The Nonwriter's Guide to Writing A Lot

Toxic Preconditions (And How to Fight Them)

Image by Author, via MidJourney

Author’s Note: This is a post from my archives, written for Medium in June of 2024. I’m going to slowly start porting many of my relevant posts from Medium, editing them and adapting them for Substack.

Some quick background for this: I only started writing in 2019. Prior to that, I was perpetually blocked, unable to produced writing in a disciplined way for more than a month at a time. Then, one day, I started. But of course there’s more to the story than that, and this was my attempt to capture the essence of it and explain it to others. I’m putting it here for the Substack community. Do you struggle to write? These ideas may not solve your problem, but please think on them. Do you write a lot, but today you happen to be blocked? Again, these may not be perfectly tailored to help you break through, but I hope you find some wisdom in them.

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Are You Stuck?

How do you go from dreaming about writing, to actually writing?

The simplest answer is “just write,” of course. But that’s unsatisfying. It’s like saying that the way to stop smoking is to “just quit.” It ignores the covert mental war hidden behind discipline. People who ask how to write are actually asking how to fight this war. Saying “just write” is like saying “LOL. Just win.”

I struggled with writing for decades. As a student, I wrote prolifically when deadlines threatened to chop my ‘A’ off, but disciplined writing eluded me. Instead I collected notebooks, carrying one with me everywhere, filled with sentence fragments, to-do lists, and doodles — and I started a good half-dozen projects, none of which lasted two months. I dreamed. A lot.

In 2019 I changed. I started writing daily, and whoa hell did it upend my life. My notebooks filled with ideas that I upcycled into essays. I developed the unholy ability to finish term papers two weeks in advance. My writing powered me through drafts of academic articles, scripts for lectures, and well over a hundred articles, most written using a fountain pen.

I feel happy saying that. It’s not often that I can just state what I’ve accomplished. I’m proud of it, not in a narcissistic way, but in the pleasantly amazed way that comes from looking at something you’ve built that once felt impossible.

This article has been a long time coming, because I want to tell you how I was able to start doing that. My hope is that it will help you as well.

The Problem: Toxic Preconditions

Let’s start with an observation: You are already a prolific writer.

I once tried conducting a study on the works of Mahatma Gandhi. I had to reconsider after discovering that Gandhi’s writings spanned 98 volumes, each over 400 pages long.

That seems prodigious, but if you look at your own correspondence — every email, text, and post, every tweet you’ve cast into the soulless void that is Twitter — you will likely find that you have written more, by this point in your life, than Gandhi’s entire life’s work. You’re an internet user. A netizen; you write more text as an afterthought each day than most people pre-1980 did on purpose.

For some reason, though, the things that matter to you — the novel you’ve been dreaming of, the family history you want to write — are different. They’re blocked from your natural prolific-ness. Why?

The answer is anxiety, but stick with me; I’m not going to give you a bunch of woo-woo bullshit about how you need to be braver. I prefer to discuss mechanics, so here’s the mechanics.

Anxiety intrudes into writing in two ways:

1. Complex writing is intrinsically anxiety producing. According to psychology, a main cause of anxiety is goal conflict. Clashing goals create discomfort.
   
   Writing is full of clashing goals. When you write you plan, research, compose and edit all at once. These tasks clash, producing a steady stream of high-friction moments and tricky problems. Each conflict is draining, and each conflict produces a desire to leave, forcing you to exert effort just to keep working.

2. Concern over how our writing will be received also produces anxiety, especially when the audience is important. Picture an email to a colleague and compare it with an email to your boss — one is an afterthought; the second is a struggle. Writing grows much more difficult when the outcome matters.

Mixing both types of anxiety gums everything up by adding an extra layer of impression management to the writing process — an impossible layer, since you’re managing the impressions not of people, but of the cruelest phantoms your mind can summon. Even if you can push through, it makes writing a painful, high-friction activity.

The friction leads to more problems. Once writing has become a high-friction activity we start balancing the struggle of writing against the benefit. Thinking about writing this way warps it into something unsustainable. We form a series of toxic preconditions — misguided beliefs about what writing must be, in order to be “worth it.” I’m going to focus on three here. You can think of them as the non-writer’s preconditions for writing:

1. Writing should be worthwhile. Since writing is a high-cost activity we decide it should only be used on high-reward projects.

2. Writing should be done once. Since writing is a struggle there’s diminishing value to doing anything that isn’t the project.

3. Writing should be done right. Further, since writing is a struggle, there’s no reason to circle back to edit it and make it better. One and done. Who in their right mind would sign up for a second beating?

Most problems I have seen with writing stem from these preconditions. There are methods to make writing much easier, but if you decide that all your writing must be important, done once, and done right, all of those other helpful methods are off the table before you even start.

