This paper presents the early-stage user workshop findings and subsequent design of a game-based learning approach to entrepreneurship. The specific context is to address the dual-career training needs of athletes, as part of a large-scale European online course (MOOC). An interactive card-based activity was used within a small scale focus group, with the purpose of enabling dialogue between end-users (n = 11), as to elicit their experiences of using games for understanding athletes’ dual career training needs. Initial findings from this exercise was a suggestion that quantifiable performance indicators (scores, points, achievements) could be preferable to less quantifiable measures (e.g. narrative progression, or multiple scenario outcomes). Establishing meaning, sense-of-purpose, and identity within the game were also highlighted as desirable features by the focus group, when compared to other options as detailed in this paper. The subsequent prototype of the game is presented, with reference to these findings.