As an experiment, I decided to start using Hemingway to proof my blog posts and work assignments. Hemingway is a free web-based tool that catches a few common grammatical sins and rates the "readability" of your text.
My corporate writing is meant for a wide audience known for their short attention span, so making sure that my newsletters and documentation are clear and simple is a priority. Hemingway works really well in this scenario, and it's okay if the results come out a little bland.
As for my blog, the most common posts I make are book reviews meant for a general audience. If someone finds my site from a Google search, it's important that my content be accessible. That said, I do tend to make the occasional rhetorical flourish when I'm passionate about a book, and those are oftentimes my favorite posts. I'm confident that my best writing would never pass Hemingway's readability standards.
After a few days of using Hemingway for my writing, I started feeling stifled by its rules. I need all the help I can get when it comes to avoiding passive voice, but I'm not sure I think that complex sentences are such a big deal, and adverbs do have their place now and then.
Unfortunately, whenever Hemingway highlights something in my writing, my instinct is to rewrite that section obsessively until the highlight is gone. This means that I massage complex sentences until they are uniform in length and simplicity. This might make my writing easier to read, but I also think it removes a lot of what makes me unique and interesting as a writer.
When the app first launched, one of the first things people pointed out is that even Hemingway wouldn't pass all the app's rules 100% of the time. The dirty little secret of English grammar is that a lot of the rules are just suggestions to ignore whenever your writing style calls for it.
For example, I recently read You Too Can Have a Body Like Mine, which has such a high rate of adverbs per paragraph that it was clearly a conscious stylistic choice by the author. Whether that choice was successful is another question entirely.
For now, I've stopped running my day-to-day writing through Hemingway. I suppose I could always use it to check for passive voice and ignore all its other suggestions, but that would take a bit of restraint on my part.