Since 2012, the Deans' Roundtable Conference has provided independent school student life professionals with the opportunity to Connect, Learn, and Share. As educators, our jobs are all-encompassing; requiring us to oversee the day-to-day running of faculty, students, and school life. We are also tasked with building a cohesive learning environment that is both challenging and fun. The conference creates a forum in the summer and times throughout the year where student life professionals can connect to reflect, share best practices, collaborate, and laugh. Participants also gain an expanded professional network, actionable ideas, a greater understanding of how other schools operate, and an online forum for continued insights.