Featured Podcasts

A collection of featured podcast episodes with leaders who are successfully transforming our workplaces so that everyone can live up to their full potential and thrive. From corporate executives, to workplace consultants, to mental health professionals, to owners of small businesses, there are bold individuals all around us who are challenging the status quo, strengthening our communities, and transforming the world of work. In these featured podcasts, workplace leaders join Jessica for deep and meaningful conversations about reimagining our workplaces, sharing both their personal stories, and their insights on what it takes to catalyze positive change.

Special Supplemental Background Track to Upcoming Episode: Hope Is Not Silent: Forging the Path to a Trans-Inclusive Workplace with Jess Skaare

Discovering Jess: A Story of Transition & Transformation

In this supplemental background track to the upcoming podcast, Hope Is Not Silent: Forging the Path to a Trans-Inclusive Workplace, Jessica is joined by Jess Skaare, who shares her personal experience grappling with her gender identity. Jess provides a raw account of the many years she spent believing that she was "unknowably broken" - knowing that something was "off" but not realizing that it was related to her gender. From the disappointment she felt when she saw herself in the mirror dressed as a woman for the first time, to the years of self-sabotaging her personal relationships to avoid the rejection she assumed was inevitable, to the one-woman intervention that served as the wake-up call she so desperately needed, Jess provides an extraordinarily candid and moving account of what she calls her journey to self-acceptance. Since coming out as transgender in August 2023, Jess has been sharing her personal story as part of her broader missions to promote greater awareness and understanding of the trans experience, and to fight for the dignity and validity of members of the trans community. 

Coming Soon!

Hope Is Not Silent: Forging the Path to a Trans-Inclusive Workplace with Jess Skaare

In this upcoming episode of ReImagining the Workplace, Jessica is joined by Jess Skaare, who describes transitioning and coming out as trans while working as a web developer at a large corporation in New York City. Jess first shares her personal experience grappling with her gender identity, including many years of feeling like a secondary character in her own life. She then addresses the role of her company's culture, including a strong LGBTQ+ community, in supporting her transition and making her feel safe enough to come out to her colleagues. Jess describes the overwhelming support she received when she came out, and proposes specific actions that senior leaders, managers, and colleagues can take to help create and maintain a trans-inclusive workplace.

Featured Podcast Episodes

  • “It’s nice to hear down to earth conversations about mental health in the workplace.”

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  • "Jessica Cherry brings on excellent, interesting guests - clearly experts in their fields. She has a warm, genuine way of engaging them, giving them plenty of space to share their wisdom, and following up with questions that take the conversation to deeper insights."

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  • "More conversations like this need to happen"

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