Last weekend, 100 Urban Initiatives students from across Chicago came together for the annual Middle School Leadership Retreat, focused on teamwork and connection – the monthly leadership skill emphasized for Team Captains this October.
The retreat began with a visit to the Museum of Science and Industry, where students explored exhibits, engaged in hands-on activities, and discovered new ways to be creative. Students were energized by the museum’s interactive experiences and loved using their curiosity and imagination to solve challenges and collaborate with peers from different neighborhoods.
The museum visit provided a unique opportunity to connect through learning while building relationships outside of their usual communities.
After the museum, students rotated through sports activities including flag football, soccer, and volleyball. Teams were intentionally mixed to encourage collaboration, communication, and teamwork – giving students hands-on ways to practice this month’s focus on connection.
A core part of the retreat was understanding the role of a Team Captain. Students explored what it means to wear the jersey: representing leadership, responsibility, and trust. They practiced guiding teammates, building relationships with a variety of peers, and adapting to different team dynamics.
This experience highlighted that effective leadership comes from teamwork, adaptability, and the ability to connect with others.
Urban Initiatives emphasizes a monthly skill for Captains, such as goal setting, conflict resolution, or communication. October’s focus on teamwork and connection gave students tangible ways to strengthen their leadership while fostering unity across Chicago’s neighborhoods.
A special thank-you goes to Mallory and Dansby Swanson of the Purpose and Calling Foundation for supporting the next generation with their generous donation of Wilson bags for all Team Captains – a thoughtful gift that made the retreat even more memorable.
By the end of the day, students left with new friendships, strengthened leadership skills, and bright new Wilson bags – a clear reminder that when young people come together through play and creativity, connection builds a stronger Chicago.
