Will Kiley Santino’s cartoons came out of grief. He moved to Madison from Ohio for a job at TruScribe, an animated whiteboard studio. His older brother received a cancer diagnosis, the two became roommates and life felt more urgent than before. Santino dropped to part time at TruScribe and enrolled in graduate school to get his MFA. He lost his brother at the end of 2017 and graduated only a few months later, in spring 2018. “That was when I started drawing New Yorker cartoons,” Santino says. “I didn’t intentionally think to myself, ‘I need to create something more light and humorous in order to survive,’ but that’s kind of what happened.” It took a whopping 400 submissions — about 10 cartoons a month — before The New Yorker editors bought Santino’s first cartoon in spring 2020. They’ve since bought 11. Meanwhile, Santino dove headlong into a staggering range of creative pursuits while building a social media following and enough Patreon supporters to become a full-time freelance illustrator. But in early 2023, after a lonely winter that made him realize drawing all day in his apartment for 10 years was a bit too isolating, a funny thing happened: He discovered comedy. Now he still does five cartoons a week, but he’s added open mic nights for stand-up and sketch comedy into the mix, and he’s found his creative community.

Rise and shine: Santino is a night owl, especially these days, so he might not wake up and pour the coffee until 10:30 or 11 a.m. Then it’s responding to emails, and either working on freelance jobs that pay the bills or following his muse — maybe drawing, painting, or writing whimsical poetry, graphic novels, a TV pilot or a comedy sketch. He sometimes works in his apartment, sometimes in coffee shops, but he always works. “I’m a believer in ‘sit down and work whether or not I feel funny at the moment,’ ” he says.

Process: If it isn’t winter, Santino hops on his bike for miles and miles of “intentional daydreaming.” “I think there’s a reason we use the analogy ‘getting the wheels turning,’ ” he says. “Just going for a lake loop, biking around town with my sketchbooks, with my laptop, that’s how I get ideas going.” Working in public places helps him avoid getting sucked into doom scrolling. “I’m less likely to stare at social media in a coffee shop than in the living room,” he says.