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A large body of research on the “glass ceiling” has shown that women’s career advancement is limited relative to men, but little is known about how highly-successful women break through this barrier. We hypothesize that one way women improve their chances of advancement within firms is through atypical career paths, which allow them to move from jobs with limited advancement opportunities into ones with more fecund career ladders. We do not expect men to similarly benefit from atypical career paths. We test this hypothesis using monthly observations of 53,311 exempt U.S. employees at a West Coast Fortune 500 tech company over an eight year period, from 2008 to 2015. We first demonstrate that jobs disproportionately staffed by women offer, on average, lower pay and lower advancement opportunities within the firm. We then find that erratic career mobility, defined as a sequence of atypical job moves, results in differential outcomes for women and men. Women who move erratically are more likely to be promoted than similarly erratic men. However, this also presents a risk, as women’s erratic movement results in lower performance appraisals than similarly erratic men. We call this the “dilemma of mobility.”