This paper examines whether students are entering the generative AI era with sufficiently strong educational foundations, focusing on the relationship between learning environments and changes in ICT related career aspirations across countries. The analysis uses country-level data from PISA 2018 and 2022, combining indicators of student autonomy, digital skills and teacher support. A mixed-method approach is applied, including descriptive statistics, regression analysis, clustering, latent representation learning (using Variational Autoencoder-VAE), discriminant analysis and probabilistic modeling to capture both observable and latent dimensions of educational readiness. Unlike prior research that treats learning loss, digital skills and career expectations separately, our analysis integrates them within a comparative longitudinal framework. It shifts the focus from short-term post-pandemic effects to the structural capacity of education systems to prepare students for digital and AI-driven labor markets. Results show a global but uneven increase in ICT career aspirations. Digital skills emerge as the strongest and most consistent predictor, while teacher support plays a complementary role. Autonomy shows weaker, context-dependent effects. Educational readiness is multidimensional, and ICT aspirations evolve relatively independently from other career domains.