Diary of a slow, fast writer

Will Kelly
3 min readJul 9, 2023


Photo by Jess Bailey on Unsplash

I often describe myself as a slow, fast writer, but that doesn’t mean I’m not productive. I may not hit those high word counts like other writers, but I’m still doing the job in my way.

Being thrust back into freelancing full-time again has gotten me thinking more about my composing process and how I write since I need to remain in a near-constant state of productivity.

Here’s a look at how I navigate life as a slow, fast writer:

1. Iteration is my copilot

I’m not a perfectionist. What I pride myself on Is that I can iterate on content and crank out one or two extra drafts when it takes some other writers to complete a first draft. However, my propensity to iterate sometimes slows me down.

I would like to know if I could write the final copy in one sitting and if I would enjoy writing as much as I do. Starting with a blank page still brings me joy. Revising with track changes feels liberating sometimes, even.

2. Plan early and thinking ahead is one of my saving graces

Managing a whole bunch of 800–1000 word articles is like managing small projects. There’s the lingering temptation to do little formal planning. That’s how I ran things in the early days leading me to get burned a few times. Now I use an editorial checklist template in Todoist to manage my article writing workflows. The checklist has been with me since article writing was a side hustle to now as a full-time freelancer. It’ll also follow me back again when I return to full-time employment.

3. Start writing my own playbooks

I’ve been gun-shy in the past to document how I do things personally. It felt unnecessary until writing during the pandemic. All the isolation made me feel like I was missing a step with writing projects. The fact that I’ve been on a near-constant job hunt for full-time work, pitching freelance projects for the past two years, and having to explain how I work repeatedly is also driving me to start creating these playbooks.

Notion is serving as the home for my first playbook. I’m starting it using Miro diagrams and then iterating on the text.

4. Personal writing projects remain the first casualty of billable work.

I was an English major in college and won awards for writing poetry and short fiction. It’s been challenging during my career to balance writing for fun and billable work. Take this post you’re reading now; it took me over a month from idea to final publishing. That was because of article writing deadlines. The end of the quarter for TechTarget gave me some extra time to catch back up on some personal writing, including this post.

While I’ve experimented with Generative AI to streamline the composing process for some of my personal writing projects, it felt wrong. There’s no personality in Generative AI drafts, so it doesn’t feel like my work.

All this leaves me with way too many ideas for blog and Medium posts than I would ever have time to write even if I won the lottery or married wealthy. I’m OK with that.

5. Engage my Dyslexic Thinking early and often

Thanks to the work of Made by Dyslexia, I’ve been focusing on best using my Dyslexic Thinking as an edge. In case you’re not familiar with the term, Dictionary.com defines it as:

An approach to problem-solving, assessing information, and learning, often used by people with Dyslexia, that involves pattern recognition, spatial reasoning, lateral thinking, and interpersonal communication.

I kept my Dyslexia an open secret for most of my adult life. Now I see I need to exercise it as a strength and a differentiator. When it comes down to it, it’s been part of my success as a freelance writer during the pitching process.

Will Kelly is a writer and keen observer of the IT industry. Medium is his personal publishing platform. He has worked as a technical writer, technical marketing manager, product marketer, and freelance technology writer. Will has written about the cloud, DevOps, and enterprise mobility, most recently for TechTarget. Follow him on Twitter: @willkelly.