Among many Human endeavors, the spiritual one is very personal. Each of us has been deeply moved several times in our lives experiencing profoundly. But in today’s digitally connected world, the spiritual experiences are not only rare but we forget its existence as we are more hooked to digital entertainment or work. This book explores the challenges and answers in our spiritual growth in terms of psychological, social, and scientific point of view in contemporary terms. The fruit of spirituality is enlightenment. This book attempts to explore the challenges of prince Siddhartha in becoming a Buddha by retelling his adventures in a novel way to portray his psychology and growth. And how he was influenced to make spirituality not only personal but available for everybody. This book also attempts to compare his spiritual growth process with the Tibetan Buddhist Prayer’s flag, which can also be considered as the map of enlightenment.