“I’m often described as someone scared of jumping, metaphorically speaking,” Kentaro Yamada says from Portugal, where he is busy visiting prehistoric cave paintings and admiring the ceramics of local artisans. Although he claims prudence, Kentaro’s life—from competitive sailing to his career as an artist—doesn’t appear hampered by cowardice or indecision. The trick, he claims, has always been to let his intuition lead the way. “Whenever I’ve achieved big steps or jumped to the next step, I didn’t even know I was doing it,” he concedes. “I was simply chasing my curiosity and my instinct. It’s a good way for me to be.”

As a teenager, instinct led Kentaro from Japan to New Zealand as he pursued dreams of sailing at the Olympics. But it was there that he experien...