ANTHONY SANFILIPPO has been learning, researching, practicing and teaching medicine over the past five decades. He has held key roles at various levels of medical and educational leadership and, for the past 16 years, directed one of the oldest and most venerable medical schools in Canada as it adapted to dramatically expanding medical knowledge, societal needs, student expectations, financial constraints, and one rather disruptive pandemic. He has published numerous scientific articles, provided hundreds of invited presentations and received recognitions for teaching, leadership and service. More recently, he has taken up writing as a means of exploring opportunities to better align medical education with the needs of contemporary society.