Despite chairing the University of Cambridge philosophy department for eight years, Ludwig Wittgenstein was described by his biographer as a “reluctant professor.” He did not believe that philosophy should be approached like a job, and he often attempted to dissuade his students from pursuing academic careers. Indeed, Wittgenstein changed direction in his professional life numerous times. For a while, he lived in a wooden hut that he had built next to a Norwegian fjord; he later contemplated farm work in the Soviet Union. Deriving from a 1948 journal entry that Wittgenstein wrote at age 59, this bit of advice reminds us that the celebrated author was, unfailingly, young at heart. Wittgenstein was wary of anyone who tried to elevate themselves above others by sounding smart. Instead, he preferred the authenticity of those willing to laugh at themselves.