The problem with authenticity--the idea of being "true to one's self"--is that its somewhat checkered reputation garners a complete range of favorable and unfavorable reactions. In educational settings, authenticity is lauded as one of the top two traits students desire in their teachers. Yet, authenticity is criticized for its tendency towards narcissism and self-entitlement. So, is authenticity a good or a bad thing? The purpose of this article is to develop an intimate understanding of authenticity by investigating its current interpretation and criticisms, its struggle with narcissism and relation to freedom. Examining authenticity as multilayered self-exploration reveals a composite of understanding, care, and acceptance. While a side current of acceptable tension shifts our understanding of authenticity from the security of self-determination to the messy interplay involved in being "true to one's self" and being "in-the-world".