The U.S. may be experiencing a shortage of qualified applicants for the superintendency. Highly qualified candidates often do not want the job. Underrepresentation of women in the superintendency confounds the problem. This study was conducted to determine the most commonly exercised path to the superintendency in the Northwest. Career trajectories were compared between male and female superintendents, and certificate holders who are not superintendents. Commonalities were sought between the routes chosen by current male and female superintendents. Career choices of potential superintendency applicants were examined to determine whether they were gaining requisite types of administrative experience. Results show that aspects of the job, such as stress, politics, and low pay differential, influence many candidates away from applying. Women commonly see themselves in support roles and positions lower than the superintendency, which strongly correlates with a lack of career advancement. The model path to the superintendency from a high school principalship is followed more by men than by women. The pool of candidates for the superintendency may decrease over the next 10 years as more people decide against applying for a highly stressful position. The shortage of applicants would be exacerbated if female administrators are stopped by an administrative ceiling to their career ladder. (Contains 35 references and 4 tables.) (RT)