Hybrid Outlining
The sportswriter Walter Wellesley "Red" Smith was once asked if writing a daily sports column was a difficult task. ”Why, no,” he replied. “You simply sit down at the typewriter, open your veins, and bleed."
It's an apt statement. Writing is hard enough under the best of circumstances. It requires a certain state of mind, focus, and willingness to put ourselves out there. For many of us, this challenge is compounded by trying to squeeze the practice into the chaos of our daily lives. Busy jobs. Parenting. Housework. And an endless list of other obligations.
This challenge led me to develop a practice I call Hybrid Outlining. Hybrid Outlining is a progressive writing practice that breaks the creative process down into a series of distinct steps. The practice is designed to speed up the writing process by generating cohesive outlines that translate easily into finished prose while avoiding premature self-editing. Each step in the Hybrid Outlining process can be focused on during a relatively short writing session. The way the process is structured, I can come back to a piece I am drafting and quickly pick up where I left off. This allows me to work in shorter bursts while minimizing efficiency loss from having to mentally reload context at the beginning of a writing session.
Below, I've provided a detailed summary of the hybrid outlining process. The practice is still evolving, and it's not a silver bullet. But, through years of trial and error, I've found this approach helps make the creative process easier, more systematic, and more enjoyable. I'm sharing in hopes that you might find something useful here as well.
Background
The early stages of my writing process used to consist of two steps. First, I would create a rough bulleted outline. Each bullet point in these outlines was comprised of only a few words or at most an incomplete sentence. Next, I would attempt to write the first draft by converting this outline into prose comprised of full sentences grouped into paragraphs and sections. Over time, I consistently experienced two problems with this workflow.
First, I would often find that the rough outlines I had created in the first step did not translate directly into the kind of logical flow I thought they would when I generated them. When writing these short, isolated bullet points, it felt as though I was creating a cohesive train of thought. When I sat down to convert the outline into a first draft, I quickly found that was not the case. The pieces just wouldn't snap together. My method for creating outlines was allowing me to gloss over too much detail, creating fragile logical flows that crumbled all too readily under the weight of the drafting process.
The second problem with this approach was that I couldn't keep my inner self-critic from inhibiting my creative flow. The moment I switched over from the rough outline and began drafting prose, I got stuck obsessing over minute details like word choice and sentence structure. Instead of letting the piece take shape before focusing on these details, I was splitting hairs. I was like a sculptor who, instead of carving the rough shape of his subject's body first, was stymied by trying to perfect the eyelashes.
Like anyone who's ever tried to improve their writing process, I'd heard all the advice about generating dirty first drafts. But I found this devilishly to do. In reflecting on this challenge, I noted something interesting—I didn't struggle with perfectionism when I was drafting the outline. When outlining, I often achieved a flow state; ideas would pour out of me as quickly as I could type them. But as soon as I started drafting prose, it was as if a switch had been flipped. My inner editor was dominating the process. It was stifling.
Hybrid Outlining
I began to ask: What if I could tap into the free-flowing state I experienced when outlining but do so in a way that consistently created cohesive outlines? Could I find a way to generate outlines that translate more readily into first drafts and ultimately publishable prose? These questions led me to create the practice I call hybrid outlining.
The general idea of hybrid outlining is simple. I begin with an outline but with one critical difference from what I was doing before—each bullet point must be written as a complete sentence. Once this outline is complete, I combine the sentences into paragraphs and sections, performing various levels of editing as I go.
This process gives me the best of both worlds. Working first in outline form keeps me focused on generating ideas, not editing them. But taking the extra time to write in complete sentences instead of staccato words and phrases adds just enough pressure to ensure that ideas actually fit together and flow cohesively. Below, I have provided a step-by-step look at the practice of hybrid outlining and how I use it to go from the seed of an idea to a finished piece.
Step 1 - Create Atomic Bullets
I begin the writing process with a simple bulleted outline. These days, I do most of my writing in Roam Research and Ulysses, but any word processor will do. I prefer to use unordered lists because I find numbered outlines to be extraneous and distracting.
Next, I begin writing individual ideas in complete sentences. I write each sentence such that it stands on its own and conveys a single idea. I call these "atomic bullets”. If I find that I am actually trying to convey two different ideas with one bullet, I will break it into two. These ideas will get combined later in the process. I find that keeping them atomic at this stage forces me to be more clear with myself about the specific point that each sentence is trying to make.
The most important part of this process is that I force myself to write in complete sentences, ensuring that each bullet flows logically to the next. Often, I find it helpful to stop momentarily before I begin to type a bullet. I take a few seconds to think critically about what I am trying to convey. Sometimes I'll even say it out loud. Once I’m clear on the idea, I write the sentence with no editing allowed. The priority at this stage is to get it on the page!
Then, I simply wash, rinse, and repeat. What did the last sentence convey? And what comes after that? Weaving these ideas into a series of complete and atomic sentences creates a consistent logical flow. But something about working in outline mode keeps me in the right headspace—focusing on ideation and avoiding premature self-editing.
