Writing and Reflecting in Obsidian — Writing Fiction

This is part 5 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 the process I use to turn my ideas into prose for both short- and long-form fiction. 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.

Planning and incubating my fiction is all well and good, but how does that translate to actual words on a page? While the majority of my focus is finishing that one novel I’ve been struggling to pass like a kidney stone for past decade, I’ve also been experimenting with short stories recently, especially since Obsidian enabled me to carry more of my ideas to fruition. The process I use is slightly different for both my short and long fiction, but they follow the same ideological practice of breaking down a large, seemingly impossible task, like “Write a story,” into smaller, more manageable chunks, like “Identify the problem or crisis the protagonist faces.” I’ll also highlight the similarities between my short- and long-form fiction where relevant.

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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.

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Writing and Reflecting in Obsidian — Morning Pages and Daily Notes

This is part 3 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 details how I make use of plugins like Periodic Notes, Templater, QuickAdd, and Dataview to manage my Daily Notes Page and Morning Pages writing practice. 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.

The primary activity I use Obsidian for is writing. In terms of volume of words and time spent in the app, the majority of this writing would actually be classified as journaling. Journaling is what brought me to Obsidian in the first place, the promise of being able to see connections between different entries across the months and years of my writing, and it has certainly paid off to be able to to journal in this way.

Journaling Workbench
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Writing and Reflecting in Obsidian — From Evernote

In Search of a Better Journal

This is part 2 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 history with journaling and digital note-taking tools, accounting for how I arrived at Obsidian from my first digital database, Evernote. 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.

How to Record Everything?

I haven’t always been so interested in writing everything down, but I have always had an interest in writing something down. When I was in college, I needed a notebook primarily to keep up with assignments and follow classroom discussions. (It was an entirely discussion-based curriculum, and the rules of decorum meant that if you didn’t have a way to keep track of what was said and what you wanted to say, you may never end up participating at all.) This was back when I was an aspiring musician as well, so I soon found myself relying on a pocket-sized Moleskine notebook I carried with me wherever I went so I could parse out song lyrics, doodle when I was bored in school, and write down assignment deadlines.

When I got an iPod Touch, sometime in 2008 or 2009, I installed Evernote, sold on the idea that I would be able to store—and recall—well, everything. That was the promise of the Information Age, wasn’t it? To leverage the awesome storage and computing power of technology to record and interpret data about our world in ways never before thought possible?

Classic Evernote, c. 2008
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Writing and Reflecting in Obsidian — Overview and Index

This is the first part 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 serves as an overview and index for the rest of the series, which will explore in depth how I use Obsidian for note-taking, journaling, and creative writing. 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.

My graph as of 2023-01-01

In Search of a Digital Note-Taking Analogue

What are the primary virtues of analog note-taking? Immediacy, for one. A notebook requires no loading time (aside from locating said notebook,) no power source (if there’s sufficient light,) and creating a new note is as fast as turning the page. Geography is another one. Our brains evolved to remember the relative locations of things, and physical books maintain that sense of space—the pages exist in an immutable order that becomes familiar over time. Then there’s portability. I used to keep a Field Notes notebook in my back pocket at all times, and my current Leuchtturm 1917 notebook fits as easily in my small café bag as it does in any of my backpacks.

But there are some disadvantages to analog note-taking that left me wanting more. While my Leuchtturm has page numbers that enable me to create an index of its, that index is only really useful for that single volume. I’m currently on my twelfth volume, so unless I’m going to maintain an independent index, I can no longer keep track of where all my writing lives. Another disadvantage is impermanence. On the one hand, we still have Leonardo DaVinci’s notebooks some five hundred years after his death, but on the other hand, I lost one of my Field Notes notebooks on a bike ride back from the climbing gym and I never saw it again. Thirdly, so much of what I read now is digital that it would be much simpler for me to copy and paste excerpts to add commentary than to painstakingly write down every piece of information I want to recall—and then index it.

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Current Projects: Winter 2021

I quit my day job in 2018 because I was fed up with how other people were spending my time, and I wanted to see what I would do with it if no one was buying it from me. At the time, I was rewriting a novel I had (foolishly) self-published back in 2016, finishing a second one I started in 2015, and trying to find a way to make writing more of a central focus in my life.

By the end of 2018, I had gotten involved with a local writing critique group, started attending a weekly philosophy discussion series, and volunteered to write for both a charter school and a reused construction materials store. At The People’s Colloquium, I was able to share my works in progress with other writers to get their feedback, and I got to read a lot of other people’s writing to share my perspective on as well.

In January 2019, my fiancée and I discovered that we were going to be parents and had about seven and a half months to get ready. We needed a family car and an apartment that would fit the three of us (plus three pets), so I applied for the fastest employment I could find, through a temp agency. I kept writing and kept attending my discussion groups right up to the week of my child’s birth, but when he was born, everything changed. Suddenly, everything I knew about how to spend my time was irrelevant, and I had to start over from scratch.

