Digital literacy is becoming a standard requirement for many other occupations, and its importance is likely to grow due to rapid advancement in technologies. However, young women do not consider IT as a choice for further education or employment. Therefore, only 15 % study IT and 10 % work in IT-related fields. This paper deals with the professional transit of this underprivileged group into the IT field (a typically male field). The results are interpreted on the basis of a two-year program of the Digital Academy from Czechitas focusing on retraining 300 women (mainly women on and after maternity leave and fresh university graduates) for technical positions in 2017 and 2018 in the Czech Republic. Czechitas is young Czech organisation which help women, girls, children but also parents and teachers to explore the world of information technologies through workshops and long-term courses on different levels of expertise, focused on particular knowledge or technology. Czechitas are focusing on new approaches to helping people identify and develop skills that are relevant for high-demand jobs. Through their existence they have realized that for the successful career transit into computing fields there is a need to empower and equip women with a complex system of hands-on technical workshops and also well designed concept of soft skills trainings.