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Doodling with Dostoevsky

Taylor Rebhan
June 11, 2024 | 8 min read

Fyodor Mikhailovich Dostoevsky. World-renowned author. Master of the psychological novel. Troubled gambler. Political prisoner. Prolific … doodler?

Open the notebooks of one of the world’s most cherished and revered authors and you’ll find words, of course. Many of his notebook pages are filled with tiny, cursive Cyrillic sentences arranged on the page in a way that could have only made sense to the author himself (relatable). The writing winds up and down, is divided into not-so-neat bubbles and columns, and follows the wandering paths of his mind.

But tucked in between the paragraphs of notes, brick-and-mortared by calligraphy and penmanship practice, there are hundreds upon hundreds of doodles.

They’re peppered throughout the author’s manuscripts, from his earliest works to his masterpieces to his personal diaries. Throughout his writing career, Dostoevsky penned, penciled, and sketched away. He was so prolific, his drawings have spawned entire museum exhibits and books of scholarship.

Those of us who remember drawing the famous “Cool S” on our math homework (or, for the delinquents out there, on our desks) can relate. But Dostoevsky’s doodles are more than just random scribbles and graffiti. They aren’t crude. In fact, they’re far from it. Architecture is proportionally rendered. Faces are expressive, not flat. His characters often look like they’re caught in the middle of overwhelming emotion. Just as in his writing, Dostoevsky has his own unique style.

So, what can this master writer’s doodles in the margin teach us about first drafts?

Look no further than his perhaps most widely read work: Crime and Punishment.

The early manuscripts hew closely to the final product. In fact, there are entire paragraphs and sequences that are largely unchanged from first to last draft.

But one major change shaped the structure and effect of the novel drastically.

And we can understand it by looking in an unlikely place: The doodles in the margins.

 

Lesson One: Change Your Point of View

Crime and Punishment was published in a magazine in several parts over the course of a year — a serial novelization. Although its publication happened in stages, Dostoevsky had the kernel of the story in his mind for years.

The novel centers on a twenty-something ex-student in 19th Century Russia, Rodion Raskolnikov. Highly intelligent and miserably impoverished, Raskolnikov misguidedly believes that he can justify a crime if his motives serve a higher good — namely, raising himself out of destitution so that he can do great, moral things. Having hatched his plan and rationalized it to himself, he works up the nerve to murder and rob an old woman — a pawnbroker — setting the events of the novel into motion.

What begins as the “perfect” amoral crime in both mind and method soon devolves into a nightmare marked by physical and mental illness, police pursuit, near-constant paranoia, spiritual soul searching, the near-dissolution of his family, and ultimately the spiritual and psychological punishment Raskolnikov believed he would be immune to.

That’s the novel in a nutshell, and it’s what Dostoevsky always intended it to be. If you’ve heard of stories “revealing themselves” to authors and surprising them as they write, that’s not the case here. He saw the arc, and simply needed to put it down.

Only, it wasn’t that simple. Getting from A to B troubled Dostoevsky to the point where he wrote in a letter to a friend that he burned an early draft in his fireplace.

But there was a solution to his struggle. It was just hiding in the margins.

Dostoevsky was telling the story in his drawings long before he figured out how to do it in writing.

The Crime and Punishment drafts are rife with doodles. A few feature Raskolnikov, others more minor characters.Church towers and town squares loom above. There’s even a self-portrait of Dostoevsky himself.

Each portrait wears an unforgettable expression.

Pensive and reflective.

Eyes screwed shut in pain.

Brows furrowed in anger.

Even a fewsmug faces appear — no doubt of Luzhin and several of the other contrasting characters in the novel.

But it’s the portraits of Raskolnikov that are the key to unlocking the major change from first draft to finished product.

Dostoevsky originally wrote Crime and Punishmentin the first-person point of view, as a confessional of sorts, beginning only after Raskolnikov has murdered the pawnbroker. A memoir, a diary, a confession — a mix of both. But it just wasn’t working.

And the doodles show why.

The drawings of minor characters could theoretically be from Raskolnikov’s point of view. Dostoevsky is simply sketching what our protagonist sees.

