My Advice: Why You Need to Do Outlines


There is a moment in time when even the best of writers were where you sat. They hadn’t so much as written a word on a page, not yet changing the world with some of literature’s finest prose. They may have even had writer’s block, spinning a pen tirelessly as they look at a blank page and feel like they’ll never amount to anything. This is a moment we have all faced and are likely to keep returning to so long as we have the passion to write because, let’s face it, the whole profession has an interpretive quality to it that makes the starting point difficult. The best of stories maybe don’t even start with the writer typing the opening paragraph. Maybe it’s an idea later on that they branch off from.

Basically, the blank page is the great unifier. Even the best of us have had days where we look into the void and find ourselves more interested in doing chores or going for a jog. We have no desire to sit down and write a masterpiece because… what if the ideas don’t come out right? What if we’re all wasting our time and this whole thing ends up being garbage? To answer the last question, there will be days when you write garbage. But don’t see garbage as simply a blight on your career. Understand why it’s not your best and grow from there.

I have found in my personal experience that my worst work came from a lack of focus. This isn’t in any ritualistic procedure to get to the page. I am talking about when I get there. I have promised myself to spend the next two hours writing out this great magnum opus of a short story, but I haven’t committed to a premise. All I want to do is “express myself,” and it’s here that I have several different experiences.


There’s the relief you get when you can start writing and the ideas just flow. Suddenly word association kicks in and you’re finding the mind-expanding in exciting ways. I love these moments because you are rarely this focused in life. Nothing on the page existed before five seconds ago, and you don’t have time to overthink a single word choice. It’s just going to exist until the second draft begins to form things. It’s beautiful, cathartic, and the fantasy that I wish was the case every time. English teachers call these “free writes,” and you can’t appreciate them until you’re doing them for your own benefit. It’s there that the pressure’s off and only you will see how much you’re capable of.

I really wish that was the case for every time I set out to write a story because life would be a lot simpler. It continues to happen several times a year, but not every time. Things couldn’t be handed to you that simply. No writer has the ability to steal from a well of inspiration, making your muse work overtime without compensation. You just have to live with the reality that some writing is going to be a pain to contract from your brain, whether because the idea requires that much creative nimbleness or you’re just too distracted and exhausted to do it.


Being a young writer, you’re often more naïve and believe that every idea drops into your brain at just the right moment. I think of how Lil Wayne would consume “purple drink” and free-verse over beats, allowing a stream of consciousness on par with a juvenile James Joyce. It was confusing, sometimes incoherent, but his brand of being an alien made his approach this fascinating kaleidoscope into his brain. Sometimes you got “Tha Carter III” where everything landed well enough – likely because it’s collecting the best of hundreds of recordings – that it made one of the most acclaimed and successful rap records of the mid-2000s. 

Other times you get the rest of Lil Wayne. You only see his “best” because it’s pulling from hundreds of hours of recorded audio. Sure you can get the mediocre ones as free albums scattered throughout the internet, but when it came to official albums, “Tha Carter IV” suffered because his free-verse could only carry him so far. Our minds are only so malleable when we force ourselves to rely on instinct.

I never said he was smart

No man is perfect, and that is why I have become favorable of the more vanilla approach. We all like to think we can knock out a great story in one draft, but it’s hardly the case. We don’t want to spend time with our work to notice our flaws, to grow and become a more interesting writer. We just want to get it done. However, I think this discouraging behavior is because we don’t have discipline, of picturing a long game where our work grows and becomes something more interesting.

So before you write the story, I want to suggest that you start with an outline. As I’ve gotten older, I have found a value in one for a variety of reasons. For starters, my mind is unable to hold the story in form like it used to. Things begin to slide, fall off, and something great could go unnoticed altogether. That is why I have begun to do something that every English teacher has crammed down your throat. I have begun to see things as a bigger picture, and that means starting with the components.

Much like last week’s piece about deadlines, I think that the only way to tackle stories is to start on a small level. Don’t even write a sentence. Sit there, whether with a pen or in a place where inspiration strikes you. Think about what you want to write. No idea is off limits, but use your instinct to determine which one of them deserves to escape your brain. 

