In an era of fast-track communication technology, the mindset that corresponds to the “I”- the iGeneration - encourages individualization and self-centeredness on one hand, while increasing online connection across the board on the other, enabled through digital gear and social media. Steve Jobs, Apple’s CEO, has accurately captured the psychology of today’s generation with products such as iPhones and iPods, which saturate the world market. However, people’s need for self-expression and communication also fuels a darker side - narcissism - with instant gratification and rewards, granting center stage to venues such as Facebook, YouTube and blogging at the crossroads of global culture. Where do these rampant opposite trends - egocentrism and interconnectedness - lead us towards and what does it all mean in terms of spiritual development?