A heartfelt, creative reunion nearly 30 years in the making.

This week, I rewind the clock and reconnect with my former high school art teacher and longtime creative inspiration, Orlando Leyba. Nearly three decades after our time together at the Cambridge School of Weston, we dive into a conversation that's filled with laughter, wisdom, and a deep sense of gratitude.

Orlando wasn’t just as a teacher, but as a true mentor — someone who saw the creative spark in me when I was a lost, rebellious 16-year-old trying to find my place in the world back in 1990. His belief in me, and the wild, wonderful community at CSW, helped change the course of my life.

Together, we dive into the magic of making art (and mistakes), why creativity matters now more than ever, and the challenges today’s students face in a world full of distractions like social media.

Orlando reflects on decades spent nurturing creativity (and some wild student art projects!) and offers grounded, heartfelt advice for anyone—at any age—looking to rediscover the joy of making things with their hands. There’s nostalgia, vulnerability, and a reminder that playful experimentation has a place in every stage of life.

Takeaways to consider:

• Art is essential for healing and connection: Creativity isn’t just a hobby—it’s a lifeline in a world that can feel chaotic and disconnected.
• Creativity begins with permission to play (and fail!): Perfection isn’t the goal—experimentation, joy, and starting over are how true breakthroughs happen.
• Community (and great teachers) matter: The people who believe in us, celebrate our quirks, and encourage our wild ideas can change the trajectory of our lives.

🎙️ Tune in and join us for a journey through the years, art, community, and all the beautiful messiness of making things real.

https://www.csw.org/alumni/reunion-2025

MORE ABOUT ORLANDO LEYBA

My work is the result of overlapping cultures, languages, and mores. These influences and experiences are distilled into shape, color, emotion and movement.

At times they are neither solid nor fluid; they are ephemeral and rooted in human experiences – well-intentioned, cyclical, and inherently flawed.

My paintings are derived from nature — my grandfather’s land, ancestral land grants, irrigated fields, acequias that my family has maintained for generations, etc.

These paintings meld the contradictions and dichotomies that I have witnessed in my own culture and within my hometown, as well as concepts about time, the spirit world, human interaction and the diversity of factors that influence change that we witness in the world from day to day.

I see these compositions as intermediaries between what is seen and what is assumed, what is plausible and what relies on faith. They are a human effort to bridge the gap between the material and the spiritual.

Orlando on Instagram | orlandoleyba.com