Stories that were written by my grandfather at the turn of the 20th century spiraled into my daily life as a nurse-teacher at the turn of the 21st century. In this paper, I explore a common plotline of my Afi (Islandic for grandfather) and me as pioneers by linking his life stories to the tensions I experience in my contemporary professional worklife. Our narratives intersect, crossing generations with stories that illuminate for me ways to understand these tensions as a faculty member and curriculum-maker. [Article written in collaboration with J. W. D. Bjarnason.]