Taking the Plunge into Freelance Writing: How it Worked for Me and Can Work for You

My friends who were perched higher in the tree later told me that, when I fell, it reminded them of the opening scene from Cliffhanger. They watched helplessly from above as I plummeted toward the ground in slow motion, letting out a prolonged shout of surprise that was drawn out like a foghorn, and then there was a terrific snap as I hit the ground and everything leapt back into normal speed. As everyone swung down from the tree, I looked over to find that the bone in my upper arm was jutting out at an impossible angle—a broom-handle trying to poke its way out of a bag of skin. Then came the ambulance, and the emergency room, and a slew of nurses and doctors asking what I had been doing in a tree in the first place, and all of the sudden I was an unemployed bartender.

I suppose that I could have carried on my bar-keeping duties with one arm, but to be perfectly honest, I just wouldn’t do it anymore. The drudgery of it all—cleaning up after drunks and negotiating punch-ups on a nightly basis, pandering for tips, squealing bachelorette parties…This severely damaged arm business seemed to be my way out, if only I could get the unemployment insurance to come through.

My first claim was rejected as you have to be able to seek work in order to get on the dole, and I was considered incapable of seeking work in my field of experience. I appealed citing my writing degree as grounds to gain employment within the realm of words, and some kind-hearted judge took pity, understanding that while it would be impossible for me to lug kegs around and jockey a bar with a single arm, I could still type, if a bit slowly.

Thus I entered the quixotic world of professional freelance writing. With a substandard weekly governmental check and one good arm, the endeavor began as it seems to for most writers—with an almost certain outcome of failure.

All of this occurred less than three years ago. Since then, I have written for dozens of outlets both print and online, served as a senior editor for a popular music publication, and have been paid to participate in literally thousands of nonsensical writing projects the purpose of which I will never know. Today I live in Granada, Spain, where I function as the Regional Director for an English newspaper. And there is always more freelance work pouring in, so fast that I have neither the time nor inclination to do it all.

I haven’t laid out my resume like this in order to tout my accomplishments. I’ve done it because there are too many people who possess a passion and talent for writing but have allowed themselves to be convinced that it’s a hopeless profession. They’re told that newspapers and magazines are dying out, that no one reads books anymore, and that Twitter has reduced everyone’s attention span to 140 characters, so why don’t they just go out and get a degree in something practical? Like communications?

Admittedly, I spent years putting off my venture into writing due to similar concerns (and general laziness). But today I and many of my colleagues stand as examples that the ability to put one word after another can still lead to a financially stable and sometimes even successful future.

While many professional writers grumble that the industry is being brought down by amateurs who are willing to work for next to nothing or free, the simple fact is that each of us has to start somewhere and that they too were once amateurs. It takes a lengthy resume to obtain the higher paying jobs, so early on whatever you can get you should take.

I was lucky, as I knew that I could depend on unemployment carrying me for a while, so working for free was a viable option. (Note to people who subscribe to the idea that “unemployment is not a career opportunity”: Please pay attention and learn something.) For those who are interested in going into writing but have to hold down a job at the same time, the vast majority of freelance work is performed on a telecommunication basis and can be crafted to fit your schedule.

My first unpaid gig was, in fact, the only I have ever worked that involved going into an office, as an intern for a magazine that dealt with issues relating to business sustainability. While this felt a long way off from Rolling Stone Magazine, it did give me some much-needed practical experience. Producing and editing articles, conducting interviews, meeting deadlines, and liaising between a publication and outside entities are all indispensable to acting as a broad and flexible freelancer.

Once my internship ended, I volunteered my work to a number of small, local publications. Not only did they provide me with the opportunity to build my portfolio, I also got the chance to meet and interview a wide variety of strange and interesting people from all walks of life—strippers, bar owners, musicians, tattoo artists, CEOs, filmmakers, authors—many of whom acted as useful contacts later on once I was getting paid for my work.

Building a network of writers, various professionals, and other sources is important throughout a wordsmith’s career, but it is most essential early on. These are the people who—if you’ve made a positive impression and shown your dedication to break into the field—will often provide you with your first paying gigs.

Once you have a reasonable resume, preferably with a few solid writing samples and links to published material, it is time to start looking for paying clients. This may be one of the most difficult aspects of launching your career as, to the uninitiated, Craigslist seems to be the only job-hunting source, and the writing section of Craigslist is generally filled with non-paying, portfolio building gigs.

The Internet is rife with a number of other job-board options that are specifically tailored to freelancers, such as Odesk, Elance, Freelanced.com, and Guru. To use these sites, you first have to sign up, then build a profile. Generally there are a number of membership packages, and there’s always a free option. Paying for a more expansive package has its benefits, but when you first start out you are generally good to go with the basic deal.