But the anguished young Raskolnikov couldn’t see himself the way Dostoevsky sketched him. Only someone else could. 

Therein lies the breakthrough: To truly demonstrate his deeply wounded psychological state, Raskolnikov had to be seen through the eyes of others. Not just his own.

So Dostoevsky shifted to the third-person narrator — but with an innovative twist. He still narrated Raskolnikov’s inner thoughts with the first-person. We still get to experience his paranoia, guilt, and struggle first-hand.

But now, when the point of view steps back, Raskolnikov is also humanized. Instead of simply experiencing him through the most dramatic—and traumatic—event in his life, we see him in three dimensions. We see his deep relationships, his loyalty, and even his humor through the people around him.

Take this moment in Chapter VI, when we see him through the eyes of his closest friend, Dmitri Razoumikhin. Razoumikhin squabbles with a delirious and obviously disturbed Raskolnikov over his plans. Raskolnikov leaves abruptly and heads off on his own.

In a brief but beautifully evocative moment allowed by the third-person narrative, we stay with Razoumikhin instead of following Raskolnikov:

Raskolnikov walked on and turned the corner into Sadovy Street. Razumihin looked after him thoughtfully. Then with a wave of his hand he went into the house but stopped short of the stairs.
“Confound it,” he went on almost aloud. “He talked sensibly but yet... I am a fool! As if madmen didn’t talk sensibly!...” He struck his finger on his forehead. “What if... how could I let him go off alone? He may drown himself.... Ach, what a blunder! I can’t.” And he ran back to overtake Raskolnikov, but there was no trace of him.

By staying with Razoumikhim, we get to feel his compassion and genuine affection for his friend. We see Raskolnikov through his eyes. Instead of a madman and murderer, we see a troubled and helpless friend who ought not to be left alone.

Without the third-person narrative, we would never have been able to feel Razoumikhim’s love manifest as frustration and worry. We would only have Raskolnikov’s unreliable confessional.

A reader can relate to Raskolnikov’s struggles infinitely more when he is complex, and Dostoevsky makes him wonderfully and humanly complicated through those around him. In Chapter III, we experience this moment of his loved ones:

When he had said this, he suddenly held out his hand to his sister, smiling without a word. But in this smile there was a flash of real unfeigned feeling. Dounia caught it at once, and warmly pressed his hand, overjoyed and thankful. It was the first time he had addressed her since their dispute the previous day. The mother’s face lighted up with ecstatic happiness at the sight of this conclusive unspoken reconciliation. “Yes, that is what I love him for,” Razumihin, exaggerating it all, muttered to himself, with a vigorous turn in his chair. “He has these movements.”

And suddenly, we’re hoping Raskolnikov gets away with it. That the old woman really deserved it, after all. We sympathize with his wild philosophy, the one that led him to commit not one, but two brutal murders.

With this masterful stroke of characterization in the third-person narrative, Dostoevsky moves the tension from within the novel into our own hearts and minds.

 

Lesson Two: From Idea to Story

Dostoevsky is famous for writing philosophical novels — that is, stories that explore ideas about how best to live. Crime and Punishment is no different. He explicitly stated that he set out to explore the dangers of a fashionable philosophy of the time, which he called “Radicalism.” It was a post-modern, post-meaning, post-religious movement catching on in the literary and intellectual spheres in 19th Century Russia. In it, there was no fixed truth — all experiences in life were subjective, morally and ethically and otherwise.

In Crime and Punishment, Dostoevsky sought to portray what might happen when a man took these ideas to their logical conclusion.

For some writers, their story is creatively sparked by an event. For others, it’s a character. For still others, it’s a place.

For Dostoevsky, it was an idea.

He wrote to prove, disprove, theorize, philosophize, and argue — often against himself. The inner struggle within a work is one of his hallmarks.

But an idea in and of itself isn’t a story. When the first iterations of his narrative weren’t working, perhaps it was also because it wasn’t a story yet — it was still just an exploration.

A police confession? A memoir? The diary entry of a guilty man? These are clinical, scientific almost. A hypothesis, a test, and a conclusion do not a story make. One can almost see how Raskolnikov the person had not yet appeared, and only Raskolnikov the strawman existed in early drafts. And Dostoevsky has never been known for writing strawmen.

