This paper examines the development of "vocational habitus" as five apprentices in the carpentry trade move from high school to an apprenticeship training centre and then into the workplace. After a year, three students were continuing with the apprenticeship while the other two were not. This paper explores how individual and structural factors came together to produce these outcomes through an analysis of data from interviews with the students, their parents, and trainers. Analysis of the data suggests that signs along the way foreshadow outcomes--for example, students' prior experiences in school and part-time work, expectations regarding training and work in the trades, family support, social capital, and locations within the field. Findings suggest that more support could be provided for young people who are likely to experience difficulty with transitions, and more explicit attention could be given to helping students recognize tensions between fields while developing a "feel for the game". (Contains 5 notes.)