Category: creative writing

Organizing a Short Story Collection

These are short story collections.

Last year I made a plan. In 2020 I was going to build a website (check!), consistently update that website (mostly check!), and I was going to self-publish a novella and a short story collection (… not check…).

So obviously, 2020 being what it is, things have changed. When I made this plan there was no Covid on the horizon, I wasn’t thinking about buying a house, and I didn’t expect to become a father. Yet, somehow, all of those things happened. And you know what? I kinda like the unplanned stuff more (except Covid–that can suck a big fat donkey dick).

Anyway, all of those things are a delay, not a cancellation. The novella is written (but needs some editing, and a rewrite of at least one section), and I have enough stories to put together a collection. The plan was always to pull down the vignettes and collect them with unpublished stories. I’m going to do that, but as I sat to think about what that could look like I realized that short story collections are more complicated than just taking a bunch of stories and throwing them together.

First, if I’m going to self-publish something, even if it’s only priced for $0.99, I want the reader to get value out of it. A book made up of 12 vignettes would top out at 15,000 words, if that. I don’t think I’d buy that book, especially when the vignettes were already free online at some point. This wouldn’t be as simple as just collecting and self-publishing what is already on this site.

The idea was never to only do that, but I did want to ensure that I had enough stories of varying lengths to make a purchase worthwhile. I went through everything I’ve written, including what I knew I wanted to include, some works I wasn’t sure about, and ideas that aren’t written but I’m excited about. I put them all into a spreadsheet (youse know how much I love spreadsheets) and wrote down the exact page count for each, as well as whether the writing was a vignette, short story, or poem.

Seeing all the stories laid out quelled my fear that I wouldn’t have enough writing that I was proud enough to publish. I saw there was a decent mixture of lengths that, together, added up to something worth $0.99. The next step, then, was figuring out how to organize them.

I didn’t quickly find many articles online for organizing short story collections. That said, much of my thinking from here on out is influenced by this blog post from BOOKFOX, so instead of cribbing from it I’ll just point you there.

Specifically, I found guideline #3 to be helpful: “Build your own structure, and then order stories according to that logic.” The post describes five different types of structures for a collection–hourglass, möbius strip, mosaic, musical improvisation, and instant replay. The hourglass structure most appeals to me for this particular collection.

Having decided on a tentative structure (it may change as I work toward publication), I had to figure out how to fit the stories I chose into this concept. My stories tend to wander between genres, but touch on common themes or play with similar styles. I went back to my spreadsheet and added “Genre” and “Subgenre” columns. Sticking to only a few genres so as not to overcomplicate the exercise, I put the writings into loose groupings.

Then, on the advice to start with your strongest story to draw the reader in, I arranged the order from that story down. From there, I tweaked the order in which stories appeared to have a better flow from genre to genre, and from idea to idea. Now, the collections starts with a series of horror stories, eases into existential dread, turns into experimentalism, dovetails into romance and sci-fi (I tend to use sci-fi to explore romantic notions–who knew?), and ends on a dramatic note.

This collection has required far more thought than I expected, but it’s also challenged me to think deeply about what I’m including and why, and illuminated common themes in my work.

I hope to have the collection on Amazon by December or January.

Proposal Writing vs. Creative Writing

I haven’t written a word of a new (or old) story in over a month. That doesn’t mean I haven’t been writing.

On June 16th I had my orientation for my new position, Proposal Writer and Analyst. What exactly does a Proposal Writer and Analyst do, you ask? I write proposals and analyze… uh… stuff. Duh.

In short, it’s a marketing position. Proposals are marketing materials, designed to explain how the company I work for, TCG, can help the government solve whatever problem they have. We’re an IT company, primarily, so the problems we’re trying to solve are mostly to do with technology. Sounds pretty fancy, right? You can probably imagine me working with emerging technologies the public don’t even know about, learning their specifications so I can write amazing prose that convinces the government to give TCG millions upon millions of dollars so we can push forward their technological superiority.

You would be wrong.

The truth is much more boring. While there are some amazing technologies used within government (and probably more amazing technologies I’m not privy to, not owning a clearance), most of it is pretty mundane. They use Windows as an operating system and, in most cases, Internet Explorer as a browser. Most of the time, their technologies aren’t even as advanced as the ones we use publicly or in the corporate room. This is for a lot of practical, financial, and security reasons.

Anyway, writing proposals (or white papers or capabilities statements or responding to Requests for Information) is a lot different than creative writing. For one, you’re more or less confined to a little box. Creative writers hate that (although others construct their own to maximize their perceived creativity), but with the government it’s a fact that you just have to accept. Because every government agency is different, and they have different needs/baseline technological environments, their requirements are different. This makes each solicitation different, which makes each response different.

But because of the limitations each agency faces, and because the government likes to erect walls you have to scale so they can weed out the ones not willing to do so, a proposal writer faces a lot of limitations. Page count limits, only being able to use certain fonts, following a specific structure – it all serves as a way for the government to fairly and quickly assess your qualifications but man oh man does it suck the creativity out of writing.

Or does it? (Yes, kind of)

See, just like those writers who create arbitrary rules for themselves to follow in order to force themselves to be creative, within the box the government puts you in there are ways to spice it up. It all depends on your approach.

Most companies take a by-the-books, dry, technical approach. That may be the best approach, honestly. It’s (mostly) clear, the evaluation criteria are easily met, and there is no room for interpretation.

What I’ve done in the past, and a few of my proposal writing friends sometimes do, it inject storytelling and emotional weight to their writing. It’s not an easy thing to do (and often takes much more work than “answering the mail”) but it makes the writing pop and feels more worthwhile. Here is where proposal writing and creative writing intersect – being able to find that emotional weight that connects with people and makes them want to keep reading.

Basically, believe it or not, people in the government have important jobs. Government contractors, those who try to improve the government by bringing in methods and strategies from the private sector (which tends to be more progressive and less risk-averse), and whose jobs depend on my being good at selling solutions to the government, are important. What many companies fail to do, and what makes their writing so damned boring, is tap into what makes these jobs important. Why is it important that the Library of Congress have excellent network security? Why is it important that the Department of Education has a standardized system for doling out grants? That’s where the creativity and emotion comes in.

On a more technical level, proposal writing and the limitations it comes with calls for a more concise style of prose. You don’t want to waste words. Sometimes this can lead to poor writing; things are condensed to the point where they’re barely sentences anymore. Other times it leads to writing that’s compelling and tightly paced. It’s not an easy thing to pack as much information in as few words as possible. I would say 90% of writers fail.

I haven’t mastered it. I may never master it. I’m not even sure if I like proposal writing, yet. But it has helped me to tighten my writing and I think it’s given me a screenwriting advantage, as screenplays are also short on real estate.

For someone that wants to write for a career there aren’t many options. I stumbled into proposal writing mistakenly thinking that putting pen to paper is the same wherever you are. I was wrong. It’s hard and it’s draining and it’s different than creative writing. But the experience has still helped me to grow. It’s taught me to honor deadlines regardless of anything. It’s taught me to write concisely. And it’s taught me 1,000 new ways to fail.

Still, if I ever make it as a creative writer it will be because of this detour. And if I fail as a creative writer, I could be on worse career paths.

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