James Dean and Justin Bieber have one thing in common - they captured the imagination of young people in their generations by tapping into identity crisis. While identity crisis itself is not new, the nature of identity and its expression is changing. The need for studying identity has never been as critical as it is now, as alignment to this multi-faceted identity is guiding decisions today. We see this through how they talk about brands, how they align with causes and which videos go viral. However, studying identity presents its own set of challenges. In this paper, we discuss these challenges and the Selfie project as one of the solutions.