20 Books That Prove Creative Risks Are Worth Taking
Here’s a chronological journey of twenty novels that broke the rules, expanded the possibilities of fiction, and continue to remind every writer that the boldest choice is often the most memorable.
July Theme: Creative Courage
Big Question: What does it take to begin, risk, and share what you create?
Week 2: Taking Creative Risks
This week, we’re discussing what it means to take creative risks, so I thought it would be a good idea to discuss a few novels that are courageous because of the risks they took. This is not a complete list by any means but still includes many works worth reading and studying.
Every memorable book exists because an author decided to risk something. Sometimes that risk was commercial and had to do with publishers’ and readers’ expectations. Sometimes it was structural and had to do with bending or ignoring conventional literary forms. Sometimes it was emotional and pushed more intangible boundaries. And sometimes it meant ignoring every piece of conventional writing advice available.
Many of the books below puzzled critics, challenged publishers, or seemed impossible to market. Yet they endured because their authors trusted an idea that felt unconventional but authentic. They didn’t set out to be different for the sake of being different, however. Instead, they found the form that best served the story they wanted to tell or even needed to tell.
As writers, we don’t have to reinvent the novel every time we sit down to write, but we do have to ask one uncomfortable question: What am I afraid to try? And why?
This week’s reading list explores twenty books that answered that question with remarkable creative courage. Arranged chronologically, they reveal how literary innovation has evolved over the centuries while reminding us that every groundbreaking book began as someone’s risky idea.
Breaking the Rules of the Novel (1759–1931)
1. The Life and Opinions of Tristram Shandy, Gentleman (1759) by Laurence Sterne
The Risk
Before the concept of the novel had settled into recognizable conventions, Sterne gleefully ignored them. He interrupted his own story, wandered into lengthy digressions, spoke directly to readers, and even played with the physical page in this work. This work is widely considered one of the earliest and most radical examples of the metafictional anti-novel.
Why It Worked
The structure becomes part of the storytelling. Instead of simply following a plot, readers experience the unpredictable workings of a brilliant, restless mind.
Read Next
Pale Fire by Vladimir Nabokov
If on a winter’s night a traveler by Italo Calvino
Writers: Sometimes the way you tell the story is just as important as the story itself.
2. Pride and Prejudice (1813) by Jane Austen
The Risk
At a time when novels often centered on grand adventures or gothic melodrama, Austen focused on ordinary conversations, family dynamics, and the social expectations placed on women.
Why It Worked
She demonstrated that emotional tension and sharp observation could be just as compelling as action.
Read Next
Middlemarch by George Eliot
Jane Eyre by Charlotte Brontë
Writers: Never underestimate the power of well-defined characters and a strong voice to carry a story.
3. The Waves (1931) by Virginia Woolf
The Risk
Woolf abandoned a traditional plot in favor of lyrical interior monologues that blur the boundaries between six different consciousnesses.
Why It Worked
The novel captures emotional truth in ways conventional narration cannot.
Read Next
The Sound and the Fury by William Faulkner
The Unnamable by Samuel Beckett
Writers: Not every story needs a conventional plot if its emotional journey is compelling enough.
Creative courage isn’t about breaking rules. It’s about discovering which rules your story doesn’t need.
Reinventing Narrative (1962–1984)
4. Pale Fire (1962) by Vladimir Nabokov
The Risk
A novel disguised as the annotations to a fictional poem, this work reinvented the novel by discarding the traditional linear narrative in favor of an interactive, jigsaw-puzzle structure. It is presented entirely as a 999-line poem written by a fictional poet, enclosed by a foreword, exhaustive commentary, and an index by a delusional, self-absorbed academic.
Why It Worked
Readers gradually realize the commentary tells an entirely different—and increasingly unreliable—story.
Read Next
House of Leaves by Mark Z. Danielewski
The Blazing World by Siri Hustvedt
Writers: Structure can create mystery before a single plot twist occurs.
