About The ReImagination Café™
The ReImagination Café™ is an independent media platform dedicated to thoughtful conversations with people who are reimagining work and helping to build a better world.
Through documentary-style interviews and written conversations, we explore how people draw on personal experience, imagination, and values to reimagine work, strengthen communities, and create more human, connected, and hopeful futures.
Our guests come from a wide range of backgrounds and disciplines, including business, education, technology, the arts, mental health advocacy, nonprofit leadership, and community development.
While the project began with a focus on creating better workplaces, the conversations naturally expanded into broader questions about purpose, belonging, mental health, inclusion, community, leadership, and the complex realities people navigate in their lives and work.
At its core, The ReImagination Café™ is about honoring people and creating space for authentic, meaningful dialogue. We believe that some of the most important conversations happen when people feel safe enough to share not only their ideas and accomplishments, but also the experiences that shaped them.
Why This Work Matters
We are living through a time of profound change in the way people think about work, leadership, identity, success, and community. Yet many public conversations leave little room for reflection, vulnerability, nuance, or genuine human connection.
The ReImagination Café™ was created as a space for something different.
Our guests are invited to move beyond soundbites and speak honestly about their journeys, challenges, hopes, failures, and aspirations. Some conversations are deeply personal. Others explore innovative ideas and emerging possibilities. Many do both.
Above all, we hope these stories foster connection, spark meaningful dialogue, celebrate our shared humanity, and offer hope for a better future.
The People Behind The ReImagination Café™
The ReImagination Café™ is a collaborative project shaped by a small team of people who care deeply about thoughtful storytelling, meaningful dialogue, and human connection.
Jessica Cherry
Jessica Cherry is the founder of ReImagining the Workplace LLC and the host of The ReImagination Café™.
Drawing on a background that spans law, media, nonprofit work, and narrative storytelling, Jessica is known for creating deeply researched, emotionally resonant conversations that explore the experiences, values, and defining moments that shape how people lead, create, and contribute to the world around them.
Her interview style reflects a longstanding interest in how personal experience shapes leadership, identity, creativity, and connection. Through immersive long-form conversations, she creates space for guests to move beyond surface-level discussions and engage honestly with the complexities of their lives and work.
Jessica’s work is distinguished by its intellectual rigor, curiosity, narrative insight, and commitment to creating thoughtful, deeply human conversations.
Kyle Picinic
Kyle Picinic is our Audio & Technical Director, handling everything behind the scenes to ensure that each podcast episode sounds clear, polished, and professional. With a background in web development and product management, he brings a broad and versatile technical skill set to his work. Kyle makes every conversation sound its best and plays a key role in bringing our vision to life.
“Kyle is the quiet force behind the scenes who not only keeps everything running smoothly, but also knows how to make me laugh when I need it most.“
- Jessica Cherry
Ben Cottrell
Ben Cottrell is our Social Media Strategist, expertly crafting narratives that connect and engage audiences with our podcast and its guests. With a strong foundation in digital marketing, content strategy, and graphic design, he brings creativity and thoughtfulness to every post. Ben's skill in merging storytelling with strategy helps The ReImagination Café™ reach new audiences and amplify the voices of inspiring changemakers who are reimagining work.
"When searching for a social media strategist, it was important to me to find someone who understands our values and mission and effectively conveys them through our social channels. Ben does this beautifully and is the perfect fit for our team"
- Jessica Cherry
The Heart of The ReImagination Café™
Lorenzo
Lorenzo is our Head of Recess and Play. Lorenzo offers unconditional love, keeps us grounded in the present, spreads joy, and never lets us forget the importance of play.