At a young age Smedes considered himself a reprobate, someone born destined for damnation. This is based on the Calvinist belief that every person has a destiny predetermined from birth. Smedes enrolled in Moody Bible Institute in an attempt to reconcile this frustration and suffering with his God, but this failed until he happened about a theology text in a used bookstore that transformed his understanding of his faith, pushing him to focus less on questions of his own worth.

While the question of free will and determinism are considered in much of philosophy, in Christian theology they often take on a specific meaning: the question of whether one's position as saved or damned is effected by human choice, or is strictly predetermined. We see the effect of both of these positions on Smedes sense of unworthiness. He considers himself predestined for hell, and seemed wracked by a sense of hopelessness due to predetermination. Later, however, he becomes a proponent of infant baptism, and of viewing infants as saved once they are baptized rather than expecting them to have a turning point in their life where they accept their faith and are "born again."

Smedes and his wife had a child that died within a few hours of being born, and he struggles with how to reconcile that tragedy with the Calvinistic doctrine that all things happen as God has planned. Later in life, he sinks into a deep depression and spends two weeks in a cabin hearing the voices of all those close to him promising to desert him. Ultimately, the book gives little in the way of a coherent or logical answer, but rather shows Smedes doubling down on his faith and pursuing an ever-closer reliance on his God, beginning to conceptualize this as a friendship late in his life.