An in-depth exploration of how identity is being constructed in the digital age. Drawing from the science of longevity, mental health and wellness, and social psychological literature, the author embarks on an analysis of all the ways in which technologies such as social media are pulling users away from their true selves. Confronting radicalization and extremism in digital spaces, the pre-internet age of the 1990s is explored, with the emergence of the Jerry Springer Show as the reigning king of talk serving as a harbinger for more audacious and extremist content to explode online. Disorder as identity, fame seeking and indoctrination within the manosphere all serve as significant risks to developing youth. How to navigate information overload and anchor oneself in healthier notions of self are explored. An invitation to radically reconsider one’s relationship to the self, which necessitates rethinking one’s relationship to technology.