On the Road with Saint Augustine: A Real-World Spirituality for Restless Hearts

Rituals are not solutions. They don’t “fix” things. They are how we live with what we can’t fix, channels for facing up to our finitude, the way we try to navigate this vale of tears in the meantime. But precisely for that reason they can also be conduits of hope and rhythms of covenant.

The question isn't whether you're going to believe, but who; it's not merely about what to believe, but who to entrust yourself to. Do we really think humanity is our best bet? Do we really think we are the the answer to our problems, we who've generated all of them? The problem with everything from Enlightenment scientism to mushy Eat-Pray-Love-ism is us. If anything looks irrational, it's the notion that we are our own best hope.

You can still be living in your childhood bedroom and have departed for a distant country. You can play the role of the “good son” with a heart that roams in a twilight beyond good and evil. You can even show up to church every week with a voracious appetite for idols. Not all prodigals need a passport.

The question isn’t whether you’re going to believe, but who; it’s not merely about what to believe, but who to entrust yourself to. Do you really want to trust yourself? Do we really think humanity is our best bet? Do we really think we are the answer to our problems, we who’ve generated all of them?

My yoke is kindly and my burden light” (Matt. 11:30). “Every other burden oppresses you and feels heavy, but Christ’s burden lifts you up; any other burden is a crushing weight, but Christ’s burden has wings.”33 Not only can you make it home; you can fly.

Attainment is a goddess who quickly turns a cold shoulder.

Free choice is sufficient for evil, but hardly for good.

When you've realized that you don't even know yourself, that you're an enigma to yourself, and when you keep looking inward only to find an unplumbable depth of mystery and secrets and parts of yourself that are loathsome, then Scripture isn't received as a list of commands: instead, it breaks into your life as a light from outside that shows you the infinite God who loves you at the bottom of the abyss.

What if the human condition was understood not as Odyssean (a neat and tidy return) or Sisyphean (learning to get over your hope for home), but as being like the experience of a refugee? What if being human means being a cosmic émigré—vulnerable, exposed, unsettled, desperate, looking for a home I’ve never been to before? The longings of the refugee—to escape hunger, violence, and the quotidian experience of being bereft in order to find security, flourishing, and freedom—are good and just precisely because they are so deeply human. They even signal something about our spiritual condition: that our unshakable hopes of escaping a bereftness of the soul and finding the security of a home are not absurd. The exhaustion we experience from perpetually seeking, the fatigue of trying to live as if “the road is life,” the times we crumple onto the road just wishing someone could find us and take us home—the persistence of this hope almost makes us wonder if it could be realized.

Sometimes plausibility is pegged to a person. The turning point for Augustine was not an argument; it was Ambrose. What Ambrose said, what he taught and preached, was not insignificant. But what made a dent on Augustine's imagination was Ambrose's very being--what he represented in his way of life. Ambrose was a living icon of someone who integrated assiduous learning with ardent Christian faith. If to that point, based on his childhood experience, Augustine had concluded that Christians were simple, backward, and naive, the encounter with Ambrose was the destabilising experience of meeting someone with intellectual firepower who was also following Jesus. Even more than that, it was Ambrose's hospitality that prompted Augustine to reconsider the faith he'd rejected as unenlightened. What ultimately shifted Augustine's plausibility structures? Love.

We cultivate indifference as a cocoon. We make irony a habit because the safety of maintaining a knowing distance works as a defense. If you can’t find what matters, conclude that nothing matters. If the hunger for home is always and only frustrated, decide “the road is life.

Resting in the love of God doesn’t squelch ambition; it fuels it with a different fire. I don’t have to strive to get God to love me; rather, because God loves me unconditionally, I’m free to take risks and launch out into the deep.

It is a terrible and terrifying thing to know what you want to be and then realize you’re the only one standing in your way—to want with every fiber of your soul to be someone different, to escape the “you” you’ve made of yourself, only to fall back into the self you hate, over and over and over again.

This is not a book about Augustine. In a way, it’s a book Augustine has written about you. It’s a journey with Augustine as a journey into oneself. It’s a travelogue of the heart. It’s a road trip with a prodigal who’s already been where you think you need to go.

