Despite a lifetime of leadership experience, Carter-Tod still struggles with what she calls “the challenge of becoming.” As a woman of color and a first-generation college student, her sense of her personal and professional identities do not always or easily align. In this reflective chapter, she revisits several leadership moments in her life to uncover—and reclaim—the practices of situational, agency-based leadership. She also underscores the importance of feeling a sense of belonging even in places that require significant change.