Jonathan Cutrell

Getting Past Writer’s Block: Break the Rules


One thing I’ve been able to do in my writing career is… well, write. Perhaps the better way to describe this is to say that I have a knack for not getting stuck in writer’s block.

I didn’t realize this was a skill until a coworker recently asked me about my writing process, and inquired into how I get from zero to finished without many hitches.

(He should see how many unfinished articles I have in my Svbtle queue, but nonetheless…)

I started explaining my process. Usually, my ideas come from a conversation (as an example, see the article you are currently reading). Next, I write what I’m thinking.

I don’t marinate on the idea for very long. I don’t try to fully construct my argument. I don’t map out the sections. I just write, unadulterated and usually raw.

Most of the time I make many references to things that others don’t understand. I’ll make some strange comparisons and synthesize fairly obscure meaning out of thin air. But I write.

Then, I go back, check my headings, rewrite the things that don’t make sense, and if something good comes out? Publish. Iterate.

The truth of the matter is, so many people get caught up on their inability to write cohesively. To write something compelling. We all think a major amount of research is necessary, probably because we’ve been poisoned by academia to believe our own thought isn’t legitimate - that we can only speak from anecdote.

But no one is grading these papers. People read anecdotes. You don’t need to formulate the perfect argument every time you sit down to write. Instead, you absolutely, without fail, must tap into some kind of core human emotion inside of you, and let that emotion inform the flow of your words. Perhaps this is why my best writing comes from conversational topics. My emotions are peaked in conversation, and things that move my emotions are often likely to also move others.

There’s no pride in that necessarily - we are human. Emotions are powerful, and starting your writing in emotion is perfectly viable.

Of course, that doesn’t mean you shouldn’t edit. And edit again. It also doesn’t mean you can rely solely on emotional appeal to prove your argument.

This isn’t about whether or not emotion is a viable alternative to logic or reason, as it certainly isn’t. Emotion guides you towards intuition. When you tap into emotion, words become fluid, and writer’s block seems to stay at bay. You stop second guessing and examining the idea - practices which kill your output - and instead you focus on the fact that you have something to say. Ultimately, if you are a writer, having something to say is the most important skill you can achieve.

Think of your writing as an architect thinks about a new building plan. If you first approach your writing by constructing the technical requirements, toiling over the debate-style point-by-point inspection, you are effectively trying to build the schematics for a building first. Instead, you should cast your vision for the building by painting what you feel it should be. The details of that approximation are fleshed out in editing phase.

Write without the rules in mind. Contradict yourself. Commit every logical fallacy in the book. Allowing your human tendencies to be present in the first phase of writing is incredibly important.

Why does this work?

I strongly believe the reason this works is because “writing” isn’t one discernible practice. Instead, it is a collection of practices that should be treated as separate, distinct skills that are combined into a singular super-skill.

Writing is:

  • Output: This is what we’re talking about in this article, for the most part. This is where people end up getting “writer’s block”, and is absolutely the primary, most essential part of the writing process.
  • Research: Research occurs in so many different ways. For me, research isn’t purely academic. It’s coincidence, experience, and consumption all in one. Research performs two roles as it relates to your writing: informing and validating.
  • Editing: Editing occurs throughout the process. We do both simple editing (wherein we correct our “alright"s to "all right"s), as well as complex editing (wherein entire sections are nixed, and the necessity for new sections arises). Editing is informed both by your output and research, but will also affect your output and research significantly.

If you can do the three of these things well, I believe you can write well. What’s more, it takes a massive amount of fluid output to be able to effectively research and edit. If you are experiencing writer’s block, ask yourself these questions:

  • Am I trying to over-validate my idea?
  • Have I hit a roadblock because I’ve lost my argument along the way?
  • Should I start fresh, or should I shift modes into editing to re-align myself on the emotional track?
  • Am I trying to fast-forward to a post-output stage?
  • Am I actually invested in the idea I’m writing about? Where did the idea come from, and do I care enough to keep writing about it?
  • Do I believe in my own writing enough to be authoritative on the subject I’ve started authoring?
  • Am I just trying to avoid a longer editing process by writing it "right the first time”?

Answering these questions should help you find a shift in thought that will put you back in the output stage. Never write without authority. Don’t trade emotion for logic. Write with your feelings. Paint your buildings first.

Written by Jonathan Cutrell, Engineering Manager at Guild Education and podcast host at Developer Tea. You can follow him on Twitter at @jcutrell.