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The problem, Augustine came to believe, is that if you think you can organize your own salvation you are magnifying the very sin that keeps you from it. To believe that you can be captain of your own life is to suffer the sin of pride.

What is pride? These days the word “pride” has positive connotations. It means feeling good about yourself and the things associated with you. When we use it negatively, we think of the arrogant person, someone who is puffed up and egotistical, boasting and strutting about. But that is not really the core of pride. That is just one way the disease of pride presents itself.

By another definition, pride is building your happiness around your accomplishments, using your work as the measure of your worth. It is believing that you can arrive at fulfillment on your own, driven by your own individual efforts.

Pride can come in bloated form. This is the puffed-up Donald Trump style of pride. This person wants people to see visible proof of his superiority. He wants to be on the VIP list. In conversation, he boasts, he brags. He needs to see his superiority reflected in other people’s eyes. He believes that this feeling of superiority will eventually bring him peace.

That version is familiar. But there are other proud people who have low self-esteem. They feel they haven’t lived up to their potential. They feel unworthy. They want to hide and disappear, to fade into the background and nurse their own hurts. We don’t associate them with pride, but they are still, at root, suffering from the same disease. They are still yoking happiness to accomplishment; it’s just that they are giving themselves a D– rather than an A+. They tend to be just as solipsistic, and in their own way as self-centered, only in a self-pitying and isolating way rather than in an assertive and bragging way.

One key paradox of pride is that it often combines extreme self-confidence with extreme anxiety. The proud person often appears self-sufficient and egotistical but is really touchy and unstable. The proud person tries to establish self-worth by winning a great reputation, but of course this makes him utterly dependent on the gossipy and unstable crowd for his own identity. The proud person is competitive. But there are always other people who might do better. The most ruthlessly competitive person in the contest sets the standard that all else must meet or get left behind. Everybody else has to be just as monomaniacally driven to success. One can never be secure. As Dante put it, the “ardor to outshine / Burned in my bosom with a kind of rage.”

Hungry for exaltation, the proud person has a tendency to make himself ridiculous. Proud people have an amazing tendency to turn themselves into buffoons, with a comb-over that fools nobody, with golden bathroom fixtures that impress nobody, with name-dropping stories that inspire nobody. Every proud man, Augustine writes, “heeds himself, and he who pleases himself seems great to himself. But he who pleases himself pleases a fool, for he himself is a fool when he is pleasing himself.”16

Pride, the minister and writer Tim Keller has observed, is unstable because other people are absentmindedly or intentionally treating the proud man’s ego with less reverence than he thinks it deserves. He continually finds that his feelings are hurt. He is perpetually putting up a front. The self-cultivator spends more energy trying to display the fact that he is happy—posting highlight reel Facebook photos and all the rest—than he does actually being happy.

Augustine suddenly came to realize that the solution to his problem would come only after a transformation more fundamental than any he had previously entertained, a renunciation of the very idea that he could be the source of his own solution.

Elevation

Augustine later wrote that God sprinkled bitterness and discontent over his life to draw him toward God. “The greater I got in age, the worse I got in emptiness, as I could not conceive of any substance except the kind I saw with these eyes.” Or, as he most famously put it, “our hearts are restless until we rest in Thee.”

Augustine’s pain during his years of ambition, at least as he describes it later, is not just the pain of someone who is self-centered and unstable. It is the pain of someone who is self-centered and unstable but who has a deep sensation that there is a better way to live, if only he could figure out what it is. As other converts have put it, they are so rooted in God that even when they haven’t found God they feel the lack. They are aware of a divine absence, which picks at them from the inside, and that absence is evidence of a presence. Augustine had an inkling of what he needed in order to feel peace, but still, perversely, was unmotivated to actually travel there.

To move from a fragmentary life to a cohesive one, from an opportunistic life to a committed life, it is necessary to close off certain possibilities. Augustine, like most of us in this situation, didn’t want to close his options and renounce the things that made him feel good. His natural inclination was to think his anxieties could be solved if he got more of what he desired, not less. So he hung on an emotional precipice between a religious life he was afraid to sacrifice for and a secular one he detested but would not renounce. He commanded himself to decenter himself and put God at the center of his life. But he refused to obey himself.

He worried about his reputation. He worried he’d have to give up sex, sensing that for him, celibacy would be a necessary part of a religiously devoted life. “This controversy in my heart was self against self only.” Looking back, he recalled, “I was in love with the idea of the happy life, but I feared to find it in its true place and I sought for it by running away from it.”

His general solution was to delay. Make me virtuous—but not yet.

In the Confessions, Augustine paints the scene when the delay finally ended. He was sitting in a garden talking with a friend, Alypius, who told him some stories about monks in Egypt who gave up everything to serve God. Augustine was amazed. The people who were not part of the elite educational system were out doing amazing things while the graduates of that system lived for themselves. “What ails us?” Augustine cried. “The unlearned start up and take heaven by force and we, with this our learning, but without heart, wallow in flesh and blood.”

In this fever of doubt and self-reproach, Augustine stood up and strode away while Alypius gazed on in stunned silence. Augustine began pacing around the garden, and Alypius got up and followed him. Augustine felt his bones crying out to end this self-divided life, to stop turning and tossing this way and that. He tore at his hair, beat his forehead, locked his fingers and hunched over, clasping his knee. It seemed as if God was beating on his insides, inflicting a “severe mercy,” redoubling the lashes of fear and shame that afflicted him. “Be it done now, be it done now,” he cried to himself.

But his worldly desires would not give up so easily. Thoughts jumped into his head. It was as if they were plucking at his garments. “Are you going to cast us off? You’ll never experience our pleasures ever again?” Augustine hesitated, wondering, “Do I really think I can live without these pleasures?”

Then there appeared in his mind a thought, the ideal of dignified chastity and self-control. In the Confessions, he dresses up this thought in metaphorical terms, as a vision of a woman, Lady Continence. He does not describe her as an ascetic, puritanical goddess. On the contrary, she is an earthy, fecund woman. She’s not renouncing joy and sensuality; she’s offering better versions. She describes all the young men and women who have already renounced the pleasures of the world for the pleasures of the faith. “Can’t you do what they did?” she asks. “Why are you standing apart in yourself?”