The Glory of Outlining

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Even if Danielle Steel’s novels haven’t found their way onto your bookshelf, chances are you’ve heard of her. As one of the all-time best-selling authors, she has penned over 190 books, collectively selling an outstanding 800 million copies and counting. The figures are not just impressive—they are staggering. A testament to endurance and volume, her success is built on output, and, according to an older article making the rounds on Social Media again, she often manages five projects or more at once. But this is what I found shocking, unlike James Patterson, who also churns out multiple books on the fictional conveyor belt through collaboration, Steel crafts every word herself.

What’s the magic formula?

Her success is fueled by an unyielding, almost relentless, work ethic. Beginning her writing day at 8:30 am, she often continues after day breaks into night, sometimes spending 20 to 22 hours at her desk. Breakfast consists of a piece of toast, while bittersweet chocolate bars serve as her lunch. Hey, there are worse meals—I’d want to add a tablespoon of peanut butter to that bread, slightly charred. This may seem like a Spartan meal, but Steel is no ordinary writer. A sign that adorns her office declares, “There are no miracles. There is only discipline.” Critics might see her regimen as a self-inflicted Greek tragedy. Yes, she could certainly choose to write just one book per year, maintaining her best-selling author status, and perhaps find some much-needed rest. A little shut-eye, or downtime, isn’t a bad thing. But in pushing boundaries, she is an artist who might find solace in her own tireless rhythm.

Yes, amidst the pursuit, a question lingers. Is Steel doing what she loves or following a process? The answer is probably both. In writing, the routine matters, and I doubt she breaks it often. As Fleetwood Mac once sang, “Never break the chain.”

For many, myself included, finishing the first draft of a book is challenging. The joy often associated with a writer’s life can sometimes be a mirage, and I sometimes field the question, ‘Should I write a book?’ Yes, I start by trying to talk everyone out of it. The same goes for those thinking about running marathons, becoming a sales leader, climbing mountains, having children, driving in Crete, or hiking through South America to escape a political uprising. But few listen. I blame the creative muse.

In this new era of rapidly advancing Artificial Intelligence (AI), I’m getting the question even more these days as ChatGPT and others can impressively churn out volumes of text. I mean, some now think, ‘How hard can this be these days?’ The ghost in the machine has a knack for spinning a digital web, far superior to what comes out of the hotheads on late-night news. But considering the token ability of these models only allows for drops in the 500 to 2,000-word range, the work is lacking something vital. A soul. The human mind is a feat of engineering, so to speak, with its ability and memory recall. So, yes, while Danielle Steel’s discipline can compete with the machine, it’s her humanity that makes her work resonate.

Even if one wants to write with these tools, a true north is needed. And even for those who still dither away the old fashion way, the relics like myself, they require a guiding star too. Sure, some still surrender to the mind’s whims, letting the keys take them wherever they please.

But, for me, the outline is a non-negotiable

Not long ago, I cranked out a 160,000-word manuscript, a work that I toyed with for almost four years. Again, the initial draft remains a significant milestone. If you’ve read some of my endeavors, they are all somewhat different, but certain themes find their way on the page, even if an ending takes an unexpected turn. Still, I try to tinker with my process for each work: limiting the word count or time to write, adjusting the writing style, changing the perspective, or holding to a certain length and structure. But to put this draft into perspective, my latest novella in scope was closer to 30,000. The Dark Harp and Day Life Breaks came closer to the 50,000-word mark. So, I marveled, upon completion, how did I get here? Sigh, I know it’s not War and Peace or Atlas Shrugged, which come in at 500,000-words plus.

But anything is doable if one breaks the overall goal down by using constraints and leveraging an outline process. Consider this project management for the creative mind—a touch of structure for imaginative chaos. Outlining shouldn’t mean the story never changes. Or the characters don’t evolve, which would be a travesty. Books may be written by a writer, but tend to become a living and breathing organism, so to speak. Even after they are released to a broader community, the writer often loses the narrative.

There are many approaches. If you’ve read my thoughts on the power of taking notes, I’m a champion of the Zettelkasten method. I won’t oversell this here, but I love to chase where the mind goes, following the threads. So, if my attention leaps to another book, work, or post, I go with the flow. Type first. Categorize later. Edit thereafter. This is a special kind of chaotic focus. A merging of ideas. Some soar. Others are left on the cutting room floor. Using this approach, I have ten thousand article ideas and counting. Hundreds on the story front too. My modern-day reimagining of Attila the Hun running a bakery never took flight.

