Recent trends in developmental psychology and developmental systems theory have opened child career development learning (CCDL) to new perspectives. This study adopts a Systems of Influences perspective with the aim of highlighting the development of systems of influences characterising students attending an Italian primary and middle school. Two levels of analysis emerged, addressing (1) the ability to identify influences and (2) the self and social awareness characterising the personal systems of influences developed by participants. This study underscores the relevance of a diachronic and systemic perspective in understanding age-specific systems of influences and their meaning for CCDL and related educational actions. It also provides insights into the meaning of the current complex challenges associated with the COVID-19 pandemic.