This paper will explore the autobiographical writings of the modern Chan master Laiguo Miaoshu 來果妙樹 (1881~1953). Beginning with the premise that autobiographical accounts, especially in Buddhist contexts, have a didactic function, I propose to read the records of Laiguo’s early years as a young monk not (or not only) as an account of actual events, but as a carefully considered illustration of an exemplary life of practice. The autobiographical accounts relayed in the lectures (kaishi) Laiguo delivered during an extended meditation retreat at Gaomin Monastery in 1942 and the autobiography he completed in 1949 both detail his time as a monk in training, his awakening at Jinshan, and his years spent in solitary retreat before assuming the abbacy of Gaomin. This paper will look closely at those accounts in an effort to understand Laiguo’s state of mind when he was an older master engaged in training a new generation of monks.