The value of visual analogies in problem solving has been extensively researched, with most of the work focusing on their benefits. This study explores the much less investigated research question of how visual analogies as cues for insight problem solving are generated using freehand sketching. More specifically, we focused on the creative process of the first author who is a professional artist, for generating two sets of visual analogies to support solving a classic insight problem of 8-coin. First set of sketches was generated for analogies capturing the problem insights through static images, while the second set capturing the problem insights through a dynamic, time-based media format. We employed an experiential research method consisting of artist’s reflections on his freehand sketching practice in his creative process. Inaccuracy of freehand sketches presents opportunities to generate new concepts of analogy. This study contributes to a deeper understanding of how visual cues can be generated, and what principles, tools, in particularly, through freehand sketching, and what methods of practices can be used in research.