Educational design is an area of growing significance in tertiary education. However, the career pathway to educational design is varied. Because few specific qualifications are available, educational designers (EDs) tend to take up their roles with little experience or in-depth knowledge. The purpose of this study is to investigate one new ED's development from new-to-role to experienced practitioner, in order to identify what new EDs might expect as they develop. In the early stages of her role Nicky Meuleman, ED at the Open Polytechnic of New Zealand, captured significant encounters and recorded ongoing reflection. This paper summarises and discusses the key themes from those reflections, providing insight into one ED's journey from beginner to proficient practitioner.