In Jack Kerouac’s iconic novel On the Road, the narrator Sal Paradise plays chronicler to the antics of the star of the story, Dean Moriarty, who is really the exemplar, the hero, the model. So just call me Sal. I’ve been on a ride with Augustine. Here’s what I’ve seen; here’s what he’s shown me (about myself); here’s why you might consider coming along.

If Augustine spent half his life battling the heresy of Pelagianism—the pretension that the human will was sufficient to choose its good—it’s because he saw it as the great lie that left people enchained to their dissolute wills. And no one is more Pelagian than we moderns.

The notion of a governing narrative that is not your own feels like signing over the rights to your life—which it is! But for Augustine, being enfolded in God’s story in Scripture was not an imposition but a liberation. When you’ve realized that you don’t even know yourself, that you’re an enigma to yourself, and when you keep looking inward only to find an unplumbable depth of mystery and secrets and parts of yourself that are loathsome, then Scripture isn’t received as a list of commands: instead, it breaks into your life as a light from outside that shows you the infinite God who loves you at the bottom of the abyss.

Do we tell ourselves we’re “just going” in order to guard against the disappointment of never arriving? Do we call the road “home” to avoid the pain of never being welcomed?

How to die is a question of how to live, but how to live is a matter of knowing how to love: how to find a love that isn't haunted by fear, a love that is stronger than death - figuring out how to love rightly and live lightly with all the mortal beauties of creation without despising or resenting their mortality either...The hope of eternal life does not efface the desire to live - it is the fulfillment of the desire to live, to live in a way that we can never lose what we love.

The hope of enduring love, a love stronger than death, is not some natural immortality; it is a life bought by the death of God, the resurrection of the Crucified, which now yields hope as a spoil of victory over the grave.

The wayward son is not defined by his prodigality but by the welcome of a father who never stopped looking, who is ever scanning the distance, and who runs to gather him up in an embrace. God is not tapping his foot judgmentally inside the door as you sneak in, crawling over the threshold in shame. He’s the father running toward you, losing his sandals on the way, his robes spilling off his shoulders, with a laughing smile whose joy says, “I can’t believe you came home!” This is what grace looks like.

They broke up into pairs, and the other two wandered afield and came across a small, humble house that was home to some monks. Welcomed inside, one of Ponticianus’s friends, scanning the shelves, picked up The Life of Antony, a biography of the Egyptian monk by Athanasius. He was immediately pulled in by the book and “set on fire.” Suddenly he was filled with holy love and sobering shame. Angry with himself, he turned his eyes on his friend and said to him: “Tell me, I beg of you, what do we hope to achieve with all our labours? What is our aim in life? What is the motive of our service to the state? Can we hope for any higher office in the palace than to be Friends of the Emperor? And in that position what is not fragile and full of dangers? How many hazards must one risk to attain a position of even greater danger? And when will we arrive there? Whereas, if I wish to become God’s friend, in an instant I may become that now.”19 What is our aim in life? What are we aiming for when we aim our lives at some aspiration? The question isn’t whether we aim our lives. Our existence is like an arrow on a taut string: it will be sent somewhere. It’s not a matter of quelling ambition, of “settling,” as if that were somehow more virtuous (or even possible). The alternative to disordered ambition that ultimately disappoints is not some holy lethargy or pious passivity. It’s recalibrated ambition that aspires for a different end and does so for different reasons. What

To desire the aid of grace is the beginning of grace.

Trust is the oxygen of human society, Augustine says, and believing the testimony of others is at the very heart of the scientific enterprise

A friend is not an enabler; love doesn’t always look like agreement.

But I think she misses one of the ways fathers want to love their sons—by sharing wisdom, giving some guidance, owning fatherhood by offering insight for living.

Here’s a Christianity to consider before you stop believing. Augustine might make Christianity plausible again for those who’ve been burned—who suspect that the “Christianity” they’ve seen is just a cover for power plays and self-interest, or a tired moralism that seems angry all the time, or a version of middle-class comfort too often confused with the so-called American Dream.

When we leave home looking for happiness, we’re in search of the self we never knew.

Platonism offered a ladder to (re)connect God and humanity; in Christianity, God climbs down.

WHOSE HEART ISN’T prodigal? One of the gifts Augustine offers is a spirituality for realists. Conversion is not a “solution.” Conversion is not a magical transport home, some kind of Floo powder to heaven. Conversion doesn’t pluck you off the road; it just changes how you travel.