Shea Serrano became a writer when, as a teacher in need of some extra money, he did a Google search for jobs you can do from home. “I didn't have any journalism experience. I didn't know anybody. All I had was the computer and the internet, and I figured that shit out,” says Serrano, who's now a staff writer at The Ringer. Along the way, he wrote three New York Times bestsellers and has established himself as a perennial Twitter all-star (where, when he’s not firing off extremely funny tweets, he’s leveraging his 330K followers to do things like raise $134,000 dollars for Hurricane Harvey victims). In other words, in a world where careers and work are unpredictable and self-doubt is inescapable, Shea Serrano has some lessons on how to bet on yourself—and win big.  Follow: Shea Serrano — @SheaSerrano Clay Skipper — @SkipperClay