Studies on Tao Yuanming have often focused on his personality, reclusive life, and pastoral poetry. However, Tao’s extant oeuvre includes a large number of poems on history. This article aims to complement current scholarship by exploring his viewpoints on life through a close reading of his poems on history. His poems on history are a key to Tao’s perspectives with regard to the factors that decide a successful political career, the best way to cope with difficulties and frustrations, and the situations in which literati should withdraw from public life. Examining his positions reveals the connections between these different aspects. These poems express Tao’s perspectives on life, as informed by his historical predecessors and philosophical beliefs, and as developed through his own life experience and efforts at poetic composition.