Thomas Aquinas and William Langland inherited the dynamic metaphor of journeying as a fundamental concept of the Christian life and harnessed it to animate their magisterial texts: the Summa Theologiae and Piers Plowman. Christians' journey back to God consists in the way of charity, yet it is far from straightforward or sequential. Rather, it is impinged upon by epistemic ambiguity, our willful continued habits of resistance, and inherent limitations on our perfection. In sum, the virtues are divine gifts humanly received, treasure in earthen vessels. Together these authors show the complexity we ourselves will find along this life's journey, enable our understanding to appreciate that complexity, and in limited ways cultivate in us the virtues they describe.