Your Start in Freelancing

What’s on the iPod: Coffee Cups by Langhorne Slim and The Law

Good day yesterday. I have two article assignments due this month, plus some newsletter work for another client, so I’m busy. Feels good to be back to a semi-regular work schedule.

I was over at Jake Poinier’s Dr. Freelance blog where Jake is talking about that first freelance paycheck. It’s not just the thrill of getting that first assignment, but it’s the check. That check validates you in ways you never thought possible. It’s when you cash that first check that you can no longer deny your calling — you’re a freelance writer.

Jake asked on his blog, but I’m going to ask on mine, too. What was your start in freelancing? Feel free to leave your answer over on Jake’s blog, too. His idea, so give him some comment love. But I wanted to relate my own beginnings in freelancing, for even the most, well, unusual beginnings can be great places to start.

It was 1988. The local newspaper — the now defunct Pittsburgh Press — was holding a contest. I entered. It was my first time entering, so I didn’t expect much. Fortunately, my own expectations were exceeded. I won first prize. That distinction came with a trophy, a photo of me in the paper, and a check.

Dare I say it? The contest I’d won — The Pittsburgh Press Sunday Magazine Bad Writing Contest.

Yes, you too can have an ironic start to a career.

How the contest worked: The editors gave entrants one sentence. From there, you make the story your own. Here’s that sentence:

Like an expensive sports car, fine-tuned and well-built, Portia was sleek, shapely and gorgeous, her red jumpsuit moulding her body, which was as warm as the seatcovers in July, her hair as dark as new tires, her eyes flashing like bright hubcaps, and her lips as dewy as the beads of fresh rain on the hood; she was a woman driven–fueled by a single accelerant — and she needed a man, a man who wouldn’t shift from his views, a man to steer her along the right road; a man like Alf Romeo.


That one pathetic sentence was the basis for my entry, which continued like this:

   Alf Romeo was a rock; nay, a steel-belted dynamo. He wore his radial strength like a space-age polymer that could withstand 52 consecutive car washes. He had high-octance good looks; His skin glistened like fine Corinthian leather, his amber eyes burned like fog lights against his metallic red hair. He was bumper-to-bumper sex appeal, and Portia held the key to his ignition.
   Alf radiated when with Portia. His heart accelerated and his valves rapped with unleaded passion for her. She alone fogged his thoughts and sparked in him new life. Yet, when it came to returninghis passion, Portia left Alf exhausted. He towed to her every whim, but she shut him down like fuel line freeze-up. Portia had him in her clutches, and she shifted his gears with fuel-injected fire. His senses were muffled by her chassis, which possessed a trunk that overheated many an engine. Though his diesel efforts remained unrewarded, Alf was a Die Hard. He plugged away, sparked by his desire, yet hydroplaning in his attempts to lubricate her Ziebarted heart. But alas, Portia wanted freedom — Delco Freedom — for she longed to live on the racer’s edge, longed to feel the Heartbeat of America, longed to drink the V8 of life.
   The more Portia slipped from under his hubs, the more the big lug spun his rims for her, until he was too far gone to jack his wheels up under himself again. He began parking his frame at the local pit stops, the intermittent belts lubing his dented emotions, but giving him a spare tire and waxing the look of his spreading fenders. She had dashed his hopes, and it had taken a toll on Alf. No longer did his eyes shine with halogen brightness, and his skin had aged like cracked vinyl. Portia’s cruelty had grilled Alf, and his classic beauty was wrecked, never more to be salvaged.

Alas, we can’t all be Thoreau. But that made me $50 richer. Woo.

So I’ve shared my auspicious, somewhat embarrassing beginnings into freelancing. Your turn.

What was your first sale? How much did it net you? How have you built on that (or overcome it, as in my case)?