Anticipated retirements and relatively short tenure in office create a shortage of community college presidents in the United States. To fill the unprecedented number of vacancies requires a cadre of candidates well prepared for the demands of the position. Using Satir's change model as a theoretical framework, this year-long reflective study examined eight first-time community college presidents in California. Satir's model describes six stages of change; this article focuses on the third stage, one of chaos, or disequilibrium. Participants identified key professional experiences, the role of mentors, professional development activities, and doctoral studies as important strategies for navigating this professional disequilibrium and pursuing their career aspirations.