Meaning of "Step By Step" by Jesse Winchester

"Step By Step" delves into the concept of the afterlife and the idea of judgment in Christianity. The repeated lines regarding starting over if a Saint steps out of line suggest the importance of staying true to one's beliefs and living a righteous life to enter Heaven. The Devil's smile could symbolise temptation or the presence of evil even in the divine realm. The mention of innocent children playing around the throne highlights the purity and lack of sin in Heaven, contrasting with the troubles of the mortal world. The singer's desire to understand the Devil's smile before entering also reflects a curiosity about the complexities of good and evil and the nature of the afterlife.