A note on indentation: During step one, I will use some indentation to represent the relationship between ideas. Supporting arguments and examples get nested under high-level declarations, and so on. This starts to paint a picture of how I will later break up the atomic bullets into paragraphs, headings, and sub-headings. One note on this is that I try not to be too concerned about getting the nesting "right" at first. I have found that if I get too focused on this, it breaks up my creative flow. So if a hierarchical relationship between two atomic bullets is clear, I will readily apply indentation. If there's any doubt in my mind, I will default to less indentation during step one. This is because the goal of the initial drafting process is to get the ideas on the page. Fine-tuning them, moving them around, grouping them, etc all come later.
Step 2 - Collapse and Group Ideas
Once I feel like I have the entire blog post, essay, or section I am working on drafted as atomic bullets, I proceed to step two. This step involves combining the atomic bullets into paragraphs. If I succeeded in creating a logical flow in step one, then step two is as simple as putting the cursor in front of one bullet and hitting delete until it "collapses" onto the bullet preceding it. I start at the top and work my way down, collapsing bullets into the groupings that will form the paragraphs of my final piece.
As mentioned above, I apply indentation during step one in order to bring some structure and grouping to the piece. But it is during step two that I am much more focused on this organizational aspect of the writing process. I find that working on a structure and grouping shifts me to a different headspace than the drafting process requires. So making it a distinct step in the process helps me avoid unnecessary context shifting. At the end of step two, my document will still be in bulleted form, but instead of each bullet containing a single sentence, it will contain a paragraph.
An added benefit to working in stages like this is that it gives me a clear visual indication of where I am at in the drafting process. This is particularly helpful for longer articles that require multiple drafting sessions broken out over several days or weeks. When I see an individual bullet consisting of multiple sentences, those sentences have already been through step two. They do not need to be revisited until I'm ready for the third and final step. Conversely, if I see a series of atomic bullets, I know that those have not been through the collapsing and grouping process. These clear visual signals help bring a more systematic workflow to my writing process.
A final note here is that I do some light editing during the grouping phase; light being the operative word. During this stage, I am primarily focused on correcting any glaring grammatical errors, fixing broken sentences, adding missing words, etc. Also, although I strive to reach a cohesive flow in step one, once I start to combine the bullets together, there is always some smoothing over left to do. So during the collapsing and grouping stage, I am also making minor tweaks to sentence structure and adding/re-ordering atomic bullets as needed to create a cohesive flow. I try and avoid stylistic editing during this phase; that comes later.
Step 3 - Final Edits
Once I have gone through the collapsing and grouping stage, it's time for the final step in my process—final edits. During this stage, I am focused on two core goals:
Dialing in the wording, style, and flow;
Establishing the final structure (e.g. headings, article title, and article sub-title)
Again, I start at the top of the draft, reading the first paragraph. This time, I let my inner editor loose, allowing him to scrutinize the style, word choice, sentence structure, etc until each paragraph is as I want it. Once it's good, I put my cursor at the top of the paragraph and hit delete so that the bullet goes away. What's left is a completed paragraph ready to publish! Again, I find this method helpful because it gives me a visual indication of progress—any paragraph that still has a bullet in front of it needs final editing, any paragraph without a bullet is complete.
During step three, I also insert headings to group paragraphs together. A quick tip: Sometimes, I can sense a group of paragraphs all belong under a common heading but I'm not sure exactly what I want the heading to be. In these cases, I'll either write down the first thing that comes to mind or even simply type the letter "X" and apply a heading style to it. This keeps me from getting stuck and minimizes the need for intensive context shifting.
Once every paragraph has been edited, I'll come back and finalize the headings, title, and subtitle. I'll usually read through the piece at least a couple more times to do some final smoothing over. After that, I'm done! The piece has been through all three steps of the Hybrid Outlining process and is ready to publish!
Why Hybrid Outlining works for me
Hybrid outlining has worked well for me for several reasons:
Free-flow drafting: There is something liberating about working in an outline mode early in the process. I find I don't get so bogged down on minutiae like word choice and sentence structure. I can instead focus on ideation and the overall flow of the piece. This small shift somehow helps give me permission to write more freely than if I attempt to do a dirty first draft with sentences strung together into paragraphs.
Pressuring logic and structure early: Starting with complete sentences that flow from one to the next puts the right amount of pressure on me to ensure that the logic and structure of the piece are sound. I struggle with this when using short-form outlines, which I usually find are full of logical holes and do not translate well into a first draft. Hybrid outlining doesn't suffer from this shortcoming. Instead, I'm able to pressure the ideas earlier in the process. This not only makes the subsequent drafting stages easier but has the added benefit of weeding out ideas that aren't quite ready for prime time.
Systematic process: And finally, the hybrid outlining process includes a systematic use of visual cues to indicate where I'm at in the drafting and editing process. This helps me reload the context and get to work quickly at the beginning of each writing session. This is particularly helpful for the times when I'm forced to break the process down into a series of shorter sessions due to constraints in my schedule.
I hope you find something useful in the Hybrid Outlining process. If you end up putting it into practice, either wholesale or just bits and pieces, I'd love to hear from you on Twitter or over on LinkedIn.
What works for you? What doesn't? Have you developed similar practices? Do you have other suggestions? I'm continually looking to refine my writing process and will update this piece as my approach evolves. I would love to connect and share ideas! Thank you for reading.
PS - If you found this article helpful, consider sharing it with a friend!