This qualitative study examined the perceived barriers to the principalship by prepared principal candidates as a means of understanding why some candidates are unsuccessful in acquiring a principalship. The use of a questionnaire, interviews, and reflection postcards served as the data collection methods concerning their lack of success in achieving a principal position. Portraitures were used to illuminate the journey of these candidates as they completed the necessary requirements, developed the skill vital to becoming a principal, and interviewed for prospective openings. The findings revealed that the barrier to the principalship for these candidates is their own lack of awareness regarding who they are and what they know as it pertains to the principalship and their lack of self reflection and self correction skills. Implications for further study include, a study of principal candidates who have acquired principalship after a significant length of time and their perceptions of what corrections they made that advanced their career; comparison study of the preparation experiences of principal candidates who were successful in getting a principalship in contrast to principal candidates who were unable to advance to the role; and a repeat of this study using male candidates.