One key career transition during emerging adulthood is the school-to-work transition. As careers have become much more dynamic and complex, this particular has also become more challenging for young adults. In this chapter, the authors explain how the school-to-work transition has changed and how individual agency and structural factors can interact to lay an early foundation for sustainable career development. In line with this, the authors argue that career competencies and employability are crucial concepts for today’s school-to-work transition. Finally, they look forward to how future research might contribute to further understanding the contemporary school-to-work transition. In all, this chapter argues that an adaptive school-to-work transition is crucial as a building block for long-term sustainability of careers.