Ernest Hemingway explains his craft, and why he had to be a 'literary pirate' to make money as an author

The Nobel laureate explains what a writer must do and how one must approach work to create something worthwhile.

Writing is difficult. Writing well is nearly impossible. 

I say that as a journalist and author who writes everyday. The recurring theme from history’s best writers is that it requires massive volume to arrive at something worth publishing, but even then, there's no such thing as guarantees.

The inimitable Ernest Hemingway said as much when explaining how he rewrote parts of his legendary novel, A Farewell to Arms, at least fifty times. 

“The first draft of anything is shit,” he said, according to Arnold Samuelson’s memoir, With Hemingway: A Year in Key West in Cuba. 

Samuelson, 22, spent a year with Hemingway in Key West with the intention of learning how to write. “It seemed a damn fool thing to do, but a twenty-two-year-old tramp during the Great Depression didn’t have to have much reason for what he did,” Samuelson said later in recollection.

The young man effectively became Hemingway’s sole known protégé. When he asked Hemingway how a writer can know whether they have any talent, he recorded a downbeat yet candid response from his mentor. 

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.

Filled with wise anecdotes, With Hemingway is a glimpse into a great author's psychology, as Samuelson dutifully recorded various events and conversations from their time together.

Hemingway told him that writing demands a rigorous discipline, without which success remains elusive. But, notably, part of that discipline is knowing when enough's enough for a writing session.

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, once you return to the work, Hemingway advised to rewrite the material you had written the day before.

Write from that point until you arrive at another key point of interest in the draft, then stop once again when you have an idea of what events come next. Additionally, as his famously terse prose reveals, Hemingway was a devoted advocate of paring down work as much as possible.

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.

The craft at first, Hemingway said, should not be based in vanity. The process of writing gives the writer a "kick" even though the first draft will be garbage, he explained.

Only when you stick with the same material, and hack away at it over and over, will it eventually turn into something that not only enthuses the writer, but the reader.

The most critical component to good, powerful writing is that the reader remembers the story as if it had happened to themself, according to Hemingway.

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.

On competition and originality

Hemingway was competitive, not just in his work but in his life as an avid hunter and sportsman. He told Samuelson, however, that a writer would be best suited to compete with history's best writers long gone, rather than contemporaries.

The ones who are still alive, he seemed to suggest, don't yet have their legacy established so it's not worth a writer's time to study them.

Compete with the dead [writers] 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.

Complement this with readings on focus for creatives, making creativity a choice rather than an accident, and the story of how I wrote a bestseller in a year while working as a full-time journalist.