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Nov 10, 2022
From Air Force Writing to Upwork Freelancing


“If I die, help my wife get my book published!” That’s what I asked my master’s thesis instructor when I was deployed to Iraq because 1) I thought I’d written a great novel that would make a ton of money, and 2) I worried that my wife wouldn’t get royalties if I died in a rocket attack.  

Luckily I made it home in one piece, but I never got a book deal. A few years later, I retired from the Air Force and gave up trying to write novels. I didn’t give up writing, though. 

I’d always heard in the Air Force that “flexibility is the key to Air Power.” Actually, I believe flexibility is probably the key to just about anything, so I decided to try other types of writing. The problem was, I didn’t know how to find paying clients. But that’s when I discovered Upwork. 

I made an account and got the first job I bid on. It was small but I worked hard to “overdeliver.” I received an amazing review from the customer, who hired me for a second job. That’s when I knew I was on to something! 

Most of the writing jobs I ran across were for businesses needing articles (i.e., content) or copywriting for their websites. It wasn’t the type of creative fiction writing I’d studied…but I realized that, through my work in the Air Force, I’d developed skills for nonfiction writing, too. 

As a military admin, I’d written plenty of detailed, explanatory material based on boring military manuals. My audiences were diverse—from ROTC cadets at Oregon State University to Pentagon officers—but my goal was always to deliver clear, organized, easy-to-understand material featuring clear takeaways. 

My military writing experiences, combined with a bit of creative flair from my master’s degree studies, made me a good match for many of the projects I found on Upwork. I bid on all sorts of freelance jobs—copywriting, product descriptions, resumes, video scripts, you name it. I even tried my hand at branding, sometimes earning up to $75 an hour to think of catchy brand names and slogans (even though I’d never done it before). 

I then applied my research skills to figure out the “behind the scenes” workings of the Upwork platform. By understanding the little details of how Upwork functions, I was able to keep my Job Success Score high and build up a solid reputation. 

Since starting, I’ve tweaked my profile many times and experimented with different hourly rates, looking for the sweet spot where I could attract the clients—and the pay—I wanted. All told, it’s been a very enjoyable experience, allowing me to bring in over $134,000 in extra income while collaborating with clients around the world. 

But none of that compares to how happy I was when I turned one of my old military friends onto the platform, knowing he’d excel at freelancing if he ever tried it. Sure enough, he brought all his talents to bear to seize the writing opportunities he found on Upwork, quickly earning so much that he resigned from his university job. Basically, I’ve found Upwork to be what you make it. If you learn how it works, have a skill you can market remotely, and are persistent in your efforts, odds are you’ll land some great gigs and perhaps make some fantastic long-term customer relationships!