Have you ever stared at your screen and wondered if your writing could actually pay off—literally? That thought crosses the minds of more writers than you might think. I remember sitting at my desk with a half-finished story, thinking, “Is this just a hobby, or can this actually go somewhere?”
For a long time, I thought writing contests were only for people with literary agents or shiny MFA degrees, the kind of folks who casually reference Hemingway over coffee. Turns out, I was dead wrong—and honestly, I wish I had known sooner.
There’s an entire world of free writing contests out there, offering real cash prizes—sometimes hundreds, even thousands of dollars—just for a short story, a single poem, or a powerful essay. No entry fees. No hoops to jump through. Just your words versus the world.
And the crazy part? These contests aren’t just about the money (though, let’s be real, getting paid for your passion feels pretty amazing). Winning can open doors you didn’t even know existed—like getting published in respected journals, attracting the attention of editors, or even landing a book deal.
The trick is knowing where to look, how to pick the right contests, and how to make your submission stand out.
This guide will walk you through how to join these contests the smart way, give you real examples that pay, and show you how to improve your chances of winning, without burning out or second-guessing your talent.
If you’ve ever thought, “What if I just went for it?”—this is your sign.
Why You Should Join Free Writing Contests
Let’s clear something up first. Free writing contests aren’t just about chasing prize money (though I won’t lie, getting paid to write feels amazing). The real value goes much deeper.
These contests are one of the few places where writers of all backgrounds—whether you’ve published a novel or only scribbled in the Notes app—are judged solely on their words, not their resumes.
Here’s what makes them worth your time:
They help you build your credibility. When you’re querying agents or applying for residencies, saying you were longlisted in the Bridport Prize or won second place in a reputable flash fiction contest can make your submission stand out. It’s proof that someone, somewhere, saw real potential in your work.
Judges aren’t hunting for robots with perfect grammar. They’re hoping to feel something human.
They also push your writing to the next level. Deadlines have this strange magic. Suddenly, all that procrastination turns into productivity. I’ve written some of my tightest, most polished pieces thanks to submission clocks ticking down.
Contests also get your name in front of people who matter. Many of them are judged by editors, publishers, or authors with serious industry clout.
Even if you don’t win, your piece could still land in the right inbox. I once received an email from a literary journal asking to publish my entry, even though I didn’t win. That kind of thing sticks with you.
There’s also the chance to gain exposure. Some contests publish winning or shortlisted entries in magazines, anthologies, or online platforms.
That’s how a friend of mine, who’d never published before, ended up with her essay going semi-viral after being featured in a literary site’s contest winners list. Suddenly, her inbox was full of interview requests.
And yes, let’s talk about the money. Some contests offer $500, $1,000, or even $5,000 prizes. The Whiting Foundation offers up to $40,000 for nonfiction. These aren’t just token prizes—they’re career-boosting.
Here’s a juicy stat for you: According to WinningWriters.com, more than $250,000 is awarded each year across free writing competitions. That doesn’t even include local, university-sponsored, or niche contests. That’s a lot of zeroes—just waiting for someone brave enough to click “submit.”
If you’ve ever told yourself, “I’ll enter when I’m better,” I’ll say what I wish someone told me earlier: you get better by entering. The growth, the feedback, the thrill of taking a chance. It all adds up. Every contest is a stepping stone, not a finish line.
Where to Find Free Contests That Actually Pay
Google “free writing contests” and you’ll be buried under a landslide of questionable listings, shady prize promises, and vague sites that feel like they haven’t been updated since 2006. I’ve been there.
I once submitted to a “global writing contest” that promised $1,000 to the winner… and then ghosted everyone who entered. Never again.
That’s why I started bookmarking only the platforms that consistently deliver—places that don’t just throw any contest on their site but actually vet them for legitimacy, payout, and exposure. These are the ones I trust because they’ve never let me down:
- Poets & Writers – Think of this as the New York Times of literary opportunities. Their contest listings are curated, detailed, and often come with notes like “no entry fee” or “judged by award-winning author.” If it’s listed here, it’s legit.
