When Lambert Strether exhorts John “Little” Bilham to “live!” (154) in Henry James’ The Ambassadors (1903), we trust that we know what he means. What, after all, could be more self-evident than the idea that life should be experienced as fully and enjoyably as possible, and that it is a mistake not to do so? Going against the grain of critical consensus, in this essay I argue that Strether’s injunction becomes ringed with uncertainty the moment that it is subjected to analytic scrutiny. This uncertainty does not generate scepticism about the possibility of leading a life, but is rather an invitation to pose questions about the everyday language we employ to describe, evaluate, and make sense of the activity of ‘living.’ I claim that James uses the breakdown of Strether’s speech to draw attention to the fact that much of this language is wedded to a hyperbolic picture of agency that is either rigidly voluntaristic or deterministic. I show how James’ representation of Strether’s consciousness of himself as an agent puts pressure on this picture by making it difficult to determine whether he is acting or being acted upon.