What I learned about writing novels by failing at short stories – and how to make a short story into a long one

Lee Martin wrote recently on his blog about how he hadn’t intended to write longform fiction. He started with short stories, and graduated to novels only when an editor suggested it.

I hadn’t thought about it before, but that was also my path. Though I was considerably less masterful at it than Lee, who had a respectable bank of published shorts by the time he began the big one.

I started small, and writerly friends urged me to think bigger, mainly because short stories were a much more difficult sell. At the time, I didn’t think I had a novel in me, though I dearly wanted to find one. And, being a beginner, I had my hands entirely full with the craft basics. I couldn’t control more characters, threads, etc etc.

I also wasn’t good at brevity. This was the first reason I was unsuccessful. Whenever I looked for competitions or magazines, I’d bust the word count by several thousand. Even with strict pruning, I couldn’t bring one in under 5,000 words.

And then there was another problem. I was Miss Misfit. I was complimented for style and originality, but literary folk said I was too fond of plot. It didn’t help that I used concepts from science fiction and suspense. Try genre magazines, they said. ‘Try literary magazines,’ said the genre mags.

Much as I yearned for someone, anywhere, to publish me, I’m glad nobody did because I now see a more fundamental problem, beyond the style and subject matter. Even if I didn’t think I could write a novel, my concepts needed a novel’s scope.

In my work as an editor, I’ve often seen how rushing a powerful idea can make it trivial. Usually it’s most apparent with individual scenes, especially emotional ones – a turning point might look unconvincing if it’s too brief, but becomes a spellbinding showstopper if the writer slows and takes their time over every moment. I think this may be why I never had success with short stories – I was rushing a bigger idea. Blurting it out in a state of panic instead of giving it the space and pace it deserved. So the result was underbaked for literary people, and ungraspably off-beam for genre people. In short, I was shortchanging an idea that needed to be bigger. That’s not to say a big idea can never be a brief story, but I wasn’t suited to that approach.

I’m thinking about this because of Lee Martin’s post and because I’m now putting one of those old stories on a bigger canvas. As you might already know if you saw this recent post about the wondrous paradoxes of a slow writing process, Ever Rest began as 7,000 words and has now grown to around 110,000. You’ll also see from that post that I began with trepidation. In my mind, Ever Rest was frozen in that small space. Was expanding it even possible?

I’m happy to report it was, so in case you’re also in an expanding frame of mind, here’s what I’ve been doing.

Is it still the same story?

Good question. It is because some parts of the core situation are technically the same, like the two Westworlds, Fargos, 2001s, Flowers For Algernons. And here I shall be magnificently vague as I’m not ready to explain more yet.

The how-to bit: making the story bigger

Find the other characters who have a story arc

My original story was a single viewpoint, first person. I looked for other souls who had a significant experience triggered by the core event. Gradually the cast list grew. The original character became two and they are now such distinct people that I can’t believe it wasn’t always thus. The story is now third person, six narrators.

Go beyond the original timescale

Ever Rest original had a timescale of a few days, with flashbacks to childhood and teen years. Gosh, didn’t I stuff a lot into 7,000 words? What if I spent longer in those years? I free-wrote in the characters’ viewpoints, not planning anything, shooting footage until they did something surprising or moving.

Look for missing moments

As I pieced my footage together, I found a pattern of situations that were always worth writing. When character A first met character B, what made them interested in each other? When character X started to change their mind about situation Y, what was that moment? Sometimes it was apparent that key conversations were missing. I didn’t know how those conversations would go; it was more that I knew the opposite – the characters would not be able to keep quiet.

Brief moments become major turning points

This is one of the joys of the bigger canvas. Moments that the original story glided through – or never even looked at – can become turning points, or even twists.

The end of exploration

Some of my explorations went to dead ends. I had plenty of footage that was ultimately dull, though nothing’s ever wasted. Even if a piece of text doesn’t stay in the manuscript, it helps with your own knowledge of the book. There were also plot directions that felt forced, so I took them out again. (Hint: keep all your versions so you can undo.)

