Freelance Writing is Hard! Until You Land a Whale

Freelance Writing is Hard! Until You Land a WhalePhoto by Michael Blum on Unsplash

Earning spending money as a freelance writer is difficult, earning a living as a freelance writer, especially in the beginning, can seem impossible. It’s not.

In fact, you could make the argument that it is easier now, more than ever, to find paid writing work. There are platforms like Upwork, Fiverr, and Problogger that post thousands of freelance gigs every day. Finding work is not the issue, the issue is finding high-paying and on-going work.

I call gigs that are bothhigh-paying and on-ongoing, Whales. If you want to make a living as a freelance writer, you need to land some Whales. This is much easier said than done.

Persistence pays off

One struggle that new writers face is the simple fact that making money in freelance writing is not a quick process. You are not going to create an Upwork account, apply to a few jobs, and make a living right away. That isn’t how it works.

The reality is that writers who are earning the big bucks have been at it for years and years. Perfecting their craft and building authority and trust in their field, and delivering content that makes their clients money. As a new writer, you simply do not have these things, you will have to start small.

Building your written foundation

Before being hired for big gigs you need to have at minimum a small body of work. No one is going to pay hard-earned cash for a writer with no experience.

My foundation in writing started as it does for many, with a blog.

You see, I am a teacher, I am passionate about education and education policy and I wanted to share my thoughts with the world. So I started a personal education blog, offering tips and advice for teachers. I produced 10–15 articles, attempted to monetize them, didn’t see much traffic, and got tired of writing for such a small audience.

The blog failed.

Although the blog wasn’t successful, I did enjoy writing and researching, I just needed a better way to monetize this passion. Enter Upwork.

Find your first paid writing gig

My journey took me through Upwork. Why? Because it popped up as an option when I searched “How to make money as a writer,” in Google. I created a profile, entered my information, and was ready to go.

In my first week, I probably applied to 50 jobs from all niches. Most of these jobs were low-paying, “new to Upwork,” types of jobs. You know the type, $10 for a 1500 word post including SEO and keyword research.

I didn’t hear back from any of them.

It was time for a change of plan, this time I focused only on a niche that I was an expert in, education.

Putting “education,” into the Upwork job finder yielded a long list of jobs that were focused on schools, education, and even teaching specifically.


Or so I thought…

I applied to 10 of these gigs that were a decent fit for me, I wrote cover letters, answered interview questions, and got exactly 0 jobs.

What gives?

Looking over my Upwork profile when I realized my problem, I was so busy telling the prospective clients what I could do but I wasn’t showing them anything. They needed samples of my writing, they needed a portfolio.

But if I have never been paid to write, how could I possibly create a portfolio?

My old blog! I thought immediately.

Back on Upwork, I applied for 10 more writing jobs, this time I attached my three best blog posts from my teaching blog.


One client wanted me to write a 1500 word article, for $50, on how education technology can improve student learning.

I accepted immediately.

Leveraging your work to land a Whale

I wrote 5 articles for that education company before they ghosted Upwork, for a total of $350, of which Upwork snagged 20% (brutal, I know). Although it wasn’t a ton of cash for the amount of work, it was my first paid writing gig.

It was exciting!

Now, armed with paid work that was live on a website, with my name attached, I was ready to really start raking in the dough!

I began to apply to all education jobs that Upwork had available. The problem was that there weren’t too many opportunities, and not many making more than I already had made. So I started to branch out.

This time, I set a filter, I would only apply for jobs listed at $100 or more. Making a living on $50 per article is impossible. I figured that applying to some higher-paying gigs couldn’t hurt. I applied to more than 15 jobs, all paying between $100 and $300 per 1500 word article.

Of those 15 I heard back from just one, and it was a full month after I had applied. They sent me a direct-hire invite saying that although I wasn’t a fit for the job I applied for they would like me to write a couple of articles, at a rate of $250 per article.

The company was a direct-to-consumer insurance company that was building out a ton of content on their website. They wanted me to write some informative dental health pieces and possibly some long-form sales pieces.

This was it, my Whale had arrived at last.

The only problem with this was, I knew nothing about insurance or dental health. So, when my first article assignment came through, What is Hyperdontia, I had to hit the books. Luckily, we have Google.

I wrote the article in half a day, submitted it, and awaited their response.

It came 2 days later, they accepted my article and gave me a couple more, rinse and repeat. Now, I have been writing with this company for over a year and they just signed me on as a contracted writer making $350 per 1500 word piece. They send me 10 pieces a month for a total of $3,500. We have moved off of Upwork so I keep the full amount. They are my Whale.

Success leads to… more success

When you write on Upwork the whole Upwork community can see your past jobs and how much you have earned. They also see feedback and other metrics. This is why it is so hard to land that first Whale, but it is so critical to your long-term success.

Whether you are writing through Upwork or just pitching clients in your community you are up against fierce competition. Your potential clients care about the bottom line and they can be hesitant (rightfully so) to blow big cash on unproven talent.

This is why Upwork is such a powerful tool for beginning writers, especially writers without a degree in journalism, English, or marketing. It allows you to show your success and leverage that success into more jobs.

A positive feedback loop is a reaction that stimulates more and more of the same. In this case, getting high-paying writing jobs will increase your chances of getting more jobs just like it.

In my case, I applied for other jobs within the insurance niche simply by searching in Upwork. After applying for 5 insurance-related jobs something unusual began to happen.

I actually heard back from 4 of the 5 and had 3 who were good fits to do some content writing. These gigs were not as lucrative as my Whale, however, they still paid well at $75 per 500-word article.

It is clear, that landing the Whale gives you an advantage on a platform like Upwork, it gives you a proof of concept. Companies are willing to roll the dice on a writer who has a proven track record of producing for high-paying clients. They figure that if you are writing well enough for a competitor to use you over and over again, then it is good enough.

This is the positive feedback loop, this is the essence of earning enough money as a freelance writer to quit your day job.

Success leads to more success.

Industry matters

It is important to know that Whales exist in all niches.

However, not all niches are created equal, some are more Whale-dense than others.

As I mentioned earlier, when I first began freelance writing I was trying to stick within my professional niche. This was a struggle, almost all jobs posted were for $50 or less on Upwork. Outside of Upwork, the education niche does have some high-paying blogs but they are few and far between.

This makes complete sense when I think about it now. There is not as much money to be made in education, outside of large corporations, as there is in other niches.

If you want to catch a Whale, you need to go to where the Whales live. I am talking about your classic big-money industries where there is fierce competition for sales and clients, such as:

  • Law
  • Finance
  • Insurance
  • Healthcare
  • Travel

Each of these industries needs content written to compete with other members within their industry.

They take this very seriously. The guy who hired me as an insurance writer basically said that competing with the big-boys to land on the front page of Google essentially requires a Wikipedia-like encyclopedia of articles and resources housed within their company website.

In short, they need a ton of content in these niches.

Another thing that all of these industries have in common is that they have gigantic marketing budgets. It is nothing for them to pay you $200–$400 per article if it helps them land millions of dollars in potential sales.

These industries know what you are worth, and they are willing to pay it.

Feed the beast

Once you have landed a Whale it is so important that you keep the Whale happy, you must feed the beast.

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