away?
💡Did you know that the Silicon Valley 'gold rush' might be hiding a darker reality of surveillance, toxic masculinity, and inflated egos?
💡Are you curious about why even the most successful startup employees are beginning to question if they've traded their personal values for a seat at the big tech table?

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Key Takeaways from Uncanny Valley

✓Discover how major life shifts often begin with a quiet breaking point, and learn why embracing curiosity allows you to safely outgrow a path that no longer fits.
✓Learn to recognize when you are bending yourself to match a demanding workplace, and understand the vital difference between merely fitting in and genuinely being well.
✓Understand the Silicon Valley mantra of 'ask forgiveness, not permission,' which prioritizes rapid momentum and action over the careful observation valued in traditional industries.
✓Explore the realities of navigating a male-dominated, youth-obsessed startup culture where informality acts as a badge and traditional professionalism doesn't always translate.
✓Find out how to handle the fear of failure during a career pivot, and discover why staying authentic is far more empowering than shrinking to blend into an unfamiliar environment.

Learning Tools

Reinforce what you learned from Uncanny Valley

Mind Map

Uncanny Valley

The Lure of Tech+

Absurdity of Start-up Culture+

Ethical Blind Spots+

Disillusionment & Exit+

Quiz — Test Your Understanding

Question 1 of 8

Why did Anna and her peers find the New York publishing industry an untenable career path after the 2008 recession?

A. The industry was rapidly being replaced by digital media and ebooks.
B. It required a financial safety net and treated entry-level workers as highly expendable.
C. The major publishing houses were moving their headquarters to Silicon Valley.
D. It demanded advanced technical skills that humanities majors lacked.

Question 2 of 8

What realization caused Anna to become disillusioned with the New York publishing start-up she initially joined?

A. The founders viewed the app as a 'lifestyle service' for people who wanted to signal they were readers, rather than for actual book lovers.
B. The company ran out of its three-million-dollar venture capital funding within the first few months.
C. She was asked to perform illegal data scraping on major online bookstores to build their catalog.
D. The founders expected her to code the app's backend despite her lack of technical background.

Question 3 of 8

What did Anna learn about the purpose of the intense, bizarre questioning during Silicon Valley job interviews?

A. They are designed to rigorously test a candidate's mathematical and analytical problem-solving skills.
B. They are meant to identify candidates who will blindly follow authority without questioning the CEO.
C. They are intended to determine if a candidate fits into the company culture and possesses a 'hustling' determination.
D. They are a legal requirement mandated by venture capitalists to ensure high-quality, unbiased hires.

Question 4 of 8

How did the engineers at Anna's mobile analytics start-up handle user privacy?

A. They strictly adhered to government regulations following the Edward Snowden leaks.
B. They encrypted all personal data to protect users from government surveillance.
C. They used a tool called 'God Mode' to view private data, which some used for tracking people or insider trading.
D. They outsourced data management to third-party security firms to avoid legal liability.

Question 5 of 8

In Silicon Valley, how were nontechnical employees typically viewed compared to software engineers?

A. They were highly respected for bringing emotional intelligence and empathy to the workplace.
B. They were seen as essential visionaries who guided the ethical direction of the companies.
C. They were resented by coders for bringing bureaucracy and diluting the workplace culture.
D. They were paid significantly more because of the scarcity of humanities majors in the tech industry.

Question 6 of 8

What was the actual result of the 'flat hierarchy' and 'name-your-own-salary' policies at the open-source software start-up Anna joined?

A. It created a utopian, completely egalitarian workplace where everyone had an equal voice.
B. It magnified inequality by giving tacit power to the young, white, male developers closest to the CEO.
C. It led to the company going bankrupt because employees demanded unsustainable salaries.
D. It empowered female developers to take on leadership roles and close the gender pay gap.

Question 7 of 8

How did the tech industry attempt to 'solve' the San Francisco housing crisis, according to Anna's observations?

A. By heavily lobbying the local government to build affordable public housing.
B. By relocating their headquarters to cheaper cities in the Midwest.
C. By expensively reinventing communal living spaces for profit, ignoring the structural problems that caused evictions.
D. By providing all entry-level employees with company-owned apartments to reduce market demand.

Question 8 of 8

How did Anna ultimately view the $200,000 she made from her stock options when she left the tech industry?

A. As a well-deserved reward for her technical contributions to the platform's codebase.
B. As a 'conflict diamond' that was valuable but came at an unforgivable human cost.
C. As seed money to start her own ethical data-analytics company.
D. As an insignificant amount compared to what the male developers received.

Uncanny Valley — Full Chapter Overview

1Recommendation
2Anna chased her dream career in New York publishing, but after the 2008 recession, it started to feel like a dead end.
3Anna joined the publishing start-up for its seemingly meaningful mission, but she quickly began noticing cracks in the facade there.
4Tech promised a lucrative, impactful future, yet when Anna reached San Francisco, she felt alienated and completely out of place.
5In her new role, Anna eagerly embraced the company culture and felt useful for the first time in her career.
6Despite her surge of enthusiasm at work, Anna’s new life sometimes felt isolating.
7Once she began forming real friendships, the glossy veneer of Anna’s job started to wear off.
8The hacker spirit at another start-up felt energizing at first, but sexism and alienation still haunted Anna.
9Anna realized she would need to compromise herself to build a successful career in Silicon Valley.
10Anna’s breaking point came when she saw the tech community couldn’t recognize, much less solve, real-world problems.
11Once she could distinguish her own values from those of the tech industry, Anna finally found meaning in her work again.

Uncanny Valley Summary & Overview

At the peak of the tech boom, Anna Wiener left a dismal professional life in New York for the modern Californian gold rush in Silicon Valley. Looking for money, stability, and social affirmation, she found an industry running on inflated valuations, gargantuan egos, toxic masculinity, and a whole lot of jargon. In Uncanny Valley (2020), you’ll follow her journey through three start-up jobs toward a more realistic valuation of herself.

Who Should Listen to Uncanny Valley?

Anyone terrified by big tech’s takeover of our lives
Those disappointed by the inaction following Snowden's revelations
Start-up employees wondering if they've made the right career choice

About the Author: Anna Wiener

Anna Wiener is a contributing writer for the New Yorker, reporting on Silicon Valley, start-up culture, and technology. She has also contributed to the Atlantic, Harper’s Magazine, the New Republic, and New York. This is her first book.

Uncanny Valley

If You're Curious About These Questions...

Listen to Uncanny Valley — Free Audiobook

Key Takeaways from Uncanny Valley

Learning Tools

Mind Map

Quiz — Test Your Understanding

Uncanny Valley — Full Chapter Overview

Uncanny Valley Summary & Overview

Who Should Listen to Uncanny Valley?

About the Author: Anna Wiener

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