Instead of writing in a sustainable way, most people ensnared by these preconditions focus on motivation-boosting strategies to help them push through the friction. They procrastinate until fear of the deadline propels them through projects. They chase self-help advice searching for an awe-buzz, riding the euphoria to motivate themselves to write, until the buzz fades and they have to search for the next. Or they wait until circumstances give them room to collect their determination, which rarely happens. But they never find a permanent solution.

Undoing Toxic Preconditions

First, some bad news: You will (likely) never be able to build a sustainable writing habit by motivating yourself — using fear, or excitement, or discipline — to handle high-friction writing. Motivation fades, and once it fades the friction will take over again and you will stop.

Next, good news: A much more promising route forward is to find out how to reduce the friction. The straightforward way to do this is to fight your toxic preconditions. You don’t do this through therapy. Instead, you do it by acting contrary to your toxic preconditions: Start a new practice that directly contradicts the precondition, sticking to it until your old belief unravels in the face of new evidence.

Let’s talk about what this looks like in practice.

Undoing Toxic Precondition #1 (Writing Should be Worthwhile)

The key to overcoming this precondition is recalibrating what you consider worthwhile. An example: Since 2019 I’ve produced over 400,000 words of published text (including 200,000 words for blogging platforms like Medium and Substack). But that’s only about a third of what I’ve written. The rest is invisible. Why? Because it’s dirt.

“Dirt” doesn’t mean bad compositions. It means most of my writing is not composition. It’s random thoughts, or notes to myself, or explorations into my interests. My rule is to listen to my brain — if it wants to write nothing but to-do lists for two weeks, I listen to it.

Why? Well, you need dirt to grow plants. A farmer I admire once wrote that 90% of his job was dirt management. Manage the dirt well and the plants grow themselves. Writing grows, too: Create a fertile field of exploration, fun, and inanity, and the rest will follow. Wuthering Heights, one of the greatest novels ever written in English, grew out of the Brontë sisters playing the Victorian equivalent of a tabletop RPG.

What does dirt management look like? The simplest version is, write whatever you find fun or useful regardless of its public value — especially if it’s adjacent to the type of writing you eventually want to produce. Here are two examples from my own writing:

• Meta-Writing. This refers to any writing that externalizes my thoughts so that I can sift through them. At least half of my writing is meta-writing. It’s refreshingly mundane; I write goals, plans, tasks, observations, and daydreams. I write to purge noise when my brain is too loud and to make noise when my brain is too quiet. It’s too mundane to be a journal. But it’s vital to me.
  
  Meta-writing helps me think. It helps me hobble along when my brain is full of static, which is often. I have found it to be deeply invaluable in constructing ideas, exploring my soul, and just working through what I am going to do each day.
  
  Meta-writing also builds momentum. On bad days meta-writing keeps me disciplined, giving me a reason to put pen to paper. As such, my private meta-writing is probably the greatest aid to producing public writing that I have. My journals are full of pages that start with what I planned to eat during the day and ended with a fresh idea, or an outline for a prospective article.
  
  You’d be amazed at how often “worthless” writing transforms, mid-sentence, into something worthwhile. The muse visits those who make a space for her.

• Praxis. This refers to your knowledge base — the raw material you draw from when writing. Most people build their praxis haphazardly. Their material is kept mainly inside their head and they only add to it when they are researching a term paper.
  
  However, if you are committed to writing regularly, one of the most pleasant writing activities you can do is to build your praxis deliberately by researching and writing about your interests. Write to learn.
  
  I currently have a few pages in my journal devoted to the nineteen phases of ice, and another few devoted to counterfeiting in early colonial America. Pieces of information like these get upcycled into my articles and other work regularly, and surprisingly fast. Build your praxis and new ideas suggest themselves as you go. A great way to start as a writer is to begin with the discipline of observe and record, with no intention of sharing. Once you’ve built momentum you can start writing publishable material.

Undoing Toxic Precondition #2 (Writing Should be Done Once)

The key to overcoming this precondition is to make writing a multi-pass process. Visual art is multi-pass: artists start with a rough sketch that captures the general idea for their composition. Then they go through and do a more detailed sketch, turning the rough lines into recognizable features, fiddling with proportions and placement until each element is arranged as they want. Then comes line art, followed by detail work, and finally coloring, which could entail several passes of its own.

Now imagine an artist who starts with a one-centimeter square in the top left corner of a blank page, insisting it should be perfect — every detail of line and color, flawlessly in place — before moving on to the next centimeter. This sounds ridiculous, because how could the artist hold the whole picture in their head without the aid of their sketches and guidelines?

But… isn’t that what you’re doing to yourself when you demand that your writing should be done only once? It’s like trying to solve a puzzle while keeping all of the pieces in the box, rooting around for the right piece by feeling alone.