- Reedsy – Their contest calendar is a hidden gem. You can filter by genre, deadline, entry fee (or lack thereof), and even prize amount. What I love most? Their layout makes it easy to find smaller niche contests you’d otherwise miss.
- Winning Writers – These folks really care about writers. They only list contests that are free or reasonably priced, and they clearly flag any potential red flags. They even give out awards to the best contest hosts annually. Yes, that’s a thing.
- Submittable – You may already use this to submit work to magazines or journals, but did you know they have an entire “Opportunities” section? It’s a goldmine for open calls and contests, and many are free to enter and pay actual money.
- The Write Life – Every few months, they publish a beautifully organized roundup of the top writing contests for that season. It’s perfect if you’re too busy to dig through listings yourself.
And don’t underestimate the power of social media. If you’re on Twitter (or X), keep tabs on hashtags like #WritingContests, #AmWriting, and #WritingCommunity.
That’s how I found a flash fiction contest last year that paid $500 and was only open for 72 hours. It didn’t make the rounds on the major sites, but a fellow writer tagged me, and I made the shortlist.
The lesson? Great contests are out there. But like thrift shopping or garage sales, the good stuff doesn’t always scream for attention. Sometimes, you’ve got to know where to look or know someone who does.
How to Choose the Right Contest
Let me tell you—when I first started submitting to writing contests, I jumped into anything that had the words “free” and “prize” in the title. Big mistake. I wasted time (and a few great pieces) by entering contests that either didn’t fit my writing style or had fine print that worked against me. Some were genre-exclusive.
Some were looking for voices from a particular region or background. And some, well… they weren’t exactly clear about who owned the rights after submission.
That’s when I realized: not all writing contests are created equal. Choosing the right one isn’t just about finding something that sounds exciting—it’s about making sure it matches who you are as a writer, where you are in your journey, and what kind of exposure or prize you’re looking for.
Think of it like dating. Just because someone looks good on paper doesn’t mean they’re your perfect match.
Here are some things to always check before you submit:
- Are they looking for poetry, fiction, nonfiction, or hybrid work? Don’t waste your best horror short story on a contest that only accepts memoirs.
- Do they have a theme or prompt? One contest I entered wanted stories inspired by dreams. I submitted something about insomnia and regret—close, but not quite what they wanted. That lesson cost me a spot on the shortlist.
- What’s the word count limit? If your story is 4,000 words but the limit is 1,500, trimming it might hurt the heart of the piece.
- Who are the judges? If the judges are poets who lean toward experimental styles, a traditional narrative might not resonate as well. Some contests even list the past works of the judges, and reading their style can give you a serious edge.
- Do they ask for exclusive submission rights, or will you retain ownership? Some contests are sneaky about this. You always want to know whether you’re allowed to republish the piece elsewhere, especially if it doesn’t win.
Quick tip: If previous winners are published on the contest website, read them. Really read them. Look at the pacing, tone, structure, and subject matter. It gives you a blueprint for what that contest values.
Honestly, that alone has helped me get shortlisted more times than I can count.
Choosing the right contest isn’t about playing the odds—it’s about playing smart.
How to Submit Like a Pro
Here’s something most people won’t tell you: judges don’t always read every entry from start to finish—especially if they’re skimming through hundreds in one sitting.
Sometimes your submission doesn’t even make it past the first screen—and not because your story was bad, but because you didn’t follow the rules. It’s like showing up to a black-tie dinner in flip-flops. You might have the best personality in the room, but nobody’s going to invite you to speak.
I learned this the hard way. I spent two weeks crafting a personal essay I was sure would win. It had heart, tension, humor—the works. But I overlooked one tiny detail in the guidelines: they only accepted PDFs. I submitted a .docx. Boom—disqualified. No warning, no do-over. Just silence.
So don’t wait until your imposter syndrome says you’re ready. Don’t wait for someone to officially dub you a ‘real’ writer. Pick a contest. Write something honest. Hit submit.
