The ride began with a conversation that should have shocked me more than it did.
My passenger spoke openly about his criminal history. Not one offense. Not two. By his own count, dozens. He discussed them with a matter-of-factness that was almost disorienting. There was no dramatic confession. No visible burden. No sense that he was carrying the weight of every decision he had ever made.
As he casually recounted mistakes that could fill pages, I found myself thinking about the comparatively minor moments that have occupied my own mind for years. Not crimes. Not felonies. Just ordinary human mistakes that somehow refuse to leave. The contrast was impossible to ignore.
As he spoke, I noticed something else: I was reacting to his story in a way that he didn't seem to be reacting to his own.
For most of my life, I've been a reader. Not casually, but obsessively. I've read well over 200 novels, perhaps many more. I've spent thousands of hours inhabiting the minds of fictional characters, following their mistakes, understanding their motives, and witnessing the ripple effects of their decisions. Through books, I've lived hundreds of lives that weren't my own.
Maybe that's why this conversation unsettled me.
While my passenger spoke about his past with remarkable ease, I found myself thinking about the strange burden of awareness. Some people seem capable of moving through life without examining every decision they've ever made. Others replay a single mistake for years, dissecting it from every possible angle.
I have always belonged to the second group.
Before I picked him up, the rideshare app displayed a notice instructing drivers not to deviate from the destination entered into the system. There could have been many explanations for that. Some medical transportation programs require direct routes. Certain court-ordered arrangements can restrict where a person is allowed to travel. The truth wasn't mine to know, and I never asked.
What interested me was not the reason itself but what it represented: a life shaped by systems, appointments, supervision, treatment programs, and interventions.
At one point, he shifted in his seat like he was deciding how much to say next.
"I broke my ankle a while back," he said.
I glanced over. "Yeah?"
He nodded. "Walked on it for about a year."
"A year?" I said, before I could stop myself.
He gave a small shrug, like it wasn't something he expected me to understand.
Then he explained how everything had unfolded in pieces. The ankle injury. The delay in treatment. Pain medication that he had been prescribed while waiting for surgery. The way things slowly got worse instead of better. At some point, he mentioned a wound on his leg—he didn't linger on the exact word for it, and I didn't press—but he described it as something that had spread over time.
I remember looking at the road and listening, trying not to fill in too many gaps with my own assumptions.
As rideshare drivers, we end up hearing fragments of people's lives like this. Not the full story, just the parts that come out between directions and traffic lights.
As we drove, he talked about the small farming community he came from, somewhere near Eau Claire, Wisconsin.
According to him, there wasn't much there. Few resources. Few opportunities. Few places to go. Few things to do.
The way he described it, it sounded like the kind of place where everybody knows everybody. The kind of place where life follows familiar patterns because there aren't a lot of other options around.
Then he told me something that stayed with me long after the ride ended.
He said his state had very few treatment centers available. One to three, he estimated. He was surprised by Minnesota. Here, treatment facilities seemed plentiful. Here, there were options. Here, people could find help without traveling extraordinary distances. Here, at least from his perspective, there seemed to be less judgment about the fact that someone might need treatment to recover. Here, asking for help appeared to carry less stigma. Here, recovery felt possible.
As rideshare drivers, we witness a quiet migration that rarely becomes part of public conversation. We pick up people who travel hundreds of miles seeking addiction treatment, mental health services, specialized care, and recovery programs. They come from places where those resources simply don't exist in sufficient numbers.
I'm not saying his hometown is the reason he made the choices he did. Life is more complicated than that.
Still, I kept thinking about what he said. If you grow up in a place with very few opportunities, very few resources, and very few examples of different ways to live, how do you know what else is possible?
Maybe you figure it out on your own.
Maybe someone shows you.
Or maybe you just keep doing what everyone around you is doing because it's the only life you've ever seen.
I don't know if that's what happened to him, but I couldn't stop thinking about it.
And then there was the other question.
How can one person carry dozens of serious offenses with apparent ease while another struggles to forgive themselves for a single mistake?
Part of me wonders whether empathy itself becomes a burden.
After reading hundreds of novels and spending years inhabiting other people's stories, I've become accustomed to looking at situations from multiple perspectives. Every novel asks us to understand someone's choices. Every memoir invites us into another person's struggles. Over time, you start seeing how complicated people really are.
Eventually, some of us become so good at examining other people that we turn that same scrutiny on ourselves.
We replay conversations.
We rethink decisions.
We imagine all the things we should have said differently.
We hold ourselves to standards that we would never impose on a stranger.
Through hundreds of novels, I learned how to understand people.
What I never learned was how to extend that same understanding to myself.
Perhaps that's why the conversation stayed with me.
Not because of the crimes he described.
Not because of the treatment centers.
Not because of the mystery surrounding the warning message attached to the ride.
The conversation stayed with me because it exposed a contradiction I've seen in many people, including myself.
Some people seem unable to forgive themselves for anything.
Others appear able to forgive themselves for almost everything.
Most of us live somewhere in between, carrying old decisions around with us and occasionally pulling them out to examine them one more time.
The passenger never offered a grand lesson. He never asked for sympathy. He never tried to justify his past.
He simply told his story.
And in doing so, he left me with a question I still can't answer:
If understanding other people is supposed to make us more compassionate, why is it often so difficult to show that same compassion to ourselves?