It doesn’t even have to be about the overall story. When I was writing “Apples & Chainsaws,” it started more as a prompt about turning 30. While I had been writing short stories for several years, I wasn’t sure if I was capable of something more. Basically, what did I have to say in novel form? I didn’t have characters, but I wanted to write a book about being in my late-20s and coming to terms with the end of an era of my life. 

I started with an idea, expanding from there into the themes that I wanted to explore. This meant a sprawling story of how I felt when looking at every facet from feeling old to depression and education. These were all things that I felt concerned about and wanted to explore them as I would. From there I began to try and shape these themes into characters that I could take on a journey. 

Sometimes freewriting works on a small level. You can look at these characters and have a clear idea of where you want to start and end them. For others, you’ll need to pull teeth to get anywhere with them. “Apples & Chainsaws” was a little bit of both. On one hand, I had personal experiences to pull from. I wanted to use specific events both personal and social to draw out bigger ideas. Having these aspects can work as building blocks to the bigger picture. 

Before you can go much further, you have to understand your characters on a personal level, thinking through scenarios that will not be in the book, but will explain their dynamic. If you can make them so personal that they’re your best friend, you maybe can get away with freewriting every now and then within your structure, allowing your brain to go into creative directions that the outline doesn’t cover. A lot of moments for me stemmed from a familiarity with every aspect of these characters and where I wanted them to go. 


I suppose the bigger question you’re asking is how much detail you put into an outline. The answer is different for every person. What I will say is that the more that you can write will benefit you. You don’t even need to use all of it. Think of it like cleaning out a storage locker. You have to move and open a few boxes to get to bigger, greater ideas. Sometimes the best comes in unexpected ways, and you just have to use your instinct as to where it should go. Even then, having the keys to the storage facility and knowing where every box is allows for your resources to be at your disposal.

It also differs based on the length of your story. If you’re writing a short story (maybe 5-20 pages), your outline doesn’t need to be more than a few words. If you know where you want to go, just go for it. I find that going any further may be difficult because accomplished writers will know how to incorporate nuance and small character moments to enhance the emotional resonance If you want to be a great writer, you have to know how to plant these ideas within your story and have it be organic. I don’t think that it can be done in free write form in a novel. Sure, you can come up with the idea during this time, but having an outline to consult will at least inform you to the consistency of the decision.

If you ask me how much is enough, I’d suggest doing this as an exercise. Write down your ideas. Form them in the order that you want to present them in. If you can look at a word and understand where that chapter is going, then you’ll be fine. I’d still suggest having more just in case, but I have often had chapters summarized as just an idea, such as opening “Apples & Chainsaws” with a wedding and a funeral. I came to the conclusion that I wanted to explore duality both in characters and moments, and that felt like the clearest way to start things. However, later chapters where the character dynamics were more complex and internal, I needed to write paragraphs to create this deeper sense of purpose. 


As I’m working on my next project (currently scheduled for a 2021 release), I am discovering my own faults in the outline phase starting to appear. I thought that I had the structure understood clearly and began to write, feeling like I understood the endgame. The issue was that after the opening 50 pages – which were the most detailed in outline form – I began to run into hurdles. I didn’t understand my characters as well as I thought, and the world began to collapse on itself. I had to go back through and rewrite my outline to enhance the story and become more acquainted with what I wanted to achieve. 

It’s one of those examples that even with an outline, we’re not forced to follow a structure. Sometimes our instincts are wrong, and we have to accept that things need to change. Depending on your quality of outline, maybe only a little needs to change. However in this instance having a vision of where things were going allowed me to course-correct small things and find smaller things that I had ignored. 

If you had to ask me, I’d say that you need to get a flexible outline together before you even start. You can only get so far without an idea of where things are going. Endless stories of mine have ended with convolution because I realized that I had no idea what I was doing. Having that outline at least will get you started, giving you more confidence to even try in the first place. To me understanding the characters on a human level is just as important as what you put into the book, creating dimension that you can latch onto. Sometimes a word is enough to make it clear. Others require so much detail that your eyes will glaze over reading it. Whatever it is, there needs to be something there. Without it, the blank page will always be scary. 

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