9 to 5ish with theSkimm

9 to 5ish with theSkimm is a career conversation show about ambition with receipts. It looks at how women built their working lives, then stays with the awkward middle parts that usually get cleaned up in a public biography. The format is direct. Episodes introduce a guest’s career arc, then move into the decisions, mistakes, relationships, and emotional costs behind it. Norma Kamali’s story starts with fashion illustration, airline work, London trips, a boutique, and the hard push from side project to real business. Her episode also lingers on confidence, help, partnership, money, and the discomfort of needing support when things feel humiliating. Rachel Zoe brings a different kind of origin story, from freelance styling in New York to touring musicians, Los Angeles, television, fashion media, subscriptions, venture work, and podcasting. Her frame is not a perfect plan. It is a long record of mistakes that became useful later. Molly Sims’ episode treats reinvention as something more physical and public, moving from college to modeling agencies, magazines, brands, acting, and beauty entrepreneurship. It also makes room for professional rejection, being fired, and leaving a bad fit without losing dignity. Alice Waters shifts the conversation toward values. Her story follows food, teaching, Chez Panisse, friends-and-family financing, wages, family life, farmers, and a resistance to making profit the whole point. Jenny Slate’s conversation turns career pressure inward. It connects performance, comedy, writing, Marcel the Shell, screen work, motherhood, self-questioning, and the decision to stop treating self-criticism as useful discipline. Erin and Sara Foster’s episode adds the charged terrain of taking risks with family. Their discussion makes business partnership feel personal, especially when sisterhood, childcare, money, mental health, and the desire to keep going collide. Across episodes, the show’s strength is its mix of access and practical candor. It is not a lecture. It is a set of conversations where women explain what they tried, what cracked, what paid off, and what they would handle differently now. The advice lands because it is tied to specific lives. The show suits listeners who want career perspective without sanding away emotion, taste, family, fear, or ambition.