This paper aims to identify critical constraints as perceived by U.S. and California women superintendents and to determine how these women overcame them. The Survey of Influences on Female Superintendents' Careers (SIFSC) was used in two studies to collect quantitative and qualitative data on women superintendents in the United States and in California. This paper discusses data from three parts of the SIFSC survey: (1) demographics of both groups; (2) mean scores of four constraints deemed most critical by respondents; and (3) respondents' written strategies for overcoming these constraints. Descriptive statistics were used to analyze demographic and evaluative responses. The means of the three most critical constraints from each group were further analyzed for significant differences. Written statements were qualitatively analyzed by looking for themes across data. The superintendents in both studies agreed on three critical career constraints: difficulties in breaking into existing organizational networks, the belief that women cannot handle the superintendency's political aspects; and lack of organizational encouragement to apply for administrative positions. Solutions ranged from seeking mentoring opportunities to becoming involved with different publics, being well-prepared, taking risks, and accomplishing difficult tasks. An appendix of career constraints is included. (Contains 31 references.) (MLH/Author)