In the first of our “Winding Road to Academia” series, Professor Brian Kernighan joined us to talk about his journey from undergraduate studies at the University of Toronto and graduate work at Princeton to a career at Bell Labs, and his transition from research to undergraduate education when he returned to Princeton as a professor in the Department of Computer Science. The wide-ranging conversation included suggestions for recent graduates as they considered their career paths, reflections on what it means to create your own luck, advice on how to improve as an educator, and plenty of stories from the trenches.