Nora O’Connor is a super collaborator, someone who loves singing harmonies and makes everyone sound good. She’s a member of the Chicago all-star group the Flat Five and a formidable singer-songwriter in her own right, as her 2022 solo album, My Heart , her first in 18 years, reminded us. Here she reflects on her life as “a music worker,” including what she’s learned from performing with such artists as the Decemberists, Iron & Wine, Mavis Staples, Andrew Bird, the New Pornographers and Neko Case. How has she has balanced her career and family life—and would a male performer have faced similar challenges? What ambitions does she have for herself and the Flat Five? What's the secret behind the alchemy she creates with frequent collaborator/Flat Five bandmate Kelly Hogan? And what role has the Chicago club the Hideout played in her musical life?