Privilege and Redemption: How Grace Reaches the Elite

Editor’s note – Daryl Wilson met a stranger on Route 66 and saw his own history reflected back: prep school, privilege, and a search that led both men toward sin before it led toward grace. He tells it as a personal essay, not a sermon. BCW runs it because the question underneath applies well past one trail: does advantage that shields us from consequences also shield us from God? Scripture answers that question directly.

A Meeting on the Road

I met a man on the road last spring when I was driving to California to work in a hospital in San Francisco. Like me, he had sinned. Spent much of his life in sin, in fact, just like me.

The road that year was a literal road for me and for him, as well as a figurative one. Divorced in January, I found myself on historic Route 66 in Grants, New Mexico, in April. Grants is a little town that, as a tourist trap, has seen better days.

There was a hostel for $25 a night. Wanting to save, I booked a bed online. It was a couple of buildings in a dry, pebbly, pink yard. There were three dudes in front of the little house, grilling steaks. I got into a conversation with them and learned they were hiking the Transcontinental Trail, a patchwork of rural and urban trails, roadways, sidewalks, and driveways. Advanced wayfinding, I was told, for people who had already done the Appalachian Trail and the Pacific Crest Trail and were seeking greater challenges.

His trail name was Ranger.

I got the sense I was not going to get his given name. He said he was a carpenter.

He was, in many ways, on the same road I was on. We knew a couple of the same people from high school. And by high school I mean prep school: boarding school. Eastern elite prep school. Preppies. Ivy covered walls, coat, and tie at dinner. That world.

We came from the same cloth: about the same age, graduated from school in the same decade. We could have been brothers. In fact, we were brothers, of a type: a brotherhood of the times, of the ethos of the day, and also the spirit of the search.

In talking to him, it was clear that he had found a redemption on the trail and a new life.

He was making better choices now in middle life. He wished he had been wiser in his youth.

The Weight of Privilege

Some vulnerable young men take on arrogance like a fancy coat. This is the wished-for security of privilege, the manipulation of a world that offers the tools of education and knowledge and lets us have a shot. In many cases, we overstepped our privileges and erred in relationships, in satisfying our desires, in callousness and hardness of heart.

He had gone to another country in South America for some years and eventually found his way back to America and to the calling of working with his hands. He had stopped sinning.

I am not sure what part Jesus played in his journey toward healing. We didn’t discuss it. I presume Jesus wasn’t far away from his heart. I think Jesus stands near to the hearts of those who repent, listening for the right words, listening for His name.

Editor’s note – Wilson admits he doesn’t know what part Jesus played in Ranger’s turnaround, and that honesty is instructive. We rarely see exactly how grace works in someone else’s story; we are only shown its fruit.

Something had opened his eyes and he had found peace on the trail and in his life. Something had filled the void.

Why Privilege Leads Away from God

I reflected: what had caused the void? Why does a world of privilege often lead to arrogance and rejection of God and the wellsprings of life?

Some of this is obvious: with more of the illusions of the world in a thick layer, it is harder to see your way through to truth. With more of the temptations of the world already within your grasp, the ability to walk a straight path and withstand the entreaties of the opponent is tested sorely. Many fall.

The Path Back to Grace

But after that, for many, there is also a redemption: guilt gives way to action, a time in purgatory. A time of purification can lead many to a more righteous path. Guilt makes room for forgiveness. Contempt gives way to compassion. Pain and fear open a door that leads to understanding.

Editor’s note – Guilt is not the goal; repentance is. Guilt that only produces shame leaves a person stuck, but guilt that drives someone toward God, as it did for Ranger, is conviction doing its proper work.

For many of us, God’s grace offers us a chance. He sends us angels to guide us. Many times, the passage of time and the experience of errors and their consequences offer insight.

“To whom is given much, much is asked,” Jesus said in Luke 12:48.

In one perspective, even these forays into sin are a gift and a curse of privilege: there is some insulation from the consequences of sin. There is a launchpad for the experience of the world and its devils and angels. Many times, foolishness is its own teacher. Experience, eventually, is not the experience of the world, but the experience of what is in the heart.

It is also a numbers game: the more times one tries, the more times one fails. But each time one rises and walks the path again is another chance to learn, and perhaps, another chance to walk within righteousness. The many pathways of the world beckon; the more steps that are taken, the more one may find the guidance of the angels. Jesus, the Advocate, the Shepherd, stands ready to walk with us.

A Carpenter Leading Men to the Light

Ranger walked the trail now, and I bid him safe travels. For him there had been a good ending to the journey, and he now acted as an example and an inspiration to many: There is a way out of sin. The training of the academy, of education and privilege, had ultimately shaped him into a bearer of the true emblem of all such preparation: not money, not power on earth, but as a lowly carpenter to lead men into the light.

A Word from the Editor
Every advantage we’re given – money, education, a good name – is a stewardship, not a shield. Luke 12:48 makes that plain: much is given, much is required. The harder word is Ephesians 2:8: even repentance is grace, not achievement. Christ is already walking whatever road we’re on, waiting for whoever turns toward Him.

Editor Comment: You show how God's grace can enter the very privilege we once spent on ourselves, and that grace turns guilt into repentance instead of despair. Ending on Ranger's trade as a carpenter shows a man remade for humble service instead of status, and readers will recognize that trade as a picture of grace at work in ordinary life.