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This paper uses data from career histories of technical contractors to explore how they experience, interpret, and allocate their time and whether they take advantage of the temporal flexibility purportedly offered by contract work in the market. Technical contractors offer a unique opportunity for examining assumptions about organizations, work, and time because they are itinerant professionals who operate outside any single organizational context. We find that contractors do perceive themselves to have flexibility and that a few achieve a kind of flexibility unattained by most permanent employees doing similar work, but rather than take advantage of what they call “beach time” and “downtime,” the majority work long hours and rarely schedule their time flexibly. The contractors' use of time is constrained by the cyclic structure of employment, the centrality of reputation in markets for skill, the practice of billing by the hour …