How I Write

April 6, 20238 min read

How a person can overthink something with purpose.

I’m not sure when a person is allowed to declare themself a writer.

Is it enough that you write in a journal, or in long emails, or blog posts, or some kind of learning materials? What if you write for yourself so you can turn things in your mind and try to better understand them? Or are you a writer when you’ve actually published enough somethings to make a career of it?

If it’s enough for you, I’m going to call myself a writer because I need to write.

If I spoke to you, the words would tumble out like oranges from a ripped bag. That’s how it feels when I try to claw my way to the end of a sentence I started, or discuss something without excessively long pauses. When I write to you, though, I can take time with my words and chase after the precision and intention I wish I had speaking.

I love hearing how professional writers describe their work, because I’m convinced they’re actually describing how they think—writing being a product of a well-honed thought process. I’ve stolen a lot of ideas that resemble this one:

Clear thinking becomes clear writing; one can’t exist without the other.
— William Zinsser, On Writing Well

I’m going through some sort of season in my life where I’ve decided to take my ideas seriously and see what happens. I’m suddenly more concerned about following ideas and developing them and expressing them, even though I’m not new to writing.

Someone asked how I approach writing and I offered a detailed, specific response that came naturally.

This is how I write.


The idea of starting is funny because I usually don’t know when it happens.

The writing I’m proudest of comes from observing details over a long period of time and finding connections between them. The commitment to forming words comes with assignment (documentation blurb, client copy), a realization that I have something to say, or having something I’d like to better understand by writing about it. Many ideas I need (for technical or any kind of writing) will be there long before I know I’ll be writing something. I know you’re aware of this and I don’t mean to sound insulting pointing it out, but to me it’s a subtle and essential ingredient. I can’t write you a great piece about skydiving because I don’t know anything about skydiving.

I’m annoyed when people don’t use their turn signals driving, interested how people behave with others when there isn’t an audience, and fascinated by the social signals we project online, and I’ve known for a few years there’s something here but I don’t know how to connect it all yet.

I wanted to connect Gatsby hype and the California Gold Rush and got a blog post introduction out of it.

This thing erupted suddenly after someone’s Mastodon post jolted me into seeing a few fuzzy, overlapping ideas about art and AI and humanity with some clarity.1

Really Starting

Once I commit to organizing words, I make a big mess and spend the majority of the time editing it into a form I can live with. Shaping clay.

For all sizes of things—focused bits of documentation and longer technical and personal pieces—I’ll usually outline first (GitHub or Linear issue, todo item, bulleted list, mind map, etc.) so I have a roadmap to guide me through the mess that comes next. I pretend to myself that it’ll all be clear and orderly.

Then I jump between bursts of sloppy, impassioned writing, and waves of revision and restructuring and sharpening.

The first one is hard because I’m self-critical to a fault, and the second is great fun.


Over and over, I look for language to strengthen and gaps to fill. When I’m done being annoyed by my own writing, I imagine a specific friend or acquaintance reading it from the start and see if that exposes any missed transitions or flabby ideas. Sometimes I spend weeks or months sitting with it when it doesn’t feel ready, rushing to improve an idea or work in a dry joke I think of while I’m washing dishes or something. Because of this nonstop revision, I take forever to write and I’ll often end up moving and re-shaping things like some people do with index cards.

When I feel stuck, sometimes I’ll rewrite a thing from scratch (blog post, section, etc.) one or more times, then pick the pieces I like most as if it’s a big gross merge commit.2 If I’m bored with what I wrote, I’ll do it over to be funny or tell a story and see what I can pull together into a cohesive form.

At this very moment, for example, I have an unfinished post about 3D printing I’ve been kicking around for a year. There are tons of how-to articles on 3D printing, and I want to tell a story about the experience: what it feels like, sounds like, what dynamics I’ve had to get comfortable with. What it makes me think about. It’s also my experience and tells you about me. But it kind of explains and kind of rambles and I get bored toward the end and bet you would too. I’ll probably get there, but I’m not happy with it yet.

I’m happy once it has a flow that stands up to my internal critic and the people I imagine reading.

I’m guided by warm, practical advice from William Zinsser and whatever writing I happen to be enamored with at the time. Currently that’s long form pieces I find on Longreads and the achingly beautiful stories of Brian Doyle and the playful things he does with words.

Defending Overthinking

I’ve stolen justification for this obsessive approach from others.

Bauhaus-modeled design school shaped my thinking about cohesiveness and refinement, but my biggest revelation came from hearing an American radio producer named Ira Glass. I used to listen regularly to a radio show he did (and still does) and was fascinated by how moving and meticulous and perfect it was. I listened to someone interview him at one point and they asked how he achieved this level of production value. He said there’s no secret: he spends endless amounts of time editing and revising because he has to for himself. That a show is never done but it has to air. Jerry Seinfeld said something similar about his career successes. (You’re probably thinking of Seinfeld but I’m thinking about the brilliant simplicity of Comedians in Cars Getting Coffee.)

Nearly Finishing

I ask for whatever feedback I can from real (and not imagined!) people and am grateful for any amount of scrutiny.3 I share as many revisions as they’re willing to entertain.

It will not be surprising, then, that once it’s in near-final form (CMS entry, page layouts, front end preview, etc.) I’ll go over it several times again to see if the final visual format makes any demands. I recently wrote an article for a colleague and shifted it a bit when I saw how it looked and felt on his site. I adjusted the tone in some places and broke some lines up so they could read better in that format. I do the same thing with my own blog posts that I write in a text editor; once I see them on the page, I tend to play with things a little.

And then, for the rare thing I actually publish, I do this re-reading in waves and still catch typos. Most of the time, if someone has a comment about it I’ll re-read with them in mind and see how it holds up.

Never Finishing

If I actually committed to being a professional writer I would be forced to find a more steady process. Hopefully I’ll look back on this post uncomfortably as I learn and improve.

I wandered into Critique Circle out of curiosity and highly recommend poking around if you’re interested in getting feedback on your writing. It can be pretty much any genre, and many choose to share their work with relative anonymity. It’s been fun to offer feedback, useful and encouraging to receive it, and unexpectedly instructive to see how other people have responded to the same things I’ve read.

I get regular inspiration from the things people choose to write, and my hope is that I can find something to say, in a way that only I could say it, that might matter to someone else.


  1. I tried to mimic Cat Valente’s articulate passion and Brian Doyle’s lyricism and optimism. 

  2. If you’re not a developer, a merge commit is when you’ve got to manually look at conflicting code side by side and decide how to resolve differences without ruining everything. It can be a challenge even when you’re the jerk that wrote the parts on both sides! 

  3. Yes, you can take that as a direct challenge. I hope we can be civil, but if you have any sort of thought about something I’ve written I’m ready to hear it! 

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