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Casual readers of the Confessions have always wondered why Augustine got so worked up over a childhood prank. I used to think that the theft of the pears was a stand-in for some more heinous crime the teenage boys committed that night, like molesting a girl or some such thing. But for Augustine, the very small purposelessness of the crime is part of its rotten normality. We commit such small perversities all the time, as part of the complacent order of life.

His larger point is that the tropism toward wrong love, toward sin, is at the center of the human personality. People not only sin, we have a weird fascination with sin. If we hear that some celebrity has committed some outrageous scandal, we’re kind of disappointed when it turns out the rumor isn’t really true. If you leave sweet children to their own devices with nothing to do, before long they will find a way to get into trouble. (The British writer G. K. Chesterton once observed that the reality of sin can be seen on a lovely Sunday afternoon when bored and restless children start torturing the cat.)

Even sweet institutions, like camaraderie and friendship, can be distorted if they are unattached to a higher calling. The story of the stealing of the pears is also the story of a rotten friendship. Augustine realizes he probably wouldn’t have done it if he had been alone. It was the desire for camaraderie, for mutual admiration, that egged the boys on into doing what they did. We so fear exclusion from the group that we are willing to do things that we would find unconscionable in other circumstances. When unattached to the right ends, communities can be more barbarous than individuals.

God’s Presence

The second large observation that flows from Augustine’s internal excavation is that the human mind does not contain itself, but stretches out toward infinity. It’s not only rottenness Augustine finds within, but also intimations of perfection, sensations of transcendence, emotions and thoughts and feelings that extend beyond the finite and into another realm. If you wanted to capture Augustine’s attitude here, you might say that his thoughts enter and embrace the material world, but then fly up and surpass it.

As Reinhold Niebuhr put it, Augustine’s study of memory led him to the “understanding that the human spirit in its depth and heights reaches into eternity and that this vertical dimension is more important for the understanding of man than merely his rational capacity for forming general concepts.”14

The path inward leads upward. A person goes into himself but finds himself directed toward God’s infinity. He senses the nature of God and his eternal creation even in his own mind, a small piece of creation. Centuries later, C. S. Lewis would make a related observation: “In deepest solitude there is a road right out of the self, a commerce with something which, by refusing to identify itself with any object of the senses, or anything whereof we have biological or social need, or anything imagined, or any state of our minds, proclaims itself purely objective.” We are all formed within that eternal objective order. Our lives cannot be understood individually, abstracted from it. Sin—the desire to steal the pears—seems to flow from the past through human nature and each individual. At the same time, the longing for holiness, the striving upward, the desire to live a life of goodness and meaning, are also universal.

The result is that people can understand themselves only by looking at forces that transcend themselves. Human life points beyond itself. Augustine looks inside himself and makes contact with certain universal moral sentiments. He is simultaneously aware that he can conceive of perfection, but it is also far beyond his powers to attain. There must be a higher power, an eternal moral order.

As Niebuhr put it, “man is an individual but he is not self-sufficing. The law of his nature is love, a harmonious relation of life to life in obedience to the divine center and source of his life. This law is violated when man seeks to make himself the center and source of his own life.”

Reform

Augustine began to reform his life. His first step was to quit the Manichees. It no longer seemed true to him that the world was neatly divided into forces of pure good and pure evil. Instead, each virtue comes with its own vice—self-confidence with pride, honesty with brutality, courage with recklessness, and so on. The ethicist and theologian Lewis Smedes, expressing an Augustinian thought, describes the mottled nature of our inner world:

Our inner lives are not partitioned like day and night, with pure light on one side of us and total darkness on the other. Mostly, our souls are shadowed places; we live at the border where our dark sides block our light and throw a shadow over our interior places…. We cannot always tell where our light ends and our shadow begins or where our shadow ends and our darkness begins.15

Augustine also came to believe that the Manichees were infected with pride. Having a closed, all-explaining model of reality appealed to their vanity; it gave them the illusion that they had intellectually mastered all things. But it made them cold to mystery and unable to humble themselves before the complexities and emotions that, as Augustine put it, “make the heart deep.” They possessed reason, but no wisdom.

Augustine hung between worlds. He wanted to live a truthful life. But he wasn’t ready to give up his career, or sex, or some of his worldly pursuits. He wanted to use the old methods to achieve better outcomes. That is to say, he was going to start with the core assumption that had always been the basis for his ambitious meritocratic life: that you are the prime driver of your life. The world is malleable enough to be shaped by you. To lead a better life you just have to work harder, or use more willpower, or make better decisions.

This is more or less how many people try to rearrange their life today. They attack it like a homework assignment or a school project. They step back, they read self-help books like The Seven Habits of Highly Effective People. They learn the techniques for greater self-control. They even establish a relationship with God in the same way they would go after a promotion or an advanced degree—by conquest: by reading certain books, attending services regularly, practicing spiritual disciplines such as regular prayer, doing their spiritual homework.

Pride

But eventually Augustine came to believe that you can’t gradually reform yourself. He concluded that you can’t really lead a good life by using old methods. That’s because the method is the problem. The crucial flaw in his old life was the belief that he could be the driver of his own journey. So long as you believe that you are the captain of your own life, you will be drifting farther and farther from the truth.

You can’t lead a good life by steering yourself, in the first place, because you do not have the capacity to do so. The mind is such a vast, unknown cosmos you can never even know yourself by yourself. Your emotions are so changeable and complex you can’t order your emotional life by yourself. Your appetites are so infinite you can never satisfy them on your own. The powers of self-deception are so profound you are rarely fully honest with yourself.

Furthermore, the world is so complex, and fate so uncertain, that you can never really control other people or the environment effectively enough to be master of your own destiny. Reason is not powerful enough to build intellectual systems or models to allow you to accurately understand the world around you or anticipate what is to come. Your willpower is not strong enough to successfully police your desires. If you really did have that kind of power, then New Year’s resolutions would work. Diets would work. The bookstores wouldn’t be full of self-help books. You’d need just one and that would do the trick. You’d follow its advice, solve the problems of living, and the rest of the genre would become obsolete. The existence of more and more self-help books is proof that they rarely work.