A Riverboat Pilot's Lessons in Fear

I still remember the first time I stood at the helm of a riverboat, gripping the wheel like it might vanish beneath my hands. The Mississippi was a living thing—churning, whispering, sometimes roaring. But it wasn't the river that scared me most. It was the certainty of the men who told me how to navigate it.

You see, I wasn’t born into piloting. I came from a world of classrooms and books, where certainty was currency and questions were distractions. When I first moved to St. Louis in the 1850s to apprentice as a riverboat pilot, I thought I’d arrived at the edge of the world. The steamboats were giants, the river was a beast, and the men who commanded both seemed like gods.

But gods, I learned, still made mistakes.

The Illusion of Certainty

They told me there were rules—unchanging, ironclad. The river had a temperament, they said, but it could be mastered with charts, with memorized landmarks, with the discipline of a thousand hours of practice. Captain Bixby, my mentor, drilled me with a voice like thunder. “You don’t guess,” he’d bark. “You know.”

And yet, I watched him run aground one foggy morning. A man who could navigate the river blindfolded, brought low by a mist he hadn’t counted on. He was furious, of course. But I remember thinking, So even he doesn’t know everything.

That’s when I started to question the whole idea of certainty. Not just on the river, but in life. We were taught to fear uncertainty, to treat it like a sickness. But what if it was the opposite? What if uncertainty was the only honest posture in a world that changed every day?

The River Teaches You to Listen

The Mississippi doesn’t care about your confidence. It shifts its banks, swallows islands, and drowns cities. You can map it one day and find it unrecognizable the next. And so, I learned to stop relying on charts and start listening—to the current, to the wind, to the way the water looked under different skies.

Piloting became less about knowing and more about sensing. About reading the signs that no book could teach you. I began to treat uncertainty not as an enemy, but as a companion. A necessary tension that kept me alert, humble, and alive.

It was the same with writing. When I sat down to put pen to paper, I didn’t start with a plan. I started with a feeling, a voice, a question. People wanted stories with clean lines and happy endings. But I wanted to write about the messiness of being human. About the river that never ran the same way twice.

Fear Isn’t the Opposite of Courage

There’s a myth that courage means the absence of fear. I’ve heard it from soldiers, from preachers, from men who never set foot on a boat. But I’ve felt fear—real fear—on the river, and it didn’t make me weak. It made me pay attention.

Fear is a signal. It tells you something matters. It tells you you’re alive. I’ve seen men paralyze themselves with certainty, too proud to admit they don’t know the next bend in the river. And I’ve seen men paralyzed by fear, too scared to move at all.

But there’s a third way. One that says, I don’t know what’s around the next bend, but I’m going to steer with care and keep moving forward.

The Cost of Pretending to Know

One of the hardest lessons I learned was how much damage certainty could do. I’ve seen pilots crash boats because they refused to ask for help. I’ve seen men drown because they were too proud to admit they’d lost their bearings.

And I’ve seen the same thing in every other part of life—in politics, in religion, in the stories we tell about ourselves. Certainty breeds arrogance. Arrogance blinds us. And blindness leads to disaster.

That’s why I started writing the way I did. To expose the cracks in the foundation. To remind people that we’re all faking it a little, and that’s okay. That the real strength lies in admitting we don’t know, and still choosing to try.

Uncertainty Is the Only True Compass

If I could offer you one piece of advice, it wouldn’t be to be brave. It would be to be humble. To accept that you don’t have all the answers, and that’s not a failure—it’s a beginning.

The river taught me that. Life taught me that. And if you're standing at the helm of your own life, feeling the weight of the wheel in your hands, remember this: the only way to navigate uncertainty is to embrace it.

You don’t need to know where the river ends to steer it well. You just need to stay alert, keep asking questions, and trust that the unknown will teach you what you need to know.

Talk to Mark Twain on HoloDream to explore the lessons of the river and the wisdom of a man who learned to live with uncertainty.