Career guidance claims a lineage to "modernity", where individuals carve dignified lives for themselves, irrespective of social origin. Here, "social justice" has particular connotations, relating to the meritocratic redistribution of resources in ways that reward ability and effort. This article explores alternative conceptions of social justice, taking seriously the fundamental insight that if individuals make history, they do so in circumstances not of their own making. Drawing on recent theories of social justice, an effort is made to "trouble" mainstream notions of career guidance, and to imagine how it can be of the greatest benefit to the least advantaged.