This article describes the landscape of teaching assistantships (TAships) in the Mathematics Department of a large, public, research institution. First, we present visualized data describing the terrain for all mathematics graduate students. Second, we focus on three specific journeys in that terrain. We employ an autoethnographical research methodology to analyze the pedagogical paths of three recent graduates through written reflection. We highlight some surprising themes that emerge, identify key moments in each reflection, and make three proposals, applicable in broader contexts, to capture and confer their benefits.