Artificial intelligence (AI) is increasingly being viewed as a creative partner rather than as a tool. How to design such collaborations is still a subject of speculation. In this pictorial, we propose a collaborative role for AI to prompt self-reflection. We explore this through a practice-based inquiry of whether and how AI could help a designer reflect on and relate to their own work. Three designers annotate a collection of images representing their fascinations, with subjective labels, indicating different dimensions of their visual concepts. These labels are used to teach an object detection model the designers’ perspectives. Then, they used this trained model on their own design work to evaluate the AI's potential to prompt self-reflection. By describing this process of AI-training we explore how an AI can help us become aware of our own implicit perspectives.