The school-to-work transition (STWT) represents a pivotal challenge in individual development, necessitating a global and interdisciplinary approach to address its inherent complexity. This article examines some key characteristics of the current labour market, focusing on the Italian context, which is undergoing profound transformations that disrupt traditional production systems. In the contemporary landscape, labour market instability has become a norm rather than an exception, often resulting in unclear future prospects and leaving individuals—particularly adolescents—grappling with uncertainty and a lack of direction. For younger generations, this sustained uncertainty exacerbates the challenges of an already delicate and transformative phase of life, generating scepticism toward both present realities and future possibilities. The evolving skills required to navigate the STWT present significant challenges for educational planning, particularly within institutional, organizational, and pedagogical dimensions. Emerging technologies, such as artificial intelligence (AI), are reshaping lifestyles and work environments, further complicating the dynamics of STWT transition. It is essential to undertake comprehensive pedagogical reflection and rigorous research to critically evaluate and redefine educational strategies and policies. Such efforts are crucial for equipping adolescents with the resilience and adaptability required to navigate instability and uncertainty, fostering preparedness for an unpredictable future.