1 John 2:16 reminds us, “For all that is in the world, the lust of the flesh and the lust of the eyes and the boastful pride of life, is not from the Father, but is from the world. (1 John 2:16, NASB). This is an important part of discipleship, but what hermeneutic do we use to communicate this in a 21st century context. This paper will link the words of 1 John 2:16 with three other biblical narratives; the Fall of humanity (Genesis 3:1-7), the conflict between Mary and Martha (Luke 10:38-42), and Simon the magician (Acts 8:9-24). Through biblical exegesis and modern understandings of pridefulness, the objective is to provide for the 21st century church a biblical definition of “pride as sinfulness.” These three scriptures will be contrasted with examples of pride and being “proud” in a righteous sense as described within the Bible. What does sinful pride look like? How is righteous pride applied within a local church context? The goal of the paper is to add to the body of knowledge and interpretation of these four specific passages of scripture (including 1 John 2:16) while also providing a new way of defining and understanding the historical sin of pride, of which the New Testament warns the church. Of special importance will be looking at this issue with the backdrop of 21st century culture and what that means for a new generation of Christians who work, learn, and lead in a culture that celebrates pride as a virtue.