The paper introduces the theoretical and methodological framework behind the design of a digital internship programme (Tirocinio-on) and the related tools based on the constructs of self-directed guidance, digital work-integrated learning and career management skills. The programme involved a total of n = 289 students of the Master’s Degree Courses in the Education Area at the University of Florence, during the academic years 20-21 and 21-22 for a total of five editions. Specifically, the contribution will present the results of the computer-assisted qualitative content analysis of the final reflections provided by the PDP - Personal Development Plan prepared by n = 181 students. For the purposes of the analysis, conducted with the Atlas.ti software, the PDPs were aggregated into two primary documents groups according to the variable “current work experience”. The aim was to investigate how much this variable affects the construction of the students’ personal, formative and professional development plan.