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The rarely discussed Middle English poem “Alas, quid eligam ignoro” might be read as an estates satire, but it takes the form of a complaint. Two young men (a clerk and a layman) describe their seeming paralysis in the face of an impossible choice. In contrast to the usual strategy of estates satire, the poem does not view the moral failures of the professions from some kind of objective distance but from the bottom-up perspective of two individuals who see choice as a kind of foreclosure or hopeless compromise. The crisis of “Alas, quid eligam ignoro” resembles similar crises faced by Will in William Langland’s Piers Plowman and by the speaker of a fragmentary poem known as “Why I Can’t Be a Nun.” In contrast to prevailing views of professional identity as a natural, inescapable destiny, these texts suggest that finding a profession might involve anxious introspection and that this search might be obstructed at every turn.