My Playbook for Getting Paid to Write

I fell into professional writing by accident. I was coming hot off of failing the bar exam after 3 long years of law school. The first thing I did was apply for a freelance writing job on Indeed (I now believe the days of job boards are over - I’ll explain why throughout this series) for Blackdoctor . org. I didn’t realize it at the time, but it was a health and wellness website for the African American community. I had no business writing for them, but I interviewed with the editor of the website, a woman named Jade, who ultimately gave me the job.

For the next few months, I pitched random health and wellness article ideas, hoping Jade would pick a few of them per week so I could make $60 per article. I got a lot of inspiration from Healthline and would essentially try to repurpose their content in a new way. This wasn’t very sustainable for me because I wasn’t an expert in this niche.

If you can become one of the go-to people in a niche, you stand a much better chance of making money as a writer on the Internet. Think about that niche early on.

That freelance writing gig held me over until October 2020, when I eventually stopped writing for BlackDoctor and applied for another freelance writing position with LegalMatch. LegalMatch is a lawyer-client directory, matching attorneys with potential clients all across the United States. They have one of the largest legal content libraries on the web.

My initial assignment was going through and rewriting 3,000+ of their existing articles, improving them for search engine optimization (SEO) purposes. The goal was to help LegalMatch’s pages rank higher on Google Search, leading to more case referrals for LegalMatch’s attorney database.

LegalMatch became a long-term client of mine going on 5 years now. My relationship with the site’s editor is fantastic. Since starting with LegalMatch, I’ve since written over 3,000 articles and earned about $80,000 in lifetime sales.

Next, I decided to leave the Kansas City area where I had gone to law school and lived for the past 4 years to take a job as the editor of the Big Horn County News in Hardin, Montana. I was hired after several phone calls with the owner of the Yellowstone Newspaper Chain, Mr. Sullivan. He took a big risk by hiring me, a young man fresh out of school with no prior journalism experience. I packed up my little Chevy Malibu with all of my belongings and drove north overnight to Livingston, Montana. Mount Rushmore was only a 40-minute detour, so I pulled off and saw it on that cold, gray winter day.

I spent two introductory weeks to journalism in Livingston, publishing the first of my stories to the newspaper about basketball and recent winter storms. I learned about newspaper design on Adobe InDesign from Dwight, a now retired reporter and editor for the Livingston Enterprise.

After two introductory weeks to journalism, I spent 6 months in the southeastern plains of Montana in the town of Hardin on the outskirts of the Crow Indian Reservation. The Crow Indian Reservation stretches over 2.2 million acres, the largest reservation in Montana. I worked my ass off on the outskirts of the Crow Reservation. I covered everything from county politics to sports, eventually finding a short writing gig with the Billings Gazette. From there, I was hired as the editor of the Big Timber Pioneer after the Yellowstone Newspaper chain was sold to Adams Publishing.

Working in journalism as the editor of a small-town newspaper sharpened my writing skills by forcing me to write for an audience every day. I also had to edit my work, shaping my sentences in a way that made sense to the most people. I learned about storytelling, factual reporting, and the general structure of the lede: the opening line or paragraph that delivers the who, what, when, where, why, and how. It’s important to nail these so readers instantly know why the story matters and keep their eyes moving down the page.

I also learned about volume. The secret to great writing is endless repetition, especially if you’re unknown. Publishing a once-per-week newspaper forced me to write multiple stories per day. There wasn’t a ton of time to edit, so I had to learn to proofread very quickly. I learned that great storytelling starts with sheer volume.

Lesson: publish more while you’re still unproven.

Using my background in law, I also landed contract writing gigs with two legal content agencies. I landed these clients after applying on Indeed and then immediately finding the owner’s phone number and giving him a call, pitching myself. These two legal content agencies serving law firms across the US. I still create blogs and landing pages for these two agency clients today, although the nature of writing on the Internet and SEO has drastically changed.

Like many writers, I’ve also had to contend with the advent of AI in this type of writing with the release of ChatGPT in 2023, so my next post will break down how I published 3,000 paid articles and the AI strategies that now help me write my first drafts in eight minutes.