A sailor, a pilot, and a president walk into the unknown

by | Nov 7, 2026 | Reading, Writing | 0 comments

I’ve been reading about people who should be dead.

Not in a morbid way. (Okay, maybe a little.) It started with one book about a shipwreck, and then, the way these things go, I couldn’t stop. Three books later, I’m convinced they’re all secretly about writing.

Bear with me.

The first was David Grann’s The Wager. In 1740, a British warship sets off on a secret mission to run down a Spanish galleon stuffed with treasure. Instead, it wrecks on a scrap of rock off the coast of Patagonia, the kind of place where it rains sideways and nothing edible grows. The men are starving. Scurvy is having its way with them. (God, check out scurvy, it’s absolutely horrifying!) By all rights, that island should have been their grave.

Instead, they take the ship’s longboat, lengthen it with timber salvaged from the wreck, and sail it nearly 3,000 miles through some of the most vicious water on the planet. More than a hundred days. Thirty skeletal men wash up on the coast of Brazil and are greeted as heroes.

Then, six months later, three more castaways stagger ashore in Chile with a very different story. Those heroes? Mutineers.

Which means surviving the island was only half the job. Once they got home, every one of them had to survive the telling. The men wrote and published their accounts, each version racing the others to become the truth. Whoever told the story best got to decide what had happened.

(Hold that thought.)

The second was Antoine de Saint-Exupéry’s Wind, Sand and Stars. Before he ever wrote The Little Prince, Saint-Exupéry flew mail across the Sahara and over the Andes in planes that were essentially lawn chairs with an engine bolted on. No radar. Spotty radio. Maps with large blank spaces on them. Pilots went down and simply didn’t come back. (Apparently, this was built into the postal business model.)

His friend Henri Guillaumet crashed in the Andes in the dead of winter and walked for five days through snow and ice with no food and no gear. When he wanted to lie down and let the cold take him (which, apparently, feels lovely right up until it doesn’t), he thought about his wife. If he died where he lay, his body might not be found until the thaw, and she couldn’t collect the insurance. So he got up and walked toward a rock where he’d be visible. He kept walking for her. Then he just kept walking.

Saint-Exupéry himself crashed in the Libyan desert with his mechanic. They wandered for days without water, hallucinating, their bodies shutting down, until a Bedouin on a camel found them. (And we worry about spotty wi-fi access.) He lived to write about it, in some of the most beautiful prose ever produced on the subject of nearly dying.

The third was Candice Millard’s The River of Doubt. In 1912, Theodore Roosevelt ran for president again and lost. Humiliatingly. His response? Not a nice long sulk, which is what I’d opt for. He went looking for the hardest thing he could find, and found it: an unmapped tributary of the Amazon no outsider had ever traveled. With his son Kermit and the Brazilian explorer Cândido Rondon, he set off downriver into the unknown. Rapids smashed their canoes. Food ran out. One man drowned. Another was murdered by one of their own. Roosevelt’s leg became infected, his fever spiked, and he begged the others to leave him behind. He carried a vial of morphine for exactly that purpose.

They didn’t leave him. He came out the other side, and the river now bears his name.

(BTW, the Amazon jungle makes Australia look positively innocuous.If you’ve read Bill Bryson’s In a Sunburned Country, you’ll understand.)

I’ve done my share of stupid things on mountains, but I always had a route. Someone had been there before me. Someone knew there was a summit up there, and roughly how to get to it. These people had nothing of the sort. Nobody had a goddamned map. Roosevelt’s whole job was to draw one.

So here’s what I keep circling back to.

We treat starting a book as though it might kill us. We want certainty before we begin. We want to know the outline is right, that the idea is original, that we have enough to say, that someone will publish it, that someone will read it, that it’ll be good. And until we have all of that, we stay on the beach and polish our boots.

But nobody in these three books had certainty. Not one. What they had was the next rapid, the next hundred yards of snow, the next plank of salvaged wood. They found their way by going. And here’s the kicker: the not knowing is precisely what made them worth listening to. Nobody would read a book about a man who paddled down a well-charted river and had a lovely time. (Although, A River Runs Through It comes kinda close.)

Your readers are no different. They don’t want to hear from someone who had it all figured out on day one. They want the person who got lost, got scared, got it wrong, and found the way through anyway. Your detours are your authority. The messy middle is the reason anyone will trust you.

You don’t get the map before the trip. The map is what you make on the trip. Your outline will change. Chapter three will turn into chapter seven, and then disappear entirely. That’s not failure. That’s cartography.

You build the boat out of whatever washed up. The notes in your phone, the talk you gave last spring, the half-finished draft you abandoned three years ago. That’s your salvaged timber. It’s enough to get started.

When you want to lie down in the snow, think about who’s waiting for you. Guillaumet walked for his wife. You’re writing for the reader who’s stuck exactly where you once were and doesn’t yet know there’s a way out.

And remember that the story you tell afterward matters. The Wager survivors understood that the journey and the account of the journey were two separate acts of survival. That’s what your book is. You went somewhere most people won’t go, and you came back to tell us what it was like.

Let’s keep a little perspective, too. The worst thing that happens if you start your book is a bad first draft. Nobody is going to court-martial you over a clunky chapter. No one’s going to leave you on a riverbank with a vial of morphine. You’ll just have to revise.

Every one of these people came out a different person than the one who went in. That’s the deal. That’s always been the deal.

Roosevelt didn’t know where the river went.

That was the point of going.

And yes, this whole post is a recommended reading list. You’re welcome.

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