I write a lot on The Internet. I have a blog for solopreneurs/freelancers. I have a website of tutorials. I have a newsletter. And I have a personal blog. (On top of all of that, I write for clients.)
I’m writing at least one long-form piece of content every weekday. And while there are similarities in how I structure my writing time and process, each publication is unique. Each audience is unique. Even the platforms are unique: this publication is on Substack, my blogs are on Ghost, and my newsletter is on Kit (more about that here).
As a writer, I’m fascinated by the writing habits of other writers. I’ve devoured the Daily Rituals books by Mason Currey, where he dives into the rituals of creatives. I eagerly read Anne Helen Peterson’s article How I Write Culture Study. And I decided to capture my process for Work. Better.
Here’s what goes into the typical essay.
It starts with an idea
Almost every essay starts as nothing more than a fleeting idea, like “the benefits of a non-linear career” or “toxic positivity” (both actual ideas I have for future issues).
Ideas can come from social media posts, articles I read, or podcasts I listen to. If I think of something, I try to capture it in the moment so I can come back to it later.
I keep track of ideas in Trello, divided into three categories: New Ideas (might be only a fragment of an idea), On Deck (where I expand on the idea), and Scheduled (where I actually put the idea on my content calendar to write it). In Trello, I’ll link any resources related to the idea, like an article.
An idea turns into an outline
Each essay has three parts: an introduction to the idea, a second section that expands on the idea or provides context, and a conclusion that either provides a contrarian view or gives my thoughts on the idea.
As I expand on an idea (On Deck), I write down every related thought I have. Usually, these are a bunch of bullet points. I might also pull direct quotes or stats from articles I’ve read to support my argument. I’ll also search Reflect, which is my knowledge management system (and also my drafting tool). Reflect syncs notes from articles I read (via Readwise) and podcasts I listen to (via Snipd). I’m searching for related ideas that I might want to incorporate into the outline.
I’ll often take my notes to ChatGPT. I have a project set up for Work. Better. and I’ll ask Chatty to organize my scant notes into a more coherent outline. Chatty will sometimes supplement with additional articles or stats for me to read (and verify).
I’ll take the outline output from ChatGPT and refine it. I’ll remove anything I don’t like. Or sometimes Chatty will include something that leads to another idea. If my outline gets too unwieldy, I’ll break it into smaller pieces and set aside parts for a future article, rather than the one I’m working on.
An outline turns into a draft
Depending on how robust my outline is, drafting is the “easy” part. I’ve already worked out what I want to say and the direction I want to go. Now I’m just pulling everything together.
Of course, there are times when my outline isn’t as good as I’d like. Then I have to spend more time researching/writing simultaneously — so the draft takes longer. I’ve also had instances where I completely change what I want to write for the week, because I want to respond to a current event. In those cases, I have less preparation time between outline and draft, so I’m also less prepared when I sit down to write.
I draft in Reflect. I have automation set up between Trello and Reflect so that, when an idea reaches the “outline” stage, a new document is created in Reflect automatically. The Reflect URL is added back to Trello, so everything is tied together.
Polishing and publishing
Once I’m done with the draft, I return to ChatGPT. I have a style guide created and attached to a Project. Within the project, I ask ChatGPT for feedback. Most of the suggestions are Not Good, but every once in a while, Chatty will suggest something I hadn’t considered or tell me to clarify something. Working without the benefit of an editor is hard, and ChatGPT is the closest I can get to a “second set of eyes” on my work.
Then I’ll load the draft into Substack and run it through Grammarly. I’ll add internal links to related articles I’ve written. All of my prior content is stored in Airtable, and I use Airtable AI to find internal links. I use the prompt:
I’m writing a new article about [insert topic]. What internal links should I include?
Airtable will return a list of links. I’ve found this to be much more accurate than asking ChatGPT to find links on my blog. ChatGPT will still hallucinate links, even with the URL to my blog provided.
Next, I’ll create an image in Midjourney. I use ChatGPT to create a Midjourney prompt based on the draft. Midjourney style codes ensure that each image has a similar look/feel. Someday, if I earn a living from my online writing, I’ll hire an illustrator to create images. But until then, it’s either Midjourney or generic images from Unsplash (and I can’t stand using the same stock photos that everyone uses).
Finally, I’ll schedule the post for publication.
Start to finish, it takes several hours for me to write each essay including research, outlining, drafting, and getting a post ready for publication.
Sharing and re-sharing
I pre-write teasers for each essay. The free editions are published on Friday or Saturday, and I share the link the following Monday. Over the weekend, I’ll add the teaser and the published link to Buffer. I’ll also download images that Substack creates to share on Instagram. I’ll share the link to Substack Notes.
Because I track all of my published content in Airtable, I’ll also re-share past essays across social media, if I think they’re worth re-sharing. I spend a lot of time putting the essays together, and I want to give them as much “life” as possible.
Post-production
A few things happen after a post publishes that I’d be remiss not to mention.
A record is added to my content library in Airtable, which is where I keep track of everything I’ve published across all platforms. It includes things like the URL, the date published, and topics covered.
A copy of the post is added to a new Google Doc in my Google Drive. That way, I always have a backup copy of the final, published post.
The post’s image is added to my Google Drive.
All three of these things happen automatically via Zapier, relying on data from the RSS feed.
Perspectives series
The one type of content that’s handled differently is my Perspectives series. For Perspectives, I either publish guest essays or interviews.
If it’s an interview, I conduct the interview via Google Meet and then edit the transcript. If it’s a guest essay, I only do light editing so that it stylistically matches my publication.
It’s important to me to share voices from other people. I think many people have work stories that they want to share. I give them a platform to do that, whether they share using their names or choose to remain anonymous.
Perspectives usually end up taking me less time. Even though I conduct an interview, editing the transcript is a lot faster than researching/writing an essay.
How the publication has changed over the years
I started this publication in October of 2021. At the time, I just sat down and wrote whatever popped into my head. I published bi-weekly. Now I publish weekly, with a few extra posts each month for paying subscribers. I interview people for my Perspectives series. It requires more planning as the publication has evolved (and also, as my life has gotten busier with more writing).
In total, I’ve published 205 articles in Work. Better. That seems like a lot when I type it out, but also... not a lot? This publication is different than my blog for freelancers/solopreneurs, which prioritizes helpful and tactical advice.
By contrast, here I explore the frustrating and often unfair parts of work. That’s also changed. I started this publication with a post about The Great Resignation. I was filled with optimism about the future of work at the time. But things have certainly gotten dark over the past few years.
The link between the two publications is that corporate life sometimes pushes people to a solopreneur life. It certainly did for me. I know there might be some overlap in the audience, but I still treat them as separate entities. This continues to be a passion project of mine.
Thank you for reading and your interest in the topics I write about.
If you want to support my work as a writer, you can buy me a coffee or subscribe to receive additional issues I publish.
Have a work story you’d like to share? Please reach out using this form. I can retell your story while protecting your identity, share a guest post, or conduct an interview.