The use of technology for educational purposes has become widespread with the advent of the fourth industrial revolution (Dal santo et al., 2022). Drawing from Masdonati's et al. (2022) model, the current research aims to show that the digital educational context can allow for decent education and play a tremendous role in the success of the school-to-work-transition. The study develops a model exploring how digital educational context is related to motivation to learn, proactive skill development during university studies, and career satisfaction once employed. We tested our hypotheses with a three-wave panel study composed of 297 individuals via a structural equation modeling analysis involving a sequential mediation. The results support our hypotheses and emphasize the importance of digital educational context for a better school-to-work-transition through motivation to learn and proactive skill development. The study provides practical implications which are discussed.