Research in academic development more often articulates stories of success than of failure in our practice. Using a self-study methodology involving written reflections and analysis of recorded conversations, this article explores how two mid-career developers define and learn from feelings of failure in the context of group facilitation. Through reflection and discussion as critical friends, we identified a series of tensions that shape our work and our identities as developers. How we reflect upon and navigate through these potentially uncomfortable places has implications for how we reframe our feelings of failure and evolve our practice.