What I Learned From My 100 Day Flash Challenge

Lessons learned, my process, my 24 Favorites, and more.

Photo by Dan Counsell on UNSPLASH.


From March 18 — June 26, 2021, I began and completed my first ever 100-day flash fiction challenge. The goal I’d set for myself is self-explanatory. For one hundred days straight, I would write, edit, and publish a flash fiction story, more or less, every 24 hours. It was a wonderful and transformative challenge.

The goal wasn’t always, I soon learned, to increase quality. Instead, the challenge felt mainly like running wind sprints, something designed to increase speed and, as a consequence, confidence.

I think my quality improved at points during the challenge, but more than anything, I felt more confident in my ability to turn out a viable story quickly.


Starting Point

Early in the challenge, my efforts produced mechanical, clunky stories with very little finesse. (But, again, a challenge such as this might not be the best pathway to increasing the more nuanced aspects of writing like style, finesse, etc. Maybe my second challenge will prove that idea wrong. We shall see.)

My grammar was, I’m embarrassed to say, quite awful.

I knew one needed to include images in their stories, but I only relied upon GOOGLE and hoped that the ones I chose weren’t copyrighted. (A hope and a prayer are not the most advisable way to proceed with either grammar or images.)


On Expectations

Early in the challenge, I believed that the quality of my stories would monotonically increase throughout the one hundred days. But by the time my days numbered in the seventies, I knew this challenge was more like a marathon than some steady path of improvement. I have never run a marathon, but I’ve heard the last miles are the hardest and the ugliest. That was the way of it for me with this undertaking.

But a challenge like this isn’t necessarily for improving story quality. I feel it is more an approach for boosting speed, confidence, and fine-tuning one’s method of writing.

Every day, I aimed to write, edit, and publish a story. That’s a lot of writing but precious little rewriting. Editing for me was to reread the story (after a few hours if possible — some days it was not), run it through my new best writing tool that is the Grammarly checker, and tighten up the story where I could.

A better approach may have been to write a draft in the morning, fix the grammar errors, then put it down until the end of the day and only publish after the story has had time to marinate a bit on the page and in my mind. But I was so focused on not missing a day that I felt compelled to have the thing done early in the day before I went to work before I walked, and usually, before I even had breakfast.




1. Prompts, Grammarly, and UNSPLASH Made Me a Much Better Writer

I have found that if I have an idea, especially if it sparks my imagination, kickstarts my creativity — I can write a story. But sometimes finding a plot can be problematic. Sometimes I have the opposite problem — I will have too many ideas and cannot choose one.

That is the beauty of writing prompts. Once I discovered there were such things and found several websites that host a bunch, the pressures of completing a story every day were reduced.

Here are several of my favorite writing prompt sites.




Every morning during my challenge after coffee, I would scan through my lists of writing prompts, I would pick one, and I would start. It is just that Nike slogan simple. Not easy, but simple. Out of the 100 stories I produced, I used writing prompts for half. The other 50 came from my imagination, which I feel has ironically grown stronger through using prompts.

My grammar used to be horrible. It’s still far from perfect, but these days there’s an 80% chance that my commas and semicolons are correct. I split far fewer infinitives. But I learned these things through using Grammarly in my stories. It has helped raise my writing to another level.

Early in my writing, a few weeks before I began this challenge, I entered a competition on VOCAL.media. This story was my entry, Skinny Mole Enterprises (LINK). The grand prize was $20,000, and I liked my story and my chances. But at that time, I still hadn’t started using grammar checkers. I was sure I would win something; there was a deep list of prizes; it was a clinch.

I either overestimated the brilliance of my story, or the contest judges run everything through a grammar checker before bothering to read them. Or both things happened. It’s a good practice, and I learned a valuable lesson.

When you publish on WordPress, MEDIUM, or VOCAL, images are necessary to attract readers; they’re the covers designed to lure your readers. Initially, I was only using GOOGLE to try to find and download images. That is amateurish and is likely illegal. UNSPLASH helps with its vast library of terrific pictures.

I’ve thought that it might make a good source of inspiration also. My usual practice is to hunt around for an image after my story is complete. But what if I scrolled through the catalogs of photographs until I found one that caught my eye, triggered my imagination? I daresay that would be the equivalent of a visual writing prompt.


