The 2023 Foundation Year Network conference focused on an important theme: failures, mistakes, missteps and meanders in the foundation year context. It provided an important impetus for reflection: after all, the relative institutional ‘success’ of a programme of study will often be judged on a mixture of quantitative and qualitative data collected from, or about, students studying on the programme, for example, attainment, progression, and satisfaction. It is, therefore, too easy to overlook how the teaching staff view the processes, iterations, and risks taken in designing, teaching, assessing and iteratively improving programmes of study which are deemed successful within product-oriented metrics, achieved only through reflection on the intervening failures, mistakes, missteps and meanders by the ‘insiders’. Herein, we detail a case study on a core component of our foundation year programme, the ‘Conference Project’, and provide a narrative on how it has iteratively developed, why specific decisions were taken, and the next iteration currently in development. The challenges of operational restraints and the triad of tensions between the expectations of teachers, students, and the academy will likely resonate with our colleagues’ experiences, or, at the very least, highlight some pitfalls to be avoided.