Becoming a Better Freelance Writer–Lessons Learned from Failure

I started off with freelancing in college to pay the bills. The only jobs around campus paid too little, demanded too much. Since I had a minor in English literature, it was only fitting that I moonlight as a freelance writer (which also stoked my ambitions to become an author).

This is my story of how I became a freelance writer and of what I learned in the process.

Lowered Expectations

When I started out, I was confident, arrogant even, completely sure of success, ready to straddle the world of freelancing with firmly planted feet, dazzle clients and fellow-freelancers alike. Of course, all these illusions were shattered within a week as I realized the going rates for freelancers without experience ran in the low single figures per article, and that finding (and keeping) clients was harder than playing pool with a pencil.

Humbled, I eventually settled for a low paying job writing keyword rich, SEO articles for an internet marketer. It was a far cry from delusions of month long paid assignments for Rolling Stone, but it got the ball rolling nonetheless. After a week of effort, I finally saw a $100 payment sitting in my PayPal account, which did wonders for my motivation. I was soon combing through listings, trying to catch more lucrative gigs.

Building a Business

Within two months, I had a solid roster of clients who would sometimes even refer their friends to me. Work streamed in, and I could now charge at least in the low double digits per article. Visions of grandeur were rekindled–paid articles for New Yorker dripping with grit and character, gigs for Vanity Fair, hobnobbing with celebrities for People!

Another Run-In with Reality

Three months later, however, I was rolling in fatigue, not hundred dollar bills. The work was too tedious, didn’t pay nearly as much as I’d hoped, and finding more clients was becoming more and more difficult. Worse, no matter what I did, I couldn’t get better paying clients. Exhausted, I took a week long break, concentrated on college, and let emails from clients go unanswered. Within ten days, I lost most of my clients, and was back to square one.

(Hard) Lessons Learned

I neglected my budding freelancing career for a month before I ventured on to job boards again. This time, however, instead of blindly jumping in with naïve assumptions of success, I took the time to analyze my first failure. Here’s what I concluded:

  1. Loyalty Matters. My clients dumped me within a week of unanswered emails because I hadn’t taken the time to build loyalty. A loyal client will stick to you, cajole you, coax you and wait for weeks before flicking on the kill switch. I was, to them, merely a writer, not a core part of their business. They could fire me, and they would just as soon find another writer to fill the spot left behind.
  2. Personality Matters. After analyzing the dozens of articles I’d written in the past six months, it was apparent why I couldn’t find better paying jobs: no personality. My writing was dry (and not in a good way), generic, lacking the width or the depth that gets top freelancers those hundred dollar projects. Each article opened with an over-the-counter introduction. The verbs were listless, and the adjectives lacked punch. Each article blended into the other, no matter the topic.
  3. Be a Writer. I was a writer, not a content provider. There is a world of difference between the two (more on this later).
  4. Where You Look for Work Counts. I was looking in the wrong places for the right jobs. Hit a job board frequented by internet marketers looking for cheap articles and it’s unlikely you’ll find gigs that will pay you what you’re worth.

Applying the Lessons Learned

In my second inning as a freelancer I decided to do things a little differently. Some of these changes were:

  1. Establish Relationships. From a drone that shot off template-like emails to clients, I started working to develop relationships. Connecting outside of email, through Skype, LinkedIn or even Facebook helps to put a face and a personality behind an impersonal email exchange. Suddenly, for my clients, I wasn’t ‘Joe Writer’ anymore, but a living, breathing human who was extra polite in his Skype chats, and cheerful in his emails. Clients think thrice before firing someone like that (not that I’m advocating being late or unpunctual).
  2. First Impressions Count. As a freelancer, your greatest assets are your clients. Bludgeon them with awesomeness from the very first assignment they send you. You want them to tell their friends, “Hey Fred, I found a great, enthusiastic, talented freelance writer. Maybe you should give him a try,” and not “Hey Fred, here’s a lousy, crabby writer with no personality who is hardly ever punctual. Give him a try, but don’t pay him too much.”
  3. Pump in Some Personality. Nobody enjoys reading a dry, dead article by a no-name writer. Bring in a little zest of your own, pump in some personality, use words that you enjoy in a writing style that stands out. This is the number one reason why writers fail to jump to a higher pay grade: better publications simply don’t want a cookie cutter writer. They want someone whose writing jumps out, gets tweeted, liked on Facebook, and forwarded via email. Think of TechCrunch’s Mike Arrington. His voice had a certain ‘swagger’ (as Fred Wilson defined it) that attracted and retained an audience. It’ll take time to develop a unique voice, but once you do, stick to it, and push it into every article that you write.
  4. Step Beyond Writing. Recently, a client contacted me for a dozen blog posts in the green tech space. After a couple of emails back and forth, I realized that this client knew very little about marketing, and even less about how content works online. I invited him to Skype and had an hour long chat with him. I learned about his objectives, the breadth of his knowledge and the future vision for the site. Instead of merely offering a dozen articles, I offered him a complete content strategy: what kind of articles to write, how to write them, and what voice to write them in. We ended up brainstorming a bunch of article ideas, and a couple of days later, I was in charge of the site’s entire content strategy with two other writers working under my wings. It pays to go the extra step and work with a client on things that don’t fall under his area of expertise. As a writer, you have to constantly find opportunities that leverage your skills. If you come across a client who doesn’t quite know what he is doing, take the time to help him out. Formulate a content strategy tailored to his needs. It never really hurts to ask a few questions.

What’s Your Story?

I’ve shared my story (and what I learned). What’s yours?