Challenge Day Encourages Compassion, Respect at Detroit Enterprise
All it takes to shift a middle schooler’s mindset is one day.
That idea recently came to life at Detroit Enterprise Academy when the school hosted Challenge Day for seventh- and eighth-grade students. It’s a day-long interactive program that helps students and staff build connection and respect.
Principal Aaron Williams is in his first year at Detroit Enterprise but leaned on his experience with the program when he led Burton Glen Charter Academy. It’s the fifth time he has had Challenge Day at one of his schools, and it doesn’t sound like it will be the last.
“I always call Challenge Day the best session you can have to build school culture,” Williams said. “When it’s all said and done, the bottom line is about how we treat ourselves and how we treat each other.”
The day begins with an upbeat welcome, encouraging students to dance, high five, and play small games together. Program leaders set the table for the experience, which dives much deeper than a dance party.
Organizers then explore emotions and the cost of keeping them inside. They model healthy alternatives and share how to be real, vulnerable, and sincere. Leaders use the metaphor of an iceberg to illustrate that while the world may want to only see the top, there is much more substance beneath the water. They encouraged everyone to “drop the waterline” and share their authentic self with the world.
That led into a small group session, each with five students and one staff member. Everyone had a chance to be truly vulnerable and share their life experience. Conversations often moved groups to tears, connecting students and staff, who recognized the strength in each other’s vulnerability.
Student and Family Liaison Ashleigh Brown said these small groups helped her establish a rapport with students.
“I really like how we were able to have those family small groups with the students,” Brown said. “Even now when they see me in the hallway, they give me a hug or check in with me. I think it was a really good experience for them.”
The heart of Challenge Day is their “Cross the Line” activity. Leaders read statements and if they apply, participants cross over a line to the opposite side of the room. Statements start out trivial before much deeper and emotional prompts, such as: “Cross the line if you feel like you got to be a kid.”
“Cross the Line” allowed kids to build empathy and reflect on how the people they see every day go through some of the same things they do. When students bring this same level of care to school every day, the feel of the building shifts.
“The impact of Challenge Day is immediate,” Williams said. “When you get a large number of students to participate, it’s enough to shift the culture. And that’s why I wanted to do this early in the school year. I’ve done it in January before and realized I should do it to start the year.”
The rest of Challenge Day is filled with fun team bonding games like a rock, paper, scissors tournament, but with a twist. Participants partnered up and the loser of the matchup became the other person’s cheerleader. As the field got smaller, the cheering sections became bigger. This was just one of the many fun and engaging activities part of Challenge Day.
While the program is not explicitly linked to Moral Focus™, Williams said the curriculum is a natural partner to Challenge Day.
“The day hit every Moral Focus™ virtue, from Wisdom all the way to Integrity,” Williams said. “I can pin the virtues to every activity throughout the day to show that that was a Moral Focus™ activity on steroids.”
Students are still applying what they’ve learned, but thanks to Challenge Day, they’re ready to lead with their hearts and a little more compassion.
What a great way to build school culture and engage students! Great work Principal Williams and Ms. Brown! Keep it up, Detroit Enterprise!