How a woman who never expected to make more than $40,000 a year built a 6-figure business that allowed her to move abroad

Caitlin PyleCaitlin and Ben Pyle in Ecuador.

In the summer of 2014, Caitlin and Ben Pyle were living in Orlando, Florida, earning $US5,000-$US6,000 a month between Caitlin’s job proofreading transcripts for court reporters and Ben’s work as a college financial aid officer.

“Ben had a 45-minute commute each way,” Caitlin remembers, “and he hated it. I never saw him, and for the paycheck he was bringing home, it just wasn’t worth it. We could totally survive on my income, so I said, ‘Why don’t you do something different?'”

Ben joined online entrepreneurship community The Foundation in August, and in September, the Pyles made two big decisions: First of all, Ben would leave his job to build his own company. Second, they would make it happen while living in Ecuador.

On a flight home from a trip to Jamaica a few years earlier, the Pyles had seen an HGTV show where a family looked for a home in Cuencas, Ecuador, and were impressed by the area’s beauty and affordability. “Instead of waiting until you have a business up and running, why don’t we do it now?'” Caitlin remembers thinking. “We thought Ecuador would be a good place to start living the dream earlier — there’s never really a good time or best time. You just have to do it, don’t wait.”

However, the Pyles ended up staying stateside for nearly a year, during which Caitlin decided to undertake her own entrepreneurial project. Used to aspiring court proofreaders asking for her help attaining the necessary skills to book work in the field, she wrote an ebook on the subject in the fall of 2014. “Honest to God I thought that was all anyone needed to become a good proofreader, but I found out early on that wasn’t going to be the case,” she says.

Caitlin was being inundated with questions from readers with questions from the material, and by February 2015, she released a full-length course on proofreading on her website, Proofread Anywhere. Currently, she offers four options on her website: a 30-day “jumpstart” course for $US197; the full, basic course for $US897; the course plus some email support, including Caitlin’s personal feedback on your resume and website, for $US997; and the VIP version for $US1,197, which offers every service listed plus two 30-minute one-on-one phone calls.

Caitlin PyleCuencas, Ecuador is only the first stop on the Pyles’ 14-month trip through Central and South America.

In the course’s first month, the Pyles made a $US9,000 profit, and the numbers kept climbing. As of July 1, the Pyles have earned over $US250,000 profit from the business.

They paid off their $US60,000 mortgage, rented the house in Florida, and finally relocated to Cuencas, Ecuador in July for the first stage of a 14-month adventure through Central and South America.

“It’s still pretty surreal,” says Caitlin, who at one point had accepted that her career as a proofreader meant she’d probably never earn more than $US40,000 a year. “I’m still pinching pennies out of habit. I still live pretty frugally — I don’t buy a lot of stuff just because I want it or go to the most expensive restaurants. It feels good because man, I don’t think I’m ever going to have to worry about money again. It’s several years’ worth of income we’ve made in six months!”

While Caitlin maintains Proofread Anywhere and Ben pursues new business opportunities in consulting, they’re piloting a new program together meant to help other people build location-independent careers called The Work Anywhere Life. Soon, they will set off across the continent, including stops in Peru, Bolivia, Chile, Uruguay, and Colombia, returning to the US in the fall of 2016.

“Think about what you’re always helping people with,” Caitlin advises others who wish to follow a similar career path. “If you get enough people asking you to teach them something, or for advice about the same topic, it’s a good sign you have something of value. The hard part is finding someone or something to teach you how to monetise that. If Ben and I can do it with a tiny market no one’s ever heard of, I think a lot of people could be just as profitable.”

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