Advancing technology changes skill demands: for human expertise to remain valuable in the labor market, skill supply must adjust. The authors study how new digital technology reshapes skill acquisition, and the resulting impacts on workers’ careers. They construct a novel database of legally binding training curricula and updates therein spanning the near universe of vocational training in Germany over five decades, and link curriculum updates to breakthrough technologies using Natural Language Processing techniques. Their findings reveal that training adapts to technological advance by incorporating digital and social skills while reducing routine-intensive task content, mostly through new skill emergence. Using administrative employer-employee data, the authors show that curriculum updates help workers adapt to new skill demands, and earn higher wages compared to workers with outdated skills. By contrast, older occupational incumbents face declining wages, consistent with skill obsolescence. Firms respond by increasing capital investments when exposed to workers with updated skills. These findings highlight the role of within-occupation skill adjustments in meeting evolving labor market demands for non-college educated workers.