What happens when we approach the world with curiosity instead of judgment? And what becomes possible when we give ourselves, and the young people in our lives, permission to imagine a different future?
In the second act of their conversation, Courtney J. Boddie and Ann Gregg pick up where they left off, exploring the questions that shape us as artists, educators, parents, and human beings. From the earliest lessons we absorb in our families to the people and experiences that challenge our assumptions, they consider how curiosity becomes more than a way of learning. It becomes a way of living, connecting, and making change.
Ann reflects on her winding professional journey, from teaching music in public schools to becoming Director of Education at From the Top and spending eleven years helping build programs at Carnegie Hall. Along the way, she discovered that an artistic life doesn't have to follow a single path. The balance between creating, teaching, and leading can shift over time, as long as we remain connected to what matters most.
That openness is also at the heart of Into the Future, the neighborhood initiative Ann co-founded with her husband, futurist Gary Golden. Through play, creativity, and hands-on exploration, young people are invited to look at the past, understand the present, and imagine futures that don't yet exist. For Ann, this work is inseparable from equity: making space for different perspectives, providing abundant possibilities rather than predetermined answers, and recognizing that our individual futures are bound up with the futures of our communities.
Courtney and Ann also take on some of the more complicated questions of our time. How do we respond to artificial intelligence and other disruptive technologies without abandoning either curiosity or our ethical responsibilities? What does it mean to advocate for change when the systems around us feel overwhelming? And how might asking better questions help us create more liberated learning environments, where young people's needs and experiences are met with care rather than judgment?
As the conversation turns toward passion, purpose, and the relationships that sustain a field, Courtney and Ann reflect on the artists, educators, mentors, and elders who helped shape teaching artistry in New York City. They imagine what it might look like to map those connections, honor the people whose contributions aren't always visible, and carry their knowledge into the next generation.
It's a conversation about the courage to keep learning, the generosity of sharing what we know, and the possibilities that emerge when we recognize our own agency alongside that of others.
And it all comes back to three simple agreements from Into the Future: Be safe. Be kind. Expand your mind.
In this episode, you'll hear about:
-How family, upbringing, and early experiences shape our instincts to teach, question, and care for others
-The difference between curiosity and judgment, and why that distinction matters for equity
-Ann's career journey from music education to From the Top and Carnegie Hall
-Finding purpose across artistic practice, teaching, and arts administration
-Creating learning environments that respond to young people's needs with curiosity and care
-How Into the Future connects imagination, abundance, and equity
-Navigating AI, technological disruption, and the responsibility to help shape our collective future
-Courtney's advocacy for portable benefits and greater support for creative workers
-Passion, self-agency, and the importance of investing in ourselves
-Honoring the mentors, elders, and relationships that have shaped the teaching artistry field
Guest: Ann Gregg
Host: Courtney J. Boddie
Creative Producer: Jonathan Zautner