The Long and Winding Road to Freelance Success

By Sheila Scarborough

When I walked past the shiny automobile oil pans stacked and displayed like a Christmas tree, I knew that my first big paid freelance writing assignment at the Gatornationals drag races would not be a total disaster. It might be a learning experience, an embarrassing moment, an opportunity to pretty much look like a moron, but not a total disaster. The merchandise tent's oil pan tree was fun and interesting and unique, and so was drag racing. I wanted to be a writer, and a great topic was all around me. I'd make it work.

Until that day, my most successful published item was an impact assessment of Navy network-centric warfare on military organizational behavior. Why not follow that up by writing about Top Fuel dragsters? A new travel writer should always start out blogging from a drag strip. It toughens the mind.

Sheesh, you're saying, I'm confused-- where'd the "travel writer" thing come from, or the Navy thing, and how did blogging or drag racing get into all of this? 

Exactly. My path to freelance success is full of roads not merely taken, but roads that I've stumbled down and fallen upon and bumbled through and wandered across. The important lesson is that I kept walking.

In my first life, I was a seagoing Navy officer for about twenty-two years. I drove ships and loved the salt-sprayed seafaring life, but it was coming to an end. The usual follow-on was a switch to corporate Dilbert Land. Trade the khaki uniform for a suit, the ship for an office, and keep the steady paycheck coming.

Also a complete soul-killer for me.

For years I'd been somewhat stunned that the U.S. government sent me a paycheck twice a month. I'd have worked for nothing, except for pesky requirements like rent, groceries, and my kid's college savings. My next career had to generate equal enthusiasm, so I considered the likelihood of being paid for two other activities that I adored: writing and travel. Since my network-centric warfare article (and another on work-life balance) had been well-received in the Navy's professional journal, a freelance travel writing career seemed achievable.

There was one problem. The average editor did not seem interested in my, um, two clips. I needed a portfolio, and that's when I learned another freelance writing lesson: look around you and then write about it. There's always a story there somewhere.

Ergo, the newspaper op-ed college basketball write-up. Yes, yes, I'm getting to the drag racing assignment, but the road hasn't forked yet.

At the time, I was looking forward to the upcoming NCAA spring basketball tournament known as March Madness, and thought that it might be fun to write about how I became a hoops fan. My essay even had a place to go; the guy living next door to us happened to be the local paper's editorial page editor.

Here's one of the forks-- ready?

The op-ed submission is published, my friends cut it out and congratulate me and then my phone rings. It's the paper's entertainment section editor, who says that he loved the piece and asks if I would be interested in doing some classical music concert previews for him.

Clearly, we're not at the travel writing twist in the road just yet, but this is a marvelous opportunity and although I'm more of a jazz/blues/rock enthusiast, I take it. The articles required me to learn about the musical intricacies of Dvorak, the lineage of Hungarian Gypsy violin music plus the percussion techniques used in STOMP's stage productions.

The delicious thing is that I'm actually writing… learning how to interview, how to work with an editor, how to make myself smart on an unfamiliar topic, how to make the words sing from the page. I ordered business cards because someone actually asked me for one.

I was not, however, succeeding with my Plan A: travel writing. I was shopping around an article that I'd written about touring Tokyo with a preteen, but it was rejected over and over by magazines and newspaper travel section editors. Lonely Planet said "No thanks" to my guidebook writer application. My Family Travel blog was up and growing, but there were only about three readers per day. It was very discouraging, but I began to look for sellable possibilities in my own Gainesville, Florida backyard. Since the Sunshine State is an evergreen travel topic, my little college town ought to appeal to some publication, but I needed an angle, a hook.

How about drag racing? 

One of the biggest races of the National Hot Rod Association (NHRA) season is Gainesville's Gatornationals. I did not know diddly about NHRA other than a 1980s movie about Top Fuel driver Shirley Muldowney. Still, I could write pretty well and I was in the right place at the proverbial right time. There had to be some editor who would want my contribution. After running down any number of blind alleys in my research, I decided that rather than a travel focus, my best option would be writing about the races as a female newcomer to the sport. Since time was getting short (you use up a lot of days running down blind alleys) I knew that an online motor sports publication geared to women was my best bet.

Here's the scary part. I found a blog, The Driving Woman, on the car-buying website Edmunds.com. I surfed through it, noted their "Women in Motor Sports" category and figured out which person was the senior editor. At 10:43 a.m. one morning, I launched an e-mail query. To my absolute delight and horror, at 10:44 a.m. the editor responded that she was interested. Ten minutes later she called my cell phone and asked me for my tentative story lines. They were not immediately forthcoming-- I was still so stunned.

Insert, "Be careful what you ask for…." right here.

Within a few days I had press credentials for the race. I felt like the least qualified journalist on the entire planet. NHRA Media Relations gave me a numbered parking spot and a designated desk in the press room, and I didn't even know how to get to the racetrack parking lot, much less the press room. They also sent me the PR contact information for a number of female drivers and crew members. I dutifully e-mailed a few interview requests, expecting them to go into the usual black hole of non-response. Little did I know that the NHRA prides itself on driver and crew accessibility to fans and media; in short order I had interview slots lined up with several drivers including the legendary Shirley Muldowney herself.

That weekend at Gatornationals was one of the most terrifying and exhilarating few days that I've ever experienced. The interviews were wonderful, a few of the press room folks took me under their wing and the races were terrific. Between blogging and watching and even taking some halfway decent photos with my brand new digital camera, I learned something about how to be a sportswriter. Completely clueless, I fell back onto one of my best assets; I had more than two decades as a professional military officer who could deliver items on time and work with a variety of bosses in high-pressure situations. Looking dumb for a weekend at a drag strip was relatively small potatoes in comparison, as long as I learned quickly and sent in good posts to my editor.

After I wrote my wrap-up at the end of the race, I immediately plotted how I could get hired to do it again. Today I am quite flummoxed to report to you that I write regularly for the motor sports blog Fast Machines, covering mostly NHRA events but also a bit of NASCAR. My closet is full of lurid racing T-shirts covered in dragsters and nitro flames, and National Dragster magazine arrives in my mailbox every few weeks.

But here's the kicker…

A few days after the Gatornationals, I called the San Antonio Express-News, to see if the paper's travel editor had seen my pitch for the oft-pummeled and still unloved Tokyo article. A human being picked up the phone, told me that the travel editor had left and he was filling in, and that he'd like to see my article. I re-sent the piece, and he bought it and ran it in the travel section one glorious Sunday in April.

I finally had my published travel clip, but along the way I had also written a basketball clip, music clips, and drag racing clips. It seemed much too limiting to say that I only crafted articles about travel.

I had become, and I am still today, just "a freelance writer."

Sheila Scarborough was born into a Navy family in Key West, Florida. She served for almost 23 years as a Surface Warfare Officer in the U.S. Navy aboard ships homeported in Hawaii, California, Virginia, and Japan plus shore duty in Washington D.C. and Rhode Island. She also lived overseas with her family in the Netherlands during a tour with NATO.

She began writing part-time while on active duty, and is now enjoying a successful career as a full-time freelance writer, specializing in travel but conversant in a variety of topics.

A certified Navy Master Training Specialist and former Associate Professor of Naval Science at the University of Florida, Sheila is also an enthusiastic and knowledgeable public speaker and teacher.

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