2. Exclamation Points!!!!

Another bad habit I had when I started writing in February was using an absurd number of exclamation points peppered throughout my dialog and sometimes in my exposition!!!! I want to blame social media and Facebook, so I will.

A well-read friend pointed this out to me. I feel like it’s like pointing out an open fly at a cocktail party. I’m grateful that he shared this advice with me. I read somewhere that novelists like Hemingway and others would use only 2–3 for an entire novel. Some of my short stories (and I’m not exaggerating) had between 50 and 75.

Thanks, Stephen.



My routine was every morning to wake early, brew a pot of coffee, and begin writing. I might have pre-selected the story. More often, I had no idea what I was going to write that morning.

I would move to my bed, with its vast array of pillows and my Chromebook; I would make myself comfortable and begin.

First, if I hadn’t already selected a story to write, I would pick one from my files of writing prompts (my paranoia convinced me to download all the writing prompts I found online), then I would start.

When I first began publishing stories on WordPress & MEDIUM in February, I planned to do a story per day. I hadn’t declared it to be a definite thing, with a precise duration. Also, I was writing short stories every day. Some of them would be 6–16 pages long. Those stories would sometimes take several hours to write. Flash stories are generally 2–4 pages maximum. So they would be the work of one to three hours.

After my draft was complete, I would copy it to the cloud. Then I would take a break, stretch my back, go for a walk, have some breakfast, etc.

I saw early in the challenge that inserting a space between writing and editing was beneficial, but I didn’t always do so. I felt compelled to get the story done, finished, edited, and published as early in the day as possible. I feared the scenario of having to return home from work in the evening and upload it with only a few hours left in the day.

My first step in the editing process was to reread it slowly to make minor revisions and fix the grammar errors I was teaching myself to see.

Then I would copy it into a Grammarly window and hold my breath as it quickly checked my story. My initial scores were in the 70’s. They began to rise, and soon I regularly saw scores in the 80’s. Now, however, there’s only one score I will accept before stopping my edit cycles — if it doesn’t say 99, then I haven’t finished editing.

Then after another break, a shower perhaps, I would read my story out loud. (I can’t emphasize enough how helpful this step is. I didn’t always take the time to do it, not for every story. But when I did, it invariably led me to wrinkle my nose in disgust at my repetitious use of sticky words or smile in appreciation at some happy accident with alliteration or pacing.

I’d jump on UNSPLASH, choose and download an image.

With all the elements in place, I would create the story on my WordPress page StoriesByShawn.com — an awkward, clunky, ancient layout scheme with tedious navigation controls that I desperately need to update to something better — seriously, it looks like a damn MySpace page.

Once it was on my WordPress site, I would then IMPORT it onto MEDIUM and publish it there.

Finally, I would create the story on VOCAL.media.

Occasionally I would post links to the story on my FACEBOOK page or on a few of the MEDIUM pages I follow on FACEBOOK — but I have mixed feelings about those.

That was it. That was my process for the 100 days of my challenge — simple, but not easy!


4. Editing and Writing Should Be TWO Separate Activities

Editing is an activity distinct from writing. Well, of course, it is, I hear you say. But that’s not my point. My point is you should not edit immediately after writing. You should wait for fresh eyes, give the story some time to steep, and move out of your consciousness for a few hours, at the very least.


5. Read Your Story Out Loud.

Here’s an easy hint to help you with your edit cycle. After you’ve spell-checked, grammar-checked, and tightened things to your liking, occasionally stop to read your story out loud. No, this wasn’t my idea. I believe I read it somewhere. I’m not claiming credit for ‘inventing’ the technique; I’m merely testifying that it works.

Reading your story aloud will show you clumsy passages, awkward language, and sticky words and phrases that you might not be aware of overusing. It can also highlight places where alliteration works nicely or would be a nice touch. Reading aloud shines a light on passages where your pacing is being unnecessarily restricted.

I read my stories out loud for myself or a friend of mine. When I do, I try to do it as if I were performing the story, as if I were reading it for a paying audience. If my writing is such that it allows me to do this with a tempo and sentences that vary enough to create some dynamic tension, then I feel its movement in the right direction.

