Learn to Write like Chekhov
10 lessons from the Master of Short Stories
6 min readNov 9, 2024
Chekhov skilfully uses nuanced techniques to add depth and realism to his stories. By observing these strategies, new writers can learn how to subtly incorporate meaning, evoke emotions, and create complex characters in their own storytelling.
1. Show, Don’t Tell
- Lesson: Chekhov often conveys emotions and themes through subtle, everyday actions instead of directly stating them. For instance, a character’s hesitation to speak or their gaze at a particular object can say more than pages of description.
- Takeaway: Use imagery, gestures, and indirect dialogue to reveal character emotions and relationships. Avoid spelling out everything for the reader — trust them to interpret the story’s deeper layers.
2. Embrace Realistic Characters
- Lesson: Chekhov’s characters are rarely heroes or villains; they are complex, flawed, and human. They represent ordinary people with relatable struggles, making his stories resonate universally.
- Takeaway: Focus on building believable, multi-dimensional characters. Allow them to have flaws, doubts, and contradictions, making them feel like real people.
3. Master the Art of Subtext
- Lesson: In many of his stories, such as The Lady with the Dog, Chekhov doesn’t spell out the characters’ emotions or the moral of the story. Instead, he leaves certain things unsaid, creating an air of mystery and realism.
- Takeaway: Practice layering your writing with unspoken meanings. Allow characters to communicate indirectly, adding depth and leaving space for the reader’s interpretation.
4. Focus on Everyday Life
- Lesson: Chekhov believed that “art should prepare us for reality.” His stories often focus on mundane events — family dinners, walks, conversations — that reveal profound insights about human nature.
- Takeaway: Don’t underestimate the impact of writing about ordinary moments. Sometimes, small, everyday occurrences can reveal more about life than grandiose events.
5. Economy of Language
- Lesson: Chekhov was a master of brevity. He used concise, simple language to create vivid scenes and powerful emotions without over-explaining or embellishing.
- Takeaway: Avoid overly flowery descriptions or excessive detail. Aim to say as much as possible with as few words as necessary, letting each sentence carry its weight.
6. Understand the Power of Ambiguity
- Lesson: Chekhov’s stories often end with ambiguity, leaving readers with questions and possibilities rather than concrete answers. This approach respects the complexity of real life and allows readers to ponder the story long after finishing it.
- Takeaway: Embrace open endings or ambiguous outcomes. Real life rarely offers tidy conclusions, and leaving some questions unanswered can make your story more thought-provoking and memorable.
7. Avoid Moralizing
- Lesson: Unlike many writers of his time, Chekhov refrained from imposing a moral message. Instead, he presented characters and events without judgment, allowing readers to draw their own conclusions.
- Takeaway: Resist the urge to “teach” a lesson or push an agenda in your story. Trust the reader to find meaning on their own, focusing instead on creating an authentic portrayal of life.
8. Use Setting to Reflect Emotions
- Lesson: Chekhov subtly used settings to mirror the emotional states of his characters. For example, bleak landscapes often reflect inner turmoil, while cheerful scenes might accompany lighter moments.
- Takeaway: Think of setting as a tool to enhance mood and deepen themes. Describe environments in a way that complements the inner world of your characters.
9. Capture the Internal Conflict
- Lesson: Chekhov’s characters often face internal conflicts — ambition versus apathy, love versus duty — that shape their actions and decisions.
- Takeaway: Realistic characters are seldom fully certain of their choices. Introduce internal struggles that make your characters more relatable and layered, as these conflicts often resonate most with readers.
10. Allow for Self-Reflection
- Lesson: Chekhov’s characters often reflect on their actions and choices, which adds depth and realism to their personalities. This introspective quality helps readers connect with them on an emotional level.
- Takeaway: Show characters reflecting on their own actions or choices, offering glimpses into their inner lives and making their motivations more transparent to readers.
Let’s delve into examples from Chekhov’s stories that illustrate each of these storytelling techniques.
1. Show, Don’t Tell
- Example: The Kiss — In this story, Chekhov describes Ryabovich, a shy officer, who is accidentally kissed in the dark by a woman who mistakes him for someone else. Rather than directly stating his emotions, Chekhov conveys Ryabovich’s wonder and excitement through his actions and thoughts afterward, showing the powerful effect of a single moment on a lonely man’s psyche.
2. Embrace Realistic Characters
- Example: The Man in a Case — The main character, Belikov, is a timid, overly cautious man who clings to rules and routine, fearing change. Chekhov portrays him with depth and realism, capturing his insecurities and peculiarities. Belikov is flawed and sometimes frustrating, yet relatable, representing the limitations we all impose on ourselves.
3. Master the Art of Subtext
- Example: The Lady with the Dog — The story explores a complex relationship between Anna and Gurov, two people trapped in loveless marriages who find comfort in each other’s company. Chekhov doesn’t spell out their love; instead, he uses subtle body language and indirect dialogue to convey their mutual longing and the emotional depth of their relationship.
4. Focus on Everyday Life
- Example: In the Cart — This story follows Marya Dmitrievna, a schoolteacher traveling in a cart back to her village after picking up supplies. Through her quiet journey, Chekhov explores her life’s struggles and disappointments, highlighting the weight of her lonely existence through her thoughts and memories. There is no grand climax, just the poignancy of her everyday reality.
5. Economy of Language
- Example: Misery — In this brief but impactful story, Chekhov tells of Iona, a cab driver grieving the recent death of his son. Through short, precise sentences, he captures Iona’s sorrow and longing for someone to share his pain with. Each word is carefully chosen, allowing the reader to feel the depth of Iona’s loneliness without needing extensive exposition.
6. Understand the Power of Ambiguity
- Example: The Student — At the end of this story, a young seminary student feels an intense, inexplicable connection to his ancestors and the biblical story of Peter’s betrayal of Christ. The story ends ambiguously, with the student feeling “joyful and warm.” It’s unclear whether this is a spiritual awakening or simply a passing mood, leaving readers to interpret the ending based on their own beliefs and experiences.
7. Avoid Moralizing
- Example: Ward №6 — Chekhov explores the story of Dr. Ragin, a hospital doctor who becomes a patient in his own asylum. Rather than judging Ragin or his treatment of patients, Chekhov presents his transformation neutrally, showing the absurdity of his ideals without directly condemning him. Readers are left to draw their own conclusions about mental health and institutional cruelty.
8. Use Setting to Reflect Emotions
- Example: Gooseberries — In this story, the rural setting reflects the protagonist Ivan Ivanych’s moral struggle and disillusionment. As he tells the story of his brother’s misguided search for happiness, Chekhov uses the bleak countryside to mirror Ivan’s cynicism about life’s simple pleasures and people’s endless desires, symbolized by his brother’s obsession with having a gooseberry farm.
9. Capture the Internal Conflict
- Example: An Anonymous Story — The protagonist, a man secretly spying on a revolutionary, finds himself in a moral quandary as he develops feelings for the revolutionary’s wife. Chekhov reveals his inner turmoil and self-doubt, capturing the conflict between loyalty to his mission and personal desires, which lends depth to the story’s psychological tension.
10. Allow for Self-Reflection
- Example: The Darling — This story centers on Olenka, a woman who takes on the personalities and interests of the men she loves. At first glance, Olenka’s behavior may seem shallow, but Chekhov gives her moments of introspection, allowing readers to see her own quiet realization of her dependence on others. This self-reflection adds complexity to her character, making her journey poignant rather than merely pitiable.
