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How Chicago Pathways Are Bridging Passion and Possibility

What happens when the ingenuity of the artist meets the drive of the entrepreneur? How do we ensure every learner can access pathways that blend creativity, agency and passion? From Expression to Enterprise on October 6-7, 2026, is designed to answer these questions by illuminating a connected learning ecosystemWe will explore how the creative process and expressive mindsetโ€”shared by artists and foundersโ€”are the essential vehicle for growth and adaptable skills in the age of AIThis is an invitation to fully immerse yourself in the Chicago ecosystem, showcasing how innovative, co-designed pathways are bridging the gap between education and emerging workforce demands, fostering inclusivity and forward-thinking strategies.

Register

Keynote Speaker: Kara May

Kara Bickhem May is a change maker in education with over three decades of experience leading at the intersection of innovation and purpose. She currently serves as Executive Director of Arts & Partnerships for Art In Motion Creative Arts School in Chicago, and as a founding principal and Educational Partner with FREE TO DREAMโ„ข. Kara holds degrees in French, Vocal Performance, English, and Educational Leadership, and has shared her expertise on stages including ASU+GSV Summit, SXSW EDU, and the Social Innovation Summit. One of her published works, “Educating at the Intersection of Purpose and Passion,” reflects her belief that love is a radical act of educational leadership. Kara builds with vision, and dreams in color.

Logistics

Venues

Bar Tabu | Tue Oct 6 (401 N Morgan St, Chicago, IL 60642)

By Transit

  • Morgan stop on the Green/Pink (0.3 mi)
  • Grand stop on the Blue (0.4 mi)

Nearby Public Parking

  • Fulton & Desplaines Self Park, 650 W Fulton St, Chicago, IL 60661
  • Mid City Parking Lot, 810 W Kinzie St, Chicago, IL 60654
  • SP+ Parking, 365 N Halsted St, Chicago, IL 60661
  • 333 N Green St Garage, 333 N Green St, Chicago, IL 60607

mHub | Wed Oct 7 (1623 W Fulton St, Chicago, IL 60612)

  • mHUB is located in one of the most bike-friendly areas of Chicago.
  • The Green and Pink lines stop at Ashland and Lake just one block south of mHUB. The CTA 9 bus also has a stop right in front of mHUB.
  • There is also free and paid street parking around the building on Fulton & Walnut. 

Hotel

The opportunity to book a room with our hotel room block ended on Sep 8 but you are welcome to contact the hotel directly to see if there is still space and if they will honor our group rate! Crowne Plaza Chicago West Loop (25 South Halsted Street, Chicago, IL 60661). Reservations: 800-972-2494 (9AM-8PM EST)

Additional Details:

  • Reservations #: 800-972-2494 (9AM-8PM EST)
  • *Please note that if needed luggage can be stored at the front desk of the hotel, or can be brought with you and stored on-site at mHub, during the convening events on Wed Oct 7

Agenda

Tuesday, October 6 @ Bar Tabu


5:00-7:00pm Dinner + Networking

Wednesday, October 7 @mHub


7:30-8:00am Coffee / Pastries + Check-In at mHub

8:00-8:20am Opening Session

8:20-8:40am Fireside Chat

8:40-8:55am Listening Session

9:00am-12:00pm School Site Visits (shuttles provided)

12:00-12:30pm Lunch

12:35-12:50pm Keynote

12:50-1:35 pm Session 1

1:35-2:20pm Session 2

2:20-3:05pm Session 3

3:05-3:15pm Closing


Sessions

Opening Session: How do we prepare young people to thrive in a future where human connection, creativity, curiosity, and adaptability matter more than ever? 

Speakers:

Fireside Chat: Uncharted Learning alumni reflect on the power of entrepreneurship programming in their K-12 experience in preparing them for their future and the state of the current workforce.

Speakers:

Keynote: Kara Bickhem May is a change maker in education with over three decades of experience leading at the intersection of innovation and purpose. She currently serves as Executive Director of Arts & Partnerships for Art In Motion Creative Arts School in Chicago, and as a founding principal and Educational Partner with FREE TO DREAMโ„ข. Kara holds degrees in French, Vocal Performance, English, and Educational Leadership, and has shared her expertise on stages including ASU+GSV Summit, SXSW EDU, and the Social Innovation Summit. One of her published works, “Educating at the Intersection of Purpose and Passion,” reflects her belief that love is a radical act of educational leadership. Kara builds with vision, and dreams in color.

