In Episode 5, former Discord CCO Steph Hess joins Barry to reflect on her fast-paced career in tech communications, sharing hard-earned lessons on crisis management and how a life-changing cancer diagnosis profoundly reshaped her personal and professional boundaries.

In Episode 4, Warner Music Group's Caeley O’Shea joins Barry to trace her path from early hospitality roles to leading live events, exploring how empathy, pacing, and the unifying power of music help her cultivate authentic connection in the workplace.

In Episode 3, NBA Social Impact & Inclusion Strategy Lead Melissa Palarea joins Barry to trace her diverse career path, reflecting on her 18-year journey with the league and sharing insights on fostering employee connection and embedding core values into everyday culture.

In Episode 2, Weber Shandwick's Adrian J. Hopkins joins Barry to trace his evolution from media to global communications leadership, reflecting on workplace authenticity, balancing creative and commercial tensions, and how following your natural interests can reveal your true career path.

In this episode, Braze CRO Ed McDonnell traces his career journey with Barry, revealing how taking risks, navigating rejections, and prioritizing human connection shaped his path to leadership.