Why I Go to Prison So Much

Spending twelve-hour days in a prison hanging out with strangers who have done terrible things makes no sense…until you do it.

As a guy who forged his character on books about peak states, leverage, and mastermind groups, prison ministry sounded profoundly dumb to me. I was wired with ideas like “show me your five closest friends and I’ll show you your future,” literally playing in my head in Jim Rohn’s voice. So the plan was to spend a long weekend sitting with convicted criminals? All day? No thanks—I was busy.

It turns out what I wanted to do least was exactly what I needed most.

U.S. military basic training isn’t just expedient—it’s effective. There’s nothing mysterious about adversity building toughness; there’s no other way. What makes boot camps formative is the combination of intensity, duration, and shared discomfort. That mix leaves an imprint on the soul. Prison ministry is the spiritual equivalent. For several days, volunteers are pushed far outside their comfort zones alongside what quickly become thirty of their closest friends.

At my first Kairos training, the mission was drilled into us: listen, listen, love, love. It was good they repeated it. Being fully present—offering someone a level of attention I hadn’t even given my closest family members—was foreign to me. Doing that for a stranger, a man who had likely damaged every relationship in his life on the way to prison, was even more so.

That’s where I learned what agape love actually is. Not conceptually, but experientially. It’s like learning what a carrot tastes like: no abstraction or explanation can substitute for the real thing. You either experience it, or you don’t. The goal wasn’t to fix anyone. It was simply to show love. Many of the men had never known it—no birthday parties, no Christmas mornings, no sense of being seen or wanted. Agape love has no prerequisite beyond recognizing another person as made in God’s image.

I could write a hundred pages about this and still not make the point as clearly as the first day of simply being present.

I came to prison ministry initially through something like Pascal’s Wager. When I seriously explored the big questions of life, I couldn’t find compelling scholarly work disproving Jesus’ existence or dismissing the Bible as an unreliable account of what He said and did. So I read it. Near the end of Matthew 25, Jesus says something unsettling: that feeding the hungry, clothing the poor, and visiting the sick and imprisoned is, in some real sense, serving Him directly. Ignoring those people, He says, has consequences.

The way Jesus spoke about prison struck me. It wasn’t a permanent category for “bad people,” but more like a penalty box—an unsavory, temporary condition, like hunger or illness. I thought, maybe this matters more than I want it to.

Now, I’m arguably addicted to watching agape love work. Kairos Prison Ministry and Jubilee Prison Ministry have guardrails to keep volunteers from burning out. For whatever reason, the people-pleasing gene seems absent in me: I do what I love, or I don’t do it. My kids are grown, my wife isn’t interested in fostering, and I’ve had success in business. So I serve several units a year.

There is nothing I find more compelling than seeing what happens when people are loved without agenda or transaction. (The Texas Department of Criminal Justice doesn’t tolerate dozens of volunteers disrupting operations for days on end unless something real is happening.)

Prison ministry didn’t make me feel heroic. It stripped me of that impulse. Sitting at tables for days with men the world has written off collapses the illusion of status, ego, and moral distance. You realize we are all just human beings. And when you practice being fully present—listening, listening, loving, loving—something quiet but permanent changes in who you become.