A sceptic is one who does not know, and who holds out little hope that a satisfactory philosophical explanation to the mysteries of life and truth actually exists. Augustine had reached the stage of scepticism.

As he continued to grow in intellectual capacity, he asserted that his primary aim was the search for truth. In this search, Augustine had first joined the Manichean sect, a group that believed in many of the Christian precepts but had difficulty accepting that the divine Christ was found in the human being named Jesus; and the Scriptures did not impress him. He followed the Manichean sect for quite some time, but abandoned it when he saw its flaws.

At one point at late adolescence in Carthage, he had even studied astrology while he considered the possibility of the world being hinged upon chance. While living and teaching in Milan between the years 383 and 386, the intellectual and existential path of Augustine had three distinct phases - Manichean, sceptic and Christian. Augustine lingered for a while in skepticism. He could not immediately trust another authority because his trust had been betrayed: “While [my soul] could not be healed except by believing, it was refusing to be healed for fear of believing what is false.” Stumbling upon the books of the Academics, he easily understood their scepticism of the human capacity to know truth. Not only was Augustine's scepticism an obstacle to his entrance into the Christian tradition, but the Manichean tradition he thought he had abandoned stayed with him, blinding him to narratives he would soon encounter when relooking at Christianity.

Disillusioned in his pursuit of hedonism, paganism, Manicheanism, and even of power and ambition, it is understandable that Augustine began to entertain the notion that ultimate truth might not be able to be known or attained. He became impressed with the philosophical scepticism that had become prominent in old school of Plato, which was called the Academy. Augustine fell into "Academic Doubt," as it is still called. He fell into a profound depression and indeed despaired of ever coming to know the truth. "The Academicians kept my rudder for long in the middle of the streams, resisting all winds," he wrote. He suffered deeply from the most dreadful doubts that can attack a person who has felt the impotence of many varieties of thought in the face of spiritual problems. He felt the depressing effect of the question, Can a human being know anything at all? Can anything be proved true? With this scepticism, Augustine was at his lowest point in life.

He reached the point of fearing that truth could never be obtained. He had not accepted the Christian faith that his mother Monica had offered him as a child. The Manicheans now appeared to him to be fraudulent, simplistic, self-deceiving and intellectually bankrupt. And astrology, which suggested chance as the cause of what happened, no longer appealed to him. As a sceptic, he was seriously doubting that it was humanly possible to find Truth. He was searching for truth, but could not yet find it to his satisfaction. In his search for truth, Augustine was genuinely troubled by the arguments of the Sceptics that a person can be certain of nothing, and that careful thinking in no way provides a reliable guide to a wiser life. Here the Neo-Platonists, especially the disciples of Plotinus, came to his rescue. Turn inside, they said, from the variable senses and the ambiguities of the world, and you will discover what you cannot doubt. This was the eternal and universal Truth present to but above the human mind; it included the truth of mathematics, and the truth of beauty, good and evil.

Augustine now came to see a way out of his dilemma. In turning inward, he deduced, "I find that I am, that I know that I am, and that I delight in that being and that knowing. This knowledge I cannot doubt: for if I doubt, then I am, I know that I am, and I delight in that. At least, then, I know one truth: that I doubt, and that in doubting I am. And so knowing a truth, I cannot doubt Truth." And in the midst of this fearful spiritual isolation he was making contact with Ambrose. As this was happening within his mind, Augustine also listened to Ambrose, Bishop of Milan, who was one of the most influential personages in the whole Roman Empire at that time. The process to conversion for Augustine was about to accelerate dramatically.

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