Learning and teaching in law often oscillates between the substance of the law and the relevant techniques or skills required of lawyers in practice. The two are not mutually exclusive – for example, when drafting a contract, you need to have an understanding about the substance of contract law as well as the writing skills to draft the provisions in a particular way. But when learning and teaching law, striking an appropriate balance between substance and technique involves broader questions about the purpose of legal education. The Philip C. Jessup International Law Moot Court Competition (“Jessup”) is a unique course that necessitates students to excel in both substance and technique. At its core, Jessup requires a group of students to build a deep understanding of the relevant substantive areas of law, and present clear and logical arguments to panels of judges, legal practitioners, and academics that are often experts in those areas of law. As such, it requires students to finesse their legal research, writing, teamwork, problem solving, and oral advocacy skills. As an early career academic whose research and teaching is in public international law, I have been involved in coaching my institution’s Jessup team in the last two annual competitions. This has been to mixed results. The first year our team did well in the oral rounds and received a best memorial prize, however, the following year we placed last in the oral rounds and claimed no prizes. As I have learned through my involvement in the last two competitions, Jessup can be demanding and at times disappointing, but also hugely rewarding for both the students and the educators involved. In this editorial I intend to offer some reflections on the challenges of Jessup from the perspective of a novice coach.