Bill Freund, the late social historian and leading analyst of African history, passed away in 2020 soon after finishing his autobiography. Often described as the academy’s ‘outsider insider’, he was an eminent South African historian who published prodigiously in the areas of labour, capital and economic history. What influenced this American-educated academic to become such an astute and trusted observer of the political economy in Africa? In this deeply introspective autobiography, we follow Bill’s intellectual journey from a modest Jewish home in Chicago in the 1950s – where new vistas were opened up through voracious reading, inspiring teachers and intellectual engagement – to the Universities of Chicago, Yale, Ahmadu Bello, Dar es Salaam and Harvard, and finally to a permanent teaching position at the University of KwaZulu-Natal in Durban, South Africa in 1985. Freund begins with his family’s fascinating history in Habsburg Austria, describes émigré life in the USA, and provides astute reflections on his teaching experiences. Peppered in between the commentaries on academic life are stories of his travels, poems he wrote for loved ones, and endearing anecdotes of friendships that shaped his life. Freund offers rich insights into the world of Africanists and their scholarship on different continents, as well as thoughtful and balanced observations on late- and post-apartheid South Africa. His autobiography reveals the intellectual man and the world that shaped him – and which he in turn influenced through a deep commitment to rigorous scholarship. It includes a select bibliography of his many publications as well as a foreword by Robert Morrell on the making of this book.