For Lula Wiles, the trio made up of Isa Burke, Eleanor Buckland, and Mali Obomsawin, the question is central to the creation of their music—and it’s the title of their sophomore album, out in 2019 on Smithsonian Folkways Recordings. “We wanted to make an album that reflected, in a current way, what we are all staying up late thinking about and talking about over drinks at the dinner table,” says Obomsawin. “What is everyone worried about, confiding in their friends about, losing sleep about?”