The convergence of the two waves of “digitization” and “aging” is a distinctive feature of contemporary society, and the updating of technological products has caused older employees to face the digital divide, which affects their workplace environments, psychological states, and work behaviors. Based on resource preservation theory and stress cognitive evaluation theory, this study examines the influence mechanism of technology shock awareness on older employees’ job reinvention in the digital age. Through stratified regression and Bootstrap analysis of 303 questionnaires, it was found that technology shock awareness significantly positively affected job reinvention of older employees, including convergent job reinvention and defensive job reinvention, with job insecurity mediating. In addition, perceptions of organizational support positively moderated the positive effect of job insecurity on convergent job reinvention while weakening the impact on defensive job reinvention. This study enriches the research on technology shock awareness and job reinvention for employee management and corporate practices in the digital age.