The experiences and perspectives of four women who have exited urban s
chool district superintendencies are examined in this article. Sources
of disenchantment with the political aspects of the role are discusse
d. Structural and sociocultural frameworks are used to interpret findi
ngs about women's continuing ''outsider'' status in educational leader
ship. The authors conclude by advocating increased attention to both t
he recruitment and retention of women and members of other underrepres
ented groups in the superintendency.