Design theory and practice are increasingly prevalent in legal and justice systems, at times reframing the relationship between the law and the world it seeks to make just. This article presents my professional experiences introducing design theory, methods, and mindsets into legal and government contexts, highlighting challenges and tensions across various legal design projects. Challenges include the justice sector's struggles dealing with complexity, the unfamiliar logics of design and abductive reasoning, and the legacy of positivist and instrumentalist philosophies. As a response, I propose a legal design that incorporates phronesis and re-orients around anticipation, rather than prediction.