This cross-comparative study examines the personal transitions of the leadership from academies in England with the leadership of independent and charter schools in the United States. Findings from this qualitative study revealed the many similarities in how principals from both the U.S. and England processed personal transitions and how those experiences influenced their leadership within the context of a new school environment or structure. To be effective leaders, principals had to address their personal transitions and establish a new identity in an unfamiliar environment and culture acknowledging the transition process as a time of "betwixt and between."