This CASDA EdCast features Dr. Piccirillo in dialogue with special guests Amy Hawrylchak, Principal at Tech Valley High School and Shelette Pleat Principal for CTE at Capital Region BOCES on the topic of boundary crossing in leadership spaces. This concept allows leaders to move beyond their comfort zone, crossing boundaries into unknown and potentially unsettling space in order to grow personally and professionally. They discuss the benefits of taking these risks in order to better engage in educational equity work, and build more authentic, substantive relationships with both students and colleagues. Their honest exchanges model boundary crossing in practice and should encourage all leaders to move beyond the familiar and towards meaningful growth.