Tuesday, March 19th, 2024
4:00pm – 5:15pm PT | 7:00pm – 8:15pm ET

The college admissions process can be a source of stress and anxiety for students and parents alike. This research-based workshop addresses many of the important questions we hear from families. What do college rankings really measure? Are students who attend more selective colleges better off later in life? What is “fit” and why does it matter? Participants will learn practical strategies to help reduce unnecessary pressure around the college admissions process and ways to support their student’s overall well-being and readiness for life in college and beyond.

A recording of the workshop will be sent to all registrants on March 20th.

If the cost of attending this workshop is a barrier for you or students you work with, please reach out about our financial assistance.

Who should attend

Parents, Students, Educators


Virtual / Online


$15 per person

Learning Objectives

  1. Learn research-based findings on the relationship between college selectivity and future outcomes, including learning, job satisfaction, and well-being.
  2. Explore practical strategies to embrace a healthier approach to the college admissions process.
  3. Gain a deeper understanding of the value and meaning of engagement in college and high school.


Jon Kleiman

Jon Kleiman, M.A., is the School and District Partnership Manager for Challenge Success. Jon’s chief mission is helping organizations and individuals challenge the status quo. In his role as a School & District Partnership Manager with Challenge Success, Jon’s worked with dozens of schools over the past several years in reimagining how schools might better support the needs and growth of its students. Previously, Jon worked at a university helping students to engage in “vocational wayfinding.” Jon lives in Portland, Maine with his wife and three kids. Jon also hates writing bios.

Kimberly Tsai Cawkwell

Kimberly Cawkwell, M.Ed., is a first-generation Taiwanese American, mother, educator, and creative. She has served over thirteen years in the education ecosystem. As the Director of Programs at Challenge Success, Kimberly is honored to be in community with others to advocate for equitable systems and practices that nurture wellbeing, belonging and engagement for all. In addition to her work at Challenge Success, Kimberly currently serves as an Educational Advisor at the High Tech High (HTH) Graduate School of Education; supporting M.Ed students in developing culturally sustaining/responsive pedagogy in their school spaces. 
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, Kimberly has developed a unique lens for culturally responsive environments and an insatiable desire to center student voices in classrooms. Through the opportunities to learn from students in her own classrooms to students from diverse corners of our globe, Kimberly 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 CS, Kim was a founder of two High Tech Elementary (HTe) project-based learning schools, a former coach and design specialist at the University of San Diego, New Tech Network, and Center for Love & Justice.. She holds a B.A. from the University of California, Riverside and M.Ed and multiple-subjects credential 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. Her core values are family, joy, and equity.

Li Hsiang (Lisa) Chung

Li Hsiang (Lisa) Chung (she/her) is the College and Career Counselor/Specialist at La Canada High School at La Canada, CA.  Prior to joining La Canada Unified School District and being responsible for establishing the La Canada High School College and Career Center in 2022, Lisa served as the Engineering and Medical Academy Counselor at John Burroughs High School in Burbank, CA. Lisa started her high school counseling career over 20 years ago at Granada Hills Charter High School, the largest charter school in the nation, and has continuously worked at public high schools to empower students and improve student outcomes.  Previously, Lisa worked as an adjunct professor at the California Lutheran University Graduate School of Education and at the University of California San Diego as a Senior Learning Skills Counselor in the Department of Psychiatry.  

Lisa holds a B.A. Psychology with a Chinese Studies Minor from the University of California San Diego and a M.A. Ed with Emphasis on School Counseling from the University of Redlands.  She is currently earning her administrative credential from the University of La Verne.  You can find Lisa outdoors on most weekends with her wonderful daughters and husband-overlanding, camping, and/or snowboarding…basically squeezing the most fun out of life possible.