Hating & Making Outlines Work (For Your Work)

I’ve long thought of “outline” as a dirty word when it comes to fiction. And here’s my best attempt to break down why: 

The inspiration for Braxton Barrett’s Beautiful Mind big board formally called out as such on page 141 of Heroin Highway—and the, “Thumbtacked mugshots neatly pressed into cork and all-caps dry erase marker in myriad colors intersected with a connecting yarn rainbow from top to bottom and left to right. Or right to left. Or both. Or all of the above.” observed in brain-hurting fashion by Tomas Trevino on the preceding pages—mandated a shoutout to Russell Crowe’s John Nash. It was also absolutely inspired by Jack Ryan—either Tom Clancy’s illuminating techno buildup on the page or Amazon Prime’s incisive interpretation on whatever screen you prefer. [Physical manifestation of your favorite title character’s case-building rabbit holed psychosis goes here.] 

But before pop culture punched it up, Braxton’s big board was formulated by nightmare fuel.  

I had dreams about my desk going through an HGTV renovation gone wrong, unspooling the connected dots from my brain on Oxford® Ruled index cards and hot pink Post-It® Super Sticky Notes and precision-cut balls of your grandmother’s spun thread. The stress caused by thinking that sequentially. The petulance in the assumed limitations of a paint-by-numbers approach to raw storytelling. The existential dread that comes from knowing that peers—friends, even—who believe in outlines like they believe in breathing have published and even moved past their day jobs into full-time fiction lives while I had failed to finish even a single manuscript. 

Throughout my 9-to-5 writing life at some of the world’s favorite brands and its best creative agencies, strategy has played a vital role in the storytelling I’ve been hashtag blessed as the kids say to experience and share with the world. Brand Guidelines. Do and Don’t bullet points. The fabric of the idea of knowing the rules well enough to break them. When and where to do so. The box, in and of itself, forever chasing what’s really in it, and, just as importantly, what’s not. 

I wanted—needed, really—my fiction journey to be different so I could feel the difference between what I’ve done for a living for all of my adult life and my de facto Corporate America Exit Plan. 

Early on in my fiction experiments I mostly tried—and mostly failed—to think and plan too far ahead, feeling like I needed to solve problems that didn’t exist yet in worlds that I was literally making up as I went. Ironically, what should have served to create a sense of bigness that I could literally see growing before me made the make-believe feel extremely small—and that felt more claustrophobic than Penrose steps that doubled as a word pantry. With instructions that came in IKEA. 

I was starving for an answer. And I was stuck in my own head. I started something new again and again and again. 

Now, you could argue that a big reason why exactly all of my original dalliances with fiction fizzled out was the catch-22 winking back from the cursor on the page and not truly knowing where I was going. I was relentlessly at play; fundamentally, the monkeys banging cymbals were at war. 

Even as the outline of an outline was formed, juvenile mental crescendo roared: 

Where would the unprocessed drama live and breathe, as real and natural on the page as it was to me—and hopefully, to 10,000 or so of my new best friends? How could I possibly remain (buzzword alert) organic, allowing the people inside the MacBook Pro to tell me what to do as exploring all five senses around the scenes almost turned places into characters themselves? 

In order to truly transition from copywriter to author, I had to tell myself the truth and give myself permission to re-learn some things about why words matter—and why the meaning we give them can be as freeing as we once thought confining.   

Even as the first definition of outline includes the word “enclosing,” it’s followed by “or” and then “indicating” the shape of an object. 

It’s a profile. A form. An artist’s impression. 

And the second definition is a general description or plan giving the essential features of something but not the detail. 

Summary. Synopsis. Skeleton sketch.  

Holy shit.  

Now officially out of excuses, and, living in the city with the most bridges in the world, I went to work on building one of my own. The only question left to answer was how to meet in the middle of a full, old school outline and Nike’s (paraphrasing) Just Bleeping Do It. 

