Risk created a sense of choice, oftentimes false, that pervaded tech workers’ narratives about their careers. For people who worked in Internet start-up companies, the risks they took represented, in their own words, their hopes and dreams and “only the upside” in the words of a software engineer. But these attitudes and rhetoric about being one’s own boss and having control over one’s company did not emerge by chance or in a vacuum. The social context for this frenzy and the rush to boldly take risks occurred in the midst of major structural change from an economy in which 30 percent of the workforce was unionized to the wide acceptance of at-will employment. The attitudes toward risk that we saw during the dot-com boom happened in the context of the shift from a workplace where regular, full-time employment was the norm to a growing percentage of the American workforce in nonstandard jobs, many lacking health insurance, pensions, and training. Risk presented a choice when jobs were shifting from the security of regular employment to flexible hiring to meet demand only when times were good.