From a life course perspective, this article examines how an intergenerational sample of 20 African-American women in Chicago describe and make meaning out of their struggles and advancements to make inroads into the principalship. Being born on opposite sides of the Civil Rights Movement distinguishes markedly how these women perceive their experiences and share their stories about their journey to become principals. In the face of woefully restricted professional opportunities, African-American women born prior to the Civil Rights Movement portray their journey as a progression from conceding "deferred dreams" to fulfilling their "callings." In contrast, African-American women born after the Civil Rights Movement view their journey as one availing them to new horizons of professional opportunity. Their divergent reflections on the salience of race and gender in the professional realm sheds light on the scholarly contention that the tradition of activist-leadership in African-American education has waned in the 21st century.