So when Dostoevsky shifted the perspective from the first-person confessional to the third-person, we step out of pure intellectualism and into empathy.

We really see Raskolnikov, for the first time. Not just his philosophy, but his life and his character. He was on the page all along — in the anguished and pensive doodles.

Once the perspective shifts, Raskolnikov isn’t just a vehicle for an idea. He’s a human being, a man torn in two.

This is when the idea became the story we know and love.

So the next time we sit down to write, we can take a page from Dostoevsky’s book. For an idea to be a story, it needs empathy.

 

Lesson Three: Wander, Fixed to the Page

It’s obvious from Dostoevsky’s doodles that the writer, while writing, wasn’t always … well, writing. And yet these manuscripts led to some of our most cherished novels. How is that?

It’s simple. 

He was fixed to the page.

The Writer Ann Lamott calls it putting your butt in the chair (let’s see the Russian translation of that). Dostoevsky followed this rule. When his writing pen stopped, his sketching pen started. But he never left the page — a sign that if writing is thinking, so is doodling.

In fact, that idea is scientifically proven.One study found that doodling improves recall by 29%. Another found that it helps relievepsychological stress. Dostoevsky was plagued by a nervous condition throughout his life. Margins in his manuscripts also contained small calculations and ledgers to keep track of his financial troubles. Perhaps the doodling calmed and soothed his restless mind, helping him back to his work when he was ready.

Doodling has also been attached tothe unconscious. What are we really thinking of when we sketch a tree? How about the architecture of a chapel, like the beauties found in the margins of Crime and Punishment drafts? With its undercurrent of repentance and spiritual resurrection, it’s not hard to see what was on the author’s mind as he penned the story … and his sketches. 

Like a mountain climber, Dostoevsky secured himself to one point — the page — and then began his wandering ascent. He had plenty of switchbacks. He even rested. But notice that he didn’t leave the page. It was him, the rope, and the cliff face of the page.

In the war against distraction, Dostoevsky doodled. He banished his distractions, doubts, and blocks one sweep of the pencil at a time. And then he returned to the next line. And the next line. And the next after that.

So the next time you sit down to write, bring a pad of paper and a pencil. Or maybe a Post-It and a pen. 

Not for writing.

But for doodling.

Rendering what the mind’s eye sees — or perhaps, what it can’t see yet.

It might just change your point of view.

August 26, 2026 5 min read

Freewriter Mike Somerby left a lucrative marketing career in e-commerce to start a print-only literary magazine by and for Montanans. Yes, you read that right.

We sat down with Mike to find out how ... and why.

Mike Somerby identifies as a writer — with some reservation.

"I think all who write are 'writers,'" he says, "even if the writing itself amounts to a simple letter to a friend or a personal journal entry."

We couldn't agree more. And we're thrilled that this particular writer writes his essays on Freewrite. Maybe that's why we felt comfortable asking him:

What inspires a professional brand marketer to leave his 9-5 and jump feet-first into the literary world of Bozeman, Montana?

Luckily, he was happy to tell us.

AC: Before we get into the lit mag, it actually isn't your first foray into the literary community, right?

MS: For about ten years — the lion's share of my professional chapter — I worked, in some capacity, as a brand marketer. Last spring, while enduring a particularly grueling stint as CMO for a Montanan e-commerce brand (yes, those exist), I found myself revisited by the remarks of an old journalism school professor: from his perspective, journalism students who apply their storytelling talents toward PR and marketing have crossed over to "the dark side."

While I find this a touch heavy-handed, I get the point, and I believe his notion resurfaced to meet the moment: we live in a world sorely hurting for analog (human) creativity and high-quality longform.

So I quit, traveled west with my dog in a 1986 U-Haul I'd converted into a camper, and plotted.

Step one: I founded Pulphead, a lounge (named after John Jeremiah Sullivan’s seminal 2011 essay collection) where Bozeman writers commune and grind out their prose until 2 a.m. Entry is a flat $5, which comes with unlimited drip coffee and tea.

Step two: leverage the Pulphead regulars and its online following to secure contributors for my new literary magazine, ANEMONE. Thus far, everything is going to plan.