The big question is this. With so many possibilities, how do you know when you’ve got an idea to keep? I always found the answer was this.

When it felt like it had been there all along.  

If you want to know more about Ever Rest, and anything else I’m working on, sign up for my newsletter!

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  1. #1 by Viv on April 29, 2018 - 7:03 pm

    I wrote a short story(called Someone’s Watching Me) that is in the collection “The Moth’s Kiss” and several folks remarked that they wanted to know more about the protagonist; I’ve sometimes wondered if there were a longer story there. I wish I had the energy to find out.
    I look forward to Ever Rest.

    • #2 by Roz Morris @Roz_Morris on April 29, 2018 - 9:49 pm

      Viv! Lovely to see you here, as always. It’s a double-edged thingy, isn’t it, when people hint they’d like you to revisit a story. Like when people ask for sequels to books you feel you’ve done with. You can’t force it, but maybe something will come to you that will start you off. Then energy won’t be a problem (I hope!)

  2. #3 by Teddi Deppner on April 29, 2018 - 9:45 pm

    It’s so encouraging to hear you describe your process, Roz. There are probably a lot of writers who don’t feel their writing (or process) fits into the molds so commonly described in writing circles. Hearing someone talk about trusting the process and trusting one’s intuition (even while improving one’s craft and training one’s instincts) gives us hope that something good can come of our efforts.

    I also love hearing about stories that start in one form and end up in another. It’s easy for us to stick a story in one box and forget that it might work just as well (or better!) in another one. Stories are far more malleable than we think!

    • #4 by Roz Morris @Roz_Morris on April 29, 2018 - 9:53 pm

      Hello Teddi! Process, instincts, intuition … it’s funny to see how they’ve become one organic approach over the years. Thanks for shedding this light on it!

  3. #5 by Robert M. Easterbrook on April 29, 2018 - 10:43 pm

    I was almost the opposite. I started out writing fiction by writing a novel – 120,000 plus words on my first attempt. It was a totally weird experience, but heady stuff. Mesmerising because my writing was powered by pure enthusiasm; didn’t think I’d succeed. My backstory is enlightening. I may have written a lengthy novel on my first attempt, writing Sci-fi/crime, but it was messy. I didn’t know; I was so ignorant of character arcs and story arcs. My style was flowery and bloated. I thought, at the time, I have a great idea, what if … And went with it. That was 4 years ago. I have since written 10 books, learning the craft as I go. Implementing what I learned as I have learned it. But even now, writing a short story is like a public speaking event: scares the hell out of me. I scorn restrictions on my writing; time limits, word limits. And I’m only now learning to see my writing from the perspective of the reader; a really difficult thing for me to learn. I have written only 2 short stories in 4 years, and both have failed to meet the expectations of competition organizes. The first, because I couldn’t meet the word limit no matter how hard I tried; the second, because it wasn’t clear what I was trying to say. This just made me frown. I was, oddly enough, comforted by the fact that no one has ever said I shouldn’t give up my day job. People have complimented me on my stories in terms of their originality and creativity. My only concern is finding an agent and a publisher; harder than writing a story.

    • #6 by Roz Morris @Roz_Morris on April 30, 2018 - 7:25 am

      I think some of us are just better suited to longform, Robert! And if novels are what you’re more interested in, continue with that. Thanks for stopping by!

  4. #7 by acflory on April 30, 2018 - 1:29 am

    Like you, I find short stories incredibly hard to write. I knew there was something I was missing, but I didn’t know what until I read a Hugo Award winning short story that seemed to explode in my mind. Being sci-fi probably helped, because I knew the tropes, but I suddenly saw that the key to short stories is to use the reader’s own imagination and acquired knowledge [esp. of the genre] to flesh out the breadcrumbs provided by the story. Easy to say, damn hard to do well. :/

    • #8 by Roz Morris @Roz_Morris on April 30, 2018 - 7:30 am

      Hi Andrea! That’s a nice point about leaving breadcrumbs for the reader’s own knowledge. And what an enormous amount of discipline that needs!

