Paid Trips to Barcelona and Las Vegas: The Hidden Benefits of Freelancing
In 2006, Jennifer Choban moved from Portland, Oregon to Guanajuato, Mexico. She’d gotten divorced about a year before and was looking for a change of scenery and a renewed sense of adventure. So, when a coworker told her she was buying a house in Guanajuato, “I suggested to her that I take care of it,” says Jennifer.
In return for free room and board, she agreed to help fix up the house. This was a win-win arrangement for Jennifer, who likes working with her hands and knows her way around a toolbox.
To pay her bills, Jennifer took on odd jobs for other expats in the area. Out of curiosity, she also registered on a new freelancing platform called Odesk, now known as Upwork. There she found a gig contributing posts to a travel blog. In those nascent days of online freelancing, the pay wasn’t great, only $8 per post, but Jennifer enjoyed the work. And between her various gigs, she was earning more than enough to pay her way in Mexico, with money left over to visit her father in Hawaii every year.
In time, Jennifer stopped writing the posts and focused on her odd jobs. But after a few years, she decided to get serious about building a career and so returned to Upwork.
After logging back onto the platform, she discovered the world of online freelancing had grown significantly, and with her existing profile and track record working online, she was able to get jobs editing ebooks, writing show notes for podcasts, producing grant proposals, and authoring personal biographies for professionals. It was a gig doing the latter—writing a LinkedIn bio for an Australian executive—that led to Jennifer’s full-time freelancing role.
“It was a good fit. We clicked,” says Jennifer. Her client clearly agreed because in the years that followed, she regularly contracted Jennifer for various assignments. Then in 2016, two other Australians invited this client to become part of a startup called Thinktilt, and the three of them recruited Jennifer to join the team as the company’s knowledge writer.
Similar to the way developers create apps that can be used on an iPhone, Thinktilt enables programmers to create add-ons for a tech platform called Jira. After signing on with the company, Jennifer was invited to meet the three Australians at a conference in San Jose, California. She has also traveled to Las Vegas and Barcelona on business—on the company’s dime, of course. And had the pandemic not hit, she would have visited the growing company, which now has 11 staff members, at its headquarters in Brisbane, Australia.
Jennifer works about 30 hours a week producing content for Thinktilt and earns a salary in Australian dollars that allows her to live comfortably in Mexico. Two years ago, she was able to purchase the house in Guanajuato from her former coworker.
Having successfully scaled the freelancing income ladder, Jennifer has several recommendations for building a career through Upwork. When starting out, she advises taking on various different gigs until you find the perfect fit.
Ultimately, though, you’ll want to concentrate on a specific area of expertise. Although working on a variety of jobs is a good way to find your strengths, Jennifer says that accepting assignments from many different clients works against you financially, because Upwork’s fee structure rewards focusing on the same client. So, your goal should be to identify a few select clients with ongoing assignments in your preferred area. She recommends researching Upwork for companies or individuals who have a large number of assignments to fill.
According to Jennifer, companies ask predictable questions to bidders, so in addition to having your profile and resume ready, you should research the typical questions and prepare your responses.
That way you’ll be ready when the perfect job comes along. Who knows? Maybe you’ll even form a permanent business relationship like Jennifer did, with a client who ends up hiring you and paying you to visit Barcelona, Las Vegas, and Australia.
By Louisa Rogers