The digitalization of work is a top priority among employers, education providers and policy makers, as it presents a great opportunity for the development of regions, improving competitiveness and creating new demands and opportunities for job creation. However, it creates new demands for technological literacy and for the qualification of the young professionals. The sustainability of the promised digitally enabled development depends of the ability to create opportunities to integrate people, leverage their talent, careers, and work life contexts. For education institutions, the concerns about addressing the need for new related with the digitalization is driving the debate for changes in the models for qualification. In such settings, information technology (IT) professionals rank as one of the fastest-growing professions. However, many regions face challenges to qualify and retain enough IT talent, notably in medium-density urban areas, where small and medium-sized companies dominate the business landscape. It is therefore important to understand what affects the attractiveness of IT studies and professions, notably when choosing a direction for their higher education studies. This paper presents and discusses the results from an exploratory study addressing the perceptions of families and young students about the characteristics of IT professions. The study sets up to investigate how the influence of family members and close relatives, the experience of the youngsters, the breadth of the job market and the area of knowledge underpin the motivations and the decision-making process of young students when they assess and define their choices for their future. The study resorted to a questionnaire and offers information about the attitudes towards IT careers, and brings forward key insights for debating what might affect the attractiveness of qualification in IT. The identification of these factors may inform the decision makers about the development of education opportunities to meet the demand of skilled professionals that digitalization requires.