5. Hopscotch (1963) by Julio Cortázar
The Risk
Readers can choose to follow different reading orders, creating different experiences of the same novel in this work. The novel can be read in two primary ways. Readers can follow a traditional path through the first 56 chapters, or they can follow a randomized, zigzagging path between chapters scattered throughout a second, surreal section.
Why It Worked
This novel’s unconventional structure mirrors the uncertainty and fragmentation of modern life. Cortázar transformed the reader from a passive consumer into an active participant by providing a “Table of Instructions” that maps out a path skipping back and forth through its 155 chapters.
Read Next
Dictionary of the Khazars by Milorad Pavić
Composition No. 1 by Marc Saporta
Writers: Experiment only when the form reinforces the theme.
6. In Cold Blood (1966) by Truman Capote
The Risk
Capote blended meticulous journalism with the techniques of literary fiction, helping define the modern true crime narrative.
Why It Worked
Readers experience real events with the emotional depth and narrative momentum of a novel.
Read Next
The Executioner’s Song by Norman Mailer
Killers of the Flower Moon by David Grann
Writers: Borrowing techniques from another genre can transform your own.
7. One Hundred Years of Solitude (1967) by Gabriel García Márquez
The Risk
The extraordinary is treated as completely ordinary in this novel, forever establishing magical realism as a literary force. This novel dismantled linear time, using cyclical, multi-generational repetition to mirror trauma. It also introduced deep metafiction, as the novel itself acts as a prophecy unraveling into text.
Why It Worked
Fantasy deepens the emotional and historical truths present in the novel rather than distracting from them.
Read Next
Beloved by Toni Morrison
The House of the Spirits Isabel Allende
Writers: The impossible becomes believable when your characters accept it without question.
8. If on a winter’s night a traveler (1979) by Italo Calvino
The Risk
The novel’s second-person ‘You’ framework turns the reader into the protagonist, whose quest to finish ten mysteriously interrupted stories transforms into a meta-fictional exploration of how and why we consume literature.
Why It Worked
The novel transforms the act of reading into the story itself.
Read Next
The Raven Tower by Ann Leckie
A Small Place by Jamaica Kincaid
Writers: Invite readers to participate instead of simply observe.
9. Neuromancer (1984) by William Gibson
The Risk
In this novel, Gibson imagined cyberspace, artificial intelligence, and digital culture long before they entered everyday life.
Why It Worked
The world created in this novel felt authentic enough to influence decades of science fiction.
Read Next
Snow Crash by Neal Stephenson
Altered Carbon by Richard K. Morgan
Writers: Bold ideas become timeless when grounded in believable human stakes.
Today’s genre convention was yesterday’s creative gamble.
Experimentation Goes Mainstream (2004–2021)
10. Cloud Atlas (2004) by David Mitchell
The Risk
In this novel, Mitchell stitched together six seemingly unrelated stories spanning centuries, continents, and genres—from historical fiction to dystopian science fiction. The novel’s nested structure asks readers to trust that the pieces will eventually form a meaningful whole.
Why It Worked
Each story echoes the others, creating a meditation on power, connection, and the ways human choices ripple across generations. The ambitious structure rewards careful readers with a richer understanding of the whole.
Read Next
Station Eleven by Emily St. John Mandel
Cloud Cuckoo Land by Anthony Doerr
Writers: Big ideas become manageable when every individual piece can stand on its own.
11. A Visit from the Goon Squad (2010) by Jennifer Egan
The Risk
Rather than following one protagonist in a linear narrative, Egan created an interconnected novel of linked stories, including a chapter told entirely through a PowerPoint presentation.
Why It Worked
Every stylistic shift serves character development and plot themes, showing how time, memory, and technology reshape our lives.
Read Next
Olive Kitteridge by Elizabeth Strout
Trust by Hernan Diaz
Writers: Innovation succeeds when it deepens our understanding of characters rather than distracting us from them.
12. Grief Is the Thing with Feathers (2015) by Max Porter
The Risk
Part novella, part prose poem, part fable, the story introduces Crow—a mythic, mischievous figure—as grief itself. Typography, fragmented narration, and poetic language replace traditional storytelling.