Speakers: Kara May, Art in Motion

Listening Session: A mini listening session featuring stories from The Advisory: Class of 2006, a multimedia project reconnecting with young people Andrew Frishman of Big Picture Learning advised at The Met in Providence who graduated twenty years ago. Twenty years later, what actually mattered? What experiences, relationships, interests, internships, mentors, choices, and opportunities ended up shaping who they becameโ€”and the lives and careers they built? And what might those lessons suggest about how we design learning, advising, and opportunities for young people now.

Speakers: Andrew Frishman, Big Picture Learning

Connecting Through Comedy!: Lincoln Lodge instructors will walk participants through the basics of improv and standup comedy, as well as tips for public speaking and performance.  Attendees will have the opportunity to watch and participate in youth friendly activities that can be brought back to their schools for implementation.  The following concepts will be covered during the session: “yes, and…”, active listening, being open to silly play, sharing your unique perspective, finding your voice & public speaking basics. 

Speakers:

Future Founders: Hear from entrepreneurs aged 18-30 share about their journeys, and reflecting on what would have been helpful as a young person navigating future pathways, how they navigated the barriers and traditional systems, and how the broader educational ecosystem could have better prepared them to become an entrepreneur.

Speakers:

Think Like an Entrepreneur: A Mindset for Every Classroom

Entrepreneurship is more than starting a businessโ€ฆit is a way of seeing problems, imagining possibilities, creating value, and turning ideas into action. In this interactive session, participants will experience a simple entrepreneurial process and Idea Model Canvas) they can use across subjects, grade levels, and pathways. District educators will share how they bring this approach to life with elementary through high school students, why these experiences matter, and what they learned along the way. Participants will get a chance to practice with this tool and take back learning to your teams. Together, weโ€™ll explore how entrepreneurial learning builds creativity, problem-solving, adaptability, and agency so these skills can become part of every student’s learning.

Speakers:

Closing Session: Reflect on what weโ€™ve discovered, the connections weโ€™ve made, and the possibilities that have emerged. Together, weโ€™ll consider what weโ€™re taking forward, where we see opportunities for continued collaboration, and what it will take to turn shared ideas into action.

Speakers:

Site Visits

Fenton High School | โ€œSince 1955, District 100 has offered a comprehensive educational program to students in grades 9-12 who live within the Illinois communities of Bensenville and Wood Dale. With a student enrollment of approximately 1,500 students, Fenton offers an unusual combination of a suburban school education within a personalized, small-school environment. Curriculum choices and technology are continually being reviewed and updated to meet the ever-changing needs and demands of its students. As a complement to a highly skilled educational staff, students are exposed to a variety of state-of-the-art facilities including a fully equipped writing lab, a business education computer lab, general computer lab and other equipment specific to each department. The Business Department also operates the INCubator Edu program in which students enrolled in the full year Entrepreneurship class have the opportunity to create and fully develop their own product or service and incorporate it into a real world business they own.โ€

Oak Park and River Forest High School | โ€œWe are a comprehensive public high school located in Oak Park, Ill., a suburb eight miles due west of downtown Chicago. We are a one-school district, with the majority of our students coming from two sender districts, River Forest Public Schools District 90 and Oak Park Elementary School District 97. Oak Park and River Forest are communities that highly value diversity. OPRFHS is a founding member of the national Minority Student Achievement Network, and our school is racially diverse. We are economically diverse as well, with a significant mix of homeowners and renters. Our villages have also long embraced the LGBTQ community.The Business INCubatoredu program at Oak Park and River Forest High School is an entrepreneurship class where students build real startups, guided by community mentors and local business leadersโ€

Academy for Global Citizenship | โ€œThe Academy for Global Citizenship (AGC) is reimagining whatโ€™s possible in public education. As a non-profit Chicago public charter school located on the cityโ€™s urban southwest side, AGC’s innovative educational model develops mindful leaders in an entirely new learning environment rooted in wonder, sustainability, and community.โ€


Who Should Attend?

  1. K-12 and postsecondary educator leaders who wish to share and learn
  2. School counselors, advisors and student support staff who wish to better connect students to pathways, credentials and community-based opportunities.
  3. Local and regional business and industry leaders who wish to explore opportunities for partnerships
  4. Service and impact organizations looking to expand their reach or better understand how to support schools and districts

We especially welcome those not yet engaged in pathways / unbundled systems work and interested in exploring whatโ€™s possible!


Register

Select all nights you plan to stay. If you do not need a hotel, choose the last option.