Since then, I’ve treated every contest submission like a job application. Because that’s what it is, really. You’re asking someone to take your work seriously, so you have to treat it seriously, too. And the smallest slip-up can get you booted out before your words ever reach the decision-maker.
So, before you hit that beautiful “submit” button, slow down. Breathe. Double-check everything. Here’s how you do it right:
- Read the guidelines twice. Once to get the general idea, and once more right before you finalize your file. Trust me, it’s easy to miss a formatting rule or a “no cover letter” note buried near the bottom.
- Polish like a professional. This isn’t your journal entry or a cute Instagram caption. Edit ruthlessly. Every sentence should earn its place. Read it out loud. Better yet, get someone else to read it out loud to you.
- Stick to the theme. Even if your story is brilliant, it won’t win a “climate change” contest if it’s about a guy who just really likes cheese. Stay focused.
- Grab attention early. The first paragraph is your handshake, your elevator pitch, your Netflix trailer. It needs to stop a busy, possibly grumpy judge in their tracks.
- Respect the deadline. I’ve seen writers hit submit with just minutes to spare, only for their browser to freeze or the submission portal to crash. Don’t risk losing weeks of work over a technical hiccup.
Remember, the goal isn’t just to enter the contest. It’s to give your writing the best possible shot. That means playing by the rules—and then standing out once you’re in the door.
What Judges Are Actually Looking For
Let me tell you a little secret that I wish someone had told me earlier: most writing contest judges aren’t scanning for the next Shakespeare. They’re not out to find the most polished, flawless manuscript on Earth.
What they are looking for is something that feels real—something that moves them, even if it stumbles a little along the way.
The truth is, I’ve read contest-winning pieces that had a typo or two. And you know what? I didn’t care—because the voice was electric. The emotion felt like a punch to the chest. It made me forget I was reading. That’s the kind of magic judges want to find.
When I started entering contests, I spent way too much time obsessing over every little comma. I rewrote my stories so many times that the heart of them got lost in the edit. Then I read this quote by Anne Lamott: “Perfectionism is the voice of the oppressor.”
It hit me hard. I realized that trying to be perfect was just another way of protecting myself from rejection. I wasn’t aiming for excellence—I was just afraid.
So, what do judges actually want? Think of it like this: they’re looking for stories or poems that crack open something inside them. They want:
- A fresh perspective – Say something in a way they haven’t heard before. Make them pause.
- Emotional impact – Whether it’s laughter, heartbreak, or a twist that leaves them speechless, make them feel something.
- An authentic voice – They want to hear you, not a watered-down version of who you think a “literary writer” should be.
- A clear, well-structured narrative – Even the wildest piece of experimental fiction needs a spine to stand up straight.
- Respect for the reader’s time – Clean grammar and formatting may not win you the prize, but sloppy work can absolutely lose it.
Think of your submission like walking into a room full of strangers and telling them a story they didn’t know they needed to hear. The ones that resonate—that linger in someone’s chest after they’ve finished reading—those are the ones that win.
So don’t let the fear of imperfection stop you. Judges aren’t hunting for robots with perfect grammar—they’re hoping to feel something human.
And that? That’s where you shine.
How to Boost Your Odds of Winning
Winning a writing contest isn’t always about being the best writer in the room. It’s more often about being the most prepared, the most strategic, and the most willing to treat your entry like it matters.
Talent is part of the equation, sure. But the truth is, even the most brilliant story can get overlooked if it’s submitted sloppily or to the wrong contest.
I learned that the hard way.
When I first started entering contests, I treated them like scratch-off tickets. I’d send the same story to five different places with zero adjustments, no real research, and a quiet hope that someone, somewhere, would just “get” me. Unsurprisingly, I heard nothing. Radio silence.
But things changed when I stopped winging it and started treating each contest like a job application. I began to research the judges, read the past winners like they were cheat codes, and tweak my entries to better fit the tone or theme of each contest.
I even started writing short, genuine cover letters instead of the copy-paste stuff I used before. It wasn’t long before I started making shortlists—and eventually, my first win.
