Hemingway's advice on writing, ambition, and his Essential Reading List for Aspiring Writers – The Marginalian

“As a writer you should not judge. You should understand,” Ernest Hemingway (July 21, 1899–July 2, 1961) advised in his 1935 book Esquire a collection of writing advice, aimed at the archetypal young writer but based on a real-life encounter that happened last year.

In 1934, 22-year-old aspiring writer Arnold Samuelson met 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 graduated from the University of Minnesota with a degree in journalism, but refused to pay the $5 diploma fee. Convinced that his literary education would be best obtained by self-study from Hemingway, however short-lived, he rode a coal car from Minnesota to Key West. “It seemed a very foolish thing to do,” Samuelson later recalled, “but twenty-two years of recklessness during the Great Depression didn't have to be much of a reason for what he did.” Although the idea was far-fetched, it ended up staying with Hemingway for almost a year, during what became the literary titan's true end.

Samuelson recorded the experience and many of the things he learned in a manuscript that his daughter received after his death in 1981. He was eventually published as With Hemingway: A Year in Key West and Cuba (public library) – something very close to the psychological profile of a great writer.

Shortly after the young man arrived in Key West, Hemingway came down and gave him what he was looking for. In one of their first conversations, he gives Samuelson a handwritten list and instructs him:

Here is a list of books any writer should have read as part of their education… If you haven't read these, you haven't. They represent different types of writing. Some may bore you, some may inspire you and some are so well written they will make you feel hopeless about trying to write.

Here is a list of the interesting and hopeless works of art that Hemingway gave to the young Samuelson:

1. Hotel Blue (public library) with Stephen Crane
2. Open Boat (public library) with Stephen Crane
3. Madame Bovary (free ebook | public library) with Gustave Flaubert
4. They are from Dublin (public library) with James Joyce
5. Red and Black (public library) with Stendhal
6. About Human Slavery (free ebook | public library) with W. Somerset Maugham
7. Anna Karenina (free ebook | public library) with Leo Tolstoy
8. War and Peace (free ebook | public library) with Leo Tolstoy
9. Buddenbrooks (public library) with Thomas Mann
10. Hello and goodbye (public library) with George Moore
11. Brothers Karamazov (public library) with Fyodor Dostoyevsky
12. The Oxford Book of English Verse (public library)
13. The Great Room (public library) with EE Cummings
14. Accommodations in Wuthering Heights (free ebook | public library) with Emily Brontë
15. Long ago (free ebook | public library) with WH Hudson
16. An American (free ebook | public library) with Henry James

Not in a handwritten list but given in the conversation surrounding the exchange is what Hemingway considered “the best book ever written by an American,” the one that “marks the beginning of American literature” – Mark Twain's Adventures of Huckleberry Finn (public library).

Along with these important constructive things, Hemingway gave the young Samuelson practical advice about writing. Representing sitting 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 to never write too much at a time… Never pump yourself dry. Leave a little for the next day. The key is knowing when to stop. Don't wait until you write for yourself. If you're going well and you get to an interesting place and you know what's going to happen next, it's time to stop. Then let it go and don't think about it; let your subconscious mind do the work.

Then, echoing Lewis Carroll's advice to overcome creative block in problem solving, Hemingway examines the practical tactics of this psychological strategy:

The next morning, when you've slept soundly and feel fresh, rewrite what you wrote the day before. When you get to an interesting place and you know what will happen next, move on from there and stop at another place of high interest. That way, when you're passing by, your stuff is full of interesting places and when you're writing a novel you don't get stuck and you make it funnier as you go along. Every day go back to the beginning and rewrite everything and when it gets too long, read at least two or three chapters before you start writing and at least once a week go back to the beginning. That way you make it one piece. And when you're done, decide what you can do. The key is knowing what to leave behind. The way you see that you are going well is what can throw you off. If you can throw away things that would make a high point of interest in someone else's story, you know you're on the right track.

He then returns to the psychological benefits of this practice:

Don't be discouraged because there is a lot of mechanical writing. There is, and you can't get out of it. I rewrote A Farewell to Arms at least fifty times. You have to fix it. The first draft of anything is shit. When you start writing you get all the kicks and the reader gets nothing, but after learning to work your goal is to transfer everything to the reader so that he remembers not as a story he had read but something that happened to him. That is the true test of writing. If you can do that, the student gets a kick and you get nothing. You just get a tough job and the better you write the harder it is because every story has to be better than the last one. It's the hardest job there is. I love to act and I can do many things better than I can write, but if I don't write I feel empty. I have talent and I feel like I'm wasting it.

When Samuelson asks how one knows if one has talent, Hemingway replies:

You can't. Sometimes you can go on writing for years before it shows up. If someone has it in him, it will come out at some point. The only thing I can advise you to do is to keep writing but it's brutal. The only reason I make money from it is that I'm kind of a learning pirate. Out of every ten stories I write, only one is good and the other nine I discard.

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

Never compete with living writers. You don't know if they are good or not. Compete with the dead you know are good. Then when you pass them you know you're on the right track. You had to read all the good stuff to know what to do, because if you have a story like someone else wrote, yours is no good unless you can write a better one. In any art you are allowed to steal anything if you can make it better, but the tendency should always be high rather than low. And don't copy anyone. All style is the writer's discomfort in telling the truth. If you have your own way, you're lucky, but if you try to write like someone else, you'll have the other writer's difficulties as well as your own.

With a sentiment reminiscent of Neil Gaiman's first speech that the only adequate response to criticism, Hemingway warns Samuelson of the petty jealousy that emerges from success:

When you start writing everyone wishes you luck, but when you get going, they try to kill you. The only way you can stay on top is by writing good stuff.

With Hemingway: A Year in Key West and Cuba filled with the famous author's wisdom on books, life, and creative experiences. Fill it with Hemingway's knowledge and the perils of self-centeredness, and his short, dramatic acceptance speech for the Nobel Prize, and revisit the essential reading lists of Joan Didion, Leo Tolstoy, Susan Sontag, Alan Turing, Brian Eno, David Byrne, Neil deGrasse Tyson, and Patti Smith.