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Thank you for being here to learn about my story.

I look forward to connecting and learning about yours.


I am Kimberly Tsai Cawkwell.

A Mother. Educator. Creative. Thought Partner.

I believe in advocating to center the voices of our youth to drive and cultivate practices that create a more loving, just, and equitable world.

I believe in nurturing spaces where all folxs are seen for their full-selves, loved for their full-selves, and given spaces to thrive in all their full-beauty. 

Nature Tokens


I am a thought partner to those who wish to collectively advance equitable spaces for all of our youth.

A proud first-generation Taiwanese immigrant, mother, educator, and creative, Kimberly Tsai Cawkwell has served over thirteen years in the education ecosystem. As a current adjunct-faculty member at the High Tech High (HTH) Graduate School of Education and Director of Programs at Challenge Success, Kim is deeply honored to serve in spaces that cultivate Deeper Learning pedagogy in service of nurturing equitable spaces within K-12 schools.

Growing up as a multilingual learner in a semi-isolated motel next to a busy New Orleans expressway, living through the duality of American and Taiwanese cultures, and experiencing teaching and learning in variety of settings around the globe, Kim has developed a unique lens for culturally responsive,environments and insatiable desire to center student voices in classrooms. Through the opportunities to learn from students in her own classroom to students from diverse corners of our globe, Kim believes deeply in student-driven transformative learning that sparks a common love and joy to seek knowledge. As she continues to support systemic change that lifts up student voices and honors the passions and identities of all students, Kim is grateful for the invaluable knowledge gained from others, holds humility as a practitioner and mentor for Deeper Learning practices, and is continuously inspired by the beautiful humans who are called to serve youth. 

Prior to joining the Challenge Success, Kim was a founder of two High Tech Elementary (HTe) schools, a former colleague at the Center for Love & Justice,  the University of San Diego and New Tech Network, and a public servant in the Pasadena and San Diego regions. She holds a B.A. from the University of California, Riverside and M.Ed from the University of California, San Diego. When she's not designing and facilitating learning, Kim might be found spending quality time with her two daughters, loving spouse, and family in Oceanside, San Gabriel, and Taichung. 


"Education means to inspire people to live more abundantly, to learn to begin with life as they find it and make it better." - C.G. Woodson

Honors & Accolades

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Cara Colkler

High School Math Teacher

Cleveland Metropolitan School District

"I'll truly miss you as our coach. I think you did fantastic things with Collinwood and personally helped push my practice more in the short time we worked together than anyone had in the 4 years I spent teaching new tech. Thank you so much for all the value you added to the school. "

Jeff Feitelberg

Elementary Teacher

High Tech Elementary, North County

"You have inspired me to try new and unfamiliar products and methods when creating powerful student work. Every time I walk past your room I see things that I want to do(when I have more time). Thank you and we'll miss you"-

Andy Domingo 

TOSA, Technology Integration & Project-Based Learning

Oceanside Unified School District

"Kim does not just develop constomized trainings, he designs active, responsive learning experiences that transform the minds and hearts of the attendees. We would leave each day with her not only with knowledge and resources, but also with deep personal reflections & reflective tools, digital creations & applied artifacts, and empowered experiences to help move ourselves forward. Do not expect a "sit n git!" Be ready to experience what many only learn in abstraction."

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