This article examines the employment trajectories of 50 young job seekers to gain insight into the critical factors that influence a young person's journey toward sustainable employment. Drawing on the employability and youth unemployment literatures, the analysis revealed that lower levels of education, limited access to transport and housing, multiple non-vocational barriers, and disengagement from job search, were typical characteristics of young people who experienced long periods of unemployment. The findings provide support for future employability research to consider factors outside the control of the young person when predicting the sustainable employment. Considerations for vocational and career counselors are discussed.