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Kelly Cheek
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Did you ever see the 2002 movie Catch Me If You Can? It was based on the true story of Frank Abagnale Jr., a master conman who managed to swindle millions of dollars by the time he was twenty-two years old. During the course of his short career, he successfully impersonated a Pan Am pilot, a doctor and a legal prosecutor, before finally being arrested by the FBI agent who had made it his personal mission to catch him.

While I’m not glorifying the legal and moral deficiencies afflicting Frank, I can’t help but admire the confidence that he must have possessed to be able to successfully pull off such high-profile cons. Confidence is something that I’ve lacked my entire life.

I’ve written and published eleven novels, and have even sold a few copies of them. My monthly royalty statements from Amazon are usually in the triple digits, if you count the two digits that come after the decimal point.

I know there’s a lot more I need to do to market and promote my books, but never having learned about business and finances when I was young, I never felt confident that I could ever be successful. People like Stephen King, Michael Crichton, Dan Brown, and others who routinely sell millions of copies of their books always fascinated me, but their success always seemed out of my reach. I felt like an impostor trying to insinuate myself into their world, but without Frank Abagnale’s confidence to pull it off.

When Linda and I started thinking about moving overseas, I started looking into ways to support the venture with my writing. Online research was something I was accustomed to doing while writing, but now my research was about writing, for a living.

One program that I discovered and purchased was 21 Days to Freelancing Success Abroad, a program put out by Barefoot Consultants ( Barefoot Consultants was connected to AWAI, American Writers and Artists Institute (, and from them, I downloaded tons of PDFs about freelance writing, finding my niche, learning to write SEO content (Search Engine Optimization), how to find clients, etc.

The 21 Days course was an online program consisting of several prerecorded videos, multimedia modules and PDFs, and one of the main focuses of the program was learning how to make the best use of freelance job sites, particularly Upwork ( The instructor, Winton Churchill (really!), walked me through what to do and what not to do in creating my profile page, what to look for in finding jobs, how to determine if a potential client was a good one, and more.

As I said in the previous chapter, he said that it’s not at all uncommon to put out ten or twenty proposals before one is accepted. After I put up my profile page and started looking for work, I found this listing:

We seek a writer for Wormhole, a site concerned with de-stigmatizing the dark side of life. In all of our writing, we aim to discuss the sides of life that no one sees. We approach it from a creative standpoint; our articles read less like research papers, more like short stories.

We’d like a writer to compose an article about depression, and about putting up walls around them. This will be written in a first-person, internal monologue format. The writer should start the story by imagining what it’s like to not feel depressed — to be going about life in a clear-eyed, confident way. Then, the writer should transition into how the main character really feels, their self-doubt, their mistrust of the world, the joy sapping out of their surroundings. Have they shut people out of their lives, people whom they used to trust? Why? How does it feel? The writer should emphasize thoughts related to how the main character feels about themself, daily situations that wouldn’t affect most people, how they think others see them, and finally, how they think it might feel to be happy.

We value our artists’ creativity, and so if the writer has another approach they think would work, we’re more than open to hearing it. 1000-1500 words. 7 days for First Draft. 3 days for Final Article.

Depression is a topic I’m familiar with. I’ve suffered bouts of it myself and had already written two blog posts about it. (I included both of those blog posts as samples in my proposal.) But this was different. It wasn’t to be a cold, clinical article, but a short story. I could do that!

Chris, the client, accepted me and paid me $60 for my short story. Plus a $10 bonus because he really liked it. “By far the most creative piece I have read so far. Wow. It’s absolutely perfect and extremely creative.”

I know, $70 isn’t a lot for an original 1200 word story, but that wasn’t the point. Winton Churchill said that, in the beginning, it’s important to take smaller jobs in order to get ratings on my profile page. With no ratings, I look like a newbie, and the bigger jobs will be out of my reach. This first job was, for me, a slam dunk since the story appeared fully-formed in my head and practically wrote itself within a day, so I was well under the deadline, too. I got myself a rave review and a five-star rating for that.

I wrote another short story for Wormhole a week or two later, for similar pay and similar rating. With two successful writing jobs under my belt, I felt a little more confident to tackle bigger, better-paying jobs.

My confidence, it turned out, may have been a little misplaced.