Thoughts on Legal Writing from the Greatest of Them All: Ernest Hemingway

By Gerald Lebovits

March 23, 2021

Thoughts on Legal Writing from the Greatest of Them All: Ernest Hemingway


By Gerald Lebovits

Ernest Miller Hemingway is one of the greatest writers the world has known.

Born in 1899 in Oak Park, Illinois, Hemingway began his career at the age of 17 as a journalist for the Kansas City Star. After World War I began, he joined a volunteer American Red Cross ambulance unit in Italy, where he made many observations on which he’d rely for his future novels. After he was injured in the Second Battle of the Piave River,[1] he returned to the United States to continue his work as a journalist for Canada’s Toronto Star. He covered international political events, such as the Greek Revolution. During this time, Hemingway realized that the truth of a story is often hidden beneath its surface.[2]

As a journalist, he concentrated primarily on the immediate events to create a “spotlight” focus around them.[3] That focus required succinctness and concision due to space constraints in printed newspapers. After becoming comfortable with this style, Hemingway applied it to his works of fiction with great success. He found that the fewer the details, the more powerful the stories.[4] The novels he wrote using this style have become classics of American literature.

His first successful work, The Sun Also Rises, described his experiences as part of a group of American expatriates in Paris. His second book, A Farewell to Arms, depicted an American ambulance worker’s disappointment in World War I and his role as a deserter. He used his experiences as a reporter in Spain as the background for his novel For Whom the Bell Tolls. One of his later works, The Old Man and the Sea, told the story of a lonely fisherman’s journey.[5]

Hemingway’s protagonists often included tough, courageous characters who go against the grain and disagree with modern society. This      archetype became known as “Hemingway Code Hero,” defined as “a man who lives correctly, following the ideals of honor, courage and endurance in a world that is sometimes chaotic, often stressful, and always painful.”[6] Some believe that these protagonists were an extension of Hemingway himself, who may have used his novels to tell stories about a fictionalized version of himself.

As a young writer, he discovered what would become his signature writing technique, the iceberg theory, which had a profound impact on 20th-century fiction writing.[7] Also known as the theory of omission, the iceberg theory is a minimalistic style of writing in which the writer focuses on the surface elements of the story – the tip of the iceberg – without going into detail about the underlying themes, the rest of the iceberg submerged in the ocean. Hemingway believed that readers should glean the meaning of a story implicitly, rather than explicitly stated by the writer. Musing about his own theory, Hemingway wrote that “[i]f a writer of prose knows enough about what he is writing about, he may omit things he knows, and the reader, if the writer is writing truly enough, will have a feeling of those things as strongly as if the writer had stated them.”[8] His approach to writing has been adopted by many legal writers, including Justice Anthony Kennedy, who has taken after Hemingway by excluding adverbs from his legal writing.[9]

Throughout his writing career, spanning from the 1920s to the 1950s, Hemingway published seven novels, six collections of short stories and two nonfiction books. For his work, Hemingway won the Pulitzer Prize for Fiction in 1953 and the Nobel Prize in Literature in 1954. For his service as a World War I correspondent, he received a Bronze Star in June 1947 at the U.S. embassy in Cuba.[10] He committed suicide in 1961 at age 61.

Hemingway’s works feature themes of love, war, travel, wilderness and loss, recurring themes in American literature.[11] During his career, he gave advice to aspiring writers on how to improve their craft. Much of his advice was about fiction writing, but it also applies to legal writing.

Begin With One True Sentence

In his memoir A Moveable Feast, Hemingway discussed his writing process and how he would start writing something new. When he got stuck at the beginning of a piece, he made sure not to worry, assuring himself instead that he had written before and would write again. All he had to do was write one true sentence, the truest sentence he knew. He found this easy because there always was at least one true thing he knew or had heard someone else say. This trick helped him stay true to his declarative, lean and simple writing style.[12]

Legal writing is composed of many true sentences. It’s difficult in any writing, legal or otherwise, to know where or how to start. Hemingway asserted that beginning with one true sentence allows a writer to “cut the scrollwork or ornament out and throw it away,” shifting the focus of the writing to the truth of the matter at hand.[13]

Start and Finish Writing in “Flow”

According to psychologist Mihály Csíkszentmihályi, flow is an optimal state of consciousness in which we feel and perform our best.[14] Csíkszentmihályi describes the mental state of flow as “being completely involved in an activity for its own sake. The ego falls away. Time flies. Every action, movement, and thought follows inevitably from the previous one, like playing jazz. Your whole being is involved, and you’re using your skills to the utmost.”[15]

While he never mentioned “flow” by name, Hemingway alluded to the concept in what he considered the most important thing he’d learned about writing: not to write too much at a time. He advised writers that the time to stop for the day is when things are going well and you know what’s coming next.[16] The stopping point, he described, occurs amid flow. He advised writers to stop at this point every day to prevent getting stuck or experiencing writer’s block.[17] Hemingway wrote that he had “learned already never to empty the well of [his] writing, but always to stop when there was still something there in the deep part of the well.”[18]

Knowing when to stop is a valuable skill that can help prevent burnout as well as writer’s block. Working in flow promotes deep concentration, motivation, and overall satisfaction and gratification. [19]

Think About Writing Only When Writing

Having boundaries is a crucial part of life. But respecting boundaries is difficult. Writers often spend lots of time thinking about their works when they aren’t writing. Hemingway warned against this, urging writers not to think about their work in between writing sessions.[20] He believed that doing so would allow the subconscious to continue to work on the piece all the time. On the other hand, he believed that if writers consciously think or worry about the piece, they’ll kill it, and their brain will be tired before even beginning to write.[21]

He expanded on this idea in A Moveable Feast, in which he wrote about the need to read a different book after he had finished writing for the day. He found that without reading to distract himself he’d lose the thing he was writing before he could continue the next day. He also spoke highly of using exercise, not only as a distraction, but to wear out the body and create fatigue. In referring to the “well of his writing,” Hemingway preferred to let it be refilled at night from the springs that fed it: his subconscious.[22]

This tip will help prevent burnout in lawyers, while also contributing to a healthy work-life balance.

