Dreamkeeper™ Spotlight: Kara May
Educator. Nurturer of Young Dreams.
Kara May is the Executive Director of Arts and Partnerships and Co-Founder of Art in Motion, a creative arts charter school on Chicago’s South Side that she co-founded with hip hop artist Common, the Distinctive Schools Network, and a local church. As a Dreamkeeper™, Kara has not just built a school, but has started a movement designed to foster artistic creativity, compassion, and courageous dreaming among Black and Brown youth. Kara’s own dream and story are deeply interwoven with the dreams and stories of the young people she educates and inspires. In an education system full of status quo thinking, Kara is a priceless gift. We love her because she calls each of us to look for the best in ourselves and others. She urges adults to lead from a place of authenticity and to model two attributes the world needs far more of – creativity, and kindness.
“Your dream isn’t random. It’s a preview of what’s possible.” - Kara May
Kara May In Conversation
Q. What makes you an unconventional educator?
I am different. It took me a long time to realize that I’m wired differently than other educators. I lead with love and I believe you have to model what you want to see from others. That means being able to understand what children are saying, and what they aren’t. I love people at my core; it’s who I am.
Q. Why do dreams matter?
Our dreams are not just for us. They are the seeds of a future we may never get to see, but one that we are called to help grow. Our children – all of them – are amazingly beautiful and creative beings. The shyest, surliest, the [insert any adjective] of them. They all have dreams and a creativity that can help us as a society. My work is giving them permission to live original lives.
Q. What’s a dream you have outgrown or let go of?
I once measured success by society’s checklist: the right car; the right partner; the right job. With experience I realized this path was more about performance than purpose. Now, my success is slower, richer, and more rooted. It’s family dinners, spiritual alignment, and work that feeds my soul.
Q. If your own dream were a movie, what would it be called?
It would be called But What About the Children? Too often, our educational spaces are filled with noise and no action. Kids have a radar for knowing when an adult doesn’t care. In marginalized communities, that radar keeps them safe. So I always explain the ‘why’ and I honor children's need to be heard and be given the benefit of the doubt.
Q. Who inspires you?
My daughter. Her courage challenges me to reimagine my own dreams. She inspires me without even realizing it. That’s the power of generational dreaming. Each new vision builds upon the last, and love is the architect.
Q. Your words of wisdom for young artists?
Your dream isn’t random. It’s a preview of what’s possible. You are more than a test score. Trust and embrace your unique gifts and ask yourself, “What dream am I ready to plant today?”