Opportunity Costs

Part of the uncanniness of Uncanny Valley, Anna Wiener’s memoir of her time at a series of tech startups, is its familiarity. As a vivisection of tech’s bleak buoyancy, the internet’s death grip on our lives, and the hideous, misplaced confidence of the people who design and run these systems, it’s essential reading. But the book is also about the idea of work: the weight of it; its ideals, temptations, and contradictions; the seduction of a paycheck and a promotion; the dynamic of a team; the struggle to understand what makes something a job or a career or a calling, and where the lines are between those things. More than the timely (and entertaining) expose of a sick industry, it’s the broader job stuff that sent me reeling.

Wiener starts out as a low-level employee in publishing, a field rich in cultural capital but lacking things like decent pay and a shot at upward mobility. When she takes a job at an e-book startup, it seems like a savvy pivot, one that doesn’t force her to compromise her interests or her talent. But after her assigned duties and personal motivation both prove too ambiguous to be sustainable in that context, it doesn’t take much urging for her to turn away from publishing entirely and parlay her new tech-adjacent experience into a job working in customer support at an analytics startup in Silicon Valley. Though she wasn’t exactly successful at her first startup job, she was seduced by her brief encounter with the tech sector’s “optimism and sense of possibility”—its innate belief that it makes sense to be excited about the