The extent to which college student-athletes are prepared to enter the workforce upon graduation is an important concern to universities, the National Collegiate Athletic Association, and to many college student-athletes themselves. In this interview study of 18 college student-athletes from 12 sports at a Division I university, the features and extent of career readiness are identified as well as the personal qualities associated with career readiness. Given the criterion established for identifying levels of career readiness, seven participants were classified as career ready, three were semi-career ready, and eight were minimally or not career ready. Further, four personal qualities distinguished athletes who are career ready from those who are not. Those qualities were optimism, resilience, adaptivity, and their recognition of crossover skills, that is, skills, knowledge, and personal strengths required for both sports and work domains. Implications for training student-athletes in positive personal qualities and recognizing crossover skills are discussed.