One of the most popular stories found in the Upaniṣads centers around a debate between the ritualist and philosopher, Yājñvalkya, and a series of interlocutors about the nature of sacrifice, the self, and the cosmos. This story, from a textual—historical perspective, is unique in that the last interlocutor, Śākalya, is said to die by having his head shatter because he is unable to answer a question about the fundamental nature of immortality. In this paper, I analyze the interrelationship of these two main characters and argue that this relationship is one key to not only understanding the portrayal of these characters, but also the larger import of this debate about immortality. I provide an intratextual rationale for the head-shattering conclusion and discuss how character and doctrine are fundamentally intertwined in this text.