Philosophical and Psychological Road Blocks
In his Confessions, Augustine knits together the intellectual and emotional seamlessly. Philosophy involves arguments, yes, but the true lover of wisdom will not merely contemplate, but apply the deliverances of truth to his life. Conversion for Augustine is not only an act of the intellect, but it is psychological, involving the will and emotions as well as the mind. Through him we see that the reasoning faculty can be blinded by one’s psychological state, God’s truth being darkened in proportion to one’s sin. Augustine writes that God opposes the proud and he allows this truth to be on full display as he recounts his conversion narrative.
The process of resolving one’s intellectual reservations about Christianity often involves a disentangling of legitimate conceptual difficulties with its truths from volitional resistance to its ethics. The two are tightly woven together in human nature, complex as it is. The Christian Augustine expertly utilizes Scripture, the penetrating sword that divides soul and spirit, joints and marrow in order to separate these strands. In this way, he is able to cast his glance back over his life and see his motives more clearly from within the context of biblical wisdom. “Man is a great deep, Lord,” he writes. “You number his very hairs and they are not lost in Your sight: but the hairs of his head are easier to number than his affections and the movements of his heart.” G.K. Chesterton wrote that “one may understand the cosmos, but never the ego; the self is more distant than any star.” Augustine shows us that without God’s gentle grace, no one would be saved, no one would come to God, for who can fully penetrate the mysteries of the self?
Struggles with Scripture
As an example, Augustine writes that at age nineteen he learned from reading Cicero the love of truth. From him, Augustine was inspired to move away from the pursuit of earthly pleasures and accomplishments, the prevailing cultural expectations of the day, creating in him “an incredible intensity of desire” and longing for “immortal wisdom.” “Suddenly,” he writes, “all the vanity I had hoped in I saw as worthless.” With this reorientation of his loves from self-serving pursuits to the pursuit of wisdom for the sake of itself, he was then instinctively drawn back to the Scriptures of his youth. Still, he was not ready for their simple beauty and layered complexity. He writes that in them he found “something not grasped by the proud, not revealed either to children, something utterly humble in the hearing but sublime in the doing, and shrouded deep in mystery.” He was blinded by an intellectual pride in his newfound love of wisdom, so his “conceit was repelled by their simplicity.” This kept him from being able to “penetrate into their depths.” Augustine’s heart was not yet ready to take in the riches of Scripture as he did not possess the mandatory humility for the task.
First, he must be taken to the limits of reason to see that there is an uncertainty that is both coherent and rational when it comes to knowledge of God. Much like modern materialism, the paganism of his day tended to limit the imagination to working upon what is experienced through the physical senses. Throughout his conversion, his conception of God is repeatedly challenged to deduce from what is seen to what is unseen. Like moderns, he struggled to move past the tangible realm into the intangible, from the good in this world to its Source. This struggle is made all the more difficult by the human tendency to greedily lock the gaze upon sensual pleasures of this world, making idols out of the good things that come from God rather than turning to Him to be saved.
In the opening passages, Augustine catalogs the confounding paradoxes that met him in Christianity. He was, as Chesterton would say, trying to get the heavens into his head. Augustine writes,
“What then is my God, what but the Lord God? For who is Lord but the Lord, or who is God but our God? O Thou, the greatest and the best, mightiest, almighty, most merciful and most just, utterly hidden and utterly present, most beautiful and most strong, abiding yet mysterious, suffering no change and changing all things: never new, never old, making all things new … ever in action, ever at rest, gathering all things to Thee and needing none … ever seeking though lacking nothing. Thou lovest without subjection to passion, Thou art jealous but not with fear; Thou canst know repentance but not sorrow, be angry yet unperturbed by anger. Thou canst change the works Thou hast made but Thy mind stands changeless. Thou dost find and receive back what Thou didst never lose; art never in need but dost rejoice in Thy gains, art not greedy but dost exact interest manifold.”
Once one has allowed for the utter transcendence of God, these paradoxes become a sort of light by which this world of such apparent contradictions can be understood (like free-will and God’s sovereignty, or God’s immutable yet personal nature). There is a strange certainty in paradox that Augustine comes to appreciate, “of something worth knowing,” as Chesterton called it. Augustine needed to be taken right up to these limits of his finite reason to be then able to approach God with humility.
Reconciling God’s nature
The second of Augustine’s roadblocks involved reconciling God’s nature. False expectations and an inadequate understanding of Christian teaching formed the bulk of the hindrance for him. He would eventually come to see that once again his mind was on earthly things, unable to go beyond what the eye sees to that which is invisible and eternal. “[W]hatever I tried to see as not in space,” he writes, “seemed to me to be nothing, absolutely nothing, not even a void: for if a body were taken out of its place and the place remained without any body, whether of earth or water or air or sky, it would still be an empty place, a space–occupying nothingness.”  Ironically, he would later realize that had he been able to see himself more clearly, to take true stock of his own thought processes, he would have seen that within them lay the key to understanding God’s transcendent nature.
“My mind was in search of such images as the forms my eye was accustomed to see; and I did not realize that the mental act by which I formed these images was not itself a bodily image: yet it could not have formed them unless it were something and something great … You had not as yet enlightened my darkness.”
Until such enlightening, he joined the ranks of scoffers of Christianity. “I had my back to the light and my face to the things upon which the light falls,” he writes, “so that my eyes, by which I looked upon the things in the light, were not themselves illumined.” In his book I Burned For Your Peace, Peter Kreeft offers a helpful distinction: Like modern materialists, Augustine strove for perfect knowledge of imperfect things rather than submit to imperfect knowledge of Perfection Himself. Kreeft writes,
“Augustine … says that we must choose between imperfect knowledge of perfect things and perfect knowledge of imperfect things. We can have perfect, or at least adequate, knowledge of this imperfect world, but not of the perfect God. And even Aristotle said that the least knowledge of the most perfect things is rightly prized far above the most perfect knowledge of imperfect things.” 
