Technological growth affects the way we live, communicate, and work. Over the coming decades, up to 60% of existing jobs might be lost to automation. This creates pressure on the job market, demanding more tech professionals, while creating job insecurity for positions that might be automated. Although tech and computing is an appealing career choice with high salary, job security, working flexibility, space for creativity and career growth, vast majority of women are dropping their interest in tech during adolescence, with very limited recovery in later years, when preventable reasons are stopping them from reconsidering their decision and joining tech. In this paper, we share our experience with a project assisting women in their 20s and 30s in changing career towards tech. The project has been implemented within our education non-profit organization, called Czechitas, which is recognized as the leading platform for addressing gender diversity in tech and software engineering in the Czech Republic.