Eight Lessons I Learned From Hiring a Writing Coach

(Credit: Nguyen Thu Hoai)

(Credit: Nguyen Thu Hoai)

The best athletes in the world have personal trainers: LeBron James, Serena Williams, Megan Rapinoe. I knew that to be the best, I needed to hire a writing coach to take me to the next level.

As a species, we have a monopoly on collective knowledge. So engaging with a mentor or a coach is one of the best ways to become smarter. A good friend referred me to his writing coach, who lives outside the Cleveland region. Now I value a good referral, but I also value relationships — and we've got plenty of expertise in this region. In Cleveland, relationships remain key — over the course of the pandemic, and long after.

I wanted to become an even better writer simply to see where it would take me. I enlisted the help of Randal Doane at Cadence Editorial Services. (He works with clients in medtech and biotech, and he has a side hustle contributing to Harper's.) Randal's based on the west side, and his knowledge of the region and some of its key players allowed us to talk at a high level about things well beyond split infinitives and paragraph breaks. He is also knowledgeable about a range of topics, which is apparently what happens when you have a Ph.D.

How did it work?

To begin, our process entailed:

  • my delivery via Google Docs of essays to Randal on Monday and Wednesday by 11 a.m.

  • a Zoom chat at 3 p.m. those days, which included line-by-line discussions of my draft, with a focus on pop, voice and formatting

  • work on my social media voice, and in particular Twitter

Before connecting with Randal, I published nine essays a month: eight for my newsletter and one for Crain's Cleveland Business. In that period, I learned quickly that quantity doesn't equal quality.

Key tips

We covered, of course, the obvious things. Make verbs active. Use the historical present. Put subheads to work, because some readers will simply scan your article. "Be honest about your own attention limits," Randal also advised. "If it takes you 20 minutes to get into a writing head space, don't schedule a 30 minute writing session. You're just building frustration into your process." Randal also taught me how to split quotes and put the speaker's name in the middle.

I'd be lying if I told you I'm on a schedule, but it's definitely getting better. Typically, I'd write from 10 p.m. to 1 a.m. (Yes, I'm a night owl. It works for me. Per Randal's suggestion, I wrote this essay on a Monday morning. A huge accomplishment for me!)

Next, on Randal's recommendation, I downloaded the Hemingway app. This app helps you make your writing more succinct. If you want to be a better writer, download it.

Writing isn't only about words. It's about appearance, too. So what's the best way to engage readers in the attention economy? I started crafting multiple headlines and subheads and using bold words strategically. I also aim to ensure that every sentence delivers value. With my essays on branding and digital platforms, I aim to deliver reader-friendly, thought-provoking content every time.

Once I finished my first draft, I'd read it aloud. What a difference that makes. "Your ear will pick up things your eye scans past," Randal noted. Awkward phrasing, subject-verb disagreement, and run-on sentences: You name it, I wrote it, and now my ear knows better. In my defense: My mom served as my proofreader for ages, so I was pretty lazy about proofreading.

Finally, I'd send it to Randal. His edit focused on the Cs of writing: clarity, concision and cadence. We'd connect by phone and Google Docs and, on an unmarked copy of the essay, he would introduce his suggestions one by one. Every time Randal dropped a knowledge bomb, I scooped it up, defused it, and either applied it right then or filed it away for future engagement.

So what did the finished product look like?

The results

Right away, I saw how my writing improved, and my readers took notice, too. "These pieces are getting better and better," one reader wrote. "I find myself wanting more though. Ever thought about bringing them up to 750-1000 words instead of what seems like 450-650?" I think a big part of it was sentence length. With Randal's help, I trimmed median sentence length by 27% and still increased the variety of sentence lengths by 12%.

Wow! Not only was I enjoying the writing more, my readers wanted me to write longer pieces. My list of subscribers kept growing, too. In the month and a half I worked with Randal, my newsletter list increased by 49%. My open rate is solid, too, and 170 new people signed up to read my writing twice a week.

But the biggest accomplishment was from my mom. The self-described "perfectionist" was always supportive of my work, but definitely critical. As a proofreader in her past life, she was obsessed with finding the mistakes. By the end of my coaching boot camp with Randal, she complimented me on how much my writing had improved.

More than just words on the page

Our work entailed more than writing. It included work on my personal brand. Randal kept asking: Who is Ari Lewis? Why does he write? Who is his audience? What do they need from him?

Today, I'm building my niche in the attention economy. Every week I'm proud to share close to 800 words across my platform. It's fun to go back and review previous essays to see the difference in the thinking and the writing.

Another key thing I learned is the importance of brevity. I know I have plenty of room for improvement. Still, I'm putting in the hours and enjoying the process. Hiring a coach made a huge difference.

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