My world was already rocked beyond recognition by the time COVID-19 was declared a global pandemic in March 2020, and when the dust finally settled a few months later, I woke up in a new house with a wife, a son, a gig as a copywriter, and no day job to speak of. My wife’s work is very fulfilling, so she’s still going in 30–40 hours a week while I stay home with my kid.

I have to fight hard to make time to write despite renovations, house guests, maintenance, and all the demands involved with being solely responsible for keeping a toddler occupied, safe, and engaged for twelve hours a day. It’s not easy, and most days I can only manage to eke out my three morning pages, but I’m determined to finish what I started before stopping to figure out what’s next.

With all that in mind, and in the interest of opening the garage, here’s what I’m working on as of this winter 2021:

Morning Pages

Since I left the workplace in August 2020, I have written three pages in my journal every morning. As Julia Cameron recommends, I write a stream of consciousness and try to do it first thing in the morning. Cameron also recommends writing longhand, but I haven’t been able to commit to that. I’m too insistent on digitizing my notes. Before becoming a parent, I would transcribe my handwritten journal into a digital format for archival and retrieval purposes, but in the aftermath of losing all semblance of control over my time, I’ve had to resort to digital.

There’s something special about three pages. It’s between 750 and 1,000 words, depending on how you count (I shoot for a thousand when I’m typing) and that’s just long enough for me to run out of things to talk about when I realize I’m only halfway through. Then, when the noise of whatever ephemera I’ve been documenting dies down, there’s a spark of insight that leads me through writing to my inner thoughts and preoccupations. When I write my morning pages, I’m practicing sitting down to write and tapping into that part of my mind that has something to say. It’s like a morning workout routine.

Everything’s Totally Manageable

It’s been nine years since I started working on the novel that led me to my interest in writing. “Everything’s Totally Manageable” is the working title I have given to a story that started out as an autobiography but has slowly evolved into a piece of realist fiction. I started writing it as something to do instead of smoking cigarettes on my breaks from work, but then some unexpected life events changed the course of the project, and I’ve been desperately trying to finish it ever since.

The story follows a group of college students grappling with the reality of their friend’s suicide while immersed in an undergraduate philosophy program and experimenting with mind-altering substances. Its central questions concern the nature of reality, what constitutes meaning, and whether life itself is even worth living.

Because I was starting with no formal training in writing—only a minor in comparative literature—I could only write by trial and error. My first draft was over a hundred thousand words, far too long for a debut novel by an unknown author. When I rewrote it to a more manageable size, I experimented with getting closer to the true facts of my life before moving farther away from them, tried melding and separating characters, worked through different tenses and timeframes.

Now I’m about ten thousand words into what, I hope, will be the last draft I write without professional assistance. After this, I’m either going to hire an editor or start querying agents. To reach this goal, I reengaged with a new writing critique group born from The People’s Colloquium called The Critiquery, which I’ll address momentarily.

The Critiquery

One thing I wish I knew when I started writing “Everything’s Totally Manageable” was the value of working alongside a community of like-minded individuals. Although I’ve read several books on the craft of writing, nothing has improved the quality of my own like sharing feedback with other writers who are struggling to bring their own ideas to fruition.

I spent the first eight years of my writing life alone. The People’s Colloquium was my first writing group, and I barely got to know them before parenting permanently changed my relationship to time. When I could finally allocate an hour or two a week to a critique group, the pandemic had dissolved the in-person roundtables and produced new video conference rooms.

The Critiquery represents one such development, and they emailed me to let me know they were conducting weekly sessions again via Zoom. I started attending their sessions in May 2021, while I was working to finish the second-to-last draft of my novel.

We meet for one hour every week, late enough that my wife is home from work and can look after our son, and we discuss submissions up to 10,000 words. At first, I balked at such a restrictive limit, but I have since learned to appreciate how it makes me focus my writing on brevity and concision. I look forward to it every week, and I volunteer to moderate the discussion about once a month.

Professional Copywriting

After I left my day job in 2018, I was approached by a former coworker about writing copy for a marketing firm. I hadn’t written to anyone else’s specifications or requirements since I was in college, so I accepted, thinking it would be a good pivot into a possible new career. By the beginning of 2020, I had signed on to write site pages for a new startup in Portland, followed by monthly blog articles and product descriptions for items on their menu.

Every couple of weeks I get an order for a new round of copy and I strive to finish any outstanding assignments before returning to my creative projects. This work still has to fit around the schedule of my primary job—parenting—but my wife helps me dedicate some time to writing throughout the week. I couldn’t do any of this without her support.

The Curious Writer

Lastly, I got an unexpected gift from my sister during a family reunion in early 2019, the same trip my fiancée and I announced our pregnancy. It was a textbook from one of her classes at the University of New Orleans titled, The Curious Writer. Since I lacked any formal education in writing, I was ecstatic to have any kind of guide—especially since my impending fatherhood precluded any possibility for further education for at least another five years.

The Curious Writer aims to teach writing as part of the larger process of academic inquiry, guiding students to ask questions, look for answers, engage with different viewpoints, and reflect on the whole experience. Despite spending so much time writing fiction, I have great interest in learning to get at the heart of my ideas and present them in a compelling way to the public.

