Writing | Freelancing | Success Stories
How I Earned $1,000+ Per Article Every Week for a Year
The build-up to one of my most profitable writing engagements
Many of the popular articles here on Medium are quite meta.
Authors share and discuss their writing journey toward successfully breaking into curation, getting accepted into the bigger publications, and earning from the platform. Some also share tips and advice on how to optimize the writing workflow for success.
I thought to share a story of my own, in which articles I wrote earned at least $1,000 each in a week’s time for at least a year.
A caveat, though: This does not necessarily involve the Medium platform, although I can say that being on Medium did somehow help. Sorry — I hope my title was not misleading.
Another caveat: Due to NDAs, I cannot disclose details that will violate those agreements.
Working for an enterprise audience
In the mid-2010s, I did freelance work with a boutique PR firm that had a major technology company as a client. We did enterprise case studies, as well as other marketing assets.
Being enterprise-driven, the client could afford to pay a lot of money for the campaigns. That meant that for each case study, I got paid anywhere from $600 to $1,000 depending on the coverage and the other marketing assets included.
That’s it. That’s the short answer to how I ended up commanding at least $1,000 per article: Get a big client that pays well.
However, the story does not end there, and it certainly is not that simple.
The buildup
I have been writing professionally since 2002, and I started freelancing in 2006. Back then, I accepted writing jobs that paid $2 to $5 per short article. That was hardly enough to make ends meet, but I relied on volume to thrive.
You can expect that quality suffered due to volume and cost, but that was during the time content farms were starting to flood the web with SEO-targeted articles. I thrived for a while, but that business model soon fizzled out. Even content-driven startups with billion-dollar valuations went out of business.
But I got the writing experience and exposure. With some connections, I was also sought out to launch and manage a digital magazine focusing on tech. This got me introduced to technology publications online.
I also became a paid contributor to an enterprise-focused technology publication.
In 2012, I joined the Medium platform when it was first launched. I was even able to import years of archives from WordPress (dating back to 2004), and I still have a couple of domains running under the now-grandfathered Medium hosting platform.
It was also in 2012 when I was hired full-time as a country editor for a technology startup platform. That got me into contact with startup founders, investors, development teams, media practitioners, and other professionals in the industry.
It was due to some of these connections that I then got referrals for the PR copywriting gig that paid a thousand bucks per article.
$1,000 Per article can be hard work
Here on Medium, there is a science and art to the thousand-dollar article. It’s a combination of topic, quality, style, audience, and marketing — some of it can be attributed to timing and even luck.
Some authors will admit to having articles written in half-hour as being their most popular and profitable pieces. For some, it will take much more effort.
For me, the thousand-dollar article involved a lot of work, but it also came with benefits.
Writing enterprise case studies took a few steps:
- The account manager scheduled a teleconference with C-suite executives.
- I researched the company and prepared targeted questions to bring out a good narrative.
- I met or teleconferenced with these CEOs, CTOs, CMOs, corporate vice presidents, etc., for a one-hour interview.
- I transcribed recordings and highlighted the best quotes and stories.
- I wrote the case study driven by narrative, metrics, and impact.
- Depending on the client requirements, I also produced other assets including executive summaries, tweets, and text for social shares. There were times I had to produce or edit scripts for a video case study.
Client work involved deadlines, so there was time pressure to consider. I had to balance this with other clients that also needed attention. So, it was on wash, rinse, repeat cycle. But that also meant money rolling in on a predictable basis.
The benefit here was that I got some exposure with these enterprise executives. I was able to gain a lot of insights into how their teams and companies worked and how their culture made an impact on their product. This has influenced my writing style to date.
There’s a lesson here somewhere
There are three things I learned from this experience.
1. Always have multiple income streams
The PR gig lasted for a year or so, but as such projects go, it had to wind down at some point. During that time, I also had other clients and projects (paying at least $150 per article — perhaps another story).
To date, I still have writing projects, and I have writing assistants to help me with some of the nitty-gritty. Having multiple projects enables me to experiment, tweak, and optimize for best results.
2. Accomplishment does not come in an instant
I can attribute my relatively high-paying copywriting work to a build-up of experience, contacts, and serendipity. You don’t gain a prospective client’s trust if you don’t have already have a body of work to show and a few great testimonials from common contacts.
I can say that my years of learning and experience paid off. My published articles became my writing portfolio.
Familiarity with the enterprise market and to tech startups also meant I had built up knowledge about the industry. It’s not easy to write when you do not have in-depth experience or at least some exposure.
I am still learning a lot, especially with reader-based monetization. I am currently exploring the Medium Partner Program. While I have not met with success yet (eight years on the platform and none of my articles have ever been curated), I am hoping to get there.
3. Keep in contact
Most of my colleagues also moved on to other projects after our PR engagement. Some who stayed on still sent me some occasional work for smaller clients. Some who worked with other publications became good referrals for other client and contract work.
This is a creative industry, and even when some aspects of writing and production now involve AI, people still matter in this business.
The takeaway
There are different paths to success. While you may not necessarily succeed in one thing, the buildup can lead to other opportunities. Be open to these opportunities. Be mindful of the lessons you learn along the way. Keep connected to the people you meet along the way.
As a publishing and monetization platform, Medium is certainly a different monster compared to an enterprise or tech startup audience. I am hopeful and confident that I can apply the lessons I learned along the way in also achieving some success here.






