Forty-seven percent of higher education chief academic officers have been in their positions for three years or less, but there has been no systematic review and exploration into why this level of turnover has occurred. The purpose of this qualitative research study was to gather data from a select group of chief academic officers to more fully understand the reasons why these senior administrative leaders choose to leave or stay in their positions. Overall findings from semi-structured interviews with 13 Chief Academic Officers (CAOs) indicated that they perceive their job to be the toughest on campus, with significant challenges related to their duties and responsibilities including a large number of direct reports, frequent difficult decisions, grueling meeting schedules, no time for planning, and people management challenges. Participants also identified challenges with work relationships and described how they spent much of their time walking the tightrope between the president and faculty, and with individuals or campus group members who created challenging circumstances for the CAO. In contrast, participants also shared that the most energizing and fulfilling elements of their roles included leading and contributing to the success of the institution and students, developing strategy, building and supporting people, and having positive relationships with the president, vice presidents, and the CAO office staff. The majority of these CAOs also shared that they were already seeking, or will be seeking, a presidency in the next few years.