57 pages 1-hour read

Uncanny Valley: A Memoir

Nonfiction | Autobiography / Memoir | Adult | Published in 2020

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Key Figures

Anna Wiener

Uncanny Valley tells a broad story of Silicon Valley’s tech industry and the generation of millennial innovators, employees, and consumers that drove its growth. Wiener appears doubly as the book’s naïve protagonist—a participant in that industry—and its knowing narrator, speaking with the benefit of hindsight. Her narration deemphasizes her personal story as she foregrounds anecdotes of others—CEOs, founders, developers. Wiener’s emotional journey progresses subtly from optimistic aspiration through a loyal immersion and then remorseful entanglement with tech’s all-encompassing lifestyle. She displays a keen sociological awareness, situating herself socially and economically with explicit disclosures of salary offers, increases, benefits, and equity. Ironically, she does not disclose the actual names of the many large, recognizable companies that shape the world through which she moves—an allusion to her status as a former employee who may have been made to sign a nondisclosure agreement. These disclosures and wry nondisclosures encourage trust as she names her privilege and the limitations of her perspective.


Wiener paints herself initially as an accessible “everyman,” with a vague desire for stability and a longing for “momentum.” She enters Silicon Valley not as a technically literate insider, but an average individual with unusual access to tech’s inner workings. Her dual status as both insider and outsider invites the reader’s identification with her journey. In the book’s second half, she matures emotionally through a process of quiet realization but struggles to authentically exercise her agency. This struggle manifests feebly, with a quiet sense of tragedy, in a last-minute effort at political action before the 2016 election. In the Epilogue, when she makes an exhausted but decisive exit from the industry, she achieves a partial reclamation of autonomy and integrity. 

The CEO of the Mobile Analytics Company

The CEO of the mobile analytics company is Wiener’s first employer in Silicon Valley. Many of his employees strive to gain his admiration and praise; early in her time in the company, Wiener finds herself longing for his approval. As the company grows, his leadership style grows increasingly harsh and vindictive, as he prefers to “rule by fear.” While Wiener indulges a habit of projecting rich, complex motivations into his calculating actions, his manipulative tactics drive Wiener to leave the company. Still, she struggles to let go of a need for the CEO’s approval. He symbolizes Silicon Valley’s unapologetic and obsessive relationship to power and achievement, which Wiener simultaneously admires and fears. At the end of the book, she finally rejects this dynamic, though her rejection is of no consequence to the CEO.

Ian

Ian, a robotics engineer at Google, meets Wiener at a party and the two quickly begin dating. To Wiener’s frustration, he does not disclose much about his company’s confidential projects. Wiener envies the embodied quality of Ian’s work making and manipulating hardware; her own work, by contrast, sometimes causes her to forget her body entirely. He provides a grounded, anchoring presence in Wiener’s life, balancing her tendency to become overly immersed in her work. He expresses healthy skepticism about tech’s various flights of fancy. When Wiener compares herself unfavorably to tech moguls and CEOs, Ian reminds her of the facets of her own personality that are unique and valuable apart from what is valued and monetized within the industry. 

Patrick

Patrick is the CEO of a popular startup, whom Wiener unexpectedly befriends through social media. Wiener disputes many of his viewpoints but leaves conversations feeling inspired, rather than downtrodden or hopeless. She experiences a tension between his private self and public persona. In their meetups he is warm, thoughtful, and flexible in conversation, but online he projects entitlement and overconfidence. In the book, Patrick acts as a foil to Wiener’s skepticism, aware of Silicon Valley’s pitfalls but unapologetic about his goals and his investment in success. While Wiener struggles to be more decisive, Patrick advances his career with few misgivings or hesitations. 

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