The purposes of this study are to (1) examine the factorial validity of Schein’s career anchors orientation inventory (COI), comparing the original eight-factor model with an alternative nine-factor model, (2) examine the cross-cultural invariance of the COI and its factor structure across two countries, (3) investigate whether core self-evaluations (CSE) is associated with career anchors, and (4) determine whether the relationship between CSE and career anchors varies by country. Survey data were collected from 469 participants (230 from the United States and 239 from Turkey). Based on multigroup confirmatory factor analysis, the results indicated that the alternative nine-factor career anchor model of the COI has better factorial validity and configural invariance than Schein’s eight-factor model. The findings showed support for the association between CSE and the pure challenge anchor and a moderating effect of culture on the relationship between CSE and two other anchors.