In this episode, we explore the life and legacy of Anton Chekhov—a writer whose quiet revolution in storytelling continues to shape how we understand modern life. The first such discussion between Alex Burry, a lit professor at Ohio State University and Lev Lesokhin, a tech exec and lifelong reader of Chekhov.
Born into a lower-middle-class family—the grandson of a serf who bought his freedom and the son of a struggling shopkeeper—Chekhov stood apart from many of his aristocratic contemporaries. His early experiences, along with his work as a physician treating peasants and laborers, shaped a literary vision grounded not in grand heroics but in the fragile dignity of ordinary people. His stories unfold in drawing rooms and provincial towns, over tea and casual conversation, where life’s most consequential decisions are postponed, deflected, or left unspoken.
We take a closer look at Chekhov’s so-called “trilogy of inaction”—The Man in a Case, Gooseberries, and About Love—three interconnected stories in which almost nothing happens, and yet so much is revealed. A marriage never proposed, a love never pursued, a life quietly narrowed by habit and fear: Chekhov shows how the drama of existence often lies in what fails to occur and how our own fears and wants can push us to extremes.
Along the way, we draw unexpected parallels between Chekhov’s characters and contemporary social language—“main character syndrome,” “the ick,” “situationships,” and the comedy of everyday awkwardness. Like today’s “shows about nothing,” his work finds humor and heartbreak in the mundane, capturing the subtle absurdities of social interactions with uncanny precision.
We also consider Chekhov’s intellectual relationship with Leo Tolstoy, whose moral seriousness and independent spirituality he admired, even as he remained personally nonreligious. And we explore Chekhov’s environmental imagination, reflected in figures like Dr. Astrov from Uncle Vanya, a character who plants trees as an act of faith in the future.
Though Chekhov once predicted his work would be forgotten within ten years of his death, this conversation argues the opposite: his pitch-perfect ear for human hesitation, compromise, and longing makes him feel not only modern, but urgently contemporary.