Using self-determination and schema therapy theories, we examine the cognitive-motivational processes underlying the regulation of career decisions and the experience of well/ill-being during the key school-to-work transition among Portuguese high school students. We obtained two pathways of transition: A "Bright" pathway, where need satisfaction associates with positive and flexible schematic processing to predict autonomous regulation of career decisions and experienced well-being, and a "Dark" pathway, where need frustration relates to schematic processing of social information to predict unique variance on controlled career decisions, low well-being and ill-being. Schematic processing of social information explained unique variance in ill-being over and above need satisfaction and need frustration. Overall, the findings support the cognitive-motivational determination of career decision making.