Starting with the charge of preparing tomorrow’s leaders and workers today, educators must equip each student with both the technical skillset and the agile mindset to succeed in the modern work world. This requires a new school model that delivers both college preparation and workforce-ready technical training at the same time. It means a complete overhaul of the existing teaching and learning dynamic, so that schools deliver the knowledge and skills required of 21st century workers. However, in order to change such a stubborn system, we need a powerful coalition—representing a broad and diverse cross-section of stakeholders—to unite for the common cause of modernizing education pathways. We must align what schools teach to what the workforce actually needs. All of this is happening in the City of Chicago under a bold initiative called Future of Illinois. Learn how this unusual alliance between community, education, business, labor, and workforce development leaders are on the leading edge of educational innovation.