Multi-pass writing is simpler, more fun, and more sustainable. You can do what works for you, but here are two techniques I use regularly:

• Outlining. I used to avoid outlining. Whenever I tried, I wound up deviating from my outline, so it felt like a wasted step. Later, I recognized this is natural. New angles spring from an outline in the same way that new possibilities for artwork spring from a sketch. Even when you deviate, outlining is useful because it releases mental tension. Getting the big-scale composition on paper stops it from interfering with your other writing tasks. Outlining is a classic for a reason; it works.

• Write a Splat Draft. Alternatively, you can write your draft in one long, stream-of-thought rant. I call these “splat drafts” — you get everything in your head out on the page at once, without regard for form (hence the “splat”). Then you treat it as the raw material for a second, proper draft. Think of it as the act of dumping the puzzle pieces out on the table so you can sift through them and see what fits together. If you have trouble relaxing your inner editor, free online tools (like The Most Dangerous Writing App) can help.

Undoing Toxic Precondition #3 (Writing Should be Done Right)

The key to overcoming this precondition is to force yourself to write incorrectly. This doesn’t mean abandoning quality: it means turning quality into its own step, separate from composition.

The precondition that writing should be “right” isn’t really about quality, after all. It’s about immediate quality. Demanding quality as you compose causes the ‘writing’ and ‘editing’ subtasks of a project to interfere with each other in an agonizing way. It’s writer’s block, pure and simple.

I work with academic researchers. The average academic paper is a monstrous eight-thousand word amalgamation of statistical analyses, literature review, and technical jargon. Most researchers I know who can produce academic papers regularly have accepted that an article takes at least three drafts before it is finished.

Drafting distributes the complexity of writing across episodes, making technical writing much easier — whenever you hit an intractable problem you can simply move on, focus on what you can write, and allow two of the writer’s most potent allies — time and sleep — to resolve the problem for you.

It’s not just academic writing, though. The principle behind drafting is that complex and useful thoughts are grown like plants. They’re not squeezed from your brain like toothpaste from a tube. Put a thought on paper, tend to it correctly, and it will grow into a better thought. Or, as I’ve told students; first write badly, then write goodly. Here are a couple ways to do this:

• Deliberate Incorrectness. Having trouble with your internal editor? Here’s a delightful way to get rid of it: Deliberately commit to writing badly. You can do this many ways. One of my professors insisted that his graduate students send their first draft of an academic article to him in an email. You can think of it as a form of strategic un-professionalism. Clive Thompson, a prolific writer, suggests a version of this as well.
  
  But you can take it further; if you’re paralyzed by your internal editor, try adopting a persona so ridiculous that you can’t edit it. When I was paralyzed as an undergraduate I would write a “stoner draft” — my goal was to write a draft that sounded like it was dictated into a cell phone by a surf rat hopped up on ganja. There was no way to write an A+ paper in the middle of all the whoa dude and lol righteous, so my internal editor gave up cleaning until later, which was the goal.
  
  Pick whatever voice suits you. Write in the most artless way you can imagine. Write like Gollum, from Lord of the Rings, or like Jar Jar Binks from Star Wars. The goal is to dissociate your ideas from the voice saying them, so that you can focus on the ideas alone.

• Overwriting. The original draft of this piece was 6000 words long. The current version is under 3000. It takes time to cut out excess material, but once you get into the swing of it, it becomes pleasurable. It sharpens your writing and frees you to write as your mind dictates without chopping material on the fly.
  
  Don’t be afraid to use fifty words where ten will do. Often, if you start by writing expansively, you can condense your writing in later phrases, until each sentence bears the weight of three or four. It’s easier to do when you have all of your big ideas on the page, instead of trimming them down as you go.

Closing Thoughts

Becoming a prolific writer is not about motivation or intensity. It’s about redefining ‘writing’ so it becomes a fun, edifying, sustainable activity.

Once you start getting the words out on the page you can work with them and upcycle them into the type of high-quality writing you’ve always dreamed about presenting to others. But for those of you who are just starting? Write for joy.

Write for fun. Write for your own self-edification. Write as messily as your brain will allow you to — to explore, to clarify your soul, to grow your ideas or to think through the mundanity of your day. Do it as often as you can, until all of those toxic expectations have been leeched out and you can see writing for what it is — just words, on paper, that you can use for anything you want.

Committing to that practice is a life-changer. Once you’ve moved from the illusion that writing is about composition to an understanding that writing is just about putting your brain on paper where you can make friends with it, the articles and the books and the poems and all that will work themselves out. It’s worked with me. I think it will work for you. Drop me a comment if you have questions or requests.

Image by Author, vis MidJourney