Maybe some writers can spot the sticky elements without reading them aloud. At my present level of development, I cannot.


6. The Courage to Rewrite

I don’t know why I struggle with rewriting a story. Sometimes it’s the only way. Once you’ve wandered too far into the weeds, meandered too far from your original vision, your best bet is to start over. But it’s hard to do.

That is perhaps more of an issue for short stories than with flash fiction. With flash fiction, rewriting is easy. My works were all between 2 and 5 pages in length, maximum.

But with the pressures of putting out a new story every day, I didn’t have the time (or didn’t take the time) to rewrite it. I think I rewrote a couple of stories. When I embark upon my second flash challenge, I will make a conscientious choice to rewrite when necessary. Or I could insert it into my method.

1. Find an idea (or writing prompt) that speaks to me

2. Create a rough outline

3. Write the draft story

4. Edit the story (spell check, grammar check, etc.)

5. Start over and rewrite it from scratch.

A part of me likes this idea, while another part is laughing and swearing that it will never agree to such lunacy.



Strunk & White mention removing unnecessary words in their essential guide. Stephen King talks about it in his book On WRITING (which you should buy and read).

It’s surprising to me how much I can cut from a scene, and it still works. I’m probably over-telling, over-describing everything in my draft stage. I’m hoping as I mature as a writer, I don’t have to cut so much in the future. It’s hard to cut sentences you like. They may be impeccably constructed sentences, but they don’t work in the scene or the story. But there’s also something profoundly joyful about giddily slashing away redundant, superfluous, extra, additional, wordy, run-on, tedious, over-long passages.


8. White Space and Paragraph Length

Paragraph length, especially in flash fiction, should tend towards the shorter, in my opinion. Overall, I think most paragraphs should fall in the compact end of the spectrum. That helps your pacing. Maybe I’m wrong, but I don’t envision a languid flash fiction story. Even as I type that sentence, I have doubts about it. There are very few absolutes in writing.

White space around your paragraphs or even horizontal dividers can help segment and control the flow of how your story reads. That is purely subjective and stylistic.


9. You Don’t Always Need an Outline

For flash fiction, I think sometimes you can forego the outline. I did. Or perhaps I outlined the story internally? My story Zach is a 600-word story that I neither outlined nor planned. I had the premise of an idea of being infected with a parasite of bugs. Then the rather cheesy punchline (“Maybe it’s just a twenty-four-hour bug,” revealed itself as I was writing, and I knew I found my non-resolution resolution. The story is a joke, meant only to make the reader laugh. The story didn’t require an outline; it only required that I have a premise, trust the process, and begin.


10. Write it Down!

This one might be more of a reminder to myself. I’m having some minor issues with my memory (I hope they remain minor.)

But more than once, my fertile imagination has launched some workable ideas into my arena of consciousness. Some were good ideas that I was confident I would remember later. And several times, I forgot it promptly.

Now I carry blank index cards and a pen on my person at all times. Every work bag, book bag, computer case includes several blank index cards and a pen.

My muse doesn’t care to repeat her suggestions and the gracious thing to do, when she utters anything, is to write it down as soon as possible.


11. On Marathons and Not Giving Up

I haven’t always been the most disciplined person. So I was pleasantly surprised that when I undertook this challenge, I became very disciplined, structured, and focused upon not missing a single day during my challenge.

It wasn’t always easy.

When I started, I had two entire planned collections of short stories in draft format. I figured that some of these could provide a working buffer from which to pull works. I didn’t want to give away for free my best stories like Yellow HoodieBlue is the Bad ColorWell, and Werewolves Anonymous, but I could post some of them online and still include them in books that I had planned to write after I finished my challenge. The buffer worked okay for a few weeks, but soon I was basically out of pre-written stories that I was willing to give away.

That was why finding the many online resources for writing prompts helped take some pressure off of me.

A challenge of this length isn’t a sprint. This challenge was a marathon. There was some pressure to complete it, but I rose to the challenge. I’m happy that I started the challenge. I’m ecstatic that I finished it and have at least two dozen good stories to show for my efforts.




I’m going to discuss my favorite 24 stories that I produced out of the 100. It wasn’t easy for me to pick only 24. There are, in my opinion, at least 30 good ideas that I mined during this challenge. I will go back, tinker, and polish each one to see if I can extract the promise I believe lies within.