I’ve been decently successful as a professional writer, so I didn’t turn my back on ad copy system clues and queues. Braxton Barrett, for example, became a tagline of sorts: “The Captain of all the squads but not Captain America.” His wife, Aimee, an invention approaching millennial-stamped impact statement status: Gritty Southern Belle. #LFG

Crystallizing Cairo Martínez into a single anything felt insufficient, so I thought about what actors I would want to play him and became unable to escape the wide-ranging emotions conjured by John Leguizamo’s one-man shows. I knew at some point I wanted to introduce a rival-slash-BFF for Braxton, and exploring all three components gave my character outline the idea of, “The Scottie Pippen of right-hand-men,” Braxton Barrett’s Human Mirror, and Gerard Butler in Den of Thieves (a less weary version; right before all the mistakes start catching up to him). Enter: T.D. Thompson. Mayor Carlisle Card became the juxtaposition of my unabashed love for alliteration and my hand-dipped-in-Kentucky-Blue hatred for the Louisville Cardinals—James Woods without the lisp. 

It is my sincere hope that Paddy Holland reads like the little brother you’d actually want to have and you can see James Pickens, Jr., playing Bubba Barrel. That Rachel James might not need a ladder to climb in that second story window. And Lyndsey Chappa is The Boss With The Sauce (you’re welcome, Sweet Baby Ray’s Summer Grill Masters). All kidding aside: Tomas Trevino is the last Russian Nesting Doll, Jon Huertas in Generation Kill > Jon Huertas in Castle. 

Ultimately, an all-encompassing outline wasn’t going to work for me—and that’s a short story unto itself. 

My original intent (read: the version I initially shopped via traditional publishing methods) was to open Heroin Highway with a letter from Braxton Barrett’s son some twenty years in the future and then flash back to the moment that set this whole universe on its collision course. Parallel, I had planned to spend much more—and much more specific—time deep in the backroads of Kentucky because the highway was hyper-focused on a handful of people, places, and things. At one point, I even changed the title of the work on some highbrow literary bent that tried way too hard to make the idea something way more than what it was. My original outline had made things far too simple and I found myself forcing in elements that seemed like they could create more elegant—and perhaps meaningful—solutions. 

And then I went back to who these people were telling me they wanted to be. What they wanted to do. And where that meant the story had to go. I didn’t start over…but I had to go all the way back to the beginning and find the right way in for these folks. 

In the Acknowledgements section at the end of the book, I talk about how real life forced me to take an honest look at the connective tissue to show the truth trapped within the original outline of the story. How unpacking what was working—and, more importantly, what wasn’t—became a testament to why we write at all. I’ve truly become fascinated by the idea of sharing with the world little pieces of ourselves from the naked perspective of whatever it is that forces you to take the final step toward the top of your little hill in the hope that what then surrounds us huddles close to a smoldering pit. Inside, fiction and reality blur. And if you can get there, then you surely take a look around and allow yourself to wonder what it would be like if your whole life existed in the new make-believe world. 

And then you run with full force toward that feeling. 

Macro outlines might not work for me because the devilish stuff is down in the muck—I had to escape the feeling of getting bogged down by the big picture, of the macro outline micromanaging my muse. And piece by piece I had a handful of elements to come back to for each person, which helped me let go of the Venn diagram circling like a crooked vulture around, say, which devil Cairo Martínez would dance with. 

At the end of each section I wrote a sentence or two—sometimes a full paragraph—about what might happen next. Almost as often, this would need to be repeated (and edited) on the Notes app on my phone or an email Draft-to-self. And over time, my character sketches became the skeleton of a working-in-progress outline. I found great comfort in being constantly uncomfortable because it imprinted The Next Thing on my subconscious and the music never stopped. That incessant momentum made me believe that if it had, someone would’ve been there to pull out another chair in the form of a bad joke, life-affirming statement, treasonous act, or all of the above—and they had more than 1500 miles of open road on which to do so. 

In the end—which is only the end because this version of the story says so—it works something like an accordion, the ending playing off the beginning as the whole thing folds in on itself to play a complete series of acts while also leaving room to riff after reading—right into the sequels to come. 

For me, for my process, that’s as pure as it gets. 

I’m excited to share more and learn from ya’ll in this forum.