I Fired Myself to Keep My Freelance Goals on Track

dominic vaiana freelance writer

By Dominic Vaiana, Freelance Writer


A Promising Lead

Last month, I reached the one-year milestone in my freelance writing career. As many will understand, the first few months were frustrating, exhausting, and barely profitable. I fought for table scraps every week. $75 for long-form SEO articles? Sure. $50 to rewrite copy for an entire website? Sign me up. 

Needless to say, a younger me couldn’t have comprehended the idea of cutting ties with a global B2B brand that put a sizable chunk of money on the table. So, what prompted the exit? And how can other writers know when to walk away from their clients?

I have ideas—but first, some context.

How I Got the Job

In the spring of 2019, I decided to step up my freelance career: I wanted bigger clients, more money, and most importantly, I wanted to write stuff that people actually care about. I called my friend and podcast savant Jay Acunzo and gave him a run-down of what I was looking for. Within a day, Jay tweeted something along the lines of, “A talented young writer is looking for his next opportunity. Who wants to get in touch with him?”

Among the emails I received was an introduction to the editor-in-chief of a global B2B brand used by companies such as Netflix, Uber, and Amazon. He was looking for someone to contribute long-form articles to the brand’s publication, which is seen by more than two million people monthly.

After a couple of interviews with their team to ensure I wasn’t a serial killer, I got my first assignment: a 2,000-word feature story about a world-famous consultant who held prestigious positions at Google and Facebook.

I had it made—or so I thought.

Then the Red Flags

Before I wrote a single word for this brand, I had a hunch that I was in over my head. I had more than enough writing experience, but I knew next to nothing about the industry and even less about what my audience—digital product designers—wanted or needed to hear. I suppressed that thought, telling myself that raw talent could compensate for a lack of familiarity.

I was quickly proven wrong.

My editors emphasized on multiple occasions that they loved my writing style: my verbiage, narratives, and cadence. However, the same problem kept arising: I wasn’t coming up with enough tangible takeaways for the audience—key insights that readers needed to improve their careers in this specific industry.

This seemed logical, but I didn’t have the slightest clue as to what those takeaways were supposed to be. For example, if I wrote about a useful resource for entry-level digital product designers, I’d get feedback such as “What specific problems do entry-level designers face? What practical steps can they take to apply this resource?”

No wonder most of their existing writers were also digital product designers.

I felt deflated, not because my writing was heavily edited or because the work was challenging, but because I was fundamentally disconnected from my audience. I felt like a boxer stepping into an MMA octagon every time I opened a Google Doc. 

Initially, I thought my saving grace would be the paychecks. The brand was my second-highest paying client and my highest-paying client per article. But after some number crunching, it was obvious that the work wasn’t as profitable as I originally thought. 

Each article went through several rounds of edits since I could never quite grasp the concept from the get-go. Between research, interviews, and several rounds of edits, I could only produce one to two articles per month, at most. On the other hand, I knew I could write four articles for DUDE Products or College Info Geek in the time it took to finish one for this brand.

Let’s do some back-of-the-napkin math here (I also keep a full-time job, so time is always at a premium.)

  • The big brand paid $500 for a 1,500-word feature story that took more than a month to complete.

  • My other clients paid, on average, $250 for articles ranging from 300 to 1,000 words. I could write these in an afternoon with one round of minor edits.

  • Based on these calculations, the big brand was paying me $31 per hour, the other clients, $62.50.

Bottom line: A few afternoons of relatively easy writing could be twice as profitable as a month’s worth of interviews, edits, and arduous writing.

I was left with two options: Sink dozens of unpaid hours into studying this industry and its audience, or cut my losses and move on.

The Decision

I was in the midst of editing my third article for the brand, staring at a heavily marked-up Google Doc, when I decided to send the following email, which has been edited for confidentiality.

After considering [brand]’s editorial standards, I don't think I'm going to be a good fit moving forward. I don't feel confident writing about an industry I'm not familiar with and I don't quite understand what [occupation] want/need to improve their careers. 

I think both of these gaps weaken my writing. As I mentioned, I'll make the edits for the [topic] article, but I think it's best if we part ways afterwards. Please know that I’m truly grateful to have been given an opportunity to work with such a prestigious brand.

I hope you understand. Let me know if you have any questions or concerns.

The fact that I felt a wave of relief after pressing “send” is enough evidence to know that I made the correct decision. But as I reflect, I can identify three specific reasons I had to pull the trigger:

  1. I’m adamant about pursuing work that gives me energy, work that I genuinely look forward to when I wake up in the morning. This work made me feel dull and lost.

  2. For the first time in a year as a freelancer, I found myself frequently thinking: Who else could I write for? instead of How can I grow with this client?

  3. I knew I could earn more money by growing existing clients and/or leveraging this brand's reputation for future clients.

These points aren’t unique to me. Every writer should consider them to get perspective and clarify the direction he or she wants to take.

But What If …

I ran through dozens of what-ifs before I pulled the plug on this job:

  • What if the editor bad-mouths me to other brands?

  • What if I can’t recoup my losses as easily as I thought?

  • What if I never get an opportunity like this again?

But in the month since I sent that email, things have gone quite well. I expanded my scope of work with one client and used the extra time to find a new one. Here’s the advice I’d give to anybody stuck in the same scenario:

  1. Remain calm. It’s an important decision, but not life-or-death.

  2. Cutting ties and being honest yields more respect than the "fake it till you make it" approach. If someone guilts you into work you don’t enjoy, they’re not worth your time anyway. 

  3. Always consider the opportunity cost. Your ego isn’t nearly as valuable as your sanity (or your bank account).

  4. If you're not emotionally engaged in your writing, no amount of work ethic or doggedness will improve your work.

  5. Dabbling in different industries is almost always more valuable than becoming a narrow specialist—especially if you’re young. If you’re not convinced, I recommend Range by David Epstein.

I don’t have this freelancing thing figured out by any means. But I do know that leaving money on the table—even for a short while—is intimidating. It goes against everything freelancers are told. But sometimes, the only way to get ahead is to quit.

Black and White

Dominic Vaiana, Writer, Marketer, Strategist

Dominic Vaiana is a writer, creative strategist, and bibliophile. You can find his articles and book recommendations at DominicV.net.