The article explains the career path of vocational teachers. Vocational teachers, with few exceptions, have a background related to a different economic sector. The decision to become a teacher is challenging as it involves adapting to new behaviours, culture and regulations. Within the transformation process, an individual can cross the border from his/her initial occupational field to the vocational school. As a vocational teacher, the individual has to adapt several structural changes, pedagogical demands and trend in a vocational field. Drawing on the analysis of narrative interviews with 21 Estonian vocational teachers, the article highlights the factors and motives for becoming a vocational teacher and analyses the transition processes and perspectives of the vocational teachers’ career. The individuals’ career path has been analysed using the concept of boundary crossing. As the narrated career paths represents the individual’s own view of career related factors, the career is considered a subjective career.