      • #9 by acflory on May 1, 2018 - 10:10 am

        Yeah…that the hard part. :p

  5. #10 by tracikenworth on April 30, 2018 - 1:41 am

    Just got another rejection today for a short story. I wonder too if I’m cut out for this style. I always like to expand things too. Mostly, I’ve been trying to do them because “they” say it’s a good field to conquer.

    • #11 by Roz Morris @Roz_Morris on April 30, 2018 - 7:48 am

      Hi Traci! I think it depends what you’re aiming for. I thought short stories would be a useful gateway. People would read them and eventually become interested in novels from me. Also, it would be easier to get my name circulated. But that’s probably the wrong reason – I think you’ve got to write them because they are what you want to write. They can’t be approached like a novel, the rules are different. And, obviously, nothing happens if you can’t get them published anyway!

      • #12 by tracikenworth on May 2, 2018 - 12:15 am

        The truth is I’ve been doing the same. I’ve read short stories are the way to break in but they don’t seem to be working that way for me. I don’t like writing condensed versions of stories I’d like to explore more.

  6. #13 by Don Massenzio on April 30, 2018 - 10:36 am

    Reblogged this on Custom Services for Indie Authors by an Indie Author and commented:
    Check out this post from the Nail you Novel blog on things you can learn about writing novels by failing at short stories and how to turn a short story into a long one.

  7. #16 by DRMarvello on April 30, 2018 - 1:01 pm

    I started with novels and now enjoy writing shorter forms occasionally. In fact, I’m writing a story now that will probably become my first novelette. Initially, short stories didn’t interest me because I knew marketing them was extremely difficult. Plus, the story ideas I wanted to pursue were novel-length because of the factors you mentioned: multiple invested characters, multiple points of view, and a plot that required many scenes to convey.

    It was social networking that got me interested in shorter works. As I made new writer friends and joined promotional networks, I started entering flash fiction competitions. Word counts were very low (200-1K, typically), which was extremely challenging. I discovered that writing to word count was a useful exercise. It taught me how to hone in on the essentials of the story while still giving the reader a beginning-middle-end reading experience. Best of all, it was fun. Later, I joined a writing group where our exercises could be of any length, so I used them to explore longer pieces that would qualify as short stories.

    A couple of years ago, I collected all of my short works into an anthology and published it. The first edition was mostly just a few flash pieces, so I offered it for free on my web site as a thank you to visitors. I added several short stories to the second edition, so I published that on Amazon and at other vendors. I’m still offering it as a “free taste” of my work. My plan is to release new editions of the anthology over time as I write more short works and add them to it. I may charge for it eventually, but for now, I’m happy enough using it as a promotional tool for my novels.

    • #17 by Roz Morris @Roz_Morris on April 30, 2018 - 6:20 pm

      Hi Daniel! Another longformer! I must admit I became more interested in shortform after writing Not Quite Lost – which I guess were true short stories. They made me think more about small scale, small shifts, limited stretches of time. Nothing ever got as short as a flash piece, though!
      I know a lot of writers use free short stories as samplers for their novels. Have you found this has worked? I’ve always thought that the readers of shorts aren’t the same group as the readers of longer fiction.

    • #18 by DRMarvello on April 30, 2018 - 11:49 pm

      Has offering free short stories as samplers worked? Overall, I don’t think so.

      The great majority of my sales come from Amazon, so there’s no way to know for sure. Although one could theoretically use an affiliate tracking code to get an idea, you never know what readers are truly buying. It might be one of your books or it might be a new toothbrush.

      However, looking at the also-bought titles for the anthology, I do see a theme. Almost every item is also a free book, so it’s clearly attracting freebie seekers more than anything. But that’s okay. A few dozen readers download the anthology every month, and I don’t believe it would sell at all If I were to put a price on it.

      If even one reader moves on to my novels as a result of reading the anthology, I’ll take it as a win. And if not, well, I hope they enjoyed the stories anyway.

