In the elegant and kaleidoscopic “Hard Drive,” New York songwriter Cassandra Jenkins lets us in on a series of conversations. There’s a security guard with a Queens accent, a bookkeeper at an inn in California, a driving instructor named Darryl, and a psychic with gemstone eyes at a friend’s birthday party. They all seem to want Jenkins to relax her mind and open her heart to the world around her—which is, of course, easier said than done. As Jenkins figures things out, her band—featuring Stuart Bogie on saxophone, Eric Biondo on drums, and Josh Kaufman on guitar, keys, and fretless bass—settles into a glassy, sophisti-pop groove that glides like a slow journey uphill. In the chorus, her voice slips into a melodic sigh, but for the most part, she simply relays the words in her speaking voice: The effect is less like a conversation and more like listening in on Jenkins’ private voice memos, recorded for no one but herself. Plenty of songwriters can present with confidence the hard lessons they’ve learned; it is rare to hear someone so masterfully document the long, lonely journey of trying to get there.