Uncanny Valley: A Memoir

Wiener surveys the landscape of San Francisco in finer detail, from her point of view as a new resident. Historically a haven for misfits and rebels, the city is, at the moment of her arrival, “struggling to absorb an influx of aspiring alphas” (48-49). These young, wealthy members of the tech industry elite clash with the nostalgic counterculture and show little sympathy for the homeless or artists and activists reliant on rent control. This conflict reflects Wiener’s inner tension as a previously broke participant in the culture industry, now allied with the “young and moneyed futurists” (48) changing the city’s economy and identity. The large and visible population of homeless people unsettles her, particularly as it exists in such proximity to incredible affluence and performative optimism.

Wiener moves into a rent-controlled apartment in the Castro with two roommates who also work in tech. Alongside these more experienced, older residents, Wiener feels childish but attempts to fit in. Her female roommate, a product manager at Facebook, throws a birthday party at their apartment, whose guests, Wiener realizes, comprise the “nascent neomillionaire class.” She overhears two men discussing buying homes in Oakland, saying, “[Y]ou don’t buy to live there” (54), in a moment that betrays the industry’s general ethos of entitlement and detached opportunism. As she settles into a routine, Wiener reluctantly begins using a ride-sharing app for her evening commute, showing that despite her ideological qualms, she is beginning to yield to the individualistic convenience characteristic of the industry lifestyle.

Wiener’s onboarding process at the mobile analytics startup continues through a series of lunch dates with her coworkers. A lunch date with the company’s CTO is surprisingly warm and enjoyable; Wiener indulges her habit of imaginative character-building for the founders and C-suite executives that she gets to know, fondly describing details of the CTO’s dress and disposition, reading a depth and ethics into his personality from afar. They joke about a hypothetical app for literary types that could pair cocktail recommendations with users’ favorite books; less than a week later, the CTO informs Wiener he has built it. The anecdote serves as another example of the surreal nature of Silicon Valley, in which idle imaginings can very quickly become real.

Wiener attends her company’s monthly salon for tech workers curious about big data, expecting a glamorous networking event. She finds the crowd homogenous—mostly young men in branded hoodies—and the event straightforward, focused on technology and business, devoid of glamour. The main event, a discussion between two venture capitalists, is “like watching two ATMs in conversation” (61). Her team retires to a bar as she and her coworkers jockey for the CEO’s attention and praise. Stepping away to go to the bathroom, she notices two coiffed women in line who remind her of “the woman [she] had wanted, but failed, to become back in publishing: self-possessed, socially graceful, manicured” (62). The anecdote emphasizes Wiener’s development, her changing ideals and social life. As she returns to her coworkers, she notes that they are all dressed like her, in company t-shirts, “like campers on a field trip” (62)—a group in which she has begun to find her place.

The startup holds its weekly all-hands meeting on Tuesdays, during which Wiener and her fellow employees get an exciting view of the company’s progress and financial successes. Though the company is doing exceptionally well, the CEO refuses to let employees become complacent, speaking in military terms as if the business is at war. Wiener describes the CEO’s favorite phrase, “Down for the Cause,” a shorthand for deep investment in the company’s mission. Wiener develops an easy camaraderie with the other employees, as their work becomes increasingly a part of their individual identities. Wiener begins wearing flannel, like her colleagues, and listening to electronic dance music as they do, which gives her a rush and boosts her confidence: “Was this what it felt like to hurtle through the world in a state of pure confidence […]—was this what it was like to be a man?” (66).

Wiener describes various daily and weekly tasks at her job, as she provides support to employees at other businesses, mostly men, who struggle with her company’s product. While she takes pride in her work, she also describes the experience of having to “take responsibility for [the men’s] errors” (68), in a conflicted, gendered dynamic that requires her to carefully navigate the sense of entitlement common to men in her field. After a few months, she receives a $10,000 raise because the company wants to “keep her”: a bit of praise both admiring and condescending. Despite the slight friction of these microaggressions, Wiener remains excited about her work.

Following the raise, Wiener leaves the rent-controlled apartment behind and moves to the Haight. Her new studio brings with it an increased sense of independence and autonomy. As soon as she moves in, she notices homeless people and other nomadic folks who loiter, fight, and sleep on the street outside her window, people whom she describes as clinging to a “revisionist nostalgia” and a mythologized San Franciscan identity that “may never have existed” (74). She explores the city extensively by foot and by bike, eavesdropping on strangers’ conversations and watching their performative exercise routines. Everywhere, she observes a constant, often absurd clash between nostalgia and futurism. She reluctantly seeks companionship via a dating app but quickly deletes her profile.

A friend from high school arranges for Wiener to meet an engineer he knows in the city whose demeanor and dress embodies many of Silicon Valley’s aesthetics and priorities. Wiener realizes she doesn’t “fit in to the engineer’s meticulously curated life” (78), but the date nevertheless eases her loneliness slightly. The chapter closes on an anecdote of a “girl date” arranged by the CEO between Wiener and the CEO’s girlfriend, both of whom expressed a desire to make new friends. They meet for a drink; the CEO’s presence is felt even with him absent, and the interaction is pleasant, but hollow. Wiener closes on an elegant anecdotal description of herself and the CEO’s girlfriend simultaneously refusing a second glass of wine, an ironically mutual acknowledgment of their lack of connection.