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This paper analyzes a novel data source on career paths for a large fraction of the US-based technical (IT) workforce and provides evidence that the rapid expansion and contraction in demand for technical skills that occurred during the dot-com boom and bust created a divergence in labor outcomes between a) older and younger technical workers and b) male and female technical workers. Preliminary analysis suggests that the unemployment durations of women in the IT workforce grew relative to those of men during the boom, whereas older IT workers faced higher displacement rates and longer unemployment durations than younger IT workers after the bust. Further evidence suggests that the mechanism for both of these differences was related to skill acquisition. Both women and older workers were less likely to transition into firms that were investing in new information technologies during the boom, and faced falling demand for their technical skills after the bust. After the bust, women were more likely to change occupation, and older workers were more likely to change industry. Our findings suggest that rapid fluctuations in demand for skills associated with IT innovation cycles, along with the idiosyncratic nature of skill acquisition costs borne by technical workers, can partially explain differences in labor market outcomes by gender and age in the IT labor force. Implications for IT labor supply and for policy makers are discussed.