Objectives: Game development students have a daunting career ahead of them, complicated by competitive industry hiring, the passion behind digital media and entertainment work, and inequitable work cultures. By understanding the work-life experiences of graduated game development students in digital media careers, higher education curriculum can be designed to model ill-structured problems and engage students in practicing how to balance work and life while developing relevant skills. Participants: Eleven participants who graduated from one game development program at Purdue University span a diverse range of ethnicities, gender identities, and disciplines in digital media, including art, production, animation, and design; no programmers were available in opportunistic sampling. Study Method: Semi-structured interviews were conducted with each participant to explore their preconceptions of the digital media industry in education, current experiences in their work and workplaces, and preferences for the future of the industry. Through lenses of critical pedagogy, signature pedagogy, and hidden curriculum, interview data were analyzed using thematic analysis through a constant comparative method. Findings: Themes related to shared and contradicting experiences were reported. Most participants had heard horror stories about working in the digital media industry, but they did not turn away from it. Some positions follow strict pipelines, while others in the same field flexibly shift software programs and tasks throughout the day. Crunch time can be, but is not always, inevitable in the industry, depending on the workplace and circumstances. Participants divulged love-hate relationships with their career fields and their work; conditions are better than expected in some ways, and worse in others. These understandings characterize how difficult it is to form lasting curricular priorities and structures that can prepare students for the extreme variety of industrial environments they may apply to. Conclusions: The authors conclude that designing coursework toward a flexible, critical, dialogic curriculum would invite students to engage with faculty more deeply and personally in career development. Instead of repeatedly restructuring predetermined curricular paths to ever-advancing specialized industry positions, time and energy can be spent guiding students to study existing career paths and purposefully tapping into the technical knowledge and insights of faculty. When problematic elements of work culture--such as coercion to overwork--may currently be part of a hidden curriculum, we recommend that they be integrated into the formal curriculum, to be interrogated together by students and faculty alike. By continuing to network with graduated students entering the industry as novices, and keeping up with industry veterans, instructors can model existing problems for students to anticipate and respond to.