We investigated how teachers' narratives about their histories as learners provided insight into how they enacted rough drafting and revising -- a form of ambitious mathematics instruction. We interviewed 32 teachers in the U.S.A who reported using rough drafting and revising in their mathematics teaching. Teachers spoke about positive, negative, and oscillating mathematics learning histories. When describing their teaching, they seemed to shift towards creating learning experiences that aligned with their past positive histories or shift away from creating learning experiences that aligned with their past negative histories. Variations in enactments of rough drafting and revising appeared to be explained in part by teachers' histories as learners.