In this article, the author describes her personal journey at Cuyahoga Community College (Tri-C). Early in her career, the author often focused on the immediate projects and priorities that she was asked to lead. The author gave much less thought to what the next leadership opportunity might be. While experts may advise against this lack of intentionality, the journey was built on a strong work ethic, the accomplishments of her teams, her professional reputation both inside and outside of the college, and the personal connections the author made over several decades in higher education. She believes that experience is critical for any emerging leader, but having a collaborative style, possessing a steady temperament, and having the political savvy to negotiate in tough times goes a long way toward being an effective leader. Herein, she describes her leadership position as the dean of student affairs and also the vice president of enrollment management and student affairs. In doing so, she emphasizes the importance and benefits of true shared dialogue, decision making, and a culture of mentorship between leaders.