Courtney chats with Hillary Comstock, a creative director of 13 years within the fashion, beauty, and media spaces for a deep-dive into career, confidence, and cultivating a matriarchal balance in the workplace. Hillary shares how moving to New York to pursue career dreams in her 30s was the right call, and why being bold in her 20s set her up for real evolving success. They explore the importance of an equitable workplace, leading with empathy, and shaping work cultures based on the lessons she wished she'd learned earlier. Plus, Hillary honors the matriarchs who shaped her: her mom, a teacher who instilled a love for work, and her powerhouse stepmom, who thrived in a male-dominated field and led by example.

Courtney sits down with award-winning filmmaker and videographer for Vice President Kamala Harris, Azza Cohen and her wife, personal stylist, producer, and public interest lawyer, activist Kathleen Borschow. From supporting each other's wildest dreams—even when it means pivoting careers in their 30s (and even missing their own honeymoon to work on Kamala Harris' campaign!), Azza and Kathleen's love story is one of deep admiration, bold choices, and showing up for each other no matter what. The two of them open up about the fierce, resilient matriarchs who shaped their families - especially their bold grandmother who helped bring an entire community to the U.S. to another who taught the power of kindness. Azza shares behind-the-scenes stories from working on VP Kamala Harris' campaign, the inspiration behind her documentary work, and how listening with compassion makes for the best storytelling. We also find out what is next on the horizon for Kathleen and Azza's newly launched company, Cohen Borschow Media - and how they are continuing their shared commitment to changemaking through storytelling that matters.

Courtney chats with Erin LeBre, a two time Emmy and Guild Award nominated makeup artist and creative force, for a conversation about reinvention, resilience, and the power of maternal influence. Erin opens up about her early dreams of working in fashion, and the burnout that led her to an unexpected career pivot into working in the film and television industry. They dive into the art of saying no, the courage it takes as a freelancer to bet on yourself, and why success is something you're allowed to redefine at every stage of life. At the heart of Erin's journey is her mother—a single mom who raised two very different daughters with wisdom, grace, and an instinct for knowing exactly what kind of support they needed. Erin shares how her mother's unwavering belief in her shaped the way she approaches her career and life. It's a conversation about evolving, trusting the process, and staying a kid at heart.