In my discussion, I may give away too much of the story. You’ve been warned. If you’ve not read it and you want to, use the links below to do so.



This story was the sixth in the challenge. I published it on March 23, 2021.

The writing prompt for this story came from Eadervell: with the tip of his paintbrush, he soaked up one of my tears.

This one is a tragic tale of two parents losing their daughter and trying to survive the loss by finding their way back to their unique rituals of loving each other. I like this story, though parts of it feel overwrought to me now. Perhaps that is a natural outcome of having matured as a writer. I know when I reread journals I wrote twenty or thirty years ago, I find myself cringing at the naivete of my earliest essays.

Deep grief, I think, is something from which you never recover. You learn to live with it. Or you don’t, but that would be tantamount to death, wouldn’t it?


In His Teacup

This one was the twelfth story and was published on March 29, 2021.

The writing prompt was: there was a ring in his teacup.

I liked the idea that everything can change in an instant. We have our plans. Then fate steps in, and we realize how foolish it is to think we have an abiding sense of control over anything.


Rooftop Ballet

Rooftop Ballet was the thirteenth story. The writing prompt was in the form of a list of items: ballet, rooftop, flashback.

I have not finished fussing over this story yet. I like it a lot. And I want to be sure I do right by it before I consider it finished.

Some of my best relationships have started as friendships.

I’m not a young man. I’m not quite old yet, but I’ve lived through a time of glorious social progress. I do my best to keep up. And anytime I’m talking to my black friends, my gay friends, or women friends, I fear I will say something outrageously offensive. Maybe the fact that I’m worried about offending means I’m conscious of the white man’s legacy of being offensive.

If you see offensive things here or anywhere in my writing, please tell me. I don’t want to be that clueless guy as I grow older.



This was the fourteenth story written in the challenge. The writing prompt was from my own imagination. It was probably something like ‘what happened if I opened this closet door and found it was truly, terrifyingly empty?’

It’s a horror story, The closet was in the bathroom of my friend’s guest room where I was staying during the pandemic. I found so much to inspire me in their lovely home and I will never be able to repay them for the many kindnesses they bestowed upon me as I recovered from covid-19.


White Snow/Red Kimono

The writing prompt for my twentieth story was: he lay back in the snow.

Another attempt at lovers parted too soon. I like the imagery and the music I hear when I read this story. It is another that I will want to pick at for too long. At some point, you have to step away from the story, wish it well. It is your child, but it is no longer yours, and you wish it well in the world.


Vaya Con Dios Maria

I was surprised at how popular my 22nd story became on VOCAL.media. It won $5 for a story-of-the-day honor. I do not believe it was close to being the best story I wrote during the challenge, but I like it. I am attracted to the plot of a character (a ghost) not knowing they are dead; I have written several versions of this story.

The writing prompt for this story was: she’d been coming here every day for four years, and there was never any work to do.

I was writing from a different perspective from anything in my lived experience.

It is not a perfect story. I think it is a tad predictable even. When I read it aloud to her, my friend guessed that Maria was a ghost. But I am attracted to this story because I have written several versions of the same underlying plot.


Monolith 2

I’ve written three stories about monoliths in this collection. The first one was Monolith; I hadn’t yet realized I was captivated by these oddities.

This story was the 24th story written and was published on April 11.

The only prompt I used for this was a nagging suspicion that writing the first story wasn’t enough to satisfy my strange hunger for these things. The first monolith story was all about tone. I was trying to recreate the mood these dreams had on me in my youth. But there was almost no action in the story. In this version, I wanted to create tone and atmosphere but have some action as well.


In the Woods

This story is the 30th in the collection. The writing prompt: you’re lost in the woods, and you don’t know how you got there.

It is the straightest, most unadulterated horror story I have ever written. The horror here isn’t couched in subtlety, nuance, or preening artifice. This story isn’t pretending to be anything other than what it is, a horrific, shimmering mess of entrails, atmosphere, and foreboding. It was fun to write; it is fun to read.



Retest was my 35th story. It was published on April 22, 2021.

The writing prompt was another enigmatic list of three disparate items: a plague, a piece of chalk, viridian.

