Gaining autonomy is a key aspect of growing up and cognitive control development across childhood. However, little is known about how children engage cognitive control in an autonomous (or self-directed) fashion. Here, we propose that in order to successfully engage self-directed control, children identify, and achieve goals by tracking contextual information and using this information to select relevant tasks. To disentangle the respective contributions of these processes, we manipulated the difficulty of context-tracking via altering the presence or absence of contextual support (Study 1) and the difficulty of task selection by varying task difficulty (a)symmetry (Study 2) in 5-6 and 9-10-year-olds, and adults. Results suggested that, although both processes contribute to successful self-directed engagement of cognitive control, age-related progress mostly relates to context-tracking.