Reread and Rewrite What You’ve Written

To ensure that a piece of writing is cohesive, Hemingway recommended rereading your work from the beginning every day before attempting to continue.[23] He noted the importance of editing while reading, instructing writers to cut out everything they can. According to Hemingway, the best way to gauge the quality of your writing is by what you can throw away. If what you’re able to remove is still important and compelling in its own right, then your writing is good.[24]

Hemingway was a proponent of rewriting the work from the beginning each day, until the work became too long to continue doing so.[25] This helped him bring his ideas together and gave him another opportunity to edit as he wrote. He described the first draft of anything as terrible, explaining that he rewrote A Farewell to Arms over 50 times before he felt it was complete.[26]

Hemingway advised writers not to get too discouraged during this process, which he described as mechanical work that can’t be avoided. He acknowledged the difficulty of the writing process and even believed it’s the hardest work there is. He believed that writing takes courage and that the hardest part about it is finishing what you’ve started.[27]

Persevere and Stay Positive

Hemingway encouraged writers not to succumb to their own negative thoughts about their writing. He compared writing to war and writers to soldiers. It’s the writers’ responsibility to see their work through. Once writers have begun writing, Hemingway believed, it’s not only counterproductive but also cowardly to worry whether they can finish. He argued that the writer has no choice but to go on, making worrying a senseless act and a waste of time.

Hemingway did recognize, however, that people don’t always have control over their thoughts, positive or negative. He advised writers to catch themselves if they think negatively and actively change or reframe that thought. In doing so, writers will learn how to write and find their own process.[28]

Be Brief

The simplest piece of advice Hemingway gave to writers may also be the most difficult one to implement. Hemingway, known for his succinct, direct, unadorned prose, encouraged other writers to emulate his style. In his story fragment On Writing, Hemingway described disliking writers who, in his words, “never learned how to say no to a typewriter”[29] Hemingway often opted for one-syllable words and short sentences, leaving out adverbs, adjectives, and conclusions, and using positive language to make a point.[30] Other writers at the time used flowery, descriptive language and complicated syntax. Hemingway did the opposite, and he was rewarded for it. He wrote to his editor in 1945 that “[i]t wasn’t by accident that the Gettysburg address was so short. The laws of prose writing are as immutable as those of flight, of mathematics, of physics.”[31] His goal in writing was to write what he saw and felt in the best and simplest way.[32] Hemingway allowed his readers to think for themselves instead of telling them in complex and fancy language what to make of his writing, saying that “the first and most important thing of all, at least for writers today, is to strip language clean, to lay it bare down to the bone.”[33]

Gerald Lebovits ([email protected]), an acting Supreme Court justice in Manhattan, is an adjunct at Columbia, Fordham, and NYU law schools. For her research, he thanks Nia Goodman (Columbia Law School), his judicial fellow. The next issue of the Journal will contain Judge Lebovits’s final Legal Writer column. With that, he will have published his column in every edition of the Journal for the last 20 years.

[1]. The Legal Writer’s paternal grandfather also fought in that battle, but for the Austro-Hungarian army.

[2]. Michael Reynolds, The Young Hemingway 17 (1998).

[3]. Jeffrey Meyers, Hemingway: A Biography 98-99 (1985).

[4]. Id.

[5]. Horst Frenz, Ernest Hemingway Biography (1969),

[6]. Philip Young, Ernest Hemingway 36-37 (1952).

[7]. Reynolds, supra note 2, at 17.

[8]. Ernest Hemingway, Death in the Afternoon 19 (1932).

[9]. Ed Whelan, Justice Kennedy and Ernest Hemingway National Review, Oct. 9, 2014,

[10]. Frenz, supra note 5.

[11]. Frederic Svoboda, The Great Themes in Hemingway 155 (2000).

[12]. Ernest Hemingway, A Moveable Feast 12 (1964) (hereinafter Feast).

[13]. Id.

[14]. Alayna Kennedy, Flow State: What It Is and How to Achieve It. HuffPost, Apr. 5, 2017,

[15]. Id.

[16]. Ernest Hemingway, Monologue to the Maestro: A High Seas Letter, Esquire, Oct. 1, 1935, at 21, Esquire. (hereinafter Monologue).

[17]. Id.

[18]. Hemingway, Feast, supra note 12, at 26.

[19]. Bryan Collins, 3 Surprising Benefits of Flow State, Forbes, Mar. 31, 2020,

[20]. Hemingway, Monologue, supra note 16.

[21]. Id.

[22]. Hemingway, Feast, supra note 12, at 26.

[23]. Hemingway, Monologue, supra note 16.

[24]. Id.

[25]. Id.

[26]. Id.

[27]. Arnold Samuelson, With Hemingway 180 (1981).

[28]. Id.

[29]. Ernest Hemingway, On Writing 89 (1984) (hereinafter On Writing).

[30]. Joan Didion, Last Words, New Yorker, Oct. 26, 1998,

[31]. Hemingway, On Writing, supra note 29, at 87.

[32]. Id.

[33]. U.S. Air Force, Air Force Writing 9 (1966).

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