It can be tricky to build an effective profile, but it is important to make yours stand out. Potential clients will use them to judge your professionalism and the quality of your work. These profiles usually show your resume, a photo, the amount of jobs and money you’ve acquired through the website, past client ratings and comments, and a self-description. Write a description that comes off as genuine, confident, and indicates the breadth of your skills. The wider range of work you seem capable of performing, the more jobs you will acquire.

When choosing a photo, consider carefully what niche you’re trying to get into. If you want to go into academic writing, use a picture that shows you standing in front of a bookshelf perhaps. Or if you’re interested in travel writing, post an adventure shot or one of you standing on top of a pyramid or whatever.

Early on, you’ll want to take whatever you can get—writing resumes and cover letters, product descriptions, website content—whatever it takes to get positive client ratings and build your profile. Those positive ratings and comments go a long way, so make sure that you meet your deadlines and turn in well-edited copy. As your profile comes to reflect the quality of your work, it becomes increasingly easy to work your way into the specific niche of your choice. And once you’ve proven your ability to consistently produce outstanding content, you’ll no longer have apply to clients—they will seek you out and past clients will become repeat clients (and usually pay increasingly more per job).

There are basically three ways payment is established: per project, per word, or per hour. The first paying gig I ever landed was—ahem—writing descriptions of pornography at a rate of half a cent per word. So for every thousand words I wrote, I received five dollars. This is the rock bottom for freelancing.

Have you ever wondered where those little blurbs below each wank-video come from? Yeah, that’s me, and people like me. Where a college degree will take you these days. Money well borrowed, and never, ever paid back.

I spent hours upon hours watching videos of people caught up in brutal and often heinous acts that I—a veteran of the foul and disreputable—could not have dreamt up in a nightmare. And at the end of each week as payment for witnessing these wide-ranging perversions, I would receive a check for twenty-five or thirty bucks. But, as it was under the table and my unemployment checks alone certainly did not keep rent paid, food in my stomach, and beer in the fridge, I couldn’t complain much. It beat working a real job.

It all went on the resume. With a bit of gentle word-massaging, “Porno descriptions” became “Product descriptions”, and right about the time my unemployment ran out I began producing content for non-sleaze related companies.

Eventually my various freelancing profiles began to look pretty reputable, and they—coupled with some of the more interesting work I had done pro-bono—made me increasingly capable of applying to projects I actually wanted to be a part of. Long-form articles about just about everything—booze, music, fiction, romance, history, literature, and too many others to list.

This is a great step forward in the career of a freelancer, because not only are you writing about the things you truly want to, but with each article your voice became more concise, and your pieces more tight. As the catalog of links to the various articles you’ve written grows, you can enjoy an increasing confidence that you will nail down any job applied for. Suddenly you find clients bidding on you instead of the other way around.

This is about the time I began to write travel articles. A client found me through Elance and asked me if I had done any traveling. I had studied in Paris and throughout Spain during part of my schooling, so I began producing an endless number of pieces about both places. More and more travel companies began contacting me wanting my work. My portfolio expanded, and I paid my rent without borrowing from my friends for the first time in nearly a year.

An idea struck me—the more places I visited, the more articles I could produce, and the more money I would make. My travels would pay for themselves.

Basically on a whim, I along with my girlfriend (who, incidentally, began her freelance career less than three months ago and is already making around $400 per week) decided to move to Granada, Spain, and I began emailing my travel pieces to all of the English magazines and newspapers in the country asking if they needed contributors. Many were interested, but most didn’t pay (if you haven’t seen the news, Spain’s economy isn’t doing so well). Then I received one reply saying that she wasn’t looking for contributors, but was interested in launching a new branch in Granada. Did I think that was something I could handle?

Why, sure. Of course I can handle it. That’s all being a freelance writer is—making things up as you go along.

That was just over one month ago. Today, I am writing this from my balcony in Granada. Anytime I feel like it, I can visit the castle that is a ten minute walk away. There is a flood of potential work constantly filling the inbox of my email, and if I don’t feel like taking on a job, I don’t.

There is a reason that the word “free” is an integral part of “freelance”. There are no bosses, no rules, no obligations. There is also no certainty, and your success or failure depends entirely on your own willingness to motivate yourself, try new things, and take risks.

But without risk, there is no adventure and no reward. The endeavor to build my career and work for myself has set me on a journey that three years ago was unimaginable, and there is a wide industry of writers out there who would cheers the sentiment. Sometimes the work is fascinating, and often it is rather droll, but I marvel always that one can get paid for the mere act of stringing words together.

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