Speculation, Inquiry, and a Quest for Purpose

Writing and Reflecting in Obsidian — Fiction Planning and Incubation


This is part 4 of a series about how I write and reflect using Obsidian, an extensible digital note-taking interface with some surprising and unexpectedly useful features. This post reviews my workflow for collecting and acting upon story ideas, turning premises into polished prose. I’ve been using Obsidian since 2021-02-06, and it has completely revolutionized my writing process. New posts every Wednesday until the series is complete.

Where do I put my ideas?

You know how it goes. You have a “story ideas” journal, or you’re like me and you write everything down in the same Leuchtturm 1917 notebook, but all that seems to be good for is accumulating things you may not ever come back to. I don’t have a good portion of my day to “sit down and come up with ideas,” I just write them down whenever I have them and hope for the best.

Digital note-taking tools promised to help with this, but I ended up just dumping everything into an “story ideas” file that would grow increasingly larger, such that every time I looked at it, I was bored by the same first entries that appeared every time I opened it, and eventually became overwhelmed by the number of ideas I had to tackle. I needed a system that would allow me to seamless drop my ideas into it, trusting that they would resurface later when they felt exciting and fresh again.

Then, once I had an idea that I wanted to develop into a full-blown story, either a short story or a novel,I wanted it to be frictionless to apply some of my favorite story construction frameworks to them. As nice as it would be to have “Write the story” be a single action-item that I could put on my to-do list and then cross out, there’s actually quite a lot more to it than that, and I needed to be able to break the project down into its constituent tasks that I could then schedule out into the future to ensure I actually wrote the damned thing.

Fortunately, all of this is totally manageable within Obsidian, and it doesn’t even take a lot of plug-ins to make it work.

Incubating Premises

If I have an idea for a story (hereafter referred to as a “premise,” in keeping with John Truby’s Anatomy of Story,) which doesn’t happen terribly often, I write it down as soon as I can, so I can revisit it later and see if it holds any merit. When I’m at my desk, this might go into my Morning Pages or directly into my Daily Note. From there, I create a note dedicated to that singular premise, tag it with #fiction/premise to make sure I can find it again, and move the note into my 41 Premises folder.

As you can tell, this filing system gives me multiple ways of re-encountering that premise. I can click on the Tags pane (courtesy of the Tag Wrangler plug-in) to find all of my premises at once, using that #fiction/premise tag, or I can open my 41 Premises folder to see each individual note in a list. The Waypoint plug-in automatically maintains a linked index of the contents of my 41 Premises folder, and I can pull up a random line from that list using the Dice Roller plug-in.

dice: [[41 Premises]]\|listItem

What about when random is too random, and direct search is too predictable? I am a fickle human, and I want something that it’s completely arbitrary, but which I also don’t have to do a lot of work to seek out for myself. What I would want, ideally, is for ideas to resurface periodically, and give me the option to decide about how soon I want to encounter them again. Andy Matuschak has some thoughts on using spaced repetition for incrementally developing ideas based on the same principles a lot of flashcard software (like Anki) uses to adjust the interval for review based on the perceived difficulty of the item up for review.

In my case, I use the Spaced Repetition plug-in to cycle through my #fiction/premise-tagged notes. It shows me one note at a time at algorithmically-determined intervals, and I can mark each one as “fruitful,” “unfruitful,” or “skip,” (although the actual buttons aren’t named that way,) to determine how frequently they’ll reappear in my “ideas” queue.

Story Planning and Development

Like I said, it would be great if I could just put a task on my to-do list that said, “Write X story from Y premise,” but it’s always more complicated than that. As much fun as it is to write by the seat of my pants, I don’t have all the time in the world to come back around and do the editing needed to get whatever came out of my pants into a passable story configuration. I’d rather work out the logistics of my story beforehand, then draft it out step-by-step from Point A to Point B.

For this purpose, I have a worksheet template that auto-populates the different tasks for ideating and writing a story, following Truby’s Twenty-Two Step Story Structure:

