Make Writing Good Better

The Hemingway app has one job: strike out all the various superfluous, unnecessarily complicated, and verbose prose from a piece of writing. The appeal of using an algorithm-as-an-editor certainly caught the attention of blogs and media outlets, even as its success threatens to make yet another newspaper job redundant.

Readability – both in terms of its aesthetic presentation as well as the actual content – has been under-appreciated in the age of the internet, with pithy memes and half-sentences and a handful of characters making up the vast majority of writing online. Even with longer form content in blogs and articles, the economics of online writing has sided decisively with sheer volume over quality. Even on a personal level, I can attest to spending more of my time trying to put out more posts than meticulously editing the ones I have drafted1.

To the authors’ credit, the software is free and open. But given that it’s claiming to make people better writers, that’s an open invite for real-world validations. The most amusing one I saw ran Hemingway’s own writing through the app, and the results that came back were mixed at best, hilariously hypocritical at worst. It seems like some of the classics are in need of a smattering of clarity.

Except that, well, that’s how great prose is written sometimes. I’m reminded of some advice I gave a friend a few years back on his graduate school enrollment essay: he was asking for tips to make his writing more lively, and in studying all the rules on grammar and sentence structure and essay layouts, he did all the right things but still came across as generic and cliche. My take on it was that rigid structure helps establish a base quality, but greatness comes from knowingly breaking the rules. It applies to college essays as much as it does to simple blog posts.

For effect.

For drama.


Just to establish a tone of unpredictability.


  1. The Yoast WordPress SEO plugin provides some helpful analysis on every post I write, with a Flesch Reading Ease score estimating the complexity of prose. I routinely score in 40s, and unsurprisingly do not score highly on Hemingway either.

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