      • #19 by Roz Morris @Roz_Morris on May 1, 2018 - 7:17 am

        Freebies attract freebie-seekers … that’s what I thought too, Daniel. I think it’s different for non-fiction, but then non-fiction is more like the world of web tools. Free WordPress users might upgrade if they see enough value in the premium version etc etc. But fiction doesn’t work like tools!

  8. #20 by Maria Donovan on April 30, 2018 - 1:58 pm

    I enjoy writing short stories and found the writing of my first novel slow going, even though I tried to hold myself to a timetable by writing in real time. I soon got behind and managed to keep track by keeping a diary for myself and the characters, while continuing to develop the various strands of the novel. Now I’m working on my second novel, I’m trying out a number of short stories for these new characters, finding out more about them as I go. It seems to be a useful way for me to experiment. I’m still not quite sure where that leaves the novel and I have about five half-finished stories on the go, but I’m definitely working out more and more about how they would behave and interact, what bothers them, their hinterland – and have found this useful for making early adjustments to the novel before everything gets too ‘fixed’. Loved your post, Roz!

    • #21 by Roz Morris @Roz_Morris on April 30, 2018 - 6:22 pm

      Hi Maria! Interesting! Do you think you might be heading for a connected set of short stories, like Olive Kitteridge? That’s a possibility!

      • #22 by Maria Donovan on May 1, 2018 - 1:48 pm

        Thanks, Roz. It is a possibility, indeed. Though an editor said to me she was wary of linked stories in case the author just couldn’t be bothered to turn them into ‘a proper novel’. I am wondering if I can achieve both in one book! It will be fun finding out.

        • #23 by Roz Morris @Roz_Morris on May 3, 2018 - 7:06 pm

          Walls have ears… I saw a discussion in a FB group about novels that are linked short stories. I’m pasting some of the titles here in case it’s helpful for you

          Julia Glass THREE JUNES
          Visit from the Goon Squad by Jennifer Egan.
          Alice Munro’s The Beggar Maid
          Sarah Shun-lien Bynum’s Ms. Hempel Chronicles.
          The Imperfectionists, by Tom Rachman
          God is Dead by Ron Currie Jr
          CLOUD ATLAS by David Mitchell and BLIND ASSASSIN by Margaret Atwood.
          Day for Night by Frederick Reiken
          Don’t Let Him Know by Sandip Roy
          Cynthia Ozick’s Puttermesser Papers
          Lore Segal’s Shakespeare’s Kitchen.
          Notes from Heaven by Jennifer Haigh
          Larry’s Party by Carol Shields

          • #24 by Maria Donovan on May 3, 2018 - 7:08 pm

            That is quite a list! Thanks very much Roz. Something to aspire to after all.

  9. #25 by dgkaye on May 1, 2018 - 12:22 am

    Thank you Roz, for sharing your own process. It can be quite a transition going from writing short stories to novels and vice versa. Thanks for enlightening us. 🙂

    • #26 by Roz Morris @Roz_Morris on May 1, 2018 - 7:15 am

      Hi Debby! Yes it is quite a transition. Perhaps I’ll have another go at the shorter version sometime…

  10. #27 by J. M. Galindo on May 2, 2018 - 11:48 am

    Well, that is a lesson. I am beginning to write short stories and even finished a book of them.

    I plan to write a long story but I have failed….because I felt the story didn’t have a reason to continue…..I will find the muse by writing more…thank you for this article…I will re-read it

    Ah…you are an amazing writer

  11. #29 by authorleannedyck on May 16, 2018 - 10:33 pm

    Though I have written novels, I’m more at home writing short stories. But your article has helped. Thank you, Roz.

    • #30 by Roz Morris @Roz_Morris on May 17, 2018 - 7:42 am

      Thanks for commenting, Leanne! Everyone’s comments here have illustrated how we all have our comfortable lengths – although as we gain experience we can stretch those limits if we feel inclined.

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