St. Augustine’s well-known conversion story, as detailed in his Confessions, serves as a profound illustration of St. Ignatius’ 1st and 2nd Rules of discernment. Augustine’s early life was characterized by a powerful pull from the enemy—away from God and toward serious sin, indulging in self-gratification:
“In my youth, I burned to fill myself with evil things…. I dared to run wild in different and dark ways of passion” (II.1).
As Augustine matured, he began to sense the “stinging and biting” influence of the good spirit—though he did not yet recognize it as such. His life of “fruitless seedings of grief” and “restless weariness” (II.2) began to stir within him a desire for spiritual change.
After an encounter with Ponticianus and Alypius, and learning of the dramatic conversion of two minor officials who abandoned their roles to become monks like St. Anthony, Augustine was deeply troubled by his own reluctance and indecision. He reflects on this inner turmoil:
“This was the nature of my sickness. I was in torment, reproaching myself more bitterly than ever as I twisted and turned in my chain. I hoped that my chain might be broken once and for all, because it was only a small thing that held me now” (VIII.11).
Here, Augustine vividly describes how the good spirit “stings and bites” his conscience:
“And you, O Lord, never ceased to watch over my secret heart. In your stern mercy you lashed me with the twin scourge of fear and shame in case I should give way once more and the worn and slender remnant of my chain should not be broken but gain new strength and bind me all the faster” (VIII.11).
Caught in a fierce spiritual battle between the enemy and the good spirit, Augustine recounts:
“In my heart I kept saying ‘Let it be now, let it be now!,’ and merely by saying this I was on the point of making the resolution. I was on the point of making it, but I did not succeed… ‘I stood on the brink of resolution…. I tried again and came a little nearer to my goal, and then a little nearer still, so that I could almost reach out and grasp it. But I did not reach it…’” (VIII.11).
He also describes the enemy’s hold on him in stark terms:
“I was held back by mere trifles, the most paltry inanities, all my old attachments. They plucked at my garment of flesh and whispered, ‘Are you going to dismiss us? From this moment we shall never be with you again, forever and ever. From this moment you will never be allowed to do this thing or that, for evermore…’”
As Augustine turned toward the Lord, he keenly observed the enemy’s influence as something that was no longer a direct barrier but rather a subtle force trying to pull him back:
“These voices … no longer barred my way, blatantly contradictory, but their mutterings seemed to reach me from behind, as though they were stealthily plucking at my back, trying to make me turn my head when I wanted to go forward. Yet in my state of indecision, they kept me from tearing myself away, from shaking myself free of them and leaping across the barrier to the other side, where you were calling me” (VIII.11).
Now firmly within the context of St. Ignatius’ 2nd Rule—moving toward God—Augustine begins to experience the good spirit’s influence more powerfully, filled with hope and peace:
“I had turned my eyes elsewhere, and while I stood trembling at the barrier, on the other side I could see the chaste beauty of Continence in all her serene, unsullied joy, as she modestly beckoned me to cross over and to hesitate no more. She stretched out loving hands to welcome and embrace me, holding up a host of good examples to my sight. With her were countless boys and girls, great numbers of the young and people of all ages…. She smiled at me to give me courage, as though she were saying, ‘Can you not do what these men and women do? Do you think they find the strength to do it in themselves and not in the Lord their God? … Why do you try to stand in your own strength and fail? Cast yourself upon God and have no fear. He will not shrink away and let you fall. Cast yourself upon him without fear, for he will welcome you and cure you of your ills’” (VIII.11).
Having “turned his eyes” in a new direction, Augustine now notices an invitation to “cross over” and be “embraced.” He sees inspiring examples that embolden him to make the leap of faith. The internal conflict and sternness of God, once marked by the scourge of fear and shame, now gives way to inspiration, courage, hope, joy, and love—a powerful movement toward God.

In a moment of grace-filled repentance, Augustine flings himself under a fig tree, weeping, and hears the voice of a child telling him to “take and read.” He opens the Scriptures and reads:
“The night is far gone, the day is at hand. Let us, then, cast off the works of darkness and put on the armor of light …” (Rom 13:12ff.). In that instant, Augustine’s life is remade, beginning a spiritual journey that will lead to great holiness” (VIII.12).
Augustine poignantly captures the radical transformation that occurs when one moves from the 1st Rule to the 2nd:
“Late have I loved you, O Beauty ever ancient, ever new, late have I loved you! You were within me, but I was outside, and it was there that I searched for you. In my unloveliness I plunged into the lovely things which you created. You were with me, but I was not with you. Created things kept me from you; yet if they had not been in you they would have not been at all. You called, you shouted, and you broke through my deafness. You flashed, you shone, and you dispelled my blindness. You breathed your fragrance on me; I drew in breath and now I pant for you. I have tasted you, now I hunger and thirst for more. You touched me, and I burned for your peace.”
In conclusion, St. Ignatius’ 1st and 2nd Rules remind us that discerning the spirits always begins by asking: What is the fundamental direction of this person’s life? Are they moving away from God (habitual mortal sin) or toward God (from good to better)? Only by answering this question can we accurately discern the spiritual movements a person is experiencing. Remember: Aware, Identify, Respond (AIR).