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Design culture is increasingly present within organizations, especially with the rise of UX as a profession. Yet there are often disconnects between the development of a design philosophy and its translation in practice. Students preparing for UX careers are positioned in a liminal space between their educational experience and future practice, and are actively working to build a bridge between their developing philosophy of design and the translation of that philosophy when faced with the complexity of design practice. In this study, we interviewed ten students and practitioners educated within design-oriented HCI programs, focusing on their design philosophy and evaluating how their philosophical beliefs were shaped in practice. Building on prior work on flows of competence, we thematically analyzed these interviews, identifying the philosophical beliefs of these designers and their trajectories of development, adoption, or suppression in industry. We identify opportunities for enhancements to UX educational practices and future research on design complexity in industry contexts.