Does educational content respond to technological advances, enabling workers to acquire new expertise? We study how digital technology transforms skill acquisition and impacts workers' careers. We construct a novel database of legally binding vocational training curricula in Germany over 5 decades, and link curriculum updates to breakthrough technologies using Natural Language Processing. Technological change spurs curriculum updates, shifting training content toward digital and social skills while reducing routine-intensive task content, predominantly through new skill emergence. Curriculum updates account for two-thirds of deroutinization in vocational skill supply over this period. Using administrative employer-employee data and a stacked DiD design, we show curriculum updates help workers adapt: new-skilled workers earn higher wages, with increases up to 5.5\% for technology-exposed occupations. In contrast, older incumbents experience wage declines, indicating skill obsolescence. Firms increase capital investments when exposed to workers with updated skills, consistent with capital-skill complementarity. These findings highlight within-occupation skill supply adjustments' central role in meeting evolving labor market demands.