Why It Worked
Its unconventional form captures the fractured, nonlinear experience of mourning more truthfully than a conventional narrative could.
Read Next
Isaac and the Egg by Bobby Palmer
Dept. of Speculation by Jenny Offill
Writers: Sometimes emotions demand a new form of storytelling.
13. Solar Bones (2016) by Mike McCormack
The Risk
The entire novel unfolds in a single, unbroken sentence as a dead engineer reflects on his ordinary life from beyond the grave.
Why It Worked
The flowing sentence mirrors the continuity of memory itself, transforming an ordinary existence into something quietly profound.
Read Next
Ducks, Newburyport by Lucy Ellmann
Transit by Rachel Cusk
Writers: A bold formal constraint can create surprising emotional freedom.
14. Lincoln in the Bardo (2017) by George Saunders
The Risk
Saunders assembled hundreds of voices—both historical and fictional—into a ghostly chorus that blends archival fragments, imagined testimony, and dramatic dialogue in this novel.
Why It Worked
The many voices in this novel create a deeply human portrait of grief, love, and loss while allowing history and imagination to coexist.
Read Next
Savage Conversations by LeAnn Howe
Ironweed by William Kennedy
Writers: Every character sees the same story differently, and that’s where complexity lives.
Innovation eventually becomes tradition. Every rule-breaking novel gives future writers permission to be bolder.
15. Exhalation (2019) by Ted Chiang
The Risk
Rather than relying on spectacle or action, Chiang builds stories around philosophical questions about consciousness, free will, memory, and humanity in this work.
Why It Worked
His ideas are intellectually rigorous yet emotionally resonant, proving that speculative fiction can illuminate the deepest questions about what it means to be human.
Read Next
Axiomatic by Greg Egan
The Paper Menagerie by Ken Liu
Writers: Readers will follow complex ideas when they care about the people exploring them.
16. Interior Chinatown (2020) by Charles Yu
The Risk
Yu tells the entire novel as a screenplay, using scene headings, stage directions, and casting language to examine identity, race, and the roles society assigns us.
Why It Worked
The screenplay format becomes a metaphor for how people perform expectations placed upon them, making the structure inseparable from the novel’s message.
Read Next
Erasure by Percival Everett
Yellowface by R. F. Kuang
Writers: Choose the storytelling form that best amplifies your theme, even if it surprises your readers.
17. No One Is Talking About This (2021) by Patricia Lockwood
The Risk
Lockwood translated the fragmented rhythms of social media into literary fiction, capturing the strange mixture of humor, distraction, absurdity, and heartbreak that defines online life in this novel.
Why It Worked
The novel mirrors how modern consciousness actually works, shifting rapidly between memes, headlines, private thoughts, and profound personal loss.
Read Next
Dept. of Speculation by Jenny Offill
Fake Accounts by Lauren Oyler
Writers: Your writing doesn’t have to imitate the past to become timeless.
Today’s Boldest Storytelling (2023–Present)
18. The Spear Cuts Through Water (2022) by Simon Jimenez
The Risk
Jimenez reimagines epic fantasy by layering multiple narrative perspectives and storytelling frames. The novel shifts between first-, second-, and third-person narration, unfolds as a myth remembered through a theatrical performance, and asks readers to become active participants in piecing together the story. It’s an audacious structure that could have easily become confusing but instead becomes unforgettable.
Why It Worked
Every narrative layer serves the novel’s central themes of memory, legacy, love, and the transformative power of storytelling. The experimental structure never overshadows the emotional journey but instead deepens it.
Read Next
Black Leopard, Red Wolf by Marlon James
The Fifth Season by N. K. Jemisin
Writers: Your structure should amplify your story’s emotional impact, not simply organize its events. When form and theme work together, readers experience the story rather than just read it.
19. Fourth Wing (2023) by Rebecca Yarros
The Risk
Yarros blended epic fantasy, military academy training, dragon lore, romance, and high-stakes action into a fast-paced series of novels that appealed to both fantasy veterans and readers new to the genre. At a time when publishers often categorized books narrowly, Fourth Wing embraced crossover storytelling.
