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ISTE and CSTA have achieved consensus in the field about the core skills and dispositions that constitute computational thinking. Yet the assessment of computational thinking continues to remain illusive. The skills themselves often overlap, and include not only observable actions within a problem-solving model but also dispositions or attitudes that support those actions. Moreover, it is not yet clear how computational thinking impacts long-term choices, for example for postsecondary education or a career. This paper examines several aspects of this problem. First, it details the development of an observational tool, the Student Exploratory Computational Thinking Observation Scale (SECTOS), that allows for assessment of students when they are engaged in authentic activities that provide them with arenas for choice. Based on an earlier tool for measuring “21st Century skills”, the tool focuses on the problem-solving process, including the ability to analyze data, transfer the problem-solving process to new domains, and think in terms of broader systems. Secondly, the paper analyzes changes in computational thinking among disenfranchised youth ages 18-25 who are engaged in an online Alternate Reality Game (ARG) structured to create a learning environment that enhances digital literacy and workforce readiness for careers in Information Technology. Players make choices of in-game and out-of-game activities that score points within the game, leading to in-game and real world prizes. Early game activity choices include hands-on learning activities including video game development, film production, and social media, then focus on increasing knowledge of IT careers as players move up game levels. As players create their game world through their choices, they “level up” the six levels of the game, moving into postsecondary formal and informal learning environments. Data includes persistence in the game, number and types of activities completed, length of time needed to level up, as well as demographic information about the players. This data is analyzed with SECTOS data to determine the impact of game choices on the development of computational thinking. Finally, the relationship of computational thinking to the development of possible selves indicative of the evolution of IT workforce readiness sheds light upon the degree to which changes in computational thinking as developed in an ARG environment impacts education and career trajectories.