The Challenge Day program, sometimes stylized as “ChallengeDay,” was founded by Rich Dutra-St. John and Yvonne St. John-Dutra in 1987 as a one-day workshop designed to promote empathy and connection among middle- and high-school students. Originally run as 14-hour Saturday marathons, the program was later reshaped into a six-and-a-half-hour school-day format to make it easier to adopt in schools.
Challenge Day is organized by a California-based nonprofit, which licenses its name from a separate LLC. The program gained wider visibility after appearing in Chicken Soup for the Teenage Soul in 1997 and expanded further in the wake of the 1999 Columbine shooting. Oprah Winfrey gave it a high-profile endorsement in the mid-2000s, framing it as a tool to fight loneliness and help young people connect.
Despite this acclaim, the program has long attracted criticism for its methods and safety practices. Workshops are conducted behind closed doors with covered windows, and they rely on emotionally charged techniques. Exercises can include sad music, guided imagery around death, and emotionally revealing group activities. Detractors argue these methods verge on psychological manipulation and lack adequate follow-up for students who may have intense or destabilizing reactions.
Another common criticism concerns the lack of scientific validation. Challenge Day has not been endorsed by the Substance Abuse and Mental Health Services Administration (SAMHSA), and studies on its effectiveness remain inconclusive. In Florida’s Manatee County, two high schools saw an uptick in violence and suspensions during the years the program was implemented. Collier County schools later placed Challenge Day on permanent hold after safety concerns surfaced.
Challenge Day has been linked to personal development movements including the Human Awareness Institute and the Landmark Forum. Promotional language often refers to the workshops as “transformational” or “spiritual,” and founders describe the work as a “gift we’ve been invited to shepherd.” Critics say such phrasing introduces a quasi-religious undertone that may be inappropriate for public schools.
One of the program’s central features, the “Crossing the Line” exercise, asks students to step forward if they have experienced traumas such as sexual assault, addiction, or exposure to violence. While intended to build solidarity, some participants have described it as exploitative and unsafe, particularly given that the activity was adapted from programs for violent offenders and people struggling with substance abuse.
Challenge Day is frequently offered at no cost to schools, funded instead by local donors and volunteers. Critics suggest this financial model may encourage schools to adopt the program without thoroughly reviewing its risks or effectiveness.
Key Sources:
Lewis, K. (2006, January 26). School officials put anti-bullying program on hold to check into safety issues. The Naples Daily News.
Roberts, D. (2008, January 11). School board challenges Challenge Day. The Brentwood Press.
The Seattle Times. (2002, April 12). Schools shouldn’t endorse psycho-fests.
Encyclopedia of Cults, Sects, and New Religious Movements 