This chapter explores the ways that digital messaging and the latest innovations, like Glass, disconnect us from the world in significant ways. One of the most significant ways is how it confuses the non-instrumental virtue of authenticity: it confuses “saying what we mean and meaning what we say” with transparency. The simple equation of transparency with authenticity creates a nation of Glassholes. The notion that informational transparency is the necessary and sufficient grounds for an authentic life is both inaccurate and ethically fraught. Political officials and activist groups both embraced body-camera technology on the premise that it would increase transparency and accountability. In both commercial and political contexts, the transparency movement is typically spearheaded by highly skilled engineers and activists. Despite public rhetoric espousing the benefits of transparency, the implicit lesson of these organizations is that people with better computer skills are somehow more entitled to live an authentic life.