Here’s what actually helped me improve my odds:
- I reused polished pieces for multiple contests—but only when it was allowed, and only when the piece actually fit the contest’s vibe. I learned that one story can live many lives, but it needs to dress for the occasion.
- I studied winning entries like a writing coach would. I broke them down: How did they open? What emotions did they evoke? What risks did they take?
- I started sharing my work with a small circle of honest, thoughtful readers—people who weren’t afraid to say, “Hey, this part drags,” or “You lost me here.”
- I submitted early. Not just to avoid technical glitches, but because I’ve read that some contests read entries on a rolling basis—meaning the fresher ones don’t always get the freshest attention.
There’s something empowering about knowing you did everything you could to give your work the best chance. It shifts your mindset from “please pick me” to “this is something worth reading.” And that confidence? It shows.
What Happens If You Win—or Don’t
Winning a contest can change everything—seriously. Beyond the prize money, which is always nice, the ripple effects can be huge. You might get published in a respected journal. Your name could land on the radar of a literary agent or editor.
Sometimes, it’s just a quiet, internal shift—the confidence boost that says, Hey, maybe I’m not just playing around here. Maybe I’m actually good at this.
I still remember the moment I opened the email that said I’d won my first microfiction contest. It wasn’t a huge prize—$150 and a short feature in a small indie magazine. But my heart raced like I’d just signed a six-figure book deal.
If you’ve ever told yourself, ‘I’ll enter when I’m better,’ I’ll say what I wish someone told me earlier: you get better by entering.
It wasn’t about the money. It was about validation. Someone out there, a total stranger with nothing to gain, thought my words were worth something. I felt like I’d stepped into a new version of myself—someone who didn’t just write, but was a writer.
But here’s the real talk: most of the time, you won’t win. You’ll submit something you poured your heart into, and it’ll vanish into the digital void without a word. That doesn’t mean you’re not talented. It doesn’t mean your writing didn’t land with someone—it just didn’t land with that judge, that time.
Judges have preferences, moods, biases. Maybe your story reminded them of something personal in a good way. Maybe it didn’t. Maybe they just had three other pieces that hit a bit harder that day. It’s a subjective process, and it’s not always fair.
Stephen King famously pinned his rejection slips to the wall with a nail until they got so heavy, he had to switch to a spike. J.K. Rowling was rejected by a dozen publishers before Harry Potter found a home. The point is, even the greats got passed over—a lot—before someone said yes.
So if you don’t win, don’t fold. Don’t self-reject. Revise if you need to. Send it to another contest. Or not. Just keep writing. Because every contest you enter sharpens your voice, your discipline, your grit—and those things matter way more in the long run than any prize.
Free writing contests with cash prizes are one of the best-kept secrets in the literary world. They’re not just for the MFA crowd or the folks who spend their afternoons in indie coffee shops quoting Rilke.
They’re for you—the working mom scribbling poems between diaper changes, the college student jotting stories between classes, the barista writing dialogue on napkins, the 9-to-5 employee editing their flash fiction in a Google Doc while pretending it’s a report.
I’ve been there too. I remember entering my first contest with a weird cocktail of excitement and dread. I had no formal training, no publications, just a story I couldn’t stop thinking about. I submitted it at 11:47 p.m.—minutes before the deadline.
I didn’t win, but the feedback I received? It gave me the kind of motivation that coffee and compliments alone couldn’t supply. That’s when I realized: you don’t need permission to be a writer.
You don’t need an agent. You don’t need a degree. You don’t even need the “perfect” story. You just need the guts to put your work out there. That’s it. That one brave click of the “submit” button is more than a submission—it’s a statement. It says, “My voice matters. My words deserve space.”
And guess what? Even if you don’t win, you walk away with something. Confidence. Clarity. And maybe, a stronger version of your piece ready for the next contest.
So don’t wait until your imposter syndrome says you’re ready. Don’t wait for someone to officially dub you a “real” writer. Pick a contest. Write something honest. Hit submit.
And if it helps, remember—I’m right here with you, cheering you on.
