Informed by Constructive Developmental Theory and the Threshold Concepts Framework, we interviewed retired academic developers from four continents and asked them to describe their processes of learning from perceived failures and how they see the role of academic developers in supporting academics through failures. Findings regarding participants' definitions of failure, ways of making sense of and learning from failure, and recommendations for supporting academic colleagues' learning from failure are shared through tables, quotations, and poetry. Findings show that 'wise academic development' embraces curiosity about failure, integrates the (sometimes) transformative nature of failure, shares the load of sense-making, and cultivates connectedness.