Bridging Passion and Possibility: Chicago’s Approach to New Pathways

By: Getting Smart Staff

For the previous three years, Getting Smart has hosted regional New Pathways events sponsored by Britebound across the country, with the latest taking place in the great city of Chicago.

District and school leaders, educators, intermediaries, funders, and workforce organizations gathered to better understand how Chicago was preparing students for life and the workforce, with a focus on two specific strands: entrepreneurship and the arts.

The convening was hosted by Getting Smart and featured leaders like Shawnee Caruthers, Victoria Andrews, and Liz Texeira, alongside an inspiring slate of speakers and panelists. Keynote speaker Kara May from Art in Motion set the stage, followed by interactive panels and sessions with representatives from Future Founders, Uncharted Learning, Lincoln Lodge Comedy Club, and Big Picture Learning. Panelists and facilitators explored topics ranging from entrepreneurial mindsets to connecting through comedy and youth experiences.

A diverse group of participants and attendees from across the educational ecosystem joined the event, including school district leaders, foundation partners, and innovative educational organizations.

Founders and entrepreneurs, those recently graduated from high school and those further into their careers, took the stage to share their reflections on the power of entrepreneurship programming in their K-12 years, lessons they’ve learned since, and ways they believe we could design learning to better prepare students to thrive in a future where human connection, creativity, curiosity, and adaptability will matter more than ever.

Academy for Global Citizenship

Academy for Global Citizenship (AGC) is a K-8 public charter school in Chicago Public Schools (CPS). The school is all IB and is a dual language immersion school serving just over 500 learners. 

While CPS is facing enrollment challenges that mirror what we’re seeing in large districts across the country, AGC continues to thrive by teaching learners about wellbeing, holistic development, sustainability and much more. 

The model is organized around “Villages” clusters of grade bands and a sense of community/duty that has seven year olds delivering stacks, cooking lessons and gardening as a part of core curriculum in ever village and radically open classroom structures as a part of being one of the only schools to receive the award for the Living Building Challenge, a designation that means not only are you energy neutral, you’re actually contributing back to the grid.

Oak Park and River Forest High School

At Oak Park and River Forest High School, a school community serving approximately 3,900 students with 400 teachers just outside Chicago, creativity and entrepreneurial thinking are thriving. The energy throughout the school is contagious, with students and teachers deeply engaged in learning experiences that connect students’ interests to real-world opportunities.

In the entrepreneurship classrooms, students are preparing for upcoming business pitches through Uncharted Learning’s INCubatoredu program, incorporating MRI-Simmons consumer research. Rather than simply developing interesting ideas, students are researching existing solutions, analyzing competitors, identifying customer priorities, and considering what makes their products different and valuable. Classroom activities challenge them to look beyond their initial ideas, gather evidence, and answer important questions about the customers they hope to serve.

The business concepts reflect students’ creativity and personal interests. One team is developing ski and snowboard apparel that combines the style of streetwear with added warmth and protective padding. Another is exploring how AI could help coaches spend less time creating athlete highlight reels. Other groups are designing replacement soles for athletic shoes, baseball gloves that warm up without batteries, and a travel booking platform that offers a more engaging experience for younger travelers. Each idea demonstrates how students are learning to recognize opportunities, investigate problems, and imagine solutions.

That same commitment to authentic learning extends into the culinary classroom, where students operate a small restaurant and gain experience through a food delivery service. From entrepreneurship to culinary arts, students are developing practical skills while experiencing the responsibilities and possibilities that come with creating something for others.

What makes Oak Park and River Forest particularly compelling is the combination of student creativity, thoughtful instruction, and genuine enthusiasm for learning. Teachers create space for students to explore their ideas while providing the structure and tools to challenge their assumptions. Students, in turn, are discovering that they are not simply learners, but problem-solvers, creators, and entrepreneurs capable of contributing something meaningful to the world around them.

Fenton High School

Located less than 10 miles from O’Hare airport  is culturally diverse  Fenton High School, a solo school district in the Chicago area serving over 1200 students. The strong educational community at Fenton provides learners with a variety of learning experiences that align with their unique interests and correspond to surrounding businesses.  Students can explore advanced placement classes,  work-based learning opportunities, and  dual enrollment courses offered by the College of DuPage.

 As they continue to expand their dynamic offerings, the district is looking at the learning experience students encounter through UnCharted Learning’s INCubatoredu class. While in the early adoption phase of implementation, superintendent Dr. Jason Klein and staff appreciate the community interactions with students, agency in learning, and expansion of durable skills gained through the entrepreneurial class. They are examining ways to continue to grow the program and provide more personalized learning across the district.

While listening to educators, students, the superintendent, local business owners, and community members during a panel focused on entrepreneurship, it was evident everyone regardless of their role is willingly pouring into making learning different for students. During the lively discussion, each person is aware that the world is changing and so are the skills necessary to live and thrive but all shared a commitment to improving and expanding what learning can look like.