We live in a world sorely hurting for analog (human) creativity and high-quality longform.

AC: Why do you think it's so important to create and preserve these spaces for authentic writing?

MS: Writing is a solitary act. Nonetheless, younger generations, in particular, struggle to forge IRL community in the way older generations might understand as an ordinary facet of being human.

By building a space that is as homey as it is supportive of their literary interests, we’re not only helping these individuals find their birds of a feather, but also providing them with a dojo that mandates setting aside blocks of time away from phones, home lives, and the other distractions. Win-win?

Incidentally, Livingston boasts the highest per-capita concentration of professional writers anywhere in the country. Couple this with another statistic — that Montana has more bookstores per capita than any other state — and it becomes clear southwest Montana is as fertile a place as any to invest in literature and its related industries.


AC: That's so interesting. What have you learned from being in community with creatives in Bozeman?

MS: In terms of writing, I've learned plenty. What has excited me most, however, is what I’ve learned from a small group of Indigenous women who come to the shop to write poetry and make beaded clothing in the traditions of their respective tribes (most notably, Crow, Cheyenne, Shoshone).

This is a group I’d otherwise have limited opportunity to engage with outside of Pulphead, and learning about their traditions, beliefs, hopes — even a little vocabulary — through firsthand conversation has proved incredibly edifying.

AC: And you mentioned you've seen Freewrites pop up in Pulphead. You use one, right?

MS: Yes. About seven years ago, not long after moving to Montana from New York, I purchased an Olivetti Lettera 32 typewriter from eBay. It appeared that a romanticizing of my newfound remoteness had rekindled my interest in writing.

I loved the mechanical feel and distraction-free interface, but the inability to edit line by line proved a notable annoyance for a mind habituated to modern computers. A few years down the road, some digging for alternatives led me to a blog post about smart/electronic typewriters. Voilà.

I purchased a Freewrite Gen3 Smart Typewriter, and I've been hooked ever since.

AC: That's awesome. So tell us about ANEMONE. What is it?

MS: ANEMONE is a print-only magazine (printed in a traditional broadsheet newspaper format). As for for theme, broadly, the world as told by Montanans. Short fiction, creative nonfiction, poetry, reportage, photography, and visiual illustrations comprise the submission categories.

AC: Print-only!

MS: Print is only dying because we let it.

AC: Is there a story about the name?

MS: Most people know the word anemone to describe a family of flowers — a 200-plus-species family of buttercups, comprising varieties both wild and domesticated. Dubbed “windflowers,” their delicate petals are said to blow open in the breeze; the ancient Greek word anemos means “wind.” I was drawn to the metaphorical value of beauty and how it can be revealed to us through an invisible force.

To add another layer, when I was a boy my father and I would spend weekends at the beaches north of San Francisco, where I was born and raised until I was seven. We would study the massive turqoise, kelly green, and purple sea anemones clinging to rocks left exposed by the receding Pacific tides (as to why, I can't say, outside of them looking funny, almost alien). A good memory.

Finally, “Anemone” is the name of an exquisite song by The Brian Jonestown Massacre, an irreverent and controversial rock band led by Anton Newcombe, an obsessive creative who rejects the surrender of culture and art to commercial interests. The track has a hold on me. It's like a portal to another era.

AC: Why do you think this sort of analog creativity is important?

MS:  I'm told the unending deluge of digital interface is leaving humans less and less capable of “deep work.” Will we ever know the difference?

Will we recognize what a society incapable of deep work looks like compared with those that came before it? Or will the transition manifest as a gradual degradation of quality, much as Coca-Cola was slowly, but surely, divorced from real sugar, such that to taste what Coke used to be like, one must order a Mexican Coke, still made with real cane sugar?

For me, analog perspective (and any creativity wrung from it) is rooted in continuity, tangibility, lived experience, slowness, spatial relation, nuance, emphasis on process, and grace for imperfection — antithetical to one of replicability, speed, binary outcomes, predictability, and optimization.

I prefer the former, and I suspect those who prefer the latter don't read or write much — life is a beautiful, taxing mess, and good writers find merit in this duality.

