Undisciplined Design (UD) is an emerging approach suited for experiment-driven innovation and creative processes, allowing fluid disciplinary engagement in engineering design. However, its openness and adaptability also introduce challenges, particularly when integration, evaluation, and risk mitigation mechanisms are absent. This paper examines the Google Glass project through the lens of boundary objects, identifying two key dangers in UD: overconfidence in technological inevitability and unintended consequences. The analysis highlights the need for structured checkpoints to manage epistemic uncertainty while preserving UD’s exploratory potential. To address these challenges, we propose incorporating participatory design methods to facilitate cross-disciplinary negotiation and present a decision-making checklist to guide UD projects in product design and innovation.