Hemingway (left) and Samuelson fishing and talking in Key West.

“As a writer you should not judge. You should understand,” Ernest Hemingway (July 21, 1899–July 2, 1961) counseled in his 1935 Esquire compendium of writing advice, addressed to an archetypal young correspondent but based on a real-life encounter that had taken place a year earlier.

In 1934, a 22-year-old aspiring writer named Arnold Samuelson set out to meet his literary hero, hoping to steal a few moments with Hemingway to talk about writing. The son of Norwegian immigrant wheat farmers, he had just completed his coursework in journalism at the University of Minnesota, but had refused to pay the $5 diploma fee. Convinced that his literary education would be best served by apprenticing himself to Hemingway, however briefly, he hitchhiked atop a coal car from Minnesota to Key West. “It seemed a damn fool thing to do,” Samuelson later recalled, “but a twenty-two-year-old tramp during the Great Depression didn’t have to have much reason for what he did.” Unreasonable though the quest may have been, he ended up staying with Hemingway for almost an entire year, over the course of which he became the literary titan’s only true protégé.

Samuelson recorded the experience and its multitude of learnings in a manuscript that was only discovered by his daughter after his death in 1981. It was eventually published as With Hemingway: A Year in Key West and Cuba (public library) — the closest thing to a psychological profile of the great writer.

Shortly after the young man’s arrival in Key West, Hemingway got right down to granting him what he had traveled there seeking. In one of their first exchanges, he hands Samuelson a handwritten list and instructs him:

Here’s a list of books any writer should have read as a part of his education… If you haven’t read these, you just aren’t educated. They represent different types of writing. Some may bore you, others might inspire you and others are so beautifully written they’ll make you feel it’s hopeless for you to try to write.

This is the list of heartening and hopeless-making masterworks that Hemingway handed to young Samuelson:

Not on the handwritten list but offered in the conversation surrounding the exchange is what Hemingway considered “the best book an American ever wrote,” the one that “marks the beginning of American literature” — Mark Twain’s Adventures of Huckleberry Finn (public library).

Art by Norman Rockwell for a rare edition of Mark Twain’s Adventures of Huckleberry Finn.

Alongside these edifying essentials, Hemingway offered young Samuelson some concrete writing advice. Advocating for staying with what psychologists now call flow, he begins with the psychological discipline of the writing process:

The most important thing I’ve learned about writing is never write too much at a time… Never pump yourself dry. Leave a little for the next day. The main thing is to know when to stop. Don’t wait till you’ve written yourself out. When you’re still going good and you come to an interesting place and you know what’s going to happen next, that’s the time to stop. Then leave it alone and don’t think about it; let your subconscious mind do the work.

Then, echoing Lewis Carroll’s advice on overcoming creative block in problem-solving, Hemingway considers the practical tactics of this psychological strategy:

The next morning, when you’ve had a good sleep and you’re feeling fresh, rewrite what you wrote the day before. When you come to the interesting place and you know what is going to happen next, go on from there and stop at another high point of interest. That way, when you get through, your stuff is full of interesting places and when you write a novel you never get stuck and you make it interesting as you go along. Every day go back to the beginning and rewrite the whole thing and when it gets too long, read at least two or three chapters before you start to write and at least once a week go back to the start. That way you make it one piece. And when you go over it, cut out everything you can. The main thing is to know what to leave out. The way you tell whether you’re going good is by what you can throw away. If you can throw away stuff that would make a high point of interest in somebody else’s story, you know you’re going good.

He then returns to the psychological payoff of this trying practice:

Don’t get discouraged because there’s a lot of mechanical work to writing. There is, and you can’t get out of it. I rewrote A Farewell to Arms at least fifty times. You’ve got to work it over. The first draft of anything is shit. When you first start to write you get all the kick and the reader gets none, but after you learn to work it’s your object to convey everything to the reader so that he remembers it not as a story he had read but something that happened to himself. That’s the true test of writing. When you can do that, the reader gets the kick and you don’t get any. You just get hard work and the better you write the harder it is because every story has to be better than the last one. It’s the hardest work there is. I like to do and can do many things better than I can write, but when I don’t write I feel like shit. I’ve got the talent and I feel that I’m wasting it.

When Samuelson asks how one can know whether one has any talent, Hemingway replies:

You can’t. Sometimes you can go on writing for years before it shows. If a man’s got it in him, it will come out sometime. The only thing I can advise you is to keep on writing but it’s a damned tough racket. The only reason I make any money at it is I’m a sort of literary pirate. Out of every ten stories I write, only one is any good and I throw the other nine away.

Hemingway tempers this with a word of advice on ambition, self-comparison, and originality:

Never compete with living writers. You don’t know whether they’re good or not. Compete with the dead ones you know are good. Then when you can pass them up you know you’re going good. You should have read all the good stuff so that you know what has been done, because if you have a story like one somebody else has written, yours isn’t any good unless you can write a better one. In any art you’re allowed to steal anything if you can make it better, but the tendency should always be upward instead of down. And don’t ever imitate anybody. All style is, is the awkwardness of a writer in stating a fact. If you have a way of your own, you are fortunate, but if you try to write like somebody else, you’ll have the awkwardness of the other writer as well as your own.

In a sentiment that calls to mind Neil Gaiman’s magnificent commencement address on the only adequate response to criticism, Hemingway cautions Samuelson about the petty jealousies that arise with success:

When you start to write everybody is wishing you luck, but when you’re going good, they try to kill you. The only way you can ever stay on top is by writing good stuff.

With Hemingway: A Year in Key West and Cuba brims with the celebrated writer’s wisdom on literature, life, and the creative experience. Complement it with Hemingway on knowledge and the dangers of ego, and his short, spectacular Nobel Prize acceptance speech, then revisit the essential reading lists of Joan Didion, Leo Tolstoy, Susan Sontag, Alan Turing, Brian Eno, David Byrne, Neil deGrasse Tyson, and Patti Smith.