The present study examined career pursuit pathways in 100 Israeli emerging adults (54 men) who were followed from age 22 to 29. Employing a semi-structured interview at the age of 29, participants were asked about current work and educational status, work and educational goals and status changes in recent years, and to reflect on the meaning of the processes they followed. Analyses of interviews yielded four distinctive career pursuit pathways that were associated with different levels of concurrent well-being: Consistent Pursuit, Adapted Pursuit, Survivors, and Confused/Vague. Self-criticism, efficacy, and level of motivation measured seven years earlier predicted pathway affiliation at 29. In addition, paternal support was found to serve as a protective factor associated with adaptive career pursuit. Gender differences were found, with women more likely to be affiliated with the less adapted pathways. In addition, paternal and maternal support were differently associated with career pathways. By employing this mixed-method approach, the findings demonstrate the diversity, and gender-related nature, of career pursuit and development pathways during emerging adulthood, and indicate the importance of personality and both paternal and maternal support in the process of career development.