In the article, issues relating to the socio-political measures aimed at increasing flexibility in managing the relationship between the spheres of work and family on the individual level of life strategies are examined within the framework of the gender theories of organisation. The environment of management is described as a gender regime in which an organisational masculinity functions. This a priori establishes unequal conditions for the formation of women's career patterns. On the basis of a case study of the life strategies of women in managerial positions and other results drawn from research on the management environment from a gender perspective, the author identifies strategies employed towards women, who in the management environment are in the position of tokens, by the gender regime and its actors in the highest positions of the organisational hierarchy, and identifies the strategies that in connection with these conditions are created by women who desire to succeed in an environment set up in this way. The certain degree of flexibility that on the individual level can be achieved in the management environment is founded on a gender contract, which in the end continues to disadvantage women because it emerges in connection with the given structure of set rules of the environment. If flexibility is to be introduced as a non-discriminatory mechanism, organisational masculinity as such must be called into question.