Recent changes in labor market and working conditions have rendered youth’s education-to-work transitions and career prospects more uncertain. This study investigated how youth, while still in education or training, deal with perceived growing occupational uncertainties in terms of goal engagement (i.e., investing active effort in goal pursuit; surmounting obstacles) and goal disengagement (i.e., distancing from unattainable goals; protecting the self against failure experiences). Analyses with two closely matched samples of youth aged 16–25 years from Germany (N = 529) and Poland (N = 530) revealed high levels of goal engagement and a clear preference of engagement over disengagement. Whereas levels of engagement were comparable across countries, disengagement was considerably higher in Polish youth. Regarding the sources of individual differences in engagement and disengagement, sociodemographic factors had very limited effects in both countries. Compared to sociodemographic factors, the level of perceived growing occupational uncertainties, and especially youth’s primary and secondary appraisals thereof, were more strongly and consistently associated with engagement and disengagement, especially in Germany, pointing to the prominence of perceptions and appraisals in shaping youth’s responses to growing occupational uncertainties. We offer cultural and economic explanations for these findings and discuss implications for interventions aimed at fostering youth’s engagement in preparing for their future careers under today’s uncertain conditions.