As I begin my day, I stare at my broader story outline. Sometimes, a new scene or chapter emerges, begging to be pursued. Then, I allow my Zettelkasten brain to take over and go. A hero’s quote, a random scene, or a character’s appearance—nothing is lost. I sometimes write descriptions, pages upon pages about leaves or the sound of silence. In a previous book, I loved describing baseball fields in rural communities, and I’d give them a mythical quality. Immense water towers with nearby windmills in the outfield to reflect weather conditions or chain-length fences set within abandoned rock queries. I don’t limit where my mind takes me. I type. Let it be, or, er, go.

So, What specific tooling do I use?

Numerous writing tools dot the market, and I’ve tried almost all of them; some still serve specific needs. Ulysses. Word. Drafts. Evernote. IA Writer. Storyist. But when managing a comprehensive project, nothing beats the grand champion of writing—Scrivener. These days, I spend less time writing with it and more time utilizing it to manage my entire project flow.

Almost all of my writing is done in Roam. See my Zettlekasten approach. Call this my current gold standard for creative conditioning. And for my process, the outline view in Scrivener is my go-to. If you’re after a more feature-rich outlining experience, the steroid approach, other options exist too. Plottr. OmniOutliner. As long as the product uses a .opml format, it doesn’t matter because Scrivener can take in your outline when you’re ready to write. Technically, it can accept anything. Here is a sample snapshot (no book in motion).

From Scrivener’s outline feature, one can view the entire work, beginning to end. As I’ve played with the Outliner feature more through the years, I find it remarkable in its simplicity. Here, I often only start with the book’s title and add a short synopsis. If I’m not ready to create or draft anything too elaborate yet, I’ll add a rough flow of the chapter in the notes—nothing major, easy stuff. The man in black fled across the desert. Or, for Thelma and Louise fans, two women stare out over the canyon inside their stolen convertible, holding hands, knowing there is only one way to truly be free.

At this stage, the book exists as a loose outline. Scrivener is flexible. A con, for some. But I wouldn’t have it any other way; rigidity can drive poor habits or take the story where the characters may not want to go. I also like to move the chapter flow around, which I do in Scrivener’s corkboard view—an electronic take on 3X5 manila cards. When looking across the entire project with this feature, sometimes, I’ll chuck an idea or entire chapter altogether.

I do still believe note cards, whiteboards, and even the good ole fashion chalkboard remain the gold standard for early outlines. There is something magical about touching a tangible, physical card. But, eventually, one needs to get the structure routed in the digital space unless the old-school pen-and-paper itch strikes. Or one hungers to be like Fitzgerald or pen like Hemingway.

The versatility of the software’s digital outline function can also be extended to characters and places. Before starting my magnum opus, I do jot down character sketches. Note, I never overindulge here; a healthy warning. I’ve seen friends spend months on these, a practice beneficial for non-fiction or historical books. In the realm of fiction, it’s all about the story, and the muse mustn’t be kept waiting. Procrastination can be a writer’s downfall. But the appeal of these sections is to facilitate consistency throughout the book. If the story’s hero is six foot two with flowing red hair, I don’t want him sporting blonde hair five chapters later. Hey, it happens. Conversely, I may want to call back to a minor detail to enhance the story further.

Once the outline for the story (and characters too) are in place, what happens next? Depending on the size, the newly created world may appear overwhelming. For example, let’s say there are thirty unique chapters. Multiply that by three to five thousand words; well, that’s a ton of words. Go forth. But thinking one has to belt out that many words, I might want to watch the Cardinals’ closer blow another save instead. Or rearrange my desk—anything but write.

To manage this, I leverage Scapple, a versatile tool that complements Scrivener made by the same development team. What makes Scrivener stand out is its compatibility—it can import data from various sources. So if one has drafted anything in Microsoft Word or taken notes in Roam, they can be easily transferred into your project. But the feature that sets Scapple and Scrivener apart is the seamless drag-and-drop feature. Once my so-called rigid yet flexible outline is in place, I’ll drag two or three chapters into Scapple. And from within Scapple, I’ll begin to map out the chapter in more detail. Here, I can add sections and think about the detailed construct of the individual chapter. Map the characters. Build a timeline. The world is at my fingertips. Typically, I’ll create bubbles creating scenes within the chapters. Sometimes, these are five to ten various bubbles. When I’m satisfied with my mind-mapping brainstorming session, I’ll transfer these sections back into Scrivener.

Mind Map in Scapple

But the Process Flow Remains Essential.

First, I’ll convert the initial document in the Scrivener outline into a folder. And then, I’ll drag these new chapter sections from Scapple into this newly created folder. Our previous mathematical approach allows me to break down the daunting 90,000 words into blocks. One book equals 90,000 words. Thirty Chapters, breaking down to 3,000 words each, equals 90,000 words. And 180 sections, assuming 500 words, equals 90,000 words. By following this approach, I’m more like to write and not turn on the Cardinals game, which brings with it a certain amount of pain and suffering? Right? Maybe not? Sometimes, you can’t look away from disaster. Still, instead of trying to finish your massive memoir from birth to centenarian, breaking the problem down helps.

