This paper discusses a portion of the findings of a mixed-methods study that examined the career patterns of senior educational administrators in public school divisions in Manitoba, Canada. Data based on the career paths of senior administrators from both a survey and interviews of senior administrators were analyzed and compared along three variables: (a) position; (b) context; and (c) sex. This paper reports the findings of one aspect of the study that asked senior administrators to provide advice to aspirants interested in becoming senior administrators. Findings suggest that in Manitoba context, sex, and position interact to create differences in career experiences. Overall, senior administrators enjoy their work, but encourage aspirants to seriously consider the personal and professional responsibilities and ramifications of moving in to a position of such public and political responsibility. (Contains 1 table and 2 footnotes.)