According to the Organization for Economic Co-operation and Development, in rapidly changing societies of the 21st century, meta-cognitive and meta-reasoning skills are becoming essential for adolescents, as well as socio-emotional skills (OECD, 2018). One of the most important meta-cognitive skills is anticipatory thinking. Anticipatory thinking can be described as the process of acknowledging and preparing for complex situations. Starting from this point, in this context, characterised by continuous changes, anticipatory thinking represents a crucial competence in the Vocational Guidance field to plan future personal and professional trajectories (Thomaes et al., 2023). In fact, by implementing anticipatory thinking, young people can construct future scenarios that are attentive to environmental and social sustainability, and translate them into present actions (Poli, 2010, 2017; Brassett & O'Reilly, 2021; Light, 2021). Thus, this study aims at examining relations between anticipatory thinking and key career-related constructs: career adaptability, future orientation, and decisiveness regarding professional future. A sample of 227 Italian adolescents (M = 17; SD = 1.09) was involved, and measures of anticipatory thinking, career adaptability, future orientation, and career decidedness were administered. The structural equation model run in M-Plus showed anticipatory thinking predicted career decisiveness, directly, and indirectly, through the mediational role of career adaptability and future orientation. Moreover, career adaptability and future orientation acted as mediators. As regards practical implication, the results carried out emphasize the importance to support anticipatory thinking in adolescence, and a specific example of career interventions to promote anticipatory thinking will be provided.