Anton Chekhov’s 6 Rules for a Great Story

Anton Chekhov’s 6 Rules for a Great Story

Mastering the essential complementarity of compassion and total objectivity.


Anton Chekhov’s 6 Rules for a Great Story

“Use the time of a total stranger in such a way that he or she will not feel the time was wasted,” Kurt Vonnegut offered in the first of his 8 tips for writing a good story. “A good story and a well-formed argument are different natural kinds,” the pioneering Harvard psychologist Jerome Bruner observed in his essay on what makes a great story. “Both can be used as means for convincing another. Yet what they convince of is fundamentally different: arguments convince one of their truth, stories of their lifelikeness.” What, then, makes for maximally convincing lifelikeness in a story that leaves the reader grateful for the time spent reading it?

That is what Anton Pavlovich Chekhov (January 29, 1860–July 15, 1904) examined in a letter to his brother Alexander, included in the 1973 volume Anton Chekhov’s Life and Thought: Selected Letters and Commentaries (public library),

Anton Chekhov (Portrait by Osip Braz, 1898)

Writing on May 10, 1888, Chekhov lays out his six tenets of a great story:

  1. Absence of lengthy verbiage of a political-social-economic nature
  2. Total objectivity
  3. Truthful descriptions of persons and objects
  4. Extreme brevity
  5. Audacity and originality: flee the stereotype
  6. Compassion

Embedded in the complementarity rather than contradiction of the second and the sixth — total objectivity and compassion — is the recognition that no depiction of reality is realistic unless it include an empathic account of all perspectives, which might be the defining characteristic not only of Chekhov as a writer but of any great storyteller.

Chekhov had put his own principles to fine use — that year, his short story collection At Dusk won him the prestigious Pushkin Prize, named after his famed compatriot Alexander Sergeyevich Pushkin (June 6, 1799–February 10, 1837), who had articulated a remarkably similar philosophy of storytelling half a century earlier.

In a fragment from 1830, Pushkin considers what makes a great dramatist — the most esteemed species of storyteller in the era’s ecosystem of literature — and lists the following necessary qualities:

A philosophy, impartiality, the political acumen of a historian, insight, a lively imagination. No prejudices or preconceived ideas. Freedom.

Complement with Chekhov — a lover of lists — on the 8 qualities of cultured people, then revisit other abiding advice on the craft from great writers: Susan Sontag on the art of storytelling, Jeanette Winterson’s 10 rules of writing and another 10 from Zadie Smith, Henry Miller’s 11 commandments, John Steinbeck’s 6 guideposts, Jack Kerouac’s 30 “beliefs & techniques” for writing and life, Eudora Welty on the art of narrative, Kurt Vonnegut on the shapes of stories, James Baldwin’s advice to writers, and Ernest Hemingway’s reading list of essential books for every aspiring writer to read.


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