Augustine would later see, in the light of God’s truth, that his intellectual confusion had a volitional component. He never thought to question the erroneous teaching themselves by going to the source to discover the truth. He had “been barking all these years not against the … faith but against mere figments of carnal imaginations.”  He confesses that he “had been rash and impious in that [he] had spoken in condemnation of things which [he] should have learned more truly of by inquiry.” He writes that in his ignorance of God’s incorporeal nature, he “should have knocked at the door and proposed the question how it was to be believed, and not jeeringly opposed it as if it were believed in this or that particular way.” Thus, he gives us another example of how inextricably linked our reasoning capacity is with our will and emotions.
It was at this time that God graciously brought into his life a teacher that was educated in philosophy yet steeped in the riches of the Christian faith. From Bishop Ambrose, he “became more and more certain that all those knots of cunning and calumny, which those who deceived [him] had tangled up against the holy books, could be untangled.” Through Ambrose’s teaching, many of his difficulties with Scriptures melted away, and he obtained his first taste of Platonic philosophy and its insights into the spiritual nature of God. He writes that though he “did not yet know that [the church] was teaching the truth, but [he] had found that she did not teach the things of which I had so strongly accused her.”
Reconciling the Nature of Good and Evil
Augustine also struggles to understand evil. He asks, “Where then is evil, and what is its source, and how has it crept into the creation?” Having once accepted the immutability of God, he is confounded by the coexistence of something as mutable and destructive as iniquity. “Whence then is evil, since God who is good made all things good?” Once again, Augustine confronts the limits of his reasoning abilities and imagination. He was limiting his understanding of God by locking his mind on earthly things. Yet the answer to the riddle was contained in his own thought processes.
He would find his answer in Plato. The Platonists taught him a philosophy that could see its own limits. He writes that though their writings did not contain the words of Scripture, they supported its wisdom. They spoke of Christ without knowing His name or knowing that He Who was on high had descended to rescue mankind. The Platonists more fully grasped the relative transcendence of God, as compared to man’s finite and mutable nature. From this, they deduced the limits of reason that restricts itself to the changeable realm of the senses. Augustine writes that they enabled him to appreciate God’s “unchangeable Light shining over that same eye of [his] soul” and mind. This was the light by which he could see and understand the world.
Recognizing these truths as God’s gold, regardless of their pagan origins (Romans 2:14), Augustine assimilated their insights. Most importantly, they harmonized with the Bible’s teachings on good and evil. He writes,
“Then I thought upon those other things that are less than You, and I saw that they neither absolutely are nor yet totally are not: they are, in as much as they are from You: they are not, in as much as they are not what You are. For that truly is, which abides unchangeably … And it became clear to me that corruptible things are good: if they were supremely good they could not be corrupted, but also if they were not good at all they could not be corrupted: if they were supremely good they would be incorruptible, if they were in no way good there would be nothing in them that might corrupt. For corruption damages; and unless it diminished goodness, it would not damage. Thus either corruption does no damage, which is impossible or—and this is the certain proof of it—all things that are corrupted are deprived of some goodness. But if they were deprived of all goodness, they would be totally without being.”
From this, Augustine concluded that evil had no substance, but was merely “a swerving of the will which is turned towards lower things and away from … God, who are the supreme substance: so that it casts away what is most inward to it and swells greedily for outward things.” Augustine was brought to the realization that to find and aim towards God, the supreme Good and Being itself, is an act of the will as much, if not more, than an act of the intellect. From them, he learned that all men pursue the highest good which is existence itself. The modern naturalist would call this the survival mechanism to which all life tends. Evil occurs when this good is pursued wrongly and in a way that leads to destruction by turning away from the Source of existence – the Ground of Being and Great I Am. Goodness prevails when this highest good is pursued by the right and virtuous course. For a man who was chained to his worldly desires, intellectual pride and sexual lust, this was a breakthrough for Augustine.
 Hebrews 4:12, ESV.
 Augustine, Confessions, 2nd ed., trans. F.J. Sheed, ed. Michael P. Foley, 4.14.22.
 G.K. Chesterton, Orthodoxy (Peabody, MA: Hendrickson Publishers, 2006), 49.
 Augustine, Confessions, 2nd ed., trans. F.J. Sheed, ed. Michael P. Foley, 3.4.7.
 Ibid., 3.5.9.
 Chesterton, Orthodoxy, 13: “The poet only asks to get his head into the heavens. It is the logician who seeks to get the heavens into his head. And it is his head that splits.”
 Augustine, Confessions, 2nd ed., trans. F.J. Sheed, ed. Michael P. Foley, 1.4.4.
 G.K. Chesterton, The Everlasting Man (Mineola, NY: Dover Publications, 2007), 92.
 Augustine, Confessions, 2nd ed., trans. F.J. Sheed, ed. Michael P. Foley, 7.1.1.
 Ibid., 7.1.2.
 Ibid., 4.16.30.
 Peter Kreeft, loc. 1211-1212.
 Augustine, Confessions, 2nd ed., trans. F.J. Sheed, ed. Michael P. Foley, 6.3.4.
 Ibid., 6.4.5.
 Ibid., 6.3.4.
 Ibid., 6.4.5.
 Ibid., 7.5.7.
 Ibid., 7.9.16.
 Ibid., 7.12.18.
 Ibid., 7.16.22.