For me, analog perspective (and any creativity wrung from it) is rooted in continuity, tangibility, lived experience, slowness, spatial relation, nuance, emphasis on process, and grace for imperfection — antithetical to one of replicability, speed, binary outcomes, predictability, and optimization.

AC: Who is invited to submit to ANEMONE?

MS: We do limit submissions to Montanans, past and present, though we will feature writers from other states should the content of their writing bear an obvious relation to Montana — a requirement not imposed on Montanan writers.

All information regarding submissions can be found at www.anemonereview.com, along with all other facets of the magazine.

August 26, 2026 1 min read

Love the Freewrite 500? Here are 3 more writing contests for competitive short fiction writers.

1) Writers' Hour Magazine Prompts

The London Writer's Salon (a global writing group — no London residence necessary!) regularly host a writing contest via their Writers' Hour Magazine. Want to know a secret? Their September theme is all about freewriting.

Join them for a free workshop, Introduction to Freewriting, on Thursday, September 3, and get all the details about the contest.

The winner of the contest will win something Freewrite-shaped. 👀

2) NYC Midnight Challenges

This organization (again, no affiliation with NYC necessary) regularly hosts short story contests. Their next challenge is all about writing a rhyming story.

Learn more and register here.

Note: NYC Midnight writing contests generally have a fee to enter.

3) Henshaw Press Short Story Competition

This short story competition is open to anyone over age 16. And the best part? There is a cash prize, and profits go to charity.

Learn more here.

July 30, 2026 2 min read

PRESENTED IN COLLABORATION WITH

Calling all micro-fiction storytellers! 🏁

For the second year in a row, Freewrite is teaming up with Grant Faulkner, co-founder of the Flash Fiction Institute and author of The Art of Brevity, to bring you the fastest, most adrenaline-pumping writing event of the year.

Whether you're a seasoned writer or a creative rookie, the Freewrite 500 is your chance to rev up your imagination, write a 500-word story, and win big.

You do not need to own a Freewrite to participate.

[REGISTRATION CLOSED]

 

How It Works

🎟️ Fill out the form above to secure your spot. It's totally free. (You must register to participate.)

📖 Watch the free mini flash fiction lesson by Grant Faulkner, which includes the announcement of the prompt for the contest. WATCH IT HERE.

📝 You'll have the weekend to finish and submit your 500-word storybased on the prompt by end of day on Monday, August 17. Entries must be 500 words or less. The entry form is plain text. Any necessary formatting should be noted in [brackets]. [SUBMISSIONS CLOSED]

✏️ Our judging panel, led by Faulkner and made up of writers from the Freewrite team and the Flash Fiction Institute, will judge each piece based on: length (500 words), relevance to the prompt, and creativity.

🥇 NEW THIS YEAR: The panel will select three finalists, and then announce one grand prize winner.

All work must be submitted by 11:59 p.m. ET on Monday, August 17, 2026.

The Prize Pack

One winner will receive:

  • Publication on the Freewrite blog and Flash Fiction Institute blog
  • 1 Freewrite Traveler
  • 1 hour-long one-on-one coaching session with Grant Faulkner
  • 1 free Flash Gym session with the Flash Fiction Institute
  • 1 Words Are Hard prompt deck
  • A paperback copy of Set Your Story Free, the ultimate guide to freewriting
  • A digital copy of the opening chapter of Grant Faulkner's book, The Art of Brevity

Second and third place writers will each receive:

  • Publication on the Freewrite blog and Flash Fiction Institute blog
  • 1 Freewrite Alpha
  • 1 free Flash Gym session with the Flash Fiction Institute
  • Words Are Hard prompt deck
  • A paperback copy of Set Your Story Free, the ultimate guide to freewriting
  • A digital copy of the opening chapter of Grant Faulkner's book, The Art of Brevity

The Schedule

  • Thursday, Aug 13: Lesson & prompt announcement
  • Monday, Aug 17: Submissions deadline
  • Monday, Aug 31: Finalists announced
  • Monday, September 7: Grand prize winner announced

Questions? You can reach us at hello@getfreewrite.com.

Write on.

The Freewrite 500 Pit Crew 🏁 

Full contest terms and conditions