In this conversation, Drs. Claire Brady and José-Luis Riera reflect on what they learned from planning, leading, and participating in the recent NASPA Institute for Aspiring Vice Presidents for Student Affairs. They shared exploring the realities of the current moment in higher education, holding space to consider if this role is really for them, and examining multiple pathways for transition and success. Themes of hope and healing are paired with the challenges of higher education and this leadership role specifically.