Musings, Meanderings, & Loops · Essay
September 10, 2026
There is a little essay from 1899 that I have never been able to shake, and I want to be honest about both of the things it has done to me. It has indicted me, fairly. And it has been used, in rooms I have worked in, as a stick — and I did not see the second thing clearly until I went back this month and learned what actually happened in Cuba.
The essay is Elbert Hubbard's "A Message to Garcia." He wrote it in a single hour on Washington's Birthday, after his son remarked over dinner that the real hero of the Spanish-American War was not any general but a lieutenant named Rowan. In Hubbard's telling: the President needed to reach Calixto García, leader of the Cuban insurgents, somewhere in the mountain fastness of the island — nobody knew where. Rowan was handed a letter. He sealed it in an oilskin pouch, strapped it over his heart, landed by night off the coast, disappeared into the jungle, and three weeks later came out the other side, message delivered. And — this is the part Hubbard fell in love with — he did not ask a single question. He did not ask where García was. He took the letter and figured it out.
Hubbard turned that into a hymn for the person who can be handed a task and trusted with it — and a lament about everyone else: the slipshod assistance, the foolish inattention, the half-hearted work of people who cannot act unless every step is specified. The world cries out, he says, for the man who can carry a message to Garcia.
Let me take my medicine before I complicate the story, because the essay's claim on me is legitimate and I do not want to write my way out of it.
There have been letters in my life that I did not carry. Times I was handed something genuinely mine — the mandate real, the trust real — and I waited. Waited for clarity that was mine to create, asked questions that were actually requests for permission, treated nobody told me where García was as a reason instead of recognizing it as the assignment. Some of the failures I regret most were not failures of ability. They were failures to push off from the dock — to accept that figuring it out was not an obstacle standing in front of the job but the entire job. Hubbard would have had my number, and when I first read him, he did. That sting was the sting of a true thing.
So the essay's virtue is real. Hold that. Now come look at what happened to it.
"A Message to Garcia" became one of the most widely distributed pieces of writing in American history, and the interesting question is: distributed by whom, to whom?
George Daniels of the New York Central Railroad ordered a hundred thousand copies almost immediately, then reprinted it in lots of half a million — for his employees. Wanamaker's department store handed it out. The Navy handed it out. Corporations pressed it into millions of workers' hands for decades. Notice the direction. The essay traveled downward, always downward, from management to labor, boss to subordinate — a scolding about initiative, delivered by institutions, to the people under them. It is hard to find a record of it ever once being handed up.
And the timing tells you why. Hubbard wrote in 1899, in the raw years after the Pullman Strike, and scholars have since called the essay what it functioned as: a managerial manifesto — a parable that relocated every workplace failure into the worker's character, and dressed obedience up as heroism. Labor voices said so at the time; one printer publicly called it an insult to working people. The bosses who bought it by the boxcar were not celebrating initiative. They were purchasing a sermon that said whatever is wrong here is wrong with you.
I have been in rooms run on that sermon. I suspect you have too. The meeting where you are not permitted to speak because you have not accrued the status to be audible. The manager who assigns the message and then narrates every step of the route, until the assignment is not a letter but a leash. Organizations that say they are starving for Rowans while operating a system whose every incentive teaches people to wait, confirm, and cover. Those rooms loved this essay. Which should have told me something sooner than it did: the pamphlet's biggest fans were the perfect refutation of its premise.
Because here is what I learned when I went past Hubbard to the record, and it changes the moral of the story.
There was no letter. The message was verbal — deliberately, so that if Rowan were taken, nothing could be found on him. The oilskin pouch strapped over the heart is Hubbard's invention, and it is not the only one.
And Rowan did not vanish alone into a jungle and conquer it by force of character. He went to Jamaica, where the American consul connected him with the Cuban Revolutionary Junta. Cuban hands rowed him by night to the coast. Cuban insurgents guided him inland through their own country to their own general, and when the mission was done, García assigned five of his men to get Rowan back out — hacking through jungle, then crossing open water in a small boat under sails stitched from gunnysacks. The man who carried the message to García was carried, most of the way, by people Hubbard's essay never mentions.
Which means the famous fact — he asked no questions — is precisely wrong as usually understood. Rowan asked questions constantly, of the consul, of the Junta, of the guides, at every step. What he never did was ask them upward. He did not hand his ignorance back to the man who gave him the mission and wait for it to be returned as instructions. He took his ignorance outward, to the people who actually held the knowledge, and traded on trust to get it. That is what initiative actually is. Not the absence of questions — the correct routing of them.
Hubbard airbrushed out the network to make a parable of solitary obedience, and in doing so he built a worse lesson than the truth. The truth is that the message got through because a chain of people — a consul, a junta, boatmen, guides, a general, an escort — each did their part without anyone upstream gripping the route. Rowan's genius was knowing that García's location was not in Washington. It was in Cuba, held by Cubans, and he went where the knowledge lived.
And there is one more person Hubbard's sermon skips, and he is the one I keep thinking about now.
Somebody handed Rowan the mission and let go. Colonel Arthur Wagner, who ran military intelligence, picked a forty-year-old lieutenant, gave him an errand with no map attached — and then did not row after the boat. No check-ins from the beach. No demand for the route in advance. The entire episode depends on an act that the essay never once praises, because the essay was not written for the people who perform it: the act of handing someone a message and trusting them with the finding out.
That is the other half of the message, and it is the half every micromanaged workplace is missing. The rooms I described are not short on people who could carry a letter. They are short on anyone willing to hand one over. You cannot carry a message no one will give you — and a message accompanied by hourly supervision is not a message, it is a script with a witness. I wrote a couple of weeks ago about the rank that gets assigned early and never re-run; the meeting where you lack the status to speak is the same disease from another angle. In both cases the institution has decided, in advance and permanently, who is allowed to know things — and then it wonders, in Hubbard's borrowed voice, why nobody shows initiative.
The cruelest part is what the people inside eventually do with the sermon. They turn it on themselves. Years of ungiven letters, and the micromanaged conclude that they must not be Rowan — when the actual finding, on the actual evidence, is that they were never once handed the pouch and pointed at Cuba. I spent real time making that error about myself, holding Hubbard's indictment for counts that belonged on someone else's charge sheet. Part of the audit of a working life — and I have been doing this audit all month — is separating the two honestly: the letters I dropped, which were mine, and the letters that were never handed over, which were not.
So here is where I land, holding both halves.
Initiative is not a virtue one person can perform alone. It is a covenant, and it takes two signatures — the carrier's and the sender's. Hubbard's essay demands the first signature and never mentions the second, which is exactly why the institutions that most needed to hear about the second bought it by the half million to distribute the first as homework.
The indictment I accepted at the top still stands; I signed some letters late and some not at all, and no theory of bad bosses redeems those. But I have also stopped reading my whole ledger in Hubbard's voice. And the question the essay leaves me with now is not the one it left me with at first reading. Then, it was: would I carry the message? Now — with people looking to me the way I once looked up — it is the harder one, the one Rowan's forgotten colonel answered in an afternoon:
Can I hand someone the message, tell them only that García is somewhere in the mountains, and stay off the water while they find him?
Because the message got through — the real one, the one with no pouch and no lone hero — for one reason. Every hand in the chain did its own half, and nobody grabbed the oars of a boat they had already launched.