How I Landed My First Gig: A Cautionary Tale

Freelancing was supposed to be easy. No bosses, no boring work (unless you want to get paid) and no unreasonable deadlines (Ha!). When I decided to take the plunge into full-time freelance writing, I had a few fairly unrealistic expectations. In my head, high paying jobs without any expectations were just going to fall into my lap. I’d complete them from home and then dollar bills would appear in my checking account.

After two months of rejection and abject poverty, I had a much-needed reality check. As it turns out, freelancing can actually be more work than that cushy 9 to 5 we all love to lament. Not only do you have to work to meet and balance the unrealistic needs of multiple clients, most of them make you work overtime just to earn that privilege. You have to hunt down jobs that fit your skill set, and then you have to sell yourself.

When I was starting out I had a razor-thin portfolio, zero impressive bylines and a resume lighter than most college undergrads’. I came out swinging for the fences, sending pitches to national magazines and short stories to the New Yorker. Most didn’t even care enough to send a proper rejection letter. With my ego and savings account slowly depleting, I began lowering my expectations.

I set up profiles on Freelancing websites like Guru and Elance, both of which proved equally fruitless. I clipped classified ads from the back of local newspapers to no avail. With my unpaid bills reaching critical mass, I carefully lowered myself onto what I considered the bottom wrung of the job-hunting ladder: Craigslist.

In that first week of true desperation I must’ve responded to over 100 Craigslist ads. Many posters wanted to see samples online, so I wrote articles for unpaid sites like the Yahoo! Contributor Network and CNN’s iReport. Now I had something to point to when clients asked to see links. Eventually I got a phone call from an editor at a trade magazine based in Reseda, Calif. He was looking for someone to write weekly news items for their e-newsletter. I came in for an interview and in a couple of days I had my first regular client.

I was officially the writer responsible for a national trade magazine’s weekly newsletter. Fortunately for my career, the editor in chief liked my writing and before the month was out I had my first feature assignment–a 2,000 word print byline.

Was writing landscape and green industry news for a trade audience at $10/hour my ideal assignment? Can’t say that it was. But that assignment was the springboard that launched my career. I started to accumulate links and bylines that impressed other prospective clients. My name became easily Google-able and my income crept up proportionally.

Now I’m actually in a position to turn down clients who can’t pay my rate or expect too much in too little time. I’m the master of my own universe, but I haven’t forgotten where I started. From time to time, when my workload is feeling light, I still browse the classifieds on Craigslist. – Zachary Lisabeth





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