On Writing

Dec 15, 2017 19:25 · 1091 words · 6 minutes read Writing Meta

Written communication has always been somewhat difficult for me personally. I work much better in a verbal environment where I can clarify and revise my thoughts live. Body language and tone help convey intent in a way that’s mostly lost over text, and you can confirm understanding simply by asking. Text is more static and enduring. When you write something down, it’s hard to know who is going to read it, how they will interpret it, or even if it has any value to your audience.

Producing written content is made more difficult by the editing process. Sometimes you can write a sentence or paragraph that you believe encapsulates a thought, and then skip right over editing it. After all if you understand it already what’s the point of continuing to analyze the same section repeatedly. Other sections suffer from too much editing. It’s easy to fall into the trap of writing and re-writing a few paragraphs because the content doesn’t quite capture the essence of your idea or the wording seems imprecise or unclear.

Lastly, and especially for this platform, it’s sometimes difficult to know what to write about. In the context of a conversation everything is decided ahead of time. Meetings are called for a topic or someone walks over to your desk with a question. Writing documentation, an email, or a blog post like this one leaves the context more open ended. Questions arise like “Will this topic be valuable for someone to read about?” Or “Does this cover everything they might want to know about this topic?”

Writing posts for this blog has been, and continues to be extremely useful for me as a platform for improving my writing. In accordance with that I wanted to share some of the lessons I’ve learned in my time creating content for this site.

Overcoming resistance

One of my favorite books is The War of Art by Pressfield. His model for lack of motivation is a force called “Resistance” that permeates and radiates off of any kind of creative work. Having written a fair number of posts now, I can tell you that this is a real idea and very powerful. Sitting down to write is one of the most challenging aspects of my week. Sometimes the problem is I can’t think of what to write about. Other times I get stuck in an editing loop where I’m running over the same passage repeatedly, feeling as though it’s not clear enough or good enough to publish.

It was especially bad in the first few weeks when I was just getting started writing. I had never seriously maintained a blog before this one. I would wind up getting to the weekend and absolutely dreading having to start working on the post. The number one thing that helped me though was ultimately to just sit down, pick a topic, and force myself to get started. Once I’m actually typing, I start enjoying the process of trying to clarify my thoughts and organize them. Especially after I have a couple big chunks written, the resistance fades away and continuing to write gets easier and easier. This is similar to static and dynamic friction. It’s hard to get a car moving by pushing it but once you have it going it’s not so bad.

Choosing a topic

This is somewhat specific to working in the blog format but might be applicable in other formats as well. For a while choosing a topic was just as difficult for me as actually writing about it. I would spend half an hour thinking about different things I could publish and come to the conclusion that I just didn’t have anything to say. Similar to overcoming resistance in writing, I would ultimately just choose the first thing that came to mind on Saturday or Sunday morning since all my posts have a hard deadline of Sunday evening.

Eventually I started to be better prepared. Now I maintain a pool of 4 or 5 different topics that I can write about. When I get some idle time I tend to think about what I’ve done in the last week or things I’ve experienced that might be somewhat unique. Those ideas end up on a whiteboard and eventually some of them get added to the pool. Generating the initial pool was difficult and took a few weeks, but afterwards I noticed that ideas come to me more frequently and keeping the pool stocked with decent ideas is not as hard as it once was. This is similar to a technique Hunt talks about in Pragmatic Thinking and Learning. The theory being that when you try to think of ideas and capture them, you will naturally have more ideas1.

Being OK with failure

The last concept – and this is true of any type of practice – is that you have to sometimes be ok with doing a mediocre job. Being of an engineering mindset, I’m dissatisfied with something that I don’t consider my best work. Writing is one of the more difficult things that I’ve learned how to do, and that’s partially because I read a lot. I inevitably end up comparing my writing to books (which have been through professional editing) or articles written by professional writers or skilled writers. That comparison is unfair to myself, but it’s done at an almost unconscious level.

Comparing oneself to a master is actually a great way to improve your work. But constantly berating yourself for not producing perfect prose every time doesn’t help anyone. Having a hard deadline for when the post goes out, and making everything public has definitely helped. By the time the deadline is looming on Sunday afternoon, I’ve done all I can. I have no choice but to ship whatever content I’ve created after the last round of editing and try to improve again next week. Publishing something that I know isn’t exactly perfect week after week really lessens the sting as well. Having 99 perfectly written posts and one really bad one might be embarrassing, but having 100 posts where each one is better than the last should make anyone proud

If any of the tips above resonate with you, or you’re just looking to improve your writing in general, I can’t recommend starting a blog enough. Even if nobody reads anything you write, the experience of producing written content on a schedule and forcing yourself to write is worth it.


  1. Hunt, Andrew. Pragmatic thinking and learning: refactor your wetware. Pragmatic Bookshelf, 2010. pg 52-54 [return]