Regular freelance work on fun jobs with a client you love and respect? For the past three years 28-year-old illustrator Oscar Bolton Green has been living every freelancer’s dream with Bloomberg Businessweek, where original art direction and commissions from up-and-coming talents like Green have attracted a younger, broader audience of late. I, for one, would probably never have given the financial title a passing glance were it not for spotting Green’s fun, humorous artwork on its pages—his characteristically cartoony images are just about the last thing you expect to find in sections like Bid/Ask, a regular column on the week’s biggest business deals.

Green had been illustrating for Businesweek online for a year before art director Chris Nosenzo (previously known only to me as the visionary behind the Yves Klein and Tobias Fünke book) commissioned him for the weekly Bid/Ask gig. Working against typically tight editorial deadlines and across times zones (Bussinessweek’s staff is in New York, and Green is based in London), Green would receive the main story every Tuesday evening—usually just a headline or a link—spend the next few hours sketching, and send his work off to Nosenzo, who shared it with his colleagues later that same day. “He usually chooses the weirdest one to share,” says Green. “Sometimes he would report back saying my drawings made people laugh in the meeting, which made me smile.” 

By the time Green woke up the following day, he’d already have feedback on the first round, as well as a to-do list of illustrations for the rest of the section, to be completed by lunchtime, right when the New York team would be getting to the office. “It was fast-paced like most editorial jobs, but there wasn’t much back and forth. There was a lot of trust, which is important, and that probably brought the best out of me.”

Over the course of his gig, Green produced hundreds of drawings around subjects he says he never would have focused on otherwise. “That’s one of the great things about illustration: I get to draw everything” Even the motifs that made regular appearances, “like the dollar bill, would take on many forms. It was fun to play with those clichés. If some of the subjects were a bit dry, that usually made for a better drawing.” Fortunately you don’t have to order three years’ worth of back issues to see all of Green’s work—he’s distilled the whole lot of it in a 30-second video (complete with an original soundtrack).

Even though Green’s stint at Businessweek has come to a close (for the time being, at least), open any other major paper, say the New York Times, and you’ll spot his handiwork. And who knows what unexpected places his drawings will pop up next. “I’m just going to keep drawing and see where it takes me,” he says.