A push towards digitalization and a solid inflow of foreign investments has provided a basis to create new jobs and facilitate a smoother transition of youth into the Serbian labor market. Although still inordinately high when compared to its EU counterparts, the unemployment rate youth has decreased over the last decade following improved macroeconomic trends. Further positive outcomes necessitate targeted, labor market policies focused on strengthening employability - of interest to research are changes in the external environment (particularly Industry 4.0 requirements) and deficiencies caused by rigidity in formal education. Taking into consideration youth career aspirations and capacities, a Principal Component Factor Analysis was applied to data collected from the survey of youth (18-29 years old, n=125). The results help provide conclusions on youth attitudes related to learning preferences, additional skills required and the self-estimation of their digital-skill capacities. The analysis extracts five factors relevant for developing effective active labor market measures.