“Philosophy is never done nowhere. If it is not the work of a particular someone at a particular time and in a particular place, then it is not at all,” writes Ronald Bruzina in his 2004 study of Eugene Fink and Edmund Husserl’s philosophical collaboration in Freiburg during the late 1920s and 1930s. Another contributor to these years of philosophical pursuit in Freiburg was the young Czech philosopher Jan Patočka—a thinker who would become known in continental Europe for his own contributions to phenomenology but remains best remembered by historians for his late life contributions to Czechoslovakia’s Charter 77 dissident movement. This paper explores Patočka’s early orientation in philosophy, drawing upon his personal writings and letters to show how his impression of Freiburg as a philosophical idyll in which real spiritual work could be pursued shaped his own understanding of philosophical production. This paper questions what it meant for Patočka to do philosophy both in and away from Freiburg, as the harsh realities of the Second World War and early years of Communism would eventually shake Patočka’s belief in the possibility of pursuing philosophical work away from the concerns of his present. Such insights, it will be argued, can help better situate our understanding of Patočka’s early thought and apparent quiescence during the early years of Stalinism, while also illuminating the philosophical questions that seemingly led to his eventual dissident turn.