Why It Worked
By balancing immersive world-building with emotionally compelling relationships, the novel became a cultural phenomenon and helped propel Romantasy into the mainstream.
Read Next
A Court of Thorns and Roses by Sarah J. Maas
The Serpent and the Wings of Night by Carissa Broadbent
Writers: Don’t be afraid to combine the genres you love. Your readers probably enjoy more than one, too.
20. James (2024) by Percival Everett
The Risk
Everett revisits one of the most recognizable novels in American literature, Adventures of Huckleberry Finn, by shifting the narrative to Jim’s perspective. Rather than simply retelling a familiar story, he reclaims a voice that had long been marginalized, blending satire, historical fiction, and literary critique into a novel that challenges readers to reconsider whose stories are told, and who gets to tell them.
Why It Worked
By transforming a literary classic through a new perspective, Everett demonstrates that innovation doesn’t always require inventing something entirely new. Sometimes the boldest creative act reveals what has always been missing.
Read Next
March by Geraldine Brooks
Homegoing by Yaa Gyasi
Writers: Every story contains untold perspectives. Ask yourself whose voice has been overlooked, and what changes when they become the one holding the pen.
Creative courage isn’t about being different for the sake of it. It’s about choosing the form, voice, or perspective that allows your story to say what no conventional approach could.
Final Reflections
Looking across more than 250 years of literature, one thing becomes clear: none of these books became memorable because they chased trends or copied conventions. They became memorable because their authors trusted an idea that felt uncertain.
Creative courage doesn’t always require something as big as inventing a new genre or writing a thousand-page sentence. But it does often mean choosing the ending everyone tells you to avoid. Writing the character who refuses to be likable. Blending two genres that shouldn’t ‘fit’ together. Or finding a narrative voice that sounds unlike anyone else’s.
Yet the risk itself isn’t the goal. The goal is to discover the style, form, voice, or perspective that makes your writing and stories impossible to mistake for anyone else’s.
Before you begin your next writing session, ask yourself: What’s one creative choice I’ve been avoiding because it feels too risky? Then try it. Maybe it won’t work. Maybe you’ll revise it tomorrow. Or maybe you’ll discover the exact thing your story needed all along.
Let me know what you’d add to this list in the comments and don’t forget to join our chats this week, where we’ll be talking about what it means to take creative risks.
I would love to learn more about what you think, and what you’re reading and writing!
And please don’t forget to like and share this post if you enjoyed it, so others can enjoy it too. Thank you!
Want to read with us?
Egalitarian Book Club is currently reading
Poverty, By America by Matthew Desmond.
Week 1 (July 1-5 )— Prologue- Chapter 1
Week 2 (July 6-12)— Chapters 2-4
Week 3 (July 13- 19)— Chapters 5-7
Week 4 (July 20-31) — Finish Book
July 31st: Discuss entire book in Substack chat thread
Continue Exploring July’s Creative Courage Theme
This week’s Posts: Taking Creative Risks
Taking Creative Risks: Writing Prompts to Build Creative Courage
Should writers prioritize creative risks or readers’ expectations?
Week 1: Beginning Before You Feel Ready
Beginning Before You Feel Ready: Writing Prompts
Do writers need to feel ready before they begin a new project?
Beginnings and endings are linked in a lot of ways…
Why Beginning Feels So Difficult, But Doesn’t Have to Be
Books That Made Me Want to Write and Take Creative Risks
Consider going more in depth with this month’s theme with July’s Creative Courage Writing Collection.
The writing collection is designed to help you explore creative courage from different angles: discovering your voice, strengthening your craft, experimenting with new approaches, and reflecting on the writer you are becoming.
The free Books, Drafts, and Dialogues posts that will be published this month will explore the outward side of creative courage—beginning, risking, and sharing— and should complement this collection quite well, which invites you to go much deeper into the internal work of creativity with 30 guided writing prompts and craft exercises, reflections, as well as three options for guided monthly writing challenges for those who want to go even further than that.