Challenge Day


Creating a world where every person feels safe, loved and celebrated since 1987

Founded in 1987 by Rich and Yvonne St. John-Dutra, Challenge Day started as a Bay Area organization. Now Challenge Day serves over 49 U.S. states, Canada, Belgium, and the Netherlands, Challenge Day is on a mission to create a world where every person in our communities feels safe, loved and celebrated.



35th Anniversary

The memories across thirty-five years of work are thick, and they go back to the very beginning. “I still remember the first Challenge Day we did,” says Yvonne, “and watching the magic unfolding, seeing the walls come down.


First in-person Challenge Day program after Covid Shutdown

On August 30, 2021, we held our first in-person Challenge Day in Locust Valley, NY for ninety seniors. The school decided to kick off their first day with Challenge Day to bridge the disconnect that the pandemic had caused for their students.


May 27, 2020, hosted our first ever Virtual Graduation Challenge Day

As the pandemic forced schools to close on March 17, 2020, the staff, founders and board knew that the youth continued to need programs like Challenge Day.  They knew the only way to continue to support our youth they would need to pivot and so virtual programs were created to ensure we could still offer connection even if just through a screen.  The first Virtual graduation day happened just 2 months after the shutdown and Challenge Day proceeded to offer virtual programs across the country for the next year and a half.


First Military Challenge Day – Peterson Airforce Base, Colorado Springs, CO 11/4/2019

Having attended a Challenge Day event as a teen, Staff Sgt. Andrew Tello, 21st Medical Group training manager, wanted to share with Peterson Air Force Base.  He says, “That’s why Challenge Day was so impactful for me.  It helps people learn to recognize internal and external social and emotional issues and pressures.” Airmen immersed in resiliency at Challenge Day.


Over de Streep – Dutch Television Program

On July 28, 2011, the Dutch television program “Over de Streep” produced by Posh Productions BV, aired to kick off a 4 season, 6-part series.  The show, hosted by Arie Boomsma, featured high school students taking part in Challenge Days.  The series highlighted 24 schools, including a school in Uganda.


If you really Knew me MTV Series

The MTV series, “If You Really Knew Me,” produced by Arnold Shapiro Productions goes inside the drama and life struggles of high school students, giving viewers an unfiltered look at life as a teenager today.  The show follows high school students from different cliques as they experience Challenge Day – a transformative one-day program that breaks down barriers between cliques, curbs prejudice and bullying (in the halls and online), and profoundly changes the way the students view their school and each other.


First corporate programs held at Coca-Cola

Inspired by Challenge Day’s work in schools across the nation, Steve Bucherati, Coca-Cola’s Group Director for Diversity and Fairness in North America, invited Challenge Day’s founders, Rich and Yvonne Dutra-St. John, to conduct a pilot Challenge Day at The Coca-Cola Company.Over 140 Coca-Cola employees “dropped the waterline,” opened their hearts, and took part in powerful validation exercises especially tailored to their on-the-job experiences.


Oprah's High School Challenge

In an emotional moment, Oprah brings the students, administrators, and Challenge Day founders Yvonne and Rich Dutra-St. John into the studio to talk about their experience and sees how remarkably the experience transformed racism at the school and showed that “real change and connection is possible.” Oprah says, “I just want to say this is how we change the world—one person at a time.”


Teen Files: Surviving High School

Arnold Shapiro Productions take us through the halls of Monroe High School and experience a Challenge Day firsthand in this 90-minute episode, hosted by Leeza Gibbons, and featuring Challenge Day’s founders Rich and Yvonne St. John – Dutra.  “The barriers came down when we all started crossing over that line…”


Challenge Day Begins

As graduates of the California public school system, Yvonne and Rich experienced first-hand the costs and consequences of bullying and isolation in school. Committed to making things better for their own children, they founded the innovative and award-winning Challenge Day Program in 1987.

Celebrating Our Founders

To talk with founder s  Yvonne and Rich about the history of Challenge Day is to take a journey across thirty-five years, one that begins with a shared conviction. “We believe everyone does the best they can, and that’s the place we meet them,” says Yvonne. “It’s where Challenge Day started, and it’s what the program still seeks to draw out from people: The best you have to offer.”

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