Next, I integrate these individual blocks into my to-do list in Roam. Or, if you prefer another task management tool, go for it. Google Tasks. Things. Or even the tried-and-true method of pen and paper works too. The key here is to foster a sense of continuity and momentum. Never break the chain again or let things sit too long. Writer each day, even if it’s only a few hundred words. R.L. Stein writes 2,000 words daily and then puts the pen down. For me, my marathon conditioning is more in the 1,000-word range.

When I say write, again, don’t hold back and let it rip. In Roam, I’ll note the section I’m working on and set my fingers free. There is something magical about pounding away on a mechanical keyboard. But, hey, use what you want. As Russel Crowe says in Gladiator, “Are you not entertained?” I think that’s important in writing. And, at times, I’ll have a single Roam bullet morph into thousands of words. On other days, certain sections are challenging. I’ll start the snippet but another book or a random blog post beckons. If this inspiration from the muse strikes me like some lightning bolt or just a tiny murmur of thunder, I’ll hit enter, creating a new bullet, and move on. This is the power of what’s called the slip box using my hacked Zettlekasten note-taking method. There is a method to the madness. As a side note, I use the Grammarly Browser Extension to catch anything egregious, but I mostly just ignore any spelling mistakes.

At day’s end, I’ll review my work, refining and refining, until it’s ready to be transferred through a markdown export, depending on size, or a simple cut-and-paste exercise into Scrivener. As a side note, in the first draft, I don’t necessarily write linearly. Sometimes, I begin in the middle of the outline. For my latest draft, which may never see the light of day, I wrote the last sentence first. Go figure.

Corkboard View in Scrivener

While working, I often highlight the chapter folder in Scrivener. This simple action allows me to see the total word count of the chapter and reread my broken-down blocks in their entirety. Once I feel that the chapter is coming into form, I’ll highlight the entire work, including subsections and documents, and use Scrivener’s merge feature, collapsing all of the documents into one unified piece. Then, it’s time for housekeeping. I’ll stylize the document, remove any unwarranted page breaks, convert to smart quotes, and zap any gremlins hiding in the formatting. Scrivener has wonderful text clean-up tools, which are lifesavers, especially if you’re someone who frequently switches between different applications or devices.

Harnessing Fear and Embracing Flexibility

Then, I’ll repeat the process for the next chapter. But remember, my approach is fluid and dynamic. I may skip ahead or sideways. And even in the outline, I may work the process in reverse. Nothing says I can’t brainstorm in Scapple and move those chapters into the Outline feature first. One has the power at their fingertips. Keeping the format flexible makes it easy to put pen to paper and not be overcome with the crazy overpowering fear that rides with Ricky Bobby in Talladega Nights. “You gotta learn to drive with the fear, and there ain’t nothing more God damn frightening than driving with a live cougar in the car.” Hey, writing isn’t as scary as driving blindfolded, but I think it exists in certain stages of the writing process. Before hitting ‘send’ on a newsletter, I do notice a tinge before hitting enter. Am I wasting my subscriber’s precious time? Will they hate me more now? Or will they delete it and move on?

And yes, sometimes, one may think they have this incredibly written piece, the heavens aligning in the mind, and then it never works out. Other times, the words flow, and a sort of magic comes. And a little luck never hurts too. Admittedly, many of those 160,000 plus words will likely find the cutting room floor. This is the nature of battling the keyboard—it’s just a draft. The real challenge lies in the editing process. But, as always, we march on.

Yes, writing can be a lonely and daunting endeavor, a mountain that seems impossible to climb. But with the right tools, strategies, approach, and mindset, it can be made more approachable and even enjoyable. Yes, I may say, ‘Never write a novel.’ But remember, your story is worth telling, and the world is waiting to read it. Don’t let the fear of a blank page hold you back. Leverage the power of flexible outlining, break down your work into manageable blocks, and let your creativity flow. Sure, there will be moments of doubt and fear, but remember—even the best of stories have their rough drafts. When your future self steps back and surveys the completed work, you’ll realize that the journey, with all its challenges and triumphs, has been worth every word.

And thank you for reading.

Notes:

  • Apologies for running back through the Zettelkasten system, more than a few times here. I just believe it’s important.
  • The writing links to the various tools are embedded within the post. There is so much more than Word and Docs in this world, try one.
  • The Scapple Map pictured is blurred out because it’s an actual working copy. Note, the Scrivener shots are just examples, nothing in progress.
  • The picture taken was from a book randomly chosen at an airport in Greece.