- [ ] Write down [[#Story Events]] describing each with a single sentence. 🛫 <% tp.date.now("YYYY-MM-DD", 2) %>
- [ ] Put the [[#story events]] in a rough order. 🛫 <% tp.date.now("YYYY-MM-DD", 4) %>
- [ ] Decide the protagonist's [[20. Self-revelation|self-revelations]], psychological and moral. Add to [[#Self Revelation]]. 🛫 <% tp.date.now("YYYY-MM-DD", 6) %>
- [ ] Give the protagonist a psychological and a moral [[3. Weakness and Need (Opening)#Weakness|weakness]], and a psychological and moral [[3. Weakness and Need (Opening)#Need|need]]. Add to [[#Weakness]] and [[#Need]]. 🛫 <% tp.date.now("YYYY-MM-DD", 7) %>
- [ ] Identify the [[3. Weakness and Need (Opening)#Problem|problem]] or crisis faced by the protagonist. Add to [[#Problem]]. 🛫 <% tp.date.now("YYYY-MM-DD", 8) %>
- [ ] Give the protagonist a specific external [[5. Desire|desire]]. Add to [[#desire]]. 🛫 <% tp.date.now("YYYY-MM-DD", 11) %>
- [ ] Establish an [[7. Opponent andor mystery|antagonist]] who has the same goal as the protagonist and is exceptionally good at attacking the protagonist's [[#Weakness]]. Add to [[#Antagonist]]. 🛫 <% tp.date.now("YYYY-MM-DD", 13) %>
- [ ] Create a [[10. Plan|plan]] that requires the protagonist to take a number actions that require adjustment after the initial plan doesn't work. Add to [[#Plan]]. 🛫 <% tp.date.now("YYYY-MM-DD", 15) %>
- [ ] Visualize the literal or metaphorical [[19. Battle|battle]]. Add to [[#Battle]]. 🛫 <% tp.date.now("YYYY-MM-DD", 16) %>
- [ ] Establish the [[22. New equilibrium|new equilibrium]]. Add to [[#New Equilibrium]]. 🛫 <% tp.date.now("YYYY-MM-DD", 17) %>
- [ ] Study the story steps and identify (or provide, if missing) the corresponding [[#Story Steps]]. 🛫 <% tp.date.now("YYYY-MM-DD", 20) %>
- [ ] Draft the story, dedicating three to six pages per story step. 🛫 <% tp.date.now("YYYY-MM-DD", 22) %> 📅 <% tp.date.now("YYYY-MM-DD", 29) %>

This template presumes I’m going to start writing sometime in the next two days, and it expects me to take a month to get to actually get to the principal drafting stage. Your mileage may vary—I’m a stay-at-home dad and homemaker, so I can’t write nearly as much as I’d like to—but I’ve been able to follow this template at least twice to produce a couple halfway decent short stories.

You might be wondering about those little airplane (🛫) and calendar (📅) emoji. Well, those are in service of another plugin, the Tasks plugin, which can intelligently show or hide to-do items based on the date that appears after those emoji. If you remember how I set up my Daily Notes Page, my “Due Today” section is comprised of a Dataview table that shows me all my tasks with a due date earlier than tomorrow. This ensures both that none of the steps fall through the cracks and that I don’t get overwhelmed by seeing all of them at once. Believe me, it can be overhelming.

(of course, it looks a lot cleaner in “Reading” mode)

I realize that this can make the process of creating a story feel a bit mechanical, but the truth is, without a method, it’s easy to get lost in the emptiness of a blank page. Without sorting through some of the key elements of a story beforehand, it’s also easy to write pages and pages that you later have to cut because, well, they just weren’t serving the story. Better to identify what needs to go before you even write it, right?

Sample Story Structure

After completing the checklist—identifying the characters, their desires, the obstacles that will meet them along the way, etc.—I end up with a full picture of what the story is going to look like, and what scenes I now need to turn my attention toward drafting. The end result might look something like this story chart for a short I wrote called, “Chaz the Destroyer”:

“Chaz the Destroyer” Story Events

The specific story steps (and why some of them are bold, out of order, etc.) might not make much sense without reading The Anatomy of Story, but it serves its purpose here as a proof of concept. What started as a premise (A lawless person, returning home after an absence of several years to find no one recognizes him, fails in an attempt to steal a valuable heirloom and starts a new life with an assumed identity) now has seven distinct scenes I need to write to turn it into an actual story.

Generating Stories

Inboxes only work if you trust how they’re drained, and while spaced Repetition might help, I haven’t fully implemented it in my system yet. The architecture is there; I’ve got the plug-ins installed and configured the way I want them, it’s just different to put it into practice. For the time being, I’m still usually opening my Premises note manually, then picking one I think is ready to develop as a jumping off point. ^2d4aff

That being said, I was able to move at least two total writing projects from ideation to completed drafts (which I then sent to my critique group) within a month of their inception, and they each ended up about thirty pages long. The same principles can be applied to longer form fiction writing, which is something I’ll discuss in my next post.


Next week, I’ll discuss the missing link between having a story outline and actually getting the prose on the page. It’s simpler than you might think, but that’s not to say it’s easy. Writing is the easy part, it’s sitting down to write that’s hard.

About the author

Ian Hayes

Former technical support and customer service professional, now freelance writer and entrepreneur writing Horror, Narrative Nonfiction, and Literary/Speculative Fiction.

Also backpacker, rock climber, casual biker, woodworker and armchair philosopher.

Currently living in Portland, Oregon, but also from New York, Alabama, New Mexico, Virginia, Georgia, Connecticut and Tennessee.


Speculation, Inquiry, and a Quest for Purpose