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

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

Episode 91, ACT 2: Ann Gregg - Expand Your Mind

What if curiosity isn’t just a personality trait, but a practice? What if imagining the future is itself a form of teaching artistry?

In Act One of this conversation, Courtney sits down with arts educator, arts leader, and entrepreneur Ann Gregg for a wide-ranging conversation about curiosity, creativity, community, and the many paths that can make up a life in the arts.

Ann’s career has moved through public school music education, professional performance, teaching artistry, philanthropy, cultural institutions, and now entrepreneurship. Along the way, she has learned to follow the questions that keep opening new doors. Today, she and her husband run Into the Future, a neighborhood resource designed to give young people space to play, imagine, build, and think expansively about what might be possible.

Together, Courtney and Ann explore the relationship between arts education and futurism, and the power of asking “What if?” before rushing toward the practicalities of what is possible right now. They talk about free play, imagination, curiosity, and the importance of giving young people opportunities to envision futures that don't yet exist.

Their conversation also moves into the heart of teaching artistry: relationship. Ann reflects on discovering the language of “teaching artist” after already having spent years living it, her experience helping build the Teaching Artists Collaborative at Carnegie Hall, and the ways relationships with artists, educators, and young people can shape programs over time.

From neighborhood storefronts to Carnegie Hall, from the viola to public school classrooms, from planting seeds to imagining seven generations into the future, Ann and Courtney consider what happens when we stop trying to solve everything immediately and instead create the conditions for something to grow.
This episode is an invitation to stay curious, make room for possibility, and remember that sometimes the most powerful question we can ask is simply: What if?

In this episode, you'll hear about:
-Curiosity, imagination, and futurism as practices of arts education
-The creation of Into the Future and its focus on play, learning, and building
-Ann's journey from professional violist to public school music teacher and teaching artist
-Discovering the meaning of “teaching artist” at Carnegie Hall
-The power of local relationships and community-rooted work
-Trust, long-term thinking, and imagining seven generations into the future
-How arts programs evolve when participants have real agency in shaping them
-Why teaching artistry is ultimately about being in relationship

Guest: Ann Gregg
Host: Courtney J. Boddie
Creative Producer: Jonathan Zautner

Act Two continues Ann and Courtney's conversation, going deeper into teaching artistry, relationship, power, and the ways arts programs can evolve when we listen closely to the people at the center of the work.

What if curiosity isn’t just a personality trait, but a practice? What if imagining the future is itself a form of teaching artistry? In Act One of this conversation, Courtney sits down with arts educator, arts leader, and entrepreneur Ann Gregg for a wide-ranging conversation about curiosity, creativity, community, and the many paths that can make up a life in the arts. Ann’s career has moved through public school music education, professional performance, teaching artistry, philanthropy, cultural institutions, and now entrepreneurship. Along the way, she has learned to follow the questions that keep opening new doors. Today, she and her husband run Into the Future, a neighborhood resource designed to give young people space to play, imagine, build, and think expansively about what might be possible. Together, Courtney and Ann explore the relationship between arts education and futurism, and the power of asking “What if?” before rushing toward the practicalities of what is possible right now. They talk about free play, imagination, curiosity, and the importance of giving young people opportunities to envision futures that don't yet exist. Their conversation also moves into the heart of teaching artistry: relationship. Ann reflects on discovering the language of “teaching artist” after already having spent years living it, her experience helping build the Teaching Artists Collaborative at Carnegie Hall, and the ways relationships with artists, educators, and young people can shape programs over time. From neighborhood storefronts to Carnegie Hall, from the viola to public school classrooms, from planting seeds to imagining seven generations into the future, Ann and Courtney consider what happens when we stop trying to solve everything immediately and instead create the conditions for something to grow. This episode is an invitation to stay curious, make room for possibility, and remember that sometimes the most powerful question we can ask is simply: What if? In this episode, you'll hear about: -Curiosity, imagination, and futurism as practices of arts education -The creation of Into the Future and its focus on play, learning, and building -Ann's journey from professional violist to public school music teacher and teaching artist -Discovering the meaning of “teaching artist” at Carnegie Hall -The power of local relationships and community-rooted work -Trust, long-term thinking, and imagining seven generations into the future -How arts programs evolve when participants have real agency in shaping them -Why teaching artistry is ultimately about being in relationship Guest: Ann Gregg Host: Courtney J. Boddie Creative Producer: Jonathan Zautner Act Two continues Ann and Courtney's conversation, going deeper into teaching artistry, relationship, power, and the ways arts programs can evolve when we listen closely to the people at the center of the work.

Episode 91, ACT 1: Ann Gregg - Expand Your Mind

Episode 86, ACT 2: Katie Dawson-Beyond the Walls by Teaching Artistry with Courtney J. Boddie

Episode 86, ACT 2: Katie Dawson-Beyond the Walls

Episode 86, ACT 1: Katie Dawson-Beyond the Walls by Teaching Artistry with Courtney J. Boddie

Episode 86, ACT 1: Katie Dawson-Beyond the Walls

Episode 85, ACT 2: Pablo Hernandez Basulto-Internal Possibility by Teaching Artistry with Courtney J. Boddie

Episode 85, ACT 2: Pablo Hernandez Basulto-Internal Possibility

Episode 85, ACT 1: Pablo Hernandez Basulto-Internal Possibility by Teaching Artistry with Courtney J. Boddie

Episode 85, ACT 1: Pablo Hernandez Basulto-Internal Possibility

Episode 84, ACT 2: Ania Upstill- Creative Space for Possibility by Teaching Artistry with Courtney J. Boddie

Episode 84, ACT 2: Ania Upstill- Creative Space for Possibility

Episode 84, ACT 1: Ania Upstill - Creative Space for Possibility by Teaching Artistry with Courtney J. Boddie

Episode 84, ACT 1: Ania Upstill - Creative Space for Possibility

Episode 83, ACT 2: Michael Rohd- Authentic Process Designer by Teaching Artistry with Courtney J. Boddie

Episode 83, ACT 2: Michael Rohd- Authentic Process Designer

Episode 83, ACT 1: Michael Rohd- Authentic Process Designer by Teaching Artistry with Courtney J. Boddie

Episode 83, ACT 1: Michael Rohd- Authentic Process Designer

Episode 82: The TA Pod Squad- Teaching Artistry 2.0 by Teaching Artistry with Courtney J. Boddie

Episode 82: The TA Pod Squad- Teaching Artistry 2.0

Episode 81, ACT 2: Jean Taylor-Agents of Change by Teaching Artistry with Courtney J. Boddie

Episode 81, ACT 2: Jean Taylor-Agents of Change

Teaching Artistry blends creative and educational practice in service of community building, social justice, and inspiring joy. Courtney J. Boddie, Host and Creator, chats with teaching artists and arts educators who are driving professional teaching artistry forward. Courtney and her guests discuss personal journeys, celebrate triumphs and challenges, and advocate fiercely for the arts in all communities.

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