I like this story, but I still wonder if there aren’t some clarity problems here. Several of my usual readers didn’t get that the retest meant killing the entire family. That was the purpose of the second set of swabs. I thought it was clear, but for some, it was not.



Nebraska was published on April 23, 2021, and was the 36th story.

I seem to gravitate towards and back towards the same several plots. This one is about a character not knowing whether he is dead or alive. But in this story, he at least asks the question, unlike Maria in Vaya Con Dios Maria and all the ghosts damned to relive the same day in Treatment Room 11.

The inspiration was inspired by my attempt at working in a retreat center back in 2012.


The White Elephant

My fortieth story, The White Elephant, was written from the prompt: write a story that contains only dialogue.

That suggestion made me think of Hills Like White Elephants.

No, I’m not comparing myself to Hemingway, at least not in any favorable manner. That is the goal, but I doubt I’ll ever get close to that with the late start I got with writing.

His story is better than mine. While I don’t feel that I achieved the objective suggested in the prompt, it was a worthwhile exercise. It is such a potent writing cue that I’m sure I will return to it again in the future.



Shrinking is a, I hope, charming and lighthearted love story. It was number 47 and was published on May 4, 2021. It was inspired by the prompt: you realize you are shrinking.



My fifty-fourth story is an ugly, brutal tale that scares the hell out of me. It was published on May 11, 2021, and I have no idea why anyone would want to read this. This story still freaks me out.

This one is all me.


The Elders; A Creation Myth of String and Feathers

This one is number fifty-five. The writing prompt I used was: invent a creation myth involving string and feathers. What an intriguing proposition. That is why I love writing prompts. I like to think I have a creative imagination, but I doubt I would have ever strung these words together on my own. They can provoke mad creativity, in my opinion, and I happily use them when I need them.


Treatment Room 11

I cried while writing this one. I usually cry when I reread it. Not because it’s powerful, but because I loosely based all the characters in this story on my real-life coworkers. I love the tragic damned ghosts stuck reliving the same day over and over. The structure reminded me of the movie 12 Monkeys. This one was the fifty-ninth story in the challenge.


Reynaldo the Rat

Reynaldo was the sixty-sixth story written during my challenge.

One day I woke up, and as I was looking at the carpet by my bed, the inspiration for this story landed in my head.

Let your imagination go where it will. Trust the process to unfold as it should. This one wasn’t a heavily outlined story. Basically, I started with the simple premise. What if I woke in my apartment to find a rat? Ugh! What if that rat had a human face? What if it spoke to me? Then I just started writing and let the two characters do what they wanted to do.


Midlife Mambo

I have stated elsewhere I’ve yet to settle upon a single vein of creative ideas to mine for the duration of my career as a writer. Midlife Mambo is from the opposite side of my creativity that gives birth to talking rats in hell. This story is about aging, love, hot air balloons, and accidental romance. I listen to David Byrnes ‘Make Believe Mambo’ on loop while writing this one. If you’ve not heard it, do yourself a favor and rectify that now. Don’t even finish reading this post. Seriously. You can thank me later.

The woman in this story was based upon a woman I once knew. Briefly. She was lovely and wild and crazy — all fun attributes for a fling, but, in my experience less-suited for something with a slower burn.



Rewind was the seventieth flash story written in my challenge. The inspiration came from thoughts about impermanence and aging as I walked to Fuzzy’s Tacos one hot afternoon.

The story structure felt like an allegory.

I love this story. I love the structure; I love the idea; I even sort of like the execution. I will polish it, and, I suspect, this one will shine. I think there are several truths here. You can’t relive the past, and even if you could, you couldn’t. It’s a cute idea, but thermodynamics and other things I might mention that would make me sound worldly and wise.


The Proxy

The Proxy was my eighty-sixth story. It was inspired by random anxious thoughts I have about my declining vision.

An author discovers he is going blind, then finds a partner to help him create his stories. I’m a sucker for romance and I feel like this is a nice story.


Zeke Vs Zombies

This was the eighty-eighth story in the challenge. The writing prompt: a group of friends takes on the zombie apocalypse. I published this one on June 14, 2021.

