In this episode of Stories from the Field, host Doug sits down with Dr. Matthew Wienclawski, Superintendent of Pathways in Education in Chicago. Matthew shares insights into the unique model of alternative education that Pathways offers, supporting students aged 16 to 22 who are overage and under-credited, and often juggle life responsibilities, such as work or caregiving, alongside their education.

Discover how Pathways provides flexible programming,students attend just four hours per day, with options for one-on-one, small group, or online learning. Matthew discusses the challenges and benefits of partnering with Chicago Public Schools under a contract model, maintaining autonomy while meeting district metrics, and running four campuses spread across the city (all coincidentally on the same avenue!).

Listen as Matthew reveals the entrepreneurial spirit behind Pathways, from individualized student success plans and hands-on mentorship to building an active alumni network and hiring graduates. He also opens up about his leadership journey, the impact of mentorship, and his focus on leading with humanity and grace, encouraging staff to learn from mistakes and fostering a responsive, supportive school culture.

Tune in for practical lessons in alternative education, flexible pathways to graduation, and creating a caring environment that values both students and staff.

Key Moments

00:00 Flexible programming limits student tenure to prevent disservice; offers varied teaching modalities: 1-on-1 instruction and small group instruction.

05:48 Model for integrating young adult components in high schools, emphasizing hands-on training and trades over traditional college paths.

09:23 Early in my career, as a principal in Oakland, my mentor emphasized purpose using the proverb: “One generation plants the trees, another gets the shade.” This taught me that our actions now may not show immediate results, but will eventually flourish, much like nurturing students despite their hardships.

12:24 Embrace imperfection and encourage mistakes for learning without fear of repercussions.

13:54 Guiding students to complete plans and hearing their success stories later is fulfilling and highlights the lasting impact of Pathways.

Why You’ll Love This Episode:

• Be inspired by Dr. Matthew Wienclawski’s authentic leadership journey rooted in community, driven by equity, and focused on transforming educational outcomes through collaboration and clarity.

• Discover how he is working to increase the retention of Black male educators, address the “invisible tax” many educators face, and build leadership pipelines grounded in mentorship, representation, and respect.

• Gain insight into school turnaround strategy, leadership density, and how he leads with clarity, compassion, and cultural relevance, alongside a powerful vision for future superintendency rooted in impact, not ego.

Connect with Dr. Matthew Wienclawski

LinkedIn: https://www.linkedin.com/in/matthew-wienclawski-5869489 

Website: https://pathwaysineducation.org/ 

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Host LinkedIn:  https://www.linkedin.com/in/dougrobertsiei/ 

Company LinkedIn:https://www.linkedin.com/company/institute-for-education-innovation/ 

Company Website: https://www.instituteforedinnovation.com/ 

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