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Because the role of the principal has changed dramatically, preparation programs have adapted to better prepare these leaders. This qualitative study examines one program using surveys and interviews of completers. Results found that new leaders found themselves in an uncomfortable but necessary space, what we deem the “in-between.” Using the theoretical framework of the third space, this qualitative study found three areas defining this space: sense of self, transition of thinking, and complexity of the third space. We argue that incorporating room for the third space into principal preparation programs and utilizing these spaces for self-reflection and critical dialogue should be an aim of principal preparation programs. Purposeful, careful development of such spaces can lead to stronger schools and communities.