Drawing from research in the learning sciences, this article argues that educators, like Jesus, should use stories as we mentor students to move beyond passive reception of information and truly apply their learning to novel situations. Thus, students can go beyond “hearing” to “bearing fruit.” This storytelling approach to mentorship strikes at the common query of students, “When will we ever need to know this?” Part of the disconnect sometimes experienced by students is that the moment of learning often looks very different than the moment when their learning needs to be deployed. In the Gospel of Luke, Jesus acknowledges this disconnect by making the distinction between “hearing the word” and the later “bearing of fruit with patience” and does so by employing a parable, a concrete story of a sower, seeds, and soils. Although stories may appear to conceal truths when compared to straightforward statements, research in the learning sciences suggests that learning from stories is better for producing understanding that could be applied to future situations. Why are stories so effective? To achieve transferable learning, students need to engage in productive struggle to make connections. Stories engaged Jesus’s disciples in struggling with what parables meant because the truths did not lie at the surface. Instead, parables required disciples to actively make connections. Jesus, instead of removing their struggles, supported their struggle to make it more productive. Research has shown that the understanding that results from productive struggle is profound, useful, and transferable. As academic mentors, we should emulate Jesus to engage our students in making productive connections by integrating storytelling into our pedagogical practice.