Context: Women face many challenges in their lives, including harassment, lack of acceptance, and excessive workloads. These challenges affect their daily experiences and influence major life decisions, such as pursuing a career in IT. These issues further diminish the already low participation of women in the industry, making the field less appealing to potential newcomers. The challenges often begin before women even enroll in bachelor’s programs, setting a difficult path for those aspiring to enter the software development industry. Goal: To investigate challenges women face in IT at different stages of their lives—specifically, during their last year of high school, while they are at University pursuing their bachelor’s degree, and as practitioners. Furthermore, we aim to explore solutions to address these identified challenges. Research Method: To achieve this goal, we conducted a literature review using the snowballing technique to identify challenges and solutions already reported in the literature. The literature review results were used as input for workshops, in which we sought to understand the perspectives of high school women, undergraduates, and practitioners regarding the same set of challenges and solutions identified in the literature. Results: Our studies revealed that, regardless of the life stage, women feel discouraged in a toxic environment often characterized by a lack of inclusion, harassment, and the exhausting need to prove themselves. We also discovered that some challenges are specific to certain life stages; for example, issues related to maternity were mentioned only by practitioners. Conclusions: Women encounter gender-related challenges even before deciding to enter the software development field when the proportion of men and women is still similar. While issues such as feeling the need to prove themselves are mentioned at all three stages, high school women’s challenges are more often directed toward convincing their parents that they are mature enough to handle their own responsibilities. As women move to the other stages, the challenge shifts to proving their competence in managing responsibilities for which they have received training. Increasing the inclusion of women in the field should, therefore, start earlier, and profound societal changes may be necessary to boost women’s participation in the field.