With so much else on my plate, I’ll admit that plodding through The Curious Writer is often the last thing on my to-do list, but I still have been making progress and one of the reasons I reactivated my weblog was to have some public outlet for the essays I produce. I’m trying to put into practice what I’m learning as I learn it, and writing essays is something I’d like to learn to do well.

Opening the Garage

Here, let me show you my workbench.

For too long, I’ve been working with the garage door closed, making my machinations invisible to the curiosity of any passers-by. That closed-off outward appearance might even make it look like I haven’t been working on anything at all.

But I have. And I’d like to share some of it with you. Let me start by showing you my tools and—in time—we might see some of the end result.

All of the work starts in one of three places: my bullet journal, an app called Drafts, or another app, Obsidian.

My Bullet Journal

This is my favorite tool, and there was a time when it was the main one I used.

I use a dot grid A5 notebook and a refillable fountain pen for my primary writing whenever I’m writing analog. Over the past several years, I’ve experimented with a modified Bullet Journal Method that combines longform writing with bullet journaling using the gridlines of each page.

Like most of my tools, my notebook is simple and direct. I use an index in the front to keep track of my thoughts, and the notebook comes printed with page numbers for reference. At regular intervals, I would type up this handwritten material on my computer.

You’ll notice that the green notebook, “Volume VI” ends in August 2019. When my son was born, the blue notebook I had started became the journal of his life thus far.

It was then that I had to adopt a more casual and immediate note-taking system. For the time being, I’m letting my current notebook and digital writing be bound to each other only by date, for reasons I may get into later.


Drafts is where most of my text starts because it has configurable actions to send whatever I write wherever it needs to go. Sporadically, I need to look something up on YouTube, sometimes I need to add a reminder to do something later, and sometimes I’m dictating an idea about one of my writing projects, but the thing all those needs have in common is a piece of text in a window.

It works exactly like a sticky note pad, offering a blank screen every time I open it and letting me tear off whatever I’m working on to take to the next tool.

I use three primary action groups. One is just basic iPhone actions like sending a text, adding a reminder, or creating a calendar event. The second is a search bar that lets me search sites like YouTube, Google Images, Wikipedia, Snopes or Amazon with the press of a button.

The third is all about formatting my Draft to act as a digital bullet journal entry and getting it into Obisidian for development and long-term storage.

Obsidian, Ulysses, and Scrivener

I have made Obsidian the main workhorse of my garage for two reasons: it works with plain text Markdown files and is designed with linking notes in mind.

Picture me taking a walk with my toddler and having one hand free when I get an idea I want to use for my upcoming novel. I take my phone out of my pocket, type a couple of lines into a blank Draft, and send it to Obsidian later.

Using links, anything I add to my daily notes page can reference any other document in my Vault. I can generate an outline of a work-in-progress to remind myself what I still have to write. There are also many user-submitted plugins that contribute additional functionality, like a consolidated to-do list. It’s like having a digital bullet journal.

Obsidian also offers some neat visualization options to view the relationships between these linked notes. The graph above is my entire Vault, including all of my digitized journals going back to 2003 and some references to documents that I haven’t had the chance to write yet. I can click on any node to jump right back into the thought or see its connections to related ideas.

Since Obsidian works in plain text and Markdown, I need other tools for finished work, something I’m going to submit to a client or publish to a weblog.

Ulysses loves Markdown, and is by far the easiest way for me to convert finished copy into something submittable. It supports user-configurable export formats, so the same raw text can be turned into a manuscript submission, print-ready prose, or a weblog entry. I use it for anything less complicated than a full-length novel, although I have certainly written an entire novel draft using nothing but Ulysses.

Scrivener, on the other hand, is like its own production facility. Instead of working solely with text, Scrivener will store any kind of media file in a virtual “binder” alongside the prose in progress. It supports linking between documents, annotations, comments, and it has a robust export suite to dial in specific print requirements. I like it for planning large-scale projects that have a lot of moving parts and multimedia inspiration. I’ve even converted some of my writing references like John Truby’s The Anatomy of Story into Scrivener templates to facilitate the creation of new projects.

The Work

Regardless of what I end up working on, my writing days all start the same way: with morning pages. “Morning Pages are three pages of longhand, stream of consciousness writing, done first thing in the morning,” according to Julia Cameron who popularized the term. On average, three pages in my notebook amounts to about a thousand words, so that’s my target when my morning pages take place digitally. Since I type twice as fast as I write and I’m the parent of a young child, these usually take place in Obsidian.

I use my morning pages to get a sense of what I’m going to be working on for the day and what challenges might oppose that progress. They start a daily note page for each day that I’ll add to as the day goes on using timestamps to cross-reference notes that might exist elsewhere, like in my journal.

Most of the time, I’m writing for my copywriting job or working on my novels, but I’ve also been studying personal essays and I think there’s room in my workflow to experiment with some more of those. Since I have this weblog, I’m going to start thinking out loud a bit more and making more of these thoughts public.

This is my first post in a long while, but in the interest of sharing my work with any interested onlookers, I’m going to be publishing something new here every Friday, weather permitting.

Thanks for stopping by to check in, and I hope to see you around again soon.