The issue I wrestled with most was the title. I wonder if I should have called it Zeke Vs The Real Zombies. Or does The Real give away too much of the game? I’m not breaking any new ground here with the ‘oh the humans were worse than the zombies’ stratagem here. It’s been done before, in 28 Days Later and in The Walking Dead.


Henry’s Heart

This story was the ninetieth story in the challenge. It’s my hamfisted version of The Christmas Carol.

The writing prompt was: a patient’s heart has stopped and they embark on a supernatural journey that leaves with a new outlook on life.

I like this story. It was fun to write, it is fun to read. It is part me, part Dickens. I look forward to revising it until it sparkles — which I think it will.



This funny story was the ninety-second story written during my challenge. Its inspiration came from some random thought I had one day.

A Flash story is to incite a mood or tone. This one is meant to incite laughter. It is basically a 600 plus word joke.


Mrs. Henderson

This was my ninety-seventh story written in the challenge. The writing prompt: the teacher is a monster, but no one will believe you. Of this challenge, I focused more on the teacher is a monster part. As soon as I read this suggestion, my mind went immediately went to my second-grade teacher. She was awful. This really happened to me. The humiliation I mean, I didn’t grow up to be a janitor or a monster slayer. At least not yet I haven’t.

I like that the villain is so arrogant, so inured to the fact that she is dangerous that she baits him openly.

What happens at the end? I don’t know, nor do I care. Flash fiction is all about evoking a mood or tone in my opinion and I think this story does that just fine, even without a clear resolution.


3:14 AM

This was the ninety-eighth story written for the challenge. I published this story on June 24, 2021.

One night I woke in the middle of the night, couldn’t fall back asleep so I decided to get up and write. I had no creamer for coffee so I walked to the corner convenience store. All as written in the story. But, as far as I know, I didn’t blackout and go on a murderous killing spree, but I do remember seeing a blue flashing light inside an SUV.

Of my twenty-four favorites, thirteen were inspired by writing prompts, eleven came from me.

There are a few other titles in my 100 that I feel might be coaxed into something a bit better. But even 24 out of 100 seems like a great success ratio. And these 24 I do believe have promise and a modicum of merit.

I like the cyclical nature of this aspect of my process.

I embark upon a challenge for X number of days. During that time, I create as many works as I can. Then afterward, I spend time revising and polishing each. I believe 24 flash stories would be enough to fill a small collection that is reasonably priced, or even free, on Amazon.




Making Time To Read and Connect With Other Writers

Now that my challenge has concluded, I’m catching up on my reading! I’ve missed reading these 100 days. On my nightstand, I currently have several short story collections by Hemingway, Munro, Saunders, Millhauser, Chekov, and Cheever. I am reading these regularly.

I’m also trying to be a more integrated, supportive author on MEDIUM. Read more, comment more, clap more, connect more. I think it’s important that we support our fellow writers.

Will I Ever Do Another Such Challenge?

Presently it’s not a question of if; it is a question of when. I would do another challenge. I think a future challenge would be for a less onerous duration. Perhaps just sixty or even thirty days sounds doable.

I might spend some time before the next one planning my approach. Maybe my stories will all fall in a similar genre? Or be connected thematically somehow? I like the idea of having a loose outline to help me navigate my way through the thing, maybe even having a summary or prompt of each story I plan to write. This may sound like cheating to you. That’s fine. Maybe it is, but I decide the parameters of my challenges.

VOCAL Media’s Ridiculous 600 Word Minimum Requirement

I enjoy writing and publishing on both MEDIUM and VOCAL. But the latter site has an absurd 600-word minimum length for stories. I find this to be ridiculously limiting.

Here is a six-word story that is generally attributed to Ernest Hemingway.

“For sale: baby shoes, never worn.”

It is 594 words too short to publish on VOCAL and yet it is (perhaps because it is so short) a very powerful story is it not?

The entire story is a six-word sentence and I cannot show you a single sentence of mine that packs such a wallop.

Making stories adhere to a minimum length is no guarantee of quality.

I’m happy I did the challenge and I would encourage anyone considering doing it to learn from my mistakes. Make friends with publications early, use grammar checkers and writing prompts. Have a plan. Good Luck!


  1. Whatever the outcome & however iffy the grammar, a 100-day flash challenge is one hell of an achievement. I can’t even maintain a diary into February. Thanks for sharing.


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