Although there is a common result in recent research and practice that digital skills are important for every educated citizen, little is known of how these skills are evolving over a long period of time. Our study looks into the development and use of digital skills in former middle school students who had an individual access to the laptops a decade ago and are now entering the workforce. Using a qualitative approach, we look at results from an earlier study on one-to-one laptop use in middle school students, as well as results from follow-up interviews with three students from that cohort. More specifically, we present narrative stories offering a rich description of the personal experience of digital skill acquisition through information and communication technology (ICT)-assisted learning and the sustainability of these skills later in adulthood. Our findings indicate three specific types of digital skills, namely, technological resourcefulness, digital self-efficacy or empowerment, and open-mindedness toward technology, that emerge as key elements of the participants' perception of postsecondary academic and eventual further career success. The results of this study can be used to better understand how ICT skills are acquired and how they evolve over time in young people who grew up (or are growing up) in a digital world and how this process can be enhanced by educational institutions and workplaces.