The transition from school to work is very smooth for some youth and less smooth for others. Many factors influence the transition such as the level of education, the quality of schooling, intelligence, opportunities, and family background. This paper addresses several measurement issues related to the assessment of the school-to-work transition. To illustrate these issues, several existing findings from the National Longitudinal Survey of Youth 1979 (NLSY79) are discussed. Each finding relates to alternative measures or methods employed to assess the school-to-work transition.