This study analyzes the increasing presence and capabilities of wearable computing devices in the cornucopia of personalized digital data. We argue that the institutional data practices typical of Google Glass will pose policy challenges and herald yet another dramatic shift to personalized data marketing. We also highlight the characteristics of Google's existing synergetic data practices that will shape the development of not only Google Glass, but also all subsequent wearable mobile devices in light of 360-degree data collection. The key organizing concept of our study is the disjuncture between (1) institutional and (2) policy forces in harnessing dual market mechanism, which frames how the new communication industry operates in the marketplace of ubiquitous personal advertising. We conclude by summarizing the three key areas of political-policy concern (privacy; anti-trust; and user competence) and suggest future solutions, with the discussion on the future of wearable computing practices related to the freedom of the human body.