How to Write Like Chekhov

Advice and Inspiration, Straight from His Own Letters and Work


By Anton Chekhov

Edited by Piero Brunello

Edited by Lena Lencek

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Maxim Gorky said that no one understood — the tragedy of life’s trivialities — as clearly as Anton Chekhov, widely considered the father of the modern short story and the modern play. Chekhov’s singular ability to speak volumes with a single, impeccably chosen word, mesh comedy and pathos, and capture life’s basic sadness as he entertains us, are why so many aspire to emulate him. How to Write Like Chekhov meticulously cherry-picks from Chekhov’s plays, stories, and letters to his publisher, brother, and friends, offering suggestions and observations on subjects including plot and characters (and their names), descriptions and dialogue, and what to emphasize and avoid. This is a uniquely clear roadmap to Chekhov’s intelligence and artistic expertise and an essential addition to the writing-guide shelf.


ANTON CHEKHOV was born in 1860 in Taganrog, a port on the Sea of Azov. His father, a shopkeeper, was the son of a peasant who bought himself and his family out of serfdom. Chekhov began to write short stories while studying at the University of Moscow, and after graduating from medical school he embraced both professions: medicine as his “lawful wife” and literature as his “mistress.” While continuing to write short stories, Chekhov became interested in the theater and, early in his career, began to write plays. His first successful full-length play, The Sea Gull, was produced in 1896, followed by Uncle Vanya and The Three Sisters. The Cherry Orchard appeared in 1904, and in the same year Chekhov, who had long suffered from tuberculosis, died at the age of forty-four.
Co-editor PIERO BRUNELLO is a professor of social history at the University of Venice in Italy.
Co-editor and translator LENA LENČEK is professor of Russian and the humanities at Reed College in Portland, Oregon, and the author, editor, co-author, and co-editor of more than a dozen books, including Beach: Stories by the Sand and Sea. She has recently annotated a new edition of Tolstoy’s War and Peace. She lives in Portland, Oregon.

To my father, Rado L. Lenček and my sister Bibi
—L. L.

“In writing, it is not the head but the seat that gets the job done.”
RADO L. LENČEK (1921-2005)

THIS BOOK BEGAN LIFE AS TWO SEPARATE ITALIAN VOLUMES, No Plot, No Ending and Good Shoes and a Note-book .1 This English-language edition combines this material between one set of covers, which makes sense for two reasons: it gives the reader direct access to Anton Chekhov’s nuggets of writing wisdom in the form of advice to writers tucked in his correspondence, and it provides examples of this advice in practice, in the form of excerpts from his nonfiction travel memoir The Island of Sakhalin.2
The notes that periodically amplify the primary text are by Piero Brunello [P.B.] and myself [L.L.], and in part 2, “Good Shoes and a Notebook,” a dozen or so are by Chekhov himself [A.C.]; those notes attributed to him here originally appeared as notes to The Island of Sakhalin.

THIS VOLUME PRESENTS ANTON CHEKHOV’S ADVICE ON how to write. Its purpose is to transmit Chekhov’s guidelines on becoming a good writer, and it is presented with the hope that these guidelines will be useful, in various ways, to novices and to experienced professional writers alike. Chekhov’s detailed suggestions draw heavily on his own experience, both as a writer of short stories, plays, novellas, and nonfiction and as a discerning reader of literary texts. He knew the burden of solitude that comes with writing, the compulsive need to write, and the dispiriting sting of an indifferent reception.
How to Write Like Chekhov began as a collection of advice that over a period of time I excerpted from Chekhov’s work to help with my own writing. One day it occurred to me that what this great writer had to say on the subject could be useful to others as well. I remembered, for instance, that Raymond Carver—who in addition to writing short stories and poems taught creative writing for many years—used to credit Chekhov with having had an “enormous influence” on his own work and that he too had echoed Chekhov’s lessons: to stick to “plain but precise language”; to reject “words weighed down with uncontrolled emotion”; to deliver “serious testimony about our lives”; and to remember that critics “can alleviate the sense of solitude” experienced by those who write.3 Thus was born the idea for a book, and one organized around several topics.
Part 1, “No Plot, No Ending,” is almost exclusively composed of material taken from Chekhov’s extensive correspondence between the years 1886 and 1902, much of it with editors, writers, family, and friends bitten by the writing bug. Famous for being generous with his time and his energy, Chekhov was besieged with manuscripts and requests for feedback. Excerpts from his replies are included here and organized into rubrics cued by the sorts of questions that plague all writers: general questions about the motives for writing, audience, topics, approach, timing, and scope; and specific topics such as truth, descriptions, characters, emotions, what to avoid, and how to deal with one’s fellow writers.
After the theory of part 1, part 2, “Good Shoes and a Notebook,” takes a different approach: concrete demonstrations taken largely from Chekhov’s nonfiction travel memoir The Island of Sakhalin. Initially conceived as his doctoral dissertation in medicine, though never put to that use, this extraordinary exposé by Chekhov of the czarist penal system was undertaken in the scientific spirit of Claude Bernard, the nineteenth-century physiologist who championed philosophical skepticism as the fundamental tool of the medical researcher. “Experimenters must doubt,” Barnard wrote in his groundbreaking An Introduction to the Study of Experimental Medicine, “avoid fixed ideas, and always keep their freedom of mind.”4 Writers must do the same.
In The Island of Sakhalin, Chekhov makes few explicit statements on methodology; rather, he limits himself to the rare aside questioning the validity, for instance, of statistics, or official reports. By and large, he trusts what he is told. He interpolates into his travel notes, character sketches, and descriptions of the landscape concrete information, including demographic data, meteorological tables, and medical and crime statistics. Chekhov also says next to nothing about writing. Although, as his narrative unfolds, one senses Chekhov’s finely tuned mind sifting, weighing, and measuring hearsay against firsthand knowledge, he keeps silent about matters touching on his art. This silence presented a challenge to me, as I specifically wished to mine explicit lessons from the text. In order to do this, I have sought, first, to understand what Chekhov was doing in the course of his journey, and second, to present the episodes and anecdotes he recounts as advice, both theoretical and practical.
I have decided to arrange this advice in a way that illustrates every stage involved in creating a nonfiction manuscript. I begin with the conception of the idea and the initial tasks of reading up on the topic, framing the questions, and entertaining doubts. Next, I pass on to the fieldwork, with its research strategies and maneuvers for collecting data. Finally, I turn to the production of the manuscript itself: the organization of the notes and documents, the actual process of writing, and the delivery of the completed text into the world. I have divided this process into three sections: “The Project,” “The Report,” and “The Actual Writing.” Under each rubric, I identify a number of critical steps with a title and supply a brief explanation of the principle or “lesson” that is exemplified in the passage from Chekhov’s text. The idea here is to give readers a concrete example of how the advice was implemented, on the assumption that having a model before one’s eyes is the best route to mastering techniques.
The Sakhalin material is especially addressed to writers who, like Chekhov, are interested in discovering, exploring, and understanding the unknown. The modus operandi of his voyage of discovery is useful not only to writers who make long journeys and wish to write about them but also to those who want to understand life closer to home. Chekhov’s prose is a model for writers who care less for plot than for “what transpires in the space of a breath, in the meeting of two glances, in the moment of suspense when everything is both obvious and arcane.” Those are the words of the Italian journalist Francesca Sanvitale, speaking with reference to the work of Katherine Mansfield, a writer who shared Chekhov’s view of “the external certainty of the world, the ferment in the continual flux of life,” and believed that “the beauty of life is to be found in its kaleidoscopic appearance.”5 Mansfield, like many modern writers, admired Chekhov’s peculiarly detached curiosity: “The artist watches life closely,” she wrote in a letter in 1921. “He says softly, ‘So this is life, huh?’ And he sits down to try to express it.”6
For Chekhov, there could be no contradiction between action and observation because for him observation—objective, scrupulous, open-minded, and profoundly respectful—was itself the most hopeful and productive form of action. Contemporary writers—for instance, the Italian Natalia Ginzburg (1916-91), recognize this fine balance between the “engagement” of the socially committed intellectual and the “disengagement” of the observer as “absolutely necessary, indispensable for a novelist.” 7
I have heard it said that dancers learn, not by watching the teacher or the star pupil, but by imitating those who are just a bit better than they are. The same holds for writing. I do not know how this works; I only know that one learns from Chekhov. Maybe, as Vladimir Nabokov suggested, this is due to his “phenomenal sociability”—“his constant readiness to hobnob with anyone at all, to sing with singers and to get drunk with drunkards.”8 This gregarious spirit emerges even in the collage of fragments taken from the research and writing program that Chekhov used in investigating a penal colony located on a remote island in the Sea of Okhotsk. And it is in this spirit of convivial collegiality that we offer this book. We hope that it will prove to be a useful guide and that it might even relieve the solitude of those who wish to write, who love to travel responsibly, and who keep close to their hearts the ideal of a kind of writing that is precise, honest, and engaged.

“A man needs only seven feet of earth.” “No, it’s a corpse that needs seven feet, not a man. A man needs the whole world.”
AMONG NINETEENTH-CENTURY RUSSIAN AUTHORS, ANTON Chekhov holds the record for worst publicists. Writers, critics, and friends who in life professed boundless admiration for his work damned him with the kind of praise that kills reputations. Here are some examples: “Tchekhov was the poet of hopelessness. Stubbornly, sadly, monotonously, during all the years of his literary activity, nearly a quarter of a century long, Tchekhov was doing one thing alone: by one means or another he was killing human hopes.”10 Or another, by his theatrical collaborator Constantin Stanislavsky: “The Chekhov mood is that cave in which are kept all the unseen and hardly palpable treasures of Chekhov’s soul.”11 Maxim Gorky, who owed Chekhov a vast debt of gratitude for tireless mentoring and encouragement, came up with the following: “The author’s mind…shows up in hard outline the monotonous roads, the crooked streets, the little squalid houses in which tiny, miserable people are stifled by boredom and laziness and fill the houses with an unintelligible, drowsy bustle.”12 Prerevolutionary and Soviet critics doggedly promoted Chekhov as a kind of aesthetic phenobarbital, labeling him as “a singer of twilight moods,” “a poet of superfluous people,” “a sick talent,” “a poet of anguish,” a voice of “world sorrow,” and—the clincher in the bunch—an “optimopessimist.”13
That after such an introduction—much of it crammed onto the back cover of a repulsive puce-and-avocado-colored paperback—I would have ventured into the gloom-shrouded isle of Chekhov still amazes me. I was eighteen and had made my way through an archipelago of Russian writers, from Pushkin through Tolstoy, and so far each stop had been a luminous revelation. I loved the way these wordsmiths and plot-meisters seized my imagination, drilled into the core of adolescent angst, and delivered answers to my deepest questions about why the world was the way it was. From Pushkin’s effervescent irony, I passed to Gogol’s sublime buffoonery to Turgenev’s elegiac polemics, Dostoevsky’s sin-your-way-to-Jesus verities, and the steely morality of Tolstoy clad in the velvet glove of flawless realism.
By the time I reached Chekhov, I was in full novel gear. I could cruise effortlessly through digression-studded, intricate plots, protracted philosophical ruminations, oddly gripping debates on obscure topics, and, of course, the rich roll call of characters identified by baroque naming protocols— given name, patronymic, surname, plus a dozen affectionate and abusive derivatives. I was not prepared for brevity, nuance, and plotlessness.
Chekhov turned out to be a giant among writers: lapidary, subtle, generous, infectious, and respectful of his readers in ways that the other Russians with better PR could not even imagine. He published 568 stories in a lifetime that spanned a total of 44 years. He corresponded with all the major and minor writers, critics, and artists of his time; mentored dozens of aspiring authors; and left a legacy that included copious advice on the art of writing—and living—well.


Chekhov’s contemporaries might have found him the incarnation of melancholy, but I rather suspect that they were at a loss for how to peg his startlingly novel voice. That elusive hovering between tragedy and comedy that marks his work is in fact the first murmuring of a characteristically modern consciousness and sensibility. By this I mean our unease with a spectrum of reductive explanations (ideologies, dogmas, organized religion), our skepticism, anxiety, appetite for every pleasure of the flesh, irony, and commitment to a single, terrifying value: freedom. Rich with the sociological, economic, and political complexities of late czarist Russia from which they draw their local color, Chekhov’s stories offer few consolations to readers seeking escape from quotidian banalities or rules of conduct. They offer no palliatives, no ultimate solutions rooted in metaphysics.
Working at a time when Russian readers expected their writers to preach in the tones of Old Testament prophets, Chekhov was a bewildering anomaly. Since Peter the Great had revolutionized Russia “from above” by imposing a west European “high culture” and a stringently autocratic rule buttressed by Orthodoxy, secret police, and censorship, Russians had come to rely on their imaginative literature to perform the role that public discourse plays in the West. To do so, however, Russian writers had to adopt rhetorical subterfuges that masked their true targets, and readers adapted by learning to decipher the double-coded allusions to forbidden topics. So, for nearly two hundred years, fictions, ingeniously couched in “Aesopian language,” spoke to every political development in the czarist establishment and the world at large. But in Chekhov’s little stories, readers looked in vain for allusions to current events and editorial commentary. His tales about ordinary people doing ordinary things in ordinary places offered a stark moral: live fully, simply, with integrity, paying attention to every instant, every sensation, and every interaction.
Chekhov sounded a prophetic retreat from the oracular mission of the writer that had been the earmark of Russian artistic prose. “All great sages are as despotic as generals,” he confided to Suvorin. “So to hell with the philosophy of the great men of this world!”14 Instead, the epistemology on which he built his aesthetics required a vow of humility and a preliminary admission of ignorance. “It is high time for writers, and especially for true artists,” insisted Chekhov, “to admit that it’s impossible to explain anything. Socrates acknowledged this long ago, as did Voltaire. Only the crowd thinks it knows and understands everything there is to know and understand. And the more stupid it is, the more open-minded it thinks itself to be. But if an artist whom the crowd trusts admits that he understands nothing of what he sees, this fact alone will make a great contribution to the realm of thought and will mark a great step forward.”15 Here, Chekhov’s thinking is truly revolutionary, for no other Russian writing before him had pared down the list of prerequisites for authoritative authorial speech to a negative trait: the refusal to claim knowledge in the face of its absence.
A self-made man who worked his way out of the provincial port of Taganrog and a childhood marked by fiscal anxiety and low status, Chekhov was brutally honest in his assessment of self and others.16 His correspondence and his fiction are testaments to his truth-telling on all subjects—except for his health, about which he was in constant denial. His medical training and his devotion to the principles of the French physician Claude Bernard fed a staunchly materialist realism—and the willingness to call a spade a spade. In a famous letter to his editor Alexei Suvorin, Chekhov articulated the theoretical principle at the basis of his work: “You are confusing two notions, the solution of a problem and the correct posing of the question. Only the second is essential for the artist.”17 If there was one thing in which Chekhov believed heart and soul it was in the transformative power of heeding this fundamental diagnostic imperative. Four years before his death, he wrote, looking back at his work, “I only wanted to tell people honestly: look, look at how badly you live, how boring are your lives. The important thing is that people should understand this; if they do understand this, they will certainly invent a different and a far better life. Man will become better only once we have shown him as he is.”18
Russia in the final decades of the nineteenth century was still a nasty, brutish, unforgiving sort of place for someone not born into the aristocracy and thus lacking automatic admission to university study and a high-priced European grand tour, followed by an advantageous marriage and a sinecure in government service. Chekhov relied on himself—in life as well as in his art. He had no use for coteries, cliques, and societies. Moving in and out of literary and social milieus, he was immune to the intellectual fads for which educated, pedigreed Russians had an almost fatal weakness. Populism, socialism, decadence, symbolism, Tolstoy’s dogma of nonresistance to evil and adulation of the peasant—all washed off Chekhov’s back like so much rain. “I have peasant blood flowing in my veins,” Chekhov wrote to Suvorin. “So I am not the one to be impressed by peasant virtues.” Nor was he swayed by Tolstoy’s fanatical asceticism about the virtue of abstinence from physical pleasures. “My sense of fair play tells me,” he wrote, “that there is more love of humanity in steam and electricity than in chastity and abstention from meat.”19
This pragmatic attachment to comfort and security—what we would call the “bourgeois values”—was only the material side of Chekhov’s ethos of existential responsibility. A stoic by conviction and necessity, Chekhov sought a moral calculus by which modern man could live a virtuous and pleasurable life. His ill health in fact provided a constant “reality check” on what was important and what superfluous. Living with the omnipresent awareness of death, the tubercular Chekhov applied the yardstick of mortality to every expenditure of passion, irritation, despair, anguish, pettiness, hard-heartedness, greed, or vanity.
This proto-existential calculation might have struck contemporaries as amoral, but it was entirely consonant with the modern sensibility charted by, among others, Dostoevsky, Nietzsche, and Freud. Theirs too was a universe from which God—the ultimate umpire of right and wrong, good and evil—had been banished. Chekhov, force-fed religion by a tyrannical father, had developed a spiritual allergy to absolutes. Yet he realized that by declaring God dead, modern man had not eliminated the problem of meaning and value; he had only moved its solution to another plane.
Chekhov’s stories—even the earliest comic sketches dashed off for money—expose conventional piety as a feeble moral guide with a selective memory, ready to excuse every kind of viciousness in the name of abstractions (Order! Security! Family!). This was, in fact, the moral climate of the closing decades of the nineteenth century, when, exhausted by the legal, social, and economic reforms of Alexander II, Russia slumped into a stultifying inertia of official Orthodoxy and nationalism. Rather than tackling the big political issues, however, Chekhov took his moral crusade into the private lives of individuals. In his view, only the individual personality, unencumbered by dogma, could right the wrongs of a class, a nation, or an age and sow the seeds of genuine historical change. “I believe in particular people, I see salvation in particular personalities, scattered here and there throughout the whole of Russia—whether they are intellectuals or peasants, there is strength in them, though they are few.”20


A physician with a deep understanding of the material causes of spiritual distress—poverty, malnutrition, poor hygiene, sexual frustration, sleep deprivation—Chekhov asked how one can live with dignity and joy without the Big Overseers of Religion, State, and Ideology looking over one’s shoulder. As he famously confided in a letter to Alexei Pleshcheyev, “My holy of holies is the human body, health, intelligence, talent, inspiration, love, and absolute freedom, freedom from violence and falsehood, no matter what form these might take. This is the program to which I would adhere were I a great artist.”21 In an age of creeping agnosticism, when death is the only absolute, Chekhov’s protagonists eat, drink, work, court, and carry on trivial conversations between the iron necessity of death and the terrifying freedom to improvise meaning for life. Sentenced to die and powerless to chart the trajectories of their lives (which are usually entirely out of their control), all are shown, in ways subtle and small, as having the freedom to choose how to respond to the challenges and obstacles of the everyday. In a letter to his brother Nikolai, Chekhov sketched out this “gospel” in characteristically concrete terms, avoiding all abstraction:
Educated people, in my opinion, should satisfy the following conditions: They respect the individual, and therefore they are extremely tolerant, gentle, polite, and compliant.... They don’t make a fuss about a hammer or a lost galosh..... They forgive noise, cold, overcooked meat, and jokes.... They don’t humiliate themselves with the aim of arousing somebody else’s sympathy. They don’t play on other people’s heartstrings so as to be sighed and fussed over in return. They don’t say: “Nobody understands me!” or: “I’ve wasted my talents!” … They are not vain. They are not interested in such false treasures as acquaintance with celebrities.… They cultivate their aesthetic sense. They are incapable of going to sleep in their clothes, of seeing bedbugs in a crack in the wall, of breathing foul air, of walking on a floor that has been spat on, of eating things cooked on a kerosene stove.22
The ethical code formulated in constant mindfulness of death includes aesthetics in a way that is familiar to us. For Chekhov, the good life is inseparable from the beautiful, and both require respect for nature. In his letters and his stories, Chekhov insists on seeing nature as the arena in which the fullness of the human personality can be given its scope. And it is in his characters’ regard or disregard for the nonhuman beings of the world—plants and animals—that Chekhov finds the ethical core of individuals. In this respect too, he was prescient of our contemporary commitment to environmental responsibility by promoting the preservation of nature as the touchstone of the moral potential of man. As A. P. Chudakov reminds us, Chekhov “was the first literary figure to include in the ethical sphere man’s attitude to nature.”23
The protagonist of his early play The Wood-Demon, a physician by the name of Khrushchov, sounds the clarion call of eco-activism when he protests his neighbor’s decision to cut down a forest: “To fell a thousand trees, to destroy them for a couple of thousand rubles, for clothes for your womenfolk, for whims and luxury…[t]o destroy them so that posterity will curse our barbarity!”24 This sentiment echoes in a number of Chekhov’s works—“Gooseberries,” Three Sisters, The Cherry Orchard—in the various iterations that eventually found their way into our environmentalist program. Chekhov’s concern for the biosphere stems from a peasant’s pragmatism but sounds like the formula for contemporary holistic thinking. For example, the protagonist of an early story notes: “The sun, the sky, the woods, the rivers, the creatures—it was all created, adapted, mutually adjusted. Everything was put in order and knows its place.”25


Chekhov’s life fit neatly within the life span of Leo Tolstoy, who preceded him by thirty-two years and outlived him by another six. The elder realist had much to teach the young doctor, but the precocious pupil forged boldly ahead into the faster rhythms, smaller forms, and telegraphic style fit for the coming century of progress, speed, and shortened attention


  • Publishers Weekly, starred online review, 11/3/08
    “Makes a thorough guide…An insightful, practical outline of Chekhov’s literary approach. Following Lencek’s intelligent introduction, advice is helpfully broken down by topic…Both Chekhov’s correspondence and his excerpts prove interesting and illustrative…Including a ‘who’s who’ of Chekhov’s pen pals and suggestion for further reading, this is a useful and smart guide for writers of all kinds.”

    Augusta Metro Spirit, 11/19/08
    “A masterpiece of writing advice…a perfect companion for writers at any stage of the craft.”

    The Writer, 2/09
    “What’s new and particularly noteworthy in this volume is a focus on lessons to be learned from a close reading of The Island of Sakhalin.”

On Sale
Oct 23, 2008
Page Count
360 pages

Anton Chekhov

About the Author

Piero Brunello is a professor at the University of Venice.

Lena Lencek is a professor at Reed College in Portland, Oregon.

Learn more about this author