Novice tutors often conceptualize learning how to tutor as a kind of metaphorical journey, one with a compelling, but not fully recognized, destination. Cognitively speaking, they are learning how to tutor while at the same time learning what the activity of tutoring means. This paper seeks to position tutor education within the conceptually rich field of teacher education, especially as it is informed by insights from sociocultural theory (SCT). Using tutors’ reflective narratives, the author illuminates how orientation to task, a fundamental concept in SCT, changes over time through frequent and intensive reflective writing, when carried out in combination with practical tutoring activities. Specifically, the data suggests that proleptic engagement (identifying elements of the future expert self in ongoing novice activity) and affective engagement are important signals of development. The journey is particularly challenging because – to interrogate